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.

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) 2889 6 Min Comments

Sweet Chrissi

By Mikal 19 Apr 2020

A short story about a fem boy.

8.8 (46) 4743 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) 9322 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) 1345 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) 7157 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) 1055 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) 10624 3 Min Comments

Caught crossdressing

By SandyCD 6 Jan 2020

Caught by daughter with me dressed as woman

8.7 (84) 15101 12 Min Comments

Big Sissy

By Nils Huim 28 Dec 2019

A gay sissy bottom receives a surprise birthday gift

7.8 (16) 10794 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) 34465 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) 1760 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) 2900 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) 4497 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.

8.5 (47) 32529 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 (85) 15108 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 (28) 6542 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 (80) 18060 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 (96) 20984 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) 29696 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) 22667 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) 11915 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) 3944 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) 27882 7 Min Comments

Good Lumberjack, Bad Lumberjack

By Sissy Scarlet 26 May 2018

A foreign loser in his hometown, a boy works at a carnival where he is embarrassed by dehumanizing customers. A charming Alpha finds the boy in tears, comforts him, and the two end up starting a secret relation

7.3 (30) 3653 5 Min Comments

Chrissy's New Life

By sluttybttm4u 17 May 2018

Phillip/Chrissy has been seeking a loving life in the hands of a very loving man

5.5 (22) 5961 2 Min Comments

Abandoned Parking Lot (ch. 2)

By Sissy Scarlet 9 May 2018

After fighting with a drunk girlfriend, a boy is fed up with women. He decides to finally live out a fantasy he's had for years.

8.0 (94) 20932 2 Min Comments

Abandoned Parking Lot

By Sissy Scarlet 7 May 2018

After fighting with a drunk girlfriend, a boy is fed up with women. He decides to finally live out a fantasy he's had for years.

6.6 (68) 26765 3 Min Comments

Lap Dance For Rent Money

By Browncherrygurl 24 Dec 2017

Short for this month's rent money must perform for a disgusting old geezer.

7.5 (33) 8784 5 Min Comments

Gurl Story (ch. 2)

By Browncherrygurl 22 Dec 2017

During blackout in a small town motel, a sissy learns never to tease the wrong man

8.2 (34) 5841 16 Min Comments

Mr. Phillips's Loves My Body

By Browncherrygurl 21 Dec 2017

A trusted neighbor finally gets the opportunity to take advantage if a young crossdresser he has be watching through his window

8.7 (94) 11050 8 Min Comments

Gurl Story

By Browncherrygurl 19 Dec 2017

Crossdresser meets craigslist date at isolated dive bar and has a rough unexpected time

8.4 (39) 7122 16 Min Comments

Meeting 'Katie'

By acessez 3 Apr 2017

the fictional account of my first encounter with 'Katie' in amsterdam

7.7 (24) 2758 10 Min Comments

Rescued from pantyhose peril by officer Ron

By Zman350 29 Dec 2016

A straight married cop comes to the rescue of a cross dresser, and discovers a hidden desire

8.7 (77) 7587 9 Min Comments

The sissy within me The Transformation from boy to Daddies sissy

By Ed 27 Apr 2015

Justin is slowly transformed into a sissy by his new daddy

7.2 (124) 37758 6 Min Comments

While the cats away, I get to play

By mwmalone 4 Apr 2015

A fantasy of becoming a black mans sissy slut but hope it cums true someday

7.9 (46) 8534 14 Min Comments