Soooo, I’m a 23-year-old trans girl, completely passable, often told I’m cute, am often hit on by guys who are surprised when I tell them what’s up. If you want to know more about me including some pics I’ve posted, check out my post history! I’ve only been sexually active with guys for about a year now, but it’s been a hell of a year. (A story about my first time is also in my post history).
Recently, I moved in with a couple of straight male roommates. One of my roomies I’ve known for years and consider a good friend (we’ll call him Adam), the other is a friend of his who I didn’t know all that well until more recently (we’ll call him Jeromy).
To preface this, I knew for sure Adam wasn’t into me sexually and after hanging out with Jeromy a few times, I didn’t get that vibe from him either (or I never would have moved in, I don’t need that kind of drama in my life.) So when they offered me a chance to move into a new vacancy at their really nice house for really cheap, I jumped on it!
At the time I moved in I was in my first steady relationship with a guy, Jeromy had a girlfriend he’d been with for a really long time, and Adam was playing the court. A couple of months into the new arrangement, when hanging and Netflixing with just Jeromy one night, he said something kind of hurtful. Something to the effect that he didn’t think my boyfriend would ever be able to get a girl as hot as me if I weren’t trans, and that he’d got himself a “good deal.” I’d tried to brush that off, but never really forgot about it.
In the next few months after that, both Jeromy and I broke up with our significant others. When I’d had my breakup, both Adam and Jeromy had taken me out for drinks to help me feel better (though I really didn’t super need it). When Jeromy went through his breakup, we all went out together to do the same for him. (Obviously it was a lot harder on Jeromy since he’d been with her a lot longer, and because *she* was the one who left *him*.) And that’s where our first problem happened.
While we were out, Adam ran into another group of people and wound up leaving us to hang out with them. Jeromy and I agreed to Uber home together. When we got back, we were both super-duper drunk and just kind of sat up playing random funny YouTube videos on the big TV in the living room. While we were doing that, we started talking about our relationships again (we had been all night) and I got on the subject of the thing he’d said that I’d found hurtful.
When I brought it up, he apologized right away and said he’d felt bad the second he’d said it and had hoped I’d just forgotten about it. He said that the truth was that he was a little jealous of my boyfriend for having the courage to be in a relationship that was socially stigmatized and for being able to date a girl as pretty as me.
“Are you saying you’re attracted to me?” I asked.
“You’re ridiculously sexy and there were times I got so jealous, for real.”
“I mean, do you think it would work between you and a trans girl anyway? I mean, sexually?”
“I loved doing anal with Jen, it’s probably what I’ll miss the most,” he answered.
We both laughed.
We talked more and it turns out he was serious about not having the courage. He said he felt like he’d never be able to deal with his family and even some of his friends if he had something serious with a trans girl, and that it made him disappointed in himself and angry at how judgmental people can be.
“Don’t you ever just hook up with dudes?” he asked.
“You know I do!”
We laughed. The unspoken truth between us was that after I’d broken up with my boyfriend, he’d seen me bring home this guy a few times, and when he and Adam had asked, I’d basically told them it was a bang buddies kind of situation and that I didn’t think it was going to last.
It didn’t.
We were on the couch and I leaned into him. That turned into us sort of playfully shoving each other. Which turned into cuddling. And then kissing. And then me playing with his cock and him grabbing my ass and grinding on me. And then into me going to shower and clean up so that we could have a little bit more fun.
We had sex (at least) three times (I clearly *remember*) over the course of the night he spent in my room. We’d do it, pass out, wake up, do it again, pass out, wake up, do it again. He did me on my tummy the first time and then I think the second time was when I rode him cowgirl. Then it was missionary which led to doggie. He wore a condom each time and when I came to in the early morning, I was alone in my room.
Adam had returned at some time late in the night or early in the morning and when I talked to Jeromy, he was worried that Adam might have heard us. This was a little hurtful, but I wasn’t too surprised. He said he’d prefer it if it was just a one-time thing and if nobody ever had to find out. I agreed that it would just make things complicated and awkward and that we should both just do our best to get back to how things were.
