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.

The Cunting of Lucas (Lucy) (ch. 14)

By GWSHomo 8 Jun 2026

Lucy's first two days without Daddy there to guide and use her turn out to be pretty interesting.

7.6 (9) 623 29 Min Comments

The Cunting of Lucas (Lucy) (ch. 13)

By GWSHomo 2 Jun 2026

Lucy is taken around the town and meets some more interesting men. As well as learns about what her life away from Daddy's house will look like.

7.3 (5) 899 35 Min Comments

Stepbro Catches Secret Slut (ch. 3)

By ANSH 1 Jun 2026

I pulled out. Josh made a sound—half gasp, half whimper—and his hole clenched around nothing, already missing the fullness. A thick string of pre-cum and lube connected my tip to his entrance before it snapped and dripped onto the floorboards.

8.0 (13) 1248 6 Min Comments

Stepbro Catches Secret Slut (ch. 2)

By ANSH 31 May 2026

His mouth was hotter than I expected. Wet and greedy and making these desperate little gulping sounds as I pushed deeper, the head of my lund dragging across his tongue like he'd been starving for it.

8.8 (14) 1290 7 Min Comments

Stepbro Catches Secret Slut

By ANSH 30 May 2026

Stepbro finds Josh's hidden lingerie and sex toys, snoops his phone for pegging erotica, then confronts him with chastity devices and filthy breeding.

8.4 (20) 2606 8 Min Comments

Walked into the wrong room

By BillyBoy 23 May 2026

Invited to visit him and a friend for drinks. I'd never been there before. I barely knew him. Inside I discover a scene I can't get out of my mind. He has his buddy's hands tied up to the ceiling, he is gagged and naked. I stayed longer than I should.

7.9 (23) 1531 3 Min Comments

Midnight Saree

By Priyanka 12 May 2026

A straight cuckold son, turned into a sissy slut of old drunken man

7.3 (11) 2892 5 Min Comments

The Cunting of Lucas (Lucy) (ch. 8)

By GWSHomo 1 May 2026

A short intermission before the next big day in Lucy's new life as Daddy's girl

8.3 (28) 2354 11 Min Comments

Abusive Sissification (ch. 5)

By Kavya sissy 22 Apr 2026

It’s chapter 5 and I’m being fucked abused and tortured in the middle of the street, the abuse continues…

7.6 (14) 4457 7 Min Comments

Chaddy Sparkles

By CdJenny 12 Apr 2026

Ethan, a bullied nerd, transforms Chad, his high school tormentor, into “Chaddy Sparkles,” a submissive bimbo, using the Persona Shifter.

8.0 (10) 2999 34 Min Comments

Riley’s Power

By CdJenny 7 Apr 2026

Riley is the victim of a college prank which leads to them stumbling apon a mysterious shop ran buy a witch who gives Riley the power of revenge

7.4 (15) 2373 37 Min Comments

Seducing my straight homophobic son (ch. 2)

By Chloe 4 Apr 2026

Stephen and his straight son are ready for round 2

9.4 (49) 6007 25 Min Comments

Seducing my straight homophobic son

By Chloe 19 Mar 2026

A bisexual father seduce his straight son

9.2 (108) 15084 36 Min Comments

The Cunting of Lucas (Lucy) (ch. 5)

By GWSHomo 18 Mar 2026

Lucy's first day with her newly formed cunt comes to a close. But will tomorrow bring new challenges?

8.3 (23) 3765 8 Min Comments

The Bimbo Maker (2025 Remix)

By CdJenny 17 Mar 2026

Chris, a straight college student, takes a bet with his friend Rick, who claims his cock has a supernatural power over men. If Chris can resist its allure for 24 hours, he wins $500. But as the hours pass, Chris undergoes a shocking transformation, his body and mind reshaping into a perfect bimbo, consumed by an uncontrollable obsession with Rick’s

8.8 (33) 3841 23 Min Comments

The Cunting of Lucas (Lucy) (ch. 4)

By GWSHomo 17 Mar 2026

He got up and pulled me off the bed. Leading me upstairs where he said he had lunch waiting. We both sat at the table. Me still feeling the aftermath of his fucking. He tossed me a small pillow. Which seemed to help a little.

