4 comments/ 112959 views/ 5 favorites The Education of Debbie By: walterio Introduction I am writing this to share an experience that happened recently in my life that still has left me both fulfilled and confused. I could think of no other way to describe it other than an educational experience that came very late in life. My name is Debbie and I am a very fit 50 year-old woman. I have short blond hair, blue eyes, and smallish breasts with a shapely ass that accents my 130 lb. 34-24-35 figure. I have been married three times and since my recent divorce I am in dire search for another man. My life is very empty without a man in it. In all of my relationships and marriages, the men catered to me and spoiled me. My sexual experience was fairly conservative in the bedroom. It was always a missionary position, an occasional doggy style and sitting on the man’s cock. I had never engaged in oral sex except to help my partner achieve an erection although I loved to have my pussy thoroughly licked. Most of my life was spent in the mid-west but my third marriage had brought me to Texas. Since that divorce I returned to my former mid-western town and resumed my life there. Most of my girl friends lived in this town and we spent a lot of time shopping, playing bridge, boating and dining together. My three closet friends all had successful marriages and in a way I envied them. My closet friend, Alice was due to celebrate her 36th anniversary later this year. She and her husband Walt had also both just turned 60 years old. I had known Alice and Walt for over 12 years and I was always secretly attracted to Walt, although I never had the nerve to flirt with him. Walt was a very fit 6’0” 200 lb., man. He had light brown hair that had started to gray giving him a very distinguished look. Walt was a former Force Recon Marine, Viet Nam combat veteran, an avid skier, scuba diver, tennis player and golfer. He also had a black belt in martial arts. He was very impressive and intimidating at the same time, although he was a perfect gentleman and not a bully as one may have expected. Walt had just accepted a big job in New York City. He planned to make this his last career move before retirement and it also brought him back to his roots since he was born in Manhattan. Alice although from New Jersey was not that familiar with New York but she was already starting to enjoy the amenities of the Big Apple. They decided to keep their mid-western home on the lake and also get an apartment in Manhattan. Walt commuted during the summer months and Alice lived in New York during the winter months. It was the best of both worlds. I was going to New York to do some sight seeing and I called Alice to see if she would be there. Alice told me that she had some commitments at home and would not be in New York while I was there. She also volunteered their apartment phone number and told Walt I was coming to New York in case I needed any assistance. As fate would have it the hotel botched my reservations and given the late hour I decided to call Walt. He as always was the perfect gentleman and told me to stay where I was that he would come and get me. He showed up in a taxi, picked me up with my luggage and had the cab take us to his apartment. He introduced me to the doorman and told him I was a good friend of Alice and would be staying a few days. We took the elevator up to the 37th floor and entered the apartment. It was a one bedroom, small but tastefully decorated. There was a great view of the East River looking north toward the Triboro Bridge. Walt told me to take the bedroom and that he would use the sofa bed. He explained that Alice used the closet in the bedroom and he used the one just outside the bathroom, that way he could always get up early, workout and shower and dress without disturbing Alice. Also I would have more privacy in the bedroom. I unpacked, threw on some baggy casual clothes and joined Walt in the living room for a nightcap. He opened a bottle of wine, which we finished while catching up on our lives before retiring for the evening. He told me to make myself at home tomorrow and help myself to anything in the apartment. I went to bed and slept soundly. Day One I awoke the next morning after having a wonderful night’s sleep. I called Alice and let her know what happened and how considerate Walt had been of my situation. The rest of the day I learned more about the apartment building and relaxed. The building was complete with any amenity one could ask for, a health club, sun deck, ½ acre garden, laundry dry cleaning, swimming pool and other services. Walt returned home from the office and told me he was taking me to his favorite Italian restaurant, which was only three blocks away. New York is amazing there were 155 quality restaurants within a ½ mile of the apartment building. We had a wonderful dinner, took a walk up to the Gracie Square section and then back to the apartment. The entire evening I felt myself becoming more attracted to Walt and I was sure the wine was having an effect as well. As I lay in bed that night I felt the absence of a man more than ever. I really wanted to be held and cuddled. My emotions got the best of me