Flash forward, and I started seeing another guy pretty regularly. One night when I’m alone with Adam, he tells me that he’s one-hundred-percent sure that Jeromy is crazily jealous of this new guy and is hoping that I’ll break up with him. I laughed and played dumb.
That’s when Adam tells me that he is also pretty sure Jeromy spent the night in my room *that one night*. He hadn’t heard us, but he’d knocked on Jeromy’s bedroom door and peeked in on an empty room when he got home because he’d wanted to puff Jeromy’s THC vape. At first, he’d figured Jeromy was gone, but then saw that his car hadn’t gone anywhere and that neither had mine.
I confessed and we talked about it for a while. Long story short, Adam came clean about something he’d been keeping a secret himself. He said that as time had gone on and he’d watched me transition and become more and more feminine, he’d felt really confused about finding me to be more and more attractive. He’d always buried his feelings about me because he didn’t want to ruin our friendship, but he said he had felt really weird as he’d tried to deal with the possibility that I had slept with Jeromy.
“At first, I just thought I was having a hard time wrapping my head around it because it was so random and unexpected. I never sensed any kind of chemistry like that between you two and I kept telling myself there had to be some other explanation. Like maybe he just passed out in your room because you guys were drinking together or whatever. But lately, I realized there’s more. It wasn’t landing right with me because I know I feel things for you and instead of just being honest I’m standing by and you’re having a random fling with my buddy who didn’t even seem to like you all that much.”
I told him it was just kind of a crazy thing that happened because we were drunk and that it wasn’t ever going to happen again. I admitted to him that I had started to find him really attractive after I had my little thing with my first-guy-ever and realized that I was into dudes, but I hadn’t sensed that he was attracted to me at all so I’d just kind of pushed it out of my head.
“I really like hanging out with you and living with you has made me realize we have a lot in common,” I told him.
“Same.”
There was a pause.
“So are you serious about this guy you’re seeing right now?” he asked.
“What, do both of you want me to break up with him?”
We laughed.
“Kind of,” he said.
I told him that I wasn’t sure where it was going with this guy, but that it seemed to be more than just sex. He told me he was really happy for me. We hugged and when it got late, went to our own rooms.
Flash forward a few weeks from there. I’d made it official with the guy I was seeing and then almost immediately found out from a friend that he was running around with this other girl. I confirmed it with someone else who told me that he was basically a man-whore and that I shouldn’t expect anything serious with him or let him break my heart.
The night I found out, I got really drunk with both Jeromy and Adam at our house and they were both trying to make me feel better about it. When I went to my room, Jeromy started texting me almost immediately saying that he was thinking a lot about *that night*. He said he wished Adam wasn’t there because he really wanted to come into my room and play with me. We chatted a bit and I eventually told him that Adam had already figured it out, more or less, and then had tricked me into confirming it.
About a week after that, Adam is home for Thanksgiving (this last one) and I’m alone with Jeromy and he isn’t shy about trying to advance on me. I told him it was a bad idea and would make things too weird around the house.
“Anyway, you can’t even deal with Adam knowing, so how is it supposed to work?”
“He already knows, so I guess I’ll just have to get over it.”
“Yet when you *find out* that he knows you stop even looking in my direction until we’re finally alone and then you’re all over me like you haven’t seen a girl in a thousand years.”
He told me he was still adjusting to it but that he was sure things would work out. He said it didn’t have to be anything serious at all, we could just hook up on the down-low when either of us needed something like that and he was sure we could both handle it and not get attached or let things get weird. He said he’d rather the two of us do that than see me hook up with random losers who are just using me.
“Well, things might be getting weird already, because Adam and I started talking and I think we really like each other.”
He was shocked and he seemed to be pretty upset about this revelation. He told me that even though he didn’t want anything serious with me, it would be really hard for him to deal with watching me and Adam get all coupley if we started a full-on relationship. He said it might be so rough, in fact, that he’d have to think about moving out.
I told him that he was being a self-centered jerk.
“So because I’m a girl who you would like to fuck when you get drunk and have a boner, it’s going to just rip you to shreds if something real starts to happen between me and your friend.”
