Accidental Anal [MF] | 2016

My favorite sexual encounter? It was when I was 20. I'm about 6'0", 180 lbs, not fit but not fat, curly brown hair. My girlfriend was about 5'4", 110 lbs. maximum, B cups, and an awesome ass.

I was staying at college over the summer, and my girlfriend since high school came up for the weekend. We went out on Saturday night, bar hopping, trying to find a place that would take our brand new fake IDs. Finally we found this empty sports bar, and spent the next few hours getting good and tipsy.

Finally, we went back to my dorm, groping each other the entire way, and ended up spooning in bed. Naked. Being summer, with no AC, we were sweaty... and both very turned on. I was nibbling the side of her neck, massaging her tits, and when I could stretch I could barely reach my entire arm down and tickle her clit. On her end, she was pushing back against me, just enjoying herself. So when my hard dick finally slipped inside of her after a lot of grinding, I was ready to fuck. At least I was until she asked me if I knew I was in her ass.

It's time for a little background. She never took my cum inside her before... when blowing me she would jack me off to finish, and she wouldn't go on the pill so it was condoms when we fucked. And she had always, always said she would never give up her ass. It was off limits, don't even think about it, one input only girl.

After she told me I was in there, I panicked because of how adamant she had been about no butt stuff. But when I went to pull out, she grabbed my ass, stopping me and told me it felt good in a weird way. So, the head of cock barely inside her, gripped by her tight anus, I slowly worked the rest of my cock in. Being a gentleman, of course I reached down and rubbed her clit like a madman, playing it like a little joystick. Each time she stiffened or pushed back against my thighs with her hand, I stopped entering her, but kept diddling. Eventually, I worked my whole dick inside her tight ass. Having my dick inside her for the first time without latex between us, her grip felt like an angel's mouth.

Her ass was so tight to start, I could only get a little range of motion, mostly grinding against her. But as she got more turned on and whimpered, she loosened up and started pushing back against me, trying to take control and keep my dick in her. We were so sweaty and that eventually it was like I was fucking her pussy, holding her hips and taking long thrusts, still spooning her. When she came, chanting "ohmygodohmygod", she came so hard, she almost blacked out. Fortunately, I had been holding off for so long (thanks to being so drunk), the contractions in her ass sent me over the edge. I thrust entirely inside, flattening her pillowy ass, and blew a giant load deep in her butthole.

We laid there for a minute, before she asked me to pull out. I did so slowly, and she winced as my cock slurped out of her well-used hole. I kissed her on the cheek, and then she got out of the bed and waddled to the bathroom, trying to keep my cum from dripping out of her.