My girlfriend, Anna, a full time escort, helped me find my way out of a financial hole by taking me on as a 'duo' partner and helped me back to solvency. It was a shock to me that I so naturally fell into it. In fact, I never really had much of a sense of my sexuality until that first time when Anna and I worked for Tom, who went on and on about how beautiful I was.
It wasn't that I didn't know I was pretty but I didn't realize how sexually attractive I was to men. It got me to see what was one of my hidden super powers. Hidden even from me. I had also never had sex with a complete stranger. That wasn't the only first...there were plenty that day, hehe. But the point was that something was awoken in me that lay dormant for all of my adult life until that night.
This was something I would never, never have done if it weren't a necessity but at least it was a good time to do it because I was unattached and not working a regular job. When Anna handed me the thousand in cash at the end of the evening I was sure I'd be doing more, at least for the immediate future.
Anna called me two days after seeing Tom in the hotel and offered me another job with her at the same hotel, different guy. "He's sort of a fetish freak who thinks that having fun always means having two girls. I'll warn you he likes girl on girl action so I always plan on putting it in at his direction. Are you alright with that?"
"Are you a good kisser?" I joked.
"Very good, let's hope you don't like it too much." (Insert mutual laughter here) "one more issue will be costumes. He likes role play and the girls to be dressed in character. He picks the role and we do the rest."
"What did he pick?" I asked.
"The farmer's daughters. It's a classic men's fantasy. Very tight jean shorts, plaid shirts tied at the midriff, bare feet and maybe straw hats. Definitely either ponytails or pigtails.
"I think I can handle that. Why don't we skip the hats and concentrate on the hair?"
We didn't have long to prepare but, then again, the look was minimal anyway. He wanted us later that night so basically we pulled the pieces from our closets and she picked me up at eight. "His name is Dennis, he's forty-eight, he's sweet but he likes to be immersed in the moment and the spontaneity of the sex. He'll role play from the moment we walk in the door so he's looking forward to having his farmer's daughters. I'll be Annie and you'll be?" "Daisy sounds good to me," I said.
Later that night..:
"Who is it?" Dennis said through the door when we got to the penthouse.
"It's Annie. You met me at my daddy's farm. I know he run you off but I just had to see you one more time 'cause you said I was pretty."
He opened the door and we took off the trench coats we wore to get through the hotel lobby. "Oh ya, I remember you Annie but who's your lovely friend here?"
"This is Daisy, she's from down the road and she wanted to take a trip to the city. I told her you was a swell guy who said I was pretty."
We played it up as very sexy but clueless, inexperienced farm girls. We circled around him while he fondled our asses and we brushed against him with our tits. "Oh, Dennis! Daddy won't like that," said Anna and we both giggled.
We went way over the top with the stereotype but he ate it up. "Well, Daisy, I think you're real pretty too." I giggled some more. "You think your daddy would mind if I kissed you?"
