Sissy Pimp Stories

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Spanking Night Ch. 07

by Angelscuck on Sep 14, 2017
BDSM

The shower felt good against my freshly shaven skin. I was covered with cum, urine and pussy juice. I knew if I took too long, I would be punished by my wife and mistress so I cut it short. After towel drying, I put on a clean pair of my wife's panties and hurried down stairs. "Well, here's our little sissy bitch now. It took you long enough!" Mistress Sh...

Pimped Out Sissy Bitch

by Gemsissy on Jan 12, 2018
Fetish

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit. I glanced at the phone....

Snap! to it Divina

by DivinaTellsAll on Feb 12, 2019
BDSM

Writer's note: The following story is 100% true THE DRIVE The drive to Austin was 8 hours in good weather. Today it had been raining, and it was going to be 11 hours in the car, by arrival time. I was acutely aware of how long the car ride had been so far, for several reasons. The biggest of which was the overly-tight pair of pink sissy panties, curren...

Pimped Out White Sissy!

by nancyvasquez on Sep 16, 2017
Anal

Hi everyone! I haven't posted in a while, but I definitely have been having a lot of experiences. Best news is that I found a new adult bookstore to hang out in! I found out about if from a guy who I gave a blow job to in SECRETS in Jack London Square in Oakland. He asked me if I'd ever been there, and I told him I'd never even heard of it. It's a place call...

Making of a Sissy Whore Ch. 03

by SecretAgentFun on Oct 21, 2019
Loving Wives

Pimped Out If you haven't read the first 2 chapters, it might be a good idea so that this makes more sense. Your call, and I hope you enjoy either way! *** Jeff stepped off the bus feeling defeated as he walked the five blocks back to Brad and Kayla's place. He couldn't even think of it as home now, since Kayla was sure to kick him out tomorrow. He was jo...

Sissy Keven Jeanne Bardot

by nancyvasquez on Sep 14, 2017
Erotic Couplings

After Jinky and I had been married about a year, she began to make gay references about me being gay. When I'd get mad, she'd laugh and say, "I'm only joking!" I remember she always used to squeeze my breasts, which were quite prominent, and say, "Wow, sweetie, nice development!" And then she'd laugh. My feminine breasts had been a source of embarrassment f...

Sissy Shopping

by Candour on Sep 25, 2017
BDSM

My first story, finally edited and tidied up. I hope you enjoy it, I enjoyed writing it. --------- You were standing in your local department store in the make up section, looking for foundation. Not too sure what you are doing, and must have looked a little lost as one of the sales girls came up quietly behind you. She was a delightfully pretty 18 year ol...

Sissy for a Day

by silkstockingslover on Oct 16, 2018
Fetish

Summary: With his wife's help and support, a man becomes a sissy for black cock. Note 1: This is a Halloween 2018 Contest Story. Be warned: this story involves sissy sex, obsession over black cock and a bukkake. If this isn't your thing, please don't read any further. Note 2: This is dedicated to the real Paul who requested this story. Note 3: Thanks to:...

White Gurl Pimped in the Hood

by Stephisissycd on Sep 11, 2017
Group Sex

After Black Mike made me his bitch, showing up at motels all over town dressed like a street hooker, he sent me a text one day. "Hey bitch. I need you to dress really slutty, get smooth and totally clean, and meet me at the motel at 6th and Los Angeles st." I knew where that was, right by skid row. My pussy started to throb thinking about what black mike h...

A Sissy Saga Ch. 19

by Snurge on Sep 15, 2017
Novels and Novellas

It came as a surprise. When Abigail received a message from his sister telling him to go to her room he was astonished. He never went into the family apartments until recess, so such a demand was abnormal. Bossy bitch, Abigail thought as he made his way there, but he didn't say it. His relationship with his sister had never been one of close kinship, they'd...