1 comments/ 36823 views/ 8 favorites Chicago - My Kind of Town By: walterio PRELUDE 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 Catherine 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," Catherine remarked as she positioned herself to straddle my morning erection. It was not the first time that Catherine and I had sex in a hotel room but it was the first time we ever stayed the night in a hotel. We had been having an affair for over two years and most of our sexual activity was conducted in my office although we did go to a romantic interlude motel at least once a week. Even though we were both divorced and single we did not live together. You see, Catherine was my secretary and administrative assistant. Our company had a strict policy about nepotism and inter-office romances. I had sent Catherine 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. 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 Catherine 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. Catherine 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. Catherine 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 in her beautiful ass again. I loved anal sex and Catherine 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. Catherine 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 long brown hair as her head bobbed up and down on my 8" dick. She would pause every so often and lower her mouth as far down as she could taking in most of my cock. Catherine 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. Catherine 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. Catherine 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 Catherine and our two year affair. My mind drifted back to the start of our affair about two years ago. HOW IT ALL STARTED Two years earlier I, Cliff Watkins, 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 Catherine 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 Catherine 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. Catherine 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 Catherine'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. Catherine was 5'6" tall with long brown hair. She weighed about 125 pounds and she was very solid. Her legs were muscular but shapely and her ass was to die for. Catherine was small breasted but I was never turned on by big tits so it didn't matter. At 28 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 32 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 Catherine 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 Catherine 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 Catherine 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," Catherine 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 Catherine 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 Catherine 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. "Catherine, you have been a gem these past six months and I thank you for all your hard work and your loyalty." Catherine 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 Catherine got into the driver's seat. We did not kiss again as I expected and Catherine 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 8" porker and then she lifted her head to speak again. "You have a nice cock," she said and then returned to sucking me. Catherine 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 Catherine. 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. Catherine 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. Catherine'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. Catherine 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. Catherine 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. Catherine 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. Catherine 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. Catherine 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 Catherine to drive home. We said goodnight but didn't kiss. I walked back to my car and then watched as Catherine 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 On Thursday, Catherine 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 Catherine 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," Catherine 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 Catherine'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 Catherine would be pleased with her review and promotion. The next day I conducted Catherine's review at 10:00 AM thinking that we could go to lunch afterward and celebrate her good news. Promptly at 10:00 AM Catherine 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 Catherine's performance review and my evaluation of her work. As I read through each category and began to explain my rationale for the rating, Catherine 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 Catherine 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. Catherine 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. Catherine 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 through my tie over my shoulder and watched as she lowered her mouth to my cock. Catherine 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. "Catherine, I'm going to cum," I whispered. Catherine, 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. Catherine 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. Catherine 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 Catherine. "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. Catherine had a beautiful pussy with a little tuft of brown 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. Catherine groaned when my mouth covered her cunt and then she emitted a squeal when I located her clit. Within minutes Catherine 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. Catherine was in a euphoric state and she glowed in her pleasure. Catherine 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. Catherine 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. Catherine 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. Catherine 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. Chicago, My Kind of Town Cold, windy and snowy. That describes winter in Chicago, IL to a tee. I had just finished a conference "How to develop a Compensation Plan." Sitting at the bar in O'Hare International Airport (ORD), waiting to board my plane for a 4-hour flight home. The cab ride to the airport was late because of the Heavy snow falling. As we were stuck in traffic, I turned my cell on phone and called the Airport Hilton. The way the snow was coming down, I had a bad feeling that flight were going to be cancelled. Sipping on my Absolut and Cranberry, I watched the winter wonderland continue to pound the airport. Planes were slowly inching their way to the runway, which