“I’d be happy for you but I’d constantly be seeing you guys together and I’d be hating myself for not dealing with my hangups and for letting you go be with somebody else.”
“Sounds like it wouldn’t be much easier even if it wasn’t Adam.”
“At least then he wouldn’t be around constantly and he wouldn’t be my friend, so I wouldn’t have to talk to him about you or be, like, jealous of a really good friend. You know?”
I told him that even though I’d been born as a male, I was sure I’d never understand how stupid boys act sometimes. He agreed with me that he was just being crazy and irrational about it. He said that’s what bugged him the most–he knew what he was trying to do about the whole thing didn’t make any sense but that he couldn’t make himself act right and that it made him hate himself.
Alone for the holiday together, we shared dinner and a lot of drinks at a nice place that was open on Thanksgiving night. I’d legitimately tried to make plans with someone else, but that hadn’t materialized. He had said nobody else he knew was in town when he asked if I wanted to hang out that night. I didn’t believe him, but I didn’t care too much either way.
Long story short, we got toasty while we were out and then I got really high off his vape pen when we got back. We had crazy sex all over the house–all night and several times the next day. The sex was actually really, really good. He made me cum like crazy, sometimes more than once per session, and I made him shoot a pile of condoms full of his jizz.
When Adam got back, we talked about it. He wasn’t a fan of the new developments but said he wouldn’t begrudge me a hook-up partner. I told Adam that just as the first time, I considered it a mistake and that Jeromy and I had again agreed that it would be too weird to have something like that going on in our current situation. (I’d found it funny but not too damn surprising that Jeromy seemed a lot less intense about things after he’d got his sexual cravings satisfied.)
Flash forward to just a few weeks ago (early January). Things had actually seemed to go back to normal for a good while and I thought that we were all sort of moving past it. Neither of them were talking to me about it for a long time and I assume they weren’t talking to each other about it either. Adam had kind of a month-long fling with a girl he met that seemed like it might get serious but then fell apart. I’m pretty sure Jeromy had a dry spell and just watched lots of porn, lol.
Adam and I were alone and drinking (can you tell I drink with my roomies a lot?) and we got to talking about the girl he’d had his thing with. He was pretty bummed about it because he’d hoped that it was turning into something real, but she’d decided that it wasn’t working for her. I told him that bitch was dumb because he was just about perfect as far as I could tell.
We started talking about us again and things moved right along. I had sex with Adam that night, and it was Lexi-is-seein-stars amazing. The next day he told me that it was amazing for him, too. We spent a while talking about it and at first he was saying he wasn’t sure he wanted us to get serious because he felt sorry for Jeromy. When I told him that was stupid and not to let Jeromy’s weird problems ruin something for us, he finally admitted that he had his own reservations about having a steady thing with a trans girl. I wanted to kill him.
We were having little arguments about it for days and I was really pissed at him for not just being honest about his reservations from the start. I told him that he was like basically all the guys I meet: They want to hook up but they don’t want to introduce me to anyone they know if I’m out as trans.
In the middle of this, we were all three of us just hanging around the house one night, drinking (lol) and Jeromy knocked on my door after I went to my room for the night. Adam had told him about what had happened and what was going on between the two of us. He pretended to be sympathetic, but really just wanted to fuck. I did it with him loudly, wanting Adam to hear.
This got Adam *super* jealous. We fought more and one night, had a bunch of crazy sex in my room while Jeromy was home. The sex was even more mind-blowing for me than the first time.
The very next night, Jeromy wants it, and I let him have me.
I’ve done it with both of them numerous times in the past couple of weeks and it’s kind of turning into a thing where I’m living with two fuck buddies. It’s not as awkward as it might seem like it should be, we all get along pretty well and aren’t letting things get weird on a day-to-day basis. It’s gone from me doing an occasional all-night thing with either of them and become instead quick bump sessions where we get each other off and then go back to pretending that we’re all just roommates.
Last Saturday night, we all went to a house party together. A guy there wanted to hook up and made it clear he wasn’t looking for anything serious, maybe just one night. I told him that I already had so much non-serious stuff going on that there wasn’t room for any more, lol. (In that way, this new situation might help me to avoid sketchy stuff like that.)
