Latex Sissy Chastity Stories

20,354 results
Orientation
Length
Source
Infinite Scroll

My Husband a Pornstar Ch. 03

by gtanya on Mar 20, 2018
Transsexuals & Crossdressers

Please read the previous two stories to fully understand and enjoy this chapter. If you don't want to read them, here is a brief description of what has happened till now: *** My husband was conned by me into exploring his sexuality and he finds out that he is bisexual. He also agrees on being a porn-star to earn a hell lot of money for us. After shooting...

How I went from Domme to Slut Ch. 05

by Ms_Allison on May 29, 2018
BDSM

Over the following few months from my first night waiting tables at the club things continued and amber and I fell into a comfortable rhythm with things. The first Friday of the month amber would wait tables during "men's night" and on the third Friday of the month I would wait them for the Ladies. When amber waited tables I was typically dressed in somethin...

Sissy Maid to Be... Ch. 02

by missjennymaid on Sep 10, 2018
Transsexuals & Crossdressers

I would recommend reading Chapter 1 to get to up to speed on the story, but if you want to start in the middle... Jeremy: A married crossdresser who loves to live out his crossdressing fantasies with his supportive wife. Lizzy: Jeremy's wife who participates in his sissy maid desires every other Friday when they have the place to themselves. Jeremy is get...

Mandy's Reward

by sissymaidrose on Sep 12, 2017
Transsexuals & Crossdressers

There was a sharp, heavy rap at the door. Mandy scrambled out of bed as Mistress Charlotte pushed the door open, hastily smoothing the tiny, soft, pink and green nightdress that barely went past her hips and surreptitiously tugged the matching knickers down from where they had ridden up into her bottom. As Mistress sashayed past to the throne like chair in t...

Like a Dream

by Scotsdude on Oct 15, 2017
Fetish

As I arrived at work that Monday, I knew that it would not be a normal day. My throbbing head was a distinct reminder of how my weekend had been. Saturday night was a blinder. It was my friend Kevin's 30th birthday, and as such, we decided to make it a bit of a blinder. It started out with paintball, went on to karting, dinner, and a strip club. Prague's st...

Slow Descent into Sissy-Hood... Ch. 02

by Slipperylock on May 11, 2020
Transgender & Crossdressers

I started pretty slow. I'd wear it for at first hours, then a day, and then finally overnight. That one had been the hardest, no pun intended. I would wake up multiple times a night, locked in sweet torture between the inevitably erotic thoughts in my head and the bittersweet tightness between my legs. The first time I'd tried it, I'd made it till 2 a.m. bef...

Wife in Control Ch. 07

by wifetoy on Sep 25, 2017
Fetish

This is the seventh chapter of my wife's fulfillment of the punishment poem I submitted suggesting ways to atone for my inability to control my orgasm. Please read the earlier chapters for the full poem and the humiliations I have been forced to endure because of my failure. I am grateful that my wife loves me enough to exercise the total control over me tha...

Caught

by ImpureChastity on Sep 13, 2017
Transsexuals & Crossdressers

I had been planning my downfall for weeks. Putting together the right outfit, working out the best place to be in the house, practicing my lines to appear convincingly surprised, everything was lined up perfectly. For a few months the relationship between me and my fiancé, Janice, had been just a little kinky. She had cottoned on to my submissive tendencies...

The Intern Ch. 04

by FrostShard on Mar 6, 2018
BDSM

The day after Mengxia had me listen in to her having sex with her boyfriend, I went back into work with some trepidation. Aroused from my three weeks denied orgasm, humiliated by the events of the previous evening and nervous about my meeting with Mengxia that evening, I could barely focus on work, and it seemed to take ages for 5 pm to roll around. At last...

Sissy Life Pt. 04

by sissymark79 on Sep 19, 2017
Transsexuals & Crossdressers

I stood to attention on my 'sissy spot', the small 'x' drawn on the floor of my Mistress' study. My spot faces the desk behind which is a large leather chair. It is here that I was told I would be placed in chastity. It was here on my spot that events unfolded leading me to serve my Mistress' lover Tony. I was understandably nervous about being stood here ag...