Old Boss Stories

188,080 results
Orientation
Length
Source
Infinite Scroll

Under New Management Ch. 04

by DontJudgeMe on Sep 26, 2017
Erotic Couplings

I'm sorry it's taken this long to get you an update but I became a father a couple of months ago, and my son does tend to take my time and attention. Thank you all for the many encouraging words and suggestions. Honestly, I doubt I'd have finished this chapter if it weren't for my eager audience. Saturday morning Bret mercifully had the opportunity to...

Watching My Wife Ch. 01

by cuckoldtony on Sep 11, 2017
Loving Wives

My wife's first Christmas party with her new employers was looming and she was worried. It was fancy dress and the theme was vicars and tarts. She told me she didn't feel too comfortable dressing like a tart in front of people she had barely got to know yet, so I gallantly offered to go as a tart leaving her free to attend dressed as a vicar. That did it, sh...

And The Winner Is...

by freeman64 on Sep 14, 2017
Erotic Couplings

Sexy, 27, unattached seemed to be the perfect formula for a crisis for Celine. Today being the first day in her new job as a graphic artist in an advertisement firm, she was early at the new workplace and was waiting for someone to turn up. In the meanwhile, she thought how she naturally attracted all types of men; studs, lovers, wimps and pimps alike. The...

Discovering Allison Ch. 3 & 4

by story_time on Sep 14, 2017
Loving Wives

PART 3 DISCOVERIES Randi left his passed out wife in the bed and raced to his desk. The computer whirred as it began capturing all of the files from Kurt’s computer. Randi spent the time trying to figure out what he wanted to find out from all the information. The first task of course was to see how many images of his wife and what they revealed. As the tr...

Ankle Bracelet

by Winterfrog on Sep 14, 2017
Loving Wives

I'm a plumber and owner of a successful plumbing business in a small Scandinavian town. Not a good guy, but nobody can regard me as a bad guy either. I was lucky in gambling six years ago and won a nice amount on Lotto, which I invested in the plumber business and a nice house. But I was less lucky with my love affairs which usually only lasted a few months...

Anal Amber

by dirtyjoe69 on Sep 13, 2017
Anal

"Yes that's it baby fuck me up my tight bunghole!" Amber screamed at her boss. It was another lunch time romp at work and Amber was getting shafted. Not the type of shafted one might get to experience from their employer though. Amber was presently bent over her boss Taylor Watson's desk. Her tartan blue skirt hiked over her humungous ass, his cock buried d...

Cleaning Windows

by tamol on Sep 13, 2017
Group Sex

My eyes felt heavy as I began to wake up but something seemed very strange, or maybe I was still dreaming. As I went to rub my eyes I found it impossible to move I was confused until I realised that Paul was up to his silly tricks again, my wrists were tied together and secured to the top of the bed; my ankles had been tied to the bottom corners and I was...

My Boss Didn't Know How to Ask

by shavedkitty23 on Sep 19, 2017
Anal

Working for a female boss is not something I really had a problem with in principle, but working for my female boss was a definite problem. She was definitely the type to make sure everyone knew she was in power almost in a way to counteract the "weaker sex" stereotype. She was a 40-year old divorcee which really wasn't a surprise as there was no question th...

Cucked the Boss

by oldandhorny on Sep 2, 2017
Fetish

I recently invited my boss around my house after an afternoons drinking at work. When we got into my room, I told him I had a treat for him. He did not expect this. I know what he likes and so I started off tying him spread eagled to the bed and then placing a blindfold over his eyes. He loves to be tied up and I could already see him becoming aroused thro...

Sophie's Late Night Phonecall

by The_shadow_rising on Sep 19, 2017
Erotic Couplings

Part two of the "Sophie" series "Call now for instant relief, you'll just lo…." The rest of the advert was cut off as Sophie switched the tv off. Leaning her head back on the sofa she sighed softly. Glancing at the clock on the wall she noted that Josh was an hour late. He had gone on a business trip, an urgent contract. One that could make them rich su...