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.

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) 4854 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.

8.8 (24) 4701 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) 3232 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) 6918 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) 10243 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) 14452 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) 5042 12 Min Comments

Abusive Sissification (ch. 2)

By Kavya sissy 3 May 2025

Chapter 2 : into the room of demon daddies

8.3 (44) 16985 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

7.9 (76) 30822 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 (26) 7869 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 (40) 10184 118 Min Comments

Sissy for old Men

By Cherrypie 23 Apr 2025

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

8.4 (29) 9617 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 (48) 7571 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 (50) 7337 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) 3038 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) 3872 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) 928 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) 6679 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.

8.6 (99) 11988 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) 4296 7 Min Comments

Closeted Crossdresser

By slut4roughuse 15 Feb 2025

Blackmailed crossdresser sissy used by neighbor

9.2 (42) 9356 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) 5748 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) 2629 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) 4777 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) 6428 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) 2177 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) 2957 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) 3743 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) 7877 4 Min Comments

A sock-sub's journey to slavery

By Lowlifesocksub 28 Nov 2024

A sock-kink crush unexpectedly resurfaces after years, taking Tom on a journey from sub to fag to sissy slave, proving that a true sock-kink will do anything to get his hit, and that fantasy and reality don’t always match up.

9.6 (25) 6585 29 Min Comments

Family Affair

By VersHornyGay 26 Nov 2024

Family is feeling pent up and needing release, trapped in the same four walls with each other and with no-one else to turn to other than blood-related-family...

8.7 (109) 16229 9 Min Comments

Control and Corruption

By isaline_cd 20 Nov 2024

A dominant daddy meets up in public with a straight married man. Daddy decides to mark the wannabe sissy as his submissive slut.

9.6 (83) 12746 27 Min Comments

Sissy's Bizarre Adventure (ch. 4)

By Dray Sandrix 9 Nov 2024

In this chapter, Diana, the newly initiated sissy slave, and her Master, Alex, embark on an electrifying adventure into the unknown. At a BDSM party filled with secrecy and desire, Diana's deepest fantasies are unveiled. Blindfolded and surrounded by eager participants, she embraces her role as "Diana, the Wonder Whore," seeking anonymous encounter

8.9 (10) 2621 6 Min Comments

Straight guy turned gay (ch. 7)

By Jaden 23 Oct 2024

The new me - My whole body changed. I didn't have any body hair anymore, which made my body really smooth. My voice was softer. I grew my hair long. It almost reached my mid back.

8.8 (22) 8829 16 Min Comments

Closet crossdressing goes very wrong, or did it?

By BillyBoy 10 Oct 2024

Dressed in private but I have to answer the door for my neighbor. It turn out to be a very naughty afternoon.

8.2 (35) 7477 6 Min Comments