1 comments/ 107572 views/ 58 favorites 14 Memorable Anal Encounters 01 By: walterio AUTHORS NOTE: I decided to submit stories of my life's anal encounters. Of all the women that I hooked up with over the years, fourteen of them included anal sex. Some of these were affairs that lasted for months and some for years. Others were memorable one night stands. Instead of going in chronological order I ranked the encounters according to the hottest ones beginning at number fourteen and working my way to number one. Over my lifetime dating back to 1959 when I turned 18 years old, I have had hundreds of sexual encounters with over fifty women. Being a leg and ass man, my most memorable encounters included anal sex. Most all of my sexual encounters were pleasant but these involved anal sex. INTRODUCTION My age will range from 29 to 48 during the years 1970 through 1990. The one thing that I pride myself on is staying fit through all those years and even today at age 72. I am 6'0" tall and have always weighed between 205 and 215, my current weight. In the early years I played softball, football and basketball. Eventually I shifted to the individual sports of tennis and golf. I am still an avid downhill skier and SCUBA diver and I am still taking martial arts classes. In addition I make it to the gym at least three days a week and I am a ski instructor at a local ski area in the Midwest. I love to travel and although not fluent, I am very comfortable with the Spanish, Italian, and French languages. I am also currently studying Mandarin Chinese. I enjoy reading and the arts and I am a frequent live theater attendee. I have traveled to Spain, Italy, France and the UK over the years as well as some of the best SCUBA diving spots in the Caribbean and best ski mountains in the U.S. and Europe. Some of my other story submissions to literotica speak to my experiences in other countries and islands as well as at home in the states. I served four years in the Marine Corps and I was honorably discharged in 1963. I will begin the stories with number 14 and work my way up to number 1. Due to the length I have broken the stories up into chapters so that a single submission would not be too lengthy. Also there will be some redundancy in the description of sex acts, after all how could there not be. I had my favorite positions and activities and they were often repeated with different partners. The ranking and dates of the encounters are as follows: 1-Cathleen (1985 -1990) 2-Charlotte (1970-1972), 3-Bonnie (1974), 4-Pamela (1973), 5-Beverly (1977), 6-Sherry (1983), 7-Peggy (1976), 8-Lee (1982), 9-Barbara (1984), 10-Rita (1978), 11-Terri (1979), 12-Susan (1971), 13- Toni (1978), 14-Cindy (1973). NUMBER 14 - CINDY I met Cindy in 1973 at a college bar hangout in Cedar Rapids, Iowa. I was 32 years old at the time and still holding my own with the ladies. At 6'0" my weight was holding at 200 pounds and I was in great shape. I still worked out all the time at home and on the road and I played softball for three teams at home. Our manufacturing company headquartered in Ohio was relocating a division office from Illinois to Cedar Rapids, Iowa and I was assigned the responsibility of assuring that the computer systems were installed properly. The local sales representative for our computer vendor made sure that the equipment was delivered on time for the cutover. Randy was a nice guy in his thirties and we hit it off. He took me out for lunch several times on his company's expense account. The day we went live with the new system he wanted to celebrate so he took me out for dinner and drinks. After we ate randy took me to a bar where it was mostly people in their twenties who went there and many of them were college students. The bar was very diligent about checking identification so that everyone there was at least 21 years of age. Randy and I were comfortable talking with the girls there and holding our own with the younger guys. Disco was popular in 1973 and I was a pretty good dancer. I danced with a number of girls but there was one who seemed to pursue me. Cindy was 23 years old and a cute brunette with long straight hair. I loved the way her hair flowed when we danced a hot disco number. I guessed her height to be about 5'5" and her weight to be in the 110 to 120 range. She had a somewhat shapely figure but her waist wasn't that small. Still she was firm and I could feel her hard abs when we danced. She had a cute ass outlined in her hip huggers and medium size breasts that I assumed were real. I tried to put the moves on her to get her to come back to my hotel with me but she shied away. "I don't know," she said each time I asked her. Thinking that I was going to strike out with her I turned my attention to another girl who seemed interested in me. I was dancing with this girl named Sharon when I saw Randy talking with Cindy. After a few dances with Sharon, I excused myself to use the men's room. When I came out Cindy smiled at me and said, "My turn." "To use the men's room," I joked. "Funny," she said and made her way to the ladies room. "I've been working on her for you," Randy said. "Really," I quipped. "Yeah, I've been telling her what a great lover you are. That you spent time in France and Italy and really know how to make a woman feel good. I told her that she would experience nothing like it," he told me. "That's laying it on pretty thick," I responded even though he was right. I had spent time in Italy and France when I was in the Marine Corps and those women taught me a lot about being a good lover. "I think that she likes you but is still unsure. I told her that there is nothing like making it with an older more experienced guy," Randy added. "You make me sound old," I laughed. Just then Cindy rejoined us and pulled me out on the dance floor for a slow dance. I held her tight to me and I knew she could feel my stiff cock pressing into her thigh. "Have you given it anymore thought?" I asked her. "Yes, but I still don't know. I don't know you and that makes me nervous," she told me. "Do you have any friends here?" I asked. "Yes, a couple." "Why don't you give them my name and the hotel where I am staying? I will give you my driver's license so you can get the name and address from it," I offered. "I like that but I have my parent's car and I need to get it back to them," she shared. "I'll follow you to your parent's house so you can drop off the car and then I'll bring you to the hotel. I will bring you back home later," I suggested. "Okay, I'll give Suzie your information and ask her to alibi for me. I'll leave a note for my parents that I'm staying over at Suzie's place," Cindy explained. The dance ended and I gave Cindy my driver's license. I watched as she wrote down the information and chatted with her girlfriend. Suzie looked over at me several times and smiled as if she was giving her approval of Cindy's choice in men that night. Cindy came back and gave me my license and then I told Randy I was taking off. He was talking with a full bodied girl and I sensed that he had had enough to drink that he just hoped for a blow job. He told me he would see me in the morning. I got in my car and followed Cindy to her parent's house. I knew she was serious about coming back with me because she made sure that she did not lose me. There were so many turns in the subdivision that she could have shaken my tail any time. I waited as she went in the house to drop off the car keys and leave her folks a note. Minutes later she was in my car giving me directions to get back to the main road. Once there I drove to the hotel and brought Cindy to my room. As much as I liked anal sex it was the furthest thing from my mind that night as I truly wanted to pleasure Cindy even though she had a cute ass. The first thing I did was to undress her and I did it in front of the mirror in my room. I had Cindy face the mirror and I stood behind her. First I removed her blouse and I kissed her neck and tongued her ear as I unbuttoned it. She shivered and cooed in my arms and then I slid the blouse off her shoulders and down her arms. Looking at her in the mirror I could see that he breasts were indeed real. I unhooked her bra and slid the straps off her shoulders. I eased the straps down her arms and removed the bra letting it fall to the floor by her blouse. Cindy's hands instinctively covered her firm breasts but I pried them off as I continued to kiss her neck. She turned her face to me to be kissed and I pushed my tongue into her mouth. She responded by shoving her tongue in my mouth and we French kissed as I fondled her firm breasts. I felt her nipples harden in my palms and I tweaked them ever so gently. Cindy was moaning softly in my mouth. I let my hand drift down from her breasts along her flat belly and firm abs to the belt around her waist. I unbuckled the belt and then unfastened the buttons on her hip huggers. I broke the kiss with Cindy and I dropped to my knees behind her. I removed her shoes first and then pulled the snug fitting hip huggers down her shapely legs. Being a leg and ass man, I admired Cindy's legs and curvy ass. I removed the hip huggers on legs at a time as she lifted her leg to assist me. I tossed the slacks in the pile with her other clothes. Next I kiss the back of her thighs and she trembled as my lips grazed over her skin. I kissed my way up to her panty covered bottom and then slowly pulled her panties down her legs. Cindy lifted one leg at a time as I removed her panties and there was the distinct smell of sex emanating from her pussy. I planted soft kisses on her buttocks and she surprised me when she pushed her ass back in my face. Suddenly I realized that anal sex may be a possibility that night but I did not rush it. I ran my hand up the inside of her leg and found her pussy to be sopping wet. I toyed with her vulva and fingered her briefly before standing back up. My cock was throbbing in my pants and it was time for me to undress. I removed all my clothes and then totally naked stepped behind Cindy again. I let her feel my hardness against her firm buttocks and she wiggled her ass in response. I turned her toward me and knelt in front of her. I pressed my mouth to her vulva and her hands held my head as if she was afraid that I would stop. She was dripping wet with desire and I tongued her clit causing her to orgasm quickly. Cindy held my head tight to her pussy as she thrust it at me and cried out. "Oh Walt, hold me, hold me tight." I held her by the cheeks of her ass as she exploded in my mouth. Cindy trembled as held to my head for balance. Then her hands dropped to my shoulders for more support. I continued to lick her and tease her clit until she pushed my head away. "Oh I came so quickly. Let me lie down," she pleaded. I pulled the bed covers down and laid her on the bed. She looked radiant as she smiled and held her arms out to me. I moved between her legs as she lifted them out to the side and my rigid cock slid in easily. Cindy gasped as my cock filled her quim and she wrapped her legs around me and locked her ankles together. I was in no hurry to cum and I wanted to please her over and over before I finally did. I was still good for at least two ejaculations and I knew that the second one would take longer. Cindy was turned on beyond belief and she was insatiable. She had two more orgasms and I still had not cum. The last orgasm was so intense that it scared me but she was used to having volcanic like climaxes. She needed to let her clit rest for a while so she moved to all fours and I fucked her from behind. It was my favorite position particularly if the girl had a nice ass and Cindy certainly did. I caressed her buttocks and teased her nether hole which was very tight. I was sure that she never had experienced anal sex. I wet my pinky finger with her pussy juice and eased it into her anus. Cindy stopped moving briefly and then resumed moving her ass around with my little finger in it. "I have been thinking about anal sex but I am still afraid. Your cock is bigger than most too," she whispered. "If you want to try I'm game. We will need to use some cream to get you very slick. If at any time you feel scared or are worried, we can always stop," I told her. "I want to try it," she agreed hesitantly. I eased my cock out of her pussy and then knelt behind her. I lapped at her pussy gathering up some love juice and then I tongued her anus. I thought Cindy was going to leap off the bed when my tongue touched her nether hole. However she loved it and I continued with the anal foreplay. "You certainly know how to get a girl all hot and bothered," she rasped. "I'm going to get some lotion," I told her as I moved off the bed. I got the hotel supplied body lotion and used it to lubricate her anus, I had her pussy juice and my finger was very slick as it entered her rectum. I used my index finger to stretch her a little and then switched to my middle finger. After several minutes of using my fingers, I introduced my thumb to her ass and it was a snug fit. Still Cindy was determined to go through with it and did not protest. I felt she was ready for the real thing and I knelt behind her. I applied and ample amount of lotion to my cock along with my saliva making it as slick as possible. I eased my cock into her ass and she grunted as the mushroom head cleared her sphincter. "Oh, oh, wait," she cried out. "Should I stop?" "No, just stay still for a minute. Let me get used to it," she whispered urgently. I didn't move with just the head of my cock in her ass. Several minutes passed and the n Cindy moved back a little and accepted more of my cock in her bottom. This continued for what seemed like and eternity and even then only about half of my cock was in her ass. That was enough for her though and she controlled the action. She moved her ass back and forth on my cock each time stopping when she felt full. I looked at her beautiful ass as my cock slid in and out and that was enough to get me to cum. "Cindy, I'm going to cum. Do you want me to pull out?" "No, I want to feel it. I want you to cum in my ass,' she replied excitedly. "Here it comes then," I announced as I ejaculated in her rectum. It was a good size load as my first always was and Cindy cried out when she felt the warm sperm flood her rectum. "Oh, oh, oh, yes, I can feel it," she called out. My cock stayed hard in her and I could feel he sphincter contracting and relaxing around my shaft. I waited for several minutes and then I eased my cock out of her ass and watched as my seed trickled out and ran over her pussy down her inner thighs. Cindy involuntarily contracted her sphincter and more semen oozed out of her anus. It was an incredible sight to see her cute round ass expunging semen. I caressed her buttocks until she flipped over. "I feel like I have to poop," she said. "That's natural after anal sex," I told her and then offered, "Let's shower together and get cleaned up." Cindy and I showered together and rinsed the semen from her body. I helped her douche her anus with the shower water and afterward we dried off and went back to bed. We cuddled together and caressed each other causing me to get hard again. Cindy saw my erection and slid down the bed to take it in her mouth. She sucked on my cock giving me a very good blow job. "Turn around," I encouraged her. Cindy rotated around and straddled my face. I lifted my head to get my tongue on her clit. We stayed in the 69 position until I ejaculated in her mouth. Cindy swallowed every drop and let my cock soften in her mouth. She managed another orgasm and I tasted her juices. We eventually moved to a spoon position and I draped my arm over her body and cupped her breast. "Can you take me home? I should get going," she whispered. "You're welcome to stay her but if you want to leave now I'll drive you home," I told her. "Yes, it will be better if I get home early," she replied. We got up and got dressed and I drove her back to her parent's house. I paid close attention to all the street names and turns so that I could find my way back to the main drag. As we drove Cindy told me that she was glad that she tried anal sex but she wasn't sure if she would do it again. Her bottom was still a little sore and she felt constipated. I told her that she would feel that way for a few days and then it would pass. I explained that the sphincter was stretched and it was designed to push things out not to take things in. She nodded that she understood. I dropped Cindy off and we never exchanged contact information. I wasn't sure if I would ever get back to Cedar Rapids anyway. I managed to find the main drag without getting lost and made my way back to the hotel. My flight home was scheduled for that morning but I changed it to an afternoon flight so I could sleep in. It was very easy those days to change flights without a hassle. NUMBER 13 - TONI I had changed jobs in 1976 and I was working for another manufacturing company located in Ohio. In 1978 I played on the IT team in the company intramural volley league. The teams were coed and we had to have at least two girls on the court at all times. One of our players Toni was a recent college graduate and an entry level programmer in our department. She was an attractive young woman but by no means a head turner. She was 6'0" tall and weighed about 145 pounds. Toni had a very straight line figure with medium size breasts. The one thing she had that many tall girls don't have was a nicely shaped ass. Toni was conscious of her appearance at work and she always wore long loose fitting clothes. On the volleyball court it was different as she wore shorts and a tee shirt. That's when I noticed her curvy ass. I had never even given a thought to having sex with Toni as I was currently seeing two other girls who did not work at the company. One evening after one of our games some of us joined Toni by her Volkswagen van for a beer. I had supplied the beer and the cooler was stored in Toni's van. After a couple of beers everyone else left leaving Toni and I alone with the beer. The bugs were getting to be a pest so she suggested we sit in her van and finish our beer. As it turned out we had a few more beers and I was starting to think about getting some pants that night. Toni leaned over her seat to fish two more beers out of the cooler and as she did she put her fine ass on display. I could not resist and I ran my hand over her firm butt. "Nice," I said. "I'll give you an hour to stop that," she said slurring her words slightly with a giggle. "Game on!" I thought to myself and I continued to fondle her shapely buttocks. "Let's get in back," she said in a hurried raspy voice. I suspected that she was horny and in the mood for sex. I climbed in back with her and we lay on the floor of the van. I took her in my arms and kissed her and she kissed me back. Next our hands were fumbling with the other's clothing and I had her tee and bra pushed up baring her cute firm titties. I mouthed them and sucked gently on her nipples as I slipped one hand between her legs and rubbed her snatch through the shorts. I kept my mouth fastened to her tits as I pushed her shorts and panties down below her pussy. I fingered her quim and found it soaking wet with desire. "Shit, shit, oh shit," Toni whispered as I worked on her. I removed my mouth and moved down so I could remove her shorts and panties. Now she was nude except for the tee and bra pushed up above her tits. I moved between her legs and licked across her vulva causing her to thrust her cunt in my face. She continued to utter the word shit over and over as she approached her first orgasm. When I slipped my fingers in and located her g-spot that did it. Between rubbing the g-spot and nibbling on her clit she went wild. Toni juiced my face as her body seemed to go into convulsions. I kept at her and did not let her escape until she was finished cumming and her body went limp. 14 Memorable Anal Encounters 01 I took that opportunity to shed my tee shirt and shorts. My cock was rock hard and Toni took it in her hand and stroked it. Next she went down on me and gave me a fantastic blow job. She maneuvered her body around so that I could get to her pussy again and we ate each other until she came. I still had not cum and I was ready to fuck her but she wanted me to use protection and neither of us had any with us. I was just about to accept cumming in her mouth when she startled and surprised me. "Have you ever fucked a girl in the ass?" she asked coyly. "Many times, I love anal sex," I told her. "Good, let me get some lotion," she replied as she reached for her handbag. Toni took out a bottle of hand lotion and handed it to me. She rolled to her side and pushed her ass back emphasizing its lovely shape. I applied the lotion to her anus and my cock. Then I used saliva to make my cock even more slippery and eased it into her ass. My cock went in easily and I knew that Toni was experienced in anal sex. I wrapped my arms around her with my left hand finding her breasts and my right her pussy. As I fucked her hot ass I tweaked her nipples and fingered her pussy. Toni relaxed a little and felt more of my cock slide into her asshole. She grunted out loud as she felt fuller and a wave of pleasure passed through her body. I kept feeding more and more of my cock into her ass. Toni would tense, relax and enjoy it. This pattern continued until I had all of it buried in Toni's ass. "Oh my God, you feel so big, I feel so full," cried out Toni, "Uh, uh, uh oh yes, it's so good," she cried out. I played with Toni's clit as I pounded her ass. Her pussy and asshole were on fire as my big cock reached the sensitive areas in her passage. Toni was on the brink of another huge orgasm as I methodically fucked her in her tight anus with my sizeable cock. I loved watching my big cock slide out of her shapely ass and plunge back in as my hips slapped against her curvy ass cheeks causing them to jiggle with each thrust. I loved watching her ass impaled on my cock. Toni looked so submissive and vulnerable on the floor of her van as my cock filled her asshole. Her orgasm surged within her as I fucked her ass harder and faster. I loved fucking a shapely ass and Toni's was one of the best I ever had. As Toni had a string of orgasms her entire body went into spasm. Her pussy convulsed and clamped around my fingers coating them with her cunt juice. Toni's asshole pulsated as I drove my big cock in and out of it. Her ass involuntarily squeezed and released my huge member as I fucked it causing me to finally lose it. I slid my pecker deep into her rectum as my cock spasmed and sent a thick stream of hot cum into her channel. I kept fucking her as semen was fired into her ass and my cock kept twitching and spurting inside the impaled rectum. Toni was so full of cum and there was no where for it to go as it was blocked by my swollen cock buried in her ass. I slowed my pace and eventually stopped, allowing my cock to remain buried in Toni's ass. I did not go soft right away and I gently moved my hips pushing cum around in her ass. Some of it trickled out and ran down over her buttock and wet my thigh. Toni could not take any more fucking and she pleaded, "Please no more, I can't take any more, please stop and let me rest." Reluctantly I stopped and slowly withdrew my cock from her loosened asshole. I marveled in the sight of my cock sliding out of her shapely ass. The man seed flowed from her asshole and ran like a river down over her buttock. We stayed in the same position for awhile and I massaged her beautiful ass as she remained on her side. I loved looking at it and playing with it as she cooed in the confines of her van. I could not resist sticking one of my fingers in her asshole and Toni just wiggled her bum slightly in delight. "I shouldn't have done that," she whispered. "Why? You were wonderful," I assured her. "No not that, the sex was great. I shouldn't have slept with someone from work," she explained. "I'm not going to tell anyone. I don't kiss and tell," I replied trying to put her at ease. "I appreciate that but I still shouldn't have," she insisted. Toni and I put ourselves back together dressing the best we could in our volleyball clothes. It was dark out when I left her van and walked back to my car. Toni pulled away and I got in my car and drove home. We had been having sex in her van for hours and it had only seemed like minutes. I saw Toni again at work and at volleyball but true to her word we never hooked up again. Still butt fucking in a van had made me feel younger than my age at 36. NUMBER 11 -- SUSAN In the summer of 1971 I met Susan at a party. She and I both worked in the IT division but not the same department. We hit it off at the party and Susan and I later went to her apartment. At 23 years old Susan weighed just under a 100 pounds and she had the typical model figure. Even though she was thin she had the curves and bumps in the right place. Susan had small firm cute tits, shapely slender legs and a very cute round bubble butt. She wore her blonde hair short just over her ears. Susan was a natural blonde and she the cutest little tuft of blonde fuzz on her pubes. Susan was not at all into giving head but she loved to have her pussy eaten as I learned that night. We wasted no time in getting our clothes off and into Susan's bed. Earlier that night at the party, I had butt fucked a girl named Charlotte in the downstairs bath room. Charlotte is number two on my list and you will learn about her later. Since I had already cum once that night I was in no hurry to get my rocks off. In fact I focused all my attention on Susan's pleasure. We kissed with our naked bodies rubbing together and I fondled her tits and curvy ass. Then I began my pursuit down her body. I spent quite a bit of time sucking on her tits and nibbling on her nipples. I left her tits and trailed kisses over her abs down to her pubes. I skipped Susan's pussy and kissed her inner thighs. Susan had her head thrown back and her mouth was wide open as if she was going to scream but no sound ever came out. I moved my mouth to her pussy and flicked my tongue over her vulva. I probed her outer cunt lips with my tongue and then drove it in separating her inner lips. Susan's body tensed as I worked on her pussy as if she was going to cum. I swabbed my tongue around inside her pussy and flicked it over her hooded clit. I pushed a finger into Susan's pussy and wormed it around as I tickled her clit with the tip of my tongue. Susan's body went into convulsions as her first orgasm overtook her. She grabbed my head and held it to her pussy as she humped my face for all she was worth. I held her tightly as she sprayed my face with her female nectar. Susan had a very tasty pussy and I enjoyed eating her to multiple orgasms. Susan's mouth was still wide open as her body lifted off the bed. I grabbed onto her cute ass firm cheeks and held her tightly against my mouth. Susan then shook violently and collapsed on her bed. I kept right on eating her and I soon had her aroused again. This time I pushed a pussy lubricated finger into her tight asshole causing Susan to freeze. I was to learn later that it was her first anal penetration. Susan went along with it as it felt strangely good to her. Susan then asked me to fuck her so I moved between her legs and slipped my rock hard cock into her very wet but snug pussy. Susan gasped when my cock hit home and I was to learn later that I was the biggest she had had in her up to that time. Susan was so thin that I could feel the sharpness of her pelvic bone as I fucked her. Susan worked to keep her clit in contact with my cock and in no time she was cumming again. Susan thrashed and writhed under me as she had a mind blowing orgasm. Susan then asked me not to cum in her pussy. I learned later that she was nervous about where she was in her cycle, better safe than sorry. I pulled out of her and laid my cock on her abs between our bodies. I kept moving as if I was fucking her and then I shot my load between our bodies. My semen shot out of my dick but it was immediately trapped between our bodies. Susan thanked me for pulling out of her pussy and she told me it was cool to cum on her rather than in her. Susan and I lay together for awhile longer and then I cleaned up, dressed and left for home. The next time Susan and I got together I was on my way home after having a couple of drinks at the Oasis, a bar that sponsored our softball team. Susan was coming in just as I was leaving. I told her no one was at the bar but I offered to buy her a drink if she wanted one. Susan smiled at me with her sultry look and said, "No, why don't we go to my place and fuck." "Sounds good to me," I replied and then I followed Susan as we drove over to her apartment. Just as we did the first time we wasted no time getting our clothes off and getting into her bed naked. Susan was really horny that night and she came quickly and often as I ate her pussy and fucked her. I still had not cum when she asked me to stop and let her rest for awhile. Thinking that her pussy needed a break I asked her about anal sex. Susan told me that she had thought about it but never tried it and that my finger was the only thing that had ever been in her ass. I talked her into taking a bath with me thinking that I could get her ass clean and then turn her on with my tongue. Susan ran a bubble bath for us and when we sat in the tub she leaned back into me. I reached around and played with her titties and her pussy for awhile. Then I moved my finger to her ass and I used the soapy water as lubricant as I finger fucked her ass. Susan got used to the penetration and allowed me to finger fuck her bottom. Then we got out of the tub before we turned into prunes and dried off. I had Susan lay face down on her bed and I pushed her cute round ass cheeks apart and exposed her delicate nether hole. The pink aperture looked squeaky clean and I lowered my tongue to her asshole. Susan gasped when she felt my tongue rim her anus. At first she stiffened and then she relaxed and enjoyed the oral stimulation. Susan was clearly getting turned on and she let me know it. "Walt you really know how to get a girl turned on," she sighed. I lifted Susan up by her hips and then I began to lube up her tight ass with her body lotion. I wet my finger and it slid in easily when the saliva mingled with the lotion. I finger fucked her asshole and then added a finger to her pussy so that I was finger fucking both her holes at the same time. Susan put her head down on the bed and turned it to one side with a look of ecstasy. I decided it was time to go for it. I removed my fingers from her ass and pussy and lined up my rock hard cock with Susan's asshole. I pushed slowly but she was too tight and her sphincter did not open easily. Just the head of my cock was in her ass but I was so turned on that I ejaculated in her ass. Susan screamed and panicked. She moved away from me and threw herself face down onto the bed. The rest of my load landed on her buttocks. "No don't, it hurts too much. I don't want to do this," she pleaded. I leaned over and whispered in her ear, "I don't want to hurt you. Don't worry I won't fuck your ass." Susan rolled over and held her arms out to me and I moved between her legs and slid my raging hard-on into her tight pussy. We fucked liked demons until I blasted a huge load into Susan's pussy. Susan came multiple times again and then she went limp under my body. I was still hard after cumming so I continued to fuck her. "No please, give my clit a break. I can't take any more tonight," Susan begged. I pulled out of her and rocked back on my legs. Then I rolled Susan over into a doggy-style position and slipped my cock back in her pussy. Susan was in a totally relaxed state and she let me have my way with her in this position. I played with the cheeks of her cute bottom as I fucked her from behind but I did not penetrate her ass again that night. I eventually came for a third. Susan dropped face down on the bed as she was done for the night. I washed up in her bathroom, dressed and then kissed her on the cheek when I left. The next day Susan stopped by my office. She came in and closed the door. I could tell that she was nervous or almost scared. "Walt, there was some bad stuff that came out of my ass this morning. You can't ever put anything in my ass again. I don't want you near my ass again," she rambled in a panic. "Susan I understand. Look I know it was the combination of my semen, the lotion and maybe a stool that made it look so bad. You're okay you're not injured. I stopped as soon as you told me too," I replied trying to put her at ease. "I don't know what it was but it looked nasty and it scared the hell out of me," she countered still shaken. "I'm sure it scared you but I promise you I know that you will be fine. I never did fully penetrate you," I said trying to calm her. "I know that you didn't and I thank you for not forcing yourself on me. I know that you care and that you are a good lover. I just freaked out," she said almost sobbing now. I stood up and held her until she calmed down and relaxed in my arms. Susan eventually left my office composed but she was resolved that anal sex was not going to happen with her. Susan and I got together a few more times and we always had great sex. She started dating a pilot for one of the charter companies so my time with her came to an end. But one night after one of our softball games Susan showed up at the Oasis. She asked me back to her place and I guessed the fling with the pilot was over. We made passionate love that night and afterward as we lay naked together Susan told me that she hadn't heard from the pilot in weeks. She had been too proud or too stubborn to call him and she was upset. It was obvious that she really liked the guy and she was devastated that he had just dropped out of sight. I told her that she should call him and clear the air one way or the other. Susan agreed and just then the phone rang. Susan grabbed the phone before the second ring and I watched her face break into a joyous expression. "Hi, how are you? I was just going to call you. I've been worried about you," Susan rambled on. It was odd because we were both naked in her bed as she got caught up with her pilot boyfriend. I slipped out of bed and quietly got dressed. Then I leaned over and kissed Susan on the forehead and gave her a thumbs-up as I left. She smiled at me and blew me a kiss as I left her apartment. That was the last time Susan and I ever made love. NEXT CHAPTER -- MORE ANAL ENCOUNTERS 14 Memorable Anal Encounters 02 AUTHORS NOTE: I decided to submit stories of my life's anal encounters. Of all the women that I hooked up with over the years, fourteen of them included anal sex. Some of these were affairs that lasted for months and some for years. Others were memorable one night stands. Instead of going in chronological order I ranked the encounters according to the hottest ones beginning at number fourteen and working my way to number one. Over my lifetime dating back to 1959 when I turned 18 years old, I have had hundreds of sexual encounters with over fifty women. Being a leg and ass man, my most memorable encounters included anal sex. Most all of my sexual encounters were pleasant but these involved anal sex. INTRODUCTION My age will range from 29 to 48 during the years 1970 through 1990. The one thing that I pride myself on is staying fit through all those years and even today at age 72. I am 6'0" tall and have always weighed between 205 and 215, my current weight. In the early years I played softball, football and basketball. Eventually I shifted to the individual sports of tennis and golf. I am still an avid downhill skier and SCUBA diver and I am still taking martial arts classes. In addition I make it to the gym at least three days a week and I am a ski instructor at a local ski area in the Midwest. I love to travel and although not fluent, I am very comfortable with the Spanish, Italian, and French languages. I am also currently studying Mandarin Chinese. I enjoy reading and the arts and I am a frequent live theater attendee. I have traveled to Spain, Italy, France and the UK over the years as well as some of the best SCUBA diving spots in the Caribbean and best ski mountains in the U.S. and Europe. Some of my other story submissions to literotica speak to my