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My First Time

By Anon - Sep 19, 2004 - From first-time. First time sex story - Views - 14185 A first time sex story - Just about every man remembers his first sexual experience and I am no exception. I am glad to say however that mine was at the hands of an older woman, a very nice and experienced older woman. Sally my first woman was about 32 when I first became involved with her and I had secretly watched her as she sunbathed in her back yard wishing I could have sex with her for a long time. Sally was a trim blond with a nice figure and she was married. Sadly her marriage was not on good footing at the time and this combined with her husbands drinking must have been what precipitated our initial tryst.
On the odd occasion that Sally could not find a suitable baby sitter for her two small children ages 3 and 4 I would go over and sit with them in the evenings after they had been put to bed and were asleep. I must say that in all the times I sat for these kids they never gave me any problem and only occasionally would they wake up. Well I could tell that things weren't going well for Sally and her husband as many nights Sally would come home without him and I would see someone most times a woman drop him off the next morning. One night about 8:00pm Sally came home while I was sitting her kids and she looked very upset and asked if I would stay around a little while she took a bath because one of the kids was still up and she didn't want her to get scared if she found the house empty. I agreed and settled back to watching TV wondering if Sally was ok because she seemed so upset. Sally was gone quite a long time and I decided to go and look for her, so I quietly went upstairs and checked on the kids who were both asleep then went towards the bathroom to check on Sally. The bathroom door was slightly ajar and I could see Sally sitting on the edge of the bathtub staring off into space and softly crying. Sally had on just a thin robe which was open to the waist and I could see her full firm breasts with small pink nipples peeking out. The lower part of the robe was open across her legs falling further open to the sides of her firm long legs. I felt a strange mixture of sorrow, excitement, and fear as I looked at her sitting there obviously alone and very distraught. I moved closer to the door and looked between her legs seeing her neatly trimmed pussy which excited me more. By this time I was having a full blown hardon and I just stood there admiring Sally's beautiful body and wondering how I could get to see more.
I decided on a bold approach and with a bit of a tremble I opened the door and walked into the bathroom. I figured I could always say I thought one of the children was having a problem and thought I should check. But Sally didn't look upset and made no move to cover herself as I approached. I asked her if there was anything I could do and what was the matter as I looked directly into her eyes. Sally said it was a long story and it really didn't matter as I was not responsible for her problems. As she spoke Sally swiveled around to face me and her robe opened further allowing me to see both her firm tits and her legs splayed further providing me with a full frontal view of her pussy. Sally was great looking and I was very excited my cock standing at attention and clearly showing my excitement by the bulge in my pants. Sally must have seen my condition and recognized my excitement and confusion because she reached out and pulled me to her hugging me close. I was the surprised one when I realized that my right hand had slipped under her robe and I was cupping her firm tit in my hand. Sally didn't move and just kept holding me as I felt her breast with tentative strokes and felt her nipple harden with excitement. Sally slowly brought her hand around to my crotch and gently rubbed my cock thru my jeans as she asked me if I could stay a while and keep her company. Even thought I was scared my excitement overpowered me and I told her I would stay even though I would have felt more com comfortable peeking at her thru the open door than being in her arms. Taking me by the hand Sally led me to her bedroom and asked me to wait for her, her robe was open in the front now and I had a great view of her full firm tits with those stiff pink nipples and that golden triangle of fur between her firm legs.
I waited as she checked on her children and returned to the bedroom I thought I would cum in my pants as I watched her come thru the bedroom door her robe fluttering behind her giving me a full view of her naked firm body. Sally came to the bed where I was sitting and sat next to me taking my hand and placing it on her warm firm breast she asked if I wanted to make love with her. I stammered a bit but assured her I wanted her badly and would do my best to please her. Sally told me that we could only make love if I promised not to tell anyone about it and that she would get in a lot of trouble if I said anything to anyone especially my friends. I assured her I could keep our secret and that I wanted very much to make love with her.
