Sissy Bet Stories

70,272 results
Orientation
Length
Source
Infinite Scroll

Sissy Sidney and Sister

by FemFreak on Apr 17, 2019
Transgender & Crossdressers

Summary: Sidney is reluctantly persuaded into submitting to Ellen's humiliating wishes. His sister is along for the ride and gets to humiliate him a bit as well. In the end, Sydney questions his identity. All characters are 18 or older. Tags include feminization, crossdressing, pegging, femdom, mff, incest. ~~~~~ Angie loved to bully her little brother Si...

Mistress In Control

by polishjoe on Sep 17, 2017
BDSM

Last Friday evening when I got home Mistress informed me that tonight was going to be a very hot night but I did not realize until later just how hot things were going to get. Mistress had dinner ready and she told me she wanted us to eat quickly so we could get straight to the "activities" she had planned. I thought it curious because Mistress usually did...

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...

Girl's Night Pt. 10

by DifferentBreed on Sep 14, 2017
Fetish

This story contains adult fetish themes between consenting adults that may be upsetting for some readers. There are also scenes with vulgar language that some may find offensive. Please proceed with caution. ~ thank you for your patience ~ The sleek black towncar maneuvered through the downtown streets, the darkly tinted windows giving no hint to the passe...

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...

Brandi's Turn Pt. 02

by 9volt on Mar 3, 2020
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** So we woke up with my sister looking, mouth agape, at my husband in his torn panties, garter belt stockings and bra and me with a 6-inch strapon cock jutting from my otherwise naked body. There wasn't even a blanket handy to pull over ourselves. There was a pretty awkward silence...

My First Visit

by gbr2004 on Jan 1, 2019
BDSM

This is fiction. Do not read if gay action and discipline aren't your thing. ***** I was nervous as I drove through Tucson on my way to meet a man I had met online. I saw his ad on Craigslist and he said he was into dominating other men. I emailed him telling him my interests in this but also told him about my lack of experience with other men. I had been...

The AA Men

by DrLuverotica on Sep 17, 2017
Loving Wives

"Jo, the car's broken down again...I'm going to try and get a push and get it restarted." I left my wife the voicemail message and went to back to my office. Carl and Don were still trying to sort out a glitch on the new website we'd been designing for a client. "Battery gone again?" Carl asked, barely looking up from the PC. "Yeah...Can you..." "Give...

Sissy

by rogue01 on Sep 19, 2017
Fetish

Sissy It happened at last that he was caught. His wife came home mid-afternoon with her friend Miriam and found him upstairs in the bedroom wearing a pair of her panties. Her reaction shocked him. In the hot instant of his overriding shame he was aghast to discover in her a persona he had not yet known existed. Him, a faintly domineering man, like so many...

The Training of Sissy Paula Ch. 5

by submissive~pet~ on Sep 14, 2017
Fetish

After the fuckings I had gotten from Max my asshole was so stretched, I had to wear diapers all the time. Mistress Carolyn used this to her advantage. She had a few men that liked sissy babies. The men would bring me all sorts of little sissy clothes. Dress me up and have me nurse their cocks as if they were bottles of milk. One day a new man showed up, he w...