Shemale Boss Stories

41,656 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2024 SmutMD.com

Job Interview

by britneyfan on Sep 11, 2017
Transsexuals & Crossdressers

I was interviewing for a new secretary and it had nearly reached the end of the day with no likely successful candidates. There was just one to go, a Tracy Class, whose CV certainly looked impressive and seemed as if she would do pretty well for the job, but I had to wait and see. The company's receptionist, Paula, put her head around the office door to tell...

Blackmailed by a Bitch

by HarlanPilate on Sep 25, 2017
Transsexuals & Crossdressers

'I got it,' Laura said, running into the kitchen. 'I got the job!' That's great,' Dave said. He hugged his fiancée, full of joy at the news. Laura had been desperate to find a new job. Anything to get away from the place where she worked under her nightmare boss, Gloria. 'When do you start?' Laura's smile disappeared. 'As soon as I get my reference.' 'Fro...

Down the Rabbit Hole

by ThighhighMellie on Sep 13, 2017
Transsexuals & Crossdressers

"In another moment, down went Alice after it, never once considering how in the world she was to get out again." -Lewis Carroll Chapter I: Opportunity Zack considered himself an average guy. At 23 years old, he worked a steady job in IT, had his own place, and was fairly fit and healthy. The only thing that stood out was his love of stockings. He'd gravit...

Journey to Trans Submission Ch. 01

by bluev on Jul 15, 2020
Transgender & Crossdressers

It has been at least thirteen years since I first discovered my kink and one year since I started to think about making it come true. This is a kink I have not shared a word with anyone for a fear of being judged and a fear of being told that it was not right to indulge in such objectification. Finally I came to the point where I said "screw the world, it's...

BEA 2016

by devoutmalesub on Sep 25, 2017
Transsexuals & Crossdressers

Book Expo America. Here we go, again. Will it be the same thing again? Fly in, get the baggage, take a smelly cab to the hotel. Meet my Sales Director, Victoria (who goes by V), in the bar. "We've got to set up the booth, Jack. But first, let's have a drink or two!" She winked. V has been my boss for five years. She rode the team hard for sales numbers, bu...

The Society

by Barno on Sep 19, 2017
Transsexuals & Crossdressers

I met her during the summer. I was only nineteen and working to save some money for college. I had been raised by my grandparents who had both passed away over the past year. After the burial costs I was far from wealthy. My parents weren't around so I was on my own at a young age. I had moved a couple of towns over from where I had grown up and was living i...

The Club Ch. 01

by Rak_Sasha on Jul 17, 2018
Erotic Horror

A set of headlights turn and pull into a nearby vacant lot, stopping near one of the overhead lights to reveal a dark sedan. It's driver's side opens to reveal a man looking to be in his mid thirties wearing a grey suit, taking a long drag from a cigar before tossing it onto the ground. Stepping over it and making his way towards the building in front of him...

Shemale Surprise

by silkstockingslover on Oct 21, 2019
Transgender & Crossdressers

SUMMARY: A married man is seduced and taken by a friend of his wife's. EDITING THANKS: Thanks to Robert, goamz86 and MAB7991. NOTE: This story is dedicated to Robert who requested the fantasy...sorry but the story ended up a lot longer than originally planned. ***** "You can stay with Robert if you wish," Mary said on the phone. I looked up from my lapt...

A Shemale Christmas Carol

by ThomX on Sep 16, 2017
Fetish

I got a job working as a mall Santa at the local mall during the Christmas shopping season one year. It had been a real shitty year for me. My wife of almost twenty years left me for a younger man, I lost my other job due to layoffs and, on top of all that, my doctor diagnosed me with high blood pressure (gee, I wonder why?). So believe me when I say the las...

Hotel Club Ch. 05

by pantywriter on Jan 6, 2020
Transgender & Crossdressers

I woke up from a fitful night's sleep. The slow, soft, wet and sloppy blowjob I had given Cindy did not improve my mood, not after the fight with my...wife? Ex-wife? I sat up in bed and rubbed my face hard. The increased blood flow felt good but did nothing to quell the rising anger. I showered angry. Brushed my teeth angry. Dressed angry. Ate breakfast an...