Gay Sissy Stories

27,439 results
Orientation
Length
Source
Infinite Scroll

The Gynecomastia Kid Ch. 01

by Johnboy9 on Sep 14, 2017
Transsexuals & Crossdressers

This story will be told in first person narrative but this first part is written in third person narrative because the first person, or main character, is unaware of the events unfolding in this scene. ***** Inside the kitchen of her boyfriend's house Crystal makes a last ditch effort, calling his stepmom, Dr. Burns, for help: "Crystal, you're saying all...

My sissy sister

by Alana-S on Jun 9, 2020
Transsexual

Did I really want this? That question had haunted me for weeks now. For years sissy porn had been my main masturbation fodder, and two months ago I had decided it could be more. That I could be more. I always wanted to be pretty like girls were, and had been openly bisexual for years. Why not try this? Why not be a sissy? I signed up to an online feminizatio...

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I Love Men to wear my Satin Panties Pt. 01

by Manndee on Apr 25, 2018
Transsexuals & Crossdressers

I was a quiet unassuming lad from the East end of London; I was 22 years old when I left home, it followed a number of pure flukes that all happened back to back, because of this I had had an amazing start to my life in my first job as a City trader. Unfortunately, things at home with my girlfriend were getting difficult after me losing my job. It was now 4...

The White Slave

by mspbottom4black on Oct 6, 2020
Interracial Love

Editor's Note: this submission contains raceplay and femdom content. * Not long ago it was a straight and stuffy white male. it was arrogant and self-satisfied with its white male social and economic leverage and advantages. In the rat-race of white society it suppressed its submissive white side. But from time to time it would slip into daydreams of hav...

Humiliated Sissy Husband Ch. 05

by rik581 on Nov 16, 2020
Transgender & Crossdressers

Max and Tonya walked in the front door after a morning outing in which Max spent the entire time complaining about wanting to go home. Max stood there wearing a little girls dress and high heels, with his wrist tied to his upper arms and hanging limply near his shoulders. His shoulders, waist and legs strapped extremely tight to the pole. They needed to be...

Sissy Girl Forever Pt. 02

by sissymissyct on Sep 18, 2017
Transsexuals & Crossdressers

No going back now. Mistress was going to be certain that there would be no turning back for me. Over the next few weeks she made certain that I used my hormone cream daily. No my breasts haven't started to grow yet but I could notice some slow down in hair growth. My male wardrobe seemed to be dwindling, with more camis, blouses, soft pullovers and ladies p...

College Misery Ch. 01

by newauthor19 on Sep 16, 2017
Fetish

Ever since words got out that James has some femboy porn hidden in his laptop it has been a nightmare for the 19 year old poor boy standing 5'8" and weighs merely 122lbs. His classmates have totally lost all respect for him. He was admired before for his friendly attire and kind hearted nature but now he is admired for his feminine body. He lives in a boy's...

Caught in a New Life Pt. 02

by Fibaro on Jun 15, 2020
Transgender & Crossdressers

(Hello everyone, here is part 2 of the story requested by one of my readers.) Chapter 3 While Monroe was having breakfast the next morning Lena passed by on her way out wearing a white body con designer dress with a black belt at the waist, black sheer pantyhose, a pair of white patent leather heels, big rounded sunglasses and a wide floppy white hat with...

How Nathan became Natalie Ch. 01

by saintlycd on Nov 22, 2017
Transsexuals & Crossdressers

My name is Natalie but that was not the name I was born with; rather it's the name my wife gave me when she made me her "sister" and her cuckold sissy not long after we were married. My real name is Nathan but that's a name I would prefer never to use again because I enjoy being Natalie much more than I ever enjoyed being Nathan. This is a story of how my wi...

Friday Night

by DrLuverotica on Sep 13, 2017
Loving Wives

I arrived home from work at 6pm on Friday completely exhausted. It had been a killer week in work. We had had some new software installed that had played havoc with our macs and it had taken half a dozen of us until 11pm the previous night to finally fix the wretched thing. As soon as I walked through the door I kicked off my shoes, poured myself a glass o...