Sissy Punishment Stories

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Orientation
Length
Source
Infinite Scroll

Cassy's Game Ch. 1

by wormwood on Sep 19, 2017
BDSM

copyright2001. by: Wormwood My name is Jason, I'm a thirty two year old machinist, married to a wonderful woman. Her name is Cassandra but everyone calls her Cassy. Everyone but me that is. You see I'm a panty slave, cuckolded, slut, whored out husband that is only allowed to call my sweet wife Mistress Cassandra. I'm only allowed to wear... Well, we'll get...

Futanari Ballbusting: Rich

by RichardPercival on Sep 16, 2017
BDSM

Breaking the fourth wall here, yesterday I had all four of my wisdom teeth removed and I'm a tad loopy from the pain killers. I'm stuck in my house and decided this is a good way to kill time, sorry if the quality of the story is not that great. ***** I think small cocks are easily the best. They're just so easy to fit in your hand, most futas with small p...

Not at Mardygrass

by potsherd22 on Sep 16, 2017
Sci-Fi & Fantasy

It would be pointless to deny my debt to Aldous Huxley's Brave New World and George Orwell's 1984 I also appropriated a powerful and disturbing theme from Kazuo Ishiguro's Never let me Go. I hope that there is sufficient that is original to justify putting this flimsy story out there. Thank you Colin the dogg for reading this story and giving support and ad...

The Dutch Master Ch. 06

by suboots on Mar 6, 2018
BDSM

I was quickly discovering that the management of pain was something that can only be done inside the head. The serrated jaws of the clover leaf nipple clamps latched on tenaciously to the little nodules of flesh, creating an intense, if very localised agony, out of all proportion to their size. I tried various coping strategies but ultimately what it came do...

Bonnie Lavigne Ch. 02 - Learning

by Amerigarkeiner on Mar 28, 2018
BDSM

-Authors note; following this Chapter is easier after reading Chapter 1. ***** Bonnie pushed out as if she was about to take a dump as He was pushing the butt plug in. After she felt her asshole beginning to expand from the plug, she relaxed. As it was sliding in, she noticed it was bigger than the one He normally used - and harder. She could not imagine w...

Tea Time

by Hercules_unleashed on Sep 17, 2017
BDSM

Naked, Rosa stood in the marble and stainless steel kitchen brewing tea. Beyond the panoramic window, across the divide, that long ago may or may not have been a river servicing the town, but now separated her property from the modern six storey car park opposite, she saw the slightest of movements in the shadows. Still facing the window, for effect, she st...

Bound to Love Each Other

by MrDeviant on Sep 13, 2017
BDSM

I suppose it had something to do with the fact that I am a cop, but somehow every woman I met seemed to think I was into bondage. It must be the cuffs, the uniform, and the billy club. I guess they all scream, "He's kinky. He loves bondage." Well, in my case, though not all cops are into it, they would be right. My current lady love is another cop. She is a...

Date Night

by hidden_darkness on May 14, 2018
BDSM

Carol's long black hair shimmered in the streetlight as she and her husband, Andy, stepped out of their car and walked to the front door. They were nearing the end of another typical date night. Andy slipped off his shoes and lumbered over to the closet to hang up his jacket, loosening his tie as he went. Carol sauntered up the stairs to the bedroom, her shi...

Blackmailed at First Ch. 05

by TheKeith on Nov 29, 2017
Loving Wives

I woke my ex-wife from her emotion-drained sleep, and got her dressed (she said) with an outfit from her packed bag. That outfit was just a typical little black dress. Front-zip. Very short skirt. Fully lined, so she didn't need to wear bra or panties ... unless, of course, she bent over, in which case her legs, butt and vagina were on display. Pretty little...

He Learns about Miriam's Discipline

by susangreenway on May 29, 2018
BDSM

After I'd been married for only a year, I sensed that I was constantly complaining about my husband's behavior. Where I tended to keep my things, especially clothing, neat and orderly, Brad threw his dirty laundry all over the place and seemed to have assumed that someone would pick up after him. He also criticized me if I didn't get home before he did in ti...