Gay Sissy Crossdresser Stories

774 results
Orientation
Length
Source
Infinite Scroll

How to Come Out to Your Parents

by kicky1000 on Sep 14, 2017
Gay Male

How was I ever going to tell my parents that I was gay? This was a confrontation that I had been dreading for a long time, but how long could I put it off? If I didn't tell them, they were going to find out anyway for sure. I was a complete slut. I mean, really indiscreet. One time I got the mailman up to my bedroom, and he was just in the middle of fucking...

His Loving Beauty Ch. 03

by AaronCromwell on Sep 16, 2017
Gay Male

NOTE: I hope this chapter isn't too kinky for those of you who enjoyed the first two chapters, but if it is, I encourage you to read it anyway even if only for the plot resolution. ----- What happened after that Super Bowl weekend taught me a lot. The most amazing thing to me was not just that Damon committed to loving me; it was how smoothly and comfortab...

Hot Tub Trio Ch. 09

by Turbidus on Sep 17, 2017
Gay Male

I have posted the majority of this tale in the "Group Sex category. I don't wish to cause confusion but this chapter is almost entirely MM sex. For that reason I have posted in under "Gay Male" although there is just a touch of MMFF group sex at the end. Once again my thanks to LarryInSeattle for his help editing. As always any errors that remain are mine a...

Mechanics of the Heart Ch. 04

by ChicosTodos on Sep 14, 2017
Gay Male

© 2013 ChicosTodos. All rights reserved. No part of this story may be reproduced or transmitted in any form or by any means electronic or mechanical, including photocopying, recording, or by any information storage and retrieval system without the written permission of the Author. This is a work of fiction. Names, characters, places and incidents are the pr...

Becoming a Cocksucker: A Journey

by silkstockingslover on Sep 25, 2017
Gay Male

Becoming a Cocksucker: A Journey Summary: Man's journey from straight & married to loving cock sucking Note 1: Although unorthodox, this is a 2017 Valentine's Day Contest. No it's not a love story between a man and a woman, a woman and a woman or even a man and a man... it's a love story of a man and the discovery of his love for cock. No hearts and fl...

First Time Training Session Ch. 02

by playtime2728 on Aug 30, 2017
Gay Male

My throat was sore for a week. It got so bad that I lost my voice-my friends were all telling me to go to a doctor to see if I had strep, while I was secretly turned on every time I tried (and failed) to say something. No one suspected in the least that I was whispering because a strange guy with a big dick had given me an hour long lesson on what deepthroat...

The USS Cock vs the USMC Battleship Ch. 01

by Coxswain on Sep 14, 2017
Gay Male

THE USS COCK vs. THE LEATHERNECK BATTLESHIP Couldn't believe my eyes. Who woulda thunk? The Hulk had a weakness! I was amazed. Couldn't believe it. A monster like The Hulk with such a teeny weakness! It was like the Statue of Liberty jumping up on a chair screaming it saw a mouse. Let me explain. The Hulk was the biggest Marine I ever saw. An oversized R...

A Submissive's Journey Pt. 03

by CockServant on Sep 14, 2017
Gay Male

AUTHOR'S NOTE This is a story about a young man exploring his sexuality and finding out he is a gay submissive. It is rather long and not all about sex so if you are looking for a quickie you might want to look elsewhere. This is a fantasy. All characters are over the age of 18. Please enjoy. ------------------- The night air was damp as I walked the stre...

A Halloween Carol

by RubenR on Oct 24, 2018
Gay Male

This is my contribution to the 2018 HALLOWEEN CONTEST. It is not a sex story. For those looking for detailed descriptions of strong, muscled bodies, or hot, steamy sex scenes, try the next one on the list; you won't find it here. As always I like to know how the story is received. Comments are very much appreciated (even critical ones; insulting ones not so...

The Farmer's Sons Pt. 03

by rae121452 on Jun 5, 2018
Gay Male

It was early on a Sunday morning. JT and I had finished with breakfast and I was cleaning the dishes. Since we were the only two in the house, we'd gotten up nude and had our meal that way, too. JT was sitting in the corner rocker with his huge cock and balls hanging over the edge of the seat, swaying as he rocked. I was standing at the sink with my back to...