Gay Sissy Crossdresser Stories

774 results
Orientation
Length
Source
Infinite Scroll

Do It for the Money

by vikkihawe000 on Sep 23, 2019
Gay Male

It was no secret things had been hard for Tori and Max and it was no secret the reason why. He had left his lucrative private equity job to start a restaurant. The loss of income (and 75% of their savings) had taken its toll. After several consecutive months of draining money, Tori went to work at a local coffeeshop to make some extra cash. She didn't love t...

Jet Lagged

by Kabba118 on Mar 3, 2020
Gay Male

This is my first submission, please be gentle. :) I welcome constructive criticism and feedback. Thank you for taking the time to read my story: Jet Lagged. * I slowly open my eyes and look at the time. 1:14am. Of course. Because it was 6:14am in Casablanca. I would be up with the rising sun, possibly having coffee on the veranda right about now. Instead I...

Cock-Sucker: Weekend Ch. 01

by tristantrotsky on Apr 3, 2019
Gay Male

Broke. Down and out in Paris. Hiding out from brutal creditors. I'm in scarily way too deep. If you wanna hear about it, the things I did, the predicament I find myself in, all you have to do is buy me a cognac... and listen, eventually I may come up with the truth, only slightly embellished. Of course, you'll never be certain which parts are true, and which...

Seduction, Submission and Surrender

by yukonnights on Sep 15, 2017
Gay Male

This is the story of another time. The Vietnam war was tearing the country apart and young people were beginning to throw off the outdated rules of a society. The year was 1969 and the place was Boulder Colorado where two young men met and embraced their homosexuality. It is also a story of dominance and submission and the myriad emotions these roles bring f...

Keep Rolling

by jerrymiah on Aug 18, 2017
Gay Male

Hi! This is my first time in writing fictional story. I'm sorry if I have a lot of grammars and wrong term I used here, because English is not my main language but I'm trying to hone it by wiring story in English form. If you want to be my editor, feel free to send me an e-mail ^_^ -Jer "What?" I snapped at Laurence. Frowning at me while putting a bill o...

Foundry Furnace Ch. 02

by rae121452 on Mar 27, 2018
Gay Male

Please note: Although no incestuous contact occurs in this story, it does contain incestuous themes. ***** Cole and I had been living together for about 6 months. After that first weekend fuckathon we hadn't spent a night apart. I had moved into his place and we considered ourselves an established couple. I'd told my folks about him during our weekly phone...

The Head Boy's Fag Ch. 01

by JASONSHOMOEROTICA on Oct 15, 2017
Gay Male

THE HEADBOY'S FAG - 1 THE FAG'S FIRST DAY AT OLLERTON COLLEGE A Homoerotic Story This is a short story concerning the the Head Boy's fag at an English public school called Ollerton College, located in a small county in the south west of England. The time is the early twentieth century, before the Great War, which changed so many things in England. But at...

Billie's Sore Ass

by erectus123 on Jan 13, 2018
Gay Male

Billie's Sore Ass: Sexual Fraternity Hazing [Readers, be assured all events take place between men who are 18 and older. There are no minors or Appalachian miners depicted here. Most are college guys who range from 18 to 32 years old. A few older men do appear towards the end of the story to add a mature balance. All characters in this story are based on re...

Jeurridam Ch. 12: The Hoover Dam

by StillnessIsTheTruth on Aug 31, 2017
Gay Male

EZEKIEL: I didn't know the cafeteria opened this early! The would save me a trip to one of those numerous burrito shops around Jeurridam. It was so aggravating having to do so every morning! However, I probably would do it anyway. The platter I was preparing was not for me but for Zanir. Today was a very, very special day! It was Zanir's birthday! He was...

Playing with Matches

by Schenkkan on Aug 18, 2017
Gay Male

I Around the living room, Cole raked his irises of honey-brown. Never had he seen so many matched items and polished surfaces. No wonder Rick wanted his other property painted pronto—to pay for the goodies of this house with the rent income of that apartment. "Would you look at that screen?" Rick said. He sat up on his black loveseat of leather. "Ou...