and I began to cry. I guess Walt heard me sobbing and knocked on the bedroom door and asked if everything was okay. I told him to come in and then I explained my feelings to him. I asked him if he would just lay down with me until I fell asleep. Walt Got in bed next to me, he was only wearing sleep shorts and I marveled at his still firm upper body. He certainly did not look 60 years old. I rolled on my side and he lay behind me with his arm draped over my body. I snuggled closer to him and held his arm to me feeling very secure. I moved my bottom into his groin and I could feel him getting hard. I couldn’t believe the size of his erection. I slipped my hand back between our bodies and felt for his hard-on, it was huge and so thick I couldn’t get my hand around it. I held it in disbelief trying to determine how large it was. My trance was broken when Walt asked me if I was sure I wanted to do this. I knew this meant to have sex and I turned to kiss him. Walt was not having anything to do with kissing and petting. He raised my nightgown above my chest, started sucking my tits and slipped a very thick finger into my pussy. In no time he had me dripping wet. His finger seemed thicker than any cock I have had in me and soon I was to experience the biggest cock ever. He got between my legs and lifted them over his shoulders, and then he proceeded to give me the best cunt licking of my life. I came multiple times before he crouched over me and shoved his cock into my sopping pussy. I had never felt so full in my life. He fucked the daylights out of me, pounding my pussy with his big dick and keeping his cock in contact with my clit the entire time. I lost track of my orgasms but I clearly had been totally fucked. My last climax was violent and I shuddered and pleaded for Walt to hold me tight. I no sooner had calmed down than he flipped me over and put me into the doggy position. He pushed his cock into me from behind and drove into me with long powerful strokes. As he fucked me from behind, he began to play with my asshole. He fingered my ass and lubricated it with my cunt juice and his saliva. Soon he had one of his very thick fingers buried in my ass as he continued to pound my pussy with his cock. I felt like I had two cocks in me at the same time. Walt reached under me and began to diddle my clit as he kept up the assault on my pussy and asshole. Soon I was coming again and I was really out of control this time. I shook and trembled with the biggest orgasm of my lifetime and by the time I came back to earth Walt had moved his huge cock from my pussy to my asshole. He had managed to get the head past my spincture and was slowly working it in and out. I told him that I had never been fucked in the ass and that I really did not want to do this. He laughed and told me that it was not my call and that he was pleased that he could take my anal cherry. He continued to add saliva and our juices as lube and pushed into my ass. It was painful but the humiliation was worse. I tried to pull away but he held my hips tight and continued to work his cock in until he was buried balls deep in my ass. My asshole had stretched to accommodate his size and the majority of the pain had subsided. He continued to fuck my ass sliding easily in and out of my bunghole as he told me how good I looked from behind with his cock penetrating my curvy ass. He started thrusting faster and I knew he was close to coming. Surely he is not going to cum in my ass I hoped. Walt stiffened and fired an ample amount of cum in my asshole. It felt like an enema and I felt constipated as well. He continued to fuck my ass slowly until his cock softened and left my asshole with an audible pop. God, I would never be the same. We both collapsed on the bed and soon fell into a deep sleep. Day Two There was no sleeping in the next morning. Walt woke me up by licking my pussy and again bringing me off before shoving his huge cock into me again. He fucked me soundly and thoroughly before shooting his cum into my pussy. He didn’t cum like those guys in the porno movies with their volcanic orgasms but he certainly did well for a 60 year-old. He showered, dressed and fixed us breakfast. We dined as if nothing out of the usual had happened He gave me guest passes for the health club and told me he would take to me to his favorite French restaurant tonight. Then he kissed me lightly on the cheek and squeezed my tit gently and told me to enjoy the day. I took a bath and then try to see my asshole using my mirror. I wanted to assess the damage. To my surprise everything looked normal back there but I still had a slight constipated feeling. I decided that I would not tolerate anymore butt fucking sessions. Walt came home and took me straight to bed. Once again fucking my brains out before he came in my pussy. Then we showered dressed and went to dinner. The restaurant was wonderful and Walt was well known to the owners here as he was to the owners of the Italian restaurant. Walt spoke both French and Italian at the restaurants. I was to learn later that he also spoke Spanish and some Japanese. After dinner we again went for a short walk and made idle chatter without any discussion