A Tale of a Crossdressing Fantasy

This post first started out being a quick afterthought of my deepest crossdressing fantasies (with pantyhose of course), yet somehow blossomed into a longer erotic story. It’s funny how when you start writing about something you can’t stop thinking about, words just flow and you just can’t stop.

More like I don’t want the fantasy to stop either.

So I hope you enjoy my personal fantasy tale and tell me what you think in a comment below. Leave one of your own fantasies (though much shorter) if you so desire.

* * *

Adriana invited me over to her place for a cup of coffee to which I happily obliged. I had met her rather randomly passing by on a downtown street after noticing she was wearing shiny pantyhose, something you don’t see too often on a rather hot summer day. I also took notice that she appeared to be a transvestite, though very convincing, since it took a double take to spot.

After catching her eye, I commented “I wear them in the summer too,” not knowing whether she would stop and ponder the comment or just keep on walking past. To my luck, it was the former. “Oh really?” she asked. “Well, call me and we’ll compare notes sometime,” she added as she handed a business card to me then walked off with a flirty stare.

I excitedly called her later that same day and had a nice conversation about everything BUT crossdressing, which was unexpected. Then, of course, the topic came up where I eventually admitted my in-closet crossdressing and love for pantyhose. She laughed, “Am I your therapist now? But really, that’s cute. Why don’t you come by for a coffee and we’ll talk more.”

On to the “cup of coffee.” I arrive at Adriana’s and she greets me dressed in a rather seductive black mini-dress and the same suntan shiny pantyhose I saw her wearing earlier that day. Coffee? Yeah right. It doesn’t mean I am not into whatever she is thinking though.

We talk, you know, that same old casual get-to-know bullshit when meeting a “date” when she then suddenly asks me directly, “What’s your wish?”

I respond with the first thing on my mind, “How do you make me look as stunning as you?”

Seemingly flattered, she says “Come this way,” as we walk into her bedroom.

OMG, I’m thinking as she let me have a look through her drawers and closet to pick out something to slip into. I’m impressed by her collection of lingerie that would surely put genetic women to shame. I chose the “cosmetic” colored Wolford tights, still new in the package, from the dresser drawer.

Let’s see, yes, I’d like that sexy black Sabrina babydoll hanging over there, too. I can tell by the look Adriana gives, she agrees.

Then through the myriad of stiletto heels in her I closet, I spot a pair of black six inch platforms that screamed at me to wear them.

“Well what are you waiting for? Try them on!” she says excitedly.

I strip off my completely unfeminine attire of a t-shirt, shorts and boxers.

“Oooh, shaved. You just might do after all,” she mutters. This flatters me. A lot.

I slowly slip on the tights and babydoll and try on the stiletto platform heels. Wow, the incredible rush of being en-femme in front of a beautiful transvestite overcomes me. I have to contain myself in order not to come right then and there. Luckily I save it.

Adriana sits me down in a chair in front of a mirror. She grabs a black wig with long straight hair and places it gently on my head. After a few small adjustments, she then brings over a tray of makeup.

“Time to make you look like a REAL girl now,” as I helplessly oblige.

I have to admit, my excitement was lost in the fifteen minutes or so it took to apply that makeup. I wondered whether this was even necessary since I was hot to rub our silky nyloned legs already.

But then, after she was finishing up, I see the true feminine artist that is Adriana. I can’t believe my eyes! Was this me with pouty bright red lips, porcelain face and seductive, smoky eyes? OMG, “I’m a real transvestite,” I am thinking as my excitement overcomes me once again.

Apparently Adriana felt the same way as she slid off her mini-dress, revealing a sexy black lace push-up bra and those shiny pantyhose. She then straddles me while I am still seated and doesn’t hesitate to shove her tongue down my throat. Then she begins to grind her now rock hard cock against my equally bulging cock.

The feeling of our silky, pantyhosed cocks together was almost too for me much to bear.

She stops, stands up and, without saying a word, grabs my hand and walks me over to a desk. I watch with confusion as she pulls the desk away from the wall. She then reaches for rather thick strands of nylon cord from a box underneath the bed while I admire her pantyhosed ass bending over. Now it all makes sense.

“Do you like being tied up?” she asks, as if providing a disclaimer.

“Rest assured, a disclaimer is not necessary,” I reply.

She smiles and positions me facing the front of the desk. Adriana doesn’t hesitate in tying my pantyhosed ankles to each leg of the desk. She then gently pushes the rest of my body forward so it is lying on top of the desk and ties my wrists behind my back with another strand of cord.

Adriana then puts the cherry on the cake, so to speak, a ball gag over my head and mouth. I am now immobile with my legs bound about four feet apart. I start to get such a massive rush from being encased in this silky helplessness.

The real fun apparently starts as she rips a hole in the back of my tights, right where my ass is conveniently located. Her cock begins to poke around until it slowly enters my sphincter. We both release a passionate “Oooooh!” in unison.

Adriana thrusts slow at first but picks up the pace. I scream, feeling as if I were being raped, but actually enjoying every second of this violation. I’m adoring her moans in her cute feminine voice while she bangs me like only a true tranny would.

The thrusting eases and then she stops. Funny, I don’t hear the cry of an orgasm from Adriana and don’t yet feel any hot wet come on my ass.

“Did she come ‘inside’ me?” I wondered.

But then she walks around the desk, into the space she created from the wall, and stands directly in front of me. I watch as she removes the condom, still glistening from the lube, and tosses it into the trash. She removes the ball gag from my face and, still visibly hard, slowly thrusts her cock down my throat before I could even get a word out.

I could taste the latex flavor still remaining on her cock as she eases in and out, slow at first, then picking up the pace once again. I’m not exactly used to giving blowjobs but when “forced” to do so, well, let’s just say I’m probably more into it than Adriana is. My bright red lips press tighter and tighter and I suck harder with each pass of that tranny cock in my mouth.

Adriana moans in pleasure and then I hear a higher pitched “Ahhhh” as she slows down fucking my mouth. “My god she just came in my mouth,” as I thought for a second what to do. I guess this is where I find out if I’m a spitter or swallower.

I chose the latter but first taste her love juice for a few seconds. Adriana smiles in satisfaction as she watches the gulp in my throat.

“Taste good?” she asks. Yep, just like candy.

I am overcome now with this strange feeling of being a slut. I’m not talking about the feeling when crossdressing and pretending to be one, but actually living it out in real life. I initially feel some guilt yet, I finally feel like a real life slut, something I’ve imagined all those times I’ve crossdressed (alone).

Adriana unties my arms from behind me and releases my ankles bound to the desk. She grabs my head and gives me a deep, passionate kiss as if trying to taste the last remnants of her earlier deposit.

She then picks up the strands of rope, smiles and hands them to me.

“You turn now.”