Maid Chastity Stories

20,460 results
Orientation
Length
Source
Infinite Scroll

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,...

The Backpack

by ~Etoile~ on Jul 31, 2011
Fetish

Moving to a new place is always rough, but it can be rewarding as well. The Nuwisha Design College in Seaside City is a smallish school, but is known for its art and design classes. A lot of literature and word-of-mouth shows that graduates from this school often get very lucrative and popular jobs. Lucky for you, you were able to get in with some of your gr...

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Costume Store

by Zekar on Nov 23, 2016
Fantasy

The Costume Store is an indiscreet shop in the mall. Few people paid it any mind and many walked passed it without giving it a second glance. If they knew what wonders were inside they might have given more thought to going inside. Inside the shop walls were racks and racks of costumes. But not just any costumes. There were costumes that turned the wearer in...

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Mr Stephensons Fucking Machine 02

by MustafaFuch on Sep 17, 2017
BDSM

Before the Victorian Era safe sex meant kissing and a chastity belt, but when the key broke in Fanny's lock it took an engineer of Stephenson's stature to resolve the problem. "Thee done champion job of Fucking Machine for the missus so if thee can spare time I got another job for thee, bit delicate like." Young George Stephenson sat in the kitchen at Arth...

Maid Anna

by randomspaces on Sep 14, 2017
BDSM

Authors Note: I wrote this as an icebreaker on a dating website, it's the first story I've ever written with the intention of showing to someone else. Any reviews would be more than welcome. Oh, this should probably go without saying but not only is everyone in this story over 18, they also live in a wonderous fantasy land where pregnancies are always expect...

Seven Lessons Ch. 02

by Vertex on Sep 16, 2017
Transsexuals & Crossdressers

Previously... Bryan is an arrogant biggot. This Halloween season, someone has decided to teach him a series of 7 lessons. Yesterday the lesson was acceptance, but as he chose not to accept the lesson, he ended up with no body hair, wearing a bodystocking and being fitted with a chastity device. Will he learn his remaining lessons? That night he had many...

Mandy's Reward

by sissymaidrose on Sep 12, 2017
Transsexuals & Crossdressers

There was a sharp, heavy rap at the door. Mandy scrambled out of bed as Mistress Charlotte pushed the door open, hastily smoothing the tiny, soft, pink and green nightdress that barely went past her hips and surreptitiously tugged the matching knickers down from where they had ridden up into her bottom. As Mistress sashayed past to the throne like chair in t...

Helping Jess Pt. 05

by mski on Sep 25, 2017
BDSM

I slept well that Sunday night which surprised me, though I guess I was probably exhausted. I woke up with my normal hard-on a bit before 5am, well it would have been a hard-on but for the cage. My penis was certainly trying. I never found it an uncomfortable feeling, just frustrating that there is no ending and I could not jerk off, and now who knew what wa...

Adventure with a Couple

by kristendixon79 on Sep 17, 2017
BDSM

A friend of mine, who thinks that i lead an exciting sex life (okay, i DO, lol) has asked me to relate an incident from my experience where i had a session with a couple. So, R, here goes. i guess i should relate a bit about myself, so that you understand how this affair took place. i am a 41 year old professional woman. i live in a D/s relationship with m...

Chastity Ch. 02

by wishfulthinking on Sep 18, 2017
Romance

Kinlee woke with a glorious smile, her arms slowly stretching. Snuggling deeper beneath the blankets, her mind drifted. Suddenly, she sat up in the enormous bed, one hand holding the sheet to her bare breasts. Her mane tumbled in disarray around her shoulders in a golden halo. Rising panic flooded her. He couldn't have. He wouldn't have. Kinlee forced he...