Gay Sissy Training Stories

2,817 results
Orientation
Length
Source
Infinite Scroll

Bringing Out the Sissy in Fred

by 0ra1Master on Aug 18, 2017
Gay Male

"Yessss.., ooh yesss, aahhh! yesss! That's it! Thaat's iit! God it feels good, so good! Ohh Sammy! Fuuck mmee! Yessss, yessss, fuuck, fuuck, yesss!" Mary Pats nails were digging into my shoulders; her ankles were hooked on my ass cheeks. I wasn't sure who was riding who but it was what it always was, a great fuck. "Give it to me Sammy! Harder...., h.a.r.d.e...

How I Train My Bitch-Boys

by bjmichaels on Sep 14, 2017
Gay Male

The secret of properly training a boy is conditioning his mind; opening his mind to the endless possibilities of sexual pleasure. Some men train their boys through the use of force and physical intimidation--I strongly disapprove of that method. You desire, as your end result, a boy who willingly submits to your every sexual demand because he wants to—becaus...

That's My Good Boy

by Submissivegoodboy on Sep 21, 2020
Gay Male

Bethany and I arrived at the hotel early that morning. We spend the day talking, snuggling, kissing, giggling and getting ready. Around midday I go into the bathroom and shave my body, we want me to feel extra sexy and feminine for my first time with another man. Mmmm as I come out naked and smooth Bethany giggles and jumps up and runs over to me. After sl...

House Rules Ch. 07

by EROTICbearscribe on Aug 7, 2019
Gay Male

WALKING THE WALK "We're going to have a visitor today," Daddy announced during breakfast one morning. He was wearing a suit because he had a business meeting. He looked very sharp. My daddy was so handsome. I was such a lucky sissy. When I asked him who was coming, he told me it was Miss Marguerite. "Miss Marguerite from The Beauty Mark?" I asked. L...

The Boifriend Ch. 01

by AdmiralSquish on Aug 8, 2018
Gay Male

[pre-story]Content Warning: SUPER gay. Crossdressing. Sissy self-deprecation. There's going to be some unrealistic anatomy later on, huge cock, huge balls, and huge loads. Disclaimer: All characters are 18+[/pre-story] ***** The Boifriend, Chapter 1 "Whelp!" Leo exclaimed as he stood up and gave an exaggerated stretch, feigning a yawn. "Looks like it's t...

I Once Was Lost But Now Am Found Pt. 02

by eviltwin52 on Oct 5, 2020
Gay Male

In Part 1 I found a friend in Leon. Having lived the greater part of my life alone, maintaining my bond with Leon was the most important mission I'd ever had. Sucking his cock was my way of showing him my appreciation for his comradery. He didn't ask me to do that. He didn't tell me to do that for him either. All Leon did was nudge me in the right direction....

What Being a Sissy Wife Means to Me

by SissyWife on Aug 18, 2017
Gay Male

I am a sissy wife. I hate clichés as much as the next girl, but sometimes they make for the most apt of descriptions. I have a job, friends, and a life. I go out, I go out for movies and drinks. I enjoy long walks and drives, and I love travelling to new places and locations. And yet, there was something missing. There was something that was needed. I found...

Chubby Sissy Meets His Daddy

by vulpinechub on Sep 19, 2017
Gay Male

The following story is a work of gay fiction. It contains sexual acts between males. This story focuses on: Humiliation, diapers, sissy play, domination. Copyright 2014 -- Feedback is appreciated. * My university decided to cancel classes for the day, but it was too late: I was stuck in the worst traffic of the decade. Mainly due to the incompetence of b...

Ozark Bitch

by oskarwild on Sep 14, 2017
Gay Male

Stranded Patrick let out a stream of obscenities as he kicked the tire of his rental car. The damn thing had stopped running in the midst of a rainstorm the likes of which Patrick had never seen before. It was a veritable deluge and Patrick was soaked to the bone as he tried to figure out why the car had just stopped running. He was on his way from Springf...

From Brother to Bitch Ch. 02

by Mixedwritings1993 on Aug 29, 2017
Gay Male

James was sleeping soundly, around 8 o'clock still sucking his thumb like a baby. At that time, the alarm went off, waking him up instantly. The sleep wasn't such a deep one because he woke up too many times while finding himself in the middle of various nightmares. He sat up on the bed, rubbing his eyes. His entire face was wet from the baby like drooling...