9.1 (33) 4159 11 Min Comments

The Cunting of Lucas (Lucy) (ch. 3)

By GWSHomo 16 Mar 2026

It is time fir Lucy to have her new cunt molded and shaped into the perfect hole to fuck.

8.7 (33) 4349 13 Min Comments

The Cunting of Lucas (Lucy) (ch. 2)

By GWSHomo 14 Mar 2026

When Lucy tries to escape. Daddy puts her back in her place. Soon, the faggot learns she will start loving her new life.

8.9 (51) 6223 13 Min Comments

The Cunting of Lucas (Lucy)

By GWSHomo 13 Mar 2026

When Lucas moves to a new town. He never suspected that his manhood and grip on his sexuality would be raped away. And that he would LOVE it!

9.0 (63) 8405 21 Min Comments

Blackmail on Dad

By Chloe 4 Mar 2026

Peter, Leo's father suffers from gambling addictions... His son offers him a solution to help him...

9.3 (31) 4497 16 Min Comments

Unexpected first Gay sexual experience (ch. 10)

By Loverboy 1 Mar 2026

After Curtis going without sex with his boyfriend for over a year and me not having sex with my girlfriend or anybody else for over 4 months, Curtis and I decided to get together for a random one-time gay sexual hookup with each other to make up for our lack of sexual activity at home by satisfying each other sexually.

9.2 (13) 507 57 Min Comments

Being owned (ch. 6)

By Chocolate_Boo 19 Feb 2026

Taking control of his/her whole being

8.9 (19) 3070 4 Min Comments

Being owned (ch. 5)

By Chocolate_Boo 16 Feb 2026

Daddy didn’t even let me stand. He grabbed my wig, dragged me across the hardwood on my knees, latex catsuit squeaking with every frantic inch.

8.6 (19) 2625 4 Min Comments

The Guy With The Long Hair

By Mark Blazer 16 Feb 2026

Soccer stud falls under the spell of a femboy sissy slut.

9.3 (60) 4680 10 Min Comments

Being owned (ch. 4)

By Chocolate_Boo 15 Feb 2026

Sissy being tested beyond her ability

9.1 (26) 3093 4 Min Comments

Being owned (ch. 3)

By Chocolate_Boo 12 Feb 2026

Free use of a sissy and forcing drugs

8.6 (29) 5129 4 Min Comments

Being owned (ch. 2)

By Chocolate_Boo 11 Feb 2026

Another encounter with dominant male

9.1 (24) 4221 4 Min Comments

Being owned

By Chocolate_Boo 10 Feb 2026

Sissy being owned for the first time

8.2 (39) 6609 4 Min Comments

Unexpected first Gay sexual experience (ch. 6)

By Loverboy 29 Jan 2026

I decided to explore adult gay sexual hookup websites, specifically Adult Friend Finder, which catered to a diverse range of sexual interests and sexual preferences after bad luck in meeting gay men on man for man gay chatrooms for sex, and my bad luck in meeting gay men for sexual connections in a gay bar.

9.6 (21) 773 21 Min Comments

Sometimes, Things Just Happen

By DirtySlot 26 Jan 2026

This is Part 1 of a fictionally inspired encounter i had when i was a few years younger. 3 Daddies, me and the lead up to their Cabin and the weekend i had with them.

8.0 (18) 3521 32 Min Comments

The Experiment (ch. 3)

By GodE 19 Jan 2026

Phase Three: The Mind's Surrender

6.0 (14) 5371 2 Min Comments

My anonymous meet turns out to be not so anonymous

By Filthyslagbag 16 Jan 2026

Anonymous meet turns out not so anonymous as straight acting discreet guys who know each other accidentally meet up for a filthy meeting

7.0 (39) 4224 3 Min Comments

Tyler is a dirty cum piggy

By DirtyDumbSissy 16 Dec 2025

Tyler is degraded beyond coming back by 6 black gods.. he has gone beyond being a piggy useless meth addict to something without descriptions

8.2 (50) 6776 3 Min Comments

Payback is a useless community bitch

By DirtyDumbSissy 14 Dec 2025

Alex got his payback like the bitch he was meant to be, a useless shit bitch for the homeless community

8.4 (23) 4278 11 Min Comments

Jamie is a useless sissy

By DirtyDumbSissy 13 Dec 2025

Jamie is a toilet slut meth addict...

8.6 (29) 5555 6 Min Comments