It was my junior year of college. It was a Saturday night and I was at a party at a friend of mine's apartment. The crazy part of the party was over and everyone had mellowed out and we were all sitting in the living room, drinking, smoking and chatting. I had been delighted to see that a girl from another school with whom I had become friends was at the party, and she and I wound up spending most of the evening together.
Neither of us were in any shape to drive, so we wound up sitting in an easy chair together in the back of the room and actually fell asleep for a few hours. When I woke up, it was about two in the morning and I awoke to see her looking at my face and smiling. We started kissing. She positioned herself so she was sitting on my lap and craned her neck back so we could continue kissing. I started rubbing her breasts through her shirt. She lifted her shirt up and I put my hand on her bare breast (she wasn't wearing a bra). Finally, I thought I'd go for broke and I slowly moved my hand down to her crotch. Not only did she not object, she spread her legs open wider to give me better access. I rubbed my fingers up and down over her jeans for a little while, then I unbuttoned and unzipped them and put my fingers inside, first caressing her hair, then rubbing her clit.
To my pleasant surprise, she lifted her hips up off my lap and pushed her jeans and underpants down to her ankles, then grabbed my hand and placed it back on her clit. I fingered her and she and I continued kissing. My other hand was all over her breasts. After several minutes she had an orgasm and did her best to keep it quiet to as not to wake up the half dozen or so other people in front of whom we were doing this.
She quietly asked if I had a condom on me. I said no. She seemed to think for a moment, then asked if I was "safe." I said yes, and she said, "Me too." She then asked if I'd like to go in her ass. I asked her if she liked that and she said yes. So I unzipped my jeans and pulled out my cock, which was hard as a rock. Her pussy and ass crack were both dripping with wetness, and I slipped easily between her buns. The tip of my cock pressed against her anus, and with just a gentle push it popped in and she settled her ass down into my lap, pushing it further up her ass. She groaned in what sounded to me like intense pleasure. I asked if she was okay and she said yes.
I didn't last very long! Maybe two or three minutes of us pushing against each other and I started to feel it coming. She told me to come inside and about thirty seconds later I did. I had one of the most intense climaxes of my life and I buried my face in her back to keep from crying out. I slowly pulled my cock out of her and put it back in my pants. She pulled her pants back up and curled up on my lap and we both went back to sleep.
The next morning she headed back to her own school (two hours away). I had hoped that a similar meeting would take place, but it never did. By the following year, we were little more than casual acquaintances.
That was the only time I had anal sex. I am now married, and my wife doesn't care for it (which she feels bad about, though I have told her she shouldn't). But I will always have that experience, which was pretty damn great.
And, yes, I know it was stupid of both of us to engage in unprotected anal sex and then not clean ourselves immediately afterward, but neither of us got sick. It's not something I would recommend to anyone.
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