was stacked up like a can of Sardines. I turned to look at the flight status screen just outside the door, and it still showed my flight on time. Winter is short and darkness was fast approaching. The guy sitting next to me paid his tab and headed into the waiting area. They just paged final boarding for his flight. I ordered another when I heard this voice say, "Is this seat taken?." I turned and told her, "No ma'am, it's all yours!!" I turned back to watch the planes trying to maneuver around the snow, when my new bar mate said, "excuse me, is that a Cap Cod your drinking?" A Cap Cod I thought briefly, I haven't heard the name in years. I told her, "I believe it is. I just call it an Absolut and Cranberry, but I think your terminology is right." She told the bartender, I have one of those. "Single or Double Ma'am?" She said, "you better make it a double, I think it's going to be a long night." "Flight late," I said. "Of course! Aren't they always late out of O'Hare," she sighed. I thought about that, and she was right. When was the last time a flight was on time? I took another swig, and continued watching the planes slowly depart. I gazed at the status screen again, and this time what my bar mate had said, was a reality for me as well. Originally, my flight to Portland, Or (PDX) was supposed to leave at 5:00pm, and now it said scheduled departure, 6:30pm. "SHIT!!" My bar mate said, "Join the crowd. How late is your flight?" I muttered, "an hour and a half." She said, "your lucky, mine was scheduled to leave at 5:00pm and it's not going to leave until 8:00pm." "With flight time, that should put me home by 1:00am." She took another drink, and I just shook my head. "Well, I guess the good thing is tomorrow is Christmas Eve, and no work." She shook her head in agreement. "By the way, my name is Brian." I extended my hand to her, and she looked at me, extended her hand and said, "I'm Heather, nice to meet you." We started the normal bullshit conversation, where do you live, what do you do for a living, do you have children, etc. We were talking so much that I had forgotten about the time. I looked at my watch and it was nearly 6:00pm. I had heard no announcements on my flight. I glanced over at the status board, and noticed my flight was not listed. I thought to myself, what the hells going on. Heather noticed I was puzzled. "Flight delayed again," she said to me. "I don't know I said, it's not listed on the board any more." She looked at me, and I could tell it wasn't good. "Are you sure," she said. "Yes, I'm positive. I can't see it listed." She shook her head and said, "Brian, you flight has been cancelled. O'Hare started doing that a month ago. When flights are cancelled, they just take them off the board." "NO SHIT!!" I said. At that point, the bartender said, "can I pour you another sir."? I said, "YES, and you better make it a double." I excused myself to check out whether Heather was right. She was. I made it to the ticket counter and the agent told me because of the weather (dah!!) The flight I was supposed to be on originates on the east coast and it was cancelled. She booked me on the first flight out tomorrow. I headed back to the bar. Heather was still there. "Let me guess. The weather." I said, "the usual, the flight I was supposed to be on couldn't get hear because of the weather, and there are no other planes available." "Fortunately, I had this bad feeling in the cab on the way to the airport this afternoon, and I made a reservation at the Hilton." "So, I'm going to sit here and enjoy my drink, while everyone else scrambles to find a room." Heather said, "Where was that fight coming from anyway, New York?" "How did you know, I said." Heather looked puzzled this time, and said, "I didn't. I was just being a smart ass." I told her what the agent said, and she quickly turned to the status board. She turned back, shaking her head. "Bartender, give me another double, it looks like I'm screwed." I said, "no flight to New York tonight, eh" She excused herself, and headed in the waiting area. I took this time to call my wife and let her know the status. She was upset of course. When Heather returned, She pounded her drink and said she needed to hustle over to the Hilton. The agent had told her very few rooms remained. She shook my hand and off she went. I took a quick glance at her ass, as she was leaving, not bad for a 45-year-old woman who has three kids. I finished my drink, took one more final look at the planes struggling to make it to the runway, and thought, it's good I'm not flying tonight. As I entered the Hilton lobby, the line of people was staggering. Fortunately, there was a window for those with reservations. I walked right up, checked in and headed to my room. It was about 7:00pm, so I decided to take a quick shower, and head down for some dinner. Getting off the elevator, I noticed my bar mate Heather sitting on a couch by the door. I went over to her and said, "no luck getting a room tonight?" She looked at me and I could tell the doubles had taken effect. She shook her head, and said, "no rooms. I'm waiting for a cab to take me back into the city." "The downtown Hilton has rooms." I asked her if she had time to get some dinner before the cab arrives. Right then an announcement was made to all waiting for cabs that the heavy snow has made it difficult to get around and it could be up to two hours before any cabs make it out here. Heather dropped her head into her hands and just started shaking it from side to side. It was Christmas, and I was feeling no pain from the Absolut and Cranberry's. "Heather, at the risk of sounding like a pervert, the room they gave me has two queen beds, could I offer one to you?" She kept shaking her head in her hands, saying, "No, No, No.. I couldn't do that" "Come on, tomorrow is Christmas Eve, and It's a season of giving. Besides, by the time you get to your hotel downtown, it will be time to take a cab back to the airport to board your flight." She looked up at me. I took my key out of my pocket, and handed it to her. "Go up to the room, take a nice hot shower and meet me back down here for dinner." "Since my company is paying for the room, yours can buy us dinner. DEAL??" She extended her hand to grab the key, all the while saying. "A hot shower sounds great," I told her I would meet her in the bar. About thirty minutes had past, I was nursing another drink when I saw Heather at the entrance. WOW, she looked fantastic. She was wearing a pair of black stretch pants, and tight red sweater that accented her, shapely breasts. Those business suits are for the birds. They ruin a woman's body. I waved her over and commented as she reached the table, "you clean up pretty good!!" She ignored my comment, but I could