Peeking Outside the Closet, I Like the View! (Part 2)

Lacey camisole, shiny pantyhose
Lacey camisole, shiny pantyhose

This is part 2 of the tale of my first romp with a transvestite. Read part 1 for the prelude.

Just to recap, I was on the verge of taking a major life turn by venturing out of the lingerie closet and into the transgendered world. Just some mingling with the gurls.

In other words, I was starved for a girly hookup. So why not just do it? Mosey on down to the nearest gay bar or, even better, a gay-friendly neighborhood and everything will probably take care of itself. That was the plan anyway.

Time to prepare. Shower, shave (everything of course), clean out my ass and slip on my favorite silky fuscia babydoll and some Woldford pantyhose. OK, I’m an absolute little bitch when it comes to going out in any kind of en femmme, so a disguise of jeans and a t-shirt went over these.

Alright, take a deep breath. Time to head on down to the gay district, toward the evening time, like a lamb sacrificing itself to the wolves.

Well, that was too easy. Almost instantly, I passed by an, ooh, sexy transvestite in a tight spandex dress, with American flags all over it, some t-a-l-l heels and black stockings. To my delight, she cheerfully flirted, “Where are you going?” and I met Raquel.

We made the chit chat and, eventually, I casually mentioned I was a crossdresser (such a relief to finally tell someone in person!) then raised my jeans to show a little Wolford shine to Raquel to which she gave a gentle feel up my leg and a smile.

I could only explain the feeling at that exact moment as one that I’ll never forget, much like the time I lost my regular virginity. Full body trembling, a raging, painful boner and that excitement knowing you’re getting laid without really knowing what it’s like.

And here we go! Off to Raquel’s. I was shaking with such excitement, I couldn’t speak without a tremble in my voice. I could tell Raquel was eagerly awaiting to teach me well with all her little giggles. We finally get to her apartment and she makes me wait while she “tidies up,” then dims the lights while lighting a few candles.

Moments later, the boundary was to be crossed.

So how did it go? Well, in one word, weird. Just like the other first time.

Stay tuned for the rest.

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