Chastity Surprise Stories

139,463 results
Orientation
Length
Source
Infinite Scroll

Maria's Life of Slavery

by StrictDom on Sep 19, 2017
BDSM

Maria is an absolute goddess. Her hair is blond, styled in a sexy messy way, her eyes are a gorgeous blue, her nose is cute and wrinkles slightly when she smiles. Her lips are full and soft. We have been seeing each other for a few months now, and talked for ages before then on the internet, where we met. Maria is My slave, in every way imaginable. I literal...

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...

Family Chastity Story Ch. 02

by antares34 on Jul 3, 2019
BDSM

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+. ***** Having grown bored with how things were progressing with my sissy son, I have recently ventured into a new and fun project –filming and distribu...

Femdom's Ultimate Submission Ch. 01

by Goldfing on Sep 14, 2017
BDSM

Synopsis: Bill, who is still a virgin, has an internet pornography addiction that causes him to masturbate incessantly. He seeks help from a sex therapist, Dr Sharon Childress, who ends up taking advantage of his situation. * The work day is over. Bill enters his cluttered dark apartment and flops down to the computer screen. He clicks his favorite porn si...

Just Look at Me Now Ch. 05

by GFfan on Sep 14, 2020
Transgender & Crossdressers

ACT ONE: PARTY PREP "If the item is defective, you can return it for a full refund, but no, you cannot return it if it's simply too big. I'm sure you can understand why." This was the saleswoman's reply to the question I had been instructed to ask about an item Jude and Becky had assigned me to buy. "I doubt that will be a problem though," the clerk, Felic...

The Pantysissy Diaries Ch. 03

by JPantyboyVSL on Apr 23, 2019
Transgender & Crossdressers

This is a 3rd person fiction story about my fantasies of being a Pantysissy. All characters in this story are made up, and are all over the ages of 18. To better follow this story read The Pantysissy Diaries Chapters 1 and 2 before reading chapter 3. ***** It was nighttime in NYC, and Jaymie and her 6 Mistresses had just left their apartment to head to Vic...

SurpriseSurpriseSurprise

by summertide on Jan 15, 2019
BDSM

You are such a good sub. You do your best at what I tell you to do. You have such a magical tongue. Just thinking about it makes my body humm. Just having you, keeps me on my toes. I am always thinking of different things to do with you. The last thing I would ever want a you to say about me is that I am boring. God Forbid! I had put some nipple clamps and...

Faro's New Brother

by Gman26 on Sep 17, 2017
BDSM

If you're going to be critical just for the sake of being critical, don't say anything because I will flag you with the webmaster. Be constructive with your criticism. I welcome feedback. ***** Shopping day rolled around. For the first time Master was going to take it to town and "teach" it how to shop. It is as if Master forgot it was once free, shopping...

Star Wars Imperial Prostitute 2 Ch. 02

by HandcuffGirl on Sep 12, 2017
Celebrities & Fan Fiction

Authoress's notes: This story takes place approximately six months after the events of Imperial Prostitute SX-51472. In case you haven't read Imperial Prostitute SX-51472, I'll summarize it for you first: Star Wars: Imperial Prostitute SX-51472 Jaina Solo, mentally and physically exhausted from killing her twin brother, Darth Cadeus, accepts Jagged Fel's i...

Neighbours in the Time of COVID-19 Pt. 05

by Rondeevu on Oct 6, 2020
BDSM

Last episode In the last episode, I had gone over to Dianne's house for another afternoon of torture and torment - for her. In part 4 I had her tied to her bed and had already tortured her with nipple clamps on her pussy lips while massaging her and teasing her clit. I had removed the clamps from her labia and allowed her to relax before bringing out the v...