Amazing Night With A Sexy Crossdresser by markerss

This happened a while back now, but the experience has stuck with me and I wish I could be with her again. At one point, I had become very interested in transsexuals and cross dressers and had even been with one that I met on Craigslist and another I met at a bar. Don’t get me wrong, I enjoyed being with girls too, but from time to time, I just had this urge or fascination to be with a tranny. Any ways, it had been awhile, and I wasn’t in any sort of relationship at the time, and the thought of being with a tranny again had started to be on my mind. Luckily, this was before Craigslist dropped its casual encounters section, so it was relatively easy to look for hook ups, and being there was a TS/Crossdresser section, I could easily contact one.

I remember looking through postings, hoping to find one that was attractive enough, because as I’m sure you know, many cross dressers and tranny aren’t exactly very pretty. However, as I looked through the postings on Craigslist, I came across one that looked very attractive and she wasn’t asking for a “donation.” She was white or Latina and looked to be young, which I liked, and from her pictures and de***********ion, she seemed to be small framed, which I also liked. I wasn’t sure if she was actually a tranny or a crossdresser, in either case, i decided to contact her.

Like always, with online encounters, there is a hesitation I feel, not really knowing what I was getting into, but eventually I wanted to meet up with her. Her posting simply said, “Come play with me… – t4m,” and in emails when she told where she lived. It happened to be just across town, and when she suggested we should meet up at a coffee shop on that part of town, I was excited. Yea, I knew the area, but had to look up where it was, because it wasn’t a name brand place. As the time came for us to meet up, I became a little nervous. I wanted to make a good first impression, because from her photos, she looked to not only have a pretty face but seemed to have a nice body too, and being I had sent her a few pics, we knew what we were getting into.

I think we were both anxious to meet, I know I was, and as I pulled into the parking lot and searched for her car, there it was. Parking a few spots over and looking her way, she leaned toward me and waved. Smiling, I immediately waved back and when she gestured for me to come over to her car, I quickly got out and went over there. She rolled down the window and after exchanging pleasantries, she said, “Why don’t you come sit in here, it’s hot out there.”

Looking in, I could see she had on a skimpy little black top and a short black skirt that showed off some great looking legs. Smiling, I quickly went around and as I sat in the passenger seat we shook hands. She had a feminine voice and she really was pretty, kind of sexy, which again made me a little nervous. She had a piercing in her upper lip, a diamond stud, and it looked like she had on a lot of makeup that I don’t really think she needed.

She had shoulder length dark brown hair and I could see some dangling silver earrings that accentuated her facial features. As I continued to check her out, casually looking down, I could see she had on one top that was black fishnet material over another black one that was kind of crisscross patterned. Catching myself, I looked up and seeing she was smiling, it was obvious she had caught me too, ur as we looked at each other, she immediately said, “My name’s Kassie.”

Turning slightly to face her, I shook her hand and smiling I asked, “Why do you go by the name of Ms. Cumms?”

This made her smile, and after explaining it was just an AKA, she smiled and subtly leaned over the console, giving me a hug. Surprised, I hugged her too and as we sat back and looked at each other she smiled and said, “I’m a little nervous.”

I was nervous too, and when I told her, she smiled and again leaned over giving me a hug. She was definitely flat chested, at least from what I could see and feel, and she wasn’t as petite as I thought she would be, but in any case, after talking for a little bit she asked, “Wanta go over to my place?”

Of course I did, and after saying, “Yea, sure,” she smiled and told me to follow her.

As I got out of her car, I quickly went back over to mine and as I followed her, I started to worry about what we would do. I knew what to expect and eventually telling myself, “Just be open minded,” I smiled and continued to follow her.

It had started to give me a hard on, thinking about being with her and then pulling into her apartment complex, I tried to shrug it off best I could. Parking next to her, I got out and as we met up in front of our cars, she said, “This is it!”

It was a modest complex with only two floors, and being she was on the second floor, we had to walk up a flight of stairs. She was wearing black high heels and as we turned to go up the stairs, I said to myself, “She’s tall,” as I looked at her from behind. She did have nice legs, and I couldn’t help but look at her ass in that short skirt, and think about being with her.