experiences in other countries and islands as well as at home in the states. I served four years in the Marine Corps and I was honorably discharged in 1963. I will begin the stories with number 14 and work my way up to number 1. Due to the length I have broken the stories up into chapters so that a single submission would not be too lengthy. Also there will be some redundancy in the description of sex acts, after all how could there not be. I had my favorite positions and activities and they were often repeated with different partners. The ranking and dates of the encounters are as follows: 1-Cathleen (1985 -1990) 2-Charlotte (1970-1972), 3-Bonnie (1974), 4-Pamela (1973), 5-Beverly (1977), 6-Sherry (1983), 7-Peggy (1976), 8-Lee (1982), 9-Barbara (1984), 10-Rita (1978), 11-Terri (1979), 12-Susan (1971), 13- Toni (1978), 14-Cindy (1973). NUMBER 11 -- TERRI It was in Pittsburgh that I met Terri in 1979. I had joined a software company that year and I was attending a product training session. There were a number of customers at the session as well but none of them really appealed to me at first. After the third day I had dinner with a couple of attendees and a young woman named Terri seemed attracted to me. After dinner I invited her to have a night cap with me at the bar. From there things moved quickly and it was obvious that she was horny that night. Terri was wearing a tasteful business suit and it fit her nicely. I guessed her to weigh about 100 pounds and I noticed her nice legs. The skirt fit her snugly showing the curve of her cute ass. Teri was not a beauty by any means but she was attractive in a different way. We left the bar and she accepted my invitation to my room. Once in side we were kissing on the bed and I began to remove her clothes. In spite of her horniness she was shy. I removed her jacket and blouse and noticed that her skin was lily white. She obviously was not a sun lover. I removed her bra and bared her small tits. When I kissed her breasts and sucked on her nipples she cried out. It was apparent that her tits were very sensitive but I suspected that they didn't get that much attention. I unfastened her skirt next and removed it leaving her in her pantyhose and panties. Terri crooned as I removed her hose and panties together and now she lay naked before me. I kissed my way up her legs and then spread them to look at her pussy. She had a small tuft of reddish brown hair above her nice looking pussy. I dipped my tongue in her tasting her and found her to taste sweet. I ran my tongue over her clit causing her to cry out again. Just a couple of swipes and she exploded. "Oh God this is a quick one," she cried out. I held her hands at her side and sucked on her twat driving her wild. Terri thrashed all over the bed and then her orgasm subsided and she was still. I stood up and removed my clothes and I followed her eyes to my cock. She seemed nervous about my size so I knew that I should take it easy with her. I moved between her legs and that's when I discovered what made her nervous. I could not get my cock in very deep as she had a shallow vagina. "Oh I should have told you. The doctor said I would have problems because I'm not very deep," she whimpered. I felt sorry for her and told her not to worry about it. "I can still cum but I don't want to hurt you," I assured her. I held my cock in my hand and ran the head along her clit and let it dip in every so often. Terri was getting excited again and she climaxed before I was close to cumming. "How about oral, do you like that?" I asked. "I can do that," she agreed and moved down to take my cock in her mouth. Terri was a willing but inexperienced cock sucker and she tried to please me. She was on her belly lying across the bed as she sucked on my cock and I began to play with the cute ass. I fondled her cheeks and dipped my finger into the crack. "Have you ever done anal?" I asked. "No but I am willing to try if it will make you happy," she replied. "Let's give it a go. I promise I will be gentle with you. If you want to stop, tell me," I told her. I moved behind Terri and lifted her hips into the air. She kept her head on the bed turned to one side with an apprehensive look on her face. I got out of bed and got the lotion from the bathroom. Terri's ass looked very inviting and I lubricated it thoroughly. She moaned softly and the penetration of my finger and soon relaxed with the intrusion. I was able to add a second finger and in spite some discomfort Terri didn't complain. I knew it was going to be a challenge for her to take my cock in her ass. I was getting more and more turned on fingering her bum and I had to try and fuck her. "It's time to fuck your hot ass." "I'm scared," Terri said nervously. "Relax, I won't hurt you." I poured more lubricant on her ass and worked it into her asshole. Terri arched her back and pointed her beautiful ass back at me. I then coated my entire cock with the lube and placed it at entrance to her anus. I pushed forward and the soft mushroom head squeezed into Terri's tight asshole. Terri winched in pain as her asshole was stretched wider than ever and she gasped, "Go slow let me get used to it." Satisfied that she was well lubed I straddled her hips and dipped my slick cock into her pussy to coat it with juices and then I eased it into her ass. My cock head slipped past the moistened sphincter and the spongy head disappeared into her ass. Her anal ring snapped closed behind the cock head and I marveled at the sight before me. I only had the head of my cock in her and she lifted her hips as if she wanted more. "Not too deep at first and then go deeper little by little," she whispered as a caution to me. My cock felt bigger than it ever had as I eased more of it into her anal passage. I watched as it stretched her open and entered her slippery hole. I continued my slow penetration until the entire length of my shaft was balls deep in her ass. Terri gasped and grabbed the bed sheets as I hit bottom and then she moved her ass in time with my thrusts. "Let's fuck on our sides," she rasped. I rolled both of us to our left side and settled into the spoon position with my cock buried in her asshole. My left arm came around and fondled one of her tits and tweaked her nipples as my right hand sought out her pussy. I pushed two fingers into her pussy and rubbed her clit as I fucked her ass and played with her tits. Terri was going wild as her orgasmic, constricting muscles gripped me firmly. We fucked slowly as she arched her back and we fitted together perfectly. Her gasps were intermittent and interrupted with cries and sobs of pleasure. Her ass felt so snug at that moment that I wondered how the semen would ever get out of my cock. I fought to hold back my orgasm as long as possible but the undulating walls of her asshole were just too much. I felt the familiar boiling in my balls and I thrust into her as the first blast of cum exploded into her rectum. I barely heard her pleas for me to fill her ass with cum as her contractions milked every drop from my cock. I continued to fuck her slowly and I enjoyed the new feeling of warm semen surrounding my cock in her sheath. "I love the feel of your warm cum in my ass. I never thought that I would but I do," she sighed as my cock remained nestled in her hole. For some reason I stayed hard and I kept right on fucking Terri's ass. I pummeled her ass as I sought out another ejaculation. Terri's ass was loser now and slippery from the combination of the lube and my semen but she was still snug around my cock. Once again I stiffened and fired a load into her rectum. I could feel my cock pulsate again as it released my man seed deep into her anal recess. We lay still for a few minutes recovering from the intense fuck session. I had forgotten about my cock in her ass until it had softened and slipped from her hole. I felt my wet cock drop on my thigh and I knew that cum was trickling out of Terri's asshole. We rested several minutes and then I suggested a shower. We both showered together and washed in each other's body. Then Terri put her clothes and back on and went to her hotel room. The next evening it was déjà vu as Terri looked forward to being with me again. This time I went to her room. She was already naked when I arrived and she quickly ushered me in her room. She ran and jumped in her bed and wiggled her ass at me. "I douched both my ass and pussy for you tonight," she uttered in a sultry tone. I walked toward the bed and by the time I got my clothes off my cock was rock hard. I leaned over and licked Terri's pussy from behind driving her wild. I could tell that she had dabbed a very fragrant perfume between her thighs and on her ass cheeks. I had the urge to tongue her beautiful ass so I swiped my tongue from her pussy up and over her bung hole and back to her pussy. She gasped out loud when my tongue touched her asshole. I really got into it and grasped both of her curvy ass cheeks and pulled them slightly apart so that I could get my tongue in deeper. I probed her pink aperture with my tongue as I inserted my fingers in her tiny pussy. She started whimpering, gasping and directing the action. "Oh my God, do it again. Lick my anus; stick your tongue in there. Eat my pussy, tongue my ass, rim me, oh yessssss," she cried out and then added, "I'm all yours. Do anything that you want to me." I let my saliva trickle down over her anus and pussy. I placed my mouth on her and drank up my own spit swabbing her pussy and ass in the process. I repeated this several more times until Terri seemed to go into convulsions with her first orgasm of the evening. "Oh I loved the way you tongued my ass. It felt so wonderful," she uttered in an exhaustive voice. "I loved doing it and it looked incredibly sexy as it glistened with oil. I remembered that you told me that you had douched and it looked so clean," I told her. It was time for me to fuck her in the ass so I had her kneel on all fours with her gorgeous ass in the air. She put her head on the mattress and turned to the side so that she could watch. I broke out the lube and put an ample amount in her asshole. I fingered her ass and pussy at the same time. "I love the feel of your fingers in my ass and pussy together," Terri exclaimed! After several minutes of finger fucking her pussy and asshole I couldn't wait any longer and I had to get my cock in her shapely ass. I removed my fingers and lined up the head of my cock at her moist puckered ring and pressed forward slowly. My cock head strained to pop through and she let out a little groan as the pressure from my iron hard dick forced her little ring to open like a flower and suddenly the large mushroom head slipped past the ring and into her ass. Terri let out a groan as her rear passage was stretched to accommodate my ample girth. "Oh you are going to make me like this more than anything," she gasped and shivered as I filled her fully and withdrew my penis slightly. I felt her ass tighten around me and I continued to slowly stroke in and out of her tight ass until all eight plus inches were tightly packed up her ass. Terri really began to moan and her whole body shook in anticipation of what she knew was coming. I began to slowly fuck her but soon picked up the pace as I penetrated her with long hard strokes that used the entire length of my thick cock. Terri was going wild as she loved the feel of my cock as it pulled out and then came crashing back in as my big heavy balls bounced off her clit. Terri was thrashing around uncontrollably, gasping and moaning with pleasure. When I reached underneath her to stroke her clit she exploded with another orgasm. I continued to hammer her ass with long strokes then suddenly I felt that familiar tension in my balls and I knew I was close. I began to piston my raging cock harder into her searing ass in search for my release, which also increased the intensity of her orgasm. She was yelling and moaning, clawing and scratching at the bed cover begging me to cum. "Give it to me, give it to me, give me your cum, cum in my ass," she begged. I took firm hold of her hips and slammed once more full force into Terri's ass. I did that three or four more times and then I let out a loud groan as I emptied my seed deep into her bowels. I couldn't believe how much cum I produced as my dick continued to hammer into her ass. I didn't stop fucking her as my cock stayed hard. I knew that I could cum again so I kept at her ass. Terri was groaning and whimpering as I drilled her ass. Soon she stopped moving but remained on all fours impaled on my cock. I could feel my previous load squishing around in her rectum and it was a bit of a turn on. I enjoyed watching my cock slide in and out of her curvy ass. I caressed her shapely buns as I fucked her and I loved watching them jiggle when our flesh slapped together. I felt another surge in my loins and within minutes I was shooting another impressive load into her ass. My body stiffened as I pushed my cock in as far as I could and shot ropes of semen into her rectum. Terri anal muscles involuntarily clenched around my cock and milked the semen from it. Amazingly I stayed hard as her muscles massaged my shaft and I slowly began to move my hips again. Terri's body was almost lifeless at this point and she wanted to lie down but I held her by her hips as I continued to fuck her ass. I don't know how long we fucked but my thigh muscles were aching and cramping. I pulled out of her ass as Terri lay on the bed utterly spent. I slumped down next to her quivering body. I looked over at Terri and I noticed my seed running out of her asshole. It was a very erotic sight as it seemed like an endless stream oozed out of her anus and down between her inner thighs. Terri whimpered as she lay face down on the bed. I reached over and stroked her beautiful ass lovingly. Thirty minutes had passed before either of us spoke. "I feel like I just had an enema," Terri said softly. "It feels like your cock is still in there," she said as she stroked her ravaged ass with her hand. I reached over and caressed her ass as I thanked her for a wonderful time. "That was great anal sex," I murmured. "I have to go to the bathroom," Terri announced as she swung her legs out of bed. I watched her walk into the bathroom and I again admired her shapely legs and curvy bubble butt. I noticed that semen was running down her legs but she didn't seem to care at the moment. Terri was in the bathroom several minutes and then I heard the water running in her tub. She came back out and she looked drained. "I need to take a long hot bath and soak my body. Do you mind?" she asked. "Not at all, I have an early flight in the morning and I could use a good night's sleep," I told her. I kissed Terri goodnight and got dressed while she was in the tub. I went back to my room and set the alarm for morning. Early the next morning was up before the alarm. I showered, dressed, packed and checked out of the hotel. I had breakfast at the airport and as did, I thought about how things had turned out. I had not expected to get laid when I first arrived and I certainly had not expected to have great anal sex. Taking Terri's anal virginity was a thrill for both of us and I was flattered that she so willingly gave up her ass to me. She certainly made up for the limitations of her vagina and proved to be a good lover. I never did run into Terri again after that week but I never forgot those two nights of great sex. NUMBER 10 -- RITA It was a Tuesday evening in October 1978 and I had worked late at the office. I decided to stop for a drink at a bar called the White Rabbit where I had gotten lucky sometimes. There was nothing going on when I got there but I spotted Dick a friend of mine. I joined him for a drink at the bar and it was nearly 9:00 PM when I was about to call it a night. Just then a cute woman with pixie haircut came in by herself. She could have sat alone at the bar away from us but she chose to sit near Dick and me. She smiled as she got up on the bar stool and ordered a drink. "That's on me I told Tommy the bartender." "Thank you," she accepted and smiled again. Upon a closer look I guessed she was in her early to mid forties. She was somewhat short close to five feet tall and she had a decent figure. Her drink arrived and she held up the glass in a toast and said, "I'm Rita and thanks for the drink." I held my glass up and said, "Your welcome, I'm Walt and this is Dick." Over the next 20 minutes or so we got acquainted and had another drink. Dick sensed where things were headed so after his drink he excused himself and left. He whispered to me on the way out. "I'm going to stop at the lounge if things don't work out here, I'll see you there." The lounge was another bar where we often stopped but many people from the company went there and it wasn't the most discreet place. Rita and I continued our conversation after Dick left and I learned that she was a nurse at the hospital. I saw her glass was empty so I offered her another drink. "No thanks, would you like to come to my place for a nightcap?" she offered. "Definitely," I accepted and I finished my drink and paid the tab. Rita walked ahead of me out of the bar and I admired her shapely ass as it filled out her pants. She certainly was a confident woman. We got in our cars and I followed Rita to her apartment complex. I parked my car and walked with her to her apartment. Once inside she said, "Do you really need that drink?" as she pulled her top over her head. "No, I don't, I replied as I watched her undress She pulled the top over her head and folded it neatly and placed it on the chair. Next she peeled off her pants and placed them on the chair as well. Then she took off her bra and I admired her shapely figure, her medium sized breasts and her muscular legs. Finally she smiled at me as she removed her panties and faced me in her naked beauty. 14 Memorable Anal Encounters 02 "Are you going to join me or just watch?" she asked teasingly. I smiled back at her and I undressed as she watched. I removed my three piece suit, shirt, tie, shoes and socks. When I got to my boxers I purposely allowed the waistband to catch my cock as I lowered them. My erect cock jumped out as the boxers released it and I smiled at Rita's reaction. "You know Ohio has laws against carrying a concealed weapon," she said as she subconsciously licked her lips. "Well it isn't concealed now is it?" I replied. "No, it isn't," she responded with a chuckle. She retrieved a tube of lubricant and tossed it to me. Then she got on the bed on all fours. Looking over her shoulder she smiled and spoke softly. "Put plenty of that stuff in my ass and on your cock. I need to be well greased to take that ass buster of yours," clearly stating what she wanted. I moved toward the bed and climbed on it behind her. I massaged her shapely ass cheeks and molded the firm flesh in my hands. Rita shivered in anticipation and goose bumps appeared on her buttocks and thighs. I squirted the lube directly on her nether hole and pushed it in with my index finger, moving it around until my finger was gliding in and out easily. Before adding a second finger I put more lube in her ass and then inserted my middle finger along with my index finger. She cooed as she accepted the two finger penetration and stimulation. As I fingered her ass with two fingers I slipped my ring finger and little finger in her pussy. I sawed the four fingers in and out of her asshole and pussy until she begged for my cock. "Stop teasing me and get that big cock in my ass," she gasped. I put gobs of lube on my cock and then added my saliva making it as slippery as possible. Rita lowered her head to the bed and turned it to one side as I began my journey into her ass. I pushed my hips forward as I held onto her hips and my cock bumped up against her sphincter. Rita gasped and placed her hand on my thigh as if to control the penetration. Another push and my cock head was in her ass. She was holding her breath as I inched more and more of my cock into her anal passage. I told her to relax and breathe as I slowly fed my cock to her a little at a time. I eased it in, stopped, withdrew a little and then pushed some more in. I took my time and I was careful not to hurt her as I filled her shapely ass with my raging shaft. "Oh sweet mother of God, I have never been so full. Go easy but put it all in. I want your whole cock in me," she cried out. I pushed once more and the final inch of my cock disappeared into her asshole. I remained still for a moment and allowed her to adjust to the girth of my cock and then I began to fuck her ever so slowly. She eventually began to move her hips in an attempt to match my thrusts but it was obvious that she had been stretched to new dimensions. She was gasping and grunting as I began to pummel her ass. When I reached for her pussy I found her hand already in place frigging herself frantically. I picked up the pace and held to Rita's shapely buttocks as our hips slapped noisily together. She was really into it now and the two of us fucked like maniacs. "Oh yeah that's it, that's the way to fuck my ass. Give it to me, cum in me, cum in my ass," she screamed. We were both sweating from the physical intensity of our butt fucking. I slammed into her as my cock now moved freely in her ass. I felt my orgasm approaching and as much as I wanted to prolong the ass fucking session, I couldn't. My body stiffened and I plunged my cock all the way into her gorgeous ass. Streams of semen shot into her rectum as I seemed to cum continuously for several minutes. "Oh good, I feel it. Fill me up, fill up my ass," she cried out and then her own orgasm hit her, "Oh shit, here it is, I'm cumming!" Her body thrashed around as I held onto her curvy ass cheeks and kept my cock buried in her ass. Her fingers flew over her pussy and clit as my warm seed flooded her anal passage. She then collapsed face down on the bed and my cock slipped from her ass with an audible pop. I knelt over her as my cock dripped the remaining cum on her curvy ass. She wiggled her bottom and squealed in delight. "I have to admit it Walt that I have never been ass fucked like that. You are one hell of a butt fucker," she said and then rolled onto her back and looked at my semi hard cum dripping cock. "Do you like to eat pussy?" she asked with a tone of hope. I moved my head between her legs to eat her pussy but first I kissed and licked around the area and her inner thighs. I breathed warm air right on her snatch and she grabbed my head and pulled it to her cunt. I pulled my head back off her pussy and let my fingers trail to her pussy. I lightly rubbed her outer cunt lips and she twitched with each touch. She moaned as her clit responded to the stimulation and slowly exited its hood looking for attention. I placed my fingers on her cunt lips and trapped her clit between them and it became engorged and stood erect. She squirmed in pleasure while I moved her cunt lips up and down on her clit and she shuddered from the extreme arousal. Still moving her cunt lips up and down, I bent down and kissed her clit. She jerked and bucked as my lips touched her upright nub. I drew my head back a bit and again blew air directly onto her clit as she writhed and bucked again, moaning with pleasure. I placed my arms behind her knees and raised her hips up. I put her legs over my shoulders and I lowered my mouth to her pussy and kissed it as though it were her mouth. She groaned with delight as she waited for my next advance. I drew my tongue along her outer labia, up one side and down the other without touching her clit. "Suck it please, please lick it, oh please!" she moaned lustfully. I flicked my tongue across the edges of her pussy as she quivered and seeped her juices from between the lips. I licked the juices from the edges telling her she tasted delicious. She was nearly mad with desire as she begged me to pleasure her with my tongue. I parted her labia with my tongue and licked the insides of her cunt lips, nibbling each one a little and then sucking on them both. She whimpered and moaned when I suddenly plunged my tongue as deep as I could into her pussy. She screamed with delight as my tongue explored the insides of her pussy. Instinctively, she grasped my head and pulled it into her cunt, begging me to lick and suck her. I did not disappoint her as I swirled my tongue around her engorged clit and back into her sopping wet cunt. She was constantly moaning as my lips closed about her clit and sucked her clit in and out of my mouth. Writhing and gyrating she exploded in another powerful orgasm, drenching my face and mouth with her copious juices. She seemed to cum with each spasm of her body. I did not let up sucking her clit and she tried to push my face away as she cried out. "Oh stop, please stop. I can't cum anymore let me rest," she begged. Her body shuddered through yet again another orgasm and she lay there gasping and breathing heavy as her orgasm abated. Finally her orgasm subsided and she embraced me and kissed me. I knew that she could taste her own juices on my lips and I plunged my tongue into her mouth taking her breath away. "That was marvelous, absolutely incredible. You are quite the lover," she sighed. By now my cock was rock hard again and I moved between her legs. I eased my cock into her sopping wet pussy and she wrapped her legs around my torso. "Is there no end to this?" she asked playfully. "Not just yet anyway," I replied and I began to fuck her gently. Slowly, I moved into her. Rita opened beneath me, enveloping my penis tightly. Her cunt was like a fist as she clenched her vaginal muscles. She squeezed me as I moved within her. "Rita," I groaned, "You are really tight." She moaned in response, "Your cock feels so good. Fill me up with it." I thrust into her deeply and I felt the head of my cock pressing against her cervix. "Oh Walt," she sighed with her eyes closed. I felt her vagina contract around my cock. She climaxed again with a shudder and a long moan and she urged me on, "Fuck me baby. I can take it, I want it." I grabbed her hips in my hands and began to thrust in and out as I pounded her pussy. My heavy bloated testicles slapped against her ass as my cock drove into her hot pussy. "Yes, oh yes," she gasped as her body rose to meet me. The bed was now rocking with the force of our fierce, animalistic fucking. Her legs clamped around my waist as she screamed her release. Her pussy grasped my cock, squeezing it and milking it as I fucked her. I moved my hips against hers and buried my cock to the hilt within her. Her quaking pussy erupted into orgasm again as I rocked my cock slowly, grinding the head against her cervix. I felt my orgasm building in my balls and I knew that any second I would be spewing my seed into her womb. I felt my semen travel from my scrotum through my cock as I came deep inside her flooding her waiting warmth with my load. Neither one of us could speak as the pleasure was so intense. I collapsed on her and she wrapped her arms and legs even tighter around my body. I kissed her neck and she sighed aloud then I kissed her on the lips and our tongues dueled with each others briefly. Not wanting to crush her I rolled off her as my cock deflated and slipped from her cum filled cunt. "Between my ass and my pussy I feel as if a fire hose was turned on me," she sighed. "I need a shower. Want to join me?" she suggested. I agreed as we were both dripping wet with perspiration from the intensity of our love making. The night had turned out better than I could have hoped it would. Rita and I showered and washed each other's body. I loved soaping up her tits and raising her hard nipples. She was fascinated with my cock and seemed to enjoy handling it and cupping my big balls. After the shower I offered her a massage. She handed me a bottle of massage oil and got back in bed on her back. "Do my front first," she said sexily. She closed her eyes as I gently placed the fragrant oil on my hands and with two fingers on each hand I made small gentle circles over her forehead. I then moved to her cheeks, massaged her nose and her lips, and her chin, then back to her temples and down the side of her face and neck. Leaning over her I slipped my oily hands over her breasts. She smiled at me and I bent my head and kissed her gently. She reached up and took my hands and pressed them to her breasts as her hardened nipples pushed against my palms. I held the bottle of warm oil above her breast and a single drop splashed on her nipple and ran down her side and she flinched with the sensation and giggled at the action. I smiled back at her and poured a small trail of oil down her stomach and then I began massaging her breasts, one in each hand as I looked into her eyes. She glanced upwards again to watch as my hands moved down to her ribs and chest and stomach, spreading the oil until she was glistening in the dim light of the room. I knew she loved the feeling as my hands moved over her breasts, chest, and stomach. She looked at my crotch and saw that my cock was fully aroused and sticking straight up. She smiled as she reached and gently grasped my cock in her tiny hand. I let out a small moan as she moved her hand up and down my huge shaft. She took some oil from me and placed some on the head of my cock then and she placed her palm over the top, gently squeezing and releasing the pressure on my shaft. She spread the oil over my cock as she continued to stroke me squeezing her hand around the shaft as she felt my hand move over her pubic hair. I moved my hand downward until my hand covered her entire moist area. Rita spread her legs as my middle finger probed the folds of her labia. Gently I inserted my finger sliding it in effortlessly within her warm channel. Rita began stroking me in rhythm to my finger entering and withdrawing in her pussy. I was afraid that I would cum if she continued to work my cock in her oily hand so I removed my finger from her pussy and massaged her thighs. I put plenty of oil on her luscious thighs and rubbed it in thoroughly. Her quad muscles relaxed under my movements and she emitted an audible sigh. I worked her inner thighs and massaged them all the way from her knee to her pussy letting the back of my hands brush against her pubic mound. Her engorged clitoris peeked out of her pussy lips and I trapped it between two of my oily fingers. Rita jumped at the contact and once again she reached for my cock. "Make love to me again," she whispered. I pulled her legs apart and let her guide my cock into her pussy. I eased my thick cock into Rita's tight cunt and worked it slowly until I was balls deep in her pussy. I knew that she had never been so full until that night and that she could probably feel every ridge and vein of my cock touch her vaginal wall. Rita gasped again when I hit bottom. As I fucked her slowly I made sure that my cock never lost contact with her clit. Rita stiffened as she orgasmed and then grunted and groaned through multiple orgasms as her body was rocked with one climax after the other. As I pounded her pussy my cock moved easily in her now soaked pussy. Rita stiffened one more time, screamed and then went limp with her final orgasm which was the most intense of the night. The two of us were drained, sweaty and oily as we slowly recovered from our intense fuck session. "My God I will never be the same after today," she gasped. "You bring out the best in me," I teased. "I need to rest for awhile," she said as she rolled over on her stomach. I'll do your back now and finish the massage," I offered. Rita just sighed so I oiled up my hands, straddled her body and went to work on her shoulders. She cooed as I rubbed the tension out of her upper body. I worked my way down from Rita's shoulders to her trap muscles and lower back. I massaged her back just above her buttocks and she continued to coo and moan with pleasure. I bypassed her ass for the moment and went to her calves. I massaged each calf and worked my way up to the back of her thighs. As I massaged the back of her legs and thighs my eyes were fixed on her marvelous ass. I finally reached the object of my desire and I rubbed plenty of oil onto Rita's buttocks. She lifted her hips slightly as I worked her firm ass cheeks. I pulled her buns apart slightly and stared at the cute little aperture. It was hard to believe that earlier my thick cock had been buried in that tiny hole. I leaned over and ran my tongue over her nether hole causing her to gasp in surprise. I suspected that no one had ever rimmed her before and she moaned again as my tongue probed the target. I traced my finger over the ridges of her now swollen sphincter and watched as it seemed to pulse and throb under its own accord. I took the bottle of oil and placed it right on her nether hole and let a few drops fall on it. I pushed the oil in her asshole and her hips bucked in response. As my finger entered her channel she gripped it with her anal muscles. I continued to finger fuck her ass adding more oil as needed and eventually adding a second finger. Satisfied that she was well oiled I straddled her hips and guided my slick cock into her ass. My cock head slipped past the oily sphincter and the spongy head disappeared into her ass. Her anal ring snapped closed behind the cock head and I marveled at the sight before me. I only had the head of my cock in her and she lifted her hips and pushed back obviously wanting more. My cock felt bigger than it ever had as I eased more of it into her anal passage. I watched as it stretched her open and slid easily in her oily hole. I continued my slow penetration until the entire length of my shaft was balls deep in her ass. Rita gasped and grabbed the bed sheets as I hit bottom and then moved her ass in time with my thrusts. I felt my balls tighten just before I came again. There was not much semen but the sensation was just as pleasurable for me. I collapsed on her body and then rolled her to the spoon position with my cock still embedded in her ass. We remained in the spoon position for quite awhile. I think we even dozed and we were awakened when my deflated cock slipped from her ass. Rita rolled toward me and smiled as she whispered. "Kiss me," she said softly. I wrapped my arms around her and we embraced and kissed. We stayed on our sides facing one another kissing and talking for several minutes. Then she shocked me with her next statement. "I can't let you stay the night. The guy I'm living with will be home in the early morning," she told me. I checked the time and saw that I still had two hours to get out of there so I took another shower, dressed and left. Rita was already asleep when I got out of the shower so I left quietly so as not to disturb her. I never ran into or heard from Rita again. I assumed that she was horny that one night and hoped to get lucky. As it turned out we both got lucky. She was a good fuck and loved anal as I did. NUMBER 9 -- BARBARA It was 1983 and the software company I worked for decided to have the user conference in Chicago. I was the Western Region Manager based in the Chicago area and I had responsibility for everything west of the Mississippi River. Barbara the corporate administrator in charge of conference logistics came to Chicago to select the hotel for the conference. She had received several bids from large hotels in the city and she would visit each one while she was in town. She had asked me where to stay and I told her the Westin which used to be the Continental Plaza. The Westin had offered her a complimentary room since she was in charge of booking the conference. Barb arrived on Monday evening and checked in at the Westin. On Tuesday she planned to visit two of the five hotels under consideration. On Wednesday she would visit the other three and then on Thursday she would select one, sign the contract and fly back to Philadelphia. Barb asked me to have dinner with her on Wednesday evening. It was business as usual for me on Monday, Tuesday and Wednesday. On Wednesday afternoon I went into the city and met Barb at the hotel. She wanted to go to a nice restaurant that had a good bar. I took her to Sweetwater's and she loved the place. We had a couple of drinks before dinner and then we had a great meal. Barb got a little tipsy as she drank the wine especially after a couple of cocktails. She got very talkative and shared some things about her life with me. Barb was 36 years old and she was a pleasing looking blonde. One would not say she was pretty but one would admit that she was alluring. She stood at 5'6" and probably weighed no more than 125 pounds. She had nice legs and incredible ass with small breasts. Her ass was her best asset as it stuck out slightly and seemed to beckon to be touched. Barb was married to her current husband for 10 years. She told me that she was sexually active outside her marriage but that she never really had an affair. It was mostly one night stands and it was when she was on the road on company business. She told me that she had a number of encounters with hotel staff and that they would often hand her their business card and offer their services to her. I wondered why she shared this part of her life with me but then I was to find out later that night more about her. I steered the conversation back to the hotel selection for the user conference. Barbara told me how she had the hotels ranked in order of preference and she had selected the Westin as her first choice. I agreed with her on that choice not only because it was a five star hotel but because of its location. It was right off the magnificent mile that was filled with top of the line stores and shops. It was only a few blocks from Oak Street Beach and one block from the Water Tower Place. The theater district and nightlife were short cab rides from the hotel. There would be plenty to do for the spouses that accompanied their partners to the conference. Barbara was glad that I agreed with her selection and supported her choice. 