tell she liked my eyes checking her out. Marriage and kids sometimes stale a physical relationship. She came over to me, kissed me on the cheek and said, "Thanks for being so kind. The hot shower felt great." Right then, the waitress asked if she could bring Heather a drink, she said, "I'll have one of those," pointing to mine. "You might as well bring me another," I piped in. A couple hours of more drinks, dinner and conversation past and we both decided we had enough. She picked up the check and we headed to the room. On our way out of the bar, I noticed it was still snowing. It looked like a foot had fallen. I grabbed her hand, and proceeded outside. "We don't get a lot of snow in Portland, and I was thinking about making a snowman." "Besides, the cool air will do us good." We raced out the door and immediately started making the snowman. I was rolling up the head, when I felt a snowball hit me in the ass. "Oh, you'll pay for that I said." I grabbed Heather and started to wrestle with her in the snow. Her sweater was hiked up a bit, so I decided to put some cold snow on her belly. As I did so, she slumped down and my hands went right up the front of her sweater and were now on her naked breasts. My first thought, boy those are firm. Then I came to my senses, pulled my hands away and said, "Heather, I'm sorry I didn't mean to do that." She said, "No big deal. Not bad for 45 year old broad, eh?" "Not at all," I said. "They're so firm, I didn't even know you didn't have a bra on. My cock was rock hard now. Rolling around in the snow and touching those breasts did the trick. She was now laying on top or me, and said, "talk about firm." She could feel my hard cock pressing against her thigh. She reached down, put her cold hand into my sweatpants, grabbed my hard cock and said, "fair is fair.." I couldn't help it; I just planted a big kiss on her. She responded with kissing me back. At that point the snow had stopped, and we were both wet. She broke the kiss and said, "lets go get out of these wet clothes." Not only being wet, we were both cold. We raced back to the room, stripped out of our clothes and head for the shower. We stood under the hot water, holding each other as our frigid bodies warmed up. Heather was the first to speak, "will you fuck me in the shower, my pussy has been wet ever since you made that comment of how good I clean up. I loved the way your eyes were undressing me." I broke our embrace, turned her around, and guide my hard cock into her. "Oh god that feels fantastic," Heather, moaned. She was right she was well lubricated. It was like a hot knife going through butter. I reached around and grabbed her tits. "Pinch my nipples," she demanded. "OH Yeah, that's it fuck me, squeeze my nipples, fuck me, fuck me." I couldn't hold out, "I'm going to SPURT," I screamed. I pumped load after load into her. "I can feel you cum in me. I'm so close. Fuck me faster.." My hands were on her hips, holding them as I was thrusting into her. She now started to pull at her nipples almost to the point where it looked like she was going to pull them off. I was still somewhat hard and began to feel her pussy contract. She didn't have to say it, but screamed, "OH YEAH, OH YEAH, FUCK ME, I'M CUMMMMMINNNGGG….." She pushed her has into me so hard I fell back onto the seat that's apart of the shower. My cock popped out of her and you could hear it. Cum started running down the inside of her leg. Most of it was mine, but she held her own.. She collapsed to her knees, and the water was still cascading down on her. She was barley audible, but I did make out, "it's been a while since I've had an orgasm that powerful." "Thank you!!" I told her I didn't think it was all me. We dried off, put on the robes hanging in the bathroom, and collapsed on the bed. "Since we properly introduced ourselves, can I ask you a question, Heather" "Sure," She said. "How often do you masturbate?" Heather said, "Not as much as I used to. Maybe once every couple weeks." "Have you ever massaged you G-Spot." I could tell she was puzzled. "I've heard of the G-Spot, but I'm not sure if I've ever stimulated it or my husband has either." I went to my overnight duffle bag, and grabbed out a very thin vibrator, specifically for the G-Spot. I brought it over to Heather and showed it to her. "What, you carry one around, just in case you find a slut like me?" I responded, "NO!! This is for my wife. I bought it downtown." "I just thought if you were up to it, you could give it a try." She sat, grabbed it out of my hand. She was diligently checking its girth. I could tell she was wondering how it was going to work. "Would you like some help," I offered. She gave that, "yeah, thanks" look. I turned it on, and told her to lay back. I untied her robe and let it fall to both sides of her. Her naked body was exposed to me. Her tits were firm. I would say about 34C's and a jet-black bush, perfectly trimmed. Her pussy lips were full and her clit stuck out, just enough to see it beneath the black hair. Her lips were still wet from the shower scene. I turned on the vibrator. Her eyes were closed, but I could tell she heard it buzzing. I started circling her nipples. She immediately got figgity and began a low moan. Her nipples were definitely sensitive. She grabbed the vibrator and started doing the same thing I was doing. I took the opportunity and ran my tongue up her wet slit. The second my tongue hit her dripping pussy, she let out a loud moan, opened her eyes, looked down at me and said, "are you going to lick me?" I gave her clit a couple of soft kisses, looked up at her and said, "Would you like me to??" "OH god yes!! My husband stop doing that many years ago, and I forgot how good that feels." I didn't answer her, I just began my assault. I licked each labia, up and down slowly. When I got to her clit, I slowly started making circles around it without touching it. She was still buzzing her nipples. She was alternating buzzing one and squeezing one. She was becoming very aroused. Her moans were more audible. After circling and teasing her, I took the tip of my tongue and started to lightly flick the exposed head of her clit. This sent her into another world. Her hips began bucking. I could tell she was near another orgasm. I stopped flicking it to tease her some more, when she stopped her moaning just enough to stay, "Don't stop baby, I'm so close to exploding. PLEASE DON'T STOP.." I wanted to tease her more, but, hey, it's Christmas.. I touched her clit with my tongue again, and she started bucking again. I flicked it faster and faster. She was moaning louder and louder. I had to hold her hips downs she was bucking so hard. She raised her head up to look at me flicking her, and that did it. She was over the