I had my first time at anime convention when I was 19.

At that age I'd started realizing I was into guys, but I was still in that "well surely I'm not really gay, I've just been looking at too much porn, I just need to land a gf and I'll turn straight and normal" denial phase. But then my oblivious twink ass went and cosplayed as Link at an anime convention so obviously I was a hopeless fag, I just didn't know it yet lol

Anyway, I was there by myself, feeling awkward and insecure. And then this slightly older guy (mid 20s, I'd guess) complimented my costume, and we get to chatting. He's super friendly and I hang out with him for a while. Then as the evening is winding down he invites me back to his hotel room. Allegedly to share some booze and pot... and of course I'm too naive to realize I'm getting picked up, I thought I just made a friend lol.

So I go back with him and we end up on the hotel room's shitty little loveseat watching some anime. A bit drunk and a bit high... enough so that when he "casually" puts his arm around my shoulders I lean into him instead of stiffening up.

So we get progressively more cuddly. As he starts touching me more I'm internally freaking out, but it feels really good and I'm kinda paralyzed by horniness and this is so fucking gay wtf am I letting him do this. Then he pulls me fully into his lap, and feeling the tent in his pants pressing into my ass finally shocks me into giving a pathetic little protest of "I'm not gay." And he just chuckles like I'm joking and says "yeah me neither" and then starts nuzzling my neck and reaching into my costume to pull out my hard dick. And I just kinda melt and give in.

We ended up fooling around for what felt like hours. I don't think he realized I was literally a virgin (instead of just being super shy) until he started trying to fuck me and I was too tight and nervous for him to get his dick in my ass.