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.

Daniel Effeminate College Student

By Colourfast 30 Nov 2020

A story about effeminate college freshmen and their encounters with mature gentlemen.. .college age very cute twinks with hot scenes

8.3 (25) 5046 18 Min Comments

I Would Never Kiss a Guy (ch. 4)

By GabbyGurl 26 Nov 2020

Gabby makes a major lifestyle decision and visits Nate.

9.5 (33) 4589 9 Min Comments

The truck driver

By bijim 4 Nov 2020

a truck driver gets flagged for a service and gets his life turned upside down while waiting

8.6 (96) 10515 5 Min Comments

I love My Dirty Daddy (ch. 4)

By Mikal 17 Aug 2020

This is my 4th installment in I Love My Dirty Daddy. While I am sure you may all enjoy Lolas Daddy dominating her and having her fuck other guys to get his this is a story about Lola who like her Daddy is polyamorous and enjoys having her own adventures. I love the input of other readers.

8.8 (8) 4883 7 Min Comments

I love My Dirty Daddy (ch. 3)

By Mikal 29 Jul 2020

Well it's been a while since I have had a chance to write but I'm back to it. Lola and her Daddy decide to go out for their 3rd anniversary and have a bit of fun with their friend which end with Lola getting a tramp stamp and an ass fucking from a guy with a titanic cock.

8.8 (14) 3306 7 Min Comments

The Winning Bid

By Nils Huim 23 Jul 2020

At auction a male bidder wins the services of a man modeling sissy panties

8.0 (19) 1895 6 Min Comments

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) 27125 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) 1621 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) 4901 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) 7299 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) 573 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) 2501 3 Min Comments

my life (ch. 14)

By bijim 25 May 2020

agreeing for a second week of training

9.4 (14) 2467 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) 1161 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) 13114 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) 14156 6 Min Comments

Nocternal Eminations

By Mikal 7 May 2020

A story about being abducted and fucked by demons.

8.1 (14) 2808 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) 8991 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) 2914 6 Min Comments

Sweet Chrissi

By Mikal 19 Apr 2020

A short story about a fem boy.

8.8 (46) 4791 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 (36) 9532 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) 1379 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) 7408 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) 1083 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) 10825 3 Min Comments

Caught crossdressing

By SandyCD 6 Jan 2020

Caught by daughter with me dressed as woman

8.7 (86) 15691 12 Min Comments

Big Sissy

By Nils Huim 28 Dec 2019

A gay sissy bottom receives a surprise birthday gift

7.8 (16) 10991 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) 34959 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) 1796 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) 2953 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) 4607 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) 34135 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 (87) 15351 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) 6769 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) 18327 2 Min Comments