edge. She started yelling, "I'M GOING TO FUCKING CUM RIGHT NOOWWWWW!!!!" She was holding my head to her clit. I could feel the vibrator on my head. I quickly grabbed it, while it was still buzzing and slammed it into her wet hole. There was no resistance. The G-Spot vibrator has the right size and length for its purpose. I could tell it founds its way to her G-Spot. She took her hands off my head and started grabbing for the bed. All she could say, "What the fuck are you doing to me??! What the fuck are you doing to me???" I was still licking her clit and I could feel the vibrator buzzing inside her on my tongue. What a rush!!! "WATCHOUT!!!!" She screamed. "That vibrator is making me pee." "I can't stop it, I'm going to pee all over your face." Of course, I knew it wasn't pee. If the G-Spot is massaged just right, most women can cum just like men. It's clear liquid and it tastes great… Her breathing became labored. "OH GOD!! He..re.. He.. re.. it comes. I'm going to pee." With that her whole body started shaking. I removed my tongue just in time to get a nice squirt of cum on my face. It wasn't a lot. Just enough to wet my beard. It took her five minutes to stop from convulsing. She kept saying, "I'm so sorry, "I'm so sorry." "I've never felt that before, but I just couldn't stop it." Listen to me, I said. "You didn't' pee. You came. It was actually cum!!" She looked puzzled. "Here taste," I said. I took a finger and rub some off my face and stuck into her mouth. "That's what came out of me??" I explained to her about the G-Spot. She finally mustered enough strength to sit up. She hugged me for what seemed like 20 minutes. All the time saying, "thank you! Thank you!" I responded, "my pleasure!" "Lets just say it was my Christmas present to you." With that we fell asleep in each other arms. Luckily, we set the alarm clock. It went off at 6:00am. Heather scurried out of bed to hit the shower. I dozed off again, thinking about last night. I was dreaming of her hot pussy. I could feel the warmth. I suddenly woke up. Heather had her mouth around my now hard cock. I wasn't dreaming. No wonder it felt so real. She was expertly sucking my cock and massaging my balls. I think my balls were still full from the G-Spot encounter, because I never got a chance to relieve them. It wasn't going to take long and we both new it. "Oh god Heather, that feels so damn good." I looked up and she winked at me. I was right there. I could hear myself saying, "Yeah, Yeah." I looked up at her one last time. "I'm at the point of no return, if you don't want me to come in your mo…." "AURRGHHHH" I pumped two or three loads into her mouth. She gently continued sucking me until my orgasm subsided. She removed her mouth from my now flaccid cock. She squeezed it a couple of times and licked the remaining cum of the tip of my cock with her tongue. All I could say was, "that was awesome!!" "What a way to be wake up." She moved up, kissed me on the lips couple times, and said, "Merry Christmas." I thanked her, and noticed the G-Spot vibrator on the nightstand. I grabbed it, jumped out of bed and met Heather at the doors as she was leaving. "Here, take this with you. It has your "NAME" written all over it." She kissed me and headed out the door. To this day, I always sit at the same spot in the same bar at O'Hare International (ORD), hoping I might see Heather again... Chicago - My Kind of Town "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. Catherine 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. Catherine 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 Catherine 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. Catherine would often slip her hand into her spandex 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. Catherine 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 Catherine 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. Catherine 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 Catherine'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. Catherine didn't know it but I was very hot for her ass and I wanted a shot at it. She had a roommate so we couldn't go to her place. I lived in an area where other corporate executives lived and I couldn't risk Catherine 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 Catherine suggested a romantic interlude motel called La Chateau. THE ROMANTIC INTERLUDE On our first trip to La Chateau Catherine 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. Catherine 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. Catherine 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. Catherine 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. Catherine 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 8" long and 5" around 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 Catherine's ass when she spoke. "Use some cream," she said urgently, "There is some in my purse." I got off the bed and retrieved the body lotion from her purse. As I did I realized that Catherine 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. Catherine 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, "Catherine 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 Catherine'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 Catherine 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. Catherine 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. Catherine 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 Catherine's mound. It felt so smooth and warm and I knew I had achieved the desired effect from her moan I know that Catherine 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. Catherine 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. Catherine 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. Catherine 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. Catherine 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 Catherine 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 Catherine 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 Catherine started stroking my cock. Catherine 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 Catherine continued to stroke my cock. I learned that she had first been ass fucked before she was married and divorced. Catherine 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. Catherine 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. Catherine 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. Catherine 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. Catherine 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 Catherine 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. Catherine 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. Catherine then douched both her pussy and her asshole. It was the first time