I don’t recall the specifics, but I know I had been at a party. I’m pretty sure it was a kegger hosted by this Staff Sergeant that looked like Jessica Alba, but I can’t be entirely certain. I am, however, entirely certain that I was drunk off my ass that night. So was my lady friend, we’ll call her Ashley. Ashley was an attractive, fit, and somewhat sexually uninhibited young woman. Our sex life was awesome, we tried new things, we were awesome at the old, we did it often, and we did it everywhere; however, she was adamantly against the notion of anal sex.

Now I’m not an anal fiend or anything like that, but I am defiant. The moment she set the rule of “no rear entry” it became my primary objective. I always want what I can’t have. Time passed by and I slowly wore her down. Eventually, she tried it and, to her surprise, she actually enjoyed it. I had taken what I wasn’t allowed and was rather content with myself. I didn’t feel the need to press the matter any longer, so when she brought up the next day that she was rather sore, I agreed that we would only do it on the rarest of occasions.

A few months went by and we found ourselves at the party I was taking about. We were both incredibly drunk, and incredibly horny. No bathroom quickie or cramped closet romp would allow us the pleasures our hearts genitals desired. We made an exit, stage left, and cruised home. Our pace was slow and steady as we navigated the vacant, back road, shortcuts. As soon as we arrived at my house we started stripping, and had initiated the act a little early, in the form of your traditional stand and carry position in the carport. We moved into the house, stumbled through the kitchen, dodged the bar, and bounced off the hallway walls until reaching my bedroom door. “Hey dude, how’s it-oh fuck!” my roommate, Tom, saw my exposed ass as I fumbled with the door to my bedroom.

We ultimately ended up in my bedroom, on my bed, doing-the-do in the more conventional sense. Both of us are still extremely inebriated when I get the idea of trying anal again. I don’t recall exactly how I brought it up, but in my drunken state I’m sure it wasn’t far from, “Hey, babe, let me put it in your pooper.” Regardless, it worked, and she agreed. So I scurry over to the end of the bed, and she starts going through my nightstand looking for the K.Y. Jelly. She finds it and, somehow, between my penis and her ass, uses over half of the bottle. So were all lubed up, and in our positions, and I’m readying the approach. Five, Four, Three, Two, One, Houston, we have lift-uh oh, there seems to be a slight problem. Despite the gallon of oily lubricant that my penis is swimming in, entry is posing rather challenging. I’m pushing, but it’s not going in. I’m trying to be careful, because it is a rather sensitive area, and I’m pushing, and pushing. Finally! I start to penetrate, but the momentum and the lubricant play their evil deeds and, instead of taking it slow and easy, my entire penis slams into her pooper. I mean entire. Balls deep. I know immediately that the situation is ugly, and I don’t move. I’m just standing there, slack-jawed.

Aaaaaaaaaaaannnngggghhhh!!!!!!! She screams.
I scream.
Tom screams.

She screams again.
I scream again.
Tom screams again.

Tom comes rushing to the door, “Are you guys okay?!”
“Yeah, dude. Don’t come in!”
“Are you sure? What’s wrong?”
“Nothing dude, just don’t fucking come in.” I’m freaking out; trying to make sure my drunken Ashley isn’t bleeding all over my bed. She’s curled up, fetal position, bawling uncontrollably. I don’t really remember much after that. I think I passed out. All I know is that was the last time I had anal sex.