r/Gaytguyhornyjail

I've been thinking a lot about my best friend in college. We'll call him Sam. We were inseparable for three whole years, from my sophomore to my senior year, and those years also coincided with the first three years of my medical transition. By year two, I was in love with him. Then I resigned myself to just being friends, but my feelings never completely went away. The thing is, I can't think about my transition without thinking about him.

When we met, I had just received the letter from my therapist green-lighting me to start testosterone. He was one of three other roommates in my dorm suite of two rooms separated by a communal kitchen and living area. It was co-ed, and there were three of us gay guys and one queer woman. Living like that is what made me think queers just don't do the dishes, but I digress. He was very tall (almost 6"5), very hairy (Greek), with a square jaw and cheekbones that could do some serious damage. He had thick, curly black hair, full lips, and big, dark eyes framed by the longest lashes. And he was also an anxious dweeb who cracked sarcastic jokes a mile a minute and always curled himself up on the couch to make himself as small as possible.

Our first meeting was inauspicious. He misgendered me accidentally, and when I pointed it out, he was so mortified, he shrunk in on himself a little. Even though I was a bitter, defensive little shit back then, I overlooked it and kept choosing to spend all my time with him. Guys, we did *everything* together. We ate every meal together. We watched hours upon hours of bad 80s TV together late at night in our shared room. We went to the one queer club in town together, even though I had to drag him there kicking and screaming. We were catty and snarky together in the student lounge late at night when everyone else had gone to sleep.

I started T. I got more and more masculine. I built myself up, putting on muscle. Our dynamic didn't change, but there were little things, like... When I bullied him into squeezing my shoulder muscle and he turned all red and curled up on the couch, stuttering a little. When we hit the sex shop together, and I coached him into being brave enough to buy the enormous dildo he wanted so he could ream himself whenever I wasn't in the room. Fuck, I wanted to be that toy so badly.

And then there were all the times I comforted him through his panic attacks. His manic depressive episodes. Times when he confessed how he hated being big and tall and hairy. How all he wanted was to be small and soft and taken care of. How he wanted to be the kind of boy he often dated, the boys who liked him for all the traits he disliked about himself, the boys he topped when all he really wanted was to bottom. In a way, it mirrored my own struggle. I was muscular but short and early in my transition. All I wanted was to be a dominant top, when the boys I attracted wanted to feminize me. We were mirror images of each other.

We kept in touch up until a few years ago. The chemistry is still there, even though we've obviously grown apart. We live on different continents, and I don't think he would actually be comfortable dating a trans man. I'm okay with all that. But I like to reminisce about him from time to time, and I wanted to share. Who among us hasn't been in love with a best friend, right?

tw // use of "pussy"

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we met off of grindr, at first it seems like it isnt going to work out, but thankfully it pulls through.

he takes me through a side entrance of the big ass frat house he stays at. we get to his room and have a small conversation beforehand.

fast forward, he has me on my knees, ass up, face down, as soon as i tell him im not keen on being the decision maker during sex as i like to be told what to do what out into positions my partner wants me in.

he starts spanking my ass and i can't help but moan. through my underwear he rubs his hard dick on my pussy.

he finally takes off my underwear, puts a condom on, and stretches me out. as always, it hurts in the best way possible.

i can hear him moan and grunt behind me as he thrusts back and forth into my pussy. i can't help but scream and moan as loud as i can.

he tells me to quiet down some and slows down his thrusts. i listen and shut my mouth.

eventually, he starts thrusting into me harder than before, and i make sure to keep my mouth shut

he finally finishes and lets me lay down to take a break before he drops me off at my dorm.

suddenly craving making out and sucking off another trans guy. someone help

“What terminal are u in?”
You guys… it’s 8am. be so serious.
But also I’m in terminal c :) wya

So I’ve been on testosterone for a few years now, and I thought I had a high libido before— phew. I only really started getting off after going on t and having some growth, and have only used toys. So now I can’t cum without a toy, and I’ve certainly tried. (The only other thing that has worked has been a detachable shower head). I’ve read that you usually have to take a break for a few days to weeks to regain sensitivity, but going just a few days without getting off has proven super difficult for me. My ultimate goal is to be able to cum with a partner, preferably from their hands or mouth instead of a toy (not that there’s anything wrong with that too). The t horniness hasn’t really died down even though it’s been a few years, has anyone else roughed it out until they can use just their hands? I never thought I liked getting off until I got a toy, now I find my hands to feel okay I guess but no matter how long I try for I can’t seem to get anywhere near close. Ugh. I’m also a virgin so I can’t say I have much experience with others touching me, maybe that’ll feel better?
Also yeah I did make another account for the sole reason of posting here haha-
Any advice would be appreciated, I love all of the stories here, you make me want to be a sluttier guy <3

So I’ve been messaging this guy (D) on Grindr for about a week but timelines never quite lined up until tonight. He told me his friend (R) was over if I was ok with him joining too. I asked for pics of both and they were both so hot. The guy I was messaging was fit with an average length but thiccc cock and his friend (who was actually his partner) was a twink with a lengthy cock.

