Boarding School Stories

107,279 results
Orientation
Length
Source
Infinite Scroll

Hello, Old Friend

by bmalone on Sep 13, 2017
Erotic Couplings

"Hello, old friend." It's a line that had been used for years between Sarah and I. It allowed us to know, in the first seconds of a conversation, that we were still on good terms. In this case, it was the first conversation in two years between us. It was good to know that we were still good friends. Even though Sarah and I had dated in high school, the fa...

Cummuters! Ch. 02

by shireman on Aug 31, 2017
First Time

Cummuters! 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 mine at the beginning of term. I had been appointed his mentor, to show him around and generally help him to settle in, and over the next few weeks we got to know each other really well. One da...

My Life

by JamieeR on Sep 14, 2017
Novels and Novellas

It's raining again... or maybe it's better to say it's still raining. But at least the bed is warm and comfy, and looking at my watch, I still have an hour before I have to get up and get to class. My name is Jillian Aimee Boyack but everyone calls me Jamiee. I'm was cursed to be short and skinny at five-feet one-inch tall and weighing in at ninety-five poun...

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...

Introducing Susan

by 0131aj on Sep 13, 2017
First Time

Susan had never been happier. She was luxuriating on top of her new bed in her new bedroom. She had dreaded the end of High School and the return from boarding at her all girls' school. It wasn't that she had loved school so much; if anything she was a bit of a loner and hadn't made any really close friends. But the end of term, the end of her school years,...

Tables Turned Pt. 01

by LisaRowl on Mar 7, 2018
BDSM

Up until 6th period everything had been going well for Mr Ritz. He had found that his fellow teachers and his new pupils were all somehow refreshing to the fusty boarding college in Coventry where he had been an English teacher before. Here were American students and teachers with their fresh irreverence and lack of uniform or regulations. And Summer Heigh...

Emma's Endurance

by ladyredmuff on Sep 19, 2017
BDSM

Emma stood in the cool bedroom, shivering slightly and feeling more terrified than ever -- and this had been a day of quivering fear and mixed dread and anticipation. Three weeks earlier, she had been at her Catholic boarding school, finishing her 'A levels' and wondering if she would get the grades that she needed to study history of art and when she could...

Pam and My Virgin Plan

by Longstretch on Aug 18, 2017
First Time

"The bastard! The lying bastard! He told me he loved me, now he's fucking somebody else! The bastard!" Pam was standing in the doorway of my cabin. Since I knew her only by sight, I was mystified why she was sharing this confidence with me. "Hi, Pam. What happened?" "Mark's a bastard, a real bastard! He told me he loved me and I believed him!" She started...

Caller ID Ch. 01

by Kathi on Sep 17, 2017
Loving Wives

"There, that should do it!" Maggie finished and looked over the group of coaches and assistants gathered around her. Leaning back against her car she smiled and said, "Get your team members together and pass on the information they need to get the season started. I'm looking forward to working with y'all." She and the other coaches had just finished makin...

As God Intended Ch. 03

by stopeggo on Sep 19, 2017
Exhibitionist & Voyeur

Ch. 3: As God Intended We had finally arrived on the 50th floor. No one harassed us after the two blondes from the mall did. And once we got to the shower floor I finally got to masturbate! The actual hairdresser was just another teenager, and the actual haircut was just a buzz thing. We were not happy about it, but there wasn't really anything we could do....