about our sexual escapades. Later back at the apartment we had a nightcap and then we were back at it. Walt continued to drive me crazy with his tongue and cock and soon had me coming multiple times. Despite my objections and protests he fucked me in the ass again and filled my asshole with his cum. He continued to compliment me on my body and how good I looked. He loved my curvy ass and loved fucking me with his big cock. My problem was that I was becoming addicted to his impressive organ. I had considered leaving the next day but I couldn’t tear myself away from his cock and I had started to get used to it filling my asshole. Day Three Day three was like a repeat of day two. I woke up to another good cunt licking and fucking session. We had breakfast and Walt showered, dressed and went to work while I bathed, relaxed and contemplated what I should do. Walt came home from work and told me that we were going Spanish tonight. Since the Spanish restaurant didn’t start serving until 9:00PM that we would work out first. I never had a say in what the plans where, I was expected to do what I was told. This was a complete turnabout from the men who used to worship me. We worked out at the club and returned to the apartment. Once inside we both stripped down to shower. Walt then shocked me by telling me that there wasn’t time to fuck before dinner so that I would have to blow him. I told him that I didn’t suck cock and he laughed at me. He pushed me to my knees and pulled my face toward his cock. I refused to open my mouth and then he held my nose shut so I couldn’t breathe. When I opened my mouth to breathe he pushed his cock in my mouth. Once his cock was in my mouth he grabbed my ears so that I couldn’t pull away and he began to fuck my face. I gave up trying to fight it and accepted the cock in my mouth. I followed his instructions and swirled my tongue around his cock; I was straining to keep my mouth open around his thickness. I held his cock with one hand and moved my head up and down on him. He complimented me on my quick learning and told me how good his cock looked sliding in and out of my sweet mouth with my angelic face. Even though I felt total humiliation I kept sucking his cock. He started to swell even more in my mouth and I tried to spit his dick out since I didn’t want him to come in my mouth. No one had ever come in my mouth. He grabbed my ears again and I was helpless to move. He came in my mouth and told me to swallow his cum and not spill any. I drank it all down and was grateful that he didn’t come in volume any more. There was enough of his cum to fill my mouth and now I felt my humiliation was complete. Over the past few days I had been fucked to countless orgasms, lost my anal cherry and now had given my first blow job where I swallowed cum. We showered, dressed went to dinner and again had a wonderful meal and delightful time. The waiters all knew Walt and they frequently spoke Spanish over dinner. We walked directly back to the apartment since it was late. On the elevator ride up to the 37th floor, Walt removed my panties and finger fucked my cunt until we arrived at our floor. As we got off the elevator and walked down the hallway, he had his hand under my skirt and was fondling the cheeks of my ass. When we got inside our clothes came off rapidly and we fucked our brains out again. I had gotten used to the routine and after having my pussy thoroughly fucked, I automatically rolled over for my anticipated ass fucking. My asshole and pussy had stretched to handle Walt’s big cock and it was getting easier each day. Tonight Walt surprised by telling me to clean off his cock with my mouth after he came in my ass. I thought about protesting but knew it was of no use and I sucked his cock clean. Day Four We woke up the next morning and Walt surprised me by deciding to fuck me in my ass. He lubricated my asshole with some body oil and when he added his saliva to his cock it slid in easily. As he was fucking my ass thoroughly he leaned over my back and asked me if I was starting to like butt fucking. I just nodded my head yes as I did enjoy that monster sliding in and out of my asshole. He told me that he was glad that I enjoyed ass fucking and sucking cock since his wife Alice didn’t. I realized now that I was just his sex toy an object for his passion. My attention was then drawn back to my pussy and ass as Walt slipped first one then two thick fingers into my pussy. It felt like two cocks in me and I came violently just as Walt spewed his seed into my asshole once again. This time I didn’t have to be told I just swung around and took his cock in my mouth sucking it clean. To my surprise he stayed hard and told me that I did such a good job that I deserved a good fuck. He then proceeded to fuck me for what seemed like hours bringing me to multiple orgasms. He left me in bed because I was too tired to move. He showered, dressed and left for work. When he returned home that evening he had many packages with him. He told me we are eating Chinese in tonight because I felt you needed a break. I was grateful to be able to stay in that night. We dined with chopsticks and drank wine. The Chinese food in New York is