Gay Sissy Training Stories

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Job Evaluation - Employee of the Month

by VeryCuriousIan on Mar 18, 2020
Gay Male

Ian's turnaround at the company had been miraculous; his work rate, appearance, attitude, and demeanor were exemplary. His colleagues couldn't believe the change in him; luckily, none of them had ever stayed late to see how he was trained. Carol had boasted to her female colleagues how her hands-on training had brought about this amazing rebirth. Even Ian...

Fat Bottomed Girl Pt. 05

by eviltwin52 on Jun 4, 2019
Gay Male

It's gotten to the point that I'm chained to my obsession to a fat bottomed girl. I've allowed myself to be molded into that mate Sheila wanted. I mean before Sheila I was a woman chaser. A woman with a big ass fascinated me, aroused me, and now I'm a slave to my fetish. Sheila dominates every aspect of my life. Me queering off for her is just another way fo...

The Sponsors

by analvirgin4older24 on Aug 18, 2017
Gay Male

Back when I was just an 18-year-old high school senior. I was an Olympic caliber swimmer. After an All-American senior swim season, I decided to compete in state, regional, and national competitions. To do this I had to seek sponsors for expenses such as training and lodging at each competition. Luckily my dad knew this guy Ralph who owned a construction,...

Tame Cocksucker

by drmweaver705 on Jun 8, 2020
Gay Male

All participants are over 18. The idea for this story was suggested by donaldelliott11, with thanks. ***** "With this ring, I thee wed," Angelica said. With this yoke, I thee burden, Artie's mind echoed, just one moment forgetting the perks that came with marrying this fat, moody cow. Everything had moved so fast. Artie had the good fortune of working f...

Discovered by a Black Guy

by chastity_sissy on Sep 14, 2017
Gay Male

I should preface this story by saying I've never identified myself as homosexual, but sometimes after being locked up in chastity for a long time combined with crossdressing, I must admit to some fantasies involving other men. I never expected anything to ever actually happen, and it's my own fault really. I had been paying a beautiful, very sexually fetis...

Turning Myself Gay

by bart_allen on Apr 10, 2018
Gay Male

How did I end up as... well, you'll see. That's the whole point of writing this all out. A little story about how my life got flipped, turned upside down. Humorous references aside, my life certainly has changed, and was done on purpose. I guess I should start at the beginning, but that's difficult. My start was boring. No different than most people, I suppo...

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...

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...

An English Boy Gets Turned Out Ch. 03

by RustyRover on Sep 14, 2017
Gay Male

Mr Tobias was at work earlier than normal today. He had an early meeting with Mick to discuss the new star of their porn website. The Porn industry used to be a license to print money but that had changed over the last few years. Now there was more free porn available than paid for porn. Between Porno YouTubes knock offs, torrents and all these other sites e...

Head Counselor...

by emittsrif on Aug 18, 2017
Gay Male

This story is the third in a series of stories in which a camp counselor in training, Brian, is seduced and lured into pleasing his older counselor Mark. Can be read on it's own or as part of the series.. ...as always, I appreciate feedback! After the last two nights, the first in which Mark snuck bedside and jerked me into ecstasy and fed me my own cum, an...