First Dates

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I spent the next couple of days going over the schedule for my job and having a couple of Zoom meetings with contractors. Everything was set to go, and it was also the day I was supposed to meet Carol, Mistress' friend.

My mind continually drifted to what would happen tonight. I couldn't stop thinking about it. I had no idea what she looked like or what kink she had that Mistress mentioned.

I thought about calling her to talk more about it, but I didn't want to seem too scared or worried. She promised to take care of me, and I did trust her. Yet, I was also eager. Eager to be a plaything.

I had gone to a store the day before and bought a few pairs of men's thongs. Different colors, but they all had a see-through mesh front with a string that went up the back. Even if it was my first time, at least I could look the part.

Mistress had called yesterday, letting me know where I was supposed to meet Carol. And what to wear. After my grooming routine, I dressed in black suit pants, a sport coat, and a blue button-down shirt. I also chose a dark blue thong underneath.

I was further instructed to wear my steel cage and give Carol the keys. Mistress told me to remember my training and just be a gentleman.

I pulled up to the Aria hotel, leaving my car to the valet. The place was grand and over the top. I found the restaurant and spoke to the hostess. She led me to a table where a captivating woman was sitting.

"Carol?" I asked.

"You must be Jake! It's very nice to meet you!" She said, standing up and shaking my hand.

I motioned for her to sit first, then took my seat across the table.

"Seems this will be a first for us both. Ashtyn told me you have not been on a date yet."

I chuckled. "A date, yes. But never anything like this."

Carol looked like a professional woman. Dressed conservatively, not unlike what Mistress wore when I first met her. Carol's hair was light brown with blonde highlights and put up in a tight bun.

She was slender and had a nice figure. I was guessing her age to be about forty-five? I also noticed the huge diamond on her ring finger.

Catching me looking, she lifted her hand up closer for me to see. "Before you ask, yes, I am married. However, it's a marriage of convenience and beneficial to both our careers. Personally, we both live our separate lives. Does that bother you?"

"No ma'am." I said, smiling.

"Good. So, Jake, tell me about yourself. How did you end up here with a lonely old woman like me?"

"Hahahaha! You are not old. And you are a gorgeous woman as well." I told her. I wasn't really sure how much to tell her, and I didn't want to make something up, so I told her exactly how I did end up here. Minus the training the other day.

The waiter had come by as I talked. We both placed our orders, and she ordered an expensive bottle of Italian red wine.

"Interesting." She said when I finished my story. "Ashtyn and I have been friends for years. She knows my marriage is just for show, and with my career, I just don't have much time to date. But, Ashtyn knows about my kink as well!"

"So, do I dare ask what your kink might be?" I asked.

As the waiter brought our food, Carol replied, "You'll find out soon enough."

She laughed when she caught me rolling my eyes.

"Oh!" I pulled the key to my cage from my pocket and handed it to her. "I almost forgot."

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