High School Cuckold Stories

209,968 results
Orientation
Length
Source
Infinite Scroll

New Job and a New Life Pt. 01

by venchier on Jul 14, 2020
Interracial Love

Haven't written in a while. I hope you'll enjoy this rather incredible IR cuckold tale. When my wife went black for the first time ten years ago, it was almost as good as it gets, but not as good as the story you're about to read. If you're wondering, I did play high school football and scored a few TD's. ___________________ "Brad, your twenty-fifth high s...

Marriage of Convenience

by CuckoldGuy on Oct 14, 2017
Reviews & Essays

Within the human mind there is what I call, for lack of a better word, the inner circle. This is where we store all of our fantasies, fetishes, hidden desires, passions, fears and secrets. I'm sure there is a technical word for it but I refer to it as the inner circle. When two people fall in love they begin very cautiously to share their inner circle with...

Wet Hot Summer

by cphi on Jun 9, 2018
Erotic Couplings

Note to the reader: Game mode is really required for this story. I CANNOT STRESS THAT ENOUGH. There are whole blocks of dialogue in some scenes that just won't appear if you don't have the scoring active. The flowchart is going to be as complicated as i can manage, and the hidden variables will determine what paths and scenes will be available to you, based...

Open in Reader

Black Cuckolding 101

by Samuelx on Sep 11, 2017
Fetish

Welcome to the world of Black Cuckold Couples, my name is Kia Haywood-Albright and I'll be your guide. When you think of cuckolding, I bet you automatically envision a White couple, a Black guy with a big dick and a scenario involving the Black dude fucking the White chick while her White hubby watched the whole thing unfold. Well, it's not always that way....

Chicken Race

by Winterfrog on Sep 17, 2017
Loving Wives

Many thanks to Techsan for editing this story. * It was a busy Saturday at the supermarket in our small Scandinavian town. Short of parking spaces at the supermarket as usual when my wife and I went there to shop. I did as usual; instead of driving around and searching, I stopped my Toyota Rav4 in a strategic place and when a space became empty, I usually...

Infertility

by CuckoldGuy on Sep 14, 2017
Loving Wives

A true cuckold story. My name is Karen and I want to share with you my short love story. When I was dating, I had three steady boyfriends, Nelson,Tony and Jimmy. It was two years after I graduated high school that I started dating Tony. He is a tall, muscular, handsome guy and all of my girlfriends would have died to go out with him. On our first date he...

Born to be a Cuckold

by W_MA_DWM on Sep 11, 2017
Fetish

This story starts off slow, however it does lead into some very explicit sexual scenes. So be patient -- it gets hotter. It all began over twenty years ago when I met Lizabeth, the girl who became my wife. I had no idea what Mother Nature's plan was for me in those early years. I did realize that I was different than the other boys and felt that I neve...

The Creation of Suzy Slut & Her Cuckold Ch. 02

by AlDevine on Aug 31, 2017
Group Sex

This is a sequel to the story "The Creation of Suzy Slut and Her Cuckold". The same disclaimers apply. You must read that story first, or this one will make no sense to you. Life Goes On: After we created Suzy Slut and Cuckold Bob at the initiation and the reconciliation dinner the following week, there were still relationships to work on. We would be see...

All In

by LunarSirius on Sep 17, 2017
Loving Wives

If you find cuckolding offensive I suggest that you skip to the last page, leave your caustic comment and avoid the pain of reading this story. If you want to read about a cock in a cage this isn't the story for you either. My story isn't for everyone, but you would be surprised by how many people find it oddly compelling. It's like a slow-motion catastrophe...

Handjob Ch. 08

by CuckoldGuy on Sep 15, 2017
Loving Wives

When I was engaged to be married, my mother told me that no one wants a single girl but once she becomes a married woman then she becomes very desirable. All of the men want a woman who is experienced and safe. By safe I mean if a single girl becomes pregnant then it's the man's problem but if a married woman becomes pregnant, it's her problem and the man...