Headmaster Punishment Bdsm Stories

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Orientation
Length
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Infinite Scroll

Curing the Groper

by MelanieK on Sep 16, 2017
BDSM

At the time all this happened I was in the upper sixth form and in my last year at school. I got on well with all my fellow students and, being 18, I’d had quite a bit of experience with a number of the girls. I knew how to get a girl interested. A Few compliments about her good looks and figure and she was putty in my hands. As I was elected head boy I supp...

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...

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...

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...

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...

My Best Friend Emily Ch. 05

by FerdGerfel on Sep 26, 2017
Group Sex

Welcome to chapter five of this ongoing story. I have always tried to make my stories an exploration of sexuality, but I think this chapter takes things to a whole new level. There is a lot of straight sex, but there is also messy play, voyeurism, BDSM/role playing, and anal. Hopefully everybody can find something they like about this story. As always, any s...

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...

Return of Grady

by egmontgrigor2010 on Sep 16, 2017
Romance

CHAPTER 1 Like thousands of expensively educated youngsters before him and destined to tread a similar path after him, Grady Halliburton was totally undistinguished in his passage through Ascension Boarding School for Boys, New Hampshire. His marks ran consistently at C-level with the occasional B and D to inject variety and in sport he was designated 'wate...

RWBY auction

by dragonsage on Nov 18, 2017
BDSM

Headmaster Ozpin was in a bit of a difficult situation. Thanks to the after effects of the breach the city of vale had to spend large amounts of Lien to repair for the damages. Because of the amount of money spent it would be quite difficult to properly prepare for the Vytal festival. If he could not find a new source of money he may have to cancel the festi...

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Caitlyn and Professor

by Pink_Maggie on Sep 12, 2017
BDSM

Walking from her car to her professor's house Caitlyn was seized by a feeling of foreboding. She considered going home at that moment and later replying to his original email that, although she was terribly sorry, there'd been an emergency and could they please reschedule? But, God, that email. Although it did not allude to what the meeting concerned its mes...