Be careful what you wish for
By BillyBoy 1 Mar 2022
I let him dress me like a schoolgirl, tied me up and fuck me.
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.
Dressed to Thrill At The Club
By lickme 28 Feb 2022
Getting slutty and hot a gay club for the first time
College Crush Dominates Me (ch. 4)
By RR 27 Feb 2022
Ryan buys me sexy underwear and intoxicates me with his masculine scent before sucking my little nub into the most glorious orgasm I had experienced.
First Date Dressed To Kill
By lickme 24 Feb 2022
Dressed to Kill! First date with stranger and ready for seduction!
Oliver's Story
By Caliban 23 Feb 2022
A transgender love story... (updated version)
Cock Dreams Come True
By lickme 21 Feb 2022
Hetero guy with kinky man to man fantasies
Misadventures of a sissy boy
By Desertbiguy 21 Feb 2022
I turned 18 yo and graduated out of high school. I decided to move out on my own without a roommate. I got great job to pay bills.
Picking up a Stray
By Disbtm 8 Feb 2022
Driving long distances can be lonely. Here's a tale of a driver picking up a little friend on a dark highway and teaching him how to be a good cock sucking sissy. Gas, Grass or Ass, nobody rides for free.
Trying on a few new things
By BillyBoy 4 Feb 2022
Another Halloween is here! Maybe this year I'll catch my first man!
Used like a slut
By Punkboi18 28 Jan 2022
I became a sissy slut in high school and I didn't mind the guys using me for sex. After graduating a bully named Troy decided he wanted my ass. I knew I had to put out.
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American cross dresser in Europe
By WLASteve 26 Jan 2022
A 2006 solo trip to European is a fulfillment of a lifelong dream
crossdressing was a hobby
By BillyBoy 22 Jan 2022
I played for a long time in her clothes. I even took some pictures of me dressed up pretty. Now I have men calling me all the time. What should I do? Does dressing make me gay? I do dream of sucking a big fat cock a lot. Maybe I'll answer one of the guys.
Caught in hers and compromised
By BillyBoy 21 Jan 2022
Jim noticed I was wearing nylons and a bra. He used my embarrassment to his advantage.
Chis(topher) & Chris(tina) (ch. 5)
By djfmonkey 20 Jan 2022
What happens after the corporate holiday party and events leading up to an unusually interesting Brunch with Chris' Boss
Chis(topher) & Chris(tina) (ch. 4)
By djfmonkey 19 Jan 2022
After visiting my mom and dad, Chris and I get invited to his very conservative corporate Holiday Party, how can he attend and not bring me.
Tell me you love me
By BillyBoy 19 Jan 2022
He was great. He followed all my requests. A dream come true.
Crossdresser makes homeless man happy
By Paulacd 17 Jan 2022
I had gotten dressed very sexy and slutty one night being completely hairless permanently except for my eyebrows eyelashes and long hair on my head.
Becoming a sissy crossdresser for him
By BillyBoy 15 Jan 2022
I started wearing moms underclothes when I was younger. They were always laying around in her bedroom and in the laundry. But later I discovered he was leaving them around for me to find. He was tricking me into becoming a sissy crossdresser for him.
Heather (ch. 5)
By Heather_xd 11 Jan 2022
Apologies for delay in the next chapter of Heather - The last chapter finished with my live in lover finding me being spanked by my coloured friend after he had fucked me and the cum was dripping from my pussy. He packed and left straight away.
Neighborhood faggot boy (ch. 2)
By Alleykat 11 Jan 2022
Every old pervert knows where I live and now I'm the neighborhood cocksucking cumloving slut
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Prom going wrong
By BillyBoy 11 Jan 2022
I dressed like a girl for prom. My friend Jeff and I didn't have proper girl dates. It was sort of a joke and a few of the other boys were doing it. And Jeff's dad seemed to like me a lot.
The Struggles of Becoming a Woman
By Getoutofmymind 11 Jan 2022
When becoming a woman things, in the beginning, are extremely difficult! Chapter 1.
Blackmail
By Victor 10 Jan 2022
Decker has found out his nemesis, Fitch, another closeted jock, has been hooking up with a male escort/cam boy. Now he intends to get what he wants from the gorgeous jock by blackmailing him.
I'm his bound and gagged girlfriend
By BillyBoy 6 Jan 2022
She told her friends I wanted to wear her underwear and be tied up when we had sex. It was a weak moment for me. I shouldn't have asked her. I was young and didn't know any better. She didn't appreciate my wishes at all. That was it for her, and most any other chance I may have had with a girl. But, she handed me off to someone who did appreciate my fantasy. For better or worse!
After Halloween
By BillyBoy 30 Dec 2021
I wore a girl's dress as a joke to a Halloween party. It was all in fun. Wives and girlfriends were there. But after that, I got a few uncomfortable calls and texts from a few of the men who saw me.
bondage blowjob
By BillyBoy 28 Dec 2021
I woke up in his bedroom, wearing his wife's wedding lingerie. I'm on my knees with his cock in my face. What now?
First Time Adult Book Store Wearing Panties
By CuriousInPanties63 24 Dec 2021
The first time I wore panties to an adult book store at 19 years old and an older sexy daddy man in his 60's had some fun with me in my panties.
Neighborhood faggot boy
By Alleykat 24 Dec 2021
My address was on the bathroom stall.. Cocksucking cumloving pretty boy cruise by after 9pm weekends
Cross dresser.. Twink.. Tranny?
By djfmonkey 22 Dec 2021
My straight buddy and I visit a gay bar, where we discover our own inner selves, and the truth about each other
Shower Power
By BillyBoy 22 Dec 2021
'Daddy' shaved me in the shower. While the water was pouring over us, he put me in a matching set of rubbery vintage Playtex bra and open bottom girdle panties.
Chis(topher) & Chris(tina) (ch. 3)
By djfmonkey 12 Dec 2021
Chris and I finally visit my parents for the holidays in my overly homophobic upstate New York Hometown
Secret Sissy
By BillyBoy 10 Dec 2021
I've been in the closet all my life. Finally, I have a chance to try out being a sissy girl for a real man
Dreams and Frustration
By BillyBoy 9 Dec 2021
Every day I awake from a dream of being used as a girl whore. I can't stop it. I'm in trouble!
My secret dreams
By BillyBoy 7 Dec 2021
The gay date I'd love to experience. I've had a few gay experiences, but someday a man will make me his little bitch. I'd love that!
Halloween party
By BillyBoy 2 Dec 2021
I finally let him seduce me. I agree to meet him. He has been flirting and making promises. Then at the last minute, he tells me I'm going to dress like a woman tonight.