Shemale Boss Stories

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Bank Teller Turned Hooker Ch. 11

by SweetTastnNess on Dec 9, 2019
Group Sex

Chapter 11 - THE BOSS KNOWS For the first time all weekend we both went silent. For the next two hours we concentrated on our tans, turning every few minutes. But halfway into sunning ourselves, Mae excused herself to go inside to pee. She was gone almost twenty minutes, and returned to enjoy the sun. I think I actually dozed off a couple of times and I sus...

A New Chapter in Her Life Ch. 07

by CarnalLusts on Dec 9, 2019
Novels and Novellas

Jenna woke late the next morning alone in bed. She looked around for Cindy but didn't find her. Stretching her arms, she happily thought about what happened last night and let out a satisfied moan. She closed her eyes, let one of her hands slowly trace her contours down to her pussy imagining her soft touch was Cindy's hand working her velvety pussy. With a...

Marked at the Beach

by BubbleMonarch on Dec 24, 2019
Fetish

Arthur leaned back on his elbows. The air was too hot, but the sand underneath his beach towel was cool, and the tree arched over him blocked out the worst of the sun. Arthur could hear the voices of Digitalis, his boyfriend of just under a year, and Digit's two daughters over the waves out on the beach. Digitalis's two-year-old daughter Hydrangea had arrive...

Rim Nation Pt. 01

by bbob13 on Dec 24, 2019
Anal

Rachel and I had been working together for a while now, and there was always a hint of sexual chemistry between us - but I was technically her boss, and there is a 10 year gap in our ages. Not to mention I was already in a relationship. She was blonde, fit, a swimmers physique, breasts made to cup, thighs that I could fall asleep between, and oh my that ass....

Rear Naked

by JusBlaze69 on Feb 26, 2019
Fetish

When Valerie observed with amazement how Charles picked up Jessica with one arm, she knew she wanted to fuck him. Her mind was made up. Watching Charles lift up Jessica's 135-pound frame with ease with a bad shoulder and one arm snuggly tucked inside of his white belt, caused instant pussy wetness. Charles was excited about his first private lesson with...

Recruiting with Benefits

by Iwantmoar on Feb 26, 2019
Erotic Couplings

This is a work of fiction based on a true situation that happened many years ago. The names have been changed for obvious reasons. Everyone involved in the story is—and was at the time—over eighteen. A shout out to OldNakedDad for being my editor on this. Your insights have vastly improved the story! It is an unusual story with a different ending. There...

Surreptitious Love Ch. 03

by BenGarland on May 20, 2019
Erotic Couplings

CHAPTER 3 - A SURPRISE PROPOSAL When she texted me about two weeks later, I was surprised and also a little worried. She said she needed to see me. I texted back "Bad news?" but she said, "No, good news, maybe." I told her that that still sounded like a baby. She texted me like a dozen smileys and assured me, no, there was no baby on the way. She wanted...

Black Guy Took My Girlfriend

by Jaytrade on Jun 12, 2019
Interracial Love

This is a story about an experience that happened with me and my girlfriend Hana. Hana was 36 years old, tall thin brunette with nice tits. We had a great sex life and she was really into me. Hana had this friend called Mel who was a bit of a surfer type girl - pretty blonde with big tits. I never quite trusted Mel and I didn't like Hana hanging out with h...

Cammie at Work Ch.04

by Thadsgood on Nov 18, 2019
Erotic Couplings

{Part four of, "Cammie at Work." My ex-girlfriend had asked me to guide or lead her in fulfilling some kinky fantasy adventures regarding her workplace. She got "caught" by one of her co-workers, Ron and in order to satisfy his blackmail demands she has become his "go to" sex partner whenever the need strikes him. He was particularly rough the last time they...

The Sleaze King Ch. 01

by DickThePimp on Dec 2, 2019
Celebrities & Fan Fiction

Having a nice time on my flight home from Georgia. Making out with an old friend and fuck buddy Paula Deen while everybody watches. I love being watched. First class is about half full, so a bunch of prying eyes watching Paula jerk my seven inches while we tongue fuck, and while I molest her old titties through her white blouse. I unbutton it most of the way...