Inspection Headmaster Stories

12,642 results
Orientation
Length
Source
Infinite Scroll

The Headmaster's Room Ch. 03

by Mag58 on Sep 12, 2017
Fetish

My story jumps forward 20 years to May of this year. In the intervening years I've been married twice, lived with two other guys and never had any children. My career, as it is, has consisted of a succession of dead-end shop and restaurant work; moving from town to town across the UK and a Summer in Ibiza. "Well, well, well...some people never change. Do t...

Class Rules Ch. 03

by 0131aj on Sep 17, 2017
Fetish

Shirley thought that the Headmaster would now agree to retaining both her husband, Julian, and herself in their teaching posts at the all girls school. She had allowed him to spank her over his lap, had held his large cock (much larger than Julian's) in her hand and had not tried to escape when he started to shoot his spunk all over her face. Julian had neve...

The Girls of St Catherine's Ch. 02

by nightvoice2 on Sep 25, 2017
Novels and Novellas

The Headmaster Ritual (2) Friday, 24 May Portia hunted through her drawers frantically. "Hey, have either of you taken any of my clothes?" she snapped, addressing the other two girls in her dorm. Tara and Lizzy both shook their heads as they got dressed. "Why, what's wrong?" Tara asked, a concerned look clouding her pretty face as she brushed her hair....

Finishing School For Ladies Ch. 01

by MicheleNylons on Sep 16, 2017
Transsexuals & Crossdressers

Chapter One -- The Beginning Valerie Swindon sat at her desk in her small study grading exam papers. A shadow fell over the opaque glass panel of the door and she looked up at the ornate mantle clock and realised it was time. She arose from her chair and came around to the front of her cluttered desk and unzipped her skirt. She caught it before it pooled...

Summer Ch. 15 Gwen's Story 3

by TheTyke on Sep 19, 2017
First Time

The affair quickly gathered pace. They met again the next day and within moments of arriving he was inside her; fingers, tongues, his penis, it didn't matter; he filled her to capacity and then some, they were insatiable. They made love throughout that first day; and the next and the next. She could not wait to be with him, the thought of his hands on her...

An Appropriate Punishment

by Frixmaster on Aug 31, 2017
Fetish

I'd just turned 18, and was heading into the final few months of my high school years. Then something happened that year that would change the rest of my life forever. School started like any other Friday: I caught up with the other guys, giving each other a hard time with whatever banter we could come up with, then trying to predict the weekend football r...

Yes, Headmaster

by Literalist on Sep 16, 2017
Letters & Transcripts

Transcript of Headmaster M*****'s Private Phone call 11/09/2009 1:26 AM (*ringing*) (*Phone is picked up*) Mr. M***** Hello, (Female Student) (Female Student) Why- hello, sir. Mr. M***** I understand you've been misbehaving in your classes again. (Female Student) Uh, yes, sir. I have. Mr. M***** That won't do, Ms. *****. You'll have to be discipl...

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...

Morgana's Painful Lesson Ch. 2

by Morganauk on Sep 16, 2017
BDSM

It was Friday afternoon and the last day of the school year. There was an expectant buzz in the air, as everyone's thoughts were concentrated on tonight's leaving party. Morgana was as excited as everyone else – she had big plans for tonight. Headmaster Dave had kindly agreed to hold the yearly event in his large country house. Only the older pupils were in...

Taught a Lesson

by goodnight_sweetheart on Sep 12, 2017
BDSM

The cold December rain was beating hard on the classroom windows. Amber watched it run down the glass; she liked the rain but wished it wasn't accompanied by the chilling wind. The school's heating wasn't working again, so all the halls and classrooms were freezing. Amber glanced over at Dru, her best friend whom she also shared a room with, Dru smiled sligh...