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.

A Sissy Life

By Faedirk 7 Jul 2020

Cat-sitting for your neighbors becomes alot more exciting when you stumble upon their wardrobe collection.

9.1 (120) 27045 14 Min Comments

The Alley Way Short Story

By Luke Holton 17 Jun 2020

I’m walking alone coming back from the beach at night. Someone dressed in all black jumps out from one of the alley ways, stripping me and tying my body up. Read to find out what happens next

7.1 (22) 1612 2 Min Comments

I love My Dirty Daddy (ch. 2)

By Mikal 9 Jun 2020

Lola's Dirty Daddy Eric decides to give a lecture about sissy's to novice doms and share his little sissy with them.

9.0 (19) 4827 7 Min Comments

I love My Dirty Daddy

By Mikal 31 May 2020

BDSM ain't just just a bunch of gay bikers whips, chains, leather, and doms called Master or Mistress. BDSM is open to all sorts including cross dressers and sissies. I love My Dirty Daddy is about a sissies devotion to her dom who has a thing for letting other guys ball her.

8.5 (22) 7190 6 Min Comments

Turn About is Fair Play

By Mikal 30 May 2020

Turn About is Fair Play is a Caesars Bitch Sweet Chrissi cross over both are Detroiters and Jay Jay is mentioned in my 1st Sweet Chrissi as JJ. Anyway Caesar takes his cross dressing sissy boyfriend Jay Jay out they meet Chrissi and things get real naughty.

8.0 (5) 570 6 Min Comments

Sweet Chrissi (ch. 5)

By Mikal 29 May 2020

Dear Rears I really struggled with the decision to allow the Pandemic to be an element in my story. But I am writing a story about a cute sissy that lives in Detroit which has been impacted heavily and so I included it.

9.2 (11) 2492 3 Min Comments

my life (ch. 14)

By bijim 25 May 2020

agreeing for a second week of training

9.4 (14) 2446 6 Min Comments

my life (ch. 13)

By bijim 21 May 2020

our guest awake and I get morning wood and more

9.4 (15) 1154 6 Min Comments

Bi-Curious Boy's First Time

By Bi-Bottom B 15 May 2020

Story of my first time with a man.

7.7 (47) 13059 2 Min Comments

Crossdressing faggot meets a brutish construction worker

By Alex Walker 8 May 2020

A crossdressing fag makes a mistake that catches the attention of a burly construction worker and is invited over for some fun.

9.1 (76) 14059 6 Min Comments

Nocternal Eminations

By Mikal 7 May 2020

A story about being abducted and fucked by demons.

8.1 (14) 2773 9 Min Comments

I Love Being a Faggot

By cock whore kimmy 5 May 2020

Gary is a cross dressing sissy faggot, and his love of hot, thick, juicy, stud cock has turned him into the biggest little faggot sissy whore! He’s not happy until he’s left cock drunk, with his face covered in cum, and his little asshole is sore and gaping! What a little slut!

7.6 (22) 8786 7 Min Comments

Caesars Bitch (ch. 2)

By Mikal 29 Apr 2020

This is a new installment of Caesars Bitch. In this tale Caesar has been with Jay jay for a time and is starting off on his first romance and is cementing his relationship. Yes there is abusive language but we are all grown ups so if you can't handle it move on.

8.8 (17) 2902 6 Min Comments

Sweet Chrissi

By Mikal 19 Apr 2020

A short story about a fem boy.

8.8 (46) 4773 8 Min Comments

Living my dream (ch. 2)

By SissyBoi 16 Apr 2020

Cute 18 yo femboy crossdresser meets a real man who gives his little boypussy a proper stretching and makes him his bitch

8.8 (35) 9437 9 Min Comments

Sweet Chrissi (ch. 4)

By Mikal 8 Apr 2020

While this story fits in the Crossdressing/Sissy catigory it is also a BDSM story. In Sweet Crhissi Chapter 4 Naughty Sissy's get Punished Chrissi is caught in bed with another man by his boyfriend Steve and there is Hell to pay.

