Junior year of college, I volunteered for this frat’s charity date auction event because I knew some of the brothers (including [Sam](https://www.reddit.com/r/SluttyConfessions/comments/k1elmz/even_two_years_later_i_still_masturbate_thinking/), for those of you who read my stuff!). It was basically a fancy-ish college party: guys in ties, girls in pearls. The frat auctioned off dates with female volunteers for Alzheimer’s research. I wore a standard cute little cocktail dress and heels (and pearls, obvs).
The guy who “bought” me was cute, I kinda-sorta knew him, and he was a total gentleman on our date a few days later. Afterward, he asked if I wanted to hang out with a few of his friends back at their apartment. I already knew a bunch of those guys and said sure.
Now, the thing you have to know is that a bunch of those guys had been there when [I got my first facial](https://www.reddit.com/r/SluttyConfessions/comments/k1elmz/even_two_years_later_i_still_masturbate_thinking/) at the same frat the year before. Like, they had watched, and I sorta had a *reputation* for being… fun. ? But they were totally cool about it. So back at their apartment, they joked about how committed I was to curing Alzheimer’s and saving the world. About an hour or so later, I was a little buzzed and having fun being the only girl among six or seven guys.
Then, one of them asked if I’d ever done anal. I said I hadn’t. (Technically true, even though I’d stuck other things up there to try it. I knew that I liked it.) Then he asked if I would consider doing it, “for charity.” I jokingly said it would depend how much. And the guys all sorta looked at each other and immediately came up with like $400 between them. All for the frat Alzheimer’s charity, they said, if I would do it.
I had sorta been kidding, but then realized they weren’t, and… uh, well Marissa after a few drinks and in cute clothes gets kinda slutty, so I said okay.
I got to pick the guy – Brandon. Tall, black, great body. (I’d hooked up with him before.) Also a super nice guy who I knew would be gentle. I told him I needed to work up to it, so I had to two tequila shots first. Then, he took my hand and led me back to his room, where he got me naked and started eating me out. I get very turned on really quick, so it didn’t take me long before I came. And then I was ready, loose and more relaxed. I came out of Brandon’s bedroom naked, and laid down on my belly on a blanket they’d thrown on the floor. With the other six of them watching, Brandon – also naked – lubed me up and got on top of me.
For those of you who have never had your ass fucked, it’s a really intense experience. I had had several cocks inside me before, but never one in my asshole, and I was a little scared at first! But Brandon was wonderful. Slow and gentle. It wasn’t too long before he was balls deep inside me. It was really fucking hot, especially once he wrapped one arm around me and started massaging my clit while he fucked me. The other guys could just stare in disbelief. Pretty soon I was moaning and groaning and panting on the ground under him like a cheap whore.
(I probably would’ve sucked every single one of their cocks if they’d offered me one right then, but none of them had the guts I guess ?)
Brandon made me cum again with his fingers, and shortly after that he unloaded inside me. He was wearing a condom, so cleanup wasn’t too bad. And poof, I wasn’t an anal virgin anymore.
Since then, I’m totally down for anal. Doesn’t scare me anymore, and I actually really like it. ?
Source: reddit.com/r/gonewildstories/comments/k9ye7u/i_23f_auctioned_off_my_anal_virginity_for_a_good
Definition of a dream woman