High School Cuckold Stories

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Being Mentored on How to Live Again

by bnaylor987 on Mar 26, 2019
Mature

How tough can life be for a blonde girl who was the top of her class academically, was twice an all state volleyball champion who also received a full ride to college, and had a loving family? It wasn't bad, it was great... Until my sophomore year of college when my parents were taken away by some drunk-assed delivery driver who worked for a major retail ch...

The Valedictorian

by darrion on Sep 13, 2017
Erotic Couplings

I had been a teacher at a private religious school for several years, ever since I had completed my PhD at the University of Michigan. For the most part my family thought that I was making a terrible mistake teaching in an academy, essentially a high school environment, with a doctorate in a field that would allow me to command five digit salaries elsewhere....

The Smell and Taste of Emily's Ass Ch. 01

by ChezK on Oct 30, 2018
Fetish

I had first become interested in ass licking and subsequently ass worship because of Emily. In high school, the topic had come up. Emily had said that while going down on her, someone had licked her butt. What's more, she had enjoyed it. Initially, I was disgusted, but the more I thought about the act, the more I became curious about it. After reading about...

The Yellow Book Fantasies Ch. 08

by TheChadDupree on Oct 15, 2018
Exhibitionist & Voyeur

2009... "So, how do you like your senior year, Chad Dupree?" she said to me with that pretty smile of hers. As much as I was excited, I was also kind of nervous. It was my last year of high school. "Are you going to miss me, Chad?" she said. "A little bit," I said to her. She was my first high school crush. She was one of the first girls I set my eyes on...

A Friend Helps Out

by hotwifejulie on Sep 17, 2017
Loving Wives

Back when my husband first began to hint that he might like me to have sex with other men, I must say I was a little confused by it. I had been brought up to assume that being married meant that I would never be able to consider such things, and still stay married that is. I was very happy with my marriage to Mike and wasn't interested in risking it for anyt...

The Fall Ch. 02

by highlands_master on Sep 17, 2017
BDSM

You really need to read part I to get the setting here. This story is going to have a bit more involved setting and plot than some you'll see her-to some it may seem slow moving. ============= Work in the re-education camp was, well hard. The camp has some basic industries that supported "The City". There were "Education" Sessions both morning and night-th...

Julie

by SmlJohnson on Sep 17, 2017
BDSM

My sister-in-law Julie was staying with us for a couple of weeks. She is a sales manager for a large software company and was supervising an upgrade for a major bank in our town. Julie is 35, tall, blonde and very outgoing. She's been married and divorced three times and always seems to be dating a new guy. My wife, Julie's younger sister by 6 years, is just...

Population Crisis

by bastian on Jan 5, 2020
Science Fiction

Global food shortages brought about by rampant overpopulation in the 2020s brought humanity to the brink of collapse. By 2028, scientists predicted that unless we, as a species, could bring the population down below 4 billion by 2045, humans would face certain extinction. The world burned, and for half a decade, civil war and strife reigned as governments tr...

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Milkman Christmas

by Dr. Bull on Jul 14, 2020
Loving Wives

As a Milkman delivering before most people get up you often time find people in their most interesting... shall we say attire. You are there when the least expect you, and seldom notice your presence. At Christmas time each year, people are often generous with gifts for the milkman, tips, cookies, cakes, even gloves or maybe a nit hat. As a senior in High Sc...

Fulfilling My Wife's Cuckquean Fantasy Again

by JackTheCrackAttack on Sep 25, 2017
Fetish

A woman in my workplace wants to fuck me, but I turn her down. However, my wife wants me to take her into our bedroom and watch us inside our closet. Lots of screwing between me and my wife before I screw 'the other woman.' Small Note: I love my wife very much and will NEVER leave her. I know I've stated this before, but I'm saying it again. A cuckold or c...