Sally kissed me and began to take off my cloths starting with my pants which she undid with remarkable quickness and slowly pulled down rubbing my cock with her hand while she removed my shoes and socks pulling my jeans off. Sally pulled down my underpants and took my rock hard cock in her hand stroking it slowly and gently squeezing my balls. I felt like my cock was going to burst and told her she had to hurry or I would come in her hand. Sally pulled hard on my cock and then rammed my cock into her mouth sucking my dick for all she was worth. This was too much and I began to climax shooting my sperm into Sally's hot wet mouth as I tried to back away afraid She would be mad at what I had done. Sally just held me closer and grabbed my ass forcing my prick deeper into her mouth and sucked my sperm down her throat. Finally I stopped struggling and let her finish me with her mouth figuring she would be disappointed and ask me to leave. After Sally had drained the last drop of cum from my still stiff prick she pulled back and licked her lips and thanked me for giving her my sweet tasting cum. I was happy I had not ruined our lovemaking and begged her to get on the bed. Sally older and wiser than I told me to relax as we had plenty of time and stroked my cock showing me that it was still stiff and we would get to that part of our fun later. Sally moved me around and stripped off my shirt leaving me standing naked next to her. She hugged me to her and I felt her ripe breasts press against my chest as her stiff nipples burned into my flesh. Sally told me to take off her robe and I reached up taking the collar and pulled it back and off her shoulders letting it fall to the floor as I wrapped my arms around her hot body. Sally pressed her body into mine and reached around grabbing my ass and pulled me into her cunt. I thought I would cum again as my cock and balls pressed against her hot cunt. Sally held me this way for a while until I got com comfortable enough to move my hands down to her firm ass and pull her harder into our embrace. All the time Sally kissed me exploring my mouth with her hot wet tongue and lips which had just worked their magic on my prick.
Slowly Sally moved us onto her bed and had me turn on all the lights so that I could see her hot body clearly. As soon as I calmed down a bit Sally had me move up over her and feel her tits some more and she began to instruct me on how to make love. First she had me rub her nipples slowly making her moan with pleasure and bringing her nipples to full hardness so that they resembled tiny pricks. Next Sally took my hand and rubbed it up and down her hard taught belly until my hand rested in her blond bush. Sally spread her legs and had me pull back the outer lips of her pussy exposing her pink wet hole so I could see what a woman looked like. I loved it and wanted to put my stiff prick in right away. Sally stopped me saying first I would have to learn how to play with it and she reached down and showed me her erect clit telling me how sensitive it was and gently rubbing it with her fingers. I could tell this was really getting her hot because she moaned each time her finger crossed the head of her stiff little button. Sally took my finger wet it in her mouth then rubbed her clit with it moaning and thrusting her hips to meet my finger. As her passion grew I rubbed her cunt lips with my other finger and finally pushed my finger into her vagina making her moan even louder. Suddenly her hands were at her breasts pulling and twisting her pink stiff nipples and I was on my own.
I continued to push my finger in and out of her cunt and rub her clit until she climaxed wetting my hand with her love juices. Sally's legs twitched and jerked as she came and the muscles twitched thru her entire pelvic region each time my finger stroked her hard clit. Sally told me I was great and that made me want her even more, my cock was throbbing hard and ready to fuck her but Sally had other ideas. Sally pulled my head down to her tits and had me tongue and suck her tits and nipples while I continued to finger her hot twitching pussy. While I was driving her nuts with my fingers and my mouth Sally started to stroke my ass pushing her fingers into the crack of my ass and massaging my cock and balls with her other hand. Sally pulled my ass cheeks apart and rubbed her finger on the rim of my anus slowly circling my butt hole and driving me crazy. All of a sudden her finger was in my ass slowly pushing in until her whole finger was up my asshole. Taking my cue from Sally I rubbed her anus and slowly pushed my finger up her pulsing rectum until it was buried as deep in her asshole as my other finger was in her cunt. I began a slow stroking motion ramming my fingers into her cunt and asshole with slow steady strokes. Sally was moaning quite loud now and she released her grip on my cock and pulled her finger out of my ass grabbing my head and pushing it down her lith belly until my tongue was just inches from her erect hard clit. I knew what she wanted and extended my tongue until it contacted her hard clit and instinctively began to suck and lick her pleasure button making her cry out with desire and pleasure. I kept pace with my fingers in her holes and soon Sally was in the throes of another climax her hands had returned to her nipples and she was pulling them fiercely as she climaxed over and over again until she lay moaning her pleasure.
