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.

Gone fishing

By Gpasboi 21 Jan 2021

He told me that he had put some clothes on my bed that I could wear for the night until my stuff had a chance to air out. When I walked in my room there on the bed was a white tshirt and a pair white silk panties with lace trim and I yell to Jim what the hell is this ?

8.4 (65) 13071 12 Min Comments

I Would Never Kiss a Guy (ch. 5)

By GabbyGurl 24 Dec 2020

Gabby makes a commitment to Nate.

9.6 (31) 2605 4 Min Comments

Daniel Effeminate College Student (ch. 14)

By Colourfast 14 Dec 2020

A series of stories about effeminate college twinks and their encounters with mature gentlemen

8.9 (6) 1267 22 Min Comments

Daniel Effeminate College Student (ch. 13)

By Colourfast 13 Dec 2020

A series of stories about effeminate college twinks and their encounters with mature gentlemen

8.2 (6) 1842 9 Min Comments

Tell Tales Of A Jock

By Labeautifull 13 Dec 2020

A college Quaterback is caught all dolled up in Ladies Langerie by his Roommate who happenes to be the Wide reciever of their Team.

8.9 (42) 4277 29 Min Comments

The truck driver (ch. 2)

By bijim 13 Dec 2020

learning how to dress as a girl and more training on how to pleasure men

8.6 (40) 5378 16 Min Comments

Daniel Effeminate College Student (ch. 12)

By Colourfast 12 Dec 2020

A series of stories about effeminate college twinks and their encounters with mature gentlemen

8.3 (4) 641 18 Min Comments

Daniel Effeminate College Student (ch. 11)

By Colourfast 11 Dec 2020

A series of stories about effeminate college twinks and their encounters with mature gentlemen

8.3 (7) 641 21 Min Comments

Daniel Effeminate College Student (ch. 10)

By Colourfast 10 Dec 2020

A series of stories about effeminate college twinks and their encounters with mature gentlemen

8.7 (7) 824 15 Min Comments

Daniel Effeminate College Student (ch. 9)

By Colourfast 9 Dec 2020

A series of stories about effeminate college twinks and their encounters with mature gentlemen

8.6 (9) 581 22 Min Comments

Daniel Effeminate College Student (ch. 8)

By Colourfast 8 Dec 2020

A series of stories about effeminate college twinks and their encounters with mature gentlemen

8.7 (7) 660 22 Min Comments

Daniel Effeminate College Student (ch. 7)

By Colourfast 7 Dec 2020

A series about effeminate college twinks and their encounters with mature gentlemen

9.2 (11) 931 16 Min Comments

Daniel Effeminate College Student (ch. 6)

By Colourfast 6 Dec 2020

A series about effeminate college twinks and their encounters with mature gentlemen

9.0 (9) 820 20 Min Comments

Daniel Effeminate College Student (ch. 5)

By Colourfast 5 Dec 2020

A series about effeminate college freshmen and their encounters with mature gentlemen..

9.0 (12) 853 25 Min Comments

Daniel Effeminate College Student (ch. 4)

By Colourfast 4 Dec 2020

A series about effeminate college freshmen and their encounters with mature gentlemen..

9.1 (10) 1038 16 Min Comments

Daniel Effeminate College Student (ch. 3)

By Colourfast 2 Dec 2020

"Yummy" story.. about effeminate college freshmen and their encounters with mature gentlemen..

8.7 (11) 1128 15 Min Comments

Daniel Effeminate College Student (ch. 2)

By Colourfast 1 Dec 2020

Yummy" story .. about effeminate college freshmen and their encounters with mature gentlemen..

8.7 (19) 1945 25 Min Comments

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) 4947 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.

9.4 (30) 4407 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 (93) 10276 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) 4739 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) 3218 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

8.1 (18) 1808 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 (119) 26922 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) 1604 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) 4734 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) 7051 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) 563 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) 2472 3 Min Comments

my life (ch. 14)

By bijim 25 May 2020

agreeing for a second week of training

9.4 (14) 2406 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) 1136 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) 12978 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) 13921 6 Min Comments

Nocternal Eminations

By Mikal 7 May 2020

A story about being abducted and fucked by demons.

8.1 (14) 2722 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) 8460 7 Min Comments