Chastity Cuckold Stories

13,138 results
Orientation
Length
Source
Infinite Scroll

Humiliated Stable Sissy

by SissyTwinkleToes on Oct 5, 2020
Transgender & Crossdressers

After a long week at work, I was looking forward to a quiet weekend of relaxing in front of the TV with a beer, but my fairy godmother had other ideas. "Good morning sissy," came her stern voice as soon as I woke up Saturday morning. I whimpered, immediately knowing I was in for a humiliating weekend. She frowned, not pleased with my whimpering. She's an ol...

Humiliated Stable Sissy Pt. 02

by SissyTwinkleToes on Oct 5, 2020
Transgender & Crossdressers

I woke up exhausted at the crack of dawn to Fairy Godmother obnoxiously clicking her fingers next to my ear. I minced downstairs, still locked into my ultra prissy outfit (where was the key?) and my totally exposed diaper, already damp from last night. I shuddered as Fairy Godmother ordered me out into the back garden, where I stood and curtsied to the risin...

Weekend with Elaine Ch. 05

by clarepanties on Sep 26, 2017
Transsexuals & Crossdressers

The following morning, Sunday, I woke to Elaine's normal want, i.e. to perform oral on her before anything else. She removed Jenny's panties and presented her now shaved cunt to me. It was, of course a pleasure to service the woman who was becoming my Mistress. This servitude was immediately followed by Jenny moving into position. Elaine reminded Jenny, "We...

Jess Pt. 02

by AndreaJordan on Sep 26, 2017
BDSM

When Tom had mentioned his interest in bondage games to his new flatmate, he had no idea that she'd embrace it so fully and so quickly. Tom now sat on the floor next to Jess's bed blindfolded, listening intently to every slight sound. He could feel Jess's underwear around his neck. She'd used the black silk garment to connect his neck to the metal bedpost wi...

Neighbourhood Terror to Sissy Pt. 09

by Fibaro on May 27, 2019
Transgender & Crossdressers

While Mark was going through his night time ritual and sleeping Lisa was at CC's getting licked to orgasm after orgasm by Stephanie. The more she learned about sissies the more she knew it was what she had always wanted. She had never been with a such a pretty girly girl like Stephanie, and definitely never with anyone who was that good with a tongue. The th...

The Sissy in the Loft

by Sissy_Sammi_ on Dec 31, 2018
Transgender & Crossdressers

*All characters are 18+ *** James grit his teeth and walked through the door, a bell ringing as he entered the store. It was getting late and the sun was setting outside. He had been waiting in his car for nearly 20 minutes, waiting for people to leave the shop and no longer be near the store. The lady running the shop looks at him with a strange look fro...

Lost in a Female's Pleasure Pt. 08

by LucysFox on Jul 3, 2019
Transgender & Crossdressers

Synopsis: Damien was looking forward to a relaxing weekend free from his abusive father but things quickly took a downward turn when he got kidnapped. It appeared that maybe it was for the best, or at least not as bad as staying with his dad would be. Things start to become more complicated though as Damien reaches the brothel... Authors Note: I just want...

A Midsummer's Saga Pt. 04

by oneCresserelle on Jul 1, 2019
Sci-Fi & Fantasy

Gabrielle was woken up the next morning by a servant knocking cautiously at her door and informing her that it was almost time for breakfast. With Mista not yet back, the princess had overslept. She hastily washed, dressed up and prepped up by herself. Useless castle with useless servants, she thought, tying back her hair. Over her entire stay her breakfas...

The Bet Ch. 13

by sadkins116 on May 20, 2019
Fetish

This is a continuing story about a young college coed who makes a bet with her longtime rival. She soon learns that her bitchy attitude and a stupid bet is costing more than a bit of humiliation, and has taken over her life as well as her sister's and her best friends lives. Although you should read this from the beginning, here is what has happened up till...

A Changed Relationship Ch. 02

by MarthaD on Sep 13, 2017
Fetish

This story is part 2 of a three part series, all of which have been posted. It describes one week in our life that would eventually have a big impact on our marriage and our lovemaking. For those who might not remember, the story begins on a Saturday as my husband begins a week of chastity and foot and body worship which he has agreed to in order to earn a f...