I had ever seen a woman do that and it was kind of 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 Catherine 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 Catherine 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 Catherine'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 Catherine 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. "I surprised myself by going after your ass. I have never done that before but it just looked sexy as it glistened with water. Of course I remembered that you had douched and it looked so clean. It's 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. Catherine 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," Catherine exclaimed! If there was one thing I liked besides fucking a beautiful 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. Catherine 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 eight inches were tightly packed up her ass. Catherine 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. Catherine 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. Catherine 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. Catherine 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 Catherine'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 Catherine collapsed on the bed utterly spent. I slumped down next to her quivering body. I looked over at Catherine 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 anal muscles. Catherine 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 Catherine 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. RISKS AND REWARDS Catherine 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. Catherine 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. Catherine came on my fingers again and then she gave me one of her wonderful blow jobs. Chicago - My Kind of Town Afterward Catherine selected a couple of items form the catalog to replace her panty hose. 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 Catherine wore the new pantyhose her ass and pussy were bare and her ass looked great framed in the hose. Catherine started wearing both the thigh high stockings and the crotch less 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. Catherine 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 Catherine 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. There was no shortage to our imagination and willingness to have sex in public as well as private places. Catherine, 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. Catherine 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, Catherine 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. Catherine 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 Catherine until she came several times. Sometimes I would cum in her pussy and other times I would fuck her ass. Catherine 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. Catherine 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 about 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. Catherine 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. Catherine 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. Catherine jumped involuntarily when she felt my hand on her pussy. "Your panties are very wet Catherine. Would you like me to take your panties off you?" I teased her. Catherine 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. Catherine 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. Catherine 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. Catherine squirmed under the touch an emitted a soft groan. I started to push Catherine'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 cute 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 Catherine'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 into her nether hole. Then I fingered Catherine's ass and pussy at the same time. She was going wild with the double penetration and cried out to me. "That's it finger me, play with me. Make me cum, please make me cum," Catherine pleaded in a deep whisper. I continued to work her ass and pussy and within minutes she had her first orgasm. Catherine 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 anal muscles tightening herself on 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," Catherine murmured. I then eased my cock into her pussy and fucked her from behind until Catherine 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. Catherine 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 and 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 Catherine's ass but only after she had cum herself two or three times. Catherine 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 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 Catherine. I only stayed at the pool until 3:00 PM and then I returned to my room to shower. Catherine 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. Catherine 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. Catherine 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. Catherine then got dressed and returned to her to change clothes while I called in our order. Catherine 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. Catherine 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. Catherine 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. Catherine 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. Catherine 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. Catherine never bothered to wipe the semen from her feet. She was anxious to be rimmed again and I was ready and willing. Catherine 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 Catherine 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 Catherine 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 Catherine milked my cock with her sphincter muscles. 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 Catherine 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 Catherine 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 California and accepted the position. Catherine elected to stay behind even though I offered her a position as my assistant with the California firm. We had a going away party on a Friday evening. After the party Catherine ended up back at my condo with me and for the first time in five years we had sex at my place. Catherine stayed through Sunday evening and we never left my condo. We had sex for two straight days and it was as if Catherine wanted me to never forget our final hours together. I met some very pretty women in California and had sex with some gorgeous ladies. As good as it was in California I still remembered the times with Catherine. 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 Catherine standing next to me with my fingers in her pussy and ass. I would never forget those days.