14 Memorable Anal Encounters 02 We had finished our dinner and the wine so I asked her if she would like an after dinner drink, coffee and dessert. Barbara passed and suggested that we have the after dinner drink in her room at the Westin. We took a taxi back to the hotel and went up to her room. They had given her a suite with a well stocked mini bar and everything was complimentary. "Let's get undressed and then have that drink," Barb said catching me off guard. "You want us to get us undressed?" I questioned in confirmation. "Sure, why not? Our clothes are going to come off soon anyway," she replied with a smile. I was all for it as I was anxious to get a look at her naked and check out her curvy ass. I undressed as she did and we watched each other at the same time. Barb smiled when my underwear came off and she saw my cock in its flaccid state hanging between my legs. I anxiously waited until she turned her back to me so that I could see her naked ass. Barb turned to put her clothes on the chair and I was treated to a view of her amazing ass. It was perfectly shaped seemed to reach out toward me. I secretly hoped that she liked anal sex. "I'll have a Baileys," she told me. I got a Baileys for her and a cognac for me and then we reclined in the bed together. We clicked glasses in a toast and sipped our after dinner drinks. "You know I don't usually do this. I mean that I don't sleep with company employees," Barb admitted. "I don't either," I lied. "So we can make an exception this time but I need your promise to be discreet," she stated. "You have my word. I do not tell tales out of school. Our sex lives should be our own business," I assured her. "Good I am glad that you agree," she said and then took another sip of her drink. Barb put her drink down on the nightstand, smiled at me and reached for my cock. "You have a nice cock," she told me just before she slid down and took it in her mouth. I leaned back as her very skilled mouth got me hard within minutes. I put my drink down and put my hands in her silky blonde hair as her head bobbed up and down. Satisfied that I was sufficiently hard, Barb mounted me and lowered her dripping wet pussy onto my cock. She looked me right in the eye as she started to ride me and I knew that she was in desperate need of an orgasm. I reached up and played with her small tits and tweaked her hard nipples as she rode me. Barb's was breathing hard and rapid as she approached her release. I looked into her eyes and I could see the lust in them. Then it happened. "Oh God, oh God, oh, oh, hold me," she screamed as an orgasm of a massive proportion rocked her body. She rode through her orgasm and I felt my cock swimming in her pussy. Barb then collapsed on my chest for several minutes until she composed herself. She then lifted her self off my cock and I heard a distinct sucking sound as my cock was released from her pussy. Barb reached for my cock, wrapped one hand around its girth and looked up at me with those daring blue eyes. She then tilted her head back down and brought her mouth towards my cock. She ran her tongue up its smooth underbelly and I groaned aloud. Holding it with her hand she sank her open mouth down onto my cock. Her lips closed around it and I felt her hot, wet tongue go to work. She sucked me hard and her cheeks hollowed as she worked her head back and forth. I gasped and put my fingers into her soft blonde hair to guide her head back and forth. Barb knew what she was doing as her pace slowly quickened and her right hand worked my shaft. Her left hand cradled my balls and softly stroked them. She then ran her finger along my perineum. Barb took my cock from her mouth and blew on the head of it. I felt her breath cool the saliva on my cock and I clenched my butt in pleasure. My large cock bulged in her firm grip and felt even larger than normal. Barb worked her hand back and forth letting it glide smoothly around my cock then she looked up at me and smiled. She knew the effect she was having on me and she seemed to enjoy every moment of my torment. I moaned again as her tongue snaked forward and tickled the tip of my cock. Her tongue found the pee hole and she licked the pre-cum as it oozed out of my slit. She worked her tongue in circles around the tip of my cock and took my length deeply into her mouth again. I watched as almost the full length of my cock vanished into her mouth. Barb then swirled her tongue around the shaft of my cock that was buried in her mouth. I closed my eyes and groaned in pleasure as her head worked back and forth more quickly clasping my shaft with both hands as her head vigorously bobbed up and down. Her pace was relentless and I held her head gently as I felt my orgasm building in my testicles. This was definitely the best blow job I'd ever had in my life, bar none. Barb allowed my cock to plop out of her mouth again and a thin trail of saliva stretched from my cock to her lips. She smiled again and caught the saliva in her hand as her eyes fixed on my cock. Her hand wrapped tightly around it again and she proceeded to jerk me off me at a steady pace occasionally licking the head of my cock and nibbling it with her teeth. I threw my head back. Closed my eyes and groaned out loud. Barb jerked me off as fast as she could as her hand almost became a blur as it moved up and down my shaft. There was a distinct look of lust in her eyes as she stared at my cock "Are you going to cum for me? Are you close?" she asked in a raspy voice. I just nodded yes since I was very close. Barb then took me back in her mouth and ran her tongue around my shaft again. Then her head bobbed up and down again as she pursed her lips and hallowed her cheeks. That did it for me. "Barb here it cums," I warned and then I grunted as I came in her mouth. Barb took my warning as a signal and she started sucking harder and squeezing my cock with her hand. My eyes closed tight as I ejaculated in her mouth. I felt my cock pulsate as rope after rope of semen shot into her mouth. As the intense sensations passed from my body I relaxed a little and looked down to watch Barb suck every drop from my cock. She was now kissing it, licking up and down the shaft as if she were making love to it. My cock softened in her mouth and she took it in her hand as she licked the final remnants of my ejaculation from the slit. Once she was satisfied that she had emptied my cock she ran her tongue around her kips and swallowed one final time. Barb let out a big sigh and sat up on the bed. We rested for several minutes, sipped our after dinner drinks and chatted easily. Then we began playing with each other again and when I found Barb's G-spot she came again. She held my hand tight to her pussy as she humped it vigorously. Then she stiffened and screamed as another orgasm rocked her. "No one has ever found that spot as quickly as you did," she gasped and then requested, "Fuck me doggy style this time." She rolled over on all fours, put her head down on the bed and raised her curvy ass in the air. I wanted to just drive my cock in her ass but I knew it would be better for her to warm up to it. I still didn't know if she liked anal sex. I knelt behind Barb and slipped my cock into her pussy from behind. I fucked her slowly and then I began to play with her ass. I caressed the shapely globes and teased her anus with my finger. I scooped up some of her pussy juice and rubbed it into her anus. Barb wiggled her ass in response so I took it to the next step. I pulled my cock out of her pussy and ran it up and down the crack of her ass. Then I paused at her nether hole and prodded it gently with my rigid cock. "Oh, where's the Vaseline?" Barb cooed. I knew then she was going to let me have her ass. I hopped out of bed and dashed to the bathroom and quickly located the body lotion supplied by the hotel. Then I got back in bed behind Barb and thoroughly coated her anus with the lotion. I put gobs of lotion on my cock and then added my saliva to it. My cock was as slick as oil and I eased it into her ass. My cock slid in like a hot knife through butter and I buried it to the hilt in her ass. Barb emitted a gasp as my cock slid all the way in on the first thrust. I plowed her asshole and fucked her rapidly in search of my much needed orgasm. She eventually began to move her hips in an attempt to match my thrusts and it was obvious that she was turned on by the anal sex. Barb was gasping and grunting as I began to really pummel her ass. I picked up the pace even more and held to Barb's shapely buttocks as our hips slapped noisily together. She was really into it now and the two of us fucked like maniacs. "Oh yeah that's it, that's the way to fuck my ass. Give it to me, cum in me, cum in my ass," she screamed. We were both sweating from the physical intensity of our butt fucking. I slammed into her as my cock now moved freely in her ass. I felt my orgasm approaching and as much as I wanted to prolong the ass fucking session, I couldn't. My body stiffened and I plunged my cock all the way into her gorgeous ass. Streams of semen shot into her rectum as I seemed to cum continuously for several minutes. "Oh good, I feel it. Fill me up, fill up my ass," she cried out and then her own orgasm hit her, "Oh shit, here it is, I'm cumming!" Her body thrashed around as I held onto her curvy ass cheeks and kept my cock buried in her ass. Her fingers flew over her pussy and clit as my warm seed flooded her anal passage. She then collapsed face down on the bed and my cock slipped from her ass with an audible pop. I knelt over her as my cock dripped the remaining cum on her curvy ass. She wiggled her bottom and squealed in delight. I moved back from Barb and I admired her shapely ass. She looked so sexy that I rubbed her buttocks lovingly and she clenched her ass muscles. She then rolled over on her back and spread her legs for me. "You made me so hot come here and eat my pussy," she pleaded. I climbed on the bed and moved my head between her legs to eat her pussy but first I kissed and licked around the area and her inner thighs. I breathed warm air right on her snatch and she grabbed my head and pulled it to her cunt. I pulled my head back off her pussy and let my fingers trail to her pussy. I lightly rubbed her outer cunt lips and she twitched with each touch. She moaned as her clit responded to the stimulation and slowly exited its hood looking for attention. I placed my fingers on her cunt lips and trapped her clit between them and it became engorged and stood erect. She squirmed in pleasure while I moved her cunt lips up and down on her clit and she shuddered from the extreme arousal. Still moving her cunt lips up and down, I bent down and kissed her clit. She jerked and bucked as my lips touched her upright nub. I drew my head back a bit and again blew air directly onto her clit as she writhed and bucked again, moaning with pleasure. I placed my arms behind her knees and raised her hips up. I put her legs over my shoulders and I lowered my mouth to her pussy and kissed it as though it were her mouth. She groaned with delight as she waited for my next advance. I drew my tongue along her outer labia, up one side and down the other without touching her clit. "Suck it please, please lick it, oh please!" she moaned lustfully. I flicked my tongue across the edges of her pussy as she quivered and seeped her juices from between the lips. I licked the juices from the edges telling her she tasted delicious. She was nearly mad with desire as she begged me to pleasure her with my tongue. I parted her labia with my tongue and licked the insides of her cunt lips, nibbling each one a little and then sucking on them both. She whimpered and moaned when I suddenly plunged my tongue as deep as I could into her pussy. She screamed with delight as my tongue explored the insides of her pussy. Instinctively, she grasped my head and pulled it into her cunt, begging me to lick and suck her. I did not disappoint her as I swirled my tongue around her engorged clit and back into her sopping wet cunt. She was constantly moaning as my lips closed about her clit and sucked her clit in and out of my mouth. Writhing and gyrating she exploded in another powerful orgasm, drenching my face and mouth with her copious juices. She seemed to cum with each spasm of her body. I did not let up sucking her clit and she tried to push my face away as she cried out. "Oh stop, please stop. I can't cum anymore let me rest," she begged. Her body shuddered through yet again another orgasm and she lay there gasping and breathing heavy as her orgasm abated. Finally her orgasm subsided and she embraced me and kissed me. I knew that she could taste her own juices on my lips and I plunged my tongue into her mouth taking her breath away. By now my cock was rock hard again and I moved between her legs. I eased my cock into her sopping wet pussy and she wrapped her legs around my torso. "My, we are horny this evening aren't we?" she asked playfully. "I'm always horny for you," I replied and I began to fuck her gently. Slowly, I moved into her. Barb opened beneath me, enveloping my penis tightly. Her cunt was like a fist as she clenched her vaginal muscles. She squeezed me as I moved within her. She moaned in response, "Your cock feels so good. Fill me up with it." I thrust into her deeply and I felt the head of my cock pressing against her cervix. "Oh Walt," she sighed with her eyes closed. I felt her vagina contract around my cock. She climaxed again with a shudder and a long moan and she urged me on, "Fuck me, I want it so much." I grabbed her hips in my hands and began to thrust in and out as I pounded her pussy. My heavy bloated testicles slapped against her ass as my cock drove into her hot pussy. "Yes, oh yes," she gasped as her body rose to meet me. The bed was now rocking with the force of our fierce, animalistic fucking. Her legs clamped around my waist as she screamed her release. Her pussy grasped my cock, squeezing it and milking it as I fucked her. I moved my hips against hers and buried my cock to the hilt within her. Her quaking pussy erupted into orgasm again as I rocked my cock slowly, grinding the head against her cervix. I felt my orgasm building in my balls and I knew that any second I would be spewing my seed into her womb. I felt my semen travel from my scrotum through my cock as I came deep inside her flooding her waiting warmth with my load. Neither one of us could speak as the pleasure was so intense. I collapsed on her and she wrapped her arms and legs even tighter around my body. I kissed her neck and she sighed aloud then I kissed her on the lips and our tongues dueled with each others briefly. Not wanting to crush her I rolled off her as my cock deflated and slipped from her cum filled cunt. "Stay with in me in my bed tonight," Barb suggested. I woke up Thursday morning lying on my side next to Barb who was also on her side. She was cuddled up in a spoon position with her bottom pushed into my crotch and my morning piss hard-on was tucked between the cheeks of her ass. I reached around and cupped Barb's small firm tits with my hands. Then with one hand I trailed it down her body and found her pussy. I inserted a finger into her quim and diddled her clit until she rolled to her back. Her pussy was soaking wet again as I mounted her and slid my cock into her. Barb just moaned with her eyes closed as I began the ritual of fucking her with my morning hard-on. I fucked her through multiple orgasms as I had done in the past until she begged me to stop and let her rest. I pulled out of her and went into the bathroom with my erect cock pointing the way. "Come back to bed after you go to the bathroom," she told me. I relieved myself and then returned to bed as she had asked. Barb had me lie on my back as she positioned her head near my cock. She then proceeded to give me one of her fantastic blow jobs. I was very turned on and I knew that I would blow my load quickly particularly with Barb's skill at oral sex. "Let me know when you are going to cum," she said and then returned to sucking my cock. I felt my orgasm building from my toes to my cock and I let Barb know that I was really close. She took my cock from her mouth and stroked it with her hand. Her pace quickened as my cock seemed to get harder and bigger. Then with her other hand she cupped my bloated balls and fingered my perineum. That did it and my body stiffened as cum shot out of my cock. Barb kept jerking me off as she watched rope after rope of semen shoot out of my cock and land on my chest and stomach. She kept working my cock until the remaining seed was just oozing from my cock head and trickling into my pubic hair. Barb then sucked the remaining cum from cock, licked off her hand and smacked her lips. "I wanted to watch when you cum," she said almost pleased with herself. "I'll call room service for breakfast and then you can have my ass again if you're up to it. After we eat we can get to work today," Barb said as she swung her shapely legs out of bed. She ordered room service and as promised let me have her ass again. We showered, dressed, ate breakfast at the Westin and then I headed home to change clothes before I went to the office. Barb met with the Westin staff, signed the contract and then flew back to New Jersey. It was set that next year's user conference would be held in Chicago in May. I looked forward to her return to Chicago. Actually as it turned out, Barb and I hooked up several times on my visits to the home office before the user conference and again while she was in Chicago. We were both very discreet and enjoyed our special relationship. I will always remember her sweet ass. NEXT CHAPTER More anal action with Peggy, Lee and Sherry. 14 Memorable Anal Encounters 03 AUTHORS NOTE: I decided to submit stories of my life's anal encounters. Of all the women that I hooked up with over the years, fourteen of them included anal sex. Some of these were affairs that lasted for months and some for years. Others were memorable one night stands. Instead of going in chronological order I ranked the encounters according to the hottest ones beginning at number fourteen and working my way to number one. Over my lifetime dating back to 1959 when I turned 18 years old, I have had hundreds of sexual encounters with over fifty women. Being a leg and ass man, my most memorable encounters included anal sex. Most all of my sexual encounters were pleasant but these involved anal sex. INTRODUCTION My age will range from 29 to 48 during the years 1970 through 1990. The one thing that I pride myself on is staying fit through all those years and even today at age 72. I am 6'0" tall and have always weighed between 205 and 215, my current weight. In the early years I played softball, football and basketball. Eventually I shifted to the individual sports of tennis and golf. I am still an avid downhill skier and SCUBA diver and I am still taking martial arts classes. In addition I make it to the gym at least three days a week and I am a ski instructor at a local ski area in the Midwest. I love to travel and although not fluent, I am very comfortable with the Spanish, Italian, and French languages. I am also currently studying Mandarin Chinese. I enjoy reading and the arts and I am a frequent live theater attendee. I have traveled to Spain, Italy, France and the UK over the years as well as some of the best SCUBA diving spots in the Caribbean and best ski mountains in the U.S. and Europe. Some of my other story submissions to literotica speak to my experiences in other countries and islands as well as at home in the states. I served four years in the Marine Corps and I was honorably discharged in 1963. I will begin the stories with number 14 and work my way up to number 1. Due to the length I have broken the stories up into chapters so that a single submission would not be too lengthy. Also there will be some redundancy in the description of sex acts, after all how could there not be. I had my favorite positions and activities and they were often repeated with different partners. The ranking and dates of the encounters are as follows: 1-Cathleen (1985 -1990) 2-Charlotte (1970-1972), 3-Bonnie (1974), 4-Pamela (1973), 5-Beverly (1977), 6-Sherry (1983), 7-Peggy (1976), 8-Lee (1982), 9-Barbara (1984), 10-Rita (1978), 11-Terri (1979), 12-Susan (1971), 13- Toni (1978), 14-Cindy (1973). NUMBER 8 -- LEE It was 1982 and I was working with a software company in Chicago. I was the Regional Manager and I was helping out the staff with sales calls and qualifying prospects. I received a call from my District Manager in Dallas and he asked if his new tech support person could shadow me for a few days. He felt she would learn more from me visiting prospects than just reading manuals. I agreed and a pretty blonde young woman named Lee was on her way to Chicago. I met Lee at O'Hare airport and we called on a few prospects in the north suburbs. Afterward I gave her a brief driving tour of Chicago and then we stopped for dinner in the hotel restaurant where she was staying. During dinner Lee seemed to feel the effects of the wine. "I shouldn't drink so much wine. It always makes me feel romantic," she whispered across the table. I just smiled at her and then looked at her in a different light. I felt that she was there for the taking. Now I studied her features closely. She had long blonde hair that came down past her shoulders. Her eyes were very blue. Lee was 5'11" and even taller when she wore heels. Tonight she had worn a blue dress that had a slit in the side and every once in awhile her shapely leg would appear. She had nice sized breasts and she was very fit. After dinner we went to her room and I asked if I could join her for an after dinner drink in her room. She snuggled in close wrapping her arm in mine and whispered, "I'd love that." Once in the room we kissed and then peeled the clothes off one another. Lee got in the bed and lay back as I took in her beauty. For a 33 year woman she was in great shape. She had nice legs, a narrow waist, great abs and nice tits. I looked at her pubes and noticed the light blonde tuft of hair above her pussy. I walked over to the bed and sat on the side of it. I stroked Lee's shapely legs and luscious thighs. My hand drifted up to her mound and I felt that she was wet with desire. She smiled at me as I fingered her pussy and licked my fingers clean of her juices. Then she opened her arms and welcomed me into her body for the first time. I slipped between her thighs and slid my hard cock into her quim. Lee uttered an audible gasp as I hit bottom. I began to fuck her slowly and eased my cock almost all the way out of her pussy before plunging it back in. She was lost in the lust of the moment. "Oh that's it fuck me, fuck me slow," she whispered. Just hearing her asking me to fuck her was an incredible turn-on for me and I picked up my pace. Lee threw her hips up at me as if to try and get me deeper in her cunt. I felt my orgasm approaching but I didn't want to cum before she did so I tried to slow down. "No, no don't stop, fuck me faster, I'm so close," Lee begged. I picked up the pace again as we both raced toward our orgasms. I don't know who came first because we were so close but Lee wrapped her long legs around me and humped me for all she was worth as I spurted my seed deep in her womb. We continued to fuck each other until we were drained. I collapsed on top of Lee and she didn't seem to mind my weight as she held me and cried out. "Oh thank you, I was hoping we would do this," she said. I rolled off of Lee and lay next to her on the bed. She smiled at me and then snuggled in closer. We talked for the next several minutes and she told me that she was happy that we got together. She told me that she was drawn to me because I didn't hit on her before. As I lay next to her I caressed her breasts, neck and arms, teasing her skin with my fingernails and tongue. Lee made a low, drawn out sound. Deciding that I'd teased her enough I started on her naked breasts. As I sucked her warm flesh into my mouth and rolled a nipple between my teeth, Lee let out a moan of pleasure. Lee then moved down the bed, gently took hold of my cock and took me into her mouth, rolling my cock around and getting it wet with her saliva, while her hand worked my shaft up and down at the same time. Seconds later, she straddled me. Her hand wrapped around my now slippery cock and I felt the tickle of her pubic hair just before her soft flesh nudged my helmet and then it was suddenly engulfed by the heat and tightness of her pussy. Lee grabbed hold of the top of the head board on either side of my head as I held onto her hips. She rocked her hips back and forth, pressing downwards and working the walls of her pussy as I slid into her further. The next motion of her hips caused her to gasp in pleasure as my full length penetrated her. She began to work up and down, back and forth as she moaned in pleasure. She felt particularly tight in this position and the unhurried pace felt sensuous and wonderful. Lee continued to ride me at a slow, even pace as I relaxed and let her take charge. As she fucked herself on me I could hear the smacking and sucking sound of her pussy as my cock moved around inside her. Her firm medium sized breasts jiggled as Lee picked up the pace. She pushed her hips down until our groins met and then lifted up until just the swollen tip of my cock remained inside her. She seemed to know just how far to move so that my cock never slipped out of her pussy. Her thigh muscles felt firm and tight under my hands as she worked her body on me. The speed of our groins slapping together increased as we fucked faster and harder. We really had our rhythm going now and I thrust up into her as she lowered herself on me. Her pussy contracted around my cock as her eyes fluttered and she emitted a high pitch scream. Lee grabbed onto my shoulders as she rode out her orgasm. I ejaculated into her again flooding her cunt with spunk as she collapsed on top of me. Lee covered my face with kisses and then plunged her tongue into my mouth. As she kissed me she murmured softly into my neck and shoulders. She thanked me over and over as she held herself tightly to me. "Oh my, I haven't cum like that in a while," she sighed and then added, "But I haven't been fucked like that for some time and you came so much." As I lay by her side I noticed that her tits were standing straight up and her aroused nipples were pointing at the ceiling. I tweaked the hard little nubs between my fingers causing her to gasp and quiver. "My breasts are very sensitive," she murmured. I leaned over and kissed her breasts and sucked on her sensitive nipples. I rubbed her firm flat tummy as I sucked on her tits and her rock hard nubs. I was still hard and ready to fuck some more. "Oh I love that it makes me feel so feminine," she cooed. As I sucked her tits and continued to rub her belly, I let my hand drift down to her wet pussy. I ran my fingers through her soaked pubic hair. Lee begged me to let her rest as she was sure that she could not possibly cum again. I rolled her onto her stomach and lifted her hips to a level with my cock as I knelt behind her. I eased my cock into her pussy and began to fuck her doggy style. Lee was content in this position since I was not in contact with her clit. I slammed into her from behind causing her curvy ass cheeks to jiggle. As I fucked her from behind I looked at her tight asshole and wondered if anyone or anything had ever been in there. I scooped up gobs of her pussy juice and smeared it in the crack of her ass spreading around her nether hole. I added saliva to my finger and probed her tight aperture with the tip of my finger. She tensed when she felt my finger probe her asshole. I gathered up more juices and added more saliva as I continued to probe her hole and open her up. I gently pushed a very well lubricated finger into her ass and the tiny aperture opened up to accept the digit. More saliva and more juices greased her asshole sufficiently to allow me to slide my finger all the way into her rectum. Lee knew that I was preparing her ass for my cock when she said, "Please be gentle if you fuck my ass." "Don't worry," I assured her. I eased my cock into her ass and I heard her gasp as I penetrated her. She quickly adjusted to my cock and I soon had a smooth rhythm going. I loved watching my cock slide in and out of her shapely ass as I caressed her lovely buttocks. Now with my in her ass I was approaching another orgasm. I could it build in my balls, travel through my scrotum and splash the insides of her rectum with my warm semen. I flooded her beautiful ass and then pressed forward leaving my cock in her. I stayed in position behind her as she milked my cock with her sphincter. I waited until my cock softened and slipped from her ass before I moved away. Lee flopped forward on the bed and let out a big sigh. I took a quick shower, dressed and headed home. I reminded her that I would pick her up in the morning. Our plans were to go to the office first and then make some afternoon calls. In the morning Lee was in the mood to fuck again so I went to her room, undressed and got in bed with her. We had sex for hours with me finishing up in her magnificent ass. We showered and as we did I fucked her in the ass again. Afterward we dressed and stopped for a light late breakfast. We started out at the office and then we made some more calls together. Lee had a late flight back to Dallas that evening and I dropped her off at the airport after dinner. I never did hook up with Lee again but it had been a wonderful experience just that once. NUMBER 7 -- PEGGY I met Peggy in 1976 when I went to work for a small family held company. Working for a family run company was a mistake but meeting Peggy had its rewards. I only stayed with the family run business for three months and then I accepted a position running a data center for a large computer company. In the three months I was at the small company, I had a memorable affair with Peggy my boss's secretary. I first met Peggy when she greeted me in the reception area on the day of my first interview. When she walked in I thought that she looked like a very sexy young woman. She was wearing a light pink shear blouse with tight white slacks. Peggy was small breasted, almost flat chested but she had solid looking legs. She looked to be about 5'5" tall and couldn't have weighed more than 110 pounds. She had long brown hair and dark brown bedroom eyes. She smiled at me and spoke softly, "Are you Walt?" "Yes I am," I answered. "Hi, I'm Peggy. Please follow me," she said and then she turned to lead me to the Controller's office. I thought about the old cliché, "I'd follow you anywhere," as I walked behind her. I noticed that the back of the blouse was totally see-through and that she was not wearing a bra. Then my eyes drifted down to her fabulous ass framed in her tight white slacks. She was definitely one hot young woman. When we got to the Controller's office I checked out the front of her blouse. There was enough of a pattern on the blouse so that it was difficult to see her small tits through the material. However the darkness of her nipples did contrast with the pink blouse. I accepted the position days later and I was already thinking about Peggy and if she was available. I befriended a colleague named Frank at the office and he was dating a girl named Judy who happened to be a good friend of Peggy's. One Friday, Frank came in and told me that Peggy's date bailed out on her and he asked if I would be interested in going out with the three of them. I jumped at the chance to be with Peggy even though I knew it was somewhat risky since she was my boss's secretary. I picked Peggy up at her place and then drove over to Frank's house; we left my car there and Frank drove. That night the four of us then went out for dinner. Peggy wore a very tight mini skirt that showed off her shapely legs and curvy ass. After dinner we went to this dance club where they had a good DJ. We grabbed a table, got some drinks and danced to songs that we liked. Peggy loved to dance and during the fast songs she really got into it. On a few occasions she moved her body in such a way that it caused her skirt to ride up and her panty covered crotch peeked out. The evening was moving fast and we were having a lot of fun. As it got later we danced to a couple of slow songs before we called it a night. As I was dancing with Peggy she moved her hips side to side across mine. She was a very sexy dancer and I soon had a very noticeable erection. Peggy pressed her loins into mine and smiled at me. "I can see that you enjoy dancing with me," she whispered in my ear as she ran her hand over my crotch. "Yes I do and you seem to bring out the best in me," I whispered back and then tongued her ear. I felt Peggy shiver slightly as my tongue dipped in her ear and then she whispered to me again, "But the best is not out yet, maybe later," she teased. I looked over at Frank and Judy dancing and they were locked in an embrace and a deep kiss. I turned my attention back to Peggy and then kissed her. She returned my kiss enthusiastically and plunged her tongue deep in my mouth. The four of us continued to dance as long as slow songs were playing. When the DJ returned to the faster songs we decided to leave and go back to Frank's house. Frank was driving and Judy sat close to him in the front. Peggy cuddled up to me in the back seat as Frank headed for his house. Peggy and I began to kiss in the back seat and I ran my hands over her upper body. I massaged her firm little tits through her blouse and she gasped in my mouth. Peggy then turned toward me, sat sideways and draped her legs over mine. Her skirt rode up and I could see the white crotch of her panty. I ran my hands over her legs and touched the bare skin above her hose. She trembled slightly but held me tighter and whispered to me. "Take my panties off and play with my pussy," she told me. I was surprised by her request but I knew that I heard her correctly. When she said pussy it really sounded so damn sexy. I moved my hands up under her skirt and grasped the panty waistband. As I tugged them down her shapely legs Peggy lifted her hips slightly. I peeled them all the way down and off her legs. Before I fingered her pussy I just had to feel her firm ass. I reached under her and grabbed both of her firm round ass cheeks in both hands and molded them with my fingers. My cock was straining and was ready to burst through my pants. "You like my ass, don't you?" she whispered. I whispered back, "I love your ass!" I released Peggy's curvy ass and slid one hand between her legs. I touched her pussy and I found it to be sopping wet. My finger entered