Boss Cuckold Stories

46,022 results
Orientation
Length
Source
Infinite Scroll

History Repeating Itself Ch. 01

by ZuzusPetals on Sep 13, 2017
Romance

The black SUV had been following me for almost a mile. Just lurking a few hundred feet behind me, driving slowly in the misty light of dusk. I looked around the empty park I was running by, realizing no one was out. I'd left my cell phone in my car, and panic was beginning to set in. Suddenly the car began gaining speed, and I pushed myself harder, trying my...

She's the Boss: A New Toy

by SonofGondor on Aug 31, 2017
Fetish

A Note to the Reader: although the following scenario is fictitious, it is based on a fantasy shared by myself and my beautiful girlfriend, who I also have the honour to call 'Mistress.' Once again, I must begin by thanking Aubrey for allowing me to immortalise our relationship in this way, but must emphasise that all other characters besides ourselves are e...

The Connection

by Fantasealor on Sep 12, 2017
Erotic Couplings

It wasn't a wise idea to go see Joe, my ex-boyfriend, who lived two hours away and in another country. I knew he lived with another woman, but he told me through various phone calls and e-mails that he was not happy with her. I felt that same warm, comfortable feeling when we talked on the phone. I hadn't seen him in three years and I just wanted to know if...

Sinthia Becomes a Holiday Rep Pt. 04

by lickablelucy23 on Sep 14, 2017
BDSM

Hi Everyone, This story follows on directly from where part 3 finished, so this will make much more sense if you read parts 1, 2 and 3 first, sorry for the long wait for this part. As always I love getting comments and messages about my stories from all of you, especially from other girls! Thanks and I hope you enjoy, Love and Licks, Lucy X X X X * * *...

Abby

by TxRad on Sep 1, 2017
Group Sex

Ah yes, Abby! She brings back such fond memories. She was a cheerleader when I first saw her. A short skirt, a bulky sweater, pom-poms, and a beautiful, vivacious, athletic young woman... what else could a man ask for? I spent wonderful hours watching her bounce around, kick her legs up, and do cartwheels almost every afternoon after school. We were both bre...

Infection Ch. 07

by dweaver999 on Sep 15, 2017
Sci-Fi & Fantasy

Chapter Seven Resolution By four in the afternoon Harold was feeling incredibly horny again. At first, he had been thrilled by his new found sexual stamina. Now, however, it was becoming a little tiring. Even in his younger days, he had never had this much raw need for sex. His cock was rigid again, a mere four hours after fucking Becky. And that was a mer...

Trip to the Islands

by Grey Eagle 286 on Sep 14, 2017
Loving Wives

Charlie Martin couldn't help grinning as he stood by the window in the arrival area at the airport He watched as the huge jet taxied up to the terminal finger and the boarding ramp slid out to the door of the plane. He was trembling as he waited for his wife of fifteen years to come off the plane. This was the longest they had ever been apart. He knew who i...

Redo

by cassandraharper on Sep 13, 2017
Interracial Love

The alarm clock beeped incessantly, startling her awake as she groaned, slapping her hand against it repeatedly. "Shut up!" Tiredly, she regarded the time, snuggling comfortably under her blanket in preparation to fall back asleep until reality dawned on her and her brown eyes popped open in surprise. 10:25 A.M., she read then reread as shock caused her to...

The Beguiled Gynaecologist

by MawrGorshin on Sep 13, 2017
Erotic Couplings

Dr. Barry Smart, a handsome 49-year-old brunet with a slight gut, went into 'Le Strip' at around 11 pm on Saturday night. The owner of the Hamilton, Ontario strip club approached him as he, sulking, was looking for a place to sit. "So, trouble at home, eh?" the owner asked, having previously chatted with Barry on the phone. "Yeah," Barry said with a sigh....

Romance The Long Way Round

by Pussyrider on Sep 16, 2017
Romance

I'm not sure exactly when I fell in love with Jenny. I suppose it must have been quite early in our acquaintance. We actually started with the company at more or less the same time. I was a graduate trainee, very proud of myself in my shiny new Burtons suit; she was simply one of the nameless plebs who used to push the post trolley around the building three...