Gay Sissy Training Stories

2,817 results
Orientation
Length
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Infinite Scroll

My Husband in My Panties Pt. 02

by eviltwin52 on Dec 9, 2019
Gay Male

Please read Part 1, My wife's perspective first. Johnnie's perspective If you read my wife's version about how much I enjoyed wearing her panties please let me explain myself. Not only did Cin help me realize and accept my fetish but she freed my inner submissive and bisexuality. I'm not here to refute nor challenge Cin's interpretation of anything. It's...

How I Became a Sissy Slut

by DixeenormousToo on Sep 15, 2017
Gay Male

I wish I knew I had these sissy urges when I was younger. Who knows, instead of getting married, having kids, and living the "American Dream," I might have discovered hormones, worked my body into shape, and become a tranny porn star. After all, how often does the American Dream really work out anyway? I'm unhappily divorced, my oldest is on his 6th year of...

Full Sissy

by Nils Huim on Dec 24, 2017
Gay Male

Darren couldn't believe his luck. Couldn't believe this was his wife Joy's birthday present to him. It was by far the best—the most exotic and erotic anyway—he'd ever received, in 35 disappointing years. He thought about this as his self-announced "date" rolled a condom down his beautiful cock, and again, moments later, when he was penetrated by it. Darren...

Sorted at the Funhouse Ch. 02

by thick1191 on Aug 30, 2017
Gay Male

This story can stand alone but will be much more enjoyable if you have read the first part; "Sorted out at the Fun House" found at my Authors site (dodge1191) on Litererotica. * I think anyone interested in reading this story realizes that I would return many times to the Fun House. It was just so erotic. About two or three times a week I would go there,...

Was I Raped? Ch. 04

by eviltwin52 on Sep 14, 2017
Gay Male

"What the fuck did you say to me bitch?" Uh oh. I'd pissed Daddy off. I'd been whoring for Daddy for three weeks now. I can't remember the number of black gentlemen who have enjoyed what I have to offer them. Still using my hotel room, every penny I earned went to Daddy. But that was a problem. The hotel wanted their room paid for and my credit cards have...

My White Boy Sissy Pt. 01

by wolf_hunt on Feb 25, 2019
Gay Male

This is part 1 of an ongoing series. It's just an intro with only a blow job scene. In future chapters there will be more including forced feminization, anal, humiliation and much much more. Hope you enjoy my story. All characters involved in sex are 18 or older. This is from the perspective of a black teenager as he turns a sissy nerd into his bitch. ****...

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...

The Talent Scout

by eviltwin52 on Jun 5, 2019
Gay Male

The day I first met him was like any other day. Riding the Metro to work I was suddenly jostled out of my reverie by some one bumping into me from the back. Turning I found myself looking up at a ruggedly handsome man. His steely grey/blues seemed to pierce into my very being. I wanted to look away but was unable to do so. After a few seconds that seemed to...

Fraternity Slut

by oskarwild on Sep 14, 2017
Gay Male

College was great! High school sucked. And Sam was glad to leave it behind. He had been an awkward boy in high school. Short and skinny - only five-six and a hundred ten pounds - and pimply-faced, he had never been able to attract the hot girls that the jocks were able to get. But things began to change when he hit his eighteenth birthday shortly after gradu...

Fantasy Out Of Control

by gbr2004 on Aug 18, 2017
Gay Male

I'm a divorced man living in Las Vegas. Recently retired, live alone and live a relatively normal life. I'm in decent shape for my age, 5'8", 180, and stocky build. I have been straight for the majority of my life. For the last few years, I have started to think more about getting together with another man. It goes beyond just this, as I want to be submissiv...