Sissy Chastity Cuck Stories

13,492 results
Orientation
Length
Source
Infinite Scroll

Sam's New Position Ch. 02

by worzel on Dec 11, 2018
Fetish

Sam woke with a start, She couldn't see, everything was black! Her arms were painfully pulled back, and tied like a strappardo but taking her weight. her legs weren't touching the ground, They were pulled apart by a spreader bar and tied off a few inches off the bed where Sam had been told to sit many hours before. The past week had been absolute hell for...

A Date with My Wife

by MisterEEE on Apr 17, 2019
Loving Wives

"Strip". I was shocked. Rarely did my wife look or talk like this. I had just come home from work to an unusually quiet house; the kids were nowhere to be seen or heard. They were probably out playing with friends. I wandered into the laundry room; empty. The kitchen and living room were equally quiet. I started down the hallway and noticed the bedroom light...

Be Careful with Your Cell Phone

by redwolf555 on Jun 19, 2019
Fetish

Steve was having a good day at the store that he managed. The store, a dollar discount store, was busy so time was moving along. A new employee had started last week and was doing very well. During a busy moment, Steve had set his cell phone down under the front counter to deal with a situation. Normally, Steve would never do that. There were things on the c...

Liz

by SEVERUSMAX on Jun 12, 2019
Interracial Love

I hadn't seen or heard from Liz in a good, long while, so running into her in the mall was a bit of a shock, given how much it was out of the blue. It was also a little jolt to see the engagement ring on her left hand, not that I resented her presumed marital bliss. I hadn't been invited to her wedding yet, but I would have been more shocked if I had. Old fl...

Katt's New Toy Ch. 01

by econut on Sep 11, 2018
BDSM

SMACK! Katt's hand came down swiftly, squarely hitting her target. A muffled wail emanated from beneath her buttocks as the body of her subject bucked, his legs spasming in front of her. Katt smiled and laughed openly. She was truly enjoying herself. Ostensibly, she was punishing her slave for cumming without permission, but truthfully, she just really like...

Better as Emmy Ch. 01-05

by cactusaur on Jun 8, 2020
Transgender & Crossdressers

Hi everyone! It's been a while since I've posted any new stories here, but a fan reached out for a continuation and cross-over of the Emmy's New Kinks and Better as Riley stories. This new story builds on the characters, themes, and storylines from Emmy's New Kinks and Better as Riley. I recommend reading those before diving in here. Themes: Feminization, t...

Jackie

by JimBob44 on Sep 13, 2017
Interracial Love

*Author's Note: Any and all persons engaging in any sexual act are at least eighteen years of age. * Chapter 1 Serena Lee slurped at the large chocolate malt. She wasn't really hungry, but Jackie insisted that she drink it. "You need to put some weight on you, girl," Jackie laughed as she affectionately popped her dishtowel at Serena's bony rump. Serena...

Twenty-One More Questions

by silkstockingslover on Jan 1, 2019
Reviews & Essays

Summary: Jasmine responds to the most frequent questions asked by readers. Thanks to: Tex Beethoven, Wayne, and Robert for editing this essay. This isn't really a sequel, although it's a second part, as it addresses questions I didn't answer in 2017's Twenty Questions. 21 More Questions After 2017's 20 Questions, I received many more questions. I have n...

Patti Cake Ch. 09

by betamale08 on Jul 17, 2019
Transgender & Crossdressers

Patti drove me home later that morning, we kissed some in my driveway and I could see Mom's curtains rustling as we said our good-byes. We kissed again and then I went into my half of the house I shared with Mom – and as I had in Patti's arms the night before in her big bed, I went in and I slept... I'd slept like I never before, 15yrs of wondering and thin...

Being Sarah

by Alex_Lockheed on Sep 25, 2017
Transsexuals & Crossdressers

Please note, this is a story about a male-to-female crossdresser. It includes themes of bisexuality, dominance/submission, embarrassing erections, anal play, cunnilingus and cum-eating. If you like that, awesome. If you don't maybe it's time to check another post. You can't say I haven't warned you ;) **** There are many difficult decisions I've had to ma...