Shemale Chastity Stories

8,093 results
Orientation
Length
Source
Infinite Scroll

Snowfall Seduction

by pantywriter on Sep 14, 2017
Transsexuals & Crossdressers

Early in the semester, the professor of Modern European Literature asked everyone where they were from, and whether they would be going home over either Thanksgiving or Christmas. Evan was from Arizona and already knew that his parents were planning on spending Christmas abroad. But the timing had not worked out for him with the start of classes, so his pare...

Caught Out, Made Over

by TanyaCc on Oct 5, 2020
Transgender & Crossdressers

It had finally happened. To be honest, I shouldn't have been that surprised. But here I was, dressed in my favourite sissy school gurl outfit, heels on, lipstick, wig and chastity cage in place, bent over the kitchen bench, getting reamed to the hilt by an 11 inch dildo on the end of my own fucking machine. I had cum dripping down my thighs, moans and groans...

Made to Obey Ch. 08

by madetoobey on Jul 29, 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...

(Wo)mans Best Friend

by Jagvillhem on Dec 14, 2019
BDSM

((Please be aware that this story is very much a heavy set fetish story. My writing is and will always be focused on the "darker" side of fetishes, and might upset some people. It is not my intention to bring discomfort, but with that said I wont go out of my way to tune down the intensity or depravity of the way that the fetishes are portrayed. Th...

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Master of the Manor

by AnInfrequentAddict on Oct 19, 2019
Fantasy

"HELLO!?" Amy barely hears her own knocking over the lashing downpour. The lights blinking in the window of the old, odd-looking estate had been the only possible reprise in sight. She had walked stubbornly for miles, convinced that the next town was far closer than it had proved to be, before stumbling across a huge wrought-iron gate amidst the th...

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Secret Makes Him a Cuckold Bitch

by Subkoksukr4u on Jul 29, 2019
Fetish

Getting caught doing something kinky or sexual for some people is a turn on, for others it's humiliating. There's lots of different variations. Like when you get caught doing something with another person or get caught doing something by yourself. Anyway way you slice it, getting caught can be embarrassing to some degree. This story is about someone finding...

Made to Obey Ch. 07

by madetoobey on Jul 10, 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...

To Serve Her Ch. 02

by njcaptionlover on Feb 26, 2019
Transgender & Crossdressers

After staring at the pink collar, I looked into Tammy's eyes hazel eyes and nodded. "I need to hear you say it, sweetie." Her voice was soft and gentle yet there was a commanding tone to it that made me feel meek. "Tammy. I would like to serve you as your live-in slave." I am not the type of person who makes hasty decisions but there is something about T...

Loraine's Self Bondage Re-Creation

by loraineveritas on Mar 12, 2019
BDSM

The following is my re-creation of an event that happened a few years ago. I had been a sissy slave to Mistress Marie for over 2 decades during which I become a totally submissive slave to Her every desire. I think of Her often as She has passed now. While doing Self-Bondage activities shortly following Her passing my wild imagination conjures up the Mistres...

Made to Obey Ch. 04

by madetoobey on Jun 24, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to a shemale porn site 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 cag...