r/Gaytguyhornyjail

Last night I (FtM 27) was able to penetrate my partner (AFAB Enby 25) with my t-dick from behind. My partner and I are both on testosterone and have been for some time now, with our bottom growth we have been able to penetrate one another in a missionary position, but I've wanted to try more. For a long time I was just really nervous about it not working and me feeling ashamed, but we've been together for a little over 2 years now and I've never been more confident sexually exploring with another partner like I am with them. I have been obsessed with their ass forever, they have a tattoo on one side too which just drives me insane. So I've had the fantasy of fucking them from behind, I just wanted to be able to use my t-dick because that feels so good. We had just had sex in the usual missionary position and we had gotten up, but then we were being funny and I said something that made them go "Oh whatever" and roll away on the bed so they were on their stomach, still naked. So I was being the way I normally am when they roll away from me and I climbed on top of them, also still naked. It was silly for a second until I settled my weight on them better and I felt my t-dick brush against their hole, and they moaned. I sat back, sort of standing on my knees but keeping my t-dick inside them and started thrusting. My t-dick is a little over 1 inch when I'm hard, and god it was amazing. Needless to say, we have a new favorite position, and it helped to have them lay on a pillow and keep their legs closed (the second part could have more to due with our height difference because I am like 4 inches shorter than them). It was awesome and I just wanted to share because it also feels like a really cool milestone.

With the guy I’ve been seeing for a little over 2 months now. We had been texting back and forth because we haven’t seen each other in 2 weeks so when I saw him yesterday it was game on. We couldn’t keep our hands off each other and we did PIV which was extremely nice considering he’s big down below.

Lots of foreplay and heavy making out, he surprised me with anal and honestly it hurt at first but the DAMN THIS FEELS GOOD way. Felt really good and I liked it. Can honestly say it felt very affirming.

Tuesday: wore my snug plug 2 for 12 hours, then pounded my hole with toys with NO lube. For the first time I was able to pound myself rough with no issues! My ass produced juice by itself and it felt amazing. If you want videos, msg on discord or snap.

Wednesday: took a break to make sure my hole was Ok.

Thursday: currently plugged for 21 hours since 1am, I was motivated by my anal trainer to plug my hole.

And been jerking off like crazy for the first time in years.

hey! I was discussing this with my dom the other day. he had been referring to me as "sub" but asked if there are other names that would be appealing. "sissy" and "pussy" give me a weird dysphoric ick. we also don't use "slave" due to racial implications. I enjoy being called "boy," but it doesn't really cover the humiliation angle. do y'all have any other ideas?

There's not much to this story, but I wanted to share it anyway. I went to the local gay sauna last night with a friend of mine, and my goal was just to get comfortable being naked around a bunch of strangers.

It felt way more natural than I had expected. I didn't feel uncomfortable even once. Not in the locker room, the shower, the sauna, or the hamam. My friend stuck to my side all night, so I didn't pair off with anyone. But it was really nice just to feel guys looking at me with interest and to be able to look back freely.

Next stop is the gloryhole upstairs, which I'm really excited about. My ultimate dream would be to get sucked, but even if I "just" get to suck some dick, I'll be a very happy man. I'm finding that I really like just existing in hyper-sexual gay spaces, as a very sexual person. It feels weirdly relaxing.

So in stealth and I’ve been talking to this cis guy recently (first time ever talking to/dating a cis man). When he first approached me he didn’t know I was trans and I only told him that I am very recently(sue me), anyways before he learned I was trans he told me in passing that he can never get it up for a girl. Today we finally had some action and when he got hard I felt so euphoric and validated that he sees me 100% as a man. Yall I’m so happy rn

I've been texting and calling w another T guy lately and not only do we really get along on an emotional and practical level, but they are also so goddamn sexy I don't know what to do with myself.

This morning, woke up and had the very specific horniness to be choked and fucked by him. He has these magnificent arms, and I've already often dreamed of their cuddle potential, but we are now veering sharply into horny territory. I just think it would feel amazing, him on top of me in that way... Did I also mention that he's tatted?

