Sissy Maid Chastity Stories

25,197 results
Orientation
Length
Source
Infinite Scroll

The Vault Pt. 03

by undherfoot on Sep 18, 2017
BDSM

After Tiffany left, I went and dropped down on my couch. I don't know exactly how long I sat there because I was in a bit of a stupor. When the shock finally wore off, my mind began to race. I was upset at Tiffany. I needed to get out of this thing. Can I get it off myself? That's it! I'll cut the damn thing off! I live in an apartment and so I don't have a...

My Big Day

by shaveverything on Sep 17, 2017
Fetish

I met Kim in high school and have been attracted to her ever since. She knew how much I liked her but she never gave me the chance. She liked teasing me. Now, five years later, I'm her sex slave. It started a few months ago with daily chat sessions. These consisted of me jerking off while she watched. Sometimes she'd let me cum, sometimes she'd deny me my o...

Jason Gets Paddled

by Lilee on Sep 16, 2017
BDSM

Jason lay with his fingers laced behind his head. His hair was still slightly damp from his bath, and his body was tired from the day’s labor. He felt good, stronger then he’d ever been. The last few months had proved more trying then he would have guessed. He rose before dawn every morning and was constantly busy all the day long. Cleaning was a large part...

Coed Turned Housewife Ch. 06

by Maisy_P on Oct 8, 2019
Fetish

Coed Turned Housewife, Ch. 6 - "The Big Talk" The sixth in a series about innocent Chelsea Pelham and her handsome professor, Dr. Mark Benning. *** Still naked and covered in sexual fluids in Dr. Benning's office - his office hours not even yet fully completed - Chelsea and her professor lover recovered for a half hour or so, snuggling as best they could...

Stranded Pt. 03

by Diana Retnuhvek on Jan 20, 2020
Exhibitionist & Voyeur

Chapter 10 Jake sped away. He wanted to get home before Bonnie and make it as though he had never left the house. When she arrived back, she greeted him with a beaming smile and a long, lovely kiss. "Wow," he replied in surprise. "I'm back, babe," she said, as if returning from a whole other universe. They went on kissing for several minutes. "How...

Taking the Lad out of Alladin Ch. 12

by CaseyHeart on Dec 30, 2019
Transgender & Crossdressers

"Not good enough!" There was a slap on my ass, then the guy behind me repeated himself. "Give me an oink, Piggy." Fuuuuuuuck. Everyone was a theater critic all of a sudden. I was bound to a bench, face-down, eating the pussy of someone who called herself Mistress Kate. Everyone was watching me, and I couldn't wait to get fucked in the ass and earn a pig tai...

The Hooker Becomes Your Wife

by RottenPines on Mar 17, 2020
BDSM

Script Description: He's been paying a hooker to dominate him in seedy hotel rooms for weeks now, but tonight, she wants to punish him in his own home. He give her his address, and she's shocked to find out he lives in a fucking mansion! At first, it's business as usual as she bends him over her knee and spanks him before tying him to the bed, but things so...

Lena's Surprise

by Angelpenpal on Jul 13, 2020
Transgender & Crossdressers

I rolled over in bed, temporarily escaping Lena's grasp. I stretched out, yawning before collapsing back into my comfortable position as little spoon. This comfort wasn't foreign to me. In fact, I had become comfortable in just about every way with Lena since I had met her. It all started by breaking my comfort zone completely. I had been afraid to be in lo...

Petzoned

by CuckFantasy69 on Jul 13, 2020
Exhibitionist & Voyeur

The following events are fiction on my part with the help of my crush. Although we are not together she is aware of me writing this and knows all of my depraved fantasies...well, most of them at least. She will read this series and all of your feedback too. ***DISCLAIMER*** This series will heavily involve cuckolding, humiliation, crying, chastity torture...

The Spirit of Lady Macbeth Pt. 08

by alyssawinters on Oct 19, 2020
Transgender & Crossdressers

Feeling helpless yet pretty the shorter Olivia sat between Wanda and Lori still holding the two smallish pompoms. Glad to be back at their house Olivia had an apprehensive smile on his face as he tugged trying to pull the hem of the cheerleading skirt down a little more. It had taken time yet he adjusted to being a cheerleader with the four genetic females a...