her easily and she emitted a slight gasp at the penetration. I worked a second finger in her pussy and stroked them in and out. Peggy was going wild and she was breathing deeply into my mouth as we kissed. I let my middle finger slip out of her pussy and touch her anus. Peggy stiffened in my arms and then wiggled her ass as if she was giving me permission to explore her ass. I pushed my moistened middle finger in her asshole and then located her clit with my thumb. I wiggled my finger in her ass and pressed my thumb against her clit. Peggy was bucking her hips slowly against my hand and kissing me deeply. I thought that she might cum any minute but at that moment the car pulled into Frank's driveway. "Okay everyone we're home now," Frank announced. I looked up front just in time to see Judy sit up straight. Apparently she had been playing with and sucking Frank's cock during the ride home. Peggy swung her legs around to sit straight and she adjusted her mini skirt. I handed her panties to her and she quickly put them in her purse. Up front Frank was obviously pulling up his zipper and fixing his trousers after he parked the car. "Who is up for a nightcap?" Frank offered. We all went in the house and gathered in the family room. Frank brought in some cordials and the four of us had a nightcap. It wasn't long before Frank and Judy were necking again but this time they excused themselves quickly and headed up to Frank's bedroom. Peggy was nervous about being in the house with Frank and Judy being right upstairs so I offered to take her to my place. Peggy smiled and told me she would love to see it. We drove to my place and in what seemed like seconds Peggy and I were naked in my bed. Peggy then lay on her back, splayed her legs and pulled back the folds of her vagina. "Here eat my pussy, please eat my pussy," she pleaded. I rolled over and got between her legs. I put her thighs on my shoulders and lowered my mouth to her pussy. I took one slow lick as I flattened my tongue on Peggy's mound. It felt so smooth and warm and I knew I had achieved the desired effect from her moan I know that Peggy enjoyed it. I enjoyed the taste of her and I kept licking and eating her. I pointed my tongue and burrowed into her pussy as it parted her labia my tongue was rewarded with the exquisite taste of her juice. Peggy was obviously enjoying what I was doing as she reached down with both hands and spread herself wide making it so much easier for my tongue to explore her pussy. My tongue explored all of her as my mind took notes of what seemed to turn her on. Peggy was breathing rapidly and she moaned softly whenever I got near her hard pearl. As I searched out her hard clit still just barely hidden she tensed and began to quiver. After I felt like I had teased her opening as much as I could with my tongue it was time to see her reaction when my tongue finally touched her sensitive clit. 14 Memorable Anal Encounters 03 Peggy went wild and started bucking and moaning loudly. She let go of her own fleshy hood and pulled my head to her pussy as she cried out in ecstasy. I sucked her clit as deep in my mouth as I could and Peggy humped my face for all she was worth. I was excited that I was able to get her that excited and I sucked harder and played with her wonderful clit with my lips, tongue and teeth. I don't know exactly how many times Peggy came but she finally pushed me away as she collapsed on the bed, her body in spasms. I lay next to her and stroked her body my hands moved freely over her firm small tits and pussy mound. I tweaked her hard little nubs as they pointed straight out from her breasts. She rolled toward me and embraced me and yelled for me to hold her tight. "Hold me, oh please hold me," she pleaded as her orgasms and spasms continued. As we lay there for awhile talking, Peggy started stroking my cock. Peggy added some saliva from her mouth as she kept stroking my cock. Next Peggy straddled my body and lowered herself onto me as she held my tool and aimed it at her vagina. My hard cock slid easily into her womb and she emitted a small gasp as it filled her hole. Peggy rocked back and forth on top of me as I held on to her curvy ass. I stroked her ass cheeks and molded her firm buttocks in my hands as she picked up the pace fucking herself with my dick. Peggy started moaning as she fucked faster and faster. I sensed her pending orgasm and then she yelled out. "I am going to explode. Oh, Oh hold me, please hold me tight," she screamed. Peggy collapsed on top of me her body quivering from the intensity of her orgasm. I could feel her juices coating my cock as it remained buried in her womb. I too exploded with my first load of the night and I flooded her pussy with my semen. It took a few minutes for her to regain her composure and she just lay on me and cooed. Eventually she rolled off of me and lay on her back next to me. I was still hard so I rolled over on her pushing my cock back into her pussy. I fucked her until she pleaded with me to give her pussy a rest. I pulled out of Peggy and then rolled her over on all fours. I slipped my cock back into her pussy and pounded her from behind. I loved looking at her shapely ass as I fucked her and I even thought about fucking her in the ass. However I didn't want to push her too fast so I resolved myself to focus on her pussy. I massaged Peggy's beautiful ass I fucked her doggy style until I came in her pussy for a second time. Peggy had her head turned to the side and emitted soft sounding murmurs as I emptied my balls into her twat. I pulled my softening cock from her and then flopped down next to her on the bed. "I think I need to get cleaned up and dressed. I have an appointment in the morning," she said and then asked. "May I use your bathroom?" "Of course, in fact I'll shower with you," I replied. We both showered together and washed each other but avoided having anymore sex that night. Afterward we got dressed and I drove Peggy home. I wondered what type of appointment that she had on a Saturday morning that she couldn't cancel but I never asked her. I was pleased with the way the evening had turned out and I hoped that there would be more. SATURDAY SURPRISE I was sitting in the living room when the doorbell rang and for some reason I expected it to be Frank. I was wrong but pleasantly surprised when it was Peggy. I invited Peggy in for coffee and she willingly accepted. We went into the apartment and I pored us both a cup of coffee. We sat at my kitchen table sipping coffee and chatting for several minutes. She decided to come and see me after her appointment that morning as my apartment was close by. We chatted for awhile and then I though to ask her if she would like to hang out that day. "Peggy is there anything in particular that you would like to do today? Have lunch?" I offered. She smiled demurely and blushed slightly when she replied, "I would like for us to make love before anything else." "I want us to undress each other and I want to undress you first," she added. Undressing me first would be easy since I was only wearing sweats. Peggy stood up from the chair and walked over to me. Then she pulled my sweat shirt up and off my body. I stood up as she dropped to her knees in front of me to lower my sweat pants but first she removed my athletic shoes and socks. Peggy then took hold of the sweat pant waistband and slowly pulled them down my legs. By this time I had an erection and it sprung out at her as she lowered my pants. My cock dangled in front of her face as she removed my sweat pants from me one leg at a time. I stood completely naked in front of her with my cock just inches from her face. Peggy took my cock in her mouth and sucked it gently. She licked all around it and ran her tongue up and down the shaft. Peggy was a very accomplished cocksucker and I knew that I would soon blow my load. She sucked me deep into her mouth and swirled her tongue around the shaft of my cock. I felt my orgasm building and I warned her that I was going to cum soon. "I am going to cum soon Peggy," I cautioned. She took her mouth of my cock and looked up at me with those deep brown eyes and replied, "I want you to cum in my mouth I want to taste you Walt." Peggy returned her mouth to my cock and resumed sucking it until I exploded in her mouth. She continued to suck my cock and swallow every drop until my cock was drained dry. "Oh Walt I love your cum. It is so tasty and so much of it," Peggy sighed as she licked her lips. Peggy then stood up still fully clothed and lifted her face up to me to be kissed. I kissed her and held her in my arms and then I began to undress her. I dropped to my knees, unbuckled her belt and unfastened her jeans. I pulled the jeans down her legs stopping to remove her shoes and anklets. Then I pulled her jeans all the way down and off her shapely legs. I then took hold of her panties and slowly peeled them down and off her legs. Peggy was trembling slightly and had goose bumps on her skin. I held her panties up to my nose and inhaled the smell of her femininity. Peggy gasped at the action. I reached behind Peggy and grasped her firm shapely ass in both my hands and pulled her toward me. She gasped again as I kissed her loins and fondled her ass cheeks. I could smell her sweet sex but I held off on licking her pussy. I stood back up and I lifted Peggy's sweater up and removed it from her body. Then I reached behind her and unhooked her bra. I was beginning to harden again and my semi-erect cock brushed against her thighs. I slid the bra straps slowly down her arms baring her small firm breasts. Her nipples were rock hard and I couldn't resist tweaking them a little which caused Peggy to moan softly. I then turned her around so that her back was to me and I reached around and cupped her firm tits in my hands. I played with her tits and nipples as I kissed the back of her neck. My cock was now fully erect again and it brushed against her buttocks as I fondled her. I started a slow gradual descent down the back of her body kissing her neck, shoulders and back until I knelt behind her. When I reached her buttocks I planted kisses on both ass cheeks and tickled her crack with my tongue. Peggy couldn't take anymore of my teasing so she turned her body toward me, grasped my head in both hands and pulled me against her pubes. I found her pussy with my tongue and I grabbed both of her ass cheeks as I began to lick her pussy. Peggy gasped aloud as my tongue found her clit and she held my head tightly as she experienced a mild orgasm. Her body shook and she seemed to hold onto me for balance. "Can we go to your bedroom?" she asked breathlessly. I guided Peggy into my bedroom and over to my bed. She immediately splayed her legs and welcomed me back to her pussy. I burrowed my tongue as deep into her as I could and then I just sort of licked and sucked my way up. When I got to her clit I used the very tip of my tongue to tickle it. I flicked my tongue over it once and then used the tip to explore the folds of flesh on either side of it. Peggy was now moaning and she arched herself so that her clit stuck out even further like a little cock. I licked it once more before I took it between my teeth and gently nibbled it. Peggy went wild and started bucking and moaning loudly. She pulled my head to her pussy as she cried out in ecstasy. I sucked her clit as deep in my mouth as I could and Peggy humped my face for all she was worth. I was pleased that I was able to get her that excited and I sucked harder and played with her wonderful clit with my lips, tongue and teeth. I don't know exactly how many times Peggy came but she finally begged me to stop as she collapsed on the bed, her body in spasms. I was not done with her however so I eased my dick into her pussy and began to fuck her slowly. Soon my cock was sliding easily in and out of her and we picked up the pace. Peggy wrapped her arms around my back and her legs around the back of my legs. She arched her back as she humped me hard and fast and I made sure that my cock stayed in contact with her clit as I plowed her cunt. We fucked hard and long working ourselves toward an exhaustive state. I could feel my orgasm building but I did not want to cum before Peggy and I was relieved when I felt her tense up. "Walt, hold me, hold me, I'm coming, oh, oh, oh" Peggy screamed as she reached her crescendo! She tensed up wrapping her arms around my back and her legs around the back of my legs in a vice like grip. I held her trembling body tight and I could feel her drench my cock with her pussy juice just before my own intense orgasm. I could feel it building in my balls and then I exploded filling her with my man seed. It seemed endless as I fired round after round of hot cum into her pussy. I remained still with my cock still in Peggy's pussy as she uttered unintelligent moans and sounds and her body quivered. Her vagina muscles were involuntarily squeezing and releasing my cock, milking all the juice out of it. My deflated cock slipped from her vagina and she flinched as cool air touched her opening. "Oh that was incredible. You are a very good lover, Walt," she sighed. "Well you are too and I really enjoy making love to you," I replied. "I need to rest for awhile, my body aches so," she said softly. "I'll tell you what, let's take a shower," I suggested. Peggy and I showered together and I massaged her firm body as we washed. As I washed her I paid a lot of attention to her ass. As I ran my hands between her legs washing her pussy and her bottom, I slipped a very soapy middle finger into her asshole. Peggy gasped at first but then she just wiggled her bottom and smiled at me. I covered her body with shower gel telling her that it would help soothe her muscles. I also put shower gel in her ass and pushed my finger back in her bung hole. After showering we dried each other and then I gave Peggy a sweat shirt to wear. She looked so sexy with the sweat shirt just covering her pussy and ass with her shapely legs on display that I felt my cock stir again. "Walter can we go back to your bed now?" she asked in a sultry tone. "Of course we can," I told her. As we walked to the bedroom I watched Peggy with her shapely legs below the sweat shirt. I could also see the slight curve to her ass. I felt my loins stir again as we approached the bedroom. Once inside Peggy stripped off the sweat shirt and flopped down on my bed face down. At this point I was anxious to get at her ass all the while wondering if she would let me fuck her in the ass. I moved her to all fours with her ass elevated and she placed her head on the mattress turned to one side so she could see me. I started playing with her pussy and her curvy ass lubricating her asshole with her own cunt juice. Then I grabbed the lotion from my bedside and put an ample amount in her asshole. Peggy moaned and cooed as I fingered her pussy and her asshole simultaneously. I tired to get her asshole slick enough so that I could fuck her ass. When Peggy didn't reject my probing I realized that she was going to let me fuck her in the ass. I put an ample of amount of lotion in her asshole coating the tiny puckered opening of her anus and lubricating the rim. I added my saliva to my lotion covered cock and nestled my dick against the entrance of her rectum momentarily before easing it inside her ass. I always found that Keri body lotion and saliva will make my cock as slippery as possible. I could feel my cock struggle to stretch the resistant muscles. My dick head burrowed in and her rigid passageway soon yielded to the determined action of my cock. Peggy moaned as my penis filled her hole. "Go slowly at first," she said sexily and then added, "Not too deep at first and then deeper." I fucked her with long and deliberate strokes until my cock was sliding easily back and forth in her ass. I caressed her shapely buttocks as I watched my pecker move in and out of her rectum worming around inside of her curvy ass. I caressed her small tits and tweaked her nipples as I leaned over her body and whispered in her ear, "Peggy you have a hot ass, I love fucking you in your hot ass." My hands freely roamed her body and I pulled her hips drawing her backwards impaling her on my inflated member. I reached for her pussy to finger fuck her and diddle her clit but I found Peggy's hand already buried in her womb. She was frigging herself frantically working herself toward an orgasm. Suddenly I felt my cock inside her ass swell up and I started pumping faster. Within minutes I knew that Peggy felt the warm fluid being squirted inside her anus and she immediately started to cum herself. Her cunt walls convulsed around her own hand fucking her cunt as her anal muscles squeezed every drop from my spurting cock. I grunted as my whole body became stiff and I slammed my cock harder into her. Peggy writhed around and her body arched off the bed as a climax of massive proportion tore through her loins. My cock slipped from her ass with an audible pop and I flopped down on the bed next to her. She surprised me when she covered my cock with her mouth and sucked any remaining cum from my tool. The both of us were exhausted and Peggy curled up in my arms. The two of us dozed off for quite awhile and then finally woke up after lunch time. Peggy and I then had a late lunch in the apartment. We sat around naked as we ate and chatted as it was the most natural thing in the world. After lunch I offered Peggy a massage which she gladly accepted. I had her lay face down on my bed and I worked her back, legs and buttocks. Not so surprisingly I got an erection as I massaged and fingered her ass again. I came again when I fucked her ass and after the ass fuck I rolled Peggy over on her back and continued the massage this time working her tits, abs, legs and pubes. I finished her off with another thorough pussy eating which had her screaming my name and humping my face with her volcanic orgasm. Peggy and I continued to see each other but I also learned that she was very sexually active and she was seeing a number of other guys. Peggy loved getting fucked in the ass and she taught me her favorite position. She liked to be kneeling on the bed straight up with me behind her with my cock stuffed up her ass. She had me guide her hand to her pussy and hold it there while she rubbed her clit and with my other hand I fondled her tits and hard nipples. Peggy would cream her own hand and I would cum in her ass filling her rectum with a massive load. After my short three months with the company I left town for a bigger and better job. I never saw Peggy again but it had been an adventurous three months. NUMBER 6 -- SHERRY My best friend Ken and I went skiing for a week every year in Colorado. In 1983 we went to Aspen and stayed in a condo near Snowmass. Ken would always invite some girl that he had fucked before to join him on the trip. This year a woman named Toni showed up the second day that we were there. Toni was nice enough even though she seemed a little shy. I assumed she was slightly embarrassed that I was in the other bedroom while Ken was banging her at night. Toni was a decent skier and she didn't hold us back. The three of us enjoyed our day on the slopes and our Après Ski. One day we stopped at one bar in Snowmass and there was a really good band there. That's when I met Sherry. She was standing alone near the bar when I asked her to dance. She smiled and accepted and we hit the dance floor and stayed out for five songs. "I really need to rest a minute. The altitude is getting to me," Sherry told me after the fifth song. "Sure, would you like to join us?" I asked pointing to the table we were sitting. Sherry accepted the invitation and joined Ken, Toni and I at the table. Introductions were made and we enjoyed the rest of the afternoon together. Sherry was staying at Snowmass for two days and then heading up to Vail to see some friends there. Sherry was a strawberry blonde with a solid figure. She was about 5'6" and I guessed about 140 pounds. She was solid as a rock and had big tits. Her hips and thighs were full but you could tell she was in shape. The three of us closed the Après Ski bar and then agreed to ski together tomorrow. Sherry said goodnight to us and that she would see us tomorrow. Ken, Toni and I went to dinner and then returned to our condo. It didn't take long for Ken and Toni to go to their bedroom and then I decided to watch TV in my bedroom. The next day the four of us skied together and had a great time. Sherry was a very accomplished skier and was probably the best of the four of us. After skiing we all showered dressed and went to dinner in Aspen. Following dinner we found a place to dance and party and we had a good time although there was something funny about Toni that day. I sensed that Toni was jealous of Sherry being a better skier and dancer. It's funny how women can get that way at times. The four of us went back to our condo where Sherry had left her car. I invited Sherry in and I spotted the look of disdain on Toni's face. Sherry accepted and came in for a nightcap. Toni seemed uncomfortable with Sherry in the room so she said goodnight and went into the bedroom. Ken followed her shortly leaving Sherry and me together. We sat on the sofa together with our feet up on the coffee table looking at the fire. It was a romantic setting and Sherry cuddled up to me. I put my arm around her and soon we were kissing and petting. I started to take of her sweater but she stopped me. "Can we go into your bedroom? She whispered. I nodded and whispered, "Yes." We walked into the bedroom and I closed the door. I turned on the small light in the room so that we could see. The room was dimly lit but we could see each other very well. "I want us to undress each other and I want to undress you first," she whispered. I wasn't surprised that she wanted to do that because she was the fourth girl that had used that approach. I was all for it as I liked being undressed by a hot chick. Sherry walked over to me and then she pulled my shirt up and off my body. I stood up as she dropped to her knees in front of me to lower my pants and underwear but first she removed my shoes and socks. Sherry then took hold of the underwear waistband and slowly pulled them down my legs. By this time I had an erection and it sprung out at her as she lowered my briefs. My cock dangled in front of her face as she removed my briefs from me one leg at a time. I stood completely naked in front of her with my cock just inches from her face. Sherry took my cock in her mouth and sucked it gently. She licked all around it and ran her tongue up and down the shaft. Sherry was a very accomplished cocksucker and I knew that I would soon blow my load. She sucked me deep into her mouth and swirled her tongue around the shaft of my cock. I felt my orgasm building and I warned her that I was going to cum. 14 Memorable Anal Encounters 03 "I am going to cum soon Sherry," I cautioned. She took her mouth of my cock and looked up at me with those deep brown eyes and replied, "Okay, undress me now." Sherry stood up still fully clothed and lifted her face up to me to be kissed. I kissed her and held her in my arms and then I began to undress her. I dropped to my knees, unbuckled her belt and unfastened her jeans. I pulled the jeans down her legs stopping to remove her shoes and anklets. Then I pulled her jeans all the way down and off her shapely legs. I then took hold of her panties and slowly peeled them down and off her legs. Sherry was trembling slightly and had goose bumps on her skin. I held her panties up to my nose and inhaled the smell of her femininity. Sherry gasped at the action. I reached behind Sherry and grasped her firm shapely ass in both my hands and pulled her toward me. She gasped again as I kissed her loins and fondled her ass cheeks. I could smell her sweet sex but I held off on licking her pussy. I stood back up and I lifted Sherry's sweater up and removed it from her body. Then I reached behind her and unhooked her bra. I was beginning to harden again and my semi-erect cock brushed against her thighs. I slid the bra straps slowly down her arms baring her large firm breasts. Her nipples were rock hard and I couldn't resist tweaking them a little which caused Sherry to moan softly. I then turned her around so that her back was to me and I reached around and cupped her firm tits in my hands. I played with her tits and nipples as I kissed the back of her neck. My cock was now fully erect again and it brushed against her buttocks as I fondled her. I started a slow gradual descent down the back of her body kissing her neck, shoulders and back until I knelt behind her. When I reached her buttocks I planted kisses on both ass cheeks and tickled her crack with my tongue. Sherry couldn't take anymore of my teasing so she turned her body toward me, grasped my head in both hands and pulled me against her pubes. I found her pussy with my tongue and I grabbed both of her ass cheeks as I began to lick her pussy. Sherry gasped aloud as my tongue found her clit and she held my head tightly as she experienced a mild orgasm. Her body shook and she seemed to hold onto me for balance. I guided Sherry over to the bed and she immediately splayed her legs and welcomed me back to her pussy. I eased my dick into her pussy and began to fuck her slowly. Soon my cock was sliding easily in and out of her and we picked up the pace. Sherry wrapped her arms around my back and her legs around the back of my legs. She arched her back as she humped me hard and fast and I made sure that my cock stayed in contact with her clit as I plowed her cunt. We fucked hard and long working ourselves toward an exhaustive state. I did not want to cum as I wanted to fuck her silly. I was relieved when I felt her tense up. "Walt, hold me, hold me, I'm coming, oh, oh, oh" Sherry said louder than she wanted as she reached her crescendo! She tensed up wrapping her arms around my back and her legs around the back of my legs in a vice like grip. I held her trembling body tight and I could feel her drench my cock with her pussy juice. I remained still with my cock still in Sherry's pussy as she uttered unintelligent moans and sounds and her body quivered. Her vagina muscles were involuntarily squeezing and releasing my cock. My cock slipped from her vagina and she flinched as cool air touched her opening. "Oh that was incredible. You are a very good lover, Walt," she sighed. "Well you are too and I really enjoy you," I replied. We rested for awhile and at this point I was anxious to get at her ass all the while wondering if she would let me fuck her in the ass. I moved her to all fours with her ass elevated and she placed her head on the mattress turned to one side so she could see me. I started playing with her pussy and her curvy ass lubricating her asshole with her own cunt juice. Then I grabbed some lotion and put an ample amount in her asshole. Sherry moaned and cooed as I fingered her pussy and her asshole simultaneously. I tired to get her asshole slick enough so that I could fuck her ass. "What do you want?" she asked. I didn't answer her but instead I put an ample of amount of lotion in her asshole coating the tiny puckered opening of her anus and lubricating the rim. I added my saliva to my lotion covered cock and nestled my dick against the entrance of her rectum momentarily before easing it inside her ass. I always found that body lotion and saliva will make my cock as slippery as possible. I could feel my cock struggle to stretch the resistant muscles. My dick head burrowed in and her rigid passageway soon yielded to the determined action of my cock. Sherry moaned as my penis filled her hole. I fucked her with long and deliberate strokes until my cock was sliding easily back and forth in her ass. I caressed her shapely buttocks as I watched my penis move in and out of her rectum worming around inside of her curvy ass. For some reason I looked at the wall and I saw a reflection in the mirror on the wall. It was Toni. She had opened my bedroom door far enough to see and she was watching me fuck Sherry in the ass. I don't know how long Toni had been watching us but I didn't care as I returned my attention to Sherry. I caressed her big tits and tweaked her nipples as I leaned over her body and said loud enough for Toni to hear, "Sherry you have a hot ass, I love fucking you in your hot ass." My hands freely roamed her body and I pulled on her hips drawing her backwards impaling her further on my inflated member. I reached for her pussy to finger fuck her and diddle her clit but I found Sherry's hand already buried in her cunt. She was frigging herself frantically working herself toward an orgasm. Suddenly I felt my cock inside her ass swell up and I started pumping faster. Within minutes I knew that Sherry felt the warm fluid being squirted inside her anus and she immediately started to cum herself. Her cunt walls convulsed around her own hand fucking her cunt as her anal muscles squeezed every drop from my spurting cock. I grunted as my whole body became stiff and I slammed my cock harder into her. Sherry writhed around and her body arched off the bed as a climax of massive proportion tore through her loins. My cock slipped from her ass with an audible pop and I flopped down on the bed next to her. She surprised me when she covered my cock with her mouth and sucked any remaining cum from my tool. The both of us were exhausted and Sherry curled up in my arms. I looked toward the door and it was closed again. The two of us then dozed off. When I woke up in the morning Sherry was gone. She left me a note reminding me that she was headed up to Vail and thanked me for a great time together. Normally I would have loved to fuck Sherry with my morning piss hard-on but that day I was happy to sleep in. NEXT CHAPTER Anal sex with Beverly and Pamela. 14 Memorable Anal Encounters 04 AUTHORS NOTE: I decided to submit stories of my life's anal encounters. Of all the women that I hooked up with over the years, fourteen of them included anal sex. Some of these were affairs that lasted for months and some for years. Others were memorable one night stands. Instead of going in chronological order I ranked the encounters according to the hottest ones beginning at number fourteen and working my way to number one. Over my lifetime dating back to 1959 when I turned 18 years old, I have had hundreds of sexual encounters with over fifty women. Being a leg and ass man, my most memorable encounters included anal sex. Most all of my sexual encounters were pleasant but these involved anal sex. INTRODUCTION My age will range from 29 to 48 during the years 1970 through 1990. The one thing that I pride myself on is staying fit through all those years and even today at age 72. I am 6'0" tall and have always weighed between 205 and 215, my current weight. In the early years I played softball, football and basketball. Eventually I shifted to the individual sports of tennis and golf. I am still an avid downhill skier and SCUBA diver and I am still taking martial arts classes. In addition I make it to the gym at least three days a week and I am a ski instructor at a local ski area in the Midwest. I love to travel and although not fluent, I am very comfortable with the Spanish, Italian, and French languages. I am also currently studying Mandarin Chinese. I enjoy reading and the arts and I am a frequent live theater attendee. I have traveled to Spain, Italy, France and the UK over the years as well as some of the best SCUBA diving spots in the Caribbean and best ski mountains in the U.S. and Europe. Some of my other story submissions to literotica speak to my experiences in other countries and islands as well as at home in the states. I served four years in the Marine Corps and I was honorably discharged in 1963. I will begin the stories with number 14 and work my way up to number 1. Due to the length I have broken the stories up into chapters so that a single submission would not be too lengthy. Also there will be some redundancy in the description of sex acts, after all how could there not be. I had my favorite positions and activities and they were often repeated with different partners. The ranking and dates of the encounters are as follows: 1-Cathleen (1985 -1990) 2-Charlotte (1970-1972), 3-Bonnie (1974), 4-Pamela (1973), 5-Beverly (1977), 6-Sherry (1983), 7-Peggy (1976), 8-Lee (1982), 9-Barbara (1984), 10-Rita (1978), 11-Terri (1979), 12-Susan (1971), 13- Toni (1978), 14-Cindy (1973). NUMBER 5 -- BEVERLY In 1977 I decided to become a certified SCUBA diver. I had dived when in the Marine Corps but my last dives were in 1962. I did my classroom and swimming pool work in the Midwest and received a referral letter form the SCUBA school so that I could do my open water test in the Cayman Islands. There was another student in my class named Beverly. I relaxed on the beach that afternoon after completing my certification and checked out the hot bikini clad bodies that were already spoken for. Late afternoon, I showered dressed and headed to the bar. Shortly after 5:00 PM Beverly and a couple of dive instructors entered the bar. Beverly spotted me and she and the instructors made their way over to me. The instructors congratulated me and Beverly on our certifications and I bought the first round of drinks. In fact I bought all the drinks that evening but at least the guys didn't stay that long. I studied Beverly closer that evening and I liked what I saw. It must have been a combination of the beer, atmosphere and the fact that there were not any available single women to my liking at the resort. Also Beverly's ass looked good in her tight shorts and I wondered if she liked anal sex. Beverly had a good sense of humor and the more she drank the funnier she became. I sensed that she was out for a good time that evening. She told me a funny story that opened the door for me. "One night Rory and I, that's my boyfriend back home in the UK, were sitting around naked drinking beers. I felt this awful sting on my ass. I yelled and smacked at something that bit me," Beverly began. "Then Rory asks, what happened? I tell him that something bit me on my ass and he says let's have a look. So I roll over and show him the bite on my bottom and he says something bit you on your bum. So I say what do you think I just said?" Beverly told me laughing all the while. She had me laughing as much at her delivery as the story itself. Beverly then continued, "So Rory keeps staring at my bum as if he hasn't seen it before. So I say are you going to keep staring at my bum all night?" Beverly said breaking into laughter once again. I was laughing just as hard as she went on with the story. "So anyway Rory says we better see the doctor because the swelling was getting worse. We hop in the car and drive over to the emergency room. The doctor comes in and asks what the problem is and I tell him that a spider bit me on my bum. He says let's have a look so I roll over and show him my bottom. Then the fucking genius doctor says it looks like something bit you on your bum," Beverly manages to get out laughing hysterically. At this point I am in stitches as well and we are both laughing out loud and Beverly continues, "So, so, I say to the doctor, that's what I told you. The doctor kept staring at my bum and I asked him if he was going to do anything except stare at my ass." Beverly had tears in her eyes from laughing so hard and I was splitting a gut again more from her delivery of the story with her accent. "So what do you think the doctor does? He goes and gets some more medical staff to come in and look at my ass. So now I laying there with five people looking at my bum, but not a one of them are doing anything. So I ask them if they think that I just came down to the emergency room to show you my bum. They all start laughing and I start laughing and Rory is laughing. So now I am on the exam table with my ass in the air with five people looking at it and we are all laughing," Beverly leaned into me and roared out loud. I put my arm around her as we laughed and then I said, "Well you have to forgive them because after all you have a nice ass." Beverly then looked up at me and she was not laughing now. I was afraid that I had offended her but she leaned in and whispered, "Do you really think that I have a nice ass?" "Absolutely, of course I