Old Boss Stories

188,080 results
Orientation
Length
Source
Infinite Scroll

The Peeper and the Bitch Ch. 12

by SaviorSamurai on Jan 29, 2019
Erotic Couplings

This is the last chapter of this series. Honestly, I didn't expect it to get this long. But I'm proud it did. I feel like I did a better job with the characters and the scenarios they found themselves in than my first Literotica story-Xi High School's Dangerous Darling. This series was also much more heartwarming, intense. And yes, all my stories on this...

Light My Fire Ch. 03

by Jigs on Sep 16, 2017
BDSM

Roseanne is by now well into her ‘reprogramming’, and has very little will of her own remaining. Mesmerized, and very nearly in Clyde’s total control, he takes her submission to the next level. ******************** Later, when we were in bed together after Clyde had taken the virginity of my ass, I snuggled gratefully in his arms as gave me my instruction...

Miss Linda Ch. 04

by Bluepen451 on Sep 13, 2017
Exhibitionist & Voyeur

Hi, it's me, Miss Linda, again, the sweet little girl that teaches second graders. No, no, not your second graders. I only teach someone else's second graders. Whew! I'm glad we got that straight. I would not want any of you nice people to decide to go on a witch hunt to out your children's second grade teacher as a pervert that likes to expose herself and...

Boss Ch. 01

by Debutante on Sep 17, 2017
Mature

Anne was the first person to give me a job and take me seriously as an ad writer when I was just a fresh faced college kid. The local office was filled with dusty old women, and let me tell you, Anne was among the dustiest. At about 5 foot 3, with glasses (spectacles seemed more appropriate), Anne was like most aging career PR people - cynical, quiet, pensiv...

Shop Soiled Ch. 2

by jamespatrick2001 on Sep 12, 2017
BDSM

Ta, mate. I'll get the next one in. Anyway, where was I? Right. Next morning I'm at the shop early. Funnily enough, the missus woke up and wanted a bit. I'd fucked the arse off her when I got in and she was well horny again. She jumped on top and started riding the fuck out of me. Thing was, I'd already decided that the bird in the shop was where I was goin...

Daisy Price Ch. 03

by sjmhmttep on Sep 12, 2017
Erotic Couplings

Chapter Three "The Interview" Mr. Craftsman was sitting in his office doing some work on recent sales figures, when the fax machine came on and printed out a fax for him. Wondering what it could possibly be he got up, and went over to the machine to take out the fax. It read: (A Top Secret Fax) (To the new boss, from the old boss.) To: Mr. Craftsman Fro...

Lucy's Big Adventure Pt. 03

by mjar65 on Sep 14, 2017
BDSM

FOURTH NIGHT I was talking to my Boss when DM arrived for me and he was saying things to make me feel horny and have energy for the night. I was really ready and also glad it was the end of the beauty pageant. When I went out to DM I greeted him in the proper way and I kissed his shoes for him. I don't know if any of my neighbours saw me do that. In his ca...

Boss Ch. 02

by Debutante on Sep 17, 2017
Mature

Things had been quiet around the office as of late. I went through the usual post-coital feelings of immense guilt that had accompanied me after every girl I had snagged in college. Imagine bounding into work the next day and seeing your boss, as unsexy as she was the night before, on the phone, clicking on her keyboard, her glasses down to the end of her no...

Does Two Wrights Make One Wrong?

by fanfare on Sep 14, 2017
BDSM

I'm Jesse Wright. This is my story about what happened a couple of weeks ago. When I discovered that my wife Mabel, was having an affair with her boss, Kenny Deever. I was so angry, I canceled my dates that week to fuck my youngest sister-in-law and my best friend's wife. Hell, I was so pissed off at my slut wife, I couldn't even get it up to fuck her. That...

Kim Ch. 07

by Mikro on Sep 14, 2017
Erotic Couplings

Chapter 07: The Decorators The decorators had been in all week Steve the young apprentice and Boss as I called him. I hadn't had sex for a couple of weeks and was feeling really horny. I had taken a week off work, ostensibly to let the decorators in but also because I had been working non stop for 6 week's, unusually long for me but it had been a very prof...