I got to their house and they were both super kind and I was immediately super comfortable. We head straight to their bedroom and all undress. R was laying in bed playing with himself so I got in next to him and we started making out while D went down on me. R got up and had me start sucking him while he watched D absolutely eating me up down there. It was so incredibly hot. Then they switched. R went down on me and D and I made out while I jerked D off. I was so turned on it was amazing. Then they both said they wanted to fuck me so they took turns fucking me balls deep while the other watched and I jerked them off. They both hit different spots and I was in heaven. We had to take a couple second break at one point and both confessed that they had both gotten super close to coming but both wanted to make sure I was satisfied before they did. I told them to fill me up and they got right to it. First D. He put my legs behind my head and stretched me out so good, balls deep while making out. R was playing with my ass while watching D bust in me. Once D pulled out, R got straight to work. He was so deep, my legs were shaking above me and at one point I bit my own knee out of pleasure. He busted so deep and kept fucking it in till he went soft was out of breath.
Then all three of us laid in their bed and chatted for a bit. They said it was super hot and they had been looking for a guy like me for a while and that I was welcome any time. I invited them to come over to my place too so we exchanged numbers. I’m hoping to hear from them soon haha. It was honestly the best first threesome I could have asked for.

Edit- they invited me back today so we all fucked again and it was absolutely blissful. They said they are both obsessed with how great I am lol.

CW - Female anatomy terms (used to refer to myself)

TL;DR - Can't enjoy front hole penetration despite wanting to. Have tried everything I can think of to no avail. Advice appreciated.

Hope this is okay to ask here, wasn't sure where else to go for this. I (FTM, mid-20s) have been on HRT for ~4 years. I really want to enjoy vaginal penetration—I find it really hot and fantasize about it often—but I've never been able to find it physically pleasurable. If anything, it feels uncomfortable bordering on painful, like a burning sensation where I just want to remove the thing penetrating me as quickly as possible to get rid of the feeling.

I've tried using liberal amounts of lube, going slower, cumming beforehand to see if it would make me looser/more relaxed, and using smaller toys, but nothing seems to help. I'm at my wit's end and I don't know what else I can try. I only use toys nowadays, but I've tried it with a real dick before and it still had the exact same issue.

The only thing I haven't tried is using my fingers specifically to stretch myself. I have some mobility issues, so I can't reach the angle needed to finger myself for more than a few seconds. Instead, I've tried using a small toy (Pillow Talk Racy - the width is just under two of my fingers put together) to gradually open myself up. Penetrating with this toy feels better than my other one, but it still feels more uncomfortable than I feel like it should be.

Has anyone experienced anything similar or have any advice? I just want to get dicked down without having to prep for anal 💔

ETA - I've been having this problem since before I started HRT. People have mentioned atrophy, which I do suspect, but I felt like I should mention this as well.

I'm a bottom who enjoys Daddy dom stuff. If that's not your thing, scroll on.

I (32 he/him) have been married to my gamer spouse (they/he) for 13 years, yet somehow we had never tried a blowjob while they played video games. Until tonight.

I crawled over to my spouse's gaming chair and took a hit off their vape pen, while looking up at him. They asked me if I wanted to try sucking his dick while he played video games. I did, so we undressed and he sat down with his legs apart, their beautiful cock already starting to get hard. I kissed his thigh, then the tip of his dick, then I took all of their shaft in my mouth. They immediately started praising me and calling me a proper slut.

I sucked him hard for a good five minutes, deep throat and all. Playing with different techniques with my tongue. "Don't stop," they pleaded. I kept going, until I came up for a breath, and they told me to stand up. I stood up, and then he bent me over so I was folded in half and grabbing my legs. Then he thrust himself inside me. I said "oh, Daddy!" and he kept fucking me while we both moaned. As they were thrusting, they blasted my hole full of cum.

I stood up, turned around, and kissed him, my mouth still watering from the taste of his cock.

I felt so perfectly used, and I loved every minute of it.

There was a moment this weekend, goofing off in bed with my two boys, when the old “it gets better” PSAs from the Trevor project popped into my head, and all I could think was man… it got so fucking good.

We’re having a lazy morning anchored in the harbor of a gay beach town. After I managed to distract him from a video game with my throat, Daddy and I got our bratty princess boy facedown on the bed. He usually suppresses his tickle response well but I caught him by surprise, trailing little kisses down his asscrack. I felt him twitch and try to hide the giggle and it was game on, Daddy pinning his arms, me sitting on his legs. I rained tiny evil kisses over his ass and thighs while he writhed and giggled and begged very cutely for mercy until all three of us were laughing hard in a big naked tangle.

