My first time with my friends dad. - Sex Stories

My first time with my friends dad.

My name is Tessa. I often walk around the mall in my short dress and high heels, I'd stand around hot guys to get their attention, and I do most of the time. But I'm not exactly your average girl... I was actually born a boy and my name was Robert. But, I never felt like I was ever truly meant to be one, and the only thing that categorized me as a boy was my private area. I can still remember the first time I felt more like a girl, I remember like if it was just yesterday... I was only in the second grade and my straight blond hair had already grown slightly passed my shoulders. One day while mom took my s!ster out shopping, leaving me with our lousy baby sitter, I locked myself in my s!ster's room and I wore one of my s!ster's dresses which fit me just right as I stared at myself in the mirror for several minutes. I also wore her panties underneath so they would hide my "ugly" boy parts. I laid face down on her bed and daydreamed about what it would be like to walk around the streets wearing this dress, would people think I'm really a girl? I soon found my small circumcised penis was becoming excited at this thought and as my body shifted around on the bed it felt really good. I continued to think these naughty thoughts of wearing this frilly pink dress in public, me a boy... I was feeling a sensation I had never felt before down there as I sort of humped the bed for a little while until I thought I was going to pee on my s!ster's dress so I stopped but by that time I was ...

... moaning and panting as I was having my first dry orgasm. I hadn't really liked any boys at school until I was in the fifth grade, but there was this one thing that sort of made me like the older boys, or in other words, men. It happened a few weeks after my tenth birthday, I was at a friends house with a large group of k!ds and we were all playing hide and seek. We all scrambled to find a spot to hide but I decided to find a place where nobody would look, so I headed upstairs, even though we were only supposed to play downstairs. I quickly climbed up the stairs and opened the door to one of the rooms which just so happened to be my friend Jamie's dads room. I found his dad half naked wearing only his boxer shorts. He said, "Hey, your Karen's k!d... Bobby right? You sure have grown haven't you... You're a big boy now huh?... " I looked at him out of surprise since I had only seen him like twice before that day and he was now maybe in his early forties. He looked at me up and down saying, "Why are you here Bobby? Shouldn't you be down stairs with the other k!ds ... Hmm?" I nearly trembled from how nervous I was thinking I would be in some kind of trouble and I managed to say, "Well, mister Walters I..." As I said this I saw him approach me getting closer and he reached behind me to lock the door saying, "Call me Dave.". Soon he was standing in front of me and I saw his hand reach down as he placed his hand on the front of my shorts right on my private area. Taken by surprise I ...