Headmistress Spanking Stories

23,089 results
Orientation
Length
Source
Infinite Scroll

The Babysitter Ch. 04

by snaillover69 on Sep 11, 2017
First Time

Sue called Becky and told her to come over at 7:00, and tell your Dad that we need you to spend the night because we won't be home until very late. Becky explained to her Dad that she was heading over to the Summers house to babysit, and that they needed her to spend the night, they weren't going to get home until about 2:00 in the morning. Her Dad said a...

Helen, Roger, & Me Ch. 3

by Dudley on Sep 17, 2017
BDSM

Pt. III: The Party Around 7 o'clock I heard cars begin to arrive, I counted three but I couldn't guess how many were in each car. There was much laughing and giggling as the evening progressed, I could hear them goading each other on to try on the various pieces of lingerie. After about an hour the tempo of the noises began to increase as I heard Helen ca...

Bad Girl

by kotori on Sep 12, 2017
BDSM

As she stood at the kitchen sink washing up the tea things, Thomas approached form behind and put it arms around her, gently nuzzling her neck. "Please!" she said with some agitation, "can't you see I've got to finish up here?" Thomas stiffened, surprised at her rebuke of his affections. His arms fell slack and he stepped back. "There's no need to take...

Candle Play

by CheeseCake4u on Sep 19, 2017
BDSM

Foreword: A short story about a couples BDSM session, involving hair pulling, spanking, and candle play. I wrote this story after reading an "Oh Joy, Sex Toy" Guest comic about candle play, which I couldn't get out of my head afterwards. I am not native to the English language so there might be some issues, especially with punctuation. I hope you enjoy....

Black Women are Goddesses Ch. 20

by Samuelx on Sep 11, 2017
Group Sex

My name is Cody Johnson. I'm a big and tall young Black man living in Champion City, Massachusetts. I'm a student at Sanders College, a historically Black private school. It's the setting of this brother's adventures. I'm captain of the Men's intercollegiate Football team, and a man in my position is quite popular on campus. And that's part of the problem. E...

Rachel's Dilemma Ch. 3

by bondmaster on Sep 12, 2017
BDSM

This is the continuing story of my luscious girlfriend's bizarre deal with her ex-husband. In a nutshell, he would pay her one million dollars if she allowed me to punish and torture her for a year. He provided all the props, instructed me on what to do and each session was videotaped so he could verify it was done. If you haven't already done so, you really...

Being My Wife's Bff Ch. 00: Prologue

by MyUncensoredSelf on Sep 13, 2017
Transsexuals & Crossdressers

When I walked in my wife was sound asleep in the bed. The covers had come off her and she was only wearing a pair of underpants because of the heat. I stared at her for a while, her large breasts hanging down, her shoulder length red hair falling across her face, her big butt. She was so sexy, I wanted her ... but my cock wouldn't stir. It's an issue I have...

My Life With Liana

by MasterJekyll on Sep 17, 2017
BDSM

This is a continuation from my first story My Taking of Liana. That was the first time I ever had any of my writings displayed for public viewing. The feedback I received was something I had never known before and I do appreciate all who did give me feedback, and all who voted on my story. My Life With Liana I woke up, the smell of breakfast filling my sen...

Master's Christmas Treat

by rawsilk on Sep 17, 2017
BDSM

There is a sensual pleasure in doing nothing, lying naked, warming the leather of an old Chesterfield sofa. An intermission in life, time for the mind to drift and muse. The click of the lock turning, brings me out of my reverie, giving the motivation to rise swiftly from the sofa. Standing, hands behind my neck, head down, eyes lowered, legs apart. Long a...

TSTC01: Cum Shy to Cum Slut

by IndigoCrow on Sep 19, 2017
Fetish

The Slut Training ClinicCh. 01 Lucy ran a delicate hand over one of her gigantic tits, stroking the soft, smooth flesh with her fingertips. She sighed audibly as her fingers traced a circle gently around one nipple, then reached in and tweaked it hard. She bit her bright red bottom lip as she felt a familiar throbbing between her thighs. The basement was fi...