Okay, so this happened a few years ago when I was in college. I was in my early 20s and, at the time, in a relationship. I had a pretty active social life, and a lot of my friends were separate from my girlfriend.

There was this girl in my class, let's call her Leslie. We were cool, just friends. We'd chat after class, hang out with our group, grab drinks sometimes. She was also in a relationship, and I always got the vibe that her boyfriend was a little insecure when I was around. Nothing ever happened, but you could just feel the tension.

One day, we were talking about relationships (we were pretty open with each other and our friend group) and she asked about my sex life. I told her it was awesome, and I mentioned how much I was enjoying anal sex. Her eyes widened, and she confessed that she'd always wanted to try it, but her boyfriend was super vanilla. Like, really vanilla. She said he wouldn't even lick her ass, and he wouldn't let her lick his balls or ass either.

Fast forward about a year. I'm single now, and I get a message from Leslie on Facebook. We catch up, talk about what we've been up to, and she mentions how she's single and just moved into a new place. She casually invites me over for drinks.

I figured she was probably down to hook up. So, a few days later, I head over to her new apartment. We have a beer, catch up some more, and then I just go for it and kiss her. She kisses me back, and things quickly escalate.

After some heavy kissing, I start moving down, kissing her chest, then her legs. I start eating her out, and she's moaning like crazy. Then, slowly, I start moving my tongue down towards her ass. I pause and ask her, "Are you sure you want to do this?" She just says, "Keep going."

So I do. I start rimming her, and she's loving it. I can tell she's really into it. I start fingering her while I'm rimming her, and she's practically begging me to stop teasing her. That's when she says, "I want to try anal."

Now, I'd had some experience with anal sex from a couple of previous partners, so I wasn't a complete newbie. I knew what I was doing. It was really fun to rim her and then lead her into anal sex. I made sure to lube her up really well, and I kept fingering her to keep her relaxed. A few moments in, I suggested she use her vibrator to help her relax even more. She did, and it worked like a charm. She came pretty quickly, and it seemed to make the whole experience even better for her.

Well, that's the story of how I took my college friend's anal virginity. It was a fun night, and definitely a memorable experience for both of us.