have only seen the shape of it in your bathing suit or shorts. I haven't been as fortunate as the medical staff to see it bare," I replied. "Would you like to see it?" Beverly asked as she moved her hand over my thigh. "Can I count on you to be discreet?" "Yes to both questions," I whispered in her ear. "Let's go to your room but we can't be seen walking in there together," she told me. I told her my room number and she walked out of the bar first. I settled my tab and then finished my beer before I left. I walked over to the building where my room was and as I did Beverly appeared out of the shadows. She had waited until I had my key in my hand and I was close to the room. I opened the door and she quickly ducked inside. Beverly made a bee line for the bedroom shedding her clothes along the way. She hopped in bed totally naked as I finished removing my clothes. Beverly was ready as was I so there was no need for foreplay. I slipped right between her thighs and my cock slid into her wet pussy like a hot knife through butter. Beverly moaned as my cock entered her cunt and she wrapped her arms and legs around me as I went deep into her. We fucked slowly at first and then picked up the pace. Beverly had a mild orgasm along the way to a massive more intense one. Her body rocked and gyrated as she screamed in ecstasy and it was all I could do to hold on as she bucked up at me. Then I felt my surge and I drilled deep into her pussy just before I unleashed a massive cum load. I felt my cum shoot out of my cock deep into her womb and Beverly held me tighter as I came in her. We stayed together for several minutes with my cock buried deep in her pussy and her arms and legs still holding me tight. Beverly and I separated and I rolled over on my back. She surprised me when she moved back down and took my cock in her mouth. Within minutes she had me rock hard proving that she was an accomplished cock sucker. I was anxious to get at her ass all the while wondering if she would let me fuck her in the ass. I moved her to all fours with her ass elevated and she placed her head on the mattress turned to one side so she could see me. I started playing with her pussy and her curvy ass lubricating her asshole with her own cunt juice. Beverly moaned and cooed as I fingered her pussy and her asshole simultaneously. I tired to get her asshole wet enough with her juices and my saliva so that I could fuck her ass. I knelt behind her and tried to insert my cock in her ass but it just wouldn't go. Afraid of hurting her I tried more pussy juice and saliva for lubrication but to no avail. My cock of 7+ inches long and 5 inches around just wouldn't go. There are times when it feels bigger and this was one of those times. I was fingering Beverly's ass when she spoke. "You are going to need some cream to get that thing in my ass," she whispered. I got off the bed to retrieve the lotion from the bathroom. As I did I realized that Beverly was going to let me fuck her in the ass. I returned to the bed and put an ample of amount of lotion in her asshole coating the tiny puckered opening of her anus and lubricating the rim. I added my saliva to my lotion covered cock and nestled my dick against the entrance of her rectum momentarily before easing it inside her ass. I could feel my cock struggle to stretch the resistant muscles. My dick head burrowed in and her rigid passageway soon yielded to the determined action of my cock. Beverly moaned as my penis filled her hole. "Go slowly at first you're big," she said sexily. I fucked her with long and deliberate strokes until my cock was sliding easily in and out of her ass. I caressed her shapely buttocks as I watched my penis move in and out of her rectum worming around inside of her curvy ass. I caressed her small tits and tweaked her nipples as I leaned over her body and whispered in her ear. "You know Beverly I can see why all those people were looking at your bum. You have a very hot ass and I love fucking you in your hot ass." My hands freely roamed her body and I pulled her hips drawing her backwards impaling her on my inflated member. I reached for her pussy to finger fuck her and diddle her clit but I found Beverly's hand already buried in her womb. Suddenly I felt my cock inside her ass swell up and I started pumping faster. Within minutes I knew that Beverly felt the warm fluid being squirted inside her anus and she immediately started to cum herself. I grunted as my whole body became stiff and I slammed my cock harder into her. Beverly writhed around and her body arched off the bed as a climax of massive proportion tore through her loins. My cock slipped from her ass with an audible pop and I flopped down on the bed next to her. Beverly then lay on her back, splayed her legs and pulled back the folds of her vagina. "Here eat my pussy, please eat my pussy," she pleaded, "I need to cum again." I rolled over and got between her legs and blocked out that fact that I had cum in her before. I put her thighs on my shoulders and lowered my mouth to her pussy. I took one slow lick as I flattened my tongue on Beverly's mound. It felt so smooth and warm and I knew I had achieved the desired effect from her moan I know that Beverly enjoyed it. I enjoyed the taste of her and I kept licking and eating her. I pointed my tongue and burrowed into her pussy as it parted her labia my tongue was rewarded with the exquisite taste of her juice. Soon I was lapping up as much as I could as fast as I could. Beverly went wild and started bucking and moaning loudly. She let go of her own fleshy hood and pulled my head to her pussy as she cried out in ecstasy. I sucked her clit as deep in my mouth as I could and Beverly humped my face for all she was worth. I was thrilled that I was able to get her that excited and I sucked harder and played with her wonderful clit with my lips, tongue and teeth. I don't know exactly how many times Beverly came but finally she collapsed on the bed, her body in spasms. I lay next to her and stroked her body my hands moved freely over her tits and pussy mound. She rolled toward me and embraced me and yelled for me to hold her tight. "Hold me, oh please hold me," she pleaded as her orgasm and spasms subsided. I had never seen anyone cum that hard before and I was briefly worried that she had injured herself. My fears were short lived when she finally calmed down and spoke to me. "That was incredible I haven't cum like that in a long time. You really know how to eat pussy," she said with a sigh. We lay there for awhile making small talk and then Beverly started stroking my cock. Now at the age of 36 it was very unusual for me to cum more than twice in a fuck session, particularly after having a couple of drinks. In fact I usually could stay hard for a long time before my second cum which allowed me to pleasure my partner thoroughly before achieving my own orgasm. Beverly added some body lotion as she kept stroking my cock and soon had me hard again. "I like playing with your cock. You have a big cock," she told me. "It's not that big," I replied although I was very comfortable with my manhood. "It's the biggest I have ever had in my ass," she said with a sultry tone. "Well there are plenty of cocks bigger than mine," I assured her. We continued our conversation as Beverly continued to stroke my cock. I learned that she had first been ass fucked before she met Rory in London. Beverly was working in London at the time and she went out with two guys from the office. They took her back to their place and one fucked her ass as she blew the other guy. She took to ass fucking after that but she was very selective about who allowed in her ass. Rory did not like butt fucking. She also told me that this was the first time she had anal sex with anyone since dating Rory. I shared with her that I loved fucking a beautiful ass and that hers was right up there with the best of them. "All this talk and playing with your cock has got me hot again. I need to sit on your dick," she announced. Beverly straddled my body and lowered herself onto me as she held my tool and aimed it at her vagina. My hard cock slid easily into her womb and she emitted a small gasp as it filled her hole. Beverly rocked back and forth on top of me as I held on to her curvy ass. I stroked her ass cheeks and molded her firm buttocks in my hands as she picked up the pace fucking herself with my dick. Beverly started moaning as she fucked faster and faster. I sensed her pending orgasm and then she yelled out. "I am going to explode. Oh, Oh hold me, please hold me tight," she screamed. Beverly collapsed on top of me her body quivering from the intensity of her orgasm. I could feel her juices coating my cock as it remained buried in her womb. It took a few minutes for her to regain her composure and she just lay on me and cooed. Eventually she rolled off of me and lay on her back next to me. "Can I stay here tonight?" she asked in a hopeful tone. "I would love for you to stay the night," I told her. Later she rolled over on her side and faced away from me. I draped my arm over her body and cupped her small breast. Her ass was pressed into my body and my soft cock nestled against her buttocks. We fell asleep in that position and slept soundly through the night. THE DAY AFTER WITH BEVERLY Wednesday morning I woke up with Beverly stroking my cock. She smiled at me when she saw I was awake and then she lowered her mouth to my cock and deep throated me as she had the night before. I had a tremendous urge to piss but I knew I couldn't as long as my cock was hard and I couldn't cum until I took my morning piss. I decided then to fuck Beverly into submission that morning. I rolled her over and got on top of her and slipped my early morning erection into her moist pussy. I started fucking her slowly and gradually picked up the pace as she moaned and groaned with desire. Beverly did not know what she was in that morning and I was determined to fuck her brains out. I could fuck for a long time without cumming the first in the morning with my piss hard-on. As I pounded Beverly's pussy she had a continuous string of orgasms. She was screaming and thrashing in ecstasy. Beverly held me tight, dug her heels into my back and muffled her screams in my shoulder as I pounded her pussy. Finally she shook uncontrollably, screamed and collapsed, her body going limp on the bed. "Please stop fucking me, no more please. I can't cum anymore please let me rest," Beverly pleaded. I eased my still hard cock out of her cunt and I actually heard her pussy sucking as if it was gasping for air. I slid off the bed and went into the bathroom to take my morning piss. When I returned to the bedroom Beverly was in the same position that I had left her. I got back in bed and rolled her over on her stomach. "Please Walt let me rest awhile," Beverly begged. "Relax and I will give you one of my famous massages," I told her. I took the lotion from the night stand and applied it to her back and shoulders. I massaged her neck, shoulders and back rubbing the lotion in and relaxing her body. Then I moved down to her calves and massaged her aching legs. I worked my way up to the back of her thighs and massaged them deeply. Beverly moaned and cooed under the manipulation of my hands and I knew that she was enjoying the massage. I next moved my hands to her buttocks and massaged her glutes as I knew they were fatigued from all of our fucking the past two days. Beverly involuntarily tightened her butt muscles as I massaged them and I felt my cock get hard again. I put more lotion on Beverly's ass and worked some of it into her crack. Beverly raised her ass slightly and I slipped a lubed finger into her bung hole. Beverly gasped at the intrusion but then relaxed and enjoyed the stimulation. I added a second finger and Beverly gasped again. As I worked my two fingers in her ass my cock had become fully erect again. I lifted Beverly by her hips and she allowed me to lift her ass higher as she kept her head on the bed. I was sure that she knew I was going to take her ass again and she offered no protest. I lined up my throbbing cock at the entrance to her ass and pushed it in until the head cleared her sphincter. Once again Beverly gasped at the intrusion but she did not resist. I eased my cock into her ass inch by inch until it was completely buried in her anal channel. I started slowly as I had before and then picked up the pace. Watching Beverly's ass impaled on my cock as I fucked her sent a chill through my body. My own orgasm, the first one of the day, was building in my balls and I knew it would just be a matter of minutes before I ejaculated. My body stiffened, my balls tightened and the first stream of cum entered Beverly's asshole catching her by surprise. I pulled my cock from her ass as I continued shooting cum at her asshole. My semen bounced off her anus and her buttocks and then ran down over her pussy lips onto the bed sheets. After shooting my last stream at her aperture I shoved my cock back into her ass. Beverly once again milked my cock with her anal muscles and drained it dry. My cock stayed hard and I was sure that I could fuck her again but I withdrew my cock from her ass. Cum bubbled from her butt hole and trickled down over her vulva. There was more cum this time since I had shot my first load deep into her rectum. Beverly worked her sphincter and squeezed the semen from her ass as I watched. I then fingered her ass and pussy at the same time. 14 Memorable Anal Encounters 04 "I love the feel of your fingers in my ass and pussy together," Beverly exclaimed! After several minutes of finger fucking her pussy and asshole I couldn't wait any longer and I had to get my cock back in her beautiful ass. I removed my fingers and lined up the head of my cock at her moist puckered ring and pressed forward slowly. My cock head popped through and she let out a little groan. Beverly let out a sigh as her rear passage was once again stretched to accommodate my ample girth. "Oh I love this," she gasped and shivered as I filled her fully and withdrew my penis slightly. I felt her ass tighten around me and I continued to slowly stroke in and out of her tight ass until all 7+ inches were tightly packed up her ass. Beverly really began to moan and her whole body shook in anticipation of what she knew was coming. I began to slowly fuck her but soon picked up the pace as I penetrated her with long hard strokes that used the entire length of my thick cock. Beverly was going wild as she loved the feel of my cock as it pulled out and then came crashing back in. Beverly was thrashing around uncontrollably, gasping and moaning with pleasure. When I reached underneath her to stroke her clit she exploded with her another orgasm. I continued to hammer her ass with long strokes then suddenly I felt that familiar tension in my balls and I knew I was close. I began to piston my raging cock harder into her searing ass in search of my release, which also increased the intensity of her orgasm. She was yelling and moaning, clawing and scratching at the cover on the bed begging me to cum. "Give it to me, give it to me, give me your cum, cum in my ass," she begged. I took firm hold of her hips and slammed once more full force into Beverly's ass. I did that three or four more times and then I let out a loud groan as I emptied my seed deep into her bowels. I couldn't believe how much cum I produced as my dick continued to hammer into her ass. When I was finished I pulled out of her ass as Beverly collapsed on the bed utterly spent. I slumped down next to her quivering body. I looked over at Beverly and I noticed my seed oozing from her asshole. After that we were really spent and had just enough energy to shower, dress and enjoy a cup of coffee. "Have you got anything to eat in this place?" she asked. "Absolutely, I did some grocery shopping when I got here. I have eggs, bread, cereal milk, fruit and meat. What's your pleasure?" "I'll have cereal with fruit, thanks!" she requested. Beverly and I had breakfast and then she had to get going. She told me that her boyfriend Rory was arriving later that day. Beverly thought it was cool that I was going to complete the Advanced Open Water training before I left the Caymans. Beverly left for her room and then I headed down to the dive shop. I signed up for two dives that afternoon and experienced my first open water dives without an instructor. My buddy was another guy and he was an okay diver so the dives went very smooth. I was already looking forward to my Advanced Open Water training and learning more, particularly about navigation. I never saw Beverly after that day but I never forgot the great ass fuck. NUMBER 4 -- PAMELA I selected Pam as number 4 mainly because of her kinky and strange behavior at times. She was an attractive woman of 28 years old and I was 31 at the time. It was 1972 and I was working for a manufacturing company in the Midwest at the time I met Pam. Actually she sought me out after seeing me in my softball uniform one evening. She was a little heavier in the hips and thighs than I normally liked but her sexual behavior overshadowed that. Pam worked in a different division in our company and I met her one night at the bowling ally. Pam was definitely the most adventurous lover that I had sex with to that point since moving to the Midwest. She liked to take risks and seemed to thrive on the possibility of getting caught. Pam was engaged to be married and the idea of her fucking around on her fiancé seemed to turn her on. I had always thought the engagement period to be more sacred than marriage but Pam didn't. Our company had a bowling league that met every other Tuesday evening, which I participated in. After bowling many of us adjourned to the lounge for drinking and dancing. It was in the lounge that I met Pam. I walked in and sat down at the tables that the guys had pushed together and Pam sat right next to me. I had seen her in the league but I had never actually met her before that night. I introduced myself to Pam and she was definitely hot to trot. I couldn't help but notice her engagement ring but that didn't keep her from coming on to me. Some of the people at our tables started dancing and I asked Pam if she would like to dance. She enthusiastically accepted and within seconds we were slow dancing on the dance floor. Pam held me tight and pushed one of her legs between mine. You couldn't have passed a ray of light between us because of how close we were to each other. My cock stiffened in my pants and it rubbed along Pam's thigh. She clearly felt it and moved her hips even more seductively and rubbed against my cock. When a faster song came one I suggested that we take a short break. Not that I don't like to boogie but my pants were straining against my hard-on and I was thirsty. We returned to the table and I poured us a glass of beer from the pitcher. As we were talking and drinking, Pam asked me if I could give her a ride home as she had come to the alley with her girlfriend who already had left. I agreed and we finished our beers and then I took her home. When we got to Pam's apartment she invited me to come in which I thought was odd because she was engaged. Once inside she offered me a drink and then we sat together on her sofa. "You know I could feel you against me tonight when we danced," Pam told me. I laughed and replied, "Yes well we did dance pretty close and I could feel your body as well." "I meant that I could feel your cock rubbing against my thigh. It was obvious that you were happy to be with me," Pam said with a very sultry look. "I enjoyed dancing with you Pam. Where do you want to take this? Would you like make it together?" I asked testing her. Then I reached for her, pulled her toward me and we embraced and kissed. Pam ran her tongue deep into my mouth and I thought that this was one hot lady. I rubbed Pam's tits through her blouse and she stroked my erect cock through my pants. I unbuttoned her blouse and removed it from her body then I unhooked her bra letting her medium size firm tits spill into my hands. "We shouldn't do this my fiancé is coming over tonight," Pam said unconvincingly and then she kissed me again. We kept kissing and I played with her tits and nipples. Then I moved my mouth down to suck on Pam's tits. As I sucked on her tits and nibbled lightly on her nipples, I unbuckled her belt and slid it off her slacks. Then I unfastened her slacks and unzipped them. I stood up off the sofa and I pulled Pam's slacks down and off her legs. She didn't resist at all, in fact she lifted her legs to help me. Then I hooked my fingers in her panties and slid them down and off her legs. "We really shouldn't, Rob will be here any minute," Pam said as if she was convincing herself. At that point I didn't know whether to believe her or not but we were too far along to stop now. I leaned over to kiss her creamy thick thighs. She gasped aloud at the touch of my lips to her naked skin. I sensed that she was struggling with the decision on how far she should let this go. I could smell the sweet aroma of sex that was given off by her pussy as my face moved closer to her crotch. I lifted Pam's legs to my shoulders and kissed her inner thighs just below her pussy. She groaned with pleasure as she reached down with her hands to control my head. Pam faked trying to keep my head from reaching her pussy but I tickled her outer lips with my fingers and then let them slip inside her vagina. Pam was so wet that two of my fingers slid in easily and she consciously relaxed her grip on my head. I moved my mouth toward her and closed over her pussy shoving my tongue into her wetness. Pam cried out and grabbed my head again but this time she held it tight to her quim. I lapped at her pussy as I fingered her with two fingers. Then I spread her pussy lips apart and located her throbbing clit peeking out from its protective hood. Pam was really excited as her erect clit looked like a teeny dick sticking out. I sucked on her hard clit and she bucked her hips up into my face. I reached under her and cupped her shapely ass cheeks in my hands as I drove into her pussy with my tongue and nibbled on her clit. Pam had a big ass but it was round and firm. "Oh shit, I'm cumming. Hold me, please hold tight," she screamed as she lost it. The climax rocked her body and I held on for dear life as she thrashed, twisted and bucked all over the sofa. I kept right on eating her pussy and I held onto her shapely ass as she thrashed about. Pam slowly calmed after her intense orgasm and I continued to lick her until her pussy was dry. As we lay on her sofa I continued to lick and kiss her bare thighs as she ran her hands through my hair. "Oh that was something I really came hard. Thank you, thank you!" she murmured and then added, "But you have to go Rob will be here any minute now." There was no way I was leaving now without getting my rocks off and if Rob showed up while I was fucking his fiancée, so be it. Pam watched me as if she was in a trance as I pushed my pants down to my knees and my rock hard cock leaped out. I moved between her thighs and placed my cock at the entrance to her cunt. She shivered in anticipation. I eased her back down on the sofa and proceeded to feed my thick cock to her. "Oh we mustn't, we shouldn't, it is not right, Rob will be her soon and then oh yes, oh it feels so good, oh, oh, fuck me, yes fuck", she cried. I slid in and out of her pussy slowly allowing her to adjust to my size and continued to go deeper with each thrust until I was buried balls deep in her pussy. "Oh my I have never been so full of cock, fuck me, make me cum, make it last forever", she cried out. "I knew you would have a big cock." I pounded her pussy making sure that my cock was in constant contact with her clit. Pam had multiple orgasms as I fucked her. She had nice firm tits with rock hard nipples that extended nearly a ½ inch. I twirled the nipples in my fingers and then leaned over taking one then the other in my mouth. She went wild telling me. "Oh yes, suck my tits, suck my nipples, fuck me good!" I could feel my balls start to tighten and I knew it wouldn't be long before I filled her pussy with my cum. Pam stiffened and then had another violent orgasm. She yelled, "Hold me, please hold me, I'm cummmming!" I reached around behind her and pulled her toward me as she shook and trembled throughout her intense orgasm. As she was cumming so did I and I fired a barrage of cum into her pussy. As she started to recover I laid her back down on the sofa and slowly fucked her as my cock softened. My cock was swimming in her cunt; there was so much of my spunk in there mingling with her own juices. "Oh you filled my pussy up with your cum. Please go now, Rob is on his way here," Pam said again. I pulled my underwear and my pants back up and re-dressed. I took another sip of my drink and then I told Pam that I would leave now. I walked to her door and she quickly got up and followed me. She stood in her doorway naked and kissed me goodnight as I left. It was as if she wanted to be seen naked. Then she closed the door behind me and I could hear the lock being turned in the door. I made my way over to my car and I did not see anyone in the parking lot. I wondered if Pam's fiancé was really coming over that night or was this just part of Pam's fantasy or game playing. I had thought about going for her ass but the mood wasn't right particularly if her fiancé was really coming over. I thought that my date with Pam was a one night stand and that I wouldn't make it with her again. However she pursued me and we ended up spending a lot of evenings together. Pam asked me to play tennis one evening with another couple. We had a fun match and Pam looked very desirable in her Tennis outfit. Afterward I drove Pam back to her apartment and she had me park in a secluded part of the lot. "Rob is here, I saw his car in the lot," she said. "Here we go again," I thought to myself. "Since we can't go in," Pam said as she reached for my tennis shorts. Pam unfastened my shorts and I lifted my hips as she pulled my shorts and underwear down below my crotch. My erect cock caught in the waistband of my underwear and then bobbed in front of me as it cleared the waistband. That seemed to turn Pam on. "Oh ho, someone is happy to see me," she said as she reached for my cock. Pam then lowered her mouth to my cock and deep throated me taking as much as she could on her initial descent. She had a marvelous technique of swirling her tongue around my cock while it was in her mouth. Pam's head bobbed up and down on my cock and I felt my orgasm building in my balls. I opted not to warn her that I was about to cum. Pam sucked my cock with enthusiasm as she tickled my balls and perineum. I felt my semen travel the length of my cock and shoot into her mouth. Pam sucked and swallowed as fast as she could, not missing a single drop of cum. Pam kept sucking me keeping me hard long after I finished cumming in her mouth. "That made me really hot. I need to sit on your dick," she said. We scrambled into the backseat of my car and Pam reached under her tennis skirt and removed her panties. Then she straddled my cock and serviced herself. I was pinned to the car seat so Pam did all the work. She rode my cock through multiple orgasms until I came again. Then she stopped moving and placed her head on my shoulder and eventually calmed down after cumming several times. "I better get inside, Rob is probably wondering where I am," Pam said. She got out of the car and just carried her panties with her. I watched as she walked across the parking lot and I envisioned cum running out of her pussy and trickling down her inner thighs. If Rob was there would she kiss him with the taste of cum still in her mouth? Would he eat her pussy with my seed still in her cunt? Or was he even there tonight or was it just another game that Pam liked to play? I would never know but it was fun to speculate. Pam and I saw each other once a week for the next several months. She seemed to like to take chances and we had sex in public places a couple of times. Once I had to drive her to pick up her car at the service center and it wouldn't be ready for another hour. Instead of waiting in the customer waiting room we fucked in my car in the dealership parking lot. Another time she sucked my cock and I ate her pussy in my office. Once we fucked in the exercise facility at her apartment complex and then fucked again in the steam room. Pam was always acting worried about getting caught by Rob but he never seemed to materialize. I still think that it was all part of her fantasy. FINALLY HER ASS One night Pam called me and asked me to meet her in a hotel room not far from her apartment. I agreed to see her that night so I drove over to that hotel. Pam answered the door and she was dressed in white panties and a sweater bra. I had never seen a sweater bra before but it was kind of sexy. Pam told me to come in and then she turned and walked back into the room. As Pam walked away from me I looked at her big round ass and fleshy thighs. Pam was a little heavier in her ass and thighs than I normally liked but she was so solid that it didn't bother me. As I looked at Pam's big round curvy ass I decided to try and fuck her ass that night. I walked in the room and Pam began unbuttoning my shirt. Pam unbuttoned and removed my shirt. Then she kissed me and worked her way down my body kissing my chest down to my waist. Pam then unbuckled my belt, unfastened my pants and pulled my pants down my legs. I slipped off my loafers and then lifted one leg at a time so that Pam could pull my trousers off. Pam then removed my socks before returning to my underwear. My cock was rock hard in my briefs and Pam ran her hand over the outline of my cock in my underwear. She looked up at me and smiled. Then she hooked her fingers in the waistband of my briefs and slowly pulled them over my pubes. Pam made sure that my cock got caught in the waistband as she seemed to like to see it spring out. Pam pulled my underwear as far down as she could without freeing my cock. Then she finally pulled the briefs clear and my cock sprung out into her face. She smiled as it bobbed in front of her. "I can see that someone is happy to see me again," Pam said as she always did when my cock bobbed around in front of her. Pam then pulled my briefs all the way off and I stepped out of them. Instead of sucking my cock she went over to the bed and flopped down across it. I walked over to the bed and I grabbed her panties and yanked them off her body. I left the sweater bra on her as she actually looked sexier partially clothed. I lifted her up by her hips and I ran my tongue along her pussy lips. Pam cooed as my tongue found its way into her pussy and then located her clit. I spotted some lotion on the table next to the bed so I took it and put a lot of it on my hand. I rubbed the lotion into the crack of Pam's ass and then I slipped a finger into her asshole. I began to finger fuck Pam's ass with my index finger and then I pushed my middle finger and ring finger into her pussy. I finger fucked her pussy and ass at the same time with my three fingers. "Oh that feels good. Imagine what a tongue would feel like in there," she said and then added, "I douched my pussy and my ass tonight in case you want to put your tongue in there." It had been awhile since I rimmed a girl's asshole but I was in the mood for some anal sex and I went for it. I grabbed Pam's fleshy ass cheeks and pried them apart so that I could get a good look at her rosebud. I ran my tongue around the rim causing her to gasp. I moved my tongue from her ass to her pussy and back again driving her wild. True to her word, her ass was clean and smelled fresh. Pam began cumming and her hips rotated as she moved her big ass around. I fastened my mouth to her pussy and clamped onto her clit. Pam screamed in orgasm and then her body flattened on the bed. I was about to shove my cock in her pussy when she rolled over. "I want you to fuck me like this," she said as she raised her legs back to her shoulders, "I want my legs on your shoulders as you drill me with your cock." I got up and stood above her on the bed and lowered my cock into Pam's pussy. Pam placed her legs on my shoulders and I leaned forward over her. I placed my hands on the bed above Pam's head for balance and I drilled her pussy from above. I fucked her hard and fast as she was really into this position. I felt as if we were filming a porn movie. I had never fucked anyone in this position before but I was getting into it and I let her have it. Pam was groaning and moaning as she had a string of orgasms as I pounded her pussy. "I want to see you shoot. I want you to cum on me. Aim it at my face," Pam said with her voice cracking. I felt my balls tighten and I knew I was close. I pulled out of Pam's pussy and stood above her as I started to cum. I aimed my cock at her face and fired streams of cum at her. The first couple of streams hit her hair, face and neck and ran down over her tits. Then as my ejaculation slowed, ribbons of cum covered her abs and pubes. "Oh look at it all. Cream me, cover me with your cum," she called out with her voice cracking in her desirous state. 14 Memorable Anal Encounters 04 Pam then scrambled to a sitting position and took my cock in her mouth. She sucked me dry as she gently squeezed my balls. I finally couldn't stand on the bed any longer so I flopped down along side of her. Just then the telephone rang. Pam answered the phone as I lay on the bed. "Now Rob I told you that I needed some time to myself. I just have to think about things. No you cannot come up," Pam said into the phone. "I told you I called my daddy and he told me to stay at the hotel. He paid for the room for me so that I can deal with my issues. Now you just go home and I'll talk with you in a few days," Pam said and then hung up. The phone rang again and Pam answered it. Once again she chastised Rob for calling her and being a pest. I told her to call down to the front desk and tell them to hold all her calls. Pam did that and the calls stopped. I knew that the hotel would not give out the room number and that her fiancé would probably just stop trying to reach her. "How did he know you were here?" I asked. "Oh he probably saw my car in the hotel parking lot," Pam replied. That told me that she had done this before. The mood had been temporarily broken but now I was ready to take her ass. I pulled her toward me and our bodies meshed together and I felt the wetness from my semen. I lifted Pam's sweater bra off her body and rubbed her sensitive tits. "Have you ever been fucked in the ass?" I asked her. "Yes," she admitted, "But with Vaseline." I smiled at Pam and put her on all fours. She turned her body so that she could watch herself in the mirror. She was sideways to the mirror on all fours when I began to grease up her asshole with the hotel supplied body lotion. I applied lotion to her ass cheeks and then I added more to her asshole. I fingered her asshole with my little finger than a larger one and finally my thumb with my middle finger stroking her enlarged clit. Pam raised her hips slightly so that I could get to her pussy easier and by doing so she accentuated her shapely ass. My thumb was snug in her ass and my cock was throbbing again. "Are you getting me ready for your big cock?" Pam asked as she watched us in the mirror. I answered her by removing my thumb, kissing my way down her arched back as I fondled her curvy buttocks with my hands. I planted kisses on her ass cheeks and tickled her pink hole with my tongue. She gasped out loud as I rimmed her again that night. I backed off and asked her if she was all right to which she wiggled her ass and told me to keep tonguing her bottom. I lifted her hips up a little higher and gently spread her ass cheeks wider and lapped around her bung hole. I penetrated her rectum with the tip of my tongue and I heard her breathing become shallow and labored. I slipped my tongue in as deep as I could and Pam went wild. Her body shook with convulsions as she had yet another intense orgasm. I held on to her hips with my tongue buried in her ass as she bucked and trembled. I then moved behind her and eased my cock into her well prepared asshole. Pam had totally relaxed and it took her awhile to realize that the head of my cock was now in her ass. I had added more lotion along with my saliva making my dick very slick. "Not too deep at first it's been awhile. Let me get used to it then you can go deeper but slowly," she coaxed. I fed it to her a little at a time probably no more than a quarter or half inch. Each time I allowed her to adjust to the thickness and deepness of the penetration. It seemed like hours before my cock was fully lodged in her ass. Once I thought she was comfortable I started fucking her ass, first with short stokes and then longer ones. I was very turned on as I watched my cock saw in and out of her big beautiful ass. Pam had her head turned to the side of the mattress and she was gripping the bed sheets with both hands as I fondled her shapely buttocks and plowed into her. I spotted Pam's engagement ring on her hand as she gripped the bed covers. I wondered what her fiancé would say if he could see her now with a big cock up her ass. I could feel myself on the verge of another big orgasm and it felt like it started in my toes. All of a sudden it let loose and I filled her asshole with cum. My cock seemed to swell up bigger than ever and it seemed that my sperm had no where to go. I kept slowly fucking her ass until my cock started to soften. Pam's ass involuntarily was milking my cock draining it of all my seed. When my cock slipped from her asshole with an audible pop, my cum shot out and ran down the back of her legs and over her pussy. It looked like Pam was shooting cum out of her ass. She collapsed face down on the bed and I lay down along side of her. We were drained and exhausted. I stroked her buns lovingly as we lay quietly. Pam said, "I liked that, you made it very enjoyable. Will you be able to fuck my ass again before you leave?" After we rested I was able to fuck her ass again but it took a very long time for me to cum. I did manage to shoot my third load of the night into her ass again. Pam told me that she had never felt so full and it was a feeling of giving complete control to someone else. Pam thought that being fucked in the ass was the ultimate in submission and she felt totally dominated. I showered, dressed and said goodnight to Pam who was content to lie on the bed face down with cum oozing from her ass. She didn't get up when I left so I just patted her on the ass and told her what a great ass fuck she was. I walked down the stairs to the lobby and as I walked through the lobby I noticed a guy sitting in one of the soft chairs. He eyed me suspiciously as I left the hotel. I thought to myself that must be Rob, poor guy. That was the last time that Pam and I got together. She eventually took another job and I never did see her or hear from her again. I don't know if she ever married Rob but for his sake I hoped not. I wondered how many other guys she might fuck and how many she would let in her ass. I was fortunate to be one of them. NEXT CHAPTER The next chapter will be devoted to Bonnie and Charlotte my number 2 & 3 anal sex favorites. 