It started as the most embarrassing thing of my life. It has turned into a situation I'm enjoying!
I own a real estate office and for twenty years I have been crossdressing. I meet guys 2,3 times per month in my office after hours..
About a year ago I had a date with a guy I'd been with a few times. I was enjoying him so much I failed to hear the office door open. John,my sales manager stepped in to see me dressed getting my ass pounded by my black friend! I looked up and as he said " oh my god,I'm so sorry " shut the door and he left the building. My friend finished in my butt as my mind raced.
John is a great guy and very ambitious, always trying to make more money. The next day he came to my office and shut the door. He announces he has an idea. He will keep it secret if I'm willing to go along with his plan. He explained he was going to essentially be my pimp! I had no choice and agreed.
He placed an ad on Craigslist and soon I became a crossdressing prostitute. I have no idea how much John is making but he bought a new BMW!

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Anonymous

by Anonymous on Jan 14, 2018 at 9:50 AM

Probably fiction but funny nevertheless. Thanks.

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