Author: TegaMalmo

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. Read more »

I [M] went from getting orally serviced by one of our team’s water girls, to discovering she’s trans [TF], pounding her in the shower and then upwards from there ?

I play competitive soccer full-time for most of the year. It’s a very good gig, all told. There’s a small group of all-purpose team helpers who do stuff like getting water, collecting towels, running “go-for” errands and stuff. All of them are college-age. Two years ago, a new girl started – Leslie. (Not her real name, obviously.) Real pretty, 23 years old (I’m a little over ten years older), short, curly blonde hair, green eyes, and an amazing rack. I noticed her right away.

Everyone on the team is really friendly with the “gofers,” since they’re around all the time. Even the girls are often in the locker room while the guys are in various stages of undress. It’s just how things work. In part for that reason, there are supposed to be strict rules about no fraternizing with them or other team staff. But… that rule goes ignored pretty frequently, which is pretty common with sports teams.

Leslie noticed me, too. She would cheer me on the field, give me eyes off of it. I realized, later on, that she mentioned her hotel room to me a couple of times on away games, and that I should’ve realized what she was hinting at. Read more »

I [M] met my now-wife [TF] when she was my student. She’s a trans girl. Now we live in the suburbs and basically no one knows.

“Sarah” and I met when she was my student and I was her professor for freshman composition in community college. She was already living as a young woman then, and could easily pass – she has a very naturally feminine frame and body type, she’s really into her makeup and hair, all of that stuff. She was flirty with me from the start, but hey – I’m not gonna hit on a student. Big no-no. Nevertheless, she would come to my office hours, ask about my personal life, bat her eyes, that kind of thing. After the semester ended (and, ahem, grades were in), I let her meet me at a bar nearby. She couldn’t legally drink yet, but we started dating soon thereafter. I was about 20 years older, but she didn’t much care.

We made out pretty hot and heavy on our second date. I definitely expected to sleep with her on our third – she was coming over to my place – and that was when she let me know that she had a dick. That was… uh, sort of a surprise, obviously, but I went with it. And holy shit, am I glad I did. She absolutely loved to suck my cock. Her “pussy” felt fucking incredible. The next morning, she was up early making breakfast for me, and woke me up with a long, sloppy blowjob. Wow. (And yeah, I dropped her off at school after that.) Read more »

I dated this girl, discovered she was trans, went along anyway, she blew my mind, and I paid for her breast surgery. Zero regrets, would recommend. The best girls are sometimes boys. [TM]

I am a 39 year old professional. I’m unmarried (by choice) and have no kids. I’ve been very successful in my career. I don’t say that to brag, only to point out that money isn’t a big concern for me.

About two years ago, I’m out with some friends at a bar when I see this smoking hot girl. I went and chatted her up. “Jenny” (not her real name) was younger (24) and clearly attracted to me. We wound up making out for a while in an Uber, during which she was also stroking my cock through my pants. We made plans to hang out a few nights later, which ended with her giving me a brain-melting blowjob. Honestly, best I’d ever had.

The next time we hung out, I was fully expecting to fuck her. And, sure enough, we were going down that path at my place, when she stopped and, looking sorta embarrassed, gave me the “I’m not like most other girls…” talk. And dropped the bomb that this girl… had a dick. Read more »

That time I made my roo[MM]ate my girlfriend for a few weeks in college

About 15 years ago, I was a college senior. I was an ice hockey defenseman and Army ROTC cadet, and probably what you imagine: big, strong, sort of a jock. Not dumb (at least, I don’t think!), but definitely not that interested in classes. That fall, there was this crazy flooding at our school and our ROTC dorm was evacuated. We were mostly scattered across campus, wherever they had room. I got bunked in this room with a sophomore named Joey.

Joey was this prissy little boy from some Boston family with money. He was gay, though he would always describe it in some kind of gender studies language I could give a shit about. He was probably 130 pounds and extremely feminine. Gay guys today would call him a twink. He was flirty, had long dirty blonde hair, liked to wear makeup and sometimes drag. When he did himself up, he could *just* almost pass as a cute, flat-chested girl. That sorta made me think… huh. Read more »