High School Cuckold Stories

209,968 results
Orientation
Length
Source
Infinite Scroll

The Monday Night Glee Club

by MarkCane on Sep 17, 2017
BDSM

Michael Scott walked into the Fealty and Firkin for the first time in twenty years. It had been a popular haunt for the younger generation in the old days. Now Michael looked around him disapprovingly - the old place had changed so much. The saloon bar, taproom and the snug had all been knocked together into one large room. Nice carpets, shiny chrome, plush...

The Video Diary

by eddievalquez on Sep 11, 2017
Exhibitionist & Voyeur

Author's Note: These are the same two main characters from A Tale of Two Sisters. This story takes place several months later, and, again, is based on true events. ***** Kim had started another semester of school, and I was working at a movie store. With just six classes to go, I'd decided to take a break from my English Lit degree. Me and Kim had discusse...

Muslim Lesbians Of Boston

by Samuelx on Sep 16, 2017
Interracial Love

Sometimes goodbye's the only way, Beyza Ataturk told herself as she deleted her ex-girlfriend Manal Ismail from her Facebook. Tearfully the young woman got up and walked out of the computer terminal on the topmost floor of the Boston Public Library on Copley. Sighing deeply, she walked out of the library and walked a few blocks to Commonwealth Avenue, and wa...

If You Wish Upon a Star Pt. 01

by MyNameMayBeLucas on Sep 12, 2017
Toys & Masturbation

"Alexis! It's your stop!" Alexis snapped out of the daze she was in to find that the bus had finally arrived at her house. She exited, and watched as the bus slowly drove off into the distance. "Finally!" she said to herself as she turned to check the mailbox. Not even bothering to read what was addressed inside, Alexis grabbed the stack of envelopes and...

Amy Caught in the Middle

by mrhmann on Aug 30, 2017
Group Sex

It all started when Amy was given her student teaching assignment at the local high school. Everything started out safely enough, with new students coming in for band classes. The teacher, Mr. Kay, was in his mid 40's, slightly graying and married. Amy was apprehensive at first but soon warmed up to the daily routine of teaching high school students. Mr. K...

A Year Of First Times Ch. 01

by Theeeeee1 on Sep 13, 2017
First Time

1969 – A Year of First Times Part 1 1969 did not promise to be a memorable year when it was ushered in on January 1st, but I was wrong. I would begin dating Victoria (I call her Torrie.) for a second time in early spring, graduate from high school in June, start college in September and become engaged at Christmas. The year is most memorable for me because...

The Rising

by bloodtalon on Mar 19, 2007
Erotic Couplings

It has been a long time. You anxiously squirm in your seat, trying hard to think about things that do not pertain to sex, but it's no use. As your teacher drones on, it only becomes harder and harder to keep your eyes off of the people that you call friends. If they knew just how much you were hurting to bend them over the nearest desk and fuck them raw, you...

Open in Reader

Lady of the Manor

by Adrian69702006 on Jan 28, 2020
Fetish

(This is a newly written story which I intend to share elsewhere. I hope you enjoy it.) *** Lady Ann Heathcote-Gibson reached for the cafetière and poured herself another cup of freshly ground Colombian. Apart from a G & T in the evening before dinner, it was the one little indulgence she allowed herself. Breakfasting in the drawing room of Welford Ferry M...

Ann: A Love Story Ch. 10

by mimaster on Sep 14, 2017
Erotic Couplings

I should have been tired when I woke up. It had been another late night, and I had gotten very little sleep. But I woke up feeling refreshed and alive. My first thought was of Ann. I was excited about her being at Matt's and getting a chance to talk to her. I was more excited that she had seemed to be interested enough in me to openly flirt. And I was ecstat...

Cum Dumpster Finds Her Way Pt. 03

by DoxyTrainer on Sep 19, 2017
Sci-Fi & Fantasy

So... I never got over the things that happened to me in high school. I never moved on with my life. I existed. I allowed myself to live in the moments of my greatest humiliation. I lived tied up in that van where they pissed on me, lived in that pool of filth. I don't know if I've really lived anywhere else since, until Gordon and Dick Bigsuit came into my...