Old Boss Stories

188,080 results
Orientation
Length
Source
Infinite Scroll

The Boss Gets Her... Ch. 02

by BigJohnHankins on Sep 15, 2017
Mature

The Boss Gets Her Big Ass Banged Ch. 02 Ok, this is the continuation from my wonderful opportunity to fuck my boss. As a bit of a synopsis: At the time, I was a 34-year-old associate with a large law firm in Maryland. One of the partners whom I worked for was a beautiful sista who I later discovered was 12 years my senior at 46. Rachael, my boss, was about...

Jinnis and Wishes and Tits, Oh My?!

by NewAgeScheherazade on Sep 12, 2017
Transsexuals & Crossdressers

You wouldn’t know it to look at me now, but I was a fiftyish, chubby, archeologist who spent most of his life digging in the southwestern desert for government wages as a civil servant. My name was Eric Stahl. My stamina was not what it was before, and when I got to cum, there wasn’t much but a dribble - not that I got a lot of opportunities out in the boond...

Old Joe

by clipperdreams on Sep 15, 2017
Fetish

I had just moved to a new city, a big, lonely metropolis. I hadn't started my new job yet; I was still moving in my things and hadn't made any friends other than having a nodding acquaintance with an older man in my apartment building. His name was Joe. He was a huge man, probably a weight lifter when younger, had grey hair, blue eyes, about 70 years old, an...

The Christmas That Almost Wasn't

by Jenny_Jackson on Sep 1, 2017
Humor & Satire

"I really hate that old fart," whispered Prancer. "Yeah. I know what you mean. Every year that bastard lays on his ass getting fatter, then expects us to lug is sorry butt all over creation so he can look like a big deal once a year. The rest of the year he don't do shit," replied Blitzen. "And he has us dragging his fat ass around in the middle of winter...

Mrs. O'Reilly's Laundry Day

by milfleglover on Sep 26, 2017
Mature

Irene O'Reilly was working up a good sweat on her daily five-mile run through town. The 61-year-old white-haired beauty loved her runs, particularly on Saturday when she could take her time and not worry about rushing to work as a school principal. She was tall, five-eight, willowy at an athletic 130 pounds, all arms and legs pumping swiftly as she ran the...

She Dares to Play with Her Marriage

by Winterfrog on Sep 16, 2017
Loving Wives

Author's note: This is not your typical stroke story so if that is what you seek I suggest you move on to another story. Many thanks to Angel Love for the great editing of this story. * I'm a rather average married guy living in my Scandinavian hometown. I was neither rich nor famous in any way when I married my boss' daughter. Most of the time it is OK bu...

Mrs. Fourtnoy's Surprise Pt. 02

by Erotic_Fusion on May 12, 2020
Fetish

Melissa Fourtnoy had picked flowers from Mrs. Tunnsmore's garden and delivered them to Mrs. Edith Brickhouse's house. The grandmotherly Mrs. Brickhouse and Mrs. Fourtnoy had a pleasant time. They met each Saturday for tea. It was a two-hour drive for Melissa, but with her love-life barren, it was well worth it. Melissa found Mrs. Brickhouse mature and atte...

Sexy Sally, My Slut Wife Ch. 2

by Jigs on Sep 18, 2017
Loving Wives

This is a continuation of the story of Sexy Sally, her husband Harry, and Harry's Boss, Bob Simpson. The time is the next morning after Boss Bob Simpson has seduced Sally, Harry's wife and turned her into his slut mistress. ------------------------------------The Morning After I awoke about 11 o'clock the next morning. Bob was already up and gone, but he h...

Love Thy Family Ch. 04

by touchmate on Sep 15, 2017
Loving Wives

This is the fourth chapter of the serial. It is best read chapter-wise to follow the characters and events. This is a work of fiction and any resemblance to any persons living or dead or any events is pure coincidence. All characters are over 18 years of age ***** Let me take you back to Aruna. While Sekhar's sister and mother came to his rescue and star...

Secretaries Club: Anna

by Liver96 on Apr 13, 2020
Transgender & Crossdressers

Secretaries' Club: Anna Hello everyone, I'm glad to finally introduce you a popular fantasy. Secretaries have some kind of turn on (not sure if eyeglasses are the reason, but one of them), but what if you find out things materialize in the wrong way? With luck (and time) I hope to write some episodes about this, once again; thank you Thanos for support (sor...