Shemale Chastity Stories

8,093 results
Orientation
Length
Source
Infinite Scroll

Made to Obey Ch. 11

by madetoobey on Aug 21, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). I'd been forced into a chastity cage and made to wear panties all the time. Humiliation was now a frequent event. Esther, who had investigated my internet usage on my laptop to see if I'd visited shema...

Yet Another Story

by neoview on Nov 26, 2017
Transsexuals & Crossdressers

You're back? I guess my previous story was a hit. The comments stroked my ego enough to write this bullshit. Before I begin, shout out to: Anonymous user, Anonymous user and xploring96 for the feedback. If it wasn't for you guys I probably wouldn't even bother to continue this... I guess I should make it a series... Naaahhhh. Too confusing. Super narrator p...

Made to Obey Ch. 05

by madetoobey on Jul 2, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). Ruth, as a part of my punishment, was setting me tasks until Esther (who'd taken my laptop and mobile phone) could verify I'd never visited such sites before. I'd been forced into a chastity cage and m...

Mia, Shemale Slave Ch. 01

by spitzharder on Sep 13, 2017
Transsexuals & Crossdressers

It was all due to a gorgeous oriental Shemale dancer, Solange, I'd seen earlier in the evening that I, a 23 year man, was standing in an alley in the rain naked except for black hold up stockings and black lace panties. My cock peeped over the top of the panties, glistening with the rain falling upon it. My thoughts drifted back to the erotic dance Solange...

How It All Began

by subboy85 on Sep 12, 2017
Transsexuals & Crossdressers

The room starts spinning slowly as the lights fade out, my mind is in a daze, and my body is all worn out. I welcome the warmth of the soft sheets as I close my eyes and try to sleep because I need my rest. The sweep familiar ache in my muscles causing sweet surges of pain from my very sore and well fucked ass, still dripping Master's cum, even now after all...

One of the Girls Pt. 02

by Erotictales4u on Sep 26, 2017
Transsexuals & Crossdressers

All characters in this story are over 21 years old. This is a fictional fantasy that contains elements of both femdom, maledom and transsexual/cross-dressers niche, it is focused on humiliation. This is the second chapter of One of the Girls. Sorry for the long delay. ***** The studio lights blinded and disorientated me for a few minutes as Lana led me by...

Mistress Jasmine Made Me a Slave

by Gretatv on Sep 18, 2017
Transsexuals & Crossdressers

Since long I haven't written a story so maybe I am a little rusty but I hope you enjoy it anyway. There are some autobiographic parts in it but most is fantasy, which part is real and which is fantasy I leave to you. Like any other author I do love comments too, whether they are good or bad. So please leave some words of praise or critics. Those critics whic...

Always Read Before You Sign Ch. 09

by Reaver90 on May 12, 2020
Transgender & Crossdressers

Paula was in the living room, having some toast as she watched the news on TV. She was waiting for Samantha to appear so she could launch her secret surprise on her slave. Samantha was in the kitchen, making herself a cup of tea. Samantha always enjoyed a cuppa in the morning. As she waited for the kettle to boil her mind drifted back to a few days ago wher...

Made to Obey Ch. 10

by madetoobey on Aug 6, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). I'd been forced into a chastity cage and made to wear panties all the time. Humiliation was now a frequent event. Esther, who had investigated my internet usage on my laptop to see if I'd visited shema...

Pam's Shemale Experience Ch. 10

by majicman21 on Dec 2, 2019
Transgender & Crossdressers

Pam woke up, and as she remembered what day it was, a smile crept across her lips. Earlier in the week, her owner had decreed that she would not fuck Pam until Wednesday. That had been Sunday night, and now, with Monday and Tuesday past, today would be the first time in a long time she would feel that magnificent cock opening her up. It's been too long.....