Gay Sissy Training Stories

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The Proper Sissy Training

by Johnyy on Jan 29, 2017
Gay

All started the day when Mike went to visit the gym. He was not a type of guy that had all the muscles, quite opposite. There was someting wrong with his genes, because he struggled and still had a skinny body. Fact that he was short only made it worse. He couldn't find any girlfriend and was still a virgin, taking the fact that he was 17. He hoped that he c...

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PIXIE Sissy Stripper Ch. 03

by EROTICbearscribe on Jan 6, 2020
Gay Male

Darryl Powers was on his way to one of the two popular nightclubs he owned. His new sissyboi, Benji, was beside him. The boi looked pensive and vulnerable, especially sitting next to Darryl. At 6'5 and a muscled but well-sculpted 230 pounds Darryl dwarfed the, for lack of a better word, 'petite' college boy sitting next to him. Anyone seeing the two pass b...

Guys' Retreat Pt. 05

by Cyanlot on Apr 21, 2020
Gay Male

Part 5: Brianna's Training "Vince had a terrific idea, Brianna," Kent said. "It's really going to make this easier for you." "Yeah," I said, noncommittally, knowing full well that whatever Vince had come up with wasn't going to be to my benefit, though I was sure it would benefit them. "Yeah. We've been downloading some videos for you to watch. You're goi...

My New Master

by jasoninsjca on Aug 18, 2017
Gay Male

Finding a new place to live is always a drag and I was spending Saturday morning looking through the online classifieds for someone to share a house or apartment with. There were plenty of ads that looked just fine but one jumped out at me and raised my curiosity. It was an ad from a 50ish guy looking for a guy to share his four bedroom house. That in itself...

I Turned Myself Out Ch. 03

by drmweaver705 on Aug 24, 2020
Gay Male

"Warning: this video is designed to turn straight men into gay bottoms. Don't say you haven't been warned..." The female narrator had a breathy, clear, commanding voice. It was a voice to be obeyed. "You've stripped yourself naked and stretched your ass in preparation for the arrival of your first ever top..." In fact, I was naked, lying in the marital b...

The Hanky Code Pt. 16

by His_fag_wife on Sep 14, 2017
Gay Male

Melinda opened the door to a very large guy, not tall but fat almost round. He waddled in smiling and sweating profusely. He carried a large Gladstone bag giving him the air of an old fashioned Doctor. Mistress Caprice said "Welcome Mr Smotherer, I hope you're pleased with your pig." "Ohhhhh yes, she looks perfect, I really have worked up a sweat on the wa...

Converted to Gay

by bart_allen on Sep 14, 2017
Gay Male

This story is partly inspired by messages from fans, with slight adjustments. Thank you for reading. ***** I wanted to share with you one of my current projects. A twenty five year old male by the name of Eric. Nothing too special in the looks department, but not too shabby either. He was neither heavy or slim, perhaps a slight softness to him. His eyes we...

Black Cock Worship: A Man's Fall

by silkstockingslover on May 1, 2018
Gay Male

Summary: Straight guard learns of black inmate's power over all. Note 1: This is dedicated to the real Ken who retold this surprisingly largely true story. Note 2: Thanks to Tex Beethoven, thor_ph, Robert, and Wayne for editing. Prologue: I'm the prison guard and Kareem Mwangi is the prisoner, so you would have thought I had the upper hand, and until...

Crossing the Line to Suck Cock

by ndeavour on Mar 25, 2019
Gay Male

I was nervous. Frankly, I was even a little afraid. Here I was, 60 and divorced, and I was about to meet a man for sex. After all those years of not even allowing myself to think of it, I had finally taken the step that had been in the back of my mind for years. I was going after cock. I told myself I was up for anything -- fucking, sucking, etc. -- except k...

Party Pizzazz Ch. 02

by bjmichaels on Oct 6, 2020
Gay Male

Party Pizzazz Ch. 02 by BJ Michaels If Tommy hadn't kept such a close eye on me all night at the party I would've ended up as a boy-toy for one of those rich men. That's what he told me afterwards in the car on the drive to his apartment. "Lucky for you I happened to overhear those five assholes bidding on you or you'd belong to one of them now," he said...