Headmistress Spanking Stories

23,089 results
Orientation
Length
Source
Infinite Scroll

Give Me What I Need...

by wetandwhat on Jan 15, 2019
Erotic Couplings

I flounced into the kitchen giving my hips just enough swish to flare out the pleats on my extremely short shirt. I tugged the tails of my button down shirt covering another inch of my mid rift, but exposing said amount more of my cleavage. He was there, still in work clothes. His mind probably still hung up on all those petty office things. I smirked as I...

Pornstar Joclyn Stone Does Anal!

by Samuelx on Dec 12, 2018
Celebrities & Fan Fiction

Joclyn Stone is one of the top starlets of the Adult Film Industry today. A beautiful, curvy and clear-eyed blonde woman with the kind of nicely rounded booty that even Black women would envy. She has carved out a niche for herself by working in everything from interracial porn movies to fetish films and MILF-type flicks. Always her amazing sensuality and se...

Double Crack Jack

by Alluring_Crimson_Shifter on Sep 24, 2019
Anal

Jack, Brenda, and Juan were friends. One Friday evening they went clubbing together, had a great time, and got drunk. They danced and partied until closing time. As they walked out Juan said, "Why don't we go to my apartment?" "Yes," they all chimed in. While Jack drove, Juan and Brenda made out in the back seat, kissing and playing. They arrived at Juan...

Shuttercuck Ch. 01

by LePelerin100 on Sep 24, 2019
Erotic Couplings

If Mei was nervous answering the door, she didn't show it. She was conventionally elegant and composed but for the thin, black dog collar around her neck. It was very obviously a dog collar and there was always the chance that it wasn't who we were expecting - her friend, Candy, at the door. "Wow. Look at you!" said Candy, holding Mei at arm's length, afte...

After Hours

by SirGalahad71 on Jul 2, 2019
Erotic Couplings

It was almost one in the morning when I returned to work. The last people finish their shift at 11:00 PM and then with shutting stuff down and turning things off the final person probably leaves by about 11:30 PM. The Security guard wonders around for another half hour before they too leave. So at 1:00 AM my workplace was deserted. I swiped my badge and quie...

Ladies of the Tower Ch. 02

by Arthur_Guy on Jul 3, 2019
Sci-Fi & Fantasy

Chapter-2: In Service to a Wizard The wizard was correct. Even though they had yet to receive their first job, they were being "generously compensated." There new employer went on that night to explain the terms and conditions of their contract: First, they would receive a weekly stipend whether that had anything to do, or not. Next, the got a base of oper...

Kate's Journey 08b: 3 in a Dungeon

by alexromana1997 on Jul 17, 2019
BDSM

In the morning, Kate felt a tad guilty about blowing off the workshop so fully. She talked with Michael who graciously agreed to drop her off for today's sessions. Things winded down at about 4:00 pm and she and Michael would have ample time for love later that day. Driving down the hill from the house in that luxurious Rolls Royce was a thrilling way to s...

Mr. Donovan and His Sitter

by PrettieKittie on Jul 15, 2019
Romance

Lily My hand shakes as I bring it up to ring the bell. Once I take it off the button I shake it out to help release some of the nervous energy flowing through my limbs. A loud thumping sounds from inside. Next comes a deep voice making monster 'roars' followed by some childish shrieks of excitement. I can't stop the smile that breaks loose even through the...

100 Centimetres - Experience 13

by icefantasygirl on Jun 25, 2019
BDSM

Authors Note: Teasing is like a story. I hope you enjoy this one my love. Ice ~ I was dreaming. Dreaming of the most passionate, pleasurable sex. After our shower experience last night, it had sent my body into a state of absolute want and need to be taken by you over and over again. When I awaken, I see that you aren't laying next to me. I could hear t...

Principal Reveals Students Need

by LetoSlave on Aug 21, 2019
BDSM

I was being called into the Principles office, and it wasn't even a school day for me. We were headed to an away game and I had stopped to pick up my spare phone from my locker. I kept a pay-as-you-go phone that my parents didn't know about, and when I picked it up it had a message from Principle Mason to come to his office immediately. The message was time...