Headmaster Punishment Bdsm Stories

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The Caring Headmaster...

by JOHNKEY2222 on Mar 13, 2018
BDSM

"Oh Alan, this stuffy old school gives me the creeps." said Dorothy to her handsome Husband, the new school master of the dreaded upper sixth. Alan agreed with his beautiful young Wife, "it is a bit old fashioned Dorothy, rigidly maintaining the 'traditional' school values, as everyone keeps endlessly repeating." They were alone now in the school master's...

Mary Carson's Punishment

by Lissette on Sep 17, 2017
BDSM

Mary Carson walked slowly down the empty halls of the girls' boarding school she attended. Most of the students had already returned to the dormitory for the evening to enjoy their evening meal and to complete their nightly homework. Mary, however, was headed to Headmaster Finch's office and she had a pretty good idea why. The Hutchens School for girls was...

The Headmaster

by amethyst wind on Sep 17, 2017
BDSM

I wanted to say thank you to the One that helped me write and get this ready for submission, ~smiles~ You know who you are. As always feel free to vote and send feedback, its always appreciated. ************* CRACK Standing behind her desk Mary Elizabeth watches as the girls turn around in their desks looking for the source of the noise. Nodding to them...

Joys Private Education Ch. 02

by fredricka on Sep 13, 2017
BDSM

Joy left the Headmaster's office, her mind in turmoil. Her ass still stung from the spankings, her pussy was still wet from the Headmaster's strong fingers, her nipples still hard and erect. She also remembered the Headmaster's hard on in his pants and the pain on his face as he was obviously in need of relief. Surely he enjoyed it? But why did he quit? May...

Joys Private Education Ch. 03

by fredricka on Sep 13, 2017
BDSM

At her dorm Joy lay on her bed thinking about the afternoon. She smiled at the pleasure that she derived from the Headmaster. Joy knew that Miss Kneed was playing with herself. This gave Joy an immense deal of pleasure. She was sure that she wanted to have the attention of Headmaster. Perhaps, Joy thought, this would be just the thing to make Miss Kneed a pe...

Joys Private Education Ch. 01

by fredricka on Sep 13, 2017
BDSM

She knew she should not have been cheating; she would not have had to except that Bobby had kept her out late last night. They were getting pretty heavy into petting and her mind just forgot about the test. Damn Miss Knead had it out for her, she did not know why but now Miss Kneed had got her. She was sent to the principal's office. Slowly she entered the...

Morgana's Painful Lesson

by Morganauk on Sep 16, 2017
BDSM

Morgana stood outside the Headmaster's office, nervously holding the note in her hand. She didn't know the contents of the note, only that it was about her and that she was in some sort of trouble. At 18 years old she already had a woman's figure and somehow looked out of place wearing the compulsory school uniform. She was short with blonde hair and blue...

Class Rules Ch. 02

by 0131aj on Sep 17, 2017
BDSM

One afternoon during the following week, Mr Gallagher was casually looking out of his window onto the lush green lawns below his study and saw something that took his eye. He rang his bell and his faithful secretary Miss O'Hare entered his room quietly. "You called me Head Master?" The Head nodded. "I have just seen Mrs West crossing the lawn from the gymna...

Mercedes Senior Year at St. Vincent

by OTKTop on Sep 17, 2017
BDSM

Mercedes senior year at St. Vincent Boarding school ***** When she was younger, Mercedes went to a very strict boarding school, one that still allowed corporal punishment. Usually the punishment was used sparingly but with a new Headmaster, Dr. Hoffman, more and more of the young women of St. Vincent Boarding School were ending up in the Headmaster's offic...

Sex School: Induction

by vixenoftheNorth on Sep 17, 2017
BDSM

Tori applied one last coat of bright red lipstick to her lips before stepping out of her parked car and crunching up the gravel pathway towards the imposing stone porch of the old school house. Her 6 inch platform heels sunk slightly with each step, and the gentle breeze sent a shiver round her toned thighs, which were barely covered by the short micro bodyc...