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.

I become a sissy to my daddy

By big ass faggot slut 20 Jun 2025

This is the story of how my daddy turned me, a already phat assed sisssy slut into a full time sissy housewife.

7.9 (60) 20225 6 Min Comments

Fan Meet and Greet

By Victor 18 Jun 2025

true story of me relenting to meet with a fan, a big, muscled, closeted, college athlete who was too perfect to pass up.

9.6 (73) 5316 15 Min Comments

The bad man did what I wished for

By BillyBoy 13 Jun 2025

i find a Dom man to meet up with. unfortunately, or maybe not, he has watched my posts for a long time and does everything I've even dreamed of. Or had nightmares of.

8.7 (37) 4684 4 Min Comments

Choose Your Fate

By Sissyboi69 11 Jun 2025

Three assaulter's are forced to decide what their punishments should be.

8.3 (52) 9608 8 Min Comments

Abusive Sissification (ch. 4)

By Kavya sissy 7 Jun 2025

It’s an incident where I was fucked raped and brutally tortured by a gang of 8 strong men and slowly turn me into their sissy whore

8.0 (41) 16705 5 Min Comments

I'm no longer the man in charge

By BillyBoy 6 Jun 2025

A normal guy gives in to his wife's requests to dress in her lingerie, giving him the best sex ever, but it's all a lie

8.0 (47) 4938 6 Min Comments

First time used as a lingerie slut at the parking lot

By Bott in lingerie 3 Jun 2025

For a few years now I have had a sex fantasy to dress myself up as a slut, in ladies lingerie, and let a man use me. I am 29 years old and my fictitious name is Lin.

7.3 (20) 5038 4 Min Comments

Sissy Call Girl

By ChasingRisque 30 May 2025

Jesse's life is falling apart -- until he turns his secret passion for crossdressing into a dangerous new hustle: escorting for men. Each rough, raw encounter drags him deeper into shame and desire, confusion and craving.

8.9 (26) 4983 29 Min Comments

Bestfriend to Girfriend (ch. 2)

By imcocksucker1985 21 May 2025

Welcome friends to the next part of my journey of becoming my best friends girlfriend. As mentioned in the previous story, where I narrated as how a pact made in college, led us to have gay sexual relationship. Now coming to the next part.

8.7 (22) 3306 7 Min Comments

From Alpha to Obsessed (ch. 2)

By BeggingAndBlessed 18 May 2025

Jack Sterling’s world had shrunk to the confines of Blackthorn Penitentiary, where every breath was laced with danger and desire. The concrete cell he shared with Andrew, the 6’5”, 330-pound colossus, was a crucible of tension, each night haunted by the memory of Andrew’s sweat-slicked body,

8.6 (49) 7058 6 Min Comments

Older man gave me my first sissygasm

By BeggingAndBlessed 16 May 2025

How a man twice my age gave me the best sex of my life and the first sissygasm of my life

8.8 (48) 10772 5 Min Comments

Abusive Sissification (ch. 3)

By Kavya sissy 7 May 2025

Me being abused raped and tortured by 8 men for 3 days with no limits and restrictions, Please read part 1 and 2 to know the continuity

8.4 (31) 15374 8 Min Comments

Sissy Exposes Herself at the Cruising Park

By Bi_and_curious 5 May 2025

Married bi curious sissy decides to be a naughty little exhibitionist at a local park known for old pervs cruising.

7.4 (20) 5320 12 Min Comments

Abusive Sissification (ch. 2)

By Kavya sissy 3 May 2025

Chapter 2 : into the room of demon daddies

8.3 (44) 18134 8 Min Comments

Abusive Sissification

By Kavya sissy 29 Apr 2025

I let a group of 8 men of age 30 to 45 bang me for 3 days all they desire and anything and everything they desire to me with no limits no restrictions and no condoms

7.8 (77) 33055 5 Min Comments

Sissy for old Men (ch. 2)

By Cherrypie 26 Apr 2025

Our sissy slut has discovered she loves pleasuring nasty Old Men in every way possible..join in our sweet gurls journey

8.6 (27) 8396 16 Min Comments

Roberto the new cumdump for the BNWO

By Mexcumdump 23 Apr 2025

Roberto finds himself in the Black New World Order or BNWO were society is built upon a solid foundation of white boys to become a proper accessory for superior black males. To achieve the NWBO white boys are train at the Gay slave Academy to become a better sissies or faggots. That is its ultimate purpose.

