Headmistress Spanking Stories

23,089 results
Orientation
Length
Source
Infinite Scroll

The Bet Ch. 01

by MutableMalachi on Sep 15, 2017
BDSM

I sipped my drink, watching the action around me, and sighed. It seemed like watching was all I ever got to do. I was stuck in a catch-22: I wanted to find someone who could accept everything about me, but I wasn't willing to tell anyone anything about me until I was sure they'd accepted me. A gay BDSM club probably wasn't the best choice for having deep per...

Sweet Submission

by andromeda_enchained on Sep 11, 2017
BDSM

This is my first ever submission (so to speak) so please be gentle! Her heartbeat pounds out a familiar rhythm as she waits in the dark, stretched silently across the mattress like an offering, knowing he's on his way. The sensation of her pulse is primal. She's tried to fill the long desolate stretch of daylight hours, anticipation rising with the settin...

Bratty Natasha

by Jasmine27 on Dec 29, 2017
BDSM

Thanks to theMasterBaiter for editing this story! * Natasha was feeling bratty since morning, when Master had left way too quickly for work. He was in the middle of teasing her, slowly eating her out when his phone had rung! She was angry and frustrated. It had been 4 hours, and since she was not allowed to touch herself, she was frustrated and her panties...

Harry's New Teaching Method

by storyfella on Feb 13, 2018
Fetish

Harry was a maths teacher and taught at a high school. He had just turned sixty but he was young at heart. Just lately he'd been getting more and more irritated and found he was losing his patience with some of his pupils. It wasn't like him at all and he knew he needed to find a solution. Perhaps he'd been teaching too long. Should he find a different job?...

08h00 Appointment

by Kittenliz on Apr 3, 2019
BDSM

Lady Tiffany lazed back on her sofa, the soft silk of her robe folding gracefully over her bare body. The smoke of her cigarette entranced her, and the soft mellow music in the background filled her head. There was a knock on the door that adjoined her apartment with the rest of the house. She jumped slightly. "Come in," she barked, annoyed at the interrupt...

Head in Box... Pussy Exposed

by ellaalltiedup on Apr 9, 2019
BDSM

A thin layer of black silk laid over my eyes, and all that I could feel was the cool breeze surrounding my body like a rope, entering into my exposed pussy and ass, and against the bottom of my small feet. Although I could feel this wonderful breeze all over my body, I could not feel it on my face... well... that is because my head was tightly squeezed into...

Gagged Slut Needs

by ColorfulFun on Jan 1, 2019
BDSM

I have never been one to do a lot of online dating, but lately I've needed to really indulge in my kinky side, and oral domination is a huge part of it. Or rather, oral submission on my part. There's just something about oral control that keeps my pussy messier than a slip n slide, and I can't get satisfied gagging myself anymore. I need a man to do it to me...

Let Her Sound!

by trino692001 on Nov 24, 2017
BDSM

This is a 100% true story: I am a very lucky I have reconnected with a friend from high school thirty years later who is my sexual playmate. We have no commitment to each other outside of GREAT sexual adventures. I am very submissive and she is VERY adventurous and dominate. Our past includes bondage, spanking, strap on play, forced cum eating, and some min...

A Lesson in Good Behaviour

by delicatedarkness on Nov 26, 2017
BDSM

...and why doing as you're told is a good idea. I'd been bratty all day. I'd ducked and dived away from his warnings and gentle threats, just to frustrate him. It was only a game...wasn't it? In the summer sunshine, laid on soft grass, my mischievous smile and tongue between my teeth was enough to get away with bad behaviour for now. Surrounded by friends a...

Sharing The Puta Ch. 03

by MosheDovit on Dec 31, 2018
BDSM

Since Mexico she has me do little things to remind me that I am a trained cock slut now. I am milked twice a day to keep me accustomed to cumming on command. I am never allowed to wear underwear unless instructed, but she often makes me wear a snap-on cock ring underneath my clothes with ownership tags attached to it. I thought about that a lot more than not...