The one that got away.

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?

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u/Miles_Long_8853 — 1 day ago

Stroking at my desk

Ignore the messy art supplies under my desk. I was really feeling myself in this jockstrap.

u/Miles_Long_8853 — 4 days ago

[TM4TM] (cis okay) Looking for partner in France or elsewhere in Europe

A little bit about me: I’m a 33 year old gay trans man, an American who relocated to France. I’ve lived many different lives. I was a baker for six years, a rabbinical student for five, then the owner of a tiny farm in central NY, and I even did a stint at a wooden boat-building program. Now I’m starting something I plan to last me the rest of my life, if all goes well: cabinetry. Art and writing are also very important to me. I’ve been writing short stories and poems since I was 15, and I do a lot of ink and charcoal drawings. I love learning new crafts, and I really love hearing about the things other people make. Videogames and anime used to be a big part of my life, and I’ve been rekindling my interest in them. (Ask me about my JoJo figurines.) 

I’m looking for a partner, ideally long-term. I would prefer someone around my age or older. I’m drawn to people who like to chat about anything and everything. Curiosity about the world is very attractive to me, as is knowing what you want in life (to some extent, at least). A concern about others is also very attractive to me, as well as a strong sense of humor. Life is absurd, so we may as well laugh at it!

I'm interested in trans and cis men equally, and I don't have a physical type. I have a very high libido, and physical touch in general is important to me (cuddling, etc). For the sake of compatibility, I'll share that I'm mostly a top, I’m very kinky, and I like to be in control. That being said, in the context of a committed relationship, I'm very comfortable with a give and take, and with exploring beyond my comfort zones. Kink is something I would need in the relationship in some capacity, but I don’t expect my partner to fulfill my every sexual desire.

I’m in France, but I’m happy to date long-distance within Europe, as long as we would get to see each other in person with some frequency. I would theoretically be okay relocating somewhere else in Europe for a partner, but I’m in France for the foreseeable future, since I’m just starting a new career path here. I also have family here who I’m very close to, and I wouldn’t want to be too far from them. If you live elsewhere and you think you might actually relocate to France/Europe at some point, that could work, too.

I’ve only ever been in monogamous relationships, but I’m curious about non-monogamy. Right now, I would be comfortable with either a monogamous relationship or an open relationship where I have one committed partner and we play with others on the side (or together). I want to be the locus of my partner's romantic life, and vice versa. That could change, but that’s where I’m at right now. I’m very happy to talk about this at length with anyone who’s interested. 

Ultimately, I want to date a guy who’s also my best friend. To me, a perfect day sounds like the two of us having breakfast together, half-dressed, then doing our own things separately or side by side, and then coming together later on to chat, snuggle, fuck, vent, and just reconnect and enjoy each other’s company. 

If you made it this far, thanks for reading!

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u/Miles_Long_8853 — 8 days ago

Be a man.

You've already failed as a girl. What choice do you have? Take your shot, do the chores you keep putting off, and stand up for yourself. Stop delaying the inevitable. Get out of bed. Oh, you're horny? Again? Stop whining, stroke your cock, and then go do the dishes.

u/Miles_Long_8853 — 13 days ago

[FtM4FtM] in France or elsewhere Europe, looking for relationship (cis okay)

A little bit about me: I’m a 33 year old gay trans man, an American who relocated to France. I’ve lived many different lives. I was a baker, a rabbinical student, a farm owner, and I even did a stint at a wooden boat-building program. Now I’m starting something I plan to last me the rest of my life, if all goes well: cabinetry. Art and writing are also very important to me. I love learning new crafts, and I really love hearing about the things other people make. I'm also into videogames and anime. (Ask me about my JoJo figurines.) 

I’m looking for a partner, either short-term or preferably long-term. I would prefer someone around my age or older. I’m drawn to people who like to chat about anything and everything, and people who are curious about the world around them. A concern about others is also very attractive to me, as well as a strong sense of humor. Life is absurd, so we may as well laugh at it! 

When it comes to sex and sexuality, I’ll just sum myself up in a few sentences for the sake of keeping this a post and not a novel. I love men, both trans and cis, and I don't have a physical type. I’m very kinky, I like to be in control, and while I’m naturally caring and affectionate, I also have a sadistic streak. Kink is something I would need in a committed relationship, but I don’t expect my partner to be a kink-dispenser or to exist to fulfill my every sexual desire. 

I’m in France, but I’m happy to date long-distance within Europe, as long as we would get to see each other in person with some frequency. I would theoretically be okay relocating somewhere else in Europe for a partner, but I’m in France for the foreseeable future, since I’m just starting a new career path here. I also have family here who I’m very close to, and I wouldn’t want to be too far from them. 

I’ve only ever been in monogamous relationships, but I’m curious about non-monogamy. Right now, I would be comfortable with either a monogamous relationship or an open relationship where I have one committed partner and we play with others on the side. That could change, but that’s where I’m at right now. I’m very happy to talk about this at length with anyone who’s interested. 

