Trans Chastity Stories

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Trans-Formation

by dreadknots on Jan 20, 2020
Transgender & Crossdressers

This one is a lot more silly than my previous outings, but I think it's still a good read! Featuring guest appearances by chastity, dildo buttfucking, and hypnosis! Oh and turning into a girl at the end, that too. *** "Well," Tim said to the smouldering crater now taking up the majority of his backyard, "This isn't going to help the property value." An or...

A Trans Woman's Submission

by ahbedeah on Aug 20, 2018
BDSM

Mistress can't blame you. She knows that you need someone to do your thinking for you. She knows that you need someone to control you. But she wasn't there. Sara was there. You couldn't remember why you were in the bar or what you had ordered. All you knew was that your glass was half-empty when you first noticed her. Her hair was black, streaked with th...

Butch's Bar Slut

by sissymissyct on Jan 7, 2020
BDSM

(A bit darker than most of my tales. It would fit in gay or nonconsent as well. Gay sex, sissy sex, chastity and punishment.) *** I love this bar, Butch thought to himself as he finished another beer. And why shouldn't he. It had everything a Leather Bear could want. Plenty of hot men in leather, and some women as well. A bunch of trans girls and some siss...

Tempting Father Hardy

by wistan on Jan 20, 2020
Transgender & Crossdressers

The following story contains scenes of a big-dicked trans girl having her way with a guy. It also contains strong religious elements, and could well be considered blasphemous by those who believe in such things. If you find either element offensive, this isn't the story for you and you shouldn't read it. Everyone in this story is over 18. ------------ "Of...

The Abdominal Snowman

by Cashmere_Snow on Jun 1, 2020
Sci-Fi & Fantasy

This is the second story in The Erotic Adventures of Chastity Summers. It follows Romancing the Raptor. ** Chauncey Adams started the day with a light breakfast of coffee and toast, explicitly avoiding any added sugar or cream or condiment that might irritate his bowels on such an important day, but, with each exhausted, stumbling step through the darkness...

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...

The Perfect Pair Pt. 02

by ChangeYourPassword on Jun 9, 2020
Fetish

The Perfect Pair Part 2 (fetish, chastity, consensual & non-consensual, cross dressing) By ChangeYourPassword Author's Note: This is a work of fiction. It is a story of sexual fantasies and fetishes. These sexual practices are not for everyone, but those of us who delve into them understand the allure. The characters in the story certainly do. If you...

Romancing the Raptor

by Cashmere_Snow on Sep 15, 2017
NonHuman

Tiffany. Maria. Sandy. Destiny. Chastity repeated the names to herself as she directed a coy smile at the man she had brought back to her apartment. Tiffany. Maria. Sandy. Destiny. They were the names of the women he had raped and then sent to the grave in one case and into the ICU with the others. They were women like her—women who shared an... affliction...

Ordeal in Elsewhere

by Wifetheif on Sep 16, 2017
Sci-Fi & Fantasy

William and I were on a more or less routine reconnaissance mission when it the incident occurred. If you are at all familiar with trans-dimensional travel most of the excursions are undertaken by people like William and myself, historians AND theoretical physicists. Truth be told I'm better at both of those skills than William but we make a great team, both...

Slow Descent into Sissy-Hood... Ch. 01

by Slipperylock on Oct 31, 2018
Transgender & Crossdressers

Beta boy beginnings. It started when I was online, lonely and drunk. I'd been at University for maybe three months at that point, struggling along with a Masters degree in Economics. Unlike my undergraduate years, I had decided to live alone in a one bedroom flat - I thought that with more privacy would come more focus. What I hadn't counted on was that wi...