I looked up between his soft bouncy cheeks and caught the giant, goofy, madly-in-love grin on our daddy’s face right as he laid his head down gently across his husband’s back and told him, “boo, you are just the cutest boy on earth.” My heart melted and exploded and healed and grew ten sizes, all at once.

Happy pride, cheers to gay marriage, threesomes, and men.

Go fall in love with a sniffies hookup.

So I went to Pride with my rugby team this weekend.

Ended up making out with one of my teammates and his partner.

For.

Like.

Two.

Hours.

We finally called it a night because everyone had to be functional for the parade the next morning.

Fast forward to the next day and one of them texts, "Mornin' 😉"

I replied, "You left bite marks on my shoulders last night XD (not complaining btw...lol)."

His response:

"Good u didn't seem to mind."

Then Sunday night I informed him I was "low-key disappointed" he didn't get to put more effort into those bite marks.

He replied:

"Well fuck now he tells me."

"I'm just oblivious sometimes. Need to be verbally told harder."

Sir.

I had already invited you back to my hotel.

I thought I was being pretty clear.

Now we're flirting over Discord, I'm sending him excerpts from my very gay novels, he's sending them to his partner too, and I'm trying very hard to pretend I'm not thinking about both of them basically all the time.

Anyway. Rugby was supposed to help me get in shape. Nobody warned me it would also apparently introduce me to hot, bitey polyamorous people.

Also a little stoned. Needed to unwind after work so I smoked while gaming with my bf. Now I'm in bed and so hard I want him here!!!

Need to grind against his ass and get my hands all over him and have him spread his legs for me so I can get my hands on that fat little tdick. It's so fun to jerk him off before I scramble his brain completely. Sometimes I like to watch his face, kiss and make out with him, and bite him/mark him up while I finger him. Other times I'll push his head down towards my crotch, and he will position himself so I can still finger him while he puts his mouth to work. He's so good with his mouth it's unreal.

He probably won't be satisfied after my dick is spent. Leaves us with two options: I keep fingering him until I literally can't anymore, or he sits on my face. Both are lovely options that (usually) lead to him trembling on top of me. I love being trapped under his weight and between his thighs while I try to get his dick to hit the back of my throat. I also love when I bully his g-spot until he's dripping down my arm.. both are some of my favorite things ever I love my boyfriend so much.

My mental health has improved greatly ever since I accepted that I prefer to top and don't have to use my front hole for sex! And it's okay that I prefer anal when I Do bottom! My bf and metamour don't know it but they helped a lot in me discovering this and they are the most epic for it. Can't wait to see them both again next month <33

So for some context, I've started T last september and had top surgery in december, so while my chest looks masc, my face/body composition has lots to improve still.

Anyway, I work in a fetish club that's very open to all sorts of guests, and this saturday we hosted a Pride afterparty. Since I was working dresscode I met every guest coming in and there was this really cute trio of foreign gay guys that came in, we chatted a little bit and then they went on their way.

In my country sadly most of the cis-gay men are somewhat transphobic (as in they wouldn't find most if not all trans men attractive) so even tho I found these three cute, due to past experiences I let it go because I assumed it was useless to even try anything.

Well, later on when we were closing the club I was just packing up my stuff as one of them approached me and complimented my outfit and said I looked really cute. (Later he also joked when I was putting some stuff away that I look even cuter bent over lmao) We chatted for a little bit and (to my surprise) he invited me to go out with the three of them to another party.

I was honestly exhausted but it was such a euphoric moment my fomo took over and I went with them for an hour or so.

Then when I had to leave that party we exchanged socials, and just today they invited me to go out again so we will see how that goes

I’ve been transitioning for a decade, so euphoric moments dont come as often as they used to. But i’m still riding the high from an amazing moment of euphoria I experienced last night. I’ve been pretty active in the slutty gay bar scene for awhile. Last night I went to my favorite one with my partner and a boy we’re sharing as a fuck buddy. He’s a couple inches taller than me and maybe has 10/15 pounds on me. This has been my first fwb situation where I am strictly the top, so its been an interesting learning experience and a fun one too. Idk what was up with me last night but i was just absolutely feral for this cute little slut. We were making out all night and sort of without thinking i growled at him to wrap his legs around me. Without any effort i picked him up and slammed him against the wall. We made out like that for awhile with his legs wrapped around my waist. He whimpered that he wanted me to take him right there. If i had a cock it would have been inside him in that moment. We got a lot of attention from the guys there after I did that, with some of them even cheering us on lol. I do goto the gym a lot, but I’ve never used my strength to throw someone around like that, I’ve never been in a position to throw someone around like that. Especially someone bigger than me. I felt so strong and manly to see these other guys gawking at us, wishing I’d do the same to them. It made me extremely euphoric and definitely put me in dom headspace, maybe for the first time. He definitely enjoyed it too. Anyways. Gay victory//gender euphoric moment I wanted to share.

