Hiya. Just wanted to ventilate some thoughts. I had my first trans experience when I was 20 about 11 years ago, a paid one. I had no income so I had to figure out a creative way to really safe money to be able to pay for it. First one was no good, I regretted it afterwards with some shame. She wasn't particularly affectionate about it either, even though she knew very well I was a rookie. I sucked her and tried her to fuck me but i didn't work so well.
Through my student years I tried a few times more, all paid, but mostly I just was chasing something I couldn't find. Was lonely and just figuring out myself (to be honest that's a stretch, you always find new things about yourself). Most often it was too professional while in reality I kinda seek something more intimate. Eventually I found that. A Trans brasilian escort in Amsterdam was so into me that she invited to come over during the summer of 2017, while in fact she was working there. I had helped her with some translation for her work, so I scored some points with her. Came over casually, she offered me to eat something since I had traveled a long way. She was very nice, friendly and affectionate. Could tell she was really into me. And I found that out in bed too, didn't take long for her to get into bed and was all over me. She was more top and she explored every part of my body. Said I had a twink body and she loved my ass. So because of the whole vibe and hornyness she fucked me bare, which wasn't part of the plan. But it just happened. I admit I got a bit paranoid about that part afterwards, but it turned out all was fine with my tests. And she was honest: she doesn't really do bare with anyone except boyfriends, but she admitted I was so hot to her that she couldn't resist. Tests basically confirmed she told the truth anyhow. Probably also because she liked me as person as I was helpful. Anyway, still in touch with her. She never came back due to documents and all that. So I don't know if will ever meet again. She's smoking hot though. Her fucking me was very painful the first 10 minutes, but somehow she managed to relieve the pain and in came the pleasure. Probably the only time I actually felt pleasure in getting fucked. The other times I tried nobody tried to loosen me up at all and were unable to have me go through it. Shit is way to tight down there, still is since I haven't really done it too often and spread out over bigger timespan. Most trans I met don't have the patience or skill to help me through it.
Apart from that had some other encounters here and there, also the more feminine TV's. Tried a few things like outside and stuff like that. The only "famous" trans I ever met was Sara Salazar. I posted about it (look in history) before. Met her during King's knight in 2019. Used to cam with her a few times in the past and spoke to her. Always had a plan to meet her, since she was in Germany. She did tell me she was heavily into my body/ass and wanted to fuck. Things didn't happen that way. I was surprised she came over to a hotel I had arranged. She came over tired so what happend was I basically sucked her the entire time until she splattered a LARGE amount of cum on my face and on my eye and eyebrows. Was no real affection sadly, maybe because of her being tired. I left her and checked out myself so she could sleep. I guess due to the whole thing I didn't feel like sticking around. No real effort to have a conversation or to be intimate. Cuddling was not really her thing at the time. If she did I would have stuck around probably. Dunno was a bit weird. On one end she was actually taking a 2 hour trip to come over, but when she was here there was barely any interaction. A bit odd. Maybe it was also the drugs, since she likes doing that I guess.