First!

[stillies77]

gia darling in TS heartbreakers 1

[Darkwing Duck]

Whoa, wait, I totally forgot about that HBO Real Sex episode that had Brandy Scott and Kelley Michaels!

[freudian1]

Kelly Michaels in a film called, "Mr. Madonna." Hot, hot, hot.

[arc angel]

around 84 shannon i think it was ( bless her).. i still have the mags , ( not for sale ) ... sulka is in them ... and i still look at them ... there is a few girs i do not know who they are in the mags but they are hott!!!...
one looks like my ex.........and i love it !!!!!...

[Fox]

The first time I every saw a T-Girl was in Live Young Girls mag when I was 15 (sometime in 1998, methinks). I didn't know they existed before then.

As far a more well known TS, probably Allanah Starr. I remember a few cumshots from a set with her in red lingerie on Shemale Yum. Man, those really sent me of the edge on my jerk sessions lol.

[Zentow386]

My first was Giselle.

Its because of her I am into TS.

[bigbillyc]

mine was Toni rom the original shemale encounters loops. when she was all in the leather and had her slave there i was wishing i were him, right after that it was Carnal Candy who's pics i still look at once a week

[EdelweissFan]

I guess this is really going to show my age. The image actually was not of a transsexual, but of a gay man/transvestite, apparently named Ernie Thormahlen.

Way back in the 1970s, when I was in junior high school, my sister brought home an album by the now legendary proto-glam rock star Lou Reed, entitled Transformer. When I listened to the lyrics, I could barely comprehend the lifestyle that was being described, but I knew it was kinky and knew it had something to do with people I only knew as "faggots."

But what blew my mind was the back of the album cover. It showed two pictures -- one of a hyper butch, but obviously gay many with an erection showing through his super tight jeans; the other of a hyper feminine woman in full on fetish/lingerie, stockings and high heels. I thought she was the sexiest woman in the world and fantasized about being with her.

Of course, the image was an illustration of the songs and album title, Transformer, and such lyrics as "then he became a she." I did not let myself think about that and assumed that they were supposed to be boyfriend and girlfriend. It was probably another ten years before I allowed myself to fantasize about her knowing that the image was actually of a transvestite.

It's strange to think that a lot of my sexuality has to do with the impact of this image I saw over thirty years ago.

I searched the internet in vain for that back cover. But guess what? I still have the album and scanned the image for you guys. First, just the transvestite, then the two images.

[needsum]

Mine was of Vanity. I don't remember the porn, but after I had drooled over the Tgirls on eros long enough I made the leap and ordered a tranny porn tape and some toys from some porn catalog.

The vid had vanity with a bunch of guys wearing odd masks, like halloween masks or something. There were three or four of them down on all fours and then there was Vanity, being sucked by them and then fucking them.

I didn't really get off on watching the guys get fucked, but man, did I LOOOVE seeing Vanity in all her glory.

[Ecstatic]

Most likely Sulka, but it was soooo long ago, who knows for sure.