9.3 (8) 1367 6 Min Comments

Sissy Transformation

By Mikal 5 Apr 2020

Hi everyone I'm sure many of you are at home board and horny right now. Well I hope I can help relieve some of you with this story about a closeted sissy who meets a mistress that helps him find his true sissy self after he gets in debt to her.

8.3 (21) 7311 4 Min Comments

Sweet Chrissi (ch. 3)

By Mikal 19 Feb 2020

Bored and in need of some dick Chrissi gets a surprise visit from a fellow sissy boy friend Daisy and it leads to a three way.

8.2 (13) 1073 7 Min Comments

The Art of the Sissygasm

By cock whore kimmy 26 Jan 2020

Little CD fuckdoll has his first sissygasm and his life changed forever!

8.5 (49) 10751 3 Min Comments

Caught crossdressing

By SandyCD 6 Jan 2020

Caught by daughter with me dressed as woman

8.7 (85) 15456 12 Min Comments

Big Sissy

By Nils Huim 28 Dec 2019

A gay sissy bottom receives a surprise birthday gift

7.8 (16) 10903 10 Min Comments

A Sissy’s Dream Comes True! Again and again!!

By FishnetSissy 21 Dec 2019

2 blonde bimbos help a little sissy faggot become the girl he always wanted to be and Introduce him to a man who knows just what to do with a special girl like this!

7.8 (72) 34783 29 Min Comments

Starbucks

By Nils Huim 16 Dec 2019

Two ex-cons have anal & oral sex and then plot (?) a robbery

7.7 (21) 1779 10 Min Comments

Un-Expected Threesome

By Kristen Kross 7 Dec 2019

CD, girl, and a stranger meet in a motel room

8.7 (16) 2934 25 Min Comments

Met Mistress on grindr (ch. 2)

By zeenatcd 14 Sep 2019

My mistress made me her slave and gang banged me with her friend Domino,Alisa and Mariana.

7.8 (11) 4570 6 Min Comments

Girly

By bootlicker 22 Apr 2019

A small, weak, submissive man is feminized and abused by a trio of dominant perverts intent on transforming him into their sissy slave gurl.

8.6 (52) 33474 66 Min Comments

First me then my wife become a black guys bitch (ch. 2)

By Shy Stuart 10 Feb 2019

I bottle out of going into Carlton house and he's not happy. However, a week or so later while in a drunken stupor I give Carlton my address and invite him around to fuck me.

7.7 (86) 15268 4 Min Comments

Met Mistress on grindr

By zeenatcd 21 Jan 2019

This story about how I met mistress who enjoyed me and did BDSM on me.

7.9 (29) 6693 6 Min Comments

Getting dominated by an 9 inch cock

By Sissy Bitch 27 Dec 2018

Got dominated by a 9 inch cock while i was traveling

6.4 (81) 18222 2 Min Comments

How i became a bitch addicted for cock

By Sissy Bitch 23 Dec 2018

My history on how i became a little bitch that can not live without cock.

7.3 (97) 21179 4 Min Comments

Boy to College Girl

By Sissy Scarlet 29 Nov 2018

Charles has battled against his feminine features all his life. It takes a single experience with a dominant, alpha high school jock in the locker room to make him know his place in the world. ! ARCS Needed !

8.6 (88) 29919 23 Min Comments

First me then my wife become a black guys bitch

By Shy Stuart 21 Jul 2018

A newly married young man is lured into becoming a black guys bitch but does he have the nerve to go through with it?

7.7 (123) 22970 6 Min Comments

Sleazy Landlord

By Sissy Scarlet 12 Jun 2018

Jesse has been spending too much of his money on his... hobby. Now rent is due, what ever will he do? :)

7.7 (65) 12030 3 Min Comments

Singapore to Dubai unexpected journey (ch. 3)

By zeenatcd 12 Jun 2018

Razak showed me the heaven during sex and i became his slave.

9.2 (17) 3990 6 Min Comments

Boy to Bride (Feminization Novella)

By Sissy Scarlet 8 Jun 2018

Adam MacDonald secret life of crossdressing has always been both the escape and high of his life. A mysterious package with no sender address arrives one day, and inside it contains: a dress and more!

6.2 (82) 28233 7 Min Comments