Boss Cuckold Stories

46,022 results
Orientation
Length
Source
Infinite Scroll

Cole and Ellen Do Spring Break

by trigudis on Sep 11, 2017
Romance

Being yesterday's hero took some getting used to. Cole Reynolds was no longer the star quarterback. No, at the tender age of eighteen, he was a has-been, already looking back with nostalgia at those thrilling Friday nights on the gridiron, sharing the heat of battle with his loyal teammates, cheered on by his adoring fans. But life goes on, and for him that...

The Loaner Wife Pt. 01

by barkirk on Sep 25, 2017
Loving Wives

"Doug O'Malley, right?" Ed Matthews held out his hand, "How long have you been here, three weeks?" Ed looked at the young blond-haired, blue-eyed man. Doug jumped to his feet, "Yes, sir, three weeks tomorrow." "Sit down and cut the 'sir' shit, my name is Ed." The tall dark-haired man pulled up a chair. "So, I hope you've felt at home here. We really try to...

Ravenswood Sluts Ch. 02

by TLMorgan on Sep 12, 2017
Erotic Couplings

When Frank opened the door, he was expecting some skinny, nerdy Chinese shrimp of a deliver boy but instead, the delivery boy turned out to be a stunning Caucasian delivery girl, possible in her early 20's with massive boobs! This scenario couldn't had been more worse for Frank. "Hi," the delivery girl spoke in a cute, southern accent. "I hope I'm at the ri...

Alphia Corporation Ch. 01

by Hogwash on Feb 4, 2020
Loving Wives

"Look, I've been sent to talk to you about the opening in the junior executive position," Gary said to Sam. "Really?" Sam said, trying to play it cool, because it was well-known that the junior executive position was near the top of the management line at Alphia Corporation. Sam was well-paid, but the executive-level compensation was rumored to start at nor...

The Dance Pt. 01

by TheMarlboroMan on Jun 18, 2019
Loving Wives

Well here I go again I thought to myself as the guard ordered me to place my hands through the slots so he could cuff them. After I stepped back, he opened the cell door and stepped in to put the ankle bracelets on. My third thirty days for contempt of court was done. It was time to see if another thirty days would be handed out by my good friend Judge Jayso...

Chuckwagon Cookie

by JonThomas_ on Mar 26, 2019
Transgender & Crossdressers

Greetings all; in my stories my characters exist in my head, but there might be real life inspirations for some of them. Who knows? Anyways as my regular readers are aware, I enjoy writing about characters with fluid sexuality. The old American west has an image of hardy settlers, tough as nails cowboys, and Native Americans fighting for their land. Howev...

Lost in Argentina Ch. 02

by sadkins116 on Oct 3, 2018
Illustrated

Hello all. I am again working with Rebecca on this story. It is a departure from our usual stories in that it deals with a different fetish than our normal fare. Please be aware that this story has non-consensual sex, forced body modifications, drugs, and mind control. It is a dark story and if this is not your preferences please move on. It is a fantasy and...

A Nun's Story Pt. 06

by mjar65 on Jul 27, 2020
Erotic Couplings

They were standing in an outer office, Sister Claire and Mother Mary, waiting for their appointment. Claire was nervous and excited. She understood that her performance in this meeting would really count towards her future in the Order of the Mount. More important was that she did not disappoint Mother Mary. Claire tried to remind herself that she alone was...

Do You Like My Smile - Her Story

by LarrynDallas on Jun 15, 2020
Loving Wives

This story is based upon Do You LIke My Smile published by The Style Guy in 2019. I felt the original could use the wife's point of view, so I contacted The Style Guy. With his kind permission, I wrote this alternate version. There is some sex, but the focus in on the evolution and consequences of an affair by a woman truly in love with her husband, but sad...

The Submissive Temp Ch. 01

by JBEdwards on Jan 15, 2019
Mature

This is the first chapter of a story with ten chapters. I've decided all ten chapters will be in the Mature category, since our heroine Sally likes older men. I hope that you like it! ************************ There's a Starbucks at Astor Place in downtown New York. The coffee is standard Starbucks coffee, and nothing to write home about. What's great about...