marvelous, even the take out. After dinner Walt suggested we go down to the health club and unwind a little. We didn’t work out but used the sauna, steam room and Jacuzzi. Walt drove me crazy as he kept fingering my pussy, fondling my ass and tits while we were using these facilities. He had me suck his cock in the steam room and he had me sit on his cock in the Jacuzzi. Another new experience for me was having sex in public places. By the time we got back to the apartment I was so fucking hot that I couldn’t wait to be royally fucked. Walt did not disappoint me. In the bedroom he broke out some toys as he called them that he had picked up on the way home. He showed me a dildo that was about the size of his cock. It was very realistic looking with the mushroom head, veins and color. He also showed me an anal plug that looked like a spinning top with a handle on it. He told me that I would experience the feeling of being double fucked and even triple penetrated before the night was done. My pussy was already creaming in anticipation. I had reached total debauchery. Walt had me lay on my back as he greased up my asshole with the body oil. He then put a generous amount of lubrication on the anal plug and eased it into my ass. Once the fat part of the plug cleared my spincture the plug would stay in unless pulled out by the handle. Walt then positioned his cock at the opening to my cunt and slid his big dick into me in one smooth stroke. I truly felt like I had two cocks in me at the same time as Walt pounded my pussy. I could feel both his cock and the plug through my thin membrane separating my two holes. I could feel my orgasm coming on and I knew it would be a dilly. I screamed for Walt to hold me tight while I begged him to fuck me and hold me tight. As I started to tremble with my volcanic orgasm, Walt pulled the anal plug out of my ass sending me over the edge almost causing me to pass out from ecstasy. Next he placed me on all fours and slid his cock up my ass. He then added the big dildo to my pussy and again I felt like I had two cocks in me. He again fucked me through multiple orgasms until I nearly fainted. Then he announced time for your triple penetration. He lay down and had me get on top in a 69 position. I eagerly took his engorged cock in my mouth this time looking forward to his seed splashing off the back of my throat. He then pushed the anal plug into to my asshole and added the dildo to my pussy. As I sucked his cock for all I was worth, Walt maneuvered the toy cocks in and out of my asshole and cunt. The sensation was incredible and I truly felt like I was experiencing three men at the same time. Walt worked me to perfection, just as I started another countless orgasm he shot his load into my mouth. I knew he was worked up this time because it was his biggest load ever in my mouth. I felt three spurts of cum hit the back of my throat and I swallowed it greedily. My hips were gyrating as I came and Walt removed the dildo first causing me to jump in spasm and then the anal plug, which sent a tingling through my whole body. Walt then grasped my ass cheeks and pulled me to his face, gingerly licking my pussy and draining me of my juices as he caressed my curvy ass. I continued to hold his deflating cock in my mouth as I murmured “thank you” over and over. I was completely satiated. Day Five Walt and I fucked in the shower that morning. Over breakfast he reminded me that he would be heading back to his mid-west home for the weekend and would return Monday. He told me that I was welcome to stay at the apartment for the weekend and that if I was still here on Monday when he returned we would go to some other favorite restaurants. He was so laid back and polite when he left. Walt was a perfect gentleman on the surface who had introduced me up to a whole New World of sex. He told me that Alice wasn’t planning on coming to New York for the winter until mid-October and that I was welcome to stay until then if I wanted to. It was only August 28th and the thought of another 5-6 weeks with Walt was a little unnerving. I had the weekend to make up my mind. It is Friday night and I am still at the apartment. I am laying in bed now with the anal plug in my ass and I am thrusting the dildo in and out of my pussy bringing myself off to multiple orgasms. As I rest between masturbation sessions I try to contemplate a life without Walt’s cock. I decide that I am not ready to face that yet and I will await his return on Monday. The Education of Debbie Ch. 02 It is important to read the first chapter to follow the flow of this story. There will be more episodes of Debbie’s stay in New York if reader response if favorable. I want to thank everyone for their reinforcing comments and encouragement to continue this story. Walt returned to New York the following Monday and went straight to his office. When he arrived home at the apartment he told me that he was pleased that I was still there. He suggested a light dinner so we went to one of the local Irish pubs for beer and sandwiches. Once we returned to the apartment we went straight to bed and Walt gave my pussy a good licking and fucking, When I woke up in the morning I was lying