Boss Cuckold Stories

46,022 results
Orientation
Length
Source
Infinite Scroll

Power

by nero1211 on Sep 27, 2015
MILF

John was never a popular kid in school. He wasn't athletic and he didn't have any outstanding talents. Even his grades were mediocre at best. John lived in a regular suburban area with his 40 year old mother and his 46 year old dad. John was at best 5'6. Not very tall for a senior at high school. He had chocolate brown hair, the same as his parents, no muscl...

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The Professor's Wife

by Mr Robert on Sep 17, 2017
Loving Wives

Charles Gray was the sort of man who would not be noticed in a crowd. However as Professor of English at the local University he was instantly recognisable by his students. They knew him as a dedicated teacher and although very popular, he was also the butt of many a joke told at his expense. To be blunt, Charles Gray was a weedy looking individual, skinn...

Dinner Party - A Cuckold Journey

by Cuckyboy3 on Sep 14, 2020
Fetish

Characters: • Linda, hotwife, 33 years old, a tight & fit yoga instructor of Mediterranean Italian heritage with olive skin tone and long, luscious, brown hair, and curvaceous proportions. Linda has an insatiable sexual appetite, has always dreamed of a manly man, but learned only after marriage that her husband held cuckold and sissy tendencies. Loves her...

Rachael Ray Nympho Queen of Mean Ch. 02

by DickThePimp on Jul 17, 2018
Celebrities & Fan Fiction

THIS IS A PARODY... IT IS NOT REAL... IT IS A FANTASY This is my second Rachael Ray Queen Of Mean story... It concentrates on her getting fucked at her bondage orgies... It's freaky... Enjoy. *** FUCK MY GODDAMN ASS, MOTHERFUCKER!! FUCK IT HARDER, BITCH!!" Rachael wanted her thick ass fucked right and dammit, she was gonna get it, fucked right! She was ri...

Dominant Wife, Husband's New 'Duty'

by keptsissy on Sep 19, 2017
Loving Wives

She sits on the seat in front of her make up table. As she does her eye makeup, staring into the mirror, she talks to me. "Do you want to fuck me?" She leans in, concentrates on her left eye, brushes dark dusting onto the lids. "Yes, Ma'am, yes. I stammer, stare with a shocked look on my face. I'm naked except for a pink ribbon tied around my soft peni...

Morgan's Lunch Break

by Ben Rosewood on Dec 5, 2018
MILF

The alarm assaults my ears so my hand returns the favor by smacking it. Time to get going. In the shower, I decide to have a quick play with myself and my vibrator. A little bit of me time before I have to get my son ready for school and go to work. Between spending time with my son Max and my job as a lawyer, I didn't have much time for dating, so I take wh...

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By All Means

by Greyrock on Sep 21, 2019
Miscellaneous

{if Edge < 200}{else}This is only intended to be experienced in game mode.{endif} Author’s note: This story is a slow burn to get to the good stuff. Feedback is appreciated. Enjoy. Part 1 “Victoria fucking did it again!” I fume, skipping the formalities of greeting Lewis as I let myself into his apartment. He knew I was coming and I have the spare key. “N...

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A different lust

by ZeroKonD on Dec 24, 2018
Fetish

Hello and welcome to "A different lust" option selector. Here you can choose the start of different stories in various environments and situations such as; A Married Life School Life Mind Control Powers Kidnapped by Aliens Rulebook/Rulephone/Rule Powers Alternate Universe Space Colonization Trapped in a Game and various more! Any reader that...

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Hometown Adventure

on Jul 22, 2016
Group Sex

As you have finally graduated from college you are finally free again to do what you want. You are 23 years old and there's no need to hurry and find a job. You inherited a lot of money from your grandparents, and you could live off that for a while. You live in a largely populated city, the residence of the aforementioned college you just graduated from. It...

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Nothing Left To Lose

by griart on Sep 17, 2017
Non-Erotic

This is my first submission to Literotica. I also extend my sincerest apologies to NTRmaster for hijacking his "Reunited" series, in my foolish attempts to offer some smidgen of resolution to the pathetic life of Terence. ***** My name is Terence, but most would just know me as the cuckold wimp that people could push around, humiliate and ruin. His name w...