My name is Ryan and I turned eighteen years old a week and a half ago. I live with my mom and s****r in an apartment in a pretty nice part of town. My dad left when I was little and I know that living with two girls had the effect on me that it has. A couple years ago when my mom and s****r were at work I tried on some of my s****rs cloths and make up and was surprised by how much doing it turned me on. I always got teased at school by guys telling me I had a