on my stomach and Walt was lubricating my asshole with his fingers. When he realized I was awake he lifted my hips up so that my ass was even with cock and plunged his cock into my asshole. I was a little snug since it had been 3 days since my last ass fucking. Walt told me that he didn’t want me to forget about how good it was to have his cock in my ass. He came in my ass and immediately withdrew his cock and headed for the shower. I masturbated with the dildo while he showered. As he was getting dressed for work he told me that we would be dining late this evening and we would be going to a very special French restaurant. He told me to wear my black cocktail dress with the spaghetti straps tonight. Walt arrived home and we got dressed like two normal people without any sex prior to our going out. The French restaurant was magnificent in every aspect. We were seated toward the back of the restaurant. I sat in a leather bench seat and Walt sat in a chair across form me. The food was exquisite and the wine was superb. I felt more lightheaded then normal but very relaxed. As the night went on, I realized that we were the only patrons still in the restaurant. The waiters were fussing over me and continually serving me more wine. Walt was speaking French with all of the staff as they scurried about our table. Two of the waiters sat down on either side of me and began to caress my bare arms and shoulders. Then they began to kiss my neck and face. When I protested one of them held the wine glass to my lips. Each time I protested their advances I was fed more wine. All of a sudden I realized that the top of my dress was in my lap and the two waiters were fondling and kissing my tits. They were saying Mademoiselle has beautiful breasts as they continued to turn me on. I became aware that the table was moved away from me when I felt hands under my skirt pulling my panties down my legs. A third waiter had knelt between my legs, removed my panties and began to lick my pussy. I now had three mouths on me, two on my tits and one on my pussy. I was totally turned on. I heard the owner tell Walt that they were ready and I was led into another room that was very well lit. Time for dessert I was told as all of my clothes were removed. I found myself surrounded by five Frenchmen one was kissing my lips, two were kissing my tits, another was eating my pussy and the last one had his tongue in my asshole. They kept complimenting me; Mademoiselle has beautiful tits, Mademoiselle has a tasty pussy and Mademoiselle has a luscious ass. I was guided to the floor and I mounted the cock of a waiter on his back. Another cock was placed in my mouth and a third pushed into my asshole. I was triple penetrated and it would go on for hours. Each time one of men came in one of my holes that hole was immediately filled with another hard cock. I was to learn later that each of the five men came in each of my holes, which meant that I had a total of fifteen loads of come, five in each my mouth, my pussy and my ass. I don’t remember going back to the apartment but I woke up in bed laying on my side with Walt’s impressive cock buried in my asshole. He was watching TV as he fucked me in the ass. As my eyes focused I realized that he was watching a porn movie. However upon closer scrutiny I realized that it was I in the movie with the five French waiters. They had video taped the fuck session and Walt was watching it. I was amazed at how I handled those five cocks and I looked insatiable on the screen. The waiters were very well endowed and it looked as if I continuously had over 2 feet of cock in me at all times. Walt was extremely turned on by my performance and fucked my ass with abandon. He told me how good I looked taking all that cock in my pussy, mouth and ass. I could feel his hard cock expand in my ass as he neared his climax. I felt him shoot an excessive amount of cum into my ass and he continued to fuck me. I was surprised when he didn’t go soft and fucked me in the ass until he came again. We both fell asleep with his cock in my ass. I dreamt that night that I would have cocks in my mouth, pussy and ass for the rest of my life. I awoke in the middle of the night wondering what else was in store for me in the coming weeks and then fell back asleep. When I woke up later that morning, Walt had already left for work. I went down to the health club and used the sauna, steam and Jacuzzi to relax my aching body. Later that day Walt called me to see how I was doing and told me that we would dine in this evening and take a rest. After dinner we sat around and watched the video of me and the Frenchmen before going to bed. The video had us both turned on and Walt fucked me in my pussy bringing me to multiple orgasms as usual. Then he fucked me in the ass and then came in my mouth allowing me to taste all the juices. Walt announced that tomorrow night he would be taking me to his favorite Japanese restaurant. I giggled and told him that I couldn’t imagine Japanese men with cocks like the Frenchmen. He laughed and told me that I wouldn’t be seeing any cock at this restaurant. In fact the only cock I would sample tomorrow would be his. We both then went to sleep.