I was beside myself with desire and I pulled her legs up opening her hot wet pussy and gave her a few more licks before I moved in between her wide spread thighs my hard cock sticking out like a flag. Sally looked down and reached for my cock guiding me into her tight slit as I rammed my cock in with one deep thrust. Sally put her legs on my shoulders and I rammed my cock into her tight hot pussy for about five minutes before she and I climaxed together. The look of pleasure on her face made me feel like a king and I continued to pound her pussy until my cock got hard again. Sally was as surprised as I was that I could come back so soon and begged me to try another position. Giving way to her experience I pulled out of her cum ladened pussy and waited for her to get into position. Sally got on her hands and knees facing away from me and told me to fuck her cunt from behind as I moved in on her exposed cunt and ass she told me this was called doggy style. I bent down and licked her cunt and rubbed my thumb over her puckered anus making sure to nip at her still erect clit. Sally was now demanding my cock so I brought my hips level and close to her ass and she reached between her legs grabbing my dick and forcing the head into her hot slit. I lurched forward burying my cock in her dripping cunny. Sally told me to hold still and let her do some work as she rammed her cunt back and forth impaling her sweet twat on my stiff meat. I could see her hand work fanatically on her stiff clit as she banged my cock deep into her slippery cunt. Seeing that look on her face I reached forward and grabbed her tits and began to twist and pull her hard stiff nipples. Sally began to climax again as she reamed herself on my prick and I pulled and twisted her hot nipples.
Sally and I climaxed again together and I filled her sweet hole with another load of my creamy sperm. Sally was too fucked out to go on right away and she pulled me up next to her and held me close as we recovered from our pleasure. I a few minutes the closeness of her body and the musky smell of her sex had me hard again and Sally reached down and took my cock in her hand saying that she had never seen such a horny young boy. I was glad I pleased her and wanted very much for the night to never end. Sally reversed her position and began to suck my cock as she massaged my balls and played with my asshole. Since I was looking right into her cunt I pulled he legs apart and began to tongue her cunt and clit and finger fuck her well lubricated cunt and asshole. Sally said there was one other thing she wanted to teach me tonight if I was still willing. I told her I was ready for anything and Sally looked up and told me to fuck her in the ass. I thought of how tight her anus was on my fingers and wondered if I could force my cock into such a tight hole but Sally had been right every other time so I thought I should try. I said ok and asked what I should do. Sally told me to lay back and watch as she bent down taking my prick into her mouth and sucking me harder than ever before. My dick was like iron by the time Sally was ready and she move up to a squatting position over my cock and grabbed it rubbing the head from her clit to her asshole and back for a while. Then Sally placed the head of my cock firmly at the entrance to her asshole and slowly pushed down forcing my cock into her vise like asshole. Sally continued to probe her hot anus with my cock until my whole cock was buried in her twitching rear. Sally then took my hand down to her cunt and forced two fingers deep into her hot wet slit and placed my thumb on her clit. I could hardly stand the pressure as she began to stroke herself on my cock and fingers and I had all I could do to remember to rub her clit with my thumb. Suddenly Sally cried out and I knew she had reached orgasm when her cunt and anus clamped around my fingers and cock making me shoot my load up her packed asshole.
After this Sally and I rested and played with each other for a while before I took a shower and she made me promise to sit for her more often. I readily agreed and our relationship kept up until I went off to college. I was very lucky to find this lady and our relationship helped her thru some difficult times as well as giving me a great sex education. Even after her husband and her got on better footing she and I saw each other at least once ever few weeks but more on those meetings later.

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