Tag: first time

This is part 3 of the tale of my first romp with a transvestite. Read part 1 for the prelude and part 2, the hookup.

Action time! I break out of my “disguise” of jeans and t-shirt to reveal my silky fuscia babydoll and Wolford pantyhose to the lovely Racquel. What a feeling of finally sharing my sexy girly side with another.

My girly cock was thinking the same thing too.

I lied down on her bed and caressed her black stockings with my hosed legs as she approached me. Then the unthinkable happened. She begins to strip down the Wolfords. Uh-oh, instant turn-off.

I don’t think Racquel particularly minded the lingerie and pantyhose (I believe she even called it “cute”) but only saw it as an obstacle to her real desire: get right to the cock.

Ok, so I know we’re not exactly two lesbians going at it but thoughts of manly gay sex began going through my head enough to cause a panic. I always envisioned myself a woman going at it with another hot woman, not two men who put aside their femininity to fuck.

In other words, the Wolfords and the babydoll had to stay on to preserve the “womanly” nature of the fucking.

Fortunately, Racquel played along, began to make fun of me (nicely) and pulled out a pink lace babydoll from her closet, then asked if I like it as she slipped it on. Actually she said, “Will this do, honey?”

Yes it will.

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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.

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Not too long ago, after a failed attempt at seducing a (real) woman, I came to a sudden conclusion.

A little background first. It has always been a deep, dark fantasy of mine to hook up with another transvestite counterpart but living it out in real life carries some issues, especially for a crossdresser that has been hetero all her life.

• I’ll be crossing into the bisexual barrier with no turning back. I have nothing but respect for being gay or bisexual, but it’s a major decision for someone who has has only known being hetero, you know.
• What if I don’t like the experience? Will I feel “weird” and require therapy? Ok, maybe the therapy is a stretch but they are plausible questions.
• Will I find myself transforming from a closet crossdresser to a full time transvestite? Again, it’s a major decision and requires a major life change.
• Will my friends, oblivious to my crossdressing, eventually find out? I live in two distinct worlds that haven’t collided yet.

Of course, with the cons come the pros:

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