Inspection Headmaster Stories

12,642 results
Orientation
Length
Source
Infinite Scroll

Six of the Best

by KinoKe on Sep 17, 2017
BDSM

'Ah. Mrs Preston. Do come in.' The Headmaster rose slightly from behind his large desk but the late-afternoon light flooding in through the windows behind him made it difficult for Mrs Preston to see him properly. There was, however, no mistaking his rich authoritative voice. 'It's Dale, isn't it?' 'Delia,' Mrs Preston said. The Headmaster turned his he...

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...

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...

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...

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...

Six of the Best Ch. 02

by KinoKe on Sep 17, 2017
BDSM

It was a little after seven in the evening. The Headmaster was in his study, hunting and pecking at the keyboard that sat atop his large oak desk with its dark forest green inlaid leather top. Tap, tap, tap. Tap, tap, tap. And then, from the door opposite, almost an echo: Tap, tap, tap. 'Come!' The Headmaster called. The study door opened and Matron -- fif...

Journey of Submission

by msterrilynn on Sep 12, 2017
BDSM

Chapter 1: Phone Call The phone rang as she came in the door with her hands full of groceries. Amelia set them down and reached for the phone. "Hello?" she said. "You have been accepted into The Academy. A packet will soon arrive with instructions on how to proceed", a voice said. Amelia collapsed into a nearby chair and slowly smiled. She has been accepted...

Detention Pt. 02

by Croony on Sep 15, 2017
Fetish

Susie Johnson had a sip of her chilled white wine as she got ready for a night out with a couple of her friends. She'd finished her make up and had chosen her sexiest black underwear with black hold up stockings. She had decided to wear her favourite little black dress. She remembered the last time she wore it. She would never forget the day when she was rav...

New Punishment System Demonstration

by TUnicornLiterotica on Jun 15, 2020
Transgender & Crossdressers

DISCLAIMER: This story involves the degradation of a trans character, this is not meant to be read as transphobic scripture. The writer, being me, is trans, not that makes it automatically okay, but just understand, this is a fantasy, and it fulfills some of my submissive desires. Characters all 18 years old above etc. * * * * * Carla had just been pulled...

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...