First Time Meeting in Cleveland

I had been waiting for this moment for years. I had been dreaming of being fucked by a beautiful shemale since I first found out what a shemale was. I had come close to actually meeting a shemale a number of times, but I always chickened out in the end. Finally, I thought the time was right, and the opportunity presented itself. I was out of town for the night, and I was supposed to be getting ready for a hearing in the morning, but I couldn’t resist picking up the phone any longer.

I called the shemale escort that I had emailed a few times in the week preceeding my trip, and I confirmed our “date” for 9 o’clock that evening. She was going to meet me in the bar of my hotel in downtown Cleveland. I got to the bar around 8:30, and secured a seat at a table in the back corner of the room, near an exit – just in case I got cold feet again. I had a couple of gin and tonics before she arrived, and when she walked into the bar, my cock got instantly hard. I knew from looking at her that I was definitely going through with it this time.

I got up and went over to greet her, and we went back to my table in the corner of the room. She sat across from me, and had an evil grin on her face since she could tell that I was nervous. “First time”, she asked, even though she already knew the answer. She knew what I wanted based upon the emails that we exchanged. When the waitress came over to ask if she wanted anything, she said bluntly, “just bill the drinks to his room … we’re heading upstairs.” At that she got up and told me to come along. There wasn’t anyone else waiting for the elevator. When the elevator door opened, she grabbed me by my shirt and pulled me into the elevator where she produced a collar and leash.

I was down on my knees in front of this beautiful shemale as she was fastening the collar around my neck and attaching the leash to the ring on the front of the collar. When we reached my floor, thankfully, no one was in the hallway. She led me down the hall to my room, having me crawl behind her. She even stopped a couple of times and had me kiss her feet, legs and ass. It was incredibly exciting and nerve-racking at the same time. I would have been completely embarassed to be seen on her collar and leash, even though the people would have been total strangers. But at the same time, I would have done anything she wanted out in that hallway. I was thinking with my cock at that point, and my cock was ready to cum at the slightest touch.

To be continued …