14 Memorable Anal Encounters 05 AUTHORS NOTE: I decided to submit stories of my life's anal encounters. Of all the women that I hooked up with over the years, fourteen of them included anal sex. Some of these were affairs that lasted for months and some for years. Others were memorable one night stands. Instead of going in chronological order I ranked the encounters according to the hottest ones beginning at number fourteen and working my way to number one. Over my lifetime dating back to 1959 when I turned 18 years old, I have had hundreds of sexual encounters with over fifty women. Being a leg and ass man, my most memorable encounters included anal sex. Most all of my sexual encounters were pleasant but these involved anal sex. INTRODUCTION My age will range from 29 to 48 during the years 1970 through 1990. The one thing that I pride myself on is staying fit through all those years and even today at age 72. I am 6'0" tall and have always weighed between 205 and 215, my current weight. In the early years I played softball, football and basketball. Eventually I shifted to the individual sports of tennis and golf. I am still an avid downhill skier and SCUBA diver and I am still taking martial arts classes. In addition I make it to the gym at least three days a week and I am a ski instructor at a local ski area in the Midwest. I love to travel and although not fluent, I am very comfortable with the Spanish, Italian, and French languages. I am also currently studying Mandarin Chinese. I enjoy reading and the arts and I am a frequent live theater attendee. I have traveled to Spain, Italy, France and the UK over the years as well as some of the best SCUBA diving spots in the Caribbean and best ski mountains in the U.S. and Europe. Some of my other story submissions to literotica speak to my experiences in other countries and islands as well as at home in the states. I served four years in the Marine Corps and I was honorably discharged in 1963. I will begin the stories with number 14 and work my way up to number 1. Due to the length I have broken the stories up into chapters so that a single submission would not be too lengthy. Also there will be some redundancy in the description of sex acts, after all how could there not be. I had my favorite positions and activities and they were often repeated with different partners. The ranking and dates of the encounters are as follows: 1-Cathleen (1985 -1990) 2-Charlotte (1970-1972), 3-Bonnie (1974), 4-Pamela (1973), 5-Beverly (1977), 6-Sherry (1983), 7-Peggy (1976), 8-Lee (1982), 9-Barbara (1984), 10-Rita (1978), 11-Terri (1979), 12-Susan (1971), 13- Toni (1978), 14-Cindy (1973). NUMBER 3 – BONNIE Bonnie and I had been out several times and we did sleep together each time. She was a great lay with a fantastic body but she had this odd behavior. She always acted reluctant toward anal and oral sex. When I came in her mouth she acted annoyed and when I fucked her ass she acted as if she didn't want to do it, but she always did it and she never once refused to suck my cock or take it in the ass. I suspected it was her way of justifying her behavior. I met Bonnie in night school in 1975. Bonnie was a vibrant young woman with light brown hair that just covered her neck. She had a nice figure with tits that I guessed to be a 34 C but her best feature was her round shapely bubble butt. I had always been a leg and ass man, so nice tits were a bonus but not a necessity, as I favored women with shapely bottoms. She looked great totally naked and I would often stroke and play with her fabulous body until she begged me to take her to bed. Bonnie had one of the nicest asses that I had ever seen and I loved fucking her hot ass. One Friday night she invited me over to her place. We sat on the sofa watching TV, sipping our drinks and discussing the college class. I got up to refresh my drink and when I returned I sat next to her. She turned toward me and smiled nervously as she anticipated my next move. I smiled back and put my arm around her and drew her to me. I gently pulled her toward me and our mouths locked in a kiss. I pushed my tongue into her mouth and it took her breath away. Bonnie kissed me back and her body relaxed as she welcomed the fact that she would get fucked that night. I lifted her sweater up over her head as she held her arms up for me to remove it. Next I unfastened her bra and as I removed it her tits stood straight out from her chest. I pushed her shoulders back against the sofa causing her tits to look bigger and firmer. Bonnie moaned as I leaned over and kissed her breasts and sucked on her rock hard nipples. I kissed and sucked her tits for several minutes. Her nipples got so long and so hard that they were like little dicks sticking out from her tits. She loved to have her tits fondled and kissed. I moved off the sofa and knelt between her legs. I unzipped her skirt and she lifted her hips as I pulled it down and off her body. Bonnie looked very sexy clad only in her thigh high nylons and her robin blue panties with her aroused tits standing straight out. Hooking my fingers in the waistband of her panties I slowly peeled them down her legs. As I removed her panties I stared directly at her snatch and gently pushed her legs apart. Bonnie groaned as I ran my finger over her well trimmed pussy mound and tickled her labia. Her hips jerked involuntarily when I probed her sopping wet pussy with my finger and kissed her inner thighs. Bonnie gasped aloud when my tongue finally touched her quim. I raised Bonnie's legs up and placed them on my shoulders which brought her pussy even closer to my mouth. Then I reached up and fondled her tits with both hands, tweaked her nipples and plunged my tongue into the depths of her pussy. I licked her cunt and located her erect clit with my tongue. As I sucked on her clit and played her tits and nipples, Bonnie moaned loudly as her body thrashed around. I struggled to keep my mouth glued to her pussy as her body jumped all over the sofa. Bonnie grabbed my head with both hands and held me to her gushing pussy. "Oh Walt, this is going to be a quick one, a big one," she cried out and then she screamed, "I'm cumming, oh God I'm cumming, hold me, hold me tight, please hold me." Bonnie's body seemed to go through convulsions as her orgasm rocked her and sent tremors through her. She continued to hold my head to her mound as her sweet nectar gushed into my mouth. I licked her dry and nibbled on her clit which caused her body to quake again. Bonnie collapsed on the sofa so I stood up and looked down at her hot body as I peeled off my shirt. Unbuckling my belt and unzipping my pants, I pushed my trousers down to my ankles. My large erection was covered by my underwear but my state of desire was obvious. I pushed my underwear down and my cock caught in the waistband and bobbed in front of Bonnie. She stared at my erect cock as it dangled inches from her face. Bonnie stared at it as if she was looking at the first cock she had ever seen in person. I reached down and pulled her closer to me so that her mouth was now on a level with my cock. "Your turn," I said as I pushed my cock toward her mouth. "I don't like to suck cock," Bonnie said acting out her reluctance. "Well make an exception this time," I replied firmly. "Please don't make me do it," she begged. "I'm not going to make you do it. I want you to want to do it. Just suck it for awhile until I am really hard. I won't cum in your mouth if that's what you are worried about," I told her trying convince her to suck my cock. Then I reminded her, "After all I did eat your pussy and lick up all your love juice." Bonnie reluctantly moved her head forward and kissed the head of my cock. Then she licked up and down the shaft and all around it. Eventually, after more urging on my part, she took about four inches of my cock into her mouth. In spite of her suspect reluctance, Bonnie was clearly an experienced cocksucker. She clearly knew her way around a cock and she seemed enamored with mine as she loved it with her mouth. As I looked at her distraught face sucking my cock I thought about my promise to not cum in her mouth. "Yeah I won't cum in your mouth tonight but before this weekend is over you will taste it and feel my seed coat your rectum," I thought to myself. As I lifted Bonnie's chin up and my cock slipped from her mouth she spoke, "Can we go upstairs to my bedroom?" she asked hopefully. "I thought that you would never ask," I teased. Bonnie led me to her bedroom and I watched her fantastic ass as she walked up the stairs in front of me. Her beautiful shapely ass undulated as she climbed the stairs and I felt that familiar surge in my loins. I wanted to throw her down right on the stairs, shove my cock all the way up her ass and fuck her until I filled her rectum with semen. But I knew better, so I watched her shapely bottom with each step she took up the stairs. I knew that I wouldn't be happy until I fucked her ass that weekend. I followed her up the stairs and into her bedroom. Bonnie pulled down her bed covers and got in bed on her back. She spread her legs slightly and looked apprehensively at my erect cock. I got on the bed between her thighs and nestled my cock at the opening to her pussy. I moved the head of my cock around her vulva and gently prodded her outer cunt lips. Bonnie moaned softly as her pussy got increasingly wetter. Satisfied that she was wet enough I eased my dick in a little parting her labia and finding the entrance to her pussy. I pushed more of my cock into her and in spite of her wetness she was still very snug. For the next several minutes I pushed in and pulled out, each time pushing a little more of my shaft into her sopping wet hole. Finally my cock sank all the way into her snatch causing Bonnie to gasp aloud. Then as I began to saw my dick in and out of her, Bonnie wrapped her legs around my lower body and humped her hips up at me. As I picked up the pace I made sure that my cock stayed in constant contact with her clit. Bonnie surprised herself with another quick orgasm but I kept right on fucking her and she came multiple times in succession. Her pussy was flooded with her cunt juice and I could feel my cock soaking in her nectar as I pushed it all the way in. Bonnie was experiencing a continuous string of orgasms which had her body thrashing and jerking about as they led up to her final crescendo. Her body stiffened and she grabbed my shoulders as she wrapped her legs even tighter around my torso squeezing my lower body. "Oh God, I'm cumming again, hold me, please hold me, oh, oh, please," she cried out as a thunderous climax ripped through her body. Bonnie stiffened at first pushing her hips toward mine and the she went out of control. Her hips humped rapidly up and down as her body thrashed about. She was grunting and groaning and gasping for air as she reached her crescendo. All her fanatic actions accelerated my own orgasm and I flooded her womb with barrage after barrage of semen. I plowed my cock into her as far as I could as I released a steady flow of spunk into her pussy. We both humped each other furiously until our orgasms subsided. I kept my weight on my elbows as I lay on top of her so as not to crush her body with my weight. Bonnie's vaginal muscles clenched and unclenched around my shaft milking my cock dry. Her cunt was a receptacle holding our combined juices and my cock felt as if it bathing in warm oil. My cock slowly deflated and slipped from her tight pussy with an audible sound. Our juices flowed out of her pussy as soon as my cock slipped from her hole just as if a stopper was pulled out of her. I rolled to my side along side of Bonnie and flopped on my back. "Oh my, I haven't cum like that in a while. It was a little scary," she sighed and then added. As I lay by her side I noticed that her tits were standing straight up and her aroused nipples were pointing at the ceiling. I tweaked the hard little nubs between my fingers causing her to gasp and quiver. "My breasts are always very sensitive," she murmured. I leaned over and kissed her breasts and sucked on her sensitive nipples. I rubbed her firm flat tummy as I sucked on her tits and her rock hard nubs. "Oh I love that it makes me feel so feminine," she cooed. As I sucked her tits and continued to rub her belly, I let my hand drift down to her wet pussy. I ran my fingers through her cum soaked pubic hair and I felt my cock starting to harden. Bonnie begged me to let her rest as she was sure that she could not possibly cum again. I rolled her onto her stomach and lifted her hips to a level with my cock as I knelt behind her. I eased my cock into her pussy and began to fuck her doggy style. Bonnie was content in this position since I was not in contact with her clit. I slammed into her from behind causing her curvy ass cheeks to jiggle. I scooped up gobs of her pussy juice and smeared it in the crack of her ass spreading around her nether hole. I added saliva to my finger and probed her tight aperture with the tip of my finger. She tensed when she felt my finger probe her asshole. I gathered up more juices and added more saliva as I continued to probe her hole and open her up. I gently pushed a very well lubricated finger into her ass and the tiny aperture opened up to accept the digit. More saliva and more juices greased her asshole sufficiently to allow me to slide my finger all the way into her rectum. Bonnie thought that I was preparing her ass for my cock when she said, "Please don't. I don't like anal sex." "Don't worry," I assured her, "I will just play with your ass as I fuck you." Now with my cock in her pussy and my finger in her ass I was approaching another orgasm. I could it building in my balls, travel through my scrotum and splash the insides of her vagina with my warm semen. As I came in her pussy I thought to myself yet again, "Just wait until you feel my warm seed fill your ass tomorrow night." On Saturday morning I woke up first with a piss hard-on. This happened frequently to me when I spent the night with a hot woman. With this piss hard-on I was able to fuck for quite awhile without cumming and until the bladder pressure got so intense that I had to relieve myself. I rolled over toward Bonnie and started caressing her body. She rolled on her back and I went to work on her firm tits and hard nipples. She cooed from the titillation and gradually woke up. Then I moved between her legs and slid my erect dick in her pussy. The fit was tight again so I moved slowly and gently working my cock into her. Bonnie got wet quickly and my cock was soon sliding in and out of her hot cunt. As she had done before she wrapped her legs around my lower body and her arms around my back as she humped back at me. I fucked her through multiple orgasms just as I had done last night except that I didn't cum. Bonnie arched her back and her body shook with the intensity of her climax. I kept fucking her and she had another continuous string of orgasms before her body stopped moving of its own accord. "Please stop, let me rest, I can't cum anymore," Bonnie cried out, "Walt please stop, please." I stopped fucking her honoring her plea and I slowly slid my still erect cock from her. I headed into the bathroom to relieve the pressure of my piss hard-on and then I opted to take a shower. Bonnie joined me in the bathroom once she heard the shower running. I invited her to join me in the shower. Bonnie and I soaped each other's body and I loved running my soapy hands all over her fantastic tits and ass. Bonnie played with my erect cock and lathered it up with soap. I turned her toward the shower wall and slid my cock into her pussy from behind. Bonnie braced herself against the shower wall as I fucked her pussy until I came shooting another good sized load into her. We finished showering and Bonnie douched all the semen from her body. Afterwards we got dressed and went out for breakfast and spent the day together. That evening we had dinner at the Wine Cellar her favorite restaurant. As we drove back to her condo Bonnie was very amorous as the wine had an obvious effect on her. When we arrived we went straight to her bedroom, undressed and got in her bed. I moved Bonnie into a 69 position and ate her until she came. Once again she came quickly and thrust her pussy at me as I ate her dry. She sucked my cock without my urging this time but I still did not cum in her mouth. I rolled Bonnie on her back and slid between her legs. My cock slid in easily this time and I fucked her silly before finally shooting my load in her pussy. Bonnie really came hard again as the orgasm ripped through her body. She was a very sensuous woman. We lay together and I played with her tits and nipples and worked them into a state of arousal. Bonnie cooed as I worked on her tits, rubbed her tummy and played with her soaked pussy. Once again I got hard from the foreplay and rolled her over on all fours. Bonnie agreeably moved into the doggy position and accepted my cock in her pussy. As I fucked her slowly I rubbed her tits and played with her asshole. I easily inserted one finger in her ass and then with my other hand I diddled her clit as I fucked her from behind, Bonnie went wild again with all the stimulation and she began bucking her hips as her orgasm took over her body. As she was bucking I slipped my cock out of her pussy and quickly pushed it in her ass. Bonnie bucked and humped through her orgasm before she reacted to my cock in her ass. Bonnie put on her reluctant act, "No please not that. Take it out. You know I don't want to do this. Please take it out!" But I didn't take it out and I ignored her pleas as I pushed more of my cock into her ass. I added more saliva and pussy juice as I fucked her and shoved more cock into her ass. Bonnie tried to break loose but I held her hips firmly. Another push and my entire cock went all the way in her ass. Her asshole opened up from the reaming and I was then able to slide my cock in and out with ease. I was convinced at that moment that she had been butt fucked before. I marveled at her shapely hot ass as I watched her impaled on my cock. "Walt please don't, I don't want to do this. Please don't cum in me," Bonnie acted again but not as urgently this time. Once again I ignored her pleas and I picked up the pace. I could feel my own orgasm approaching and I knew it would be a big one since I was so turned on fucking Bonnie's beautiful ass. Her ass had loosened up and my cock was sliding easily in and out of her rectum. My hips slammed into hers and her ass jiggled as my cock went balls deep into her asshole. I felt my balls tighten so I pushed my cock all the way in her ass and then I released torrents of semen into her rectum. Stream after stream of semen filled her asshole as I flooded her bowels with my load. I realized that we were both motionless and I had my cock buried all the way up her ass. Then I began to fuck her ass slowly again and I pushed my copious load around in her rectum. As I withdrew my softening cock from her ass, gobs of spunk trickled out and ran down over her pussy lips and inner thighs. Bonnie flopped facedown on the bed and I knelt there watching my seed ooze out of her shapely ass. "Why did you do that to me? You know I didn't want that. I told you that I don't like anal sex," she whimpered. I thought to myself, get used to it but I said, "You always say that but you know that I can't resist your ass. It is so beautiful, so hot, so inviting." "I don't want you to ever do it again. I don't like it," she said as she always would. I had knew that she had been butt fucked before me since my cock went in fairly easy with the right amount of lube and she did not complain of any pain. Bonnie got out of bed and went into the bathroom to clean up. When she returned we cuddled in the spoon position and we fell asleep without any more conversation. I woke up at about 3:00 AM with a piss hard-on but this time I went to bathroom and relived myself. While in the bathroom I located some lotion and I put an ample amount on my cock before returning to bed. When I got back in bed I snuggled up to Bonnie and slipped my lotion covered cock into her ass. I had both hands around her body so I played with her tits and fingered her pussy as I slowly fucked her ass. Bonnie woke up and quickly realized that I was back in her ass. "Oh not again, please no," she whispered. 14 Memorable Anal Encounters 05 I just kept fucking her until I came in her ass again. Ropes of semen shot into her ass and I felt the involuntary clutching and un-clutching of her anal muscles around my cock. Her sphincter muscle milked my cock dry as it tried to expel the intruder. My cock softened and slipped from her ass emitting a grunt from Bonnie when it did. I held her to me and we both eventually fell back asleep. Sunday morning was a repeat of Saturday morning as I fucked Bonnie through countless orgasms until she begged me to stop. Then we fucked in the shower again and I came in her pussy. We went out for breakfast and then to the park for a long walk. Later we ate at a casual restaurant. After dinner we drove back to Bonnie's house and as before we immediately went up to her bedroom. As we had done last night we got into a 69 position on our sides. I ate Bonnie's pussy and fingered her asshole again as she sucked my cock. Bonnie assumed that this was our normal foreplay in preparation for our fuck session but I surprised her when I came in her mouth. I was particularly turned on and I had been thinking about cumming in her mouth all day. It didn't take long after we were in the 69 position that I shot a rope of cum in her mouth. Bonnie jerked her head back in surprise and the second shot hit her on her face. Bonnie put her hand over my cock head to block the shots but a third one hit her face before she could block anymore. Bonnie spit out as much as she could of the first shot that filled her mouth but I knew she could still taste it. "Why did you cum in my mouth? You promised me that you wouldn't. It is so humiliating!" she said faking her reluctance one again. "Oh stop your acting. I swallow your pussy juice all the time. A little cum isn't going to hurt you," I replied sternly and then added, "I didn't promise you tonight that I wouldn't cum in your mouth. I was pretty turned on and you were doing a good job sucking my cock and I just lost it." "Well you could have warned me that you were about to cum," she snapped. "Yes I could have but I decided not to as I wanted to cum in your mouth just as I wanted to cum in your ass," I replied sharply. Bonnie knew that I was on to her act. I resumed eating Bonnie's pussy and fingering her ass and much to my surprise she put my cock back in her mouth. Bonnie drank the remaining cum from my cock and sucked me until I was hard again. She had a number of orgasms as I ate her pussy. Now that I was hard again it was time to take her ass. There was no trickery or forcefulness this time as I had her get on all fours. I got the lotion from the bathroom and applied an ample amount to my cock and her asshole. I sawed my fingers in and out of her ass and pussy as I prepared her for another ass reaming. Bonnie cooed with the dual action of fingers in her ass and pussy but I could tell she was still reluctant to be butt fucked. I knelt closer to her and placed my cock at the entrance to her asshole and pushed ever so slightly. I watched as her little rosebud opened up to accept my rod and the cock head cleared her sphincter. Bonnie had her head down on the bed turned to one side and she grasped the bed covers with both hands. I slowly fucked her ass trying to make this session last as long as possible. I loved watching my cock slide in and out of her beautiful shapely ass. As hard as I tried to prolong her butt fucking I felt my orgasm building rapidly. I thrust into her plunging my cock in all the way and released my seed into her bowels. Rope after rope shot out of my cock to fill her ass with my warm semen. Bonnie was fucking me back and I realized that her hand had traveled to her pussy and she was getting herself off as I flooded her ass with my spunk. The two of us collapsed on the bed with me on top of her and my cock still buried in her ass. I could feel her ass muscles milking my cock as her buttocks contracted and relaxed under me. I pushed up on my elbows to keep my weight off her but I kept my hips in contact with her shapely ass until my cock softened and slipped out. We both fell asleep and never stirred again. Bonnie and I continued our affair for almost a year. I knew she was dating other guys but she surprised me on night when she told me that she had become engaged to get married. Of course she waited until after our marathon of sex before telling me and showing me her ring. Then she said that it had to be our last night together. I agreed and we fucked once more that evening before I left. I never did see Bonnie after that. NUMBER 2 – CHARLOTTE I selected Charlotte as my second favorite not because she had a great ass but because she loved anal sex. The other thing I loved about Charlotte was that when she was in the mood it didn't make any difference where we were, in someone's house, in a public place or in my car. Charlotte, although she preferred to be called Charlie was one of the corporate groupies at our company. This story takes place in 1971, a year when everyone was sexually promiscuous and condoms were rarely used. There was a bar that all of us hung out at called the Oasis which also sponsored one of the softball teams I played on. I also played for another bar and our company team. All three teams had many of the same ballplayers and we actually did very well in our leagues and in tournaments. Softball tournaments were huge in the Midwest back then and we were in at least two a month. It was at a softball tournament that I first hooked up with Charlotte. Charlie was a 28 year old brunette with brown eyes, about 5'5" and 120 pounds. She was not the prettiest of girls but she wasn't ugly either. Charlie had served in the Army before she worked at our company so she was no virgin and no stranger to brief encounters. We had won our first two games in a 16 team double elimination tournament and we had the whole afternoon off. We were not scheduled to play again until 8:00 PM that evening in the third round of the winner's bracket. My friend Al had his girlfriend Ginger at the game. Ginger was good friends with Charlie who had accompanied Ginger to the game. Al invited me to join him and Ginger at her house for lunch and a few pops between games. Ginger introduced me to Charlie and she confirmed Al's invitation. When we arrived at Ginger's house her first words were that we all had to take showers before we used the beds. I was surprised but not shocked at her announcement. I knew Al was banging Ginger on a regular basis so it was not a surprise that the two of them would jump in the sack. Charlie just smiled at me and said, "Come on I'll show you where the guest shower and bedroom are that is unless you'd rather watch TV." "Lead the way," I replied not wanting to pass up an opportunity for some afternoon delights. Charlie and I stripped down and entered the shower. She had a large birth mark on her shoulder that she was embarrassed about but I quickly put her at ease. I started to soap up her tits, ass and pussy but she stopped me. "Let's save that for the bedroom. Ginger doesn't like it when the shower runs too long," she told me. Charlie had obviously done this before at Ginger's place and I followed her advice. We washed ourselves quickly and then went into the bedroom. Charlie lay on the bed and opened her legs for me. She held up her arms and welcomed me into her body. "I had been hoping that we would get a chance to make it together someday," she whispered. Slowly, I moved into her. Charlie opened beneath me, enveloping my penis tightly. Her cunt was like a fist as she clenched her vaginal muscles. She squeezed me as I moved within her. "Charlie," I groaned, "You are really tight." She moaned in response, "Your big cock feels so good. Fill me up with it." I thrust into her deeply and I felt the head of my cock pressing against her cervix. "Oh Walt," she sighed with her eyes closed. I felt her vagina contract around my cock. She climaxed again with a shudder and a long moan and she urged me on, "Fuck me baby. I can take it, I want it." I grabbed her hips in my hands and began to thrust in and out as I pounded her pussy. My heavy bloated testicles slapped against her ass as my cock drove into her hot pussy. "Yes, oh yes," she gasped as her body rose to meet me. The bed was now rocking with the force of our fierce, animalistic fucking. Her legs clamped around my waist as she screamed her release. Her pussy grasped my cock, squeezing it and milking it as I fucked her. I moved my hips against hers and buried my cock to the hilt within her. Her quaking pussy erupted into orgasm again as I rocked my cock slowly, grinding the head against her cervix. I felt my orgasm building in my balls and I knew that any second I would be spewing my seed into her womb. I felt my semen travel from my scrotum through my cock as I came deep inside her flooding her waiting warmth with my load. Neither one of us could speak as the pleasure was so intense. I collapsed on her and she wrapped her arms and legs even tighter around my body. Not wanting to crush her I rolled off her as my cock deflated and slipped from her cum filled cunt. We rested together as we talked for awhile. Charlie knew that I was fucking a few girls from the office and she had told Ginger that she would like to make it with me, which is why Ginger invited her to the tournament. I learned that Charlie had been married but was divorced in the Army. She also told me that she was not at all into oral sex either giving or receiving. Charlie reached down and stroked my cock as we talked and I fondled her tits and played with her pussy. Before long we were turned on again. I pulled her legs apart and let her guide my cock into her pussy. I eased my thick cock into Charlie's tight cunt and worked it slowly until I was balls deep in her pussy. I knew that with her tightness that she could probably feel every ridge and vein of my cock touch her vaginal wall. Charlie gasped again when I hit bottom. As I fucked her slowly I made sure that my cock never lost contact with her clit. Charlie stiffened as she orgasmed and then grunted and groaned through multiple orgasms as her body was rocked with one climax after the other. As I pounded her pussy my cock moved easily in her now soaked pussy. Charlie stiffened one more time, screamed and then went limp with her final orgasm which was the most intense of the day. Once again I rolled off Charlie and this time she rolled over on her stomach. I caressed her ass and teased her between her ass cheeks. I searched for her nether hole as I massaged her bottom. I finally reached the object of my desire and I rubbed juice from her pussy into her asshole. She lifted her hips slightly as I worked her firm ass cheeks. I pulled her buns apart slightly and stared at the cute little aperture. I traced my finger over the ridges of her now swollen sphincter and watched as it seemed to pulse and throb under its own accord. I scooped more juice out of her pussy with my fingers and pushed it into her asshole. Charlie's hips bucked in response to my probing. I loved anal sex and I loved to watch my cock slide in and out of a hot ass. I was hoping that Charlie was into anal sex. As my finger entered her channel she gripped it with her sphincter muscle. I continued to finger fuck her ass adding more natural lube from her pussy as needed and eventually I added a second finger. Satisfied that she was well lubed I straddled her hips and guided my slick cock into her pussy to coat it with juices and then I eased it into her ass. My cock head slipped past the moistened sphincter and the spongy head disappeared into her ass. Her anal ring snapped closed behind the cock head and I marveled at the sight before me. I only had the head of my cock in her and she lifted her hips and pushed back obviously wanting more. "Not too deep at first and then go deeper," she whispered. My cock felt bigger than it ever had as I eased more of it into her anal passage. I watched as it stretched her open and slid easily in her slippery hole. I continued my slow penetration until the entire length of my shaft was balls deep in her ass. Charlie gasped and grabbed the bed sheets as I hit bottom and then moved her ass in time with my thrusts. "Let's fuck on our sides," she rasped. I rolled both of us to our left side and settled into the spoon position with my cock still buried in her asshole. My left arm came around and fondled one of her tits and tweaked her nipples as my right hand sought out her pussy. I pushed two fingers into her pussy as I fucked her ass and played with her tits. Charlie was going wild as her orgasmic, constricting muscles gripped me firmly. We fucked slowly as she arched her back and we fitted together perfectly. Her gasps were intermittent and interrupted with cries and sobs of pleasure. Her ass was so snug that I wondered how the semen ever got out of my cock. I fought to hold back my ejaculation as long as possible but the undulating walls of her asshole were just too much. I felt the familiar