Headmaster Punishment Stories

31,842 results
Orientation
Length
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Infinite Scroll

Naughty School Girl Ch. 02

by Maddisyn on Sep 9, 2019
Erotic Couplings

Report to the Headmaster! In her previous story about Doctor Love's Practice, Natalie shared her concerns about her naughty school girl fantasies and her initial counselling. The charming Doctor Love's proposal of sexual therapy was too tempting for the young teacher. Natalie returns for a follow-up session to fulfil her fantasies and discovers more Practic...

Cane and Cock

by AnnGoode on Sep 17, 2017
BDSM

Lady Dawn was born into a family of wealth and influence. One of the families that had three centuries ago formed a secret society to preserve their status. Only male members of the families could join. In the year 1703 they set out the principles by which they and future generations would continue to prosper. Today those same families having endured wars an...

The University Slave Club Ch. 01

by MD171133 on Apr 13, 2020
BDSM

The University Slave Club of Willow University is the first club on campus that authorized sexual activities and public nudity. Emma was a freshman at Willow University, just starting college. As the first few weeks go by and the semester settled down a little, the university announced the university club fair, which will occur in three days. Emma was su...

The Headmaster and the Pupil

by irisheyesgirl on Sep 12, 2017
BDSM

The characters in this story are consenting adults. St. Ann's School exists in the imagination of two creative lovers. If you enjoyed reading these characters as much as I enjoyed writing them, please leave suggestions for what you'd like to see them up to next! ***** -The Headmaster- "WHAT am I going to do with you, Miss Connolly?" I sighed heavily as I...

Mrs. White Gets Promoted

by mikey5001 on Sep 17, 2017
Group Sex

At 3:40 pm Mrs. Carol White began the walk from her mobile classroom down to the headmaster's office. She was going to be interviewed for the newly vacated position of the head of the English department. It was between her and Mrs. Cox. Secretly she knew she had the disadvantage. Mrs. Cox had been teaching for ten years long than her, and the head of the Eng...

Heather & Mrs. Harley Ch. 02

by UBU on Sep 14, 2017
BDSM

When I got up the next morning it all seemed unreal, as if what had happened with Mrs. Harley the night before really had been just a nightmare. I couldn’t quite convince myself of it though, and distractedly sleepwalked through my first day of senior year, avoiding Heather and only seeing Mrs. Harley from a distance, as she swept into her classroom with a q...

Token of Appreciation

by LOAnnie2 on Sep 13, 2017
Fetish

"Finally, happy eighteenth birthday to Jason Jones and Valerie Arians. Have a wonderful day Albright Academy." Ashleigh Miller lifted her hand from the mic cue and sighed. She took a step back and walked over to the table holding twin bingo machines that sat in the corner of the school office. Kneeling down, she opened the cabinet tucked underneath and pulle...

A Visit to the Gym

by djt_one on Sep 17, 2017
BDSM

It took two weeks for the cane marks on Sue's behind to fade. This was not surprising after what had taken place in the headmasters study at the school reunion. Not only had Sue been soundly thrashed, she had also been thoroughly fucked by her old headmaster. All of which had happened while John, her husband had looked on, and at some stages taken part. Ther...

Kitty's After-School Special

by goodgrrl107 on Sep 19, 2017
Group Sex

All characters are 18 years of age or older. This is a work of fiction and any similarity to real live events is purely coincidental. Please—enjoy my fantasy, and as this is my first submission, I'd welcome any feedback. ***************************************************** My parents are out of town for the weekend and apparently do not trust me to handle...

What makes a demon

by Beziel on Jan 20, 2020
Sci-Fi & Fantasy

She was starving. She thought of conjuring food, but she didn't want to be seen using magic. Not in the cells. Not heading to the death row. She believed she could still redeem herself. One way or another. She was shivering. It was a bit past midnight and her clothes were torn. She attempted to cover herself more, but it only revealed another hole in the s...