Gay Headmaster Stories

67 results
Orientation
Length
Source
Infinite Scroll

Bio of a Bully Ch. 3: Big Brother Pt. 2

by ozeboi69 on Sep 25, 2017
Gay Male

I knew I couldn't do nothing until I could breathe properly again, but it really fucking hurt to be pinned down by a dweeb like Scott and not be able to fight back. Scott was lying on top of me, his underweight fuckin' body rubbing against my tight, muscled bod and his matchstick fuckin' arms holding me there like I was nothing. The more I struggled, the h...

Homeward Bound Ch. 03

by sr71plt on Aug 30, 2017
Gay Male

I quickly found that my mother's "special services" operation paled in the face of what Mrs. Childress was capable of. I wasn't the only one on her staff giving extra attention for extra cash at the Swannanoa Boarding House. In addition to me for the men guests so inclined, she had two serving girls, Sadie and Clare, who did the same for the men who paid for...

Cummuters Pt. 02

by shiremantoo on Aug 30, 2017
Gay Male

Part Two: Stephen Stephen and I hadn't known each other for long: His parents had returned from abroad and he had transferred from his boarding school to my day school at the beginning of term. I had been appointed his mentor, to show him around and help him to settle in and over the next few weeks we got to know each other really well. One day, we had fini...

Halloween Party Hollow Weenies

by walterio on Nov 4, 2019
Gay Male

INVITATION Sitting across from Archibald Thompson, the private school's Headmaster, was Stanley Morrison, the school's largest benefactor. Stanley was having a Halloween costume party for his special clients. He needed five students to attend the party. "So, Stan, you are asking me to send five gay students to your home for a Halloween party." "That is c...

Glenn

by Pissdrinker on Apr 21, 2020
Gay Male

Please note that my partner and I always use condoms with others but I never include them or describe the act of putting them on in my true stories. Play safe guys. ***************************************** So we lived in France for 6 years or so and then moved back to the UK, and rather than head to London where we had been immediately before France, we c...

Blackmailed Into Homo-Humiliation

by TheDarkCloud on Sep 14, 2017
Gay Male

When I started with the company Roger was the top salesman, he had the best clients, the best bonus and the best company car. Within three months I had eclipsed him. It stood to reason, I was fifteen years younger than his forty, I was hungrier, I was more ambitious. I was just plain better than he was. He didn't like it and resented me and I knew he plotted...

Ben is Taught about Discipline

by verdunsears on Jan 23, 2019
Gay Male

"It's Ben Davis, right? From Professor Bolt's History class? I thought it was you." I turned at the sound of the voice behind me and was surprised to see Bill Hughes, a fellow student who I didn't think was aware of my existence. I said hello back, expecting him to walk past me, and was surprised when he slowed to my pace and began to chat. "You look like...

Puff Adder Pt. 03

by anaidmap on Aug 18, 2017
Gay Male

Gavin Tonight I was going to meet Jason's best friend, Anna. I've known him since I was five. He was one of my brother's closest friends, so he was at our place a lot when I was growing up. When I was eighteen I started having 'thoughts' about him, which eventually evolved into day dreams and then full-out wet dreams. His 6'1'', lightly tanned, lithe body...

The Cruise to Heaven and Hell

by marq_andrewx on Oct 6, 2020
Gay Male

Yeah well this is my story of what happened to us over the last few weeks but first some of my background. My name is Andrew, or Drew for short, though not many people call me that. I live in Sydney in Australia. I'm half Australian, of Irish descent, and half Japanese. I don't know who my father is. All my mum knows is that he was a Japanese businessman on...

The Liberation

by TheEnigmaticOne on Aug 30, 2017
Gay Male

*All characters and situations in this story are entirely fictional. Any similarity it may share with a real event is purely coincidence. Also, I would like to thank AngelLove on editing this story, as it was a very exceptional job.* * It was getting to be unbearable. Gregory Kaplan checked his watch to make sure the room's clock hadn't been deceiving him....