boiling in my balls and I thrust into her as the first blast of cum exploded into her rectum. I barely heard her pleas for me to fill her ass with cum as her contractions milked every drop from my cock. I continued to fuck her slowly and I enjoyed the new feeling of warm semen surrounding my cock in her sheath. "I love the feel of your warm cum in my ass," she sighed as my cock remained nestled in her hole. Charlie told me that she loved anal sex and that sometimes she actually preferred it to vaginal sex. She said that she still wanted to cum and she preferred a cock shooting a load in her ass while her clit was being rubbed. We remained in the spoon position for quite awhile. I think we even dozed and we were awakened when my deflated cock slipped from her ass. Charlie rolled toward me and smiled as she whispered. "That was some great sex today, you are a good lover," she said softly and then, "Come on it's time to get up and get dressed." Charlie and I showered quickly and dressed. She told me that she first had anal sex in the Army and over time she had become addicted to it. Charlie told me that she liked anal sex as much as vaginal sex and sometimes even more with the right person. When we went into the kitchen Ginger had already put out some snacks for us. The four of us ate and then we returned to the tournament. We won our third game and the next day we would be playing in the winner's bracket championship. On Sunday we lost the first game and we had to play the team coming out of the loser's bracket. We beat them and then we had to beat the same team twice to win the tournament. We won the first game but then they came back and beat us in the championship game. It was tough playing four games back to back but that's what can happen in double elimination tournaments. All and all it was a good tournament for us. I was pretty tired as was the rest of our team so we passed on drinks at the Oasis and headed home. Tomorrow was a work day. I didn't see Charlie again until Friday that same week. Terry a girl who worked in corporate and her current squeeze Russ had a party at Terry's house. Terry was divorced with a couple of kids and the kids were spending the night at her parent's house. I went solo to the party since I wasn't really dating anyone. Another friend and ball player, Manny was supposed to meet Charlie at the party but he showed up with a last minute date named Cindy. Charlie was miffed but she kept her cool but by the time Manny had arrived just about everyone had paired off. I had my sights set on a cute thin blonde named Susan. I was drawn to her more by her outfit at first. She looked very stylish and she wore a cap that made her looked very British. I expected an English accent when I spoke to her but I learned that she too worked in corporate and she was originally from Kentucky. Charlie approached me and asked if she could speak with me just for a minute. I excused my self from Susan to speak with Charlie. "Can you meet me down stairs in a few seconds?" she asked. I told her I would but I noticed that she had been drinking heavy. I went down the stairs a few moments after her and she ushered me into the bathroom on the lower level. Charlie closed and locked the door, turned her back to me and pulled down her shorts. She was not wearing any panties under her shorts. It was a new style outfit with a halter top and the matching tops and bottoms were held in place by elastic. Charlie had elected not to wear panties under her bottoms and as I found out shortly she passed on the bra too. "I need you to fuck my ass before you head out with Susan," Charlie requested slurring her words a little. I dropped my pants and underwear and I pushed my fingers in Charlie's pussy. I moved my fingers from her pussy to her asshole for several minutes gathering her pussy juice and lubing her asshole. Then I pushed my cock in her pussy and got it good and wet before I eased it into her ass. Charlie grunted as my cock hit home and slid into her ass. We both fucked rapidly as I pushed her top up over her tits and played with her tits and nipples. I reached with one hand for her pussy and plunged two then three fingers into her quim. Charlie went wild with the double penetration and the manipulation of her tits. She soaked my fingers with her female juice as she had a string of orgasms. Then I felt my seed shoot through my cock into the depths of her ass causing Charlie to groan loudly. She milked my cock dry with her talented sphincter muscle and her hips thrashed uncontrollably ejecting my cock from her ass. I held her tightly and my wet cock brushed against her creamy ass cheeks. "Oh thank you, thank you," she cooed as her body calmed. I washed my cock off in the sink and then dressed and returned to the party. Charlie stayed in the bathroom longer after I left and I did not see her leave. It was ironic that Charlie and I had hooked up twice in other people's homes. I was talking with Susan again when Charlie left and not long after that Susan invited me to her apartment. Susan was my twelfth favorite described in an early story. It was a few weeks before Charlie and I hooked up again and it was quite by accident. I had worked late one night and I stopped off at the Oasis for a night cap. It was a slow night and I was the only one in the bar until Charlie came in. She had been out bar hopping and hadn't found anything to her liking so she decided to swing by the Oasis on the way home. She had not eaten dinner so I suggested that we grab a snack and a drink together. Charlie and I sat side by side at a bar table facing the bar. The bartender Dan was engrossed in the TV watching a ball game and getting caught up on all the scores. As we ate our burgers and sipped our beers, I ran my hands over Charlie's nylon covered thighs. She was wearing pantyhose under her red mini dress but no panties. I slid my hand between Charlie's thighs and covered her hose protected pussy. I rubbed her cunt through the hose and her pussy got sopping wet. We finished our burgers and beers and then left the Oasis. When we got out to the parking lot I asked Charlie if she wanted to sit in my car for awhile. "You better believe it, as worked up as you got me in there you better take care of me," she replied excitedly. Charlie and I got in the back seat of my two-door Grand Am and I immediately peeled off her panty hose. I lowered my pants and underwear to my knees and the two of us played with each other for several minutes. The Grand Am had louvered rear windows so it was impossible for anyone outside the car to see in the back seat. There was something very erotic about being partially clothed but still having access to each other. Charlie had her legs spread wide as I fingered her pussy and pushed her cunt juice into her ass. Charlie stroked my cock with her hand as I prepared her for another ass fuck. 14 Memorable Anal Encounters 05 I never knew anyone like Charlie who could get so wet during foreplay. My hand was sopping wet and within minutes I had her asshole coated with her own pussy juice. I positioned Charlie so that she was kneeling down on the back seat and I knelt behind her. I put my cock in her pussy and let it soak in her juices before I lined it up with her ass. Once again Charlie reminded me, "Not too deep at first and then deeper." I eased my cock into her asshole as she maneuvered her body to accommodate the anal penetration. Charlie had her head down on the car seat turned to one side and I watched her face grimace slightly as my cock made its way into her ass. Charlie moaned and groaned as I slowly fucked her going a little deeper in her ass with each thrust. Once I was all the way in I picked up the pace and fucked her until I flooded her ass with my cum. Charlie had her fingers buried in her twat and she brought herself off as I plowed her ass. When my hips stopped moving Charlie milked my cock with her anal muscle and then her hips gyrated as her own orgasm overtook her. I had to hold her tightly to keep my cock in her ass as her hips jerked out of control. My cock softened and I eased it out of Charlie's ass. I knelt there looking at her recently violated asshole and watched as my semen trickled out of her rectum. Charlie remained still for a few minutes with her red dress thrown up over her back and her ass on display. I had some paper napkins in the car and she used them to wipe the semen from her ass before she sat down on the car seat. "You definitely have the largest cock that has ever been in my ass. Do you know how big it is?" Charlie asked. "Well Karen measured it one time when she was blowing me and she said it was almost 8 inches long and just over 5 inches around," I replied. "It certainly felt bigger than that tonight," Charlie sighed. "At times I do feel thicker and longer but I have never thought about my size very much," I admitted and added, "I know that there are plenty of cocks bigger than mine." "I think tonight was one of those nights that you peaked and your cock is plenty big for me," she said with a giggle. Charlie did not bother putting on her pantyhose when I pulled up my pants. I opened the car door and we got out of the back seat. Charlie said that she was glad that she ran into me and that she would see me later, then she said goodnight and made her way over to her car. I watched as she got in her car and as she did her skirt flew up and flashed her bare pussy. After she left the parking lot, I drove home in a very sated state. It was at least another week before Charlie and I met up again. It was a repeat performance with me stripping off her pantyhose in the back seat of my car, lubricating her ass with her own juices and fucking her tight ass. It was exciting for me to strip off her hose and fondle her legs, pussy and ass. Charlotte seemed to like being without her panties and hose in the back seat of the car. I took my time with her, fingering her pussy and ass driving her crazy, until she finally begged me to fuck her in the ass. The final time it was another night at the Oasis and Charlie had had too much to drink. I put her in one of the booths toward the back to let her sleep it off and I told her girl friend Ginger that I would take her home later. Ginger and Al were anxious to get going that night and they didn't want to wait for Charlie to wake up. They thanked me and left and I joined Dan at the bar for a night cap. I didn't drink too much since I was driving and after a while I decided to take Charlie home. I picked her up and carried her out to my car all the while I hoped that she wouldn't get sick. I placed Charlie in the front seat and buckled her in. Charlie woke up and told me that she was staying at her sister's pad that night. She managed to stay awake and give me directions to her sister's place. Once we arrived at her sister's, I helped Charlie into the house and the guest room. It was late and I assumed that her sister was asleep in the other room. Charlie flopped down on the bed and I then had the urge to fuck her before I left. I moved over to the bed and stripped Charlie naked. I removed her blouse and bra, her shorts and panties and her shoes. Then I stripped down naked and got in bed with her. It was the first time that we were totally naked again since the very first time we had sex. I rolled Charlie to her side and she knew what was coming next. I scoop her female juice from her pussy and used it to lubricate her asshole. Charlie cooed as my fingers probed her pussy and lubed her ass. Then I placed my cock in her pussy just for few strokes to get it slick. I positioned my cock at her ass and gently pushed my cock into her. "Not too deep at first and then deeper," Charlie whispered those familiar instructions. I did what she asked and as I fucked her ass I went a little deeper each time. Soon I was balls deep in her ass and I picked up the pace. My cock felt longer and thicker than I could remember at that moment. I reached around Charlie with my left hand and played with her tits and rock hard nipples. Then I moved my right hand to her pussy and pushed three fingers into her cunt. Charlie was going wild and she was creaming all over my fingers as I plowed her ass. My cock was throbbing in her asshole and I felt my pending ejaculation building in my balls. One more deep thrust and I held my cock there as I exploded in her ass. My cock pulsated as streams of cum shot into her ass. Charlie instinctively clenched and unclenched my cock with her anal muscles. She milked every drop of cum from my cock. For some reason I stayed hard that night and I kept right on fucking Charlie's ass. I knew it would be a while before I came again so I pulled out of her ass and rolled her on her back. Then I pushed my raging hard cock in her pussy and treated her to an exhilarating fuck. I kept my cock in constant contact with her clit and I had Charlie writhing and trembling as a continuous string of orgasms rocked her body. Then I pulled my cock out of her pussy and rolled her back to her side and re-entered her ass. I pummeled her ass as I sought out my second orgasm of the night. Charlie's ass was loose and slippery from our combined juices but she was still snug enough around my cock. Once again I stiffened and fired a barrage of cum into her rectum. I could feel my cock pulsate again as it released a torrent of cum deep into her anal recess. We lay still for a few minutes recovering from the intense fuck session. I had forgotten about my cock in her ass until it had softened and slipped from her hole. I felt my wet cock drop on my thigh and I knew that cum was trickling out of Charlie's asshole. "I wish you could stay with me tonight," Charlie whispered. "Not tonight Charlie, I have to be up early in the morning. Plus I don't think you want your sister to find us in her guest bed in the morning either," I replied. Charlie just nodded her agreement and then I got up to get dressed. I dressed and left the house quietly and then drove home. It was the last time that I had sex with Charlie. Our company was going through some downsizing and Charlie was one of the casualties. She ended up taking a job with another company and she stopped hanging around the Oasis and her former co-workers. I still think back to our five anal encounters, two in my car and three in other people's homes. It was wild. NEXT CHAPTER The next and final chapter is devoted to my number one anal partner Cathleen. We had a five year affair and we had anal sex wherever and whenever we desired. 14 Memorable Anal Encounters 06 This story is dedicated to my best ever anal encounter. Not only was Cathleen the best anal lover she was by far the best sex partner I ever had. I was hired as a Senior VP to head up the IT division for a national firm headquartered in Chicago. I inherited the entire staff including the secretarial staff. Over the next six months I would make my assessments of the talent and capabilities of the staff before making any changes in personnel and restructuring the organization. During those six months I learned that my secretary Cathleen was very capable and very loyal. She demonstrated that she could handle confidential and sensitive information. She was definitely a keeper. During that time I didn't look at Cathleen as a sex partner as she was not that pretty. Although not unpleasing to the eye she just wasn't the type that I usually went after. Still she was very fit and presented herself very well. She always dressed tastefully and professionally and conducted herself accordingly. Cathleen participated in aerobics three days a week; Tuesday and Thursday evenings and Saturday mornings. Since we were so busy the first six months she would often return to the office after her aerobic class on Tuesday and Thursday to assist me. She would remain in her aerobic outfit and that was when I started paying attention to her very shapely ass. It had been difficult to assess Cathleen's figure when she was wearing her business clothes as she always wore long full dresses and skirts. However the first time I saw her in her aerobic outfit and the way the spandex hugged her curves, I appreciated her figure. Cathleen was 5'6" tall with short blonde hair. She weighed about 125 pounds and she was very solid. Her legs were muscular but shapely and her ass was to die for. Cathleen was small breasted but I was never turned on by big tits so it didn't matter. At 36 years of age she looked good. I was 6'2" tall and weighed a fit 190 pounds. I was in excellent shape from my years of sports activities and frequent visits to the gym. At 40 years of age I was proud of my physique and fitness. The day had come when it was time for me to present the Information Technology (IT) Strategic Plan to the senior management team along with my recommendations for organization change. Only Cathleen and I knew what the organization changes were being recommended and how it would affect the staff. The presentation went extremely well and I received approval for the five year plan and budget. I also received permission to make the organization changes necessary to implement the five year strategic plan. That afternoon I held a town hall meeting with the IT staff and revealed the organization changes. I informed the staff that Cathleen would be setting up a one on one appointment with me for many of them. That Wednesday evening I was still in the office when Cathleen stopped in and asked if I was up for a drink. "You look like you could use a drink," she observed. "You're right! Do you know of a good spot I don't want to go to any of the local watering holes," I replied. "There is a great bar near where I live that no one from the office goes to. They have great burgers too," she suggested. "Sounds perfect, I am hungry too," I agreed. "Why don't you follow me there but here's the address in case we get separated," Cathleen offered as she wrote down the address. We then left the office together and I followed her to the bar. She was right. It was a cozy place with great burgers. We discussed the day over a few beers and a burger and Cathleen shared her feelings about the new organization structure. She alerted me to a few staff members who would take exception to the changes but I was already prepared for them. After we finished our beers we left the bar and walked out into the parking lot. I walked Cathleen over to her car to be sure she was safe even thought it wasn't necessary. When we got to her car I thanked her for all her hard work. "Cathleen, you have been a gem these past six months and I thank you for all your hard work and your loyalty." Cathleen looked up at me and smiled. Her eyes twinkled in the street light and I had the urge to kiss her. I took her in my arms and kissed her tenderly. She kissed me back but it didn't last long. "Sit with me in my car for a few minutes," she whispered. I got into the passenger seat as Cathleen got into the driver's seat. We did not kiss again as I expected and Cathleen shocked me with her aggressiveness. She leaned across the seat and unbuckled my belt and unfastened my suit pants. Then she pulled my pants and boxer shorts down to my knees. I instinctively lifted my hips up to facilitate her. My cock was erect within seconds. "I have wanted to do this for a long time," she whispered right before she engulfed my cock in her mouth. Her head bobbed up and down a few times on my 7+" porker and then she lifted her head to speak again. "You have a nice cock," she said and then returned to sucking me. Cathleen was very accomplished in oral sex and I was as hard as a rock. Then she stopped sucking and I watched as she reached under her full length skirt and removed her pantyhose and panties. "I am really hot. I need to sit on your cock. I want to fuck you," she announced surprising me with her language. I had heard women use the words cock and fuck before, it was just that I had never heard it from Cathleen. Then with catlike movements and agility, she straddled my body and guided my cock into her pussy. She groaned as my shaft filled her vaginal cavity and I felt the wet silkiness of her cunt. Cathleen rode me hard and fast and it was obvious that she was only thinking about her own orgasm. "Oh. Oh, this is going to be a quick one," she gasped. I looked at the car windows to see if anyone was spying on us but the windows were steam covered and it was impossible to see in or out. We did make quite a sight though as we fucked in her car. I was still in my suit jacket, shirt and tie with my suit pants and boxer shorts down below my knees. Cathleen's dress was gathered around her waist and I held on to her shapely ass while she did all the work. "I'm going to cum. Hold me!" she called out excitedly as her hips flailed on top of me. I held her by her curvy ass and then my arms moved up and wrapped around her upper body as she screamed into my shoulder. Her screams were muffled in my shoulder as her body shook and shivered with the intensity of her orgasm. Cathleen eventually stopped moving and relaxed in my arms briefly before easing her body off of mine. She sensed that I had not cum and in her desire to pleasure me she lowered her mouth back onto my cock. It was obvious that she did not mind the taste of herself as she gave me an incredible blow job. Cathleen fondled my testicles and ran her finger along my perineum as she swirled her tongue around my shaft. I felt my discharge building within me and I warned her that I was about to cum. Cathleen never removed her mouth from my cock and she received a mighty discharge. Ropes of semen shot into her mouth splashing off the back of her throat but she never missed a beat. Cathleen stayed glued to my cock until she had sucked every last drop of semen from my shaft. Tingles ran through my body and I felt my toes curl up inside my shoes. It was the best blow job ever. We relaxed for a few minutes and then got dressed the best we could. At least I did. Cathleen opted to stuff her hose and panties in her purse. Then we opened the car windows and let the air in. I waited until the windows were clear and it was safe for Cathleen to drive home. We said goodnight but didn't kiss. I walked back to my car and then watched as Cathleen drove off. I then drove home all the while wondering where this would go. I had clearly crossed the line by having sex with a company employee and my secretary at that. SEX IN THE OFFICE The next day Cathleen arrived at the office on time and she went about her duties as normal. There was no mention of the car sex that we had the night before. She did not bring it up so I decided not to mention it either. We both went about the day in a business like manner. That evening after her aerobic class Cathleen returned to the office wearing her snug spandex outfit. I observed her move around tidying up her desk and doing some filing before she left for home. As I watched her I focused on her round curvy ass and I got a boner just from looking at her. It was all I could do to keep my hands off of her. I wanted to pull her into my office and pull her pants down and bare her ass. However I knew better and I restrained myself although it took all of my will power. If we hadn't had sex the night before I would have never thought of doing that. "Good night, see you tomorrow," Cathleen said as she poked her head in my office. "Oh, good night, don't forget that we are doing your performance review tomorrow," I reminded her. "I won't. I'm looking forward to it," she replied and then waved goodbye. I returned to my work of finishing up Cathleen's performance review. I gave her an outstanding review as she had been invaluable during my first six months on the job. I recommended that her position be raised one level and that she be given the title of Administrative Assistant. That would be consistent with the other Executive's former secretaries who all now held the title of Administrative Assistant. I was sure that Cathleen would be pleased with her review and promotion. The next day I conducted Cathleen's review at 10:00 AM thinking that we could go to lunch afterward and celebrate her good news. Promptly at 10:00 AM Cathleen was seated adjacent to me at the small conference table in my office. I had locked the office door so that we would not be disturbed. I opened the booklet containing Cathleen's performance review and my evaluation of her work. As I read through each category and began to explain my rationale for the rating, Cathleen just stared at me the entire time. She seemed disinterested in what I had to say. About half way through the review she reached over and took my hand in hers. I stopped talking and looked into her dreamy eyes and sensed that she wanted something to happen. "I know that you gave me an outstanding review and I appreciate that and the promotion. I want to show you how much I appreciate it," she whispered and added, "Stand up in front of me." I stood up and remained still as Cathleen unbuckled my belt and unfastened my suit pants. She took her time and then lowered my pants down past my knees. I could feel my cock rising to the occasion and my boxer shorts tented in evidence of my excitement. Cathleen smiled as she reached for my cock and then she fondled it through the fabric of my boxers. I groaned as she gently squeezed my shaft. Then she slowly pulled my boxers down my legs allowing my stiff cock to get caught in the waist band. She continued pulling my shorts down until my cock cleared the waistband and bobbed in front of her face. Cathleen lowered my pants and shorts all the way to my ankles and then she pushed my dress shirt and tie up out of the way. I rolled up my shirt and threw my tie over my shoulder and watched as she lowered her mouth to my cock. Cathleen looked up at me as she moved her head up and down on my cock and the expression on her face was one of pure ecstasy. She gently held my balls in one hand as she worked her magic on my cock and I did not last long at all. "Cathleen, I'm going to cum," I whispered. Cathleen, however, as she had done Wednesday night in her car stayed glued to my cock. I exploded in her mouth with one of my most massive ejaculations ever. It seemed like I kept cumming for minutes although I knew it was over in a matter of seconds. Cathleen sucked me dry again as she had done the first time. She kept my cock in her mouth for a seemingly long time after I came and she nibbled on it teasing me and driving me wild. I had tingles running through my body and I had to push her head away as I began to feel weak in my legs. I steadied myself by holding onto the table and then I began to redress. Cathleen smiled at me again and licked her lips in a very sexy way. I had pulled my shorts and pants back up and then I tucked my shirt back in and buckled my belt. I sat back down and smiled at Cathleen. "There isn't any provision for me to evaluate that skill on your appraisal form," I said jokingly and then added, "But if there was you would receive the highest grade possible." "Forgive me but that made me very hot. I need to cum," she whispered as she lifted her skirt and pulled her pantyhose and panties down just below her pussy. I looked at her neatly trimmed pussy for the first time and liked what I saw. Cathleen had a beautiful pussy with a little tuft of blonde hair just above it. I surprised her when I moved to my knees in front of her. Then I pulled her hose and panties down to her ankles. I did not remove them as I wanted her to be able to pull them back up if we were interrupted. I lifted her legs up and ducked my head under the hose and panties gathered around her ankles. Then I leaned in and placed my mouth on her pussy. Cathleen groaned when my mouth covered her cunt and then she emitted a squeal when I located her clit. Within minutes Cathleen was cumming and juicing my mouth. She covered her mouth with her arm and moaned into the elbow joint stifling her outcry. I continued to lick her pussy as she thrashed around on the chair until she went limp. Then I kissed the inside of her thighs and eventually removed my mouth. I lifted her legs back over my head and then sat back in my chair. Cathleen was in a euphoric state and she glowed in her pleasure. Cathleen then pulled her panties and hose back on and smoothed her dress as she stood up. She kissed me on the cheek and said softly, "That was an incredible performance review." "It certainly was," I replied. Cathleen then left my office. It was the first of many office encounters. In the weeks to come, we had sex in my office and at times in the car. Cathleen would give me marvelous blow jobs in my office. She loved to suck my cock and swallow my load. Sometimes we would play little games of seduction as if we were getting it on for the first time. Cathleen would come into my office, close and lock the door and come around to my desk as if to show me something important. As she showed me some document I would let my hand move up her legs over her pantyhose up to her ass. I would fondle her ass for awhile and then lower her hose and panties to her knees. I played with her pussy as I fondled her ass and she squirmed on my hands and fingers. "Yes, play with me. It feels so good. Make me cum, make me cum," she would repeat over and over. And cum she did soaking my hand with her female juices. She had to cover her mouth to muffle her moans of ecstasy. Then after she composed herself she would have me stand up and she knelt in front of me. Cathleen unbuckled my belt and lowered my pants to the floor. Then she slowly pulled my boxer shorts down my legs. She loved it when my erection got caught in the waistband of my boxers and my cock would spring forward as it cleared my shorts. Cathleen would then suck my cock until I came in her mouth. We also revisited the bar near her place and after a burger and a few beers it was sex in her car again. Sometimes we fucked and sometimes she just sucked my cock while she fingered her pussy. She would unbuckle my belt, unbutton my trousers and pulled them along with my boxers down to my ankles. As Cathleen pulled my boxers down over my balls she would lick and suck them before kissing her way up my shaft. Looking up into my eyes, she would slide her lips over my bulging head with her hand still wrapped around my shaft. Her tongue would swirl under the ridge of my crown as she sucked me deeper into her mouth. She would test her gag line and take my cock down her throat. She would pull me deeper into her mouth, pressing her lips tightly against me and sucking hard. The feel of my hard cock sliding between her lips and over her tongue would have me on the verge of a huge orgasm. Cathleen would often slip her hand into her panties and finger her dripping pussy. The smell of sex would be rampant in her car. When I felt my cock swell and I told her that she was about to receive my load. Muffled moans would escape from her throat as she eagerly sucked my dick awaiting my release. She would move her lips up and down over my shaft in rhythm with my thrusting motions. She would be drooling like crazy and I could feel the wetness running down my pecker onto my balls. My breathing would become more erratic as I was about to lose control. Cathleen would look up at me with those big eyes and nodded her head, letting me know she wanted to taste me and then she would cover my cock with her mouth just as I lost it. I always let out a soft grunt as I pumped stream after stream of hot cream into her mouth. She would move her hand under my scrotum to squeeze out the last few drops and then Cathleen would have her orgasm. The feel of my throbbing cock in her mouth, the taste of my seed and her hand in her cunt was just enough to set her off. The pressure in her lower tummy would gush out through her pussy and soak her fingers. My cock would fall from her lips and cum would drip from her lips and chin as her body would jerk and shudder in orgasm. Cathleen always looked up at me when she was done, blotches of cum glistened on her lips. The smell of pussy in the car was powerful. I would take Cathleen's hand and licked her fingers clean. I would then pull my shorts and trousers back up and dress the best I could in the confines of her car. One night when we were having a burger we discussed getting together in bed and being completely naked when we had sex. Cathleen didn't know it but I was very hot for her ass and I wanted a shot at it. She was married so we couldn't go to her place. I lived in an area where other corporate executives lived and I couldn't risk Cathleen being seen at my place. We discussed hotels and motels but I was leery of them as many of our vendors stayed at the ones near the office. That's when Cathleen suggested a romantic interlude motel called La Chateau. THE ROMANTIC INTERLUDE On our first trip to La Chateau Cathleen arrived before me and parked her car in the private spot adjacent to the room. I had given her my credit card to pay for the room. I parked in the lot which was secluded from the road and walked to the room. Cathleen was already naked when I arrived. She told me that this was the only room available as the ones with the Jacuzzi tubs were all taken. I looked around as I undressed and spotted the water bed, mirrors on the ceiling and walls. There was a TV with a porn station and a small mini bar in the room. Cathleen was naked in bed watching me as I undressed and I could tell that she liked what she saw. I liked what I saw too as it was the first time that we were completely naked together. I moved to the bed and I was anxious to get at her ass all the while wondering if she would let me fuck her in the ass. I loved anal sex and fucking beautiful shapely asses. I had always tested the water with the women with whom I went to bed. I moved her to all fours with her ass elevated and she placed her head on the mattress turned to one side so she could see me. I started playing with her pussy and her curvy ass lubricating her asshole with her own cunt juice. Cathleen moaned and cooed as I fingered her pussy and her asshole simultaneously. I tried to get her asshole wet enough with her juices and my saliva so that I could fuck her ass. Cathleen had not objected to the ass play so I knelt behind her and tried to insert my cock in her ass but it just wouldn't go in. Afraid of hurting her I tried more pussy juice and saliva for lubrication but to no avail. My cock just would not go into her tight ass. There are times when my cock feels bigger and this was one of those times. I was fingering Cathleen's ass when she spoke. 