Saturday, March 24, 2012

my first cross dresser

I did this hook up a while ago, but just have not gotten around to writing about it so apologies as the details may not be so clear. I am a very queer, pansexual type of guy. While i've mainly, well lets say exclusively, been into fucking non trans dudes lately, I am very open in regards to gender.

This person hit me up, I think through craigs list. Her picture is of a beautiful, sexy woman, long brown hair, sexy long legs. She/he identifies as a cross dresser. When in dress they go by she and when out of dress by he. I have never hooked up with a cross dresser before - well that i know of. She/he says she wants to dress for me and then fuck the hell out of me. Hot.

I know that cross dressers are not always welcome amongst us trans folks. And I get and understand where that comes from – trans folks struggle and deal with shit 24-7 for being trans or genderqueer and the idea of people being able to take gender on and off or to use it to get off brings up complicated feelings. I get that.

However, I want a world where all genders are celebrated, where gender can be fluid, where changing and playing with gender is sexy and hot and doesn't need to cause pain.

While I know we do not live in that world i wish we did.  And while i have made many missteps, i strive to create that world in how I interact with other folks who do not easily fit into main stream society's ideas of men and women.   However, I do admit I feel some kind of way about people who play with gender and make a ton of money off it yet don't ally with us trans and gender queers – to me that's not about them being cross dressers that's just about them being wrong and capitalists – which occurs regardless of gender.

That all said onto the hook up. I get to their place.  I remember dark colors, darks reds, some frill here and there.  I luv it. I'm a little nervous though. I've just been in such a masculine space lately and I'm just not sure how i'll feel in this situation. She lets me in. She is wearing a sexy red dress, long hair, heels. She pours me some wine. We exchange the usual pre-fuck chat – home towns, work, etc. I ask her what pronouns she prefers. She says either is fine but I can use she for now.

She says in an ideal world she would be able to go to work one day as woman and the next as a man and it would all be ok. I decide that she is wonderful.

Then we get to fucking. Again this happened a bit ago so I don't remember all the details but here are some highlights. We are sitting on her couch. I kneel between her legs, push up her skirt, pull out her sizable cock and take it down my throat. She pulls me up, turns me over and thrusts inside my cunt. We move to her bed. She raises her ass in the air and tells me to spank her. Which I do. She moans saying 'harder' until she can't take it anymore and pushes me onto my back. She climbs on top of me, spreads my legs and pushes inside me. She's fucking me hard and frantic and groans as she cums in me.


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