Punishment Chastity Stories

36,108 results
Orientation
Length
Source
Infinite Scroll

Alexia Accumulates Punishment Ch. 02

by gab365 on Sep 14, 2017
BDSM

This is a continuation of Alexia Accumulates Punishment. It involves activities with bodily waste. Please do not continue reading if this is not your scene. ----- My butt hole hurt so much! The butt plug was not only stretching me sideways but inside as well. I had never had something so huge in me before. And the itching was insane! Sitting with my leg...

Infidelity and Chastity Ch. 07

by rockbohunk on Sep 15, 2017
BDSM

Rick and Sara took advantage of the warm sun and finished her photo shoot in the back yard. Sara playfully posed for Rick trying to get him excited. The only problem was, that she too was excited. After confronting her fear of being caught naked outside, Sara enjoyed being photographed hiding behind trees or modeling on the Harley. The warm seat felt good to...

A Slave's Journey Ch. 03 - New Recruits

by punishedone on Dec 10, 2019
BDSM

As the light from the door floods the room in blinding white light signaling Mistress return. Her voluptuous outline in the door frame as she eagerly approaches. I hear the clicking of her spiked heels as she steps. The door closes and my eyes are adjusting to see my Goddess in her attire for the evening. It is fairly warm in the room which prevents the nake...

The Vacation Pt. 02

by medic45 on Sep 19, 2017
BDSM

Chapter 2: Guess who's coming to dinner I greeted Shirley with a kiss as she extended the back of her hand towards me. This was my normal greeting as I waited for her kneeling in the entry way. My cock was locked in the chastity belt with a medium sized butt plug lodged in my ass. I was naked and my knees hurt from the prolonged period of kneeling. "Honey,...

A Different Kind of Home Ch. 03

by starmanz1 on Sep 16, 2017
BDSM

The following night, Thursday, I was not on service duty and so ate with everyone, but even though the conversation was pleasant, I did not seem to be learning anything new about what was going on in the house. After dessert I went to my room. A couple of hours later, Miss Becky walked in. After I kissed her feet, she had me stand up. With a look of disgust...

A Sissy's Uniform Pt. 01

by Deeznuts4pm on Sep 14, 2020
Transgender & Crossdressers

I suppose the best place to start here is what my life currently looks like. I'm a 25 year old chastity sissy maid that lives with my dom. I would tell you my name before I was a sissy, but there's little point, so the name we are going by here is Jessica. I've always had a skinny build, and this is well complemented by my dark brown hair, which after servin...

March Madness Ch. 08

by jbirdman on Sep 13, 2017
Transsexuals & Crossdressers

This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), teasing & denial, chastity training, mild bondage, creampies, cuckolding cross-dressing and a few other fantasies of mine. I hope you find it entertaining, but if you might be offe...

Star Wars - Partners in Sex - Bonus

by HandcuffGirl on Mar 17, 2020
Celebrities & Fan Fiction

Authoress's notes: The following is a bonus scene from my story Partners In Sex. Jedi Knight Ta'tan'ia has been partnered with Imperial Security Officer Lieutenant Stormie Kintra. Lt Kintra quickly begins domming the submissive Jedi when they aren't on missions. Star Wars: Partners In Sex Bonus Scene Ta'tan'ia was hanging upside down. Her legs were spread...

Chastity Debauched: Penitent

by MorganHawke on Sep 15, 2017
BDSM

In Which Chastity has an appointment with the Unholy Father... For Bear Part One: The Club “I can’t believe my Dad had me to come to his company pool party at the Club.” Chastity grumbled to herself while standing before the tall mirror completely nude. She stared into the mirror’s reflection of her deep violet eyes as she tied her waist-length, strawberr...

A Slave Trainer Ch. 01

by HisSexKitten0908 on Sep 26, 2017
BDSM

"Hurry, the new shipment will be here soon." I say indifferently. Amber, my dark haired beauty, kneels in front of me. She unzips my jeans with her teeth and licks up the side of my cock, sending shivers of pleasure through me. She sucks the bulbous head into her mouth, burying her face in my crotch. I groan as my dick hits the back of her throat. She sucks...