“Can you wear a dress tonight?”
“I can’t crossdress in public, I’m not ‘out’ and don’t want to be seen that way.”
“That’s okay. We’re going to a gay-only club that has a drag queen show tonight, so you’d fit right in.”
“Cool, but I’ll have to change when we get there.”
“Awesome! See you tonight!”
And that was my conversation with a new lover I just met on AdultFriendFinder. The guy is in his upper 60s, gray hair, wrinkles, very masculine, exactly what I am attracted to. He likes the fact that I am a sissy femboy, that I shave myself smooth everywhere and wear girly panties and even lingerie. Eve though I am 41, I look, feel and even sound younger, and I am young at heart. I am not ready to be the mature one in a May-December relationship yet, I don’t want to be the older lover or Daddy yet, that is what I want in a partner and I am trying to stay “young” for as long as possible, until it is no longer passable for me. I am the k**, the boi, the little “girl,” the weaker, vulnerable one in a relationship.
The guy, lets just call him by the generic name “John Smith,” and I had been texting, emailing and doing cam to cam together for days and finally decided to meet up in person. He picked me up at my place and we went to a gay-only club in Hillcrest here in San Diego. I have never been in a gay club before. Same-sex partners, both male and female, were everywhere showing their love: talking, flirting, hugging each other, holding hands. Just like any other club I assume, but gay. Past the bar was a stage where there would be this club’s monthly drag queen show. “John Smith” told me he really loves drag queens, shemales, crossdressers, and transgenders and transvestites. I guess he liked getting the best of both worlds?
When we got our table I said, “I’m gonna go change.”
“Okay, honey,” “John Smith” responded.
I found the bathroom and entered it cautiously. I am still new to this and sort of embarrassed to be seen in a gay club, much less in drag. To my pleasant surprise, there was no one in it at the time, and I found a big handicap stall that I could dress in comfortably. I took off my clothes except for the purple lace thong panties I was already wearing, then slipped on a one-piece sleeveless mini-dress that was open in the back, showing off my shoulders, my entire back down to the small of it, and most of my chest, except for my boytitts. The bottom of the dress was very short, in the back it barely got past the bottom of my buttcheeks, in the front it barely covered up my crotch. When I walked you could almost see my panties. “John” said he was “a leg man,” so the dress was perfect because it should off my long, smooth legs all the way up to my hips and bikini line. The dress was purple with flowers as a design, I wanted something that was as feminine, as girly as possible.