My first anal experience was not what I would assume a typical first time to be, but who knows, maybe you’re just as drunk and slutty as I am. Let me preface this by saying that I legitimately enjoy anal. It is a semi-regular component of my sex life and it rocks. But I can say without a doubt that my first time was the strangest occurrence of events ever.
As with all my stories, this tale of drunk love started in the basement of a frat house. The theme was dirty Disney and I was absolutely killing my slutty Tinkerbell costume. I was by the pong table chatting with a sister when one of the boys came up to ask if I want to be his beer pong partner. Because I am insanely competitive and I love anything where you can win, I said yes. The only problem was that I am absolutely terrible at beer pong. We lost in like five minutes. Whoops.
We start talking and dancing and drinking, and before I realized it, the group I had gone out with came up to tell me they were getting the next pledge ride home. Decision time: do I go with my friends, do I invite this boy to come back with me, or do I stay and party? Before I even had a chance to tell them that only pussies go home when there is still alcohol flowing, my new friend said he’d hop in a ride back with us because he lived on campus too. Problem solved. So seven girls and one guy all piled into a small four-door sedan, meaning Mr. Potential Fuck Buddy and I had plenty of time to get cozy. With that many drunk girls in the car, of course we had to stop for food. My oh-so-generous suitor paid for mozzarella sticks. And they say chivalry is dead.
After we were properly fed, we were all dropped off to our respective dorms. I was last, and I did something I don’t normally do: I invited this boy upstairs. Now, don’t get the wrong idea. I fuck a good bit, probably more than your average single girl, but never in my room. I have this really weird thing about not liking to have sex in bed. Like I literally have NEVER had sex in any of the beds I’ve ever called my own. I also like to leave right after sex because I like to sleep alone, so inviting a guy over is crazy unusual for me.
When we got into my apartment, I showed him to my room and went to the bathroom, only to realize I had my fucking period. I’m a lady, so of course I wasn’t going to have rando sex on my period. Another night of sympathy head. Ugh. My roommate was away for the weekend and as I mentioned, I don’t like hooking up in my bed, so because I’m a drunk bitch, I moved things over to her bed. I told him the period deal, but ensured him I’d still blow him, so of course, he stayed. We got started – suck, suck, suck, lick, lick, lick – and then he flipped me around, 69 style. I was confused, but fuck it, I didn’t care. If he wanted to be eye-to-eye with my tampon string, more power to him.
I got back to business when all of a sudden I felt a tongue. IN. MY. ASS. This mother fucker was tossing my salad while I slobbed on his knob. This is so beyond, I can’t even. There were fingers and a tongue in my ass and then I got even more confused because it felt, like, really fucking good. I could not process what was happening, when all of a sudden he sat up and lined his dick up with my ass like a car about to pull into a parking spot. The next thing I knew, we were having anal. I had no idea how it happened, but it felt really, really good, so we kept going.
We finished, he pulled out and came on my (roommate’s) sheets and I looked at him for the first time, a changed woman. He had the biggest grin on his face and said, “I think I can get hard again, wanna try it again?” Fuck it, I might as well commit to the anal lifestyle. I looked him dead in the eye and said “Fuck yes.”.
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