In my early 20s I went through a devastating breakup. My girlfriend of several years admitted to fucking one of my friends. I went into a depression and filled the void with porn and eventually, random sex. I got really into TS and gay porn on top of my regular stuff. I found myself browsing craigslist personals in search of my first gay or trans encounter. Trans was a lot harder to find in my area. This was the days before grindr and I didn’t like the exposure of a dating site.
I found a guy looking for mutual fun in an adjacent city, roughly a 90 minute drive. He was my age and moderately fit. White with brown hair and hazel eyes. Not weird looking, and I really didn’t have a gauge for attractiveness in men. Not feminine at all, which might have helped later, but I didn’t have a lot of options. Most of the guys on craigslist were way older, overweight, and extremely hairy. That’s a hard sell for a guy who’s only been with women.