Booth Babe Pt. 03 - Sex Stories

Booth Babe Pt. 03

... back to the hotel, stop at the bar for a drink and you explain all of this, then you can change, and we will go to dinner after that." He responded.

"Sounds great." I said, again giving him a big smile.

The exhibit floor closed, and he grabbed his back pack that had his laptop from this presentation earlier in it and I pulled out my purse. As we headed out, I received a number of approving looks from both the men we saw and several of the other booth babes. My feet might have been killing me, but my ego was doing great.

I was happy when John was able to grab a table at the lobby bar that was tucked in the corner and eagerly sat down. He asked what I wanted and went to the bar. When he came back, I made sure that plenty of leg was showing and watched his eyes focus on them. He sat my glass of red wine on the table and took a seat next to me.

I took a sip, again admiring my finger nails on the glass and remembered Kenzie's comment about seeing them holding a dick and smiled. When I sat the glass down my lip stick prints stood out. I could see that John was anxious to hear about how I looked.

"I have been doing this all my life, starting when I was pretty young. When I met Mary my desire to do it just stopped. I didn't do it for a while but like pretty much everyone else that is like me it eventually came back. She knew about it but for the most part it was a private thing." I told him and took another sip of wine.

He didn't say anything, and his face said I ...

... should continue so I did. "After she died it became more frequent, but I only dressed up in my house. While we were on the golf trip Casie came down to go through Mary's stuff and discovered my clothing. She was wonderful about it and very supportive."

"So, she knows... does anyone else know?" He asked.

"Her roommate. The reason I had some clothing with me is because they invited me to their place and her roommate helped me with doing my makeup and nails. I had done some of that before but wasn't very good at it. She gave me a lesson and some stuff to get started." I stopped and took another sip.

"Why did you decide to dress up today?"

"Several things... first I could tell how disappointed you were about the lack of participation in the booth. But really it was because yesterday I was so envious of the women who were working the other booths. I watched them walking by ours and I wished I was one of them. Plus, I had gone out to dinner with Casie and her roommate on Tuesday night while wearing a dress and loved it." I told him honestly.

"So.... Do you... well do you want to be a woman all the time... like have surgery and all of that?" He asked nervously.

"No... I am crossdresser, I am not transgender, or maybe I am transgendered and not transexual. The labels can be confusing. I want to be able to spend time doing this, but I also want to be able to still be Casie's dad and a man." I told him feeling a touch of uncertainty.

He nodded but didn't say anything ...