Sissy Punishment Stories

36,576 results
Orientation
Length
Source
Infinite Scroll

Shared Punishment Ch. 01

by hatefulmoon on Sep 17, 2017
BDSM

I feel the weight of the bed shift as you slowly climb out of bed, trying not to wake me up. I roll onto my side and watch you in silence as you slip on a pair of pants. I climb out of bed once you leave the room and slip on my robe. I can hear you in the kitchen as I step out of the room and I smile to myself. I slowly creep up behind you while your attenti...

Villa in Spain

by VanessaEvans on Sep 16, 2017
Exhibitionist & Voyeur

Jon's bought a little villa in Spain and I've just been there for the first time. Jon took me there for a few days then left me there for week on my own. It was great, and I'm really looking forward to spending more time there. As usual Jon surprised me by coming home and telling me to put a few essentials into a bag and us leaving within a few minutes. A...

Mistress Barbara Ch. 16

by Barbara on Sep 15, 2017
Exhibitionist & Voyeur

Kurt wanted to put a proposal that seemed to excite him to Kent, so he came with us, partly to watch the new format and to talk business with his old friend. He was mysterious about the exact nature of his proposal. It was frustrating but because we were running late and there wasn't time to press him further. My natural curiosity was heightened when I saw a...

Deleted Scenes: Spiderman 2 #2

by MasterOkime on Sep 16, 2017
Celebrities & Fan Fiction

Deleted Scenes #2 Sorry for the long wait, but back by popular demand another Deleted Scene from the movie Spiderman 2, thank you everyone for the wonderful feedback. You don’t need to read the first one to understand this one but the first isn’t a bad story if I say so myself. I hope you enjoy the story also, don’t hesitate to vote. The organs blared out...

Part 02: Pet's Week After

by petsMissJenn on Sep 16, 2017
BDSM

Over the next few days Miss Jenn plans how to punish the two of them for their misbehaving. She has noticed that pet has become very attentive to her needs, more so than usual. From making sure her coffee is ready in the morning to cooking supper each night. A few days later, Miss Jenn finally decides how to punish her two men for teasing her. It is Wednes...

CD Asst. Secy. Ch. 01: End and Start

by cdtycoon on Apr 22, 2020
Transgender & Crossdressers

All the characters in the story are above 18 years of age. INTERNSHIP ENDS HERE On Monday; 9th December, as usual, I woke up at 5:00 a.m. as it had become my routine even though my alarm is still set for 5:30 a.m. anyway I got up and took a nice cold bath from head to toe and came out wearing towel at my chest. Then I went to get dressed in my white drive...

Hailey's Slutty Spanking

by nadia603000 on Jun 9, 2020
BDSM

Hailey's a pretty woman, too. She's 5'7" and thin at 129 pounds. She has short hair, a very dark brown, but dyed platinum-blond, that comes down just to the bottom of her jaw. Her eyes are blue, almost gray. And she has a fairly wide mouth with full, but light pink, lips. I know she has great curves and breasts, too, but with her almost-baggy blouse, there's...

The Flight Attendant

by Tendachocolate on Oct 8, 2019
Romance

The Flight Attendant I looked into the mirror to make sure everything was perfect. Making sure that my uniform looked clean and crisp with no wrinkles. That my badge was sitting up straight on the outskirts of my jacket pocket. My dark brown hair pulled back into a tight bun so that my uniform hat sat securely on top of my head. The only makeup that was a...

Erin Ch. 04: Domestic Discipline

by Graves94 on Sep 24, 2019
BDSM

Erin Ch. 04: Domestic Discipline By Graves94 {Note: This is the fourth in a multi-part story series involving a woman who provides leadership and discipline for her husband. Each installment can stand alone, but to start at the beginning, go to: Erin-1 - Female led Relationship. JQGraves} ******** "My hubby is a very sweet man," Erin said. "He recogn...

Spanked until Slim!

by GenevieveHarte on Apr 6, 2020
BDSM

Pulling her smock top down over her ever-expanding hips and tummy, Lucy sighed. The three months she had just spent working in America had added to her already substantial bulk. She took a last glance in the mirror before heading off to meet her friends for lunch, feeling self-conscious about her weight. Cancelling wasn't an option: it had been four months...