Sissy Penis Punishment Stories Stories

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Infinite Scroll

The White Slave

by mspbottom4black on Oct 6, 2020
Interracial Love

Editor's Note: this submission contains raceplay and femdom content. * Not long ago it was a straight and stuffy white male. it was arrogant and self-satisfied with its white male social and economic leverage and advantages. In the rat-race of white society it suppressed its submissive white side. But from time to time it would slip into daydreams of hav...

Jolene's Momma Pt. 01

by ValoryG on Jul 27, 2020
Transgender & Crossdressers

(The names and locations in this story are completely fictional and have no connection with any person living or dead.) My name's Chris. Wife Jolene and I have been married six years now. Live in the small city of Centertown, Ohio. It probably got that name because it's about half way between Columbus and Cincinnati. Being from a midwestern small town, the...

Mistress X 02: Pixie's Predicament

by Long2bLocked on Jan 22, 2019
BDSM

Note to readers: This short story is not part of any series. The setting and characters are based on those from my "Laura's Femdom" stories. My Mistress X stories stand on their own but are best read in order. This particular story describes a predicament bondage session. ***** Mistress Alexis X has a female live in slave named Pixie. She works at Red Ro...

Behavior Modification Institute Ch. 04

by NancyPan on Sep 12, 2017
Fetish

I received some very negative and very aggressive comments about previous chapter postings. If you are not aroused by FemDom, Humiliation, and Forced Fem please do not bother to read this. These stories are for the benefit of those who enjoy this form of erotica. ***** I lost all concept of time as I fell into a rhythm of incredible stimulation to my penis...

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...

High School Dilemma Ch. 05

by LaurenWestley on Sep 15, 2017
Fetish

(Authoress's note: of course all disclaimers are still in place regarding characters etc. PLEASE DON'T READ THIS IS YOU HAVE AN AVERSION TO PEE SCENES AND EXTREME HUMILIATION. This is only a fantasy story XXX+. I only wish there is enough here to make each of you happy. To those who have given me constructive criticisms as well as those with praise thanks. L...

Jasmin wears the pants Ch. 02

by Gretatv on Sep 13, 2017
Transsexuals & Crossdressers

In Part 1 of "Jasmin wears the pants" our hero is fascinated by a woman and in the end of the chapter he is waiting in front of her door just wearing his briefs. Thank you very much for all the positive feedback. I really appreciate the praise. Once again people who don't like TG stories and or are under aged shouldn't read on. All rights are reserved. If so...

Aunt Pamela and Leslie Ch. 02

by fantaseeboy on Jun 25, 2019
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** The days passed incredibly slowly after my meeting with Aunt Pamela. She dominated my dreams and fantasies. She often crossed my mind while in class and I would wind up with an erection and squirming in my seat with the memory of the spanking she'd given me and the reward I'd earn...

A Sissy Saga Ch. 06

by Snurge on Sep 15, 2017
Novels and Novellas

The following day was Sunday. Margaret Pardoe never resented being duty-tutor on a Sunday, it was the only day of the week without any kind of formal lessons and she was only responsible for overseeing the pantywaists when they strolled outside in the grounds. That said, much of the time she could idle away in the headmistress's study in pretence of monitori...

Neighbourhood Terror to Sissy Pt. 05

by Fibaro on Apr 3, 2019
Transgender & Crossdressers

At least he didn't have to wait long for his bus to pull up. Not that it helped with any of his suffering. He vowed right there that he would never visit that store again. There were few people on the bus and yet he felt like all eyes were on him. Passing two girls his age at front he heard some whispers. "What the fuck, I never thought that store would ever...