Gay Crossdresser Stories

23,018 results
Orientation
Length
Source
Infinite Scroll

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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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...

The Craigslist Killer Pt. 02

by thrillerauthor on Sep 15, 2017
Transsexuals & Crossdressers

© 2014 by Nom de Plume * "Missy, are you still there? Please don't hang up on me!" "I'm here." "I really want to see you." "I don't know, Ron...let me sleep on it, okay?" "Sure, Missy, whatever you say. Can I call you tomorrow?" "Okay. Bye Ron." I hung up before he could say goodbye. For a moment, I was actually going to give in to him! It did sound...

Playing Pregnant

by theonewhowas on Sep 16, 2017
Transsexuals & Crossdressers

I'm a sissy. I used to be a femboi, then I was a crossdresser, and now I'm a sissy. The main difference between the crossdresser and sissy phases was the attitude; before I was a guy doing this for fun and to be admired, sexually – to confuse straight and gay boys alike. But now, as a sissy, I was devoted firstly to my master and love, Noah, and secondly to...

Super Heroes Ed. 02

by grgy56 on Mar 2, 2020
Transgender & Crossdressers

Super Heroes - Edition 2 There I was. Standing in the front of the full length mirror dressed as Zantanna Zatare - Justice League of America superhero. From the top hat with my long, flowing raven hair cascading down over my more than abundant breast forms barely contained under a tight fitting, frilly blouse and jacket, to the panties that formed my penis...

The Deviants' Room

by sissyrikki17 on Oct 14, 2017
Transsexuals & Crossdressers

Upstate New York, 2007 - Day 1 They all kept talking—bitching—about "sloppy seconds" but if you're drunk enough, and these guys were drunk most all the time, you don't really care about dipping your wick into a hole filled to overflowing with other guys' junk. You just stick it in, numbly hump for a few minutes, then make your own delirious contribution to...

Silken Seductions - Step 01

by AdamZasse on Sep 14, 2017
Transsexuals & Crossdressers

It was one of those days at work. Nothing was going right and I was getting a headache. I slipped out a half-hour early and headed home for aspirin and a hot shower. I was surprised to see my husband's car in the driveway so I thought I'd surprise him and get him in the shower with me. I stripped down to just my panties while still down stairs and padded qui...

Queens of the Desert

by Alluring_Crimson_Shifter on Sep 16, 2017
Anal

Joseph Prince was in his nano-physics bio-chemical lab located in Maryland. Taking a break he enjoyed his pastime of listening to Michael Jackson music and doing a moon walk in the lab. He was wearing a white silk shirt with frills under a black jacket similar to one of Michael Jacksons and was laughing at his rendition of the dance steps. He had a similar t...

Our Conquerors, Our Concubines

by Shendude on Dec 20, 2010
Science Fiction

Millenia ago, an alien race created the Ghirabo, telepathic shapeshifters intended to serve as sexual playthings, able to read their owners' minds and assume a form and personality that will fulfill their owners' desires. But the Ghirabo's Creators were wiped out, leaving them to fend for themselves. In time, the Ghirabo have become a powerful race, creating...

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