The horny has kicked in full gear and I hate it. If I orgasm I’ll hurt myself internally from the spasms. Dick is twitching hard and I feel that shit inside me it hurts but also feels good.

Over here crying in my mind about it a little.
Weird fucker that I am. Maybe I’ll cum in my sleep.

Edit: I came when I just meant to edge. 12 days post op btw. Some pain but not a lot.i controlled the muscle contractions as much as i could. Feel so much better though. I can sleep through the night. Early this time. Helped with some pain relief. Contradictory I know.

(TW I use specific language in this post)

When I was a child I learned in school how the sperm cells in cum that comes out of penises may get people with vaginas pregnant (and that sperm may be even in precum).
thanks to my black and white thinking I concluded out of this information: cum= bad and also tip of penis=bad.

I knew that I was into guys and my fear of pregnancy was kind of always in the back of my mind growing up.
When I realised as a young adult that I’m actually a gay trans guy this fear didn’t went away but got even worse.

Last year I found out that I’m neurodivergent. This made me question some of my thought patterns. sometimes I take things way too literally or accept things someone tells me as fixed rules that I have to live by.

I try to overcome my sexuality related fears. One part of that means for me to understand where this fear comes from.
I want to have enjoyable sex with people who have penises (without that nagging voice in my head that tells me: be careful! You could get pregnant! Don’t touch here! You could get “contaminated”)

Back to cum.
in my very first relationship (I was 15) my then boyfriend told me to swallow his ejaculation. That it would turn him on. I don’t know if that was actually the case. He made it sound like it was expected, like it was an adult thing to do.
I did it and hated it.
And I internalised that I have to please my sexual partners that way. Even if they don’t ask for it. Because it goes without saying.

More than a decade has past since then.
Today I had someone’s cum in my mouth and spit it out. It didn’t even taste as bad as I remember.
Maybe it just was just that one teenagers really disgusting cum… (he was a smoker and energy drink addict who believed a bit too much in 72h deodorant)

This is just me sorting some thoughts.
I get that cum is very erotic for some people. Or just neutral.
I’d love to hear your thoughts on it.

Per the title, I'm curious if anyone has any experiences they'd be willing to share at Steamworks Chicago. I am healing from top surgery and hoping to plan my first visit sometime in the fall/winter, but curious to hear how other people have felt there since I know the different locations have different local culture / vibes, and I haven't heard much about Chicago's.

I'm curious about any / all experiences you'd feel comfy sharing, but some specific things I'm wondering about are:

- There's a TM4M night, 3rd Monday of each month. Has anyone gone to one of these? How was it / did it differ from going on a regular night, if you've been to both? Is it treated as taboo / frowned upon to go as a trans man on regular nights?

- I'm interested in this vs. more casual / natural cruising right now because I feel there's an increased level of comfort & safety in knowing I'm somewhere that has security if needed and keeps track of who is there, in case something happens. I am however struggling to find info on whether or not there's any oversight over safety in terms of sexual health. Is this a BYO Condom & STI Results kinda situation or does it depend from person to person?

Thanks in advance for anything you're willing to share! While I'm mostly asking to satiate some logistical curiosity as I work towards planning my own trip there, I'm also open to hearing hot stories if you've got them 😇

I've been single for the past three years. In that time, I went on one date, but we were better off as friends. I'm on T, unbearably horny, and unbearably alone.

I'm worried no guy will ever like me. Or if they do, they'll just see me as a 'weird woman' because I keep my hair long. Like let me just get a hot guy to rail me, please

How are some of y’all fucking your partner’s ass with your t-dick? Are you grinding between the cheeks, or up against the actual hole? If the second one: can he feel that, and how does he like it? Are you getting your junk into the hole??

Advice on positions, hygiene/UTI prevention, etc very welcome. Thanks in advance!

FWIW I’m about 2 inches hard, and I think I own a pump but I honestly can’t remember if I kept it after using it twice and being underwhelmed.

i wanna be seen by a queer man as a queer man. i wanna be desired. i want him to find my body hot as hell. i want him to admire my hair and fat. i want him to worship my dick the way it deserves. i want him to whimper and cry into me - his only source of comfort and the perpetrator of his destruction.

no actually im not done. i want him to daydream about me sometimes and get a little hard. i want to make him a little nervous. i want to be challenged by him. i wanna have my hands on his beautiful hips and feel his skin against my thighs, i want him to be panting and desperate just for me, i want him to only be able to think of my name.

manifesting fabulous gay sex for us all. this will happen, it is inevitable