A, if ur seeing this (bc we have talked about this subreddit before), let's make it happen 😘🍯🥕

Okay so im a trans dude, im stealth passing.

Your standard Socially awkward outdoors nerd type.

So recently I've been talking my dog to a local park, thier is a guy thats at the park with his dog as well most of the time. We have talk a few times for a bit and he is really hot and seens like genuinely kind person, the dogs get along really well too.

( Ive been told by a mutual that he is cis het )

I miss before transitioning when I had guy friends to hangout with but lost touch with a lot of them over the last two decades.

Horny jail time is we where talking and I sorta got caught in my own head at one point and then he made a commit about boundaries, not sure if it was directly about me but I realized then the thought I was having wasn't really friendship levels of interest. It got a bit quite and awkward then went separat ways. I haven't seen him yet since. I don't know what to do when you ooops I had a thought of you in a sexy way lol to straight dudes? Is it real you just walk up to each other and be all sorry bro no homo? Like I like him as a person and would want to be his friend and idk just chill and bullshit but what if I made it weird and that's not even what the weird part??

HOW THE FUCK DO FRIEND HOT STRAIGHT DUDES?!

I just got home from having a t4t4t threesome at my local bathhouse and dear god, trans guys give the best head 🥵🤤🫠

So I installed grindr. Because I get horny. And this guy i used to hook up with texts me. He is VERY good at what he does. Primal play, cnc, anal, piss play. He is so damn good. He has a dick that hits the spots inside that just make my tongue roll out and my jaw go slack.

Unfortunately I had to turn him down. Im not up to that quite yet. When asked why, I showed him a photo. He STILL expressed interest. I needed that. I needed to feel desired.

Maybe he will text again when the doctor clears me.

I’m 27 and recently single, broke up with my fiancé after realizing we weren’t a good fit after two years together. While I’m not ready for a relationship and am just enjoying single life for now, I realized what I want when I do start looking for something serious again, at least as far as sex goes.

I’m a bottom through and through, I love being bred, having my pussy stretched, and just generally treated like a toy for someone else’s pleasure. I also love group play despite my limited experience.

I would love to have a partner who likes to slut me out, invite their friends over to have their way with me while they watch or join. All safely of course, regular tests and such. I really like the idea of being blindfolded the entire time so I never know which of their friends have used me, always wondering when we’re just hanging out if they’ve seen me naked. I just don’t know how that would even come up in a regular relationship that doesn’t start with sex, which is what I’m hoping my next relationship will be 😅

I can't help but want his attention all of the time. I missed my opportunity to get dicked down and now I have to wait until August.

Now, I want his attention. I want him to text or call me and have him tell me about all the things he wants to do to me. I want to know exactly how he'll manhandle me, how he'll face fuck me, and whatever else he can think of. I want to know.

Absolutely antagonizing.

Edit: I want to tell him that I love his attention and just talking to him. But I'll probably drive him away </3

One of my biggest fantasies is engaging in totally anonymous sex (or at least roleplaying anonymous sex) as a top/side. I find the idea of getting sucked at a gloryhole so fucking hot, or using a cumdump's hole/s - especially in a group of other tops. I have no idea how I'd go about doing this in a way that feels comfortable, especially since I wouldn't want to be the center of attention (as the only trans guy there, for example, or the only guy using a prosthetic to fuck). But it's one of my biggest fantasies, and I've been thinking about it a lot lately.

Shout out to the cumdumps at play parties. You're doing God's work. And damn, I really, really want a piece of you (respectfully).

First post here so I hope this is okay. I really just need to have a place to say this without sounding dick obsessed (I might be though). For context, I've been staying on campus for a couple months and have been away from my partner.

