First Time Meeting in Cleveland – Part 3

After hanging up the phone, my shemale mistress kept a firm hold of my balls while I was down on my hands and knees. Then, I felt her work two fingers into my ass. The feeling of being penetrated like that almost made me cum on the spot. Feeling her spread my asshole apart with just two of her fingers made me think that there would be no way that I could take her thick cock. “Hump my fist faggot,” she said, and I started moving back on forth on her fingers fucking myself.

I was moaning as I was fucking myself on her fingers. She told me that I, “needed something in my mouth to keep me quiet,” while I was fucking myself. She slipped off her heels and shoved one of her pumps into my mouth toe first to gag me. I could smell the scent of her stocking foot drifting out of the shoe and I was on the verge of cumming again, but I managed to hold back. When she removed her fingers from my ass, and replaced them with what seemed to me like a huge butt plug. Tears came to my eyes as the rounded base of the butt plug pushed past my asshole to fill me up.

When I was plugged, my mistress took a seat in her chair again, and removed her shoe from my mouth. She put her fingers which had just been up my ass in my mouth for me to suck clean and then grabbed me by the back of my head and pushed my face into her crotch to kiss her thick cock through her panties. I could feel her cock grow with each kiss that I gave it. I was hoping that it would pop out of the side of her panties and right into my mouth, but I knew that she would make me beg for that privilege.

To be continued …

First Time Meeting in Cleveland – Part 2

My shemale mistress finally got to my room at the end of the hallway, and luckily for me, no one had come out of their rooms to see me crawling behind her on a leash and collar. When she got into the room and closed the door, she dropped the leash of the floor and went to sit in the chair across the room. She crossed her long legs and lit a cigarette while I was still on my hands and knees where she left me. Once she had taken a few drags from her cigarette, she told me to stand up and to strip.

She was slightly smiling as I stripped for her because she could still tell that I was nervous. When I was naked, she instructed me to crawl to her. My stiff cock was rubbing against my thighs as I crawled across the floor, stopping at her feet. She held out her hand, and I knew that she wanted the leash back. Without being told, I lowered my head and picked the leash up with my teeth and placed it in her hand. She yanked on the leash to lift up my head and blew her smoke into my face.

She knew from our emails that I had a foot fetish. She pointed to her foot, and I lowered my head to start kissing the arch of her stocking foot. She pulled on the leash to have me kiss my way up her long leg and she flicked her cigarette ashes on me. When I got to her knee, she grabbed me by my hair and pulled my head to the inside of her thigh. I managed to steal a glance up her skirt from this position, and I could see a hugh bulge in her panties and pantyhose. My cock was starting to drip precum at this point; I wanted to be kissing her big cock through her panties and pantyhose before wrapping my lips around it.

While I was kissing my way up to her bulge, the phone in my room rang. My heart almost beat out of my chest – it had to be my wife calling me at my hotel room. I told my mistress that I needed to answer the phone. She picked up the phone herself and held it up to my ear so I could talk. She was standing behind me while I was still down on my hands and knees talking on the phone while my shemale mistress was holding the receiver. It was difficult to keep my compsure while talking to my wife, especially when my shemale mistress reached down and squeezed my balls. I should have just told my wife what I was doing so I could start sucking on my mistress’ big cock, but the wife finally said goodnight.

To be continued in Part 3 …

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 …