My first dressing up
By Jennfair 21 Oct 2022
How I found out I really liked dressing as a girl. My mom was my inspiration. I became the fourth girl in the family.
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.
Thank you, Mister Townshend
By Okamaguy 10 Oct 2022
A family friend catches me in panties and heels, and I have to pay for his silence
My first time with a man
By Jennfair 6 Oct 2022
How I turned a sexy chat into super hot sex with a man for the first time.
I became a sex slave
By Viki 16 Sep 2022
This is a story of how my normal life changed and i became an obedient sissy for, my master.
The CC Society
By bootlicker 6 Sep 2022
The merging of two of my stories published on another site. Two feminized sissies are sold to dominant sadists who plan to use and abuse them for their pleasure.
Unforgettable summer (ch. 3)
By Viki 29 Aug 2022
Part 3 follow-up on "A normal relationship turned into a wild weekend orgy". The names and places of this story are not real.
Unforgettable summer (ch. 2)
By Viki 28 Aug 2022
Part 2 follow-up on "A normal relationship turned into a wild weekend orgy". The names and places of this story are not real.
Unforgettable summer
By Viki 27 Aug 2022
A 3 part follow-up on "A normal relationship turned into a wild weekend orgy", the next time we all got together for an amazing vacation. The names and places of this story are not real.
A normal relationship turned into a wild weekend orgy (ch. 2)
By Viki 25 Aug 2022
Continuation of the story "A Normal Relationship Turned Into A Wild Weekend Orgy" This is the events of the said weekend,
A normal relationship turned into a wild weekend orgy
By Viki 24 Aug 2022
When I was 19 I moved to the big city for university, this was my first time living alone. I considered myself a normal man, even had a girlfriend for a bit, but I always knew I wanted more. I have always been interested in men and wanted to sleep with one. I was also fascinated with sissies and liked women’s clothes. Now to the story..
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A unexpected turn of events
By Viki 20 Aug 2022
An unexpected surprise, that led to an interesting experience
Getting fucked by grinder date in hotel (ch. 2)
By zeenatcd 20 Aug 2022
After we met first time at hotel we started talking about fantasy of each other and started fulfill them. So this was his first fantasy.
Taken for the first time, but not the last
By Disbtm 9 Aug 2022
A young traveler's car breaks down and he finds himself tied down to a kitchentable, crying and loosing his anal virginity.
PrincessBoy Diaries
By BeefyFem 8 Aug 2022
Daddy has fun surprises in store for his boy princess as they mix business and pleasure in Palm Springs
What I Want
By Victor 1 Aug 2022
Tall, massively muscular Brodin is a no nonsense bottom with many fuck buddies. One night a married fuck buddy asks him to slip on a pair of panties. To Brodin's surprise, he likes it and so starts a new kink for the big, broad bodybuilder.
Lifechanger
By Cirkle7 26 Jul 2022
I get fucked and like it!
Bottom boy at antique store (ch. 3)
By cut 9 Jul 2022
Like a bitch
Sissie
By Mikal 9 Jul 2022
My name is Sissie it used to be Matt, but that name doesn’t fit. I just put up a sissy pride flag in my window. Mine has pink and white stripes with a modified phallus symbol that looks like a heart with a limp arrow jutting out of it.
The Rest Stop Digest - The Jill Jordan story (ch. 2)
By SkylarWinterLouis 2 Jul 2022
Although this is ch 4 , it is the 2nd part of the Jill Jordan story.
The Rest Stop Digest - The Jill Jordan story
By SkylarWinterLouis 1 Jul 2022
The Rest Stop Digest . This is one of many stories I have written through out the years. Most of these stories are real experiences. Some of these stories are about different people, but they are based on real event and told as close to a Accurate as possible. This is a true story but the names have been changed ..
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Becoming Javon’s Bitch
By cumpigslave 29 Jun 2022
How I became a sissy slut addicted to big black cock
A journey of transformation
By Vikktor 14 Jun 2022
I finally found someone that could help me fulfill my desires.
Cross dressing Cumslut
By SoooperFreakk 10 Jun 2022
CD Cumpdump and fun freak meet up
Summer of My Life
By Roxxi 1 Jun 2022
I Was thinking about Tony' s cock, and as I slid a black lace g string up to my hips and tucked my clit back.
Becoming Ms. Dee Praved
By Ms. Dee Praved 26 May 2022
I venture out to explore my sexuality, and meet a more experienced crossdresser and her friend. He takes us both and uses us well. This is a true story.
CEO
By Victor 24 May 2022
My hot DILF CEO is an alpha with a soft side when we're alone. The older muscle stud wants nothing more than my younger, muscular body to dominate him and make him my bitch.
Crossdresser Confessions
By Ms. Dee Praved 23 May 2022
The true story of one of my favorite guys from Craigslist. He was a horny young soldier just looking to come. Of course I eagerly offer my mouth and ass to him.
Let's Play Dress Up
By James Stone 21 May 2022
"If it's not a big deal, then you do it," I said. He shrugged and got up, going to the box. He dug around until he came up with another bra, a little nicer than the one I was holding, pink lace and pink satin. He held it up and then slipped his arms through the straps, holding it against his chest, over his shirt. He tried to reach around back to close it, but couldn't...
gay switch weekend with the twins
By BillyBoy 30 Apr 2022
this is a gay site, right? well, fuck me running. I got a good one!
New Bookstore Experience
By MontanaBiGuy 21 Apr 2022
A visit to a new bookstore turns into a very fun experience. Oral, anal
The Scoop
By Habu 18 Apr 2022
Garbage man or reporter? Assumptions can be misleading.
Forced cock lovers story
By fanny 2 Apr 2022
A story of a shy crossdresser guy gets forced by a hungry bear.
Fantasy's come true
By BillyBoy 31 Mar 2022
Finding Mr. Goodbar. Looking for the perfect man to fulfill my fantasies was a long, hard journey.
A Disturbing Desire
By Cirkle7 28 Mar 2022
A gang bang fantasy.
Sissy photo shoot peril
By BillyBoy 25 Mar 2022
The guy was a bad photographer and an even worse perv.