Idk if it's because of upping my T or the illusion of missing out on more sex than I likely would have (maybe both), but I'm horny ALL THE TIME. My classes are mostly online and I work from home so a lot of my time is spent rubbing myself dumb until I can't see straight or have completely ruined my sheets. My lips are sore from constantly touching myself while imagining getting pounded into my mattress 😓

Anyway, I finally move back home next week and I can't stop thinking about having my partner over literally all the time to fuck me. My pussy is practically begging for his dick. God I can't wait to get stuffed.

long time lurker first time poster blah blah blah let's just get into it shall we

so for background my (22m) partner (21nb) has been abroad all semester and we've missed each other terribly. well as of today they're back in the states after five long months apart and it's not much longer until they're back in the city (they're staying with family in another state until their summer job starts). well of course there's the anticipation of it all, we're getting excited to see each other again, and our texts have been getting quite a bit spicier. they're on the reserved side so it's always exciting when they get a bit more dominant-- that's exactly what's happening here. i can't get enough of it.

anyway they told me to send a video, and they told me they wanted to hear their name. well i was feeling bratty so i sent them a video without following those instructions. sure there was all the whining and whimpering and begging my partner could possibly want, but not their name. then i had the genius idea to egg them on even further when they pointed it out.

"guess you'll have to do something about that :)"

"don't worry, i will :)"

then they told me to just wait until we were together in person again and asked how much overstim i think i can take. i made another mistake and told them the truth-- A Lot. fellas, it's been nice lurking on this sub. i might be fucked.

(lmao acting as if this isn't exactly what i wanted. make no mistake this was the goal all along. perhaps i'll update you all when the punishment actually happens)

I’m currently seeing a cis guy for the first time and we’re both interested in having sex soon. I’ve never had any sexual interaction with a cis man not to mention PIV or anal. he asked if I preferred PIV or anal but I really don’t know. I’m worried anal will be too much work(really don’t know how that works) and I’m worried PIV could potentially make me dysphoric.

Any thoughts? Any experienced guys wanna share some wisdom?

But the streak has ended as of last night. All good things come to an end right? 😮‍💨

Idk how I didn't realize thats what the full body tingling was, I think cause sometimes it makes my hand get so stiff it'd freak me out. 😶 Last night though it was more mild but still made me feel really good. Drained this poor man's balls haha

previous posts about this same guy: https://www.reddit.com/r/Gaytguyhornyjail/s/vsKHa4q5GP

I got to see him again a 3rd time last night and I am absolutely obsessed with how he fucks me. Each time I see him I cannot get him out of my head for weeks after. He pounds me so hard, so deep, and so much. Crazy stamina. With other guys I'm always trying to get them to go multiple rounds because I'm still horny when they've cum, but with this guy I feel like we're actually matched up in terms of stamina. I haven't timed it but each time I've been with him, the actual fucking part feels like it's gone on for like an hour. It feels like he's trying to use me in every position he can think of. This time there was a new one for me, he fucked me doggy style with my torso on the bed and my legs off it.

This was the first time I gave him a blowjob too, and he said it was some of the best head he's ever gotten, he was really surprised how long I was able to keep sucking him. I didn't make him cum when I first sucked his cock, I got him close but he wanted to fuck me. But since I was spending the night, I had another opportunity. We were cuddling in the morning and I reached around to feel his bulge, and pretty quickly I was in my preferred dick-sucking position: laying on my torso between his legs. I did the same things I had done while sucking his cock the night before, listened to how he told me to use my hand, and of course made him cum this time. When he asked me if I wanted him to cum in my mouth or on his chest I just kept sucking and let that make it clear what my answer was. Then after he came he asked if I wanted a towel to spit it out on and I had already swallowed. He was Very impressed by me, said it's really difficult for him to cum from head, but that I did everything perfectly :).

Hi!! Someone I’m involved with recently got stage 1 (WOOHOO) & I’m so happy for them. We are both excited for them to be cleared for sex of any kind. I have PLANS with them I tell you PLANS. I’ll write about those in another post sometime. 😈💜

I’d love any advice for how to help them feel maximum pleasure and sensation based on any of your lived experiences. I know every body is different, and I feel confident in our communication together and our ability to navigate that, but I feel like my basic conceptions of how sensation & sensitivity work with phallo are a blank slate. I’d love to know either what feels good on your body or on a partners body so I can have some ideas of touch to try together. I’d like to have some anecdotal understandings going in. Thank you so much!!! <3