Hits, Misses: G

Ok, what follows are some accounts of hookups and almost hookups I've had with transwomen in the late 2000s, early 2010s. Some I think about a lot. Others I've forgotten completely and am attempting to interrogate my memories. Things have changed a lot in the culture, mostly for the better. Visibility is way up, Taboos are less so, information is more widespread, hookup aps are a thing, etc. I'm a Cis-Het White man, a nerdy introvert aged 19-24 during the time of these events.

Probably the hottest hit wasn't the first encounter I'd had with a transwoman. I was between serious relationships, depressed and just wanted to fuck. I returned to Adult Friend Finder volunteering only as much as I could get away with. I only had my eyes out for transwomen. And there were none on the site within 50 miles. Meetups usually involved 1+ hour drives, extensive planning, etc. the site is super hostile unless you're paying for it, but you could bump messages back and forth with their IM feature. I’d struck up contact with a black TS, G, late 30s, about 90 minutes away. We bumped messages and texts back and forth for a few weeks. She was very nice and chill, but often replied to general “whats up” questions with “nothing” or “I don't know” so it was hard to get a conversation or discussion rolling with her most of the time. she was quite forthcoming with pics though. Often bathroom mirror selfies of bra & panties, or topless. She was thickish, as adult black women are, not outrageously curvry, but very nice. Massive breasts. C+ or D. complexion like milk chocolate candy. 100% passable, Dark glasses, the “Rachel” hairstyle, very thick sensuous lips. She never smiled or grinned in her photos, though I think that was just the look she was cultivating. Her expression was much less dour in person. Anyway these details are interesting to me so I recount them here. She lived full-time, used estrogen injections when she could get her hands on them, which was kind of infrequently. Though they worked wonders for her skin and figure.