Smoking Crossdresser Stories

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Your inner femboy

by SkirtSkirt on Feb 10, 2021
Transsexual

The first thing you have to ask yourself is, who are you Are you an ignorant boy about to be turned into a little cum slut?But then who was there to show you who you really are?Or did you do it to yourself? Or are you already a cum dumpster about to reveal themselves? Or maybe you want to be a slutty crossdresser that's secret gets exposed,one throat fuck at...

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My First Time Dressing Ch. 01

by ChrissyCD on Sep 16, 2017
Transsexuals & Crossdressers

This is the first of hopefully many stories to come. This one may be a bit boring and lacking the hardcore fucking and sucking so many of you are used to. I feel the need to tell it because it will give some background to the rest of my stories. For the most part I will send them in chronologically from my younger days to present day as a undercover crossdre...

Everyone has a Freak Flag

by Etaindarcy on May 28, 2019
Transgender & Crossdressers

So for the most part, having sex while crossdressing is a bit of a fetish and once people know you are into it they are now free to share their own fetishes with you. That's where my next life lesson comes in and I have a couple of stories about people doing some surprising shit near me or to me. Around 26 years old, I was now going by the name Amanda and I...

Things That Turn Me On

by Raquels_Panties on Apr 22, 2020
Fetish

I'm a 28-year old male. I live a normal life in public. I like women and men. I'm 5'8" tall and weigh 135 pounds. One might consider my features, my face, my body shape, more on the feminine side of the spectrum, than on the masculine. I'm okay with with that. I use this to my advantage and have allowed my hair to grow out. It falls just below my shoulders....

Barrack Room Betty Ch. 01

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Chapter One - Wish I Was Wren "Wish I was a Wren," Recruit Brian Perkins mumbled under his breath. 'Fuck! I wish he hadn't said that!' thought Recruit Michael Nyland. He knew that no good would come of it. "Your wish might come true," Leading Recruit Jason Jones (Spike to his friends) sneered. Michael Nyland shivered, and not just because he was standin...

Cheating

by twizted77 on Dec 26, 2018
Cheating Spouses

You never thought it would happen, but here you are after years of marriage, waiting quietly at a dark table in the corner of a hotel bar to meet someone you'd connected with online. Someone who, if things went well, you would be having sex with later tonight. You take a shot of tequila and breath deeply. It burns, but you barely feel it. You are a mixture o...

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The Roommate Pt. 17 - Miranda

by ValoryG on Sep 19, 2017
Transsexuals & Crossdressers

Lori missed sex with Nathan and had some hot solo sex while replaying the mental video of the lawyer fucking her. Thrusting a big dildo into her ass while imagining Nathan's rod was stimulating but it just didn't match Nathan's real cock and body. Still, Lori wasn't the type to call him at his law office. She even fantasized about having a three-way with...

Sarah was Naughty in the Hot Tub

by SarahCD on Sep 14, 2017
Transsexuals & Crossdressers

Late last night I went down to the hot tub in our complex. I wore girl's bikini panties under my cutoff shorts. I always pick out my brightest sissy girl's panties. They were bright red with yellow roses on them. Over them I put on a pair of worn-out white shorts. If I were seen walking down there no one would suspect what I had on underneath. However, the c...

I Adore Crossdressers

by Ab9095 on Nov 26, 2018
Transgender & Crossdressers

I adore crossdressers. Adore!! Pretty little pantied asses up in the air. Shaved dicks and balls hanging down. Pretty little assholes. Fuck Yeah!!! I love seeing their hard dicks flopping when they are riding a cock. Fucking A, when they are hot they are HOT!!! They don't have to be perfect any more than any woman does. They are ALL good. But I do love it...

Glory Hole

by GateKeeper_A on Jun 11, 2014
Group Sex

Last month, you had discovered that your local adult novelty store had a glory hole. Since that day, that glory hole has been all you can think about. Every time you close your eyes, you picture a cock sliding through a hole towards you. Every time you masturbate, your mind is filled with fantasies of strange men's cocks. You shudder with a mixture of trepid...

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