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.

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.

8.4 (42) 12746 21 Min Comments

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.

9.0 (21) 6177 38 Min Comments

Step-Sissy (ch. 2)

By BabyBoiPussy 31 Aug 2022

‘Let me feel your body spasm pussy boy.’ And that it did. He continued to fuck and gag me. He fucked me faster and faster with his big cock. The pain melted away at this point and I was just a moaning, gagging, slobbering mess. His body tensed up as he wrapped my body with his other arm and crushed my body against his.

8.6 (69) 10782 6 Min Comments

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.

8.7 (7) 1053 16 Min Comments

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.

8.4 (7) 818 22 Min Comments

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.

8.4 (7) 1507 13 Min Comments

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,

8.6 (22) 2399 15 Min Comments

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.

7.6 (7) 5985 7 Min Comments

Lifechanger

By Cirkle7 26 Jul 2022

I get fucked and like it!

8.5 (37) 6525 9 Min Comments

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.

8.2 (16) 2913 5 Min Comments

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.

8.1 (12) 1620 12 Min Comments

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 ..

8.8 (15) 2212 12 Min Comments

Becoming Javon’s Bitch

By cumpigslave 29 Jun 2022

How I became a sissy slut addicted to big black cock

7.8 (60) 13617 3 Min Comments

A journey of transformation

By Vikktor 14 Jun 2022

I finally found someone that could help me fulfill my desires.

8.9 (52) 10509 17 Min Comments

White Boy Turned

By lilboy 13 Jun 2022

White boy thinks he's gonna get lucky with hot black woman.

8.6 (90) 18014 4 Min Comments

Gone fishing (ch. 2)

By Gpasboi 12 Apr 2022

Part 2 - It had been almost 2 year's since my fishing trip with Jim & Gary. And even though I had gone on several trips to Jim's cabin , he had never even hinted that anything ever happened. Not a joke not a wink nothing. By this point I was pretty much thinking it was all just a dream.

8.9 (40) 4463 8 Min Comments

Sissy photo shoot peril

By BillyBoy 25 Mar 2022

The guy was a bad photographer and an even worse perv.

9.2 (22) 3912 8 Min Comments

Step-Sissy

By BabyBoiPussy 22 Mar 2022

From straight man, to the sissy whore of the family only used for other men's pleasure.

9.3 (137) 21546 9 Min Comments

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.

8.6 (71) 9141 7 Min Comments

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.

8.1 (7) 881 12 Min Comments

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.

8.0 (7) 733 10 Min Comments

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!

8.6 (17) 3563 8 Min Comments

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?

7.9 (23) 4924 4 Min Comments

Bondage games

By BillyBoy 4 Mar 2022

One of several kinky bondage games the boys like to play.

8.4 (40) 11702 5 Min Comments

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.

9.2 (11) 2998 67 Min Comments

Dad and me

By BillyBoy 24 Feb 2022

dad finds me in her room wearing her panties and bra. Oh fuck!

8.8 (87) 14344 3 Min Comments

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.

7.9 (27) 9623 10 Min Comments

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.

9.0 (70) 9752 11 Min Comments

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.

7.9 (17) 2932 9 Min Comments

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

9.7 (117) 2653 5 Min Comments

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.

9.6 (119) 1523 9 Min Comments

Wrong rest stop

By Alleykat 16 Jan 2022

Turned into a cocksucking cumloving slut

9.1 (71) 10369 7 Min Comments

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.

8.6 (40) 5719 4 Min Comments

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.

8.9 (70) 7657 4 Min Comments

Big black sissy Crack whore

By Big Black sissy 9 Jan 2022

My life that i want

7.9 (28) 15541 20 Min Comments