Helluva Boss Stories

41,749 results
Orientation
Length
Source
Infinite Scroll

Annie & Her Boss

by rock man 51 on Sep 13, 2017
Loving Wives

She walked slowly down the long hall toward the closed door. The sound of phones ringing, people talking and keyboards clicking emanated from the offices around her. She stopped suddenly before the ornate, wooden door. She noticed that the secretarial desk on the left, where Miss Chang sat, was vacant. Her eyes stared at the gold nameplate attached to the do...

The Sinner's Canon Ch. 07-08

by SevMax2 on Jul 14, 2020
NonHuman

Chapter 7 "Dios mio ... where am I ... oh, wait, Jack? Jack Benton? What's going on here? Sandra ... and Jessica? And who are you?" Rita Escobar stood in her novice's habit now, truly shaken up by having had the Devil grab her and bring her here to face me and two of my other girlfriends, plus Lilith ... and Tyler, of course. "I'm Lilith, of course. Yes, T...

Windswept Ch. 01

by indiglowblue on Sep 19, 2017
NonHuman

Twenty Years Previous The pregnant woman was going to die. Ryder couldn't stop that -- but if he wanted to, he could postpone it. He could give the baby in her womb a chance to live. He had explained that to her, but he had left off a very important piece of information. That was why he was hesitating. "Please," the woman whispered. Ryder gazed sadly at he...

The Devil's Equinox Ch. 06

by coldfire69 on Sep 19, 2017
Novels and Novellas

Baxter's goal was simple: shove his cock inside Lily, and splatter his cum all over her insides. She struggled mightily toward him; he toward her. It seemed like a lifetime ago he had first attempted the utterly useless tactic of cutting his rope with his teeth. That plan had met with sound failure. Every time he tried it. His jaw was sore from the latest...

Mature Married Hairy Pussy Ch. 01

by phunandsex on Sep 12, 2017
Loving Wives

My name is Scott and I'm 35. From the get go, I have to admit that I've got an addiction issue. I am addicted to feeling my cock shoot hot cum into a wet pussy. Not just any pussy, but a pussy that belongs to a mature married woman with a really hairy snatch. I've had lovers from their middle 30's to their middle 60's, professional women, housewives, all sor...

The Cheryl Cummings Story Ch. 15

by mark_8675309 on Sep 15, 2017
Interracial Love

It was Wednesday night again, and the girls were back in Belinda's basement working out hard yet again. "Alright girls, one more time, come on, 10, 9, 8 7, 6, keep it going, 5, 4, 3, 2, 1." The music began to fade as Teresa finally started to slow down a bit. "OK! That should about do it! Wow, that was great. Good workout girls!" exclaimed Teresa to her swe...

Payback

by gldngolfer on Sep 17, 2017
Non-Erotic

This is the sequel to "I Warned You." I hope you enjoyed it and didn't take it seriously. There is only a mention of sex in this story. I decided to keep it in the category of the first story for consistency. Please don't take either of these stories seriously. There is no permanent damage done to anyone. Just read and enjoy. ***** Payback For those of...

The World's Horniest Trailer Park

by DickThePimp on Mar 26, 2019
Celebrities & Fan Fiction

WARNING: White Trash Fuck Parody... Fucked Up And Freaky As Fuck... "Just fuckin' film it jackass! Yeahhhhhhhh... lick that piss up bitch! Who's your piss daddy?" "You are baby. You're my beautiful, piss daddy James. Mmmmmmmm. (Drinking down every drop of my piss)" "Zoom in... get in her mouth. Make sure they can see her swallowing my fuckin' piss. Don't...

Badge of Dishonor Ch. 10

by D.C. Roi on Sep 15, 2017
Novels and Novellas

Passion In James County X Badge of Dishonor By D.C. Roi Chapter ten Lise had been working for the sheriff's department for almost a month now, and she had really grown to love her job. Not only was she getting the hang of the job, she was making friends, too. She had just finished her work for the day and was about to stand up when her phone rang. She pi...

Carrie & Rob Ch. 04

by PoppingTom on Sep 16, 2017
Interracial Love

Hi, here's Carrie. Am I look good? Full secretary outfit! Every boss would take me without application, just by looking at me! I like myself looking like that. And this is Rob. Rob's dressed so damn good! Black suit in black body. Armani is a black man, I'm convinced. Yeah, I know what you wanna say: Rob n' Carrie goes mainstream. Next thing will be the pro...