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.

CD Hotel sex

By Jester4fun 3 Oct 2024

Sissy CD takes dick in hotel

9.3 (133) 12565 8 Min Comments

My Transformation (ch. 4)

By RiverDylan 19 Sep 2024

Dylan becomes addicted to men, he finds himself a new boyfriend and with that new surprises...

9.1 (24) 13551 19 Min Comments

Miss Jenny from Ohio (ch. 4)

By Okamaguy 28 Aug 2024

Jenny spends the day as a schoolgirl and gets more cock than she bargained for.

9.7 (10) 3251 16 Min Comments

Big Brother is My Master

By Slutty Whore 25 Aug 2024

The Big brother becomes master of his little slutty brother and rents him out to people making him the whore for almost every menial job worker in the town. Enjoy the story and make sure to cum!!!!

8.5 (41) 12506 6 Min Comments

Bound Gagged and Gay'd Me

By BillyBoy 23 Aug 2024

He answered my ad, answered my fantasies, and answered my question: Was it good for you?

8.8 (21) 5275 8 Min Comments

How I became an adult bookstore slave

By Filthyslagbag 21 Aug 2024

How I became a bookstore sub

8.9 (113) 12404 5 Min Comments

Prison Substitute

By Con Twink 21 Aug 2024

A fresh juvenile comes into contact with hardened criminals, and one in particular has a profound influence on him…

6.2 (49) 14892 2 Min Comments

Twins bothers have lot more in common (ch. 3)

By Xoxo 19 Jul 2024

Harry gave his BBC friends a little show

8.9 (10) 2598 7 Min Comments

Straight guy turned gay (ch. 6)

By Jaden 27 Jun 2024

A new experience - It was Monday morning, I woke up and found myself alone in bed. I found the sexy french maid outfit on bed. I wore it and headed to the kitchen. My master was having breakfast by himself.

9.5 (27) 7832 9 Min Comments

Straight guy turned gay (ch. 5)

By Jaden 25 Jun 2024

Unexpected day - It was sunday morning. I woke up to a weird and amazing feeling. It was my master's cock deep inside me. He was holding my caged cock and fucking me hard. My whole body was sore from last night, but it was like a fantasy come true. 

9.2 (33) 8291 7 Min Comments

Straight guy turned gay (ch. 4)

By Jaden 23 Jun 2024

Wild night made my whole body sore.

9.0 (45) 10489 14 Min Comments

Straight guy turned gay (ch. 3)

By Jaden 22 Jun 2024

Turned into a sex slave.

9.1 (58) 12140 6 Min Comments

Twins bothers have lot more in common

By Xoxo 22 Jun 2024

Harry finds his brother suck neighbour BBC without sharing with him

9.4 (16) 4865 19 Min Comments

Chase the Bad Cop

By Nyx Stronghold 17 Jun 2024

Chase the bad cop, that's me. I fuck some thug on the street for no reason. And this is that story.

8.3 (23) 3783 6 Min Comments

My Transformation (ch. 3)

By RiverDylan 6 Jun 2024

Dylan finds out a heartbreaking aspect about George and finds love in a new man.

9.2 (39) 8970 7 Min Comments

My Transformation (ch. 2)

By RiverDylan 5 Jun 2024

Dylan finally gives in completely, his more mature lover fucks him and demands certain changes in his life and body. Dylan obliges and adapts a new life.

9.0 (43) 12115 9 Min Comments

First time at a gloryhole

By Jester4fun 26 May 2024

True story of my first time visiting a gloryhole

9.3 (144) 10626 6 Min Comments

My Transformation

By RiverDylan 22 May 2024

This is the story of Dylan. A "normal guy" that became a victim of his own lust and gave into a new way of life

9.2 (85) 20712 11 Min Comments

Auntie and Uncle

By David Tossell 4 May 2024

A boy living with Aunt and Uncle for a holiday

6.5 (34) 6337 3 Min Comments

Chrisy - The Sissy Slave

By Slutty Whore 4 May 2024

See how two horny ass adults convert a straight boy into a submissive sissy slave that becomes a horniest slut

8.2 (64) 12987 6 Min Comments

Straight Arab Roommate

By employee007 21 Apr 2024

A medical student's world is turned upside down when he is paired with his new roommate, an Arab exchange student.

8.8 (170) 24785 21 Min Comments

Stacey's First Love

By luvaslip 14 Apr 2024

Stacey remembers her first love and more

9.5 (11) 1722 17 Min Comments

Lord Laywood Gets Pimped Out

By EasyWhenDrunk 12 Apr 2024

Eden Laywood's father pimps him out to strangers to fund his estate. The only thing his father doesn't know...he's a slut and needs cock bad.

9.0 (63) 7670 3 Min Comments

Gay or Not Gay?

By BillyBoy 27 Mar 2024

How did I know? I wasn't just walking into a gay porn club and waving a rainbow flag. I needed to be persuaded, seduced or pushed a little bit, so I could say, I'm not gay, they made me gay!

7.5 (22) 3295 6 Min Comments

How to become a good cocksucker

By Gayguy69 9 Mar 2024

Billy was a sissy of a boy always playing with his sisters dolls and wishing he was a girl

6.4 (35) 3497 1 Min Comments

Crossdressers first BBC

By Jester4fun 26 Feb 2024

My first BBC

9.2 (236) 20640 8 Min Comments

Mr Tippet's young lover (ch. 3)

By Okamaguy 18 Feb 2024

Schoolmaster Tippet dresses me as his sissy student and gives me a lesson

9.5 (19) 2996 7 Min Comments

Coercion (ch. 8)

By Tommy 11 Jan 2024

My adventures into sexual awareness was becoming complicated and more fun and I love the fun and sexual adventures, the complicated would change me.

9.2 (9) 1697 8 Min Comments

Blowing unknown guys cock

By Rukygay 31 Dec 2023

Unknown but served

5.7 (28) 4011 2 Min Comments

Got my wish (ch. 2)

By Luvonstkylip 18 Dec 2023

This is the other part of " Got my wish".. My crossdressing encounter that I had one night when I was spun!!!

8.2 (18) 3241 2 Min Comments

Turned Out

By Zac Smith 1 Dec 2023

How I was turned out in prison

8.9 (106) 23360 12 Min Comments

Gay Catfight for an Alpha

By Derick Gold 23 Nov 2023

Husband vs Boyfriend for their MAN excerpt from the hot new book NASTY NEIGHBOR

8.9 (20) 4706 8 Min Comments

Falling off the Edge (ch. 7)

By Draven Moorcock 22 Sep 2023

Dan muses over what he is putting his husband through, struggling to understand himself, and his growing love for another man.

9.1 (25) 2080 12 Min Comments

wife mademe a pathetic sissy cocksucking slave

By BillyBoy 13 Sep 2023

my new wife wasn't what she seemed. she turned me into a sissy, then a strap-on fuck toy, then brought in men to fuck her while i watched, then men to fuck me while she watched. It's a long story, but I'm caught up here forever now.

8.2 (75) 14159 9 Min Comments

Mistress of Cindy submitted male slut

By Italian sub Cindy 8 Sep 2023

how my wife from submitted become Mistress and me amale sissy, submitted and slut

8.4 (20) 6139 19 Min Comments