I had a pretty wild high school and college experience, but by the end of college I had a steady girlfriend and felt ready to settle down. We were long-distance for a good chunk of the time we dated since she was still in school, and even when we got engaged. It was fine, I told myself, I was a grown-ass adult and I could take care of myself during the time apart, and it almost worked.

We were still a year out from our wedding and I wasn't going to see her for a few months, and life was stressful on a variety of levels. Suddenly, taking care of myself wasn't scratching the itch anymore. So I did the logical (ha) thing and went onto the Casual Encounters section of Craigslist (yes, I'm old). Much like its modern equivalents, it was an ocean of scams and spam - but there were a few times where you'd end up interacting with real people, and those IM sessions were fun. Definitely soothed the itch a bit because it was definitely out-of-bounds from a relationship perspective, but I told myself that it was just a thing in the moment and it wasn't going to change anything long term.

Then, one night, I'd been going back and forth with a girl who claimed to live in the same city as me. We'd had a few sessions before where we turned each other on and got each other off, but tonight she said she wanted to hook up. My mouth went dry, but I was once again horny out of my mind so in a haze of libido I said sure. We set a meeting place (a local donut shop), I parked my car, and then waited in the place for her to show up. Once she arrived, we chatted for a few minutes and then she said she wanted to take me back to her place, so we got in her car and away we went.

Five minutes and one staircase later, we were on the inner side of her apartment door making out, peeling each other's clothes off. She was cute, busty, and athletic...and possessed of an unearthly head game. She had me out of my pants and in her mouth in record time, her lips wrapped around me as she slid further and further down my shaft. After several minutes of her undivided attention, I said I wanted my turn on her, but she didn't want to let my dick go. Naturally, we compromised - she laid me out on the bed and straddled my face while she continued to go to down throating me. Having my face buried in pussy while feeling her nose on my balls and the moaning around my cock in her throat stripped away the last bits of moral composure I had left and I came up for air long enough to tell her that I needed to be inside her. She immediately came up off my cock, turned herself around, and got ready to mount me. I made to go for my pants to grab the condoms I had brought (safety first, kids) when she said the words that truly sealed my fate.

"I hate condoms...I want you inside me raw."

Obviously this was a horrible, terrible risk and not a good idea. Equally obviously I was feral at this point, and just nodded, jaw slack, as she lowered herself onto me, her tight pussy engulfing my swollen dick. And when I say tight I mean tight. I'm not a horse cock my any remote means, although I am rather girthy, and the grip on this girl left me amazed that she was able to just sink down on it in the smooth, fluid motion that she did and then proceeded to slide up and down me, gyrating her hips and using me to hit exactly the spots she wanted hit. She knew what she wanted, because she came quickly, shuddering on top of me.

This is where I regale you with the tale of my prowess in bed and the play by play of how I proceeded to use every one of her holes for hours until we were both spent - but while I have had those kinds of nights, this was not one of them. I was basically penis life support at this stage of the game. Any rational faculties I had were out of the window, and all my cock wanted was to finally cum. So I grabbed her ass, a cheek in each hand, and proceeded to piston up from beneath her, going balls deep over and over and over while she squeaked each time. She must have had some idea that I was close because as I became aware of a tightening sensation in my nethers, she leaned down and whispered those magic words, "Cum in me."

And boy howdy, did I do as I was told. I don't know where it came from (I was and still am a very consistent self-servicer), but I've seen cannoli in the North End of Boston that were less cream-filled than she was about forty-five seconds later.

The aftermath was...unremarkable. We got dressed, she drove me back to the donut place, I went home. Never got her name. Nor did I feel particularly guilty about it, and I've never mentioned it to my now wife over the fifteen-plus years of marriage that we've had together.

Nor have I told her about how turned on I get at the idea of railing a girl that isn't her, even though that's usually what I'm thinking about, even as I'm railing her.