Lol! Sailor Surpise! Show World was so great! I miss the windowless peeps! Fucking Giuliani, the fascist.
I look back on my career and really recall how I got involved/interested with TS women. I'm glad as hell I found them, but have no clue how it started.....I believe it was back around 2004, when you have to rely on the LA Express "paper" for ads. As time went on, I'm almost strictly hooked on Asian TS women...how bout you guys?
So fucking hot (San Diego).
Yes. She's amazing. When you see her, it's hard to imagine a world in which she did not transition. I saw her a few years back. She was staying in this hotel suite with a full dining table and chairs. the minute I saw those chairs, I knew we would be using one. As she was riding me on the chair, it cracked in half and we cracked up laughing. Good times. And what a great personal story she has... being a nurse and a student before she got into the modeling and escorting game. One of my all time faves.
I ventured into TS land after ending a five year relationship with my girlfriend. After five years of horrible sex, something erotic was the only path to getting back on track 
..by a very cute Puerto Rican girl. I was 19 and thought I had picked up a GG, only to get back to my place and *surprise* there it was. She blew me and I played with her cock a little but it went no further. Didn't actually start seeing TS until many years later. Saw a very hot Latina for my first time (again) and I was hooked. That must've been 2004 or 2005...? I'm still a sucker for lovely Latina TS girls after all these years! God bless their hearts!
After many years of dalliances with a variety of GG escorts, wanting ever escalating variety, I started trying out a few (3 I think) that were a bit into BDSM/Kink. It started out with just tie-ups and spankings along with sex, but eventually drifted into a couple of strap-on encounters. My reactions to the strap-on encounters were a bit mixed; in part it was "oh, damn that was a bit uncomfortable/painful"; in part it was also "damn, that was hot and intense!"
Internet porn was also starting to bloom, and I still somewhat remember my first view of a hot transgender woman stroking. I was utterly fascinated and amazed. In the sub-conscious at least, I'm sure I started considering what having sex with a transgender would be like, though it didn't create an intent right away.
Eventually came to a time and place and cash where I thought I'd try it out. 1st time I got buttfucked it really freaked me out (even though I'd had the strap-on experiences.) Guess I just was kind of reacting with a "what the HELL am I DOING?" thought. But I kept doing it on occasion.
These days, I actually tend to PREFER sex with TG women, seeing GGs less and less often. I love a nice, well-done pounding
Was looking through an issue back in my early 20's and saw an ad for a tgirl not to far from my place.
Went to see her and i had a great time. I had already been to a couple of massage parlors by this point. I was taken aback by the enthusiasm this tgirl put into pleasing me.
Saw her a few times. Then had a weird experience with another tgirl. Stayed away from the scene for awhile.
Years laster, picked up another la xpress. Saw an ad for giselle electra. Almost didnt believe she was real. She was. Blew mind and have chased ever since.
I haven't had the in-person experience yet, though I've cybered a couple of times with a (civilian) T-girl in another city. But I think in some ways my interest has developed in the same way as yours. Just before I semi-retired from the hobby for a while, a favorite provider and I were planning for her to use a strap-on on me during our next session---which never happened, as she retired while I was lying low.
Years of hetero porn consumption = comfort with looking at dicks
Then Joey Silvera bringing TS porn mainstream
The occasional scanning of Unique Encounters (South FL) mag at the adult book store
Tula from James Bond
Then the internet ads and TER
A few chance spotting of ladies out at bars or in public and feeling the attraction
A unexpected detour and visit to the Blue light district in Amsterdam
Letting go of this insane notion that attraction to transwomen makes you "gay"
And moving to a big city where there's a few hot ladies
All conspired to get me walking on the wild side.
I was 19 and went to Show World in Times Square to look at the girls in the one on one booths. The next thing you know, I am with a transsexual-- I didn't even know they existed I was so dumb. I topped her and came in about 3 seconds. It was pre-AIDs so there was no protection. I never looked back. The only thing that has changed is I am no longer a total top.
I lived on the east coast from 1992 to the late 1990's and would take Amtrak to NY from DC at least once per month. Those days at Club Edelweiss were incredible and so unlike anything that exists today. It is hard to pen how crazy and wild that place was and absolutely no rules, at least rules that were enforced.
I'm not sure which incarnation of Edelweiss that would have been but I went to at least three different locations for the club. This, of course, pre-dated the Internet by a few years so meeting girls in person, or in the back pages of The Village Voice, were the only real options then.
I used to pass Edelweiss on occasion when I lived in NYC. I never went in. I wish I knew then what I know now....
I've never been to Thailand so maybe the bars there are similar to what Edelweiss used to be but I've never been anywhere like Edelweiss before or since in North America. It was an insanely fun place.
I don't remember what first got me into it but the first clue I went to was GG's Barnum Room on 43rd St which grew out of the Gilded Grape. After that there was a club on 45th that I don't remember the name. And then the glory of Club Edelweiss. Spent many a great evening there while I lived in NYC and made sure to stop by every time I was in town after.
DOH!!! The Grapevine. another fun place.
Lol! Sailor Surpise! Show World was so great! I miss the windowless peeps! Fucking Giuliani, the fascist.