Ultimately, I want to date a guy who’s also my best friend. (Not my best friend to the exclusion of all others! Healthy boundaries are incredibly important, as is having a wider support network than just one’s partner, when possible.) To me, a perfect day sounds like the two of us having breakfast together, half-dressed, then doing our own things separately or side by side, and then coming together later on to chat, snuggle, fuck, vent, and just reconnect and enjoy each other’s company. 

If you made it this far, thanks for reading!

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u/Miles_Long_8853 — 17 days ago

About 9 years on T

I usually feel pretty good about my dick, but it's just one of those nights when I turn to the internet for a little validation from strangers. Soft here, just whipping it out at an airbnb.

u/Miles_Long_8853 — 22 days ago

A bittersweet goodbye

I just moved in preparation for a new carpentry apprenticeship I'm starting in the fall, and I had to say goodbye to a sweet cis boy I had been hooking up with somewhat regularly. He stopped by last week on his way to a drag show, dressed to the nines in a shimmery body suit and platform boots. We chatted for a while and then he gave me That Look, batting his eyelashes at me. I said something like, "You want something, beautiful?" I know it's corny, but he loved it when I call him 'beautiful.' He grinned and told me he wanted me to fuck him one last time.

Of course, as soon as I got his clothes off and I saw his hole waxed and lubed, I realized this wasn't exactly a spur of the moment decision on his part. Cheeky boy. I got him on his stomach and spent a long, long time eating him out, losing myself in the way he kept whimpering. He barely speaks any English, and hearing him beg in a heavy French accent was so sexy. I always used to tell him we could speak French together, but he insisted on trying to meet me halfway with a little English.

I never even reached for my prosthetic that night. I ended up rolling him onto his back, grabbing his hips, and grinding my t-dick into his hole. He was loose enough that I slipped inside, and I held myself there and just ground into him. I thought it might not be enough for him, but he just kept looking up at me with those big eyes, stroking his cock while I pushed against him. He came after only a few minutes. I was too overstimulated to cum, but it didn't matter. I had gotten inside him; I had tasted him; I had heard him beg. For me, that was already a perfect night. We spent a long time kissing on the bed, and then I licked the cum off his chest. He made a face, which was cute. I bent down and kissed the heart tattoo he had on his sternum, and then I asked him about the dangly earrings he was wearing. He's very stylish.

Afterwards, he realized he was late for the drag show, and he ran around the apartment, putting his clothes back on and reapplying his lip gloss and the shimmery stuff on his cheekbones. I know *nothing* about makeup, so don't judge. We said our goodbyes with a few more kisses, and I watched him run to catch the tram.

This boy will always be very important to me because he made me feel like a king when I was really struggling with some very heavy bottom dysphoria. Whereas most of the other cis guys I had been interacting with treated me being a top as utterly absurd, he had simply accepted it without question.

Wherever you are, I wish you nothing but the best in this life.

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u/Miles_Long_8853 — 1 month ago

I know pride is a sin, but...

And I know it's unhealthy to compare myself to cis guys, but...

I just learned that a toxic cis top in my social circle who loves to stir up drama among the bottoms on his roster just lost two bottoms...to me. To make a long story short, there's this big, burly top in my queer reading group. A handsome guy, and he seemed nice enough. I've been hooking up with two other guys in the reading group, one cis and one trans, and separately they told me that they used to sleep with this other top off and on, but he got way too toxic, and they decided to cancel their dates with him to see me instead.

Let's just say I'm feeling pretty good about myself right now. Guys, it pays to be a caring and considerate top!

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u/Miles_Long_8853 — 1 month ago

First sauna experience (very tame, still excited about it)

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.

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u/Miles_Long_8853 — 2 months ago

Anonymous sex as a top/side

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).

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u/Miles_Long_8853 — 2 months ago

New position unlocked

I finally did it! I played with a guy's hole *while* he was sucking my cock. He was on his hands and knees at the edge of the bed, and I was standing in front of the bed. If it helps to imagine it, we were forming a sort of L shape with our bodies. He had his head turned to the side, and while he sucked me, I was able to reach down the length of his body and play with his ass and hole.

This was euphoric for so many reasons. Firstly, this happened to me years ago, only the positions were reversed. I remember being annoyed but thinking that I *would* have been into it if I had been on the other side of it (a thought I've had so many times back when I used to exclusively bottom, which eventually made me realize I was very much a top). Secondly, this always felt like a position I could only achieve as a cis guy - so it feels really amazing to be able to do it. And thirdly, it's just so hot, playing with someone like that. He was really into it, too.

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u/Miles_Long_8853 — 2 months ago

No stories this time, I just wanted to shout out hairy asses and how amazing they are to eat and fuck. I never used to be attracted to body hair before T, and now it gets me so hard. Especially hairy pits and hairy holes.

I hope everyone reading this has a fabulous day.

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u/Miles_Long_8853 — 2 months ago