Step-Sissy
By BabyBoiPussy 22 Mar 2022
From straight man, to the sissy whore of the family only used for other men's pleasure.
Gay Sissy Stories
GayDemon's Stories: On this page you can find erotic fiction where you can read about men dressed and made into girls and sissification.
My summer transformation into a sissy
By Desertbiguy 21 Mar 2022
I turned 18 yo. I was always intrigued by what puberty did to my body. It was summertime parents worked 6 days a week. Leaving me to stay home and do mischievously things.
Gunpoint (ch. 3)
By Tom C 20 Mar 2022
“Gunpoint” is a story told in three parts of the abduction of a young trans woman, Lucy, and her foster siblings. The kidnapper’s boss has sex with Lucy, an inexperienced lover, and she develops feelings for him. Even so, Lucy realizes she must act to help her siblings.
Gunpoint (ch. 2)
By Tom C 19 Mar 2022
“Gunpoint” is a story told in three parts of the abduction of a young trans woman, Lucy, and her foster siblings. The kidnapper’s boss has sex with Lucy, an inexperienced lover, and she develops feelings for him. Even so, Lucy realizes she must act to help her siblings.
The Couple
By BillyBoy 9 Mar 2022
Dave and his wife are swingers of sorts. They like to bring sissy guys in for her strap-on dildo fuck while he throat fucks them. She likes to watch him suck off other guys. She likes to watch him get fucked, too. It was a crazy weekend!
Internet site gone wrong, or not.
By BillyBoy 5 Mar 2022
Someone recognized me from the post in GayDemon! Maybe I was hoping that would happen?
Bondage games
By BillyBoy 4 Mar 2022
One of several kinky bondage games the boys like to play.
Twinkle little Slut (ch. 3)
By westside 2 Mar 2022
I moaned running my hands over my body thinking of all the men I had been with over the weekend and started stroking myself to the verge of orgasm, but I stopped myself because I wanted to share my orgasm with a man any man.
Dad and me
By BillyBoy 24 Feb 2022
dad finds me in her room wearing her panties and bra. Oh fuck!
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.
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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.
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.
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.
Wrong rest stop
By Alleykat 16 Jan 2022
Turned into a cocksucking cumloving slut
Bondage dreams come true
By BillyBoy 13 Jan 2022
My gay lover left me but not before he turned me over to a gay Dom Master. I guess I should have been more careful of what I asked for.
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.
Big black sissy Crack whore
By Big Black sissy 9 Jan 2022
My life that i want
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
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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!
Still cruising at the mall
By Alleykat 8 Dec 2021
After sucking older guys in the restroom at the mall. I let this other guy pick me up and take me to his van.
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
Chis(topher) & Chris(tina) (ch. 2)
By djfmonkey 23 Nov 2021
Chapter 2. - Chris and I meet the grandparents
Chis(topher) & Chris(tina)
By djfmonkey 22 Nov 2021
I met and fell for a crossdresser, explore chapter 1 introducing us, and future chapters meeting family and friends
How this straight guy became a sissy bottom
By Somewhat Straight 17 Nov 2021
It took while, but my transformation is complete
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.
In a short span I became a sissy boy trap
By Desertbiguy 8 Nov 2021
Halloween changed my life to being a sissy boy trap. I dressed up to be a girl at a big jr high party. After that I was addicted to cock. Discovered craigslist. Put and ad as a sissy boy dressed up as a girl. Met Tom G older guy. Both times I was fucked doggy style. Introduced me to gay sex. My butt is a true boi pussy.
Crossdressing
By BillyBoy 2 Nov 2021
Envious of the girls always getting to wear those cute little bras and panties.
Halloween is a great time to express sexual feelings
By Desertbiguy 2 Nov 2021
I decided to dress up as a girl for halloween. There was a big party going on for us jr high kids. And looked good. Maybe to good. Mark was a good looking guy. Something happened at party. He became attracted to me.
Becoming the Fishing Camp Princess
By Dickguy4U2 31 Oct 2021
While well over the legal age of sexual consent, my looks represented a much different picture. Broght up by a single parent overbearing mother, my being raised was far from the normal channels of a lone single male son.With mom making dresses and me the perfect slender size to model her creations, I guess you could say that the soft silk and lace never failed to stimulate me in a secret sexy way
Bunny and Daddy (ch. 3)
By satyrDaddy 22 Oct 2021
Bunny webcams with Daddy...and more