Crossdressers Chastity Stories

18,166 results
Orientation
Length
Source
Infinite Scroll

The Roommate Pt. 10 - Miranda

by ValoryG on Sep 13, 2017
Transsexuals & Crossdressers

True to her word, Miranda made sure Josh/Lori ventured out in public some more before his teaching duties resumed. The butt plug was frequently inserted, and when Lori asked why, Miranda remained mysteriously opaque about it. Lori was becoming more accustomed to the sensations down there - sometimes pleasant, sometimes a turnoff. After the movie (and the w...

The Trouble with Roommates Ch. 06

by KaylaG on Sep 18, 2017
Transsexuals & Crossdressers

Now that Nicole had settled in, things around the house seemed much smoother. The chastity cage didn't hurt, either. Something about having her dick restricted and untouchable seemed to heighten the rest of her senses. She even started to kind of look forward to hearing Brian get home from work and calling for her to give him a kiss. When he'd pull her in an...

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...

Futanari Housemaid Ch. 06

by femmevivante on Sep 25, 2017
Transsexuals & Crossdressers

Katerina's heart was racing as the three of them walked into the parlor together. Her cock and pussy were leaking so much that a wide stain was spreading over the front of her skinny jeans and her erection was clearly visible. Even the sensation of her cock brushing against the fabric of her lacy underwear and tight jeans was enough to increase her frustrati...

Caitlin and Mistress Vicky

by Jemina004 on Sep 19, 2017
Transsexuals & Crossdressers

*Clack* *Clack* *Clack* The sound of my heels on the kitchen tile was distracting me right when I needed to focus. My wife, or Mistress Vicky as I'm to call her from now on, had left me quite a bit of chores to do today. I had just finished dusting and was getting ready to polish the kitchen floor when the doorbell rang. *ring ring* Swallowing nervously,...

Sissy Girl Forever Pt. 01

by sissymissyct on Sep 18, 2017
Transsexuals & Crossdressers

The call from Mistress Andrea made my day. I hadn't seen her for over a week and was looking forward to playing with her & having my chastity finally removed. You should know that Mistress and I have known each other for many years and have I always enjoyed being her sissy sub. Lately she has been training me to be more feminine in appearance. I have been r...

Sissy Life: Valentine's Day

by sissymark79 on Sep 19, 2017
Transsexuals & Crossdressers

This is a standalone story in the 'Sissy Life' universe. You don't need to have read any of the other stories to enjoy this one, but it does fit with those in terms of characters & themes. Consider it a 'Rogue One'. ***** 'Have you finished in the kitchen?' I had indeed. I'd cleared the pots and cleaned the surfaces. I couldn't talk with my ball gag in how...

The Roommate Pt. 09 - Miranda

by ValoryG on Sep 16, 2017
Transsexuals & Crossdressers

The summer's heat accompanied Miranda's heat. Her and Lori's apartment didn't have air conditioning, so fans were usually on, and the roommates wore shorts, cami tops, short skirts, sandals and clogs, and shorter hair. Lori was kept so unbalanced by Miranda that she didn't eat as much as she used to, pre-Miranda, and remained quite slim. Miranda finally de...

Ultimate Sissy Weekend Ch. 01

by SissyTwinkleToes on Dec 24, 2019
Transgender & Crossdressers

Dressed head to twinkle toes in beautiful baby pink, Sissy Susie nervously waits for her friend to arrive and the most humiliating weekend of her life to begin. She winces as her teeny clitty squirms in its pink prison, a chastity cage that's been on for four frustrating weeks. Her cage is safely tucked away in her pink ruffly panties, covered in sweet littl...

Created in the Image of a Superior Being Ch. 04

by alyssawinters on Apr 22, 2020
Transgender & Crossdressers

The name of the CD bar he owned was called 'Over the Blue Moon'. It was the name of the one and only play Gary Stanisloph Kowalski the owner had been in when trying to make it as a stage actor 16 years previous. If he got drunk enough like the character artfully portrayed by 'Brando' he would playfully cry out 'Stella...Stellll-aaaaa' to the amusement of his...