Shemale Boss Stories

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Letters from a Stalker

by Cinner on Sep 19, 2017
Transsexuals & Crossdressers

"How long have you been receiving these letters?" Det. Anton Judge asked the distraught woman seated in the visitor chair in his office. "About three months," she replied, clenching her fist and raising it to her mouth. "At first I thought that it was a sick joke from one of my idiot friends to celebrate Halloween, but after the second one I began to have m...

College Shemale babysitter

by tomf15 on Sep 15, 2017
Transsexuals & Crossdressers

Disclaimer: All characters are 18 and over. Jessica pulled up in front of a large house at the end of the street. She looked down at the text; 1278 Backstreet. "This is the right place," she thought. Jessica was a fairly normal, attractive college girl. She studied hard, partied on weekends, and liked to work out. There was one thing that separated her f...

Somewhere else.

by latexdoll on May 23, 2010
Fantasy

Waking up this morning I bet you didn’t know it would be the last day you spent here on earth. Climbing out of bed you hit the alarm clock for the third time, you can’t quite place what is wrong, you just can’t seem to get out of bed. Getting ready for work is more of a chore than usual. For whatever reason nothing seems to want to cooperate. Your shower hea...

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Master of the Manor

by AnInfrequentAddict on Oct 19, 2019
Fantasy

"HELLO!?" Amy barely hears her own knocking over the lashing downpour. The lights blinking in the window of the old, odd-looking estate had been the only possible reprise in sight. She had walked stubbornly for miles, convinced that the next town was far closer than it had proved to be, before stumbling across a huge wrought-iron gate amidst the th...

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'''CHAT'''

by Ssrd33 on May 10, 2019
Transsexual

Hi Jhon!, Hi Mike ... I answered lazily ... like all the days, my life had become very routine and repetitive, at home my wife does not serve me as a man or husband, I think I was dating I sneaked in with another man, but at this point in my life I did not care and the children made a mess everywhere. I wanted to escape this prison from which I felt trapped,...

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My New Boss

by archyx on Sep 12, 2017
Transsexuals & Crossdressers

Bonjour, this is my first try at writing a story here. As I am french, this is my second language, so please be nice and leave positive comments. ***** I had a really bad week. Actually, bad would be an understatement, shitty would be more appropriate. Problems after problems had punctuated my Days. I managed to get a new job as an assistant executive at a...

Swallowing My First Shemale

by Nitromethane on Oct 14, 2017
Transsexuals & Crossdressers

It's been a couple of years now that I've been intrigued by shemales, and though I've met up with a few I've met online, I've still not gone any further than some stroking or letting them blow me. I'm not sure what my hangup is, since I can't seem to stop watching these gorgeous girls on all the websites, but I'm still so nervous about taking that big first...

Dark Angel Ch. 01: The Meeting

by ReiverToo on Sep 12, 2017
Transsexuals & Crossdressers

It was after 10:30 pm when my Japanese business associates had finally had enough sake and karaoke to call it a night. Maybe they were just off to see if they could score some company for the rest of the evening. Who knew? They were all on huge expense accounts, so buying a girl (or boy) for the night was not a financial problem. Some had even offered to inc...

Jennifer's New Adventure Ch. 01

by JenniferTaylorTV on Jan 28, 2020
Transgender & Crossdressers

Author's note: This can be read as a stand alone tale but it perhaps better enjoyed after reading Dan's Dreams Come True. Thanks too for the wonderful feedback. It makes working on these stories so rewarding. Jenniferxxx ------------------------------- Dan was woken from his deep sleep by a loud knocking on the door. He stumbled out of bed, grabbing his dr...

Pam's Shemale Experience Ch. 07

by majicman21 on Aug 20, 2018
Transsexuals & Crossdressers

Author's Note: While this is quite obviously a continuation of Pam's Shemale Experience, it also follows 'Pam's Gangbang Experience' from the Group Sex category, 'Pam's Lesbian Experience' from the Lesbian Sex category, and 'Pam's Threesome Experience' from the Loving Wives category. Reading those three stories might not be necessary to enjoy this one, but i...