It's a gradual, slow thing.

You notice the big changes, of course. He starts growing out his hair after keeping it short for most of his life. Rather than the rough, unkempt state it would be in before when it needed a trim it looks neater, healthy, like time is actually spent on it rather than it just being an after thought.

One day he adjusts his hair and you notice the new gleam that was never there before; his ears are pierced! He's a little sheepish when you ask to see, but he obliges. There's a kind of nervous tension as he lifts up the curtain of hair. It really has gotten long, hasn't it? The way he holds his hair up to the back of his head looks pretty feminine, and if you didn't know better...

He coughs, and your stupor and hard stare on his neck breaks. There's a warm red hue in his cheeks. He shouldn't be the embarrassed one here, and you realize that normally you would have received some teasing, yet he's been unusually quiet. You chuckle, and make some off-hand comment about the piercings looking nice as your eyes drift down. His breath is quiet but you notice his chest heaving.

The biggest issue keeping you from noticing is how normal it all still is. Your friend is changing his style, sure, but it's still the same guy deep down, right? Waiters and other service staff would 'accidentally' address him as a woman before self-correcting (because of the long hair, of course), and that was a fun thing to tease him about initially. It was different now, though. He'd get happy about it in a way that he isn't usually, and it was almost as if he didn't mind whatever comment or joke you made about it after, almost like he enjoyed it.

The break-down moment was when you went back to your hometown together for the holidays. When you visit your parents, your mother almost immediately asks if you're going to introduce her to your new girlfriend. You start laughing and ask if she's serious. She's known him her whole life, so you begin explaining who it is and turn to see that he is blushing, hard. Your mother is just as embarrassed, so the moment dies quickly. He does practically chug his glass of wine, though, and the next one, and by the end of the night your friend (who is apparently a lightweight all of a sudden) is pretty drunk.

You help take him to where he's staying, and you've really got to support him and move him around. He's softer, lighter than you expect? Little noises come out of him, but not of exertion or effort, something else. If you close your eyes, your mind starts drifting places its never been before. When he finally hits his bed, the moan he lets out when he stretches and yawns officially activates you. You mutter something as you realize you're turned on, look for a blanket or something, and by the time you look back he's stripping his clothes off. Wait... he's wearing a bra? All of a sudden it's like you see him in his entirety for the first time in forever. You finally get the big picture; his long hair, his soft curves, his tiny bulge... Logically, you recognize your friend, but the animal part of your brain, the piece that deals with desire, can only recognize a very pretty girl, nearly naked in bed.

Apologies for the self-indulgent, longer prompt :) It got a bit away from me but it's actually my birthday today and I'm reflecting. I've had a fantasy for a while about someone I've not been totally transparent with my gender about recognizing the effects of HRT on my body. Could be a boss, one of my parent's friends, a professor, I think there are a lot of interesting options. I'd love to explore this or just chat about really anything to do at all with gender today.

I've got a lot of kinks, but the primary ones are probably pet-play, humiliation, breeding, free-use, much older partners, cheating and any kind of corruption / ownership control.

Limits: Gore, filth, extreme violence

I'd prefer to chat through reddit's systems. I appreciate you reading this much :) Let me know what you'd like to talk about and a little about you and I hope to hear from you soon!