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.
Gay Crossdressing Stories
GayDemon's gay porn library: in this story category you can find erotic stories with crossdressers and crossdressings.
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.
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
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.
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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.
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.
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.
Big black sissy Crack whore
By Big Black sissy 9 Jan 2022
My life that i want
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?
Santa Rosa Slut
By bootlicker 27 Dec 2021
A young drifter in Palm Springs is taken in and trained as a sissy, a slut, a slave, and a boi-whore by two older men and their friends.
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.
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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.
Park Slut (ch. 3)
By Alleykat 30 Nov 2021
Turned into the park cocksucker by a fat old man
Park Slut (ch. 3)
By Alleykat 23 Nov 2021
I would go to the park at night letting guys blow me until the fat old man turned me into the cocksucking cumloving slut at the park and at my mom's house.
Now I'm a crossdressing Domme?
By BillyBoy 20 Nov 2021
A shy, submissive guy hits me up to dress like his wife and Domme him. I actually liked it more than I thought I would!
How this straight guy became a sissy bottom
By Somewhat Straight 17 Nov 2021
It took while, but my transformation is complete
Doctors are human too
By BillyBoy 11 Nov 2021
I forgot and wore some panties to my check-up. The doc was surprised. But he responded differently than I expected.
In a short span I became a sissy boy trap (ch. 2)
By Desertbiguy 10 Nov 2021
I had spent all of my time getting indoctrinated in gay sex by Tom G. I forgot about my first man to pop my anal cherry Mark.