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.

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) 3678 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) 5981 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) 20968 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) 26855 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) 8870 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) 5885 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 (96) 11128 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) 7230 16 Min Comments

Meeting 'Katie'

By acessez 3 Apr 2017

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

7.7 (24) 2781 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) 7666 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) 38157 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) 8617 14 Min Comments

The sissy within me

By Ed 23 Mar 2015

This straight acting boy/guy has a sissy hidden inside him and is found out about by a friend who transforms him into the true sissy he wants to be.

7.5 (145) 50275 6 Min Comments

The neighbor made me his bitch

By mwmalone 25 Jan 2015

Older neighbor borrows some tools but ends up making me his bitch.

7.5 (477) 133293 10 Min Comments

Sissy slut Gangbanged hard and put up wet

By mwmalone 22 Dec 2014

Total fantasy of mine to be used by several men, even though this has not cum true I hope it will one day.

8.8 (216) 70367 13 Min Comments

Cross Dresser New Sex Friend

By gila Louieville 4 Jul 2014

The guy and sex fun dressed like a girl.

8.3 (64) 15145 8 Min Comments

Special help at a second hand clothing store

By CindyUSA 14 Feb 2013

I met a fellow cross-dresser on line. We agreed to meet at a used clothing store where he worked. He said he had a few outfits and offered to help me try them on.

8.0 (42) 6526 4 Min Comments

I did not know I had a disorder

By CindyUSA 26 Mar 2012

Roger is bi and likes to meet strangers to give them head. Ray is traveling and sees Roger post about free head. Ray wants to have a threesome with a She-male and when his plans change, he convinces Roger to wear sissy things.

7.4 (15) 3951 16 Min Comments

Tricked By A Sissie, Now Made Into A Sissy

By sissybrucie 21 Jul 2010

How I was a tough guy, now a panty wearing sissy.

7.1 (163) 32264 3 Min Comments

Becoming a Sissyboy

By Maikol 1 Mar 2010

I try pantyhose for the first time, enjoy it, get my buddy Corey to enjoy it too and we become sissy buddies.

7.7 (407) 58637 5 Min Comments

My New Pretty Sissy-boi James

By Maikol 26 Feb 2010

James comes over to my place to make some money posing for pictures and finds he enjoys the whole experience very much. At the end he is ready to come back for more.

8.2 (155) 32988 11 Min Comments

Sissy Gets A Drilling at the Army Camp

By cumfusion 22 Feb 2010

"He's oozing fuck out his ass! Look Don, Cyril must have given him one hell of a stuffing!" Jeff had his fingers in my crack and I just lay there .....

8.4 (29) 14945 20 Min Comments

Turned into a Mexican Master's Sissyboy Cockslave

By saltlakecockslave 24 Aug 2009

A young man is forced into a interracial role as a sissyboy for a Mexican Master!

7.0 (71) 21859 7 Min Comments