My first trans girl hookup was voted our frat’s House Sweetheart, and also taught me statistics [MF] [TF]

I’m a pretty typical “bro” type IRL. I play soccer and rugby, I’m a gym rat, organize my group of friends’ fantasy football league, that sort of stuff. Getting dates has never been a problem. I’m about 6’2, 200 lbs, thick dark brown hair and blue eyes.

A couple years ago in college, I was on the board in my frat. It was my job to get a tutor to come in to help some of the brothers (like me) out, because our grades were shit, mostly because we were too busy getting plastered or working out to study. Eventually, we found this guy named Andy to come in. Andy was a junior, and basically the opposite of everything in our frat. He was small, even petite, and very effeminate. He was gay and out. He was also really smart. So, basically the opposite of everything in our frat.

Andy was a good tutor, and the frat basically paid him to help out like 5 or 6 guys with homework. He’d come in 2 or 3 times a week and spend all afternoon there, an hour with each guy down in our commons area. I couldn’t really study well down there so he met me up in my room.

Longish story short, a few months in, Andy comes into my room while I’ve got headphones on and I’m jerking off to some porn. I didn’t see/hear him immediately, and when I did, I was startled and was like, “shut the fucking door!” I guess Andy sorta got the impression that this whole setup was kind of a hint, because hesitated for a sec, then shut the door behind him, came over, and asked “you want me to take care of that for you?”

I definitely had *not* had some big plan in mind! But, uh, Andy was getting on his knees between my legs, and I was really fucking horny, so… I just let him suck my cock. First gay thing ever for me. He’s using one hand on my shaft, the other massaging my balls, moaning and bobbing over me. It’s the best blowjob I’ve ever had. I barely lasted a minute, and blew my load in his mouth for him to swallow.

And then, he helped teach me stats.

After that, Andy started sucking my cock before every lesson, usually 3x/week. After a week or so of that, one evening, I’m particularly turned on, and I toss him on the bed (he was really light) and told him I was finally gonna fuck him. He asked what had taken me so long. I lubed up his hairless asshole and fucked him good and hard on my bed on his belly. I reached around and milked his cock until he came too while I was inside him.

Then, he taught me stats.

Fucking a guy was obviously very new to me, but I didn’t really get weirded out or anything. I definitely didn’t (and don’t) consider myself “gay.” I’m not into guys. But I liked fucking Andy. He was a cool dude, and as we started to build sexual energy between us, it really fucking turned me on. I didn’t really think about the sexuality stuff too much and still mostly liked fucking girls.

That was junior year – me fucking Andy or occasionally letting him suck my cock instead. (He didn’t want me to suck him, for reasons I later figured out.)

SENIOR YEAR, we all get back from break and I text Andy to come by the house. I was Academic Chair that year and had to figure out tutor schedules again. (I also wanted a blowjob.) He said he’d be by, but that he had a surprise.

About an hour later, this cute redhead walks into the house. Long, curly red hair. Cute tennis skirt type outfit with a really low-cut white top that showed off these magnificent tits. Looked like she was dressed more for a frat party than tutoring. She sorta stands there, leaning against a column, letting me basically oggle them before I realize… IT’S ANDY.

That summer, Andy – now **Andrea** – had transitioned. Got *her*self a very, very nice boob job. She had always felt more like a woman, as she’d told me before, and had decided to make the switch. Surgery (top only), hormones, etc. And goddamn, between her body, the boob job, the makeup, the new hairdo, and honestly her confidence… she fucking passed, all right.

The brothers were all like… WOAH. Minds were blown.

*Andrea* was still much smarter than basically all of us bozos so we gave her all the tutoring she could handle. She was over at the house all the time. The first time I fucked *her* was incredible. Seeing those tits bounce while I nailed her was so fucking hot. Her voice had gone up, too, which helped.

Andrea was also pretty domestic. She made cookies for the guys. Made us do our homework. Gave advice, cheered us at interfraternity sports, that kinda stuff. Everyone loved her. So we voted her House Sweetheart that year – her picture’s up on the wall from our year. Later I found out that she was blowing like two or three other guys at the frat in senior year too, but… meh, whatever. She and one of the other guys started dating after graduation.

I honestly would never have really thought about trans stuff if not for Andrea. I’m a big supporter of trans rights now. I’m actually dating a trans girl now who is even hotter than Andrea was (and she was pretty hot). Totally changed my perspective. Love you girls!

Source: reddit.com/r/gonewildstories/comments/j1x4sk/my_first_trans_girl_hookup_was_voted_our_frats