Chastity Teacher Stories

31,037 results
Orientation
Length
Source
Infinite Scroll

The Wedding Ch. 02

by betamale08 on Mar 31, 2020
Transgender & Crossdressers

The Wedding (Patti Cake Part 3) Chapter 2 -- Party in Pink Purgatory... "Oh Wow Dale! You look fantastic! Very -- Very pretty... I can hardly tell that you're my boy anymore! Really sweetie I'm so impressed -- and Patti you look gorgeous too... I knew that dress would look stunning on you -- but Dale -- my pretty -- pretty -- son... That dress is perfect;...

Buzzbomb

by Dar_Jisbo on Nov 11, 2019
BDSM

I had decided to take the job offer. Sure, it meant moving, but I was single, had lived alone for the past five years, and didn't have a lot of material possessions. The Benson School For Girls was less a school and more akin to a reformatory for rich female teenagers whose parents were at their wits' end. Think the Rejects School from the movie Toy Soldie...

Teacher's Pet

by MissSubmissive0861 on Dec 30, 2019
BDSM

I walk into my last class of the day. It's my final year of high school. I turned 18 my junior year as I entered school a year late. I'm the first one in the room so I walk over to the teacher, Mr. James, desk. I glance over to make sure nobody else has come in yet. "Good afternoon, Miss Lilian." "Good afternoon Master." "What's the matter, my pet?" He sa...

Mother-in-Law Discipline Pt. 03

by Chastebob on Sep 14, 2017
Fetish

When David returned home from his mother-in-law's it wasn't like the last time. Mary was waiting for him, but even if she had wanted sex he wasn't up to it. She put him to bed and applied cold packs to his battered organs. She coaxed the whole story out of him, how he came to require this punishment, the instrument she used, etc. Still emotional and 'broken'...

Obedience Training

by justincbenedict on Sep 17, 2017
BDSM

"How was Dubai?" asked Benny Price, as Nora made herself comfortable in his living room. Nora grinned. She'd been dating Benny for three months, ever since she'd met him at a singles mixer for dominant women and submissive men at the PainCafe. After their initial dates, Nora had put Benny in a chastity device. She pointed out to him that if he really liked...

Teased and Denied Ch. 06

by bighouselover on Sep 25, 2017
BDSM

Sunday morning arrived and I couldn't help but think back to what Miss Ashley had said about seeing me Sunday. I finally decided to ask my wife about it. When I did so, she responded with a very large and sexy grin. I was then told that she had promised Ashley that she could observe and possibly take part in my weekly milking. I blanched at the thought. I wo...

Marigold Tells the Truth

by justincbenedict on Sep 14, 2017
BDSM

In the Attic Spenlow thought of beautiful Marigold, and how she'd run her pale pink nails all over his cock as he'd been tied down. She'd be in one of her snug powder blue T-shirts, and licking her lips, tossing her long hair behind her shoulder, and he'd squirm, but be completely in her power. I'd started out with them fucking like rabbits, and then she'd...

The Last Flowers

by AutumnsBreath on May 30, 2018
NonHuman

AUTHOR NOTE: Hello, readers! This idea came from a dream, so it's a little bizarre. Sorry if this backstory chapter is boring and slightly disturbing. The story gets better later. They'll be freedom and sexy lesbian nymphs for all. My endings are always happy. -------- The north wind blew a chilling gust, laced with the remnants of winter. Sarielle hugged...

Letter from Coldstream Canyon

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: My cousin Glen is married to a dominant bitch called Jocelyn. When Glen and his brother Gavin, both free-wheeling, bimbo-chasing poker-playing drunkards met Jocelyn in a club, they had no idea that the icy blonde would tempt the two of them, and Glen's boss Monroe, into becoming her slave harem! Now Glen hasn't been out for a poker night...

Chastity is Punished

by AlinaX on Sep 12, 2017
Fetish

I've never really been into dominance and submission, and even bondage is something I've engaged with only reluctantly. I don't like handing control of my body over to someone else. The idea of wearing a chastity belt for the pleasure of some 'Master' - or 'Mistress', for that matter - and begging them to unlock the belt so that I can finally achieve a long-...