Jack & Jill - his first time with a transexual

After I thought I’d enjoyed about as much as I could take, Jill began blowing smoke rings! Wow! Putting her full lips in that rounded, puckered position needed to blow the rings was more than suggestive, it was almost pornographic.

By this time she knew I was staying in the hotel next door and much about where I was from and what I did for work. I had tried to get her to talk more about herself but she would say little except that she worked in show business.

One thing that I kept wondering about was if at some moment she was going to tell me she was for hire. It’s not unusual to have attractive women strike up conversations when smoking a cigar – you get everything from how the smell reminds them of their fathers to how they enjoy smoking too, as if it is the greatest novelty in the world. But few are as sexually suggestive as was Jill.

I’d already eaten dinner so it wasn’t a great idea to ask Jill to dine. Instead I decided to blurt out: “Jill, how about spending the rest of the evening with me at my hotel?”

“I can tell you’re ‘up’ for it,” she replied confidently while glancing through the metal screened tabletop toward my crotch and smiling.

“Let’s go,” I said as I stood up and offered her my hand.

While taking my hand and pulling herself up, Jill said: “Jack, I don’t want you to get the wrong idea. I spoke to you because I was looking for company in enjoying a cigar. But after talking with you I felt a real spark,” she said. “I’m not a slut and don’t go around meeting guys and going off with them as a regular behavior. In fact, it’s really tough for me to meet and spend time with most men.”

“I can’t imagine that, as gorgeous as you are. Plus you are a great conversationalist,” I replied.

“I’m a bit different,” she said as she pressed my hand and stopped walking for a moment. “I don’t have any medical problems or anything but, I have a situation that can sometimes be a bit of an embarrassment.”