Punishment Chastity Stories

36,108 results
Orientation
Length
Source
Infinite Scroll

A Virgin locked in Chastity

by ronron1818 on Mar 3, 2020
Fetish

I was 18 when I moved in with Ruth. Ruth was my new land lady, I moved in with her for my university studies time frame. She had a big house and leased a room. Ruth was 56, in great shape, she was about 170 cm tall and about 50 kg with small breasts and a very nice figure. I was very excited to move, I loved the idea of sharing a house with a woman. I imag...

Her Butler Pt. 03

by patannon on Sep 14, 2020
BDSM

The next few years were very happy ones for him. His job meaningless, his great passion Miss Kendall's home. She set goals for his health, sending him to a personal trainer three evenings a week. He took additional cooking classes, especially baking and pastry. His whole life revolved around hers. Every evening he looked forward to the moment she walked thro...

Vacation Expectation

by IPleaseYouTease on Oct 6, 2020
Fetish

The wife's side of a conversation with her husband as she gets packed to go on a 10-day vacation with her lover and leave him behind. ~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~ "Okay Dearie. Up on the bed. It's almost time for me to leave. I have a plane to catch. Don't you worry. I know that once you're done binding your hands and fee...

My Secret Revealed Ch. 03

by jealouscuck on Mar 28, 2018
Transsexuals & Crossdressers

I was wondering what Karen had in store for me. When I got up the next morning, showered and shaved, I had little time to wait. She was holding her tiny g-string that she had worn the day before. A certain twinkle in her eye told me that something else was about to happen. "Honey," she said, "Like I told you last night, even with your smaller than average c...

Under Law of Arnell

by justincbenedict on Jun 19, 2018
BDSM

In the Burgundy Exercise Room, Esther, one among forty naked and perspiring calisthenticists, swung her arms up, gasping. She didn't want to get Master Specs's attention. How a weird little fuck like him worked for Mistress Arnell, Esther would never know. "Feet together, shoulders back, hands in front of your chest, Jumping Jacks let's go!" And they b...

Danni Ch. 02

by Coder3445 on Jan 20, 2020
Transgender & Crossdressers

This story starts where the last left off, read Danni to understand what is going on in this story. Of course all character are above the age of 18. The following story contain feminization and female domination. * Also another description Tara, Danni's Mother Unlike Danni Tara had tanned skin, she was five foot four inches tall. She had green eyes and...

Mistress Chronicles Ch. 03

by MistressMtoyou on Sep 25, 2017
Fetish

Title: Decision time Background/update Even if you've been following the last couple of stories about my subject, Muffin, you might want to read this background as there are a few new points of note. Muffin is slightly heavyset, 36 years old, about 5' 7" and 160 pounds. He is quite submissive and seems to be aroused by a number of fetishes, but he professe...

Reformatory Girls Ch. 13

by escalus on Sep 26, 2017
Fetish

It is with some relief that Miss McCloud steps out into Miss Lucy's Consulting Room. For an hour and a half she has been standing in the cramped confines of the lavatory cubicle. Through a pair of strategically-placed toiled rolls she has been peering out of the small window: nothing that has been said or done in the Consulting Room has escaped her. Yet sti...

My Sissy Life

by snorn on Nov 26, 2017
Transsexuals & Crossdressers

I love being a sissy. I have been in permanent chastity since 27 Sep 2016, and am loving it. I have sissy training rules that are focused on keeping me doing the household chores and training me to be rented out as a cheap sissy whore/maid, a list of sissy motivational sayings which I listen to on repeat whilst doing nightly chores, and service rules for th...

Platonic Chastity Ch. 03

by Cagedcompliance14 on Sep 21, 2020
BDSM

Platonic Chastity Chapter 3 Taylor was a bit stiff in several regards when he awoke the following morning. He was confused for a second as his grogginess caused him to forget that he spent the night with Jacci's tights tied around his eyes. A quick waft confirmed that her scent remained on the garments and caused his cage to tighten even further. As a res...