14 Memorable Anal Encounters 06 "Use some cream," she said urgently, "There is some in my purse." I got off the bed and retrieved the lotion from her purse. As I did I realized that Cathleen was going to let me fuck her in the ass. I returned to the bed and put an ample of amount of lotion in her asshole coating the tiny puckered opening of her anus and lubricating the rim. I added my saliva to my lotion covered cock and nestled my dick against the entrance of her anus momentarily before easing it inside her ass. I could feel my cock struggle to stretch the resistant muscles. My dick head burrowed in and her rigid passageway soon yielded to the determined action of my cock. Cathleen moaned as my penis filled her hole. "Go slowly at first it has been awhile," she said sexily. I fucked her with long and deliberate strokes until my cock was sliding easily in and out of her ass. I caressed her shapely buttocks as I watched my cock move in and out of her rectum worming around inside of her curvy ass. I caressed her small tits and tweaked her nipples as I leaned over her body and whispered in her ear, "Cathleen you have one hot ass, I love fucking you in your hot ass." My hands freely roamed over her body and I pulled on her hips drawing her backwards impaling her on my inflated member. I reached for her pussy to finger fuck her and diddle her clit but I found Cathleen's hand already buried in her womb. She was frigging herself frantically working herself toward an orgasm. Suddenly I felt my cock inside her ass swell up and I started pumping faster. Within minutes I knew that Cathleen felt the warm fluid being squirted inside her anus and she immediately started to cum herself. Her cunt walls convulsed around her own hand fucking her cunt as her anal muscles squeezed every drop from my spurting cock. I grunted as my whole body became stiff and I slammed my cock harder into her. Cathleen writhed around and her body arched off the bed as a climax of massive proportion tore through her loins. My cock slipped from her ass with an audible pop and I flopped down on the bed next to her. She surprised me when she covered my cock with her mouth and sucked any remaining cum from my tool. Cathleen then lay on her back, splayed her legs and pulled back the folds of her vagina. "I need to cum again. Eat my pussy, please eat my pussy," she pleaded. I rolled over and got between her legs. I put her thighs on my shoulders and lowered my mouth to her pussy. I took one slow lick as I flattened my tongue on Cathleen's mound. It felt so smooth and warm and I knew I had achieved the desired effect from her moan I know that Cathleen enjoyed it. I always enjoyed the taste of her and I kept licking and eating her. I pointed my tongue and burrowed into her pussy as it parted her labia my tongue was rewarded with the exquisite taste of her juice. Cathleen was obviously enjoying what I was doing as she reached down with both hands and spread herself wide making it so much easier for my tongue to explore her pussy. Cathleen was breathing rapidly and she moaned softly whenever I got near her hard clit. As I searched out her hard clit still just barely hidden she tensed and began to quiver. After I felt like I had teased her opening as much as I could with my tongue it was time to see her reaction when my tongue finally touched that treasured pearl. I burrowed my tongue as deep into her as I could and then I just sort of licked and sucked my way up. When I got to her clit I used the very tip of my tongue to push back the little hood. I flicked my tongue over it once and then used the tip to explore the folds of flesh on either side of it. Cathleen was now moaning and she used her fingers to pull her hood back as she arched herself so that her clit stuck out even further like a little cock. I nuzzled it with my nose taking in her scent and I licked it once more before I took it between my teeth and gently nibbled it. Cathleen went wild and started bucking and moaning loudly. She let go of her own fleshy hood and pulled my head to her pussy as she cried out in ecstasy. I sucked her clit as deep in my mouth as I could and Cathleen humped my face for all she was worth. I was excited that I was able to get her that excited and I sucked harder and played with her wonderful clit with my lips, tongue and teeth. I don't know exactly how many times Cathleen came but finally she collapsed on the bed, her body in spasms. I lay next to her and stroked her body my hands moved freely over her tits and pussy mound. She rolled toward me and embraced me and yelled for me to hold her tight. "Hold me, oh please hold me," she pleaded as her orgasm and spasms continued. Once she calmed down, we lay there for awhile making small talk and then Cathleen started stroking my cock. Cathleen added some body lotion as she kept stroking me cock and soon had me hard again. "I like playing with your cock. You have a big cock," she told me. "It's not that big," I replied although I was very comfortable with my manhood. "It's the biggest I have ever had," she said with a sultry tone. "Well there are plenty bigger than mine," I assured her. "If I had a cock I would be playing with it all the time," she giggled. We continued our conversation as Cathleen continued to stroke my cock. I learned that she had first been ass fucked before she was married. Cathleen had been working downtown Chicago at the time and she went out with two guys from the office. They took her back to their place and one fucked her ass as she blew the other guy. She took to ass fucking after that but she was very selective about who allowed in her ass. I shared with her my love for anal sex and some of my encounters. "All this talk and playing with your cock has got me hot again. I need to sit on your dick," she announced. Cathleen straddled my body and lowered herself onto me as she held my tool and aimed it at her vagina. My hard cock slid easily into her womb and she emitted a small gasp as it filled her hole. Cathleen rocked back and forth on top of me as I held on to her curvy ass. I stroked her ass cheeks and molded her firm buttocks in my hands as she picked up the pace fucking herself on my dick. Cathleen started moaning as she fucked faster and faster. I sensed her pending orgasm and then she yelled out. "I am going to explode. Oh, Oh hold me, please hold me tight," she screamed. Cathleen collapsed on top of me her body quivering from the intensity of her orgasm. I could feel her juices coating my cock as it remained buried in her womb. It took a few minutes for her to regain her composure and she just lay on me and cooed. Eventually she rolled off of me and lay on her back next to me. I was still hard so I took her ass again and fucked her until I released my second load into her rectum. After that we showered dressed and left the motel. A week later we revisited La Chateau again and this time Cathleen had gotten a room with the Jacuzzi tub. We entered the room and wasted no time taking off our clothes as the Jacuzzi filled with hot water and bath gel. Cathleen and I showered together before entering the Jacuzzi. We soaped each other up and played with each other's bodies being careful we didn't cum in the shower. Cathleen then douched both her pussy and her asshole. It was the first time I had ever seen a woman do that and it was very erotic. After showering we entered the Jacuzzi armed with a bottle of wine. I turned on the jets and we kicked back enjoying the bubbles and our first glass of wine. After awhile Cathleen leaned back into me and I reached around and stroked her cute titties tweaking and rolling her nipples in my fingers. I slid one of my hands down across her firm abs over her little tuft of hair and found her vagina. I played with the folds of her labia and then inserted my fingers in her pussy. I found her hard clit and rolled it between my fingers as I continued to tease her nipples with my other hand. As Cathleen got turned on, I moved her to the other side of the Jacuzzi and I had her lean over the edge presenting her shapely ass to me. Her ass always looked good but this time it glistened with water and bath gel and looked so sensual. I leaned over and licked Cathleen's pussy from behind driving her wild. Then I had the urge to tongue her beautiful ass so I swiped my tongue from her pussy up and over her bung hole and back to her pussy. She gasped out loud when my tongue touched her asshole. I really got into it and grasped both of her curvy ass cheeks and pulled them slightly apart so that I could get my tongue in deeper. I probed her pink aperture with my tongue as I inserted three fingers in her pussy. She started whimpering, gasping and directing the action. "Oh my God, do it again. Lick my asshole; stick your tongue in there. Eat my pussy, tongue my ass, oh yessssss," she cried out. I grabbed the bottle of wine and poured some in the crack of her ass letting it trickle down over her anus and pussy. I placed my mouth on her and drank up the wine swabbing her pussy and ass in the process. I repeated this several more times until Cathleen seemed to go into convulsions with her first orgasm of the evening. She collapsed back into my arms and I stroked her smallish tits as she recovered from the intensity of her orgasm. "Not in my wildest dreams did I ever think that you would ever tongue my ass or did I know it would feel so wonderful," she uttered in an exhaustive voice. "It just looked sexy as it glistened with water. Of course I remembered that you had douched and it looked so clean. It's also a great way to drink wine," I told her. We decided to get out of the Jacuzzi before we turned into prunes. We dried off and flopped down on the water bed. Cathleen began to stroke my cock into an erect state and then proceeded to suck on it. She loved to stick her tongue in the little hole and nibble on my cock head. This always made her hot and then she needed my cock in her pussy. She straddled me and aimed my cock in her hole and rode me until she achieved another orgasm. It was time for me to fuck her in the ass so I had her kneel on all fours with her gorgeous ass in the air. She always put her head on the mattress and turned to the side so that she could watch. She had the added benefit of mirrors on the wall and ceiling and so could clearly see the penetration. I broke out the lube and put an ample amount in her asshole. I fingered her ass and pussy at the same time. "I love the feel of your fingers in my ass and pussy together," Cathleen exclaimed! If there was one thing I liked besides fucking a lovely ass it is preparing an asshole for a good reaming. After several minutes of finger fucking her pussy and asshole I couldn't wait any longer and I had to get my cock in her beautiful ass. I removed my fingers and lined up the head of my cock at her moist puckered ring and pressed forward slowly. My cock head strained to pop through and she let out a little groan as the pressure from my iron hard dick forced her little ring to open like a flower and suddenly my large mushroom head slipped past the ring and into her ass. Cathleen let out a groan as her rear passage was stretched to accommodate my ample girth. "Oh you are going to make me like this more than the regular way," she gasped and shivered as I filled her fully and withdrew my penis slightly. I felt her ass tighten around me and I continued to slowly stroke in and out of her tight ass until all of it was tightly packed up her ass. Cathleen really began to moan and her whole body shook in anticipation of what she knew was coming. I began to slowly fuck her but soon picked up the pace as I penetrated her with long hard strokes that used the entire length of my thick cock. Cathleen was going wild as she loved the feel of my cock as it pulled out and then came crashing back in as my big heavy balls bounced off her clit. Cathleen was thrashing around uncontrollably, gasping and moaning with pleasure. When I reached underneath her to stroke her clit she exploded with her third orgasm of the night. I continued to hammer her ass with long strokes then suddenly I felt that familiar tension in my balls and I knew I was close. I began to piston my raging cock harder into her searing ass in search for my release, which also increased the intensity of her orgasm. She was yelling and moaning, clawing and scratching at the cover of the waterbed begging me to cum. "Give it to me, give it to me, give me your cum, cum in my ass," she begged. I felt powerful and dominant with my impressive dick stuffed up the beautiful ass of a woman who could not get enough of me. Cathleen lay submissively before me on all fours as I towered above her like some untamed animal with a strong sexual hold on her. I took firm hold of her hips and slammed once more full force into Cathleen's ass. I did that three or four more times and then I let out a loud groan as I emptied my seed deep into her bowels. I couldn't believe how much cum I produced as my dick continued to hammer into her ass. When I was finished I pulled out of her ass as Cathleen collapsed on the bed utterly spent. I slumped down next to her quivering body. I looked over at Cathleen and I noticed my seed oozing from her asshole. It resembled a natural spring as the semen just seemed to bubble up as she tried to relax her sphincter muscle. Cathleen and I got up, showered and returned to the Jacuzzi where we soaked our aching muscles. After the Jacuzzi I offered her a massage which she gladly accepted. I had her lay face down and worked her back, legs and buttocks. Not so surprisingly I got an erection as I massaged and fingered her ass again. Very surprisingly I came a second time that night when I fucked her ass again. After the ass fuck I rolled Cathleen over on her back and continued the massage this time working her tits, abs, legs and pubes. I finished her off with another thorough pussy eating which had her screaming my name and humping my face with her volcanic orgasm. After that we were really spent and had just enough energy to shower, dress and drive home. EROTIC MASSAGE Cathleen loved massages and I always accommodated her when she desired one. We always had the massage at the la Chateau. It would usually follow our foreplay in the Jacuzzi and precede our anal sex. We would dry off and then Cathleen would lie across the bed. I always massaged the front of her body first as she would be anxious to cum after the foreplay in the Jacuzzi. I had picked up some massage oils at a health store. Body lotion was okay but the massage oil made it very erotic. I loved the way her body glistened in the oil and Cathleen loved the way my hands glided over her body. As she lay on her back, I began with her shoulders and worked my way down over her tiny firm tits. She loved having her nipples twirled in my oily fingers. I continued down her body massaging her firm belly and then purposely bypassing her pubes. Next I started at her ankles and massaged her legs one at a time. I lifted a leg up to my shoulder and massaged her calves and thighs each time coming dangerously close to her pussy. By the time I finished with her second leg, she was incredibly turned on and anxious to cum. I ran my hands over her vagina and then probed it with my fingers. Cathleen could take no more and begged me to eat her pussy. I moved between her legs and fastened my mouth to her cunt. I took the erect little clit in my teeth and nibbled it gently. She grabbed my head and held it tight to her pussy as she juiced my mouth. Cathleen was always vocal when she orgasmed and she let out a cry of ecstasy when she climaxed. In the office she was always careful to muffle her cries of joy but in the motel she let loose for all to hear. I rolled her over on her belly and stared at her luscious ass. I never got tired of looking at her ass and I was anxious to fuck it once again. I poured more oil in my hands and massaged the backs of her legs working my hands up towards her buttocks. I held off massaging her ass and moved around in front of her. My cock was standing at attention and Cathleen took it in her mouth. As she sucked me I massaged her shoulders and back. Then I leaned over her and massaged her beautiful ass as she continued to suck my cock. I loved massaging her buttocks with the oil and I loved the way they glistened. Slipping my hand in her crack I teased her nether hole and then probed it with an oily finger. Soon I had two oily fingers sliding in and out of her ass all the while that she sucked my cock. It was time to take her ass before I came in her mouth. I moved back behind Cathleen and lifted her by her hips. She raised her ass keeping her head down on the bed. She had that way of arching her back that made her ass look very enticing. I covered my cock with oil and eased it into her ass. It went in like a knife through hot butter. Her ass look beautiful covered with oil but even more beautiful with my cock in it. I began to fuck her slowly enjoying every second of watching my cock slide in and out of her ass. Then I picked up the pace as I felt my imminent release. I drilled her ass and then with one final deep thrust I filled her rectum with my seed. Cathleen contracted and relaxed her sphincter several times milking my cock dry before she flattened out on the bed. I followed her down keeping my cock in her ass. We remained still for several minutes with our oily bodies pressed together. Then sensing that I was too heavy for her, I rolled to my side and my cock slipped from her ass. We lay still as we recovered from a very intense sexual episode. Eventually we went back in the Jacuzzi and let the warm bubbly water soothe our bodies. We stayed in the Jacuzzi for 20 minutes. Then we dried off dressed and left the motel. As I drove home I thought that the evening was one of the most sensual that we had ever spent together. From that night on a massage was included on our visits to La Chateau. RISKS AND REWARDS Cathleen always wore long loose fitting skirts in the work place so I decided she needed to shed the panty hose and wear something more appropriate for sex in the office. I brought a Victoria's Secret catalog into the office one day. Cathleen stood by my side as we looked at the catalog on my desk. As she paged through the catalog, I stroke her legs and ass again through the pantyhose. Then I lowered her hose and panties and played with her naked ass and pussy. Cathleen came on my fingers again and then she gave me one of her wonderful blow jobs. Afterward Cathleen selected a couple of items form the catalog to replace her pantyhose. That day at lunch time we went over to the Victoria's Secret store in the nearby mall and purchased nylons for her that had thigh high elastic tops. We also picked out some crotchless pantyhose that were very erotic. The panty hose had a waistband and two side panels attached to the stocking part. When Cathleen wore the new pantyhose her ass and pussy were bare and her ass looked great framed in the hose. Cathleen started wearing both the thigh high stockings and the crotchless pantyhose to the office along with sexy panties. It was very erotic when I slid my hands up her stocking covered legs to her bare skin just above the elastic tops. I would caress her bare skin before cupping and fondling her ass cheeks. Then I would remove her panties slowly dragging them down her legs and by the time I touched her pussy she was sopping wet. Cathleen would move to the chair in my office and place her legs on my shoulders as I ate her pussy and fingered her asshole. She would have intense orgasms and coat my face with her pussy juice. Then we would finish with another one of her signature blow jobs. We continued to have sex in the office, car and the romantic interlude hotel. We played games with each other taking turns being a slave and having to do what the other person demanded. There were times after aerobics that Cathleen would come into my office and I would pull her spandex down just enough to bare her ass. I would fondle her ass and finger-fuck her pussy. 14 Memorable Anal Encounters 06 There was no shortage to our imagination and willingness to have sex in public as well as private places. Cathleen, I was to learn, was somewhat of an exhibitionist. She loved to be totally naked in private places and was really turned on by the chances we took in public places. She loved it when I ran my hands under her skirt and inside her panties. She loved it when I pulled her spandex down to her knees and played with her buns and pubes. Cathleen could never seem to get enough of my cock. She loved to fuck me, suck me and have me fuck her ass. I was always concerned about the possibility of someone walking in on us even though the office door was locked. Staff from facilities and security had master keys and they could easily enter my office. It was one of the reasons we were never totally naked in the office. If someone did try to enter the office we could be dressed before the door opened. However, Cathleen wanted to expand our office sex beyond oral sex and fingering. So I picked up a door brace at the hardware store and we used that to keep any intruders out. Cathleen would enter my office close and lock the door and then put the door brace in place. Then she would stand next to me and hold her skirt up while I pulled her panties down and off her body. She then moved to one of the chairs in my office and sat in it with her legs splayed and her pussy on display. I moved over to her, dropped my pants and undershorts and put my cock in her pussy. I fucked Cathleen until she came several times. Sometimes I would cum in her pussy and other times I would fuck her ass. Cathleen would kneel on the chair with her skirt thrown up over her back and her beautiful ass pointed at me. I took the lotion from my desk and lubed her asshole and my cock and then fucked her until I filled her ass with my seed. I kept paper towels in the office and we would both clean ourselves up and then get dressed. Cathleen loved our games and she loved to act as if it were the first time each time. She would stand by my desk acting innocent and awaiting my move. I slid my hand up her leg and I felt her tremble slightly as we had played this game before and she knew where it was going. I let my hand ride up and down her stocking covered leg for a few minutes. Then I let my hand wander above her knee and past the top of her elastic top hose. Cathleen shivered as my hand touched the bare skin of her thigh. I caressed both of her thighs and I could tell that she was getting hot. The back of my hand brushed against her panty covered pussy and I could feel that the panties were soaked with her excitement. Cathleen moved her legs wider apart causing the skirt to tighten around her shapely ass. I rubbed her inner thighs between her legs and flicked my fingers over the material covering her vulva. Cathleen jumped involuntarily when she felt my hand on her pussy. "Your panties are very wet Cathleen. Would you like me to take your panties off you?" I teased her. Cathleen nodded and gasped, "Yes, please take my panties off." I eased her panties down over her buttocks, past her thighs and then let them slide to her ankles. Cathleen stepped out of them and I put them on my desk. I returned to fondling her ass and thighs and I soon had her squirming with desire. Cathleen moved her body as if she were trying to get my hand near her pussy so I slid it between her legs and stroked the outer lips of her labia. Cathleen squirmed under the touch and emitted a soft groan. I started to push Cathleen's skirt up but she stopped me and then she took it off. It was a wrap around skirt and she had it off in an instant. She looked so sexy standing there leaning forward slightly on my desk. Her magnificent ass was framed by her thigh high hose and her short blouse ending at her waist line. She actually looked hotter by keeping the blouse on. I ran my hands all over Cathleen's ass, thighs and pubes feeling her wet pussy. I slipped my finger into her vagina and then added a second one. I took some lotion from my desk and I pushed a finger between the cheeks of her ass and massaged it into her nether hole. Then I fingered Cathleen's ass and pussy at the same time. She was going wild with the double penetration and whispered to me. "That's it finger me, play with me. Make me cum, please make me cum," Cathleen pleaded in a deep whisper. I continued to work her ass and pussy and within minutes she had her first orgasm. Cathleen held onto the desk with both hands as her body jerked and spasmed with her climax. I worked my fingers in and out of her holes as she clenched and relaxed her vaginal and sphincter muscles tightening them. I pulled my fingers from her holes and I stood up behind her. I dropped my pants and boxers to my ankles and brought my rock hard cock to her buttocks. I let it rest against the hot flesh of her ass and I leaned over and whispered in her ear. "Where do you want it first today? Do you want it in your ass or do you want me to fuck your pussy first?" I teased her and then licked her ear. "Fuck my pussy first and then my ass. I want you to cum in my ass," Cathleen murmured. I then eased my cock into her pussy and fucked her from behind until Cathleen orgasmed once again. Then I moved my cock to her ass and fucked her for a short time before I unloaded my semen in her anal canal. Cathleen looked so hot leaning over the desk with my cock sliding in and out of her asshole that I just couldn't prolong my ejaculation any longer. I leaned over her as she milked my cock dry until it softened and popped out of her ass. Our sexual encounters in the office usually ended up the same way, with me cumming in Cathleen's ass but only after she had cum herself two or three times. Cathleen would surprise me from time to time. One day she leaned over the desk and as I ran my hands up her legs I discovered that she had already removed her panties. Another time she just walked in and immediately took off her skirt and panties. Without her skirt and panties she looked very hot in just her hose and blouse. There seemed to be no end to her creativity and willingness to try new things. However she never showed interest in adding another person to our encounters. THE SEMINAR We desired to spend at least one night together and wake up in the morning naked in bed. Cathleen suggested that I let her attend a seminar and that I could stay in the same hotel. I sent Cathleen to an Administrative Assistant / Secretarial seminar in Amelia Island, Florida. Then I took vacation days and stayed in the same hotel. We would be together for four days and three nights and I had just survived the first night. I rolled over in the morning and bumped into another naked body in the same bed. I slowly recalled the marathon of sex the night before and then I realized that I had a raging piss hard-on. A soft hand embraced my stiff member and held it gently and I remembered that Cathleen and I were in a hotel room together. "Good morning sleepy head. Did I wear you out last night?" she whispered in my ear as she fondled my rigid tool. I was still groggy as I had slept soundly and had some wild dreams. I yawned, stretched and made an attempt to get out of bed. "I have to pee," I told her. "Not until I get to ride you. I'm going to take advantage of your condition this morning," Cathleen remarked as she positioned herself to straddle my morning erection. Now I was trying to survive the morning as she rode my piss hard-on. She was determined to orgasm as many times as she could that morning until she could not cum anymore. "Don't pee in me," she teased as she rode my shaft like a woman possessed. "Don't worry, that is not a possibility," I answered remembering how difficult it was to pee with an erection. A few times in the morning I had to pee so bad that I tried but it wasn't until my penis softened to a semi-erect state that I could urinate. Even then it was difficult to control and I ended up missing the toilet with the first stream. I knew that my cock would stay hard as long as Cathleen rode me and that I would not accidentally pee in her pussy. She rode me hard and at times I thought that my bladder would burst but it held out. Finally after a number of mild orgasms she climaxed and collapsed on top of me. I wrapped my arms around her body and held her tight as she bucked and screamed. Cathleen was always vocal when she orgasmed and often she would cum so hard that it was scary. I had gotten used to her orgasmic behavior and I loved to make her cum as much as I could. After a few minutes she rolled off of me and flopped over on her back. "That was marvelous. We have to have more morning sex from now on," she sighed. I rolled out of bed and made my way to the bathroom with my erect cock pointing the way. I stood over the toilet and tried to aim so that when I finally urinated that I would not miss the toilet. It took several painful minutes for my erection to soften enough so that I could pee and then finally success. It seemed like I peed for at least two minutes and the pressure was extreme. Then I washed my hands and my penis before returning to the bedroom. Cathleen was waiting for me as she knew that I wanted to cum before she left the room for her seminar. If we had more time that morning I would have fucked her in her beautiful ass again. I loved anal sex and Cathleen had one of the nicest asses that I ever fucked. However she need to shower, dress and get going so I settled, if you could call it that, for one of her signature blow jobs. Cathleen was an accomplished cock sucker and I had been the recipient of countless blow jobs mostly in my office. However now were both naked in bed and I reclined on my back as she masterfully sucked my cock. I gently caressed her blonde hair as her head bobbed up and down on my dick. She would pause every so often and lower her mouth as far down as she could taking in most of my cock. Cathleen loved to do the deep throat thing always testing her gag line. It wasn't long before her expert cock sucking, fondling my testicles and tickling my perineum that she had me spurting in her mouth. Cathleen loved to swallow cum and she drank down every drop as ropes shot into her mouth. She kept me in her mouth until she had drained my shaft dry. Cathleen then became all business like and got ready for the seminar. She showered and dressed and then headed down to breakfast. "I'll see you around 4:00 PM," she said as she headed out of the room. "I'll be by the pool," I told her. "Behave," she teased. "You enough woman for me," I called back to her as she shut the hotel room door. I decided to go to the fitness center and work out before breakfast. After my workout I would shower, dress and go to breakfast. Then I would head to the pool and read the book that I had brought along. It was a book that I had been meaning to read and this would be a good week to do that. I knew that evening would be a repeat of the night before. First we would dine at a good restaurant and then we would have incredible sex back in the room. That day as I sat by the pool I had a difficult time concentrating on the book that I was reading. First of all there were a number of hot looking girls in skimpy bikinis around the pool who got my attention. However the main reason was that I was thinking about Cathleen and our five year affair. My mind drifted back to the start of our affair. The seminar at Amelia Island was the first time that we stayed together for any longer than one evening and it was great having morning sex with her. It was Tuesday afternoon and I had three more nights and three more mornings of hot sex to look forward to with Cathleen. I only stayed at the pool until 3:00 PM and then I returned to my room to shower. Cathleen called from her room at 4:30 PM and I told her to come to my room. I was dressed only in my gym shorts when she arrived. Cathleen smiled and grabbed my cock through my shorts, "Miss me?" she teased. "You know I did," I replied as I grabbed her ass through her slacks. "Let's fuck before we go to dinner," she said as she began to disrobe. In a matter of minutes after she arrived we were both naked in my bed and I was drilling her pussy. My cock was buried in her and I made sure that in stayed in contact with her clit. Cathleen orgasmed quickly but we kept right on fucking as I knew that she would cum at least once more. She wrapped her legs and arms around me and held me tight as she humped my cock. Then she exploded with another orgasm and it was intense. She cried out and bit softly into my shoulder to stifle her screams. "God that was great! Did you cum?" she gasped. "No, I can wait though. Let's get some dinner and then we can play some more after we eat," I answered. "Let's have room service," she suggested. "Fine with me," I agreed. We looked over the room service menu and made our selections. Cathleen then got dressed and returned to her to change clothes while I called in our order. Cathleen returned before the food arrived and we sat out on the balcony overlooking the ocean. Twenty minutes later the food was delivered and we dined on the balcony. I had ordered two bottles of wine as well knowing that it would be a long evening. After we ate we relaxed on the balcony finishing the first bottle of wine. Cathleen started getting frisky and she put her bare foot in my lap. Then she ran her foot over my stiffening cock as we drank our wine. I felt my cock harden under her foot but I made no moves to take the action further. "Take your cock out," she told me. I fished my cock out of my shorts and it stood up in an erect position. Cathleen had slipped off her other shoe and then she placed her feet around my cock. She rubbed both feet together up and down my shaft. It was a very erotic act and I decided to let her have her fun. I felt my balls tighten as they normally did right before I ejaculated. At that very moment I decided to cum on her feet. Cathleen had a very wanton look on her face as she jerked me off with her feet. She was really getting into it and I decided to surprise her with my ejaculation. Then without warning cum spurted out of my cock shot straight up and landed on her feet and shins. Cathleen giggled when I came but she went right on stroking my cock with her feet. She continued to rub my shaft with her feet squeezing cum from it. Then she spoke softly, "I douched my pussy and my ass for you when I was in my room." I knew exactly what she wanted without her asking, "So are you telling me that your bottom is squeaky clean and that you would like my tongue in there." "Oh yes," she said excitedly. We then left the balcony and headed to the bed stripping off our clothes. Cathleen never bothered to wipe the semen from her feet. She was anxious to be rimmed again and I was ready and willing. Cathleen got on the bed on all fours and wiggled her ass at me in anticipation. I got behind her and ran my hands all over her lovely buttocks and then pried them apart to expose her anus. I dipped my tongue between her cheeks and tickled her pink rosebud. I pushed my tongue into her taut anus and wondered how she could take my cock in there so easily. I licked Cathleen from her anus to her pussy and she went wild. I kept that up until so orgasmed and collapsed face down on the bed. Then I began to massage her body as she recovered. I used the body lotion supplied by the hotel and covered her back and shoulders with it. Then I worked my way down to her legs and massaged her calves and the back of her thighs. Next my hands covered her curvy buttocks and I massaged those glorious globes. I lifted Cathleen by her hips and she kept her head on the mattress and turned her face to the side. She had a dreamy look on her face as I fondled her buttocks and began to finger her anus. Satisfied that she was well lubed, I eased my cock into her ass and began to fuck her slowly. I was determined to take my time and last as long as I could. I loved watching my cock slide in and out of her shapely ass and I felt as if I could last for hours. I don't know how long I fucked her in her ass but by the time I ejaculated my thighs were burning. I fired several streams into her rectum and as she always did Cathleen milked my cock with her sphincter muscle. We were both exhausted so we moved into the spoon position and cuddled together. We fell asleep in that position and didn't move until morning. Then the insatiable rejuvenated Catherin was ready for morning sex. Once again I fucked her with my morning piss hard-on until she begged me to stop. Then after I relieved myself we fucked in the shower and I took her ass again. After the shower Cathleen dressed and returned to her own room to get ready for the seminar. It was a marathon as we had sex that evening, Thursday morning and evening and Friday morning before I left the hotel. I took an earlier flight on Friday then Cathleen as she finished up with the seminar and returned later. That weekend I chilled out at my condo as I had had more sex in four days than I would have ever imagined. It had been an unbelievable week. MOVING ON Over a five year period the affair continued. We had sex frequently at least once and sometimes twice a week. I was recruited by a firm in New York and accepted the position. Cathleen elected to stay behind even though I offered her a position as my assistant with the firm. We had a going away party on a Friday evening. After the party Cathleen ended up back at my condo with me and for the first time in five years we had sex at my place. Cathleen stayed through Sunday evening and we never left my condo. We had sex for two straight days and it was as if Cathleen wanted me to never forget our final hours together. I met some very pretty women in New York and had sex with some gorgeous ladies. As good as it was I still remembered the times with Cathleen. The sex with her was great but it was the risk and reward things that we did that made it exciting. I never had the opportunity for office sex again but I always recalled how erotic it was. I could still close my eyes and visualize Cathleen standing next to me with my fingers in her pussy and ass. I would never forget those days. The vision of her incredible ass has stayed with me to this day.