Sissy Boss Stories

46,032 results
Orientation
Length
Source
Infinite Scroll

Bobby and Abby's Amazing Adventure Ch. 04

by emelle78 on Dec 3, 2019
Loving Wives

Abby tells Bobby of fun with Clarke and his boss in her office After Abby and I had that wild session on the couch our house was charged with sexual energy. Abby dressed in sexy clothes and constantly had me tending to her needs. Starting the very next day Abby had me eat her to orgasm every morning, and then she'd tease me, talking dirty to me about fuckin...

Becoming Daddy's Girl Ch. 03 - Final

by Sungmehetu on Jan 1, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** Warning: This chapter is very focused on water sports. The main character ingests urine on a constant basis. If this makes you ill, do not read. ***** My bladder was screaming on the ride home. Every bump in the road, caused a sharp pain. I was about to piss in the front seat, w...

We Need to Talk Ch. 03

by tennesseered on Jul 10, 2018
Loving Wives

A work of fiction, all characters are over 18 years. Best read sequentially starting with chapter one. The cops pay a visit after Myra's and Wendell's big adventure. In a nod to Luedon, I took the ice out of the scotch. ***** We got back to our house about noon after our fleabag motel adventure. Myra sat at the kitchen table while I made a pot of Earl Gr...

Pillow Talk Ch. 05

by MicheleNylons on Sep 11, 2018
Transsexuals & Crossdressers

Chapter Five - Braciole The first plate whizzed past Frank Caputo's right ear and crashed into the wall, closely followed by a second that skimmed off his shoulder and shattered on the floor. "For fuck sake Michelle if I wanted this fucking drama I'd go home to Benedetta," Frankie whined, but he was laughing drunkenly. "Why don't you then? You can fuck he...

A Little Payback

by Justplainjeff on Jul 27, 2020
Loving Wives

Author's note: All persons depicted in this story are purely fictional. No person involved in any sexual hanky panky is under the age of 18. Slow buildup, but I hope it is worth the read. My name is David Brown. I have been employed at a mid sized law firm in the Greater Seattle area for nearly 18 months, with a specialty in corporate law. I am approaching...

Pixie Prey

by AlinaX on Jul 13, 2020
Sci-Fi & Fantasy

"Let's stop for a while," he said. I hadn't been asleep. Not completely, anyway. The sharp, unexpected braking manoeuvre had stirred me back to life in time to see the sign. Pointing to the left, a picnic site. In the middle of the forest. Robert turned into the narrow lane, the road surface broken and uneven. "If only we'd brought food," I murmured. "We co...

Another Life

by Ahazura on May 15, 2019
Loving Wives

I came across this one when I was looking for another story I started years ago. Everything kind of clicked and I finished it up. - Ahaz I came home messy and dirty after a long day of work. One of my regular guys had come down with the flu and the crew needed someone to crawl under the house and run the wire. I may be the boss, but I was also the thinnest...

The Adventures of Polly Pt. 02

by CyrusL on Jun 8, 2020
BDSM

Next morning by 7.45am there was still no sign of Polly. This was not going to be a very auspicious start to my obedience course, but it gave me the opportunity to make her lack of punctuality as good an example as any of behaviour to be avoided. At 8.03 Polly casually strolled into my office. "Sorry I'm late, Boss. I missed my bus." I really couldn't be...

Librarian Finds Long Overdue Love Ch. 12

by RVon on Mar 18, 2020
Fetish

November 30, 1987 Single, middle-aged and bespectacled Angelina Lione may look the part of the prim, proper and sexually repressed, buttoned-up librarian, but she's most definitely NOT your father's librarian - at least not in private. Blessed with a ravenous and unquenchable sexual appetite, Angelina's orgasms are so intense that she oftentimes faints duri...

Please, Mistress Pt. 01

by MadameBloom on Oct 6, 2020
Exhibitionist & Voyeur

It was moments like this when he felt completely divorced from his body. Adam had often imagined himself on an island. Bright blue skies. Lush trees. The sound of a babbling brook even, if that wasn't too much of a cliche for a daydream. He shut his eyes, and leaned forward, gripping the railing so tightly, his knuckles went white with effort. Under the sui...