Sissy Punishment Stories

36,576 results
Orientation
Length
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Infinite Scroll

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...

Submitting to the Neighbour Lady

by Stillherer on Jun 8, 2020
BDSM

I went to high school with the Post twins in the late 60's. Tommy and Belinda Post. The Post twins were new to our area and it was rumoured that their father wasn't with them. It was our senior year and being 18 we just wanted it over with so we could get on with being adults. Belinda never gave me a second look but before he knew better Tommy struck up a te...

A Sissy's Uniform Pt. 01

by Deeznuts4pm on Sep 14, 2020
Transgender & Crossdressers

I suppose the best place to start here is what my life currently looks like. I'm a 25 year old chastity sissy maid that lives with my dom. I would tell you my name before I was a sissy, but there's little point, so the name we are going by here is Jessica. I've always had a skinny build, and this is well complemented by my dark brown hair, which after servin...

The Awakening of a Sissy Pt. 11

by sissyjolie4u on Jul 13, 2020
Transgender & Crossdressers

We had been driving in silence for about 10 minutes, with me reflecting on the changes to my home and the 2 men I was going to be meeting. I was both excited and nervous about meeting with Roy and Ronald. Mistress Di broke my thoughts stating "I think Nikki has done an excellent job with her house transformation work, don't you agree Jolie?" I looked over a...

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...

Alex to Alexis Ch. 01

by TransPrincessMorgan on Sep 25, 2017
Transsexuals & Crossdressers

Thanks to Jack Murphy for being our volunteer editor! Enjoy! ***** Chapter 1: Feminization Alex was late home again. Once, maybe twice would have been acceptable, but this was the third time this month. His mother, Daniella didn't know what to do with him, especially considering her other children, the eldest, Hannah, who was 25, and the youngest, Amelia,...

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...

Candi is a Sissy Cam Girl Ch. 01

by CandiCumminz on Jan 15, 2019
Transgender & Crossdressers

This is the 6'th story in Candi's tale. Please read the Candi's conversion series and Candi Gets an Upgrade for the full picture of what's happened so far. - Hi! My name is Candi Cumminz and I'm your new favourite bimbo sex-doll. My camera's always on and I'm always horny so stop by any time for a good time! I love dressing up for my fans and putting o...

Becoming a Sissy Maid & Slut Vol. 14

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Twenty Three: Sissies at Work, Sissies as Sluts at the Farm. 4:00am and the alarm clock goes off. We three sissies must wake and begin our day of long, hard labour of degrading sissy maid and sissy slut work. Off comes our sleeping lingerie and soon three naked with only our chastity devices dangling on our sissy dicks we must quickly and together s...

Neighbourhood Terror to Sissy Pt. 13

by Fibaro on Oct 7, 2019
Transgender & Crossdressers

Chapter 15 Only 10 minutes had passed since they left from the homeless shelter and they were already pulling up in front of CC's. Mark had had no time to process the humiliation he just experienced yet while he was already getting confronted by a whole new sense of dread creeping up to him. He knew Lisa meant well, but he was also sure she would get corrup...