When I said I was heading home, the two of them were soon behind me. Jeromy got home first and we were fucking in my room when Adam got home. When Jeromy left my room maybe ten minutes later, I heard him laughing with Adam downstairs. I was almost asleep when Adam knocked on my door and made me scream into my pillow like a madwoman.
Sunday when I was in the kitchen making my lunch, Adam slapped me on the rear and asked me if I wanted to play later. Jeromy was in the living room and was in easy earshot, which was surprising because we’d all been sort of playing it, when we were all together, (and not in my bedroom) like we were nothing more than roomies. Jeromy tried to initiate with me later that night but I turned him down. He was bummed and got kind of pushy and jerky with me and said it was no fair. I reminded him that none of us were getting serious and that if he was starting to get any kind of weird, possessive feelings, we should probably all quit what we were doing.
He quickly said that he was only joking.
On Monday night I was sitting on the couch next to Adam, wearing a loose pair of girly boxer shorts while he played a videogame. Jeromy came in, sat next to me, and started rubbing my inner thigh.
“Hey, I really need to cum,” he said, plain as day.
Adam and I looked at him. I think we were both shocked. After a tense moment, we all laughed.
“Seriously, though,” Jeromy said, “could we go do something in a minute? I’m too damn horny to get anything done that I need to get done tonight.”
“I mean, I’m sorry about that,” I said. “Go watch a porn. I’m not a sex doll for ya’ll to grind on when you get bored or lonely or get a random boner or whatever. You’ll have to wait until I’m actually in the mood too.”
“But then you’ll just do it with Adam,” he said.
Adam laughed and I shook my head.
“You guys can figure out how not to step on each other’s toes, it’s not going to be my problem. Both of you are huge jerks who don’t want anything serious with me and I’m a pathetic girl who can’t seem to turn down a hard cock when she gets drunk. It’s not like I’m trying to be with Adam instead of you or something. I’m not into *either* of you for more than a place to live, a couple of dudes to drink and shoot the shit with, and an occasional orgasm that I’m going to regret later. As soon as something real comes along, this is going to stop completely.”
That sucked all the air out of the room. Suddenly, Adam was too into his game to have noticed what I just said. Jeromy said he should probably figure out what to get for dinner.
That night I fucked Jeromy and less than an hour later, Adam. With both of them, it was really intense and both of them made me cum super-duper hard. Weirdly, it was kind of like makeup sex between friends or something.
That’s pretty much where I am today and I’m trying to figure out where this thing is going. Neither of them has told anybody we know what’s going on in our house as far as I know. (And why the hell would they? If either of them could be open about their attraction to a trans girl, we probably wouldn’t be in this weird mess.) Ever the huge hypocrite, I haven’t told any of my friends either, because hell no, I’m not going to have people knowing that I’m getting used as a piece of tail by *both* of my male roommates on the damn regular like I’m a goddamn after-dinner snack one night and a safety fuck the next when one of them goes boozing and strikes out with the *real* girls they’re trying to pick up *for real*.
I know I should stop this thing, but I can’t seem to do it. I’m having to admit to myself that being treated like a cheap secret hookup by the two of them is actually turning me on like silly.
That’s all for now…
Source: reddit.com/r/gonewildstories/comments/evyj13/the_roommate_situation_one_trans_girl_living_with
Jeromy’s bitch-ass attitude killed this for me about halfway thru. I couldn’t read it all :( still gotta get off tonight :)
I just hope you got yours off when you needed.
Fascinating. I guess I can see how it developed and how it would be hard to bring to an end. You’re all getting something out of it, but secret lives suck. I had that with my exwife and I won’t go back. I don’t hold back things from friends now. If they can’t handle all of me, they don’t belong in my life. That’s not advice, it’s simply where I’m at after several years of inner work.
Jeromy seems a huge asshole. Adam seems conflicted. If I were you, I’d probably move out. That sounds like a stressful life you’re living
So basically 3 gay dudes. Lol
Really hot except for the parts where you have 2 insecure assholes not willing to commit to you.
Really good story but why do you allow them to use you like that