Where it happened: Aunt's House
Langauge: English
Sex: Male
Rating: 5
Category: Straight
Well, when I was 15 I spent the summer at a cabin owned by my aunt and uncle. It was mostly a vacation, but I did odd jobs around the place – mostly landscaping and the like. My aunt and uncle had a huge house and for most of the summer there were lots of houseguests. Early in the summer, one of my aunt’s frients came to visit – her name was Dorothea and she was probably in her late 50’s or early 60’s. I remember that she was a very classy woman and that her husband had been killed in Vietnam. Dorothea was very “open” about her sexuality, and was the first woman who I had ever heard speak about sex. I know it made my aunt uncomfortable, but it totally turned me on. She was also very open about her body – she usually wore a loose cotton dress with no bra, and I remember seeing her breasts swinging under the dress.
Anyway, it all “started” one evening when I went out to the sauna house for a sauna. Usually the place was totally empty, and it took awhile for me to get it heated up (it was fire heated). Finally, the sauna was cooking and I was in there by myself (clothed!!) and the door swung open. It was Dorothea and she was wearing a towel. She said hello and asked if she could join me. “Sure”, I said. She sat on the same bench as me and we talked for awhile. She started to ask me sexual questions, like whether I’d ever had sex, or seen a girl naked. I was pretty uncomfortable, but really turned on at the same time. At one point, she moved her legs over so that they were up on the bench in front of her – she still had the towel on, but I could see glimpses of her pubic hair underneath the towel. Needless to say, I had a major hardon by this time, which was hard to hide as I didn’t have a towel with me. I could tell that she was looking at my cock, which made me really embarassed and my answers to her questions were getting really convoluted as I tried to hide my embarassment. I probably would have left, but there was no way to hide my “condition”, so I just waited her out.
After what seemed like ages, Dorothea asked me if I minded if she took off the towel. What could I say. She stood up, with her back to me, and let the towel drop. I just about died! She slowly, casually, folded the towel back up and then sat on it, all the while talking with me as if nothing had happened. At one point, she asked me if I wanted to take my swimsuit off, and I mumbled “No thanks”.
I kept trying to avoid looking at her body, but this was really, really difficult. My words were all scrambled, I was staring at the floor and the wall and I just couldn’t bring myself to look at her. Finally, after what seemed like ages, I felt Dorothea’s foot on my leg. Prodding me playfully with her toe, she asked me if I was embarassed. I told her that I was, to which she repled, “Don’t be”. “I want you to look at me if you want to – its OK”. Slowly, my eyes moved to her body and I saw her in all her glory. I remember her gently pinching one of her nipples while I stared at her. Then she moved her legs back onto the bench and slowly spread them, then put her hand on her pussy and slowly spread her lips. I remember how moist her pussy looked, and how I could see her clit poking out of the top.
Dorothea asked me again if I wanted to take my bathing suit off. I told her that I was too shy. With that, she slowly got up, leaned over to me (I still remember the feeling of her breasts sliding across my leg) and kissed me. We kissed for a few minutes while I ran my hands over her breasts and back then she guided my hand to her bush and pushed my fingers into her pussy with her hand. With her free hand, she began rubbing my cock and then she took it out of my bathing suit and began masturbating me. It only took about ten seconds before I knew that I was going to cum. I was terrified, and I told her “No!”, but it was far too late. She looked me in the eyes and said “It’s OK, go for it”. And I did – I had the strongest orgasm of my life, shooting bolt after bolt of my hot cum all over Dorothea’s stomach and legs. I remember as I was coming, she was staring at my cock and saying “Good boy, Good boy”. And then, when I was finished, she reached down and furiously masturbated herself, reaching orgasm in about five seconds until she fell on top of me, shaking and panting.
After we were done, she asked me if I was OK. I told her I was. She said, “No, I mean are you OK with all of this”. I said yes. She said “Good, I want it to be good for both of us”. She said “There’s a lot that I can show you Larry, if you want me to teach you”. I told her, sheepishly, that I did. She then kissed me on the cheek, and left.
That was the beginning of a two month education at the hands of Dorothea. That evening, we had sex for the first time. I was staying in an apartment above one of the garages, away from the main house. At some point in the middle of the night, Dorothea awoke me. “Just lie back and enjoy” were the only words she said as she pulled back the sheets. She kissed me, and then began kissing her way down my entire body until she reached my already hard cock. She put it in her mouth and I thought I was going to die. Then she slowly got up, pulled her dress over her head, and put my cock into her wet pussy. I managed to last about 30 seconds this time before pumping my hot load into her. Then again, this time with my cock still inside her, she masturbated herself to orgasm.
We had sex pretty much every day that summer. She taught me much, including controlling my orgasms, giving a woman head, how to have anal sex. She was not a particularly kinky woman, although she had a wonderful exhibitionist streak. At dinner, she would sit across from me and stare lasciviously at me – I could tell she was masturbating right there at the table. Towards the end of the summer, she confessed to me that my aunt and uncle were aware of what was going on, and thought that it was great. She told me that they were all swingers, and that it was my aunt’s idea that Dorothea “seduce” her nephew. Dorothea told me that my aunt wanted to fuck me too, or at least watch me cum (she apparently had a “thing” for watching guys ejaculate) but I told her that I wasn’t really that comfortable with that (I did fuck my aunt once about ten years later, but that’s another – very bent – story!).
And so that’s it – the story of Dorothea and the summer I lost my cherry. Any regrets? Are you kidding??
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