9.2 (41) 10795 118 Min Comments

Sissy for old Men

By Cherrypie 23 Apr 2025

Cute young sissy discovers her need for cock..Old mens cock

8.3 (31) 10330 8 Min Comments

Wearing panties at the video store

By Alleykat 23 Apr 2025

I can’t forget that time I was wearing panties in the video store the clerk turned me into a sissyboi in just 20 minutes

9.3 (50) 7969 6 Min Comments

Trailer trash cumdump (ch. 2)

By Alleykat 22 Apr 2025

Three months ago I was drugged and made into a cum dump for old perverts at this trailer park i sucked cocks for the first time letting everyone cum on my face my naked body in my belly

8.9 (51) 7789 7 Min Comments

Rest-stop custodian my best job ever (ch. 2)

By Alleykat 21 Apr 2025

After getting a job as a rest stop janitor I broke up with my fiancé now I’m a full time cocksucker

7.9 (45) 3175 5 Min Comments

My full time journey

By Jester4fun 18 Apr 2025

The story of how and why I went full time feminine

9.3 (48) 4005 7 Min Comments

Pretty in Pink (ch. 4)

By Prettyboy 4 Apr 2025

Jackie is a cute twink who loves wearing pink. He is wearing new pair of pink leather Nike hi tops with white laces, girly white socks and silver anklets. He goes on line to find a top who will enjoy fucking a bitch wearing pink leather boots

7.3 (11) 936 5 Min Comments

Sissy Dad's Awakening

By ThePerfectcameltoe 21 Mar 2025

Chapter 1: A Hot Mess. In this chapter, an alpha son named Boland receives a distress call from his omega father, who's struggling to cope with a chaotic situation. Desperate for support, the omega dad reaches out to his son, seeking refuge and a temporary place to stay for a few days, hoping to find solace and stability with Boland.

8.6 (53) 6916 29 Min Comments

A Deal's a Deal

By Sissyboi69 8 Mar 2025

Jack finds out something he did to his girlfriend in the past has finally caught up to him... and now he has to pay the price.

8.7 (100) 12291 10 Min Comments

Meeting a gay sissy for the first time

By BillyBoy 5 Mar 2025

My first encounter with a true gay sissy was very eye opening. She liked it kinky. And being the good friend I am, I did my best to please her.

9.0 (24) 4456 7 Min Comments

Closeted Crossdresser

By slut4roughuse 15 Feb 2025

Blackmailed crossdresser sissy used by neighbor

9.2 (42) 9698 18 Min Comments

Gay sissy hookup with daddy dom

By BillyBoy 15 Feb 2025

Incest finds its way into a dark dungeon of a man

8.7 (39) 5903 4 Min Comments

Adult Store and Theater experience (ch. 4)

By RiverDylan 7 Feb 2025

Married man finds his true calling and he goes on a mission to get the attention of the man who abused him but also the man that he's in love with.

8.7 (13) 2698 17 Min Comments

My First Threesome

By BttmBoyAdventures 4 Feb 2025

My first threesome, where I learned what domination truly is...all while wearing black, lacy panties.

9.3 (32) 4950 14 Min Comments

Desire and Reality

By Torsten 2 Feb 2025

Carter, a spoiled rich boy, initiates a year-long social experiment. He'll live with five straight muscular men, fucked by them on schedule. The men are coerced to participate in this bold idea. Carter is straight, it's about notoriety and shock value rather than his sexual orientation. It has unexpected and humiliating consequences.

8.2 (17) 6534 206 Min Comments

Tyler said he was a top

By BillyBoy 29 Jan 2025

Tyler said he was a top, but he didn't sound stern enough. I was wrong!

8.4 (27) 2203 4 Min Comments

Pounding the Sissy

By Torsten 15 Jan 2025

In a world where strength is measured by muscle, Mick Malone is unprepared for Dorian, the sissy the government sends to assist him with the chores and sexual needs. Their days are marked by Dorian's lewd appreciation for Mick's sweat-soaked body, while Mick's physical dominance is tested by the shameless behavior of the government-assigned sissy.

8.7 (17) 3004 23 Min Comments

Adult Store and Theater experience (ch. 3)

By RiverDylan 14 Jan 2025

After being blackmailed, the married man subconscious betrays him.

9.3 (25) 3810 12 Min Comments

How I became an adult bookstore slave (ch. 2)

By Filthyslagbag 8 Dec 2024

I fully immerse myself into my new role.

8.2 (52) 8078 4 Min Comments