High School Cuckold Stories

209,968 results
Orientation
Length
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Infinite Scroll

Dariya

by Cole Calder on Sep 14, 2017
Erotic Couplings

NB: This is a further story on from “Alison” and “Ann” I was coming off an excessively shit day. Ann was feeling sick, having been down with the flu for the last few days. I was really hoping she’d get better, not just because she was about my best friend, but because I wanted my closest fuck-buddy back in action as soon as possible. I couldn’t feel angry a...

Catherine Ch. 24

by switchhitter46 on Mar 9, 2020
Erotic Couplings

I live for the moment I hear that catch in her throat with our first kiss. Her breathing getting heavier with each tender touch and caress of her sensitive places, I wait for those three words she will not say..., yet. Catherine - Chapter 24 Confessions - Sally & Ryan - Besties "Good morning John," as I'm catching up to him a short distance from the subwa...

Torn

by komrad1156 on Sep 13, 2017
Mature

*Note to readers. I recently found myself looking through my high school year book for the first time in several years. As I always do, I remember with great fondness my beautiful, former English teacher, a married woman with whom I had a rather lengthy affair my senior year. Teacher-student affairs aren't common, but they certainly aren't rare by any means....

An Awakening in Valentine 01-02

by Koba on Jul 15, 2020
Non-Erotic

Preface This is a story about a trip I took in March 2020. For many reasons, I consider it the most exciting vacation I have ever been on. Every day was busy from early morning to late at night. I got to visit places such as the Grand Canyon and Zion National Park that I had wanted to see my entire life. It was a joy to finally experience these natural wond...

Lara and the Produce Queen

by ms_4tune on Jul 10, 2018
Erotic Couplings

Lara always knew her childhood wasn't typical. Single mothers raise lots of kids so that wasn't what made it different. Neglect is a harsh word. Rather it was the general ambivalence or presumption of independence on the part of her mother. Lara never knew her father and as she got older she realized her mother did not know him either. More than likely Lara...

Is This Turning Me On? Pt. 01

by NCER on Sep 16, 2017
Exhibitionist & Voyeur

This is my first submission, all characters are over 18. Ashley is based on a real person, and all events in this particular story are as well. I hope you enjoy. Part 1: Ashley Goes to a Costume Party Chapter 1: Rushed into it all. You have no idea how many times I've heard the lust filled words of "I fucking hate you." as I do something incredibly darin...

Mothers and Daughters Ch. 02

by Bodington on Sep 19, 2017
Novels and Novellas

As Ruth Williams and Vera Starikovich reached Chicago they were greeted by Jasmine, Ruth's oldest sister, at the bus station. After introductions were made, Jasmine had no objection to taking Vera back to the Williams home on Excalibur Street; after all Ruth was the owner and Jasmine had her own place. Vera's personality soon won Jasmine over and when Vera w...

The Bad Cop Ch. 03

by Seahawk76 on Aug 31, 2017
Exhibitionist & Voyeur

I'd just settled in and was sipping on my morning coffee when a shadow crossed my desk. I looked up and saw Tess Henderson, the owner of the advertising agency I worked for, standing over me. "Hi Laurie. I was wondering if you had a couple of minutes for a chat in my office." "Um, sure Mrs. Henderson." Butterflies were flapping around in my stomach as I lef...

Little Sister

by Bruno1027 on Sep 19, 2017
First Time

Candace's eighteenth birthday was next week and her old sister, Angie, was concerned. She knew her sex life had just begun and she was worried about the inevitable fumbles, disappointing quick draws and date rapes she'd encounter with the boys in her school. She had gone through that period herself and she didn't want her beloved sister to suffer the way she...

New Year, Old Friends

by randallangdon on Sep 12, 2017
Erotic Couplings

Sandra picked up Kelly at eight on New Year's Eve. It had been the fourth time they hung out during their holiday break from college. The two had been linked at the hip during high school but going to two separate colleges made that impossible. The time they spent together reminded them of how close their friendship was and how much they enjoyed each other's...