my life (ch. 11)
By bijim 15 May 2020
we meet the owners and get acquainted to these remarkable people
Gay Crossdresser Stories
GayDemon's Stories: On this page you can find erotic fiction where you can read about men dressing up as women and gay sex with transvestites and crossdressers.
Muscleboy Double-Teamed in the Gym Shower (ch. 3)
By GameBoy94 9 May 2020
The second part of Jake the muscleboy's steamy molestation on a late-night train car.
Crossdressing faggot meets a brutish construction worker
By Alex Walker 8 May 2020
A crossdressing fag makes a mistake that catches the attention of a burly construction worker and is invited over for some fun.
Muscleboy Double-Teamed in the Gym Shower (ch. 2)
By GameBoy94 8 May 2020
Jake the muscleboy finds himself longing for another encounter like the one he previously had in the gym shower. He also starts wearing tight girly clothes underneath his regular attire to prepare for such an encounter. Little does he know that his deepest, most perverted fantasies are about to come true (again).
Nocternal Eminations
By Mikal 7 May 2020
A story about being abducted and fucked by demons.
I Love Being a Faggot
By cock whore kimmy 5 May 2020
Gary is a cross dressing sissy faggot, and his love of hot, thick, juicy, stud cock has turned him into the biggest little faggot sissy whore! He’s not happy until he’s left cock drunk, with his face covered in cum, and his little asshole is sore and gaping! What a little slut!
Caesars Bitch (ch. 2)
By Mikal 29 Apr 2020
This is a new installment of Caesars Bitch. In this tale Caesar has been with Jay jay for a time and is starting off on his first romance and is cementing his relationship. Yes there is abusive language but we are all grown ups so if you can't handle it move on.
Caesars Bitch
By Mikal 24 Apr 2020
Caesars Bitch is combination of a Cross Dressing & Sissy and First timer story. While I normally tell a story from the bottoms prospective I'm trying to expand my creative horizons and telling a good portion of this kinky tale from the Top Caesars prospective. it is also my sincere hope that you enjoy this tale and tell me what you think in the comments box.
Sweet Chrissi
By Mikal 19 Apr 2020
A short story about a fem boy.
Living my dream (ch. 2)
By SissyBoi 16 Apr 2020
Cute 18 yo femboy crossdresser meets a real man who gives his little boypussy a proper stretching and makes him his bitch
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Sweet Chrissi (ch. 4)
By Mikal 8 Apr 2020
While this story fits in the Crossdressing/Sissy catigory it is also a BDSM story. In Sweet Crhissi Chapter 4 Naughty Sissy's get Punished Chrissi is caught in bed with another man by his boyfriend Steve and there is Hell to pay.
Sacked Quarterback
By Cracker 7 Apr 2020
A macho star quarterback goes from a chick fucker to a cross dressing chick-with-a-dick who gets fucked.
Sissy Transformation
By Mikal 5 Apr 2020
Hi everyone I'm sure many of you are at home board and horny right now. Well I hope I can help relieve some of you with this story about a closeted sissy who meets a mistress that helps him find his true sissy self after he gets in debt to her.
Fighter Pilot's Pussy
By Clark Wayne 4 Apr 2020
Bi fighter pilot comes home to find his fighter pilot fuck-buddy waiting for him in sexy lingerie.
The end of a perfect night out as a sexy woman
By Bob Long 1 Mar 2020
This was the last but ultimately the best part of evening when my girlfriend took me out to a gay club, dressed as a woman just to test the water and to assure me that I not only very passable but also pretty damn hot. I got way much more than I imagined
Sweet Chrissi (ch. 3)
By Mikal 19 Feb 2020
Bored and in need of some dick Chrissi gets a surprise visit from a fellow sissy boy friend Daisy and it leads to a three way.
Broken
By Clark Wayne 17 Feb 2020
Straight man is attracted to an alpha. He becomes the alpha's toy. He tries to rebel but his new Alpha has decided to fix his attitude and humiliate him. If the closeted straight guy wants to get fucked, he'll have to wear some panties to show his devotion.
Before she turned me out
By Bob Long 10 Feb 2020
My girlfriend who fostered my obsession with crossdressing and living as a woman, trained and made me into one hell of a beautiful woman who eventually sucked a mans cock and loved it
How I got started (ch. 3)
By Bob Long 5 Feb 2020
Our continuing story of the greatest time of my life exploring and fulfilling my deep seated desire to be a woman through crossdressing and learning about my sexuality with the best teacher in the world my mom
How I got started (ch. 2)
By Bob Long 4 Feb 2020
This is a continuation of my glorious introduction to crossdressing and sex
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The Skin of Things (ch. 16)
By Chris Lewis Gibson 4 Feb 2020
He could still feel Ezekiel's mouth on his, and on his neck. He could still feel Ezekiel's chest and stomach against his back, Ezekiel in him, and through him, his penis, swelling and pumping in his mouth, the warm touch of the palm of his hand.
Condo for Sale
By Habu 3 Feb 2020
Sex helps sell expensive San Francisco condos.
My First time with a man
By Bob Long 2 Feb 2020
An encounter that just happened after years of repression
Parking lot blowjob
By Bob Long 1 Feb 2020
This is the story of how my ex girlfriend, made it her mission to get me to suck a guys cock
How I got started
By Bob Long 30 Jan 2020
This is how I began my life as a crossdresser, encouraged by my mother who lovingly guided me and embraced my desires to dress as a women
The Art of the Sissygasm
By cock whore kimmy 26 Jan 2020
Little CD fuckdoll has his first sissygasm and his life changed forever!
Sweet Chrissi (ch. 2)
By Mikal 22 Jan 2020
A new tale about the continuing adventures of Chrissi.
Caught crossdressing
By SandyCD 6 Jan 2020
Caught by daughter with me dressed as woman
Big Sissy
By Nils Huim 28 Dec 2019
A gay sissy bottom receives a surprise birthday gift
Amateur Crossdressing Prostitute
By Kristen Kross 23 Dec 2019
crossdresser's first time prostituting first timer
A Sissy’s Dream Comes True! Again and again!!
By FishnetSissy 21 Dec 2019
2 blonde bimbos help a little sissy faggot become the girl he always wanted to be and Introduce him to a man who knows just what to do with a special girl like this!
My New Apartment Manager
By Kristen Kross 21 Dec 2019
cd sissy meets her apartment manager
Starbucks
By Nils Huim 16 Dec 2019
Two ex-cons have anal & oral sex and then plot (?) a robbery
Living my dream
By SissyBoi 9 Dec 2019
A true story about me finally giving in to my deepest desire to become a cum addicted slut that loves being fucked and used as a toy, worships huge cocks and eats cum for breakfast.
Un-Expected Threesome
By Kristen Kross 7 Dec 2019
CD, girl, and a stranger meet in a motel room