Gay Sissy Bondage Stories

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A Tale of Slavery

by gunnarsub on Sep 17, 2017
BDSM

Once upon a time there was a straight guy who was known by everybody as a well respected fellow. But he had a secret life. Nobody knew that he dreamt to become a feminized slaveslut, seeking an infinite and irrevocable blackmail relationship with a pitiless Mistress who would be prepared to break him with no way out. He wanted the Mistress to torment him n...

One Step Too Far

by SatinDreamGirl on Sep 16, 2017
Fetish

The clock on the bedside table clicked loudly in the otherwise quiet room. A soft buzz of cicadas outside drifted in through the small gap in the raised window. The room seemed to glow with pink from the afternoon sun. The room hadn't changed much since Rachel had begun her fashion phase in high school. Her closet (and the closet of the guest room) were stu...

A New World Opens Up

by spaman100 on May 18, 2020
Transgender & Crossdressers

I was 25 when my parents were killed in an automotive accident leaving me with a sizeable inheritance and after settling the estate and having no family to speak of after my divorce, i decided to quit my job and travel the states. I found myself in Chicago on a beautiful Sept. day and needed a haircut, it had been 3 or 4 months since my last one decided to s...

The Visitor Ch. 10

by Leanne_sissy on Sep 26, 2017
Transsexuals & Crossdressers

I don't know how long I slept for, how long my poor battered mind floated in the warm sea of mindless contentment, before I came to. I stretched yawning, my body feeling stiff and strangely aching. All the memories of those things that I'd been subjected to were still a distant dream, until the realisation that I was still dressed in that horrible adult baby...

From Her Ex-Boss to her Bitch Pt. 03

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

This story contains extreme fantasies of Fem Domme, watersports, cock sucking, forced bi, if these aspects are likely to upset you please do not read on. ***** Pete had been taken in by Rachel, encouraged along the way, with a little titillation and confessions of her bisexuality. For a married man he had admitted too much and allowed himself to be taken f...

Sissy's Decline into a Slut Pt. 02

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Three: Another Exciting Night as Sissy Slut Wannabe. Well about a week has gone by since I bought the dildo, wrist cuffs, ice lock and the lubricants at the adult sex shop. Dressing up as a sissy maid or a sissy slut everyday at home and learning how to use the dildo first with my mouth and trying out the flavoured lubes for added pleasure, but most...

Mistress Red Fox Becoming a Devotee

by His_fag_wife on Sep 24, 2019
BDSM

A story of what might have been a dream. Names have been changed. *** One evening I was looking through profiles on a BDSM website and came across one for a local Mistress, she was developing a new dungeon and she was asking for suitable subs for her to try it out on. Someone to test the new equipment and layout on. I read the ad over and over again, this...

AliExpress and Sissy Downfall

by His_fag_wife on Oct 15, 2017
Transsexuals & Crossdressers

It all started with a visit to a TV Mistress on a work trip, Charlie had been cross dressing in some way or another since he was a teenager. First just his Mums used panties, then a lodgers underwear and finally he'd started to buy the odd thing himself. As time went on, BDSM was added into the mix, Charlie realising he was submissive and when he found Siss...

Sissy's Decline into a Slut Pt. 01

by Sissy_Chantel on Sep 13, 2017
Transsexuals & Crossdressers

Hi, readers, here is a new hopefully erotic story series of a sissy's decline to that of playing a sissy slut and then without her knowing soon to be a enslaved sissy maid and slut, featuring your sissy girl Chantel. Enjoy... ************************ Chapter One: Sissy Crossdressing Play Time. I'm sitting inside my car, it's late, a faint drizzle falls a...

The Prostate Exam Pt. 03

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his naturally submissive tendencies by pushing back against her finger, his female doctor had decided to test just how submissive he was. She gave him the option to back out if he didn't want to go any further, but she told him that if he did want to go furth...