Going inside now, I looked around, trying to get my bearings, but she had a nice place with a living room, a small kitchen area and a short hallway that must have led to her bedroom. Moving over to the living room area, she said, “Go ahead and sit down, if you want to.”

Smiling, I sat down on the couch and as I continued to look around she asked, “Do you want anything to drink?”

It was the afternoon and when she said, “I can make you something, what do you like to drink,” I asked, “What to you got?”

Pausing, Kassie said, “Are you okay with vodka?”

Smiling, I said, “Sure,” and when she suggested, “How about some cranberry and orange juice with a splash of vodka,” I Immediately said, “A splash?” trying to poke fun.

“Okay, maybe a little more than a splash,” she said, which made me smile.

I now heard the ice maker and after a few minutes, she came back holding two drinks. Handing me one, she sat in the chair that was adjacent the couch and as we talked, Kassie asked, “Have you ever been with a tranny?”

Smiling, not wanting to give away just how much I liked being with trannies I simply said, “Yea.”

Kassie now smiled and asked, “How many times?”

Taking a big drink, I replied, “I don’t know, a couple I guess.”

Looking over at her, she immediately said,“And?”

Smiling, not saying anything right away, Kassie asked, “Why did you contact me then?”

It made me nervous, and when I blurted out, “I thought you were really attractive, and …” but before I could finish she said, “Thanks, you’re very handsome too.”

Smiling, she put her drink down on the table, and then standing up, she came over and sat next to me. As we looked at each other, she said, “Why don’t we go in the bedroom.”

This was what I had wanted but when I hesitated, Kassie took my hand and after a simple kiss she said, “Come on.”

It was obvious she knew why I contacted her, I’m glad she did and as we both stood up, and smiled at each other, we headed toward the back of her apartment. Holding her hand as she led me toward her bedroom, I smiled to myself and then letting go of her hand, I boldly put it on her butt.

Kassie immediately look back, smiling at me as we continued down the short hallway and as we went into the back bedroom, she stopped and turning to face me, she smiled. Kassie then quickly started trying to take off my shirt and as she pulled it up, I lifted my arms over my head. Throwing it on a nearby chair, she again turned to face me. Instinctively, I reached up and as I felt on her tits, she said, “Hang on.”

Letting go and looking at her, I could see she didn’t have anything on under her skimpy little tops, and when I saw her little nipples poking out past the crisscross and fishnet, I looked back up at her. She was smiling and then as she took off the fishnet top, leaving just the black crisscross one that would actually turn out to be a body suit, I reached up again to feel on her tits.

She had a great body, and it was really a turn on to see her, and now as she moved over to the side of the bed, she kicked off her heels. Climbing on, her skirt hiked up, which revealed little black panties. She was very light skinned and when I again looked up at her, and she saw me staring, Kassie undid the zipper. Laying to one side, and taking off her skirt, I could see the bulge of her cock. Kneeling again, she pulled the bottom of her body suit to the side, and when her cock flipped out, I was shocked. She was shaved, which I liked and seeing that her cock was uncut as she stretched it out, I wanted to feel it.

Watching her as she rubbed it, trying to get it hard, i instinctively looked up. She was smiling and when she asked, “What do you think,” I couldn’t help but look down again.

Smiling, Kassie now adjusted her top, trying to hide her little titties, which was unsuccessful. Continuing to watch, she now reached a hand down and unsnapped the bottom of her body suit. Her cock still wasn’t hard, but watching her rub and pull on it again, I too wanted to feel it.

“Oh my god,” I thought as I watched her, and yea she said something to me, but I have no idea what it was.

Kassie, seeing me staring and feeling on my cock through my pants, she took off the body suit. She happened to turn and bent over slightly, as she took off the body suit, and seeing her ass, I wanted to fuck her. Turning back now, she seductively laid down and looking over at me still rubbing her cock, she said, “Why don’t you take off your pants.”