Cuckold School Stories

109,558 results
Orientation
Length
Source
Infinite Scroll

Types of Cuckolds

by cuckwhofucks on Sep 14, 2017
Reviews & Essays

What does it mean to be a cuckold? It actually means many different things to different cuckolds. But let's start at the beginning: The truth vs. the Truth. The Truth, or an absolute Truth, is actually unnamable, or rather it exists, but when you try to interpret it and put words to it, it becomes one of very many truths, as many truths as there are peopl...

How I Became a Cuckold

by Rjt72088 on Feb 6, 2018
Fetish

This is the 100% true story of how I became a cuckold. It took about 10years to get to this point so if It is your fantasy to be a cuck be patient. Sometimes it just takes waiting for the right situation. A little back story. I'm 31 my wife is 32 and we have been together since JR year of high school (2003) she is very attractive and has always been able to...

The Two-Month Break Clause

by TheBiGuy on Mar 12, 2019
Loving Wives

This is my first story, please be kind. Everyone in the story is over 18 years of age. ***** I've been married to my wife for nearly a decade. We're very happily married and have a wonderful family. I had been married before and have children from the previous marriage. My current wife, Natalie, is a beautiful woman in her early 30's with auburn hair, hig...

Thoughts on Cuckolding

by Youami on Apr 3, 2018
Reviews & Essays

Until a few years ago, I had only a vague understanding of the term "cuckold" as it related to sexual relations between couples. As ignorant as I was I thought it had something to do with cheating. However, thanks to the overwhelming number of cuckold stories contributed to Literotica, I have been able to build a better appreciation of this term and the many...

Cheating and Rivals Pt. 28-29

by xleglover on Sep 16, 2017
Loving Wives

Cheating and Rivals – Part 28 (Part 4 of the Caribbean vacay) The sun was shining in the window when Jen slowly woke up. She felt disoriented, not knowing where she was. Oh yeah, the villa, Frank's bedroom. She was alone in bed although the room stank of sex. Jen's body ached. Memories of the hard fucking she got from Hugh and Lou flittered through her gr...

Cuckolding was Me Totally Pt. 02

by ACTDrew on Oct 13, 2017
Fetish

Jill had settled into the new situation with us perfectly and I think I enjoyed it even more than she did. I had taken control of her web sites and had also created a few personnel sites to help her find men to play with (all with big cocks). At home Jill was slowly taking control of the house and turning me into the primary domestic role for the house and...

Little Dicklet Club Ch. 03

by jealouscuck on Mar 23, 2020
Loving Wives

Annette and Nathaniel were the ideal couple in so many ways. They both were considered 'geeky' in school. They were both virgins when they got married. In modern society, that is almost unheard of, but it was true. And rather painfully true to Nathaniel. Annette was wrapped up in her studies and was very religious growing up. Her father was a preacher and sh...

Miranda's Journey

by Drexelhand on Jan 15, 2020
Cheating Spouses

Michael Knauss, Miranda thought fondly as she put on her makeup. Way back when in high school, he was the biggest stud around. Every girl practically went crazy for him, Miranda included. Yet out of all those girls, it was Miranda who wound up being the lucky one that he went out with. She ended up being the lucky one that he took to prom. They had given eac...

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How I Became A Gay Cock Slut Ch. 02

by watchdwag on Mar 12, 2019
Loving Wives

It's been a little more than a year ago when I met a man who would forever alter my life and my wife Laurie. I met Steve at a conference in Hilton Head where I was attending a sales conference. Steve was a trainer at the conference and my company teamed attendees up with trainers, at least those who elected to do so, in order to cut costs. It was at this con...

Maureen, My Queen of Spades

by nocluescooby on Sep 14, 2017
Interracial Love

This story features a theme of hard-core interracial cuckoldry. If you find this theme offensive, or don't like it, don't read the story. This story is part fact, part fiction. No I won't reveal which is which LOL! I have often spent evenings on a chat line. Unlike most of the guys I was never overtly looking for erotic conversations. So while most of the m...