Caught By My Boss Stories

355,706 results
Orientation
Length
Source
Infinite Scroll

Veronica and Mr. G. Ch. 01

by kyle2 on Sep 11, 2017
Fetish

I've co-authored this story in partnership with sexyslut of Pandora's Secret (not Literotica's sexyslut). Major thanks to Literotica's DiamondStar for her fantastic editing services! This is the first part of what we hope will become a multi-chapter series (that, of course, will be determined by reader response). Happy reading! -----------------------------...

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...

Seal the Deal

by deliciouslyfungal on Sep 14, 2017
Group Sex

I'm excited! Today my boss asked me to join him this evening while entertaining a client that our company is in heavy negotiations with. I have enjoyed these occasional outings with my boss ever since the day he caught me in my office squeezing my nipples and playing with my pussy. I had it dripping wet when I noticed him watching me from his office so I k...

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...

Secretary Sandwich Pt. 03

by dpingjessie on Apr 21, 2020
Group Sex

Jason cleared his desk while Abby, his secretary, unbuttoned her top as she faced him. It was now customary for the two to celebrate the weekend with a session in his office before they hit the town. Behind Abby, Shane, Jason's business partner, sat down with his pants already undone and his cock out and rigid. He slowly stroked himself as the red blouse sli...

Please Let Me Be Ch. 14

by xattackx888 on Sep 12, 2018
Anal

Disclaimer: This chapter contains anal, keep in mind that if you plan to do anal play to do a butt-ton of research (pun intended) and to stock up on supplies properly beforehand. This chapter is purely fictional, all characters, events, and places are entirely made up and meant for this story alone. Thus, what you read about anal here is for the story, not a...

The Chance to Change Ch. 01

by GalaxyGazer on Mar 24, 2020
Erotic Couplings

Due to complications I have had to resubmit this story. I'd like to say a big thank you to my editor, WokeUpOneDay, for his edits and suggestions. Do go and check out his stories. I hope you all enjoy The Chance to Change Chapter 1 Typically on Mondays it's my job to start going through last weeks transactions, invoices, stock orders... the list goes on...

Showing Abby Who's Boss

by dpingjessie on Sep 13, 2017
Erotic Couplings

Five years ago, Abby strolled into the meeting room and into my life as a 18-year old having just completed high school. I still remember what she wore: red gym shorts, a blue tank top and black flip flops. Her light brown hair came down loose to her shoulders, swaying as she sat down in the seat next to me while we both prepared for the first day of orienta...

Susie's Peaks Ch. 02

by Kevsta on Sep 17, 2017
BDSM

Continuing Susie's Adventures into her fantasies. Made possible by the help of my good friend, Redfacedandnaked.xx + On the way to the ladies room, she shyly noticed that her boss, and another chap who was with him, looked at her, but not her face, and then looked at her face and smiled. The shape of her nipples, discreetly protruding through the two layer...

Fucking My Boss

by dpingjessie on Sep 11, 2017
Mature

It wasn't right away that I fantasized about my boss. When I was interviewed by her for the job I ended up earning, the thought of having sex with her never remotely entered my mind. Even so, when I did develop those erotic feelings, I never sought anything really passionate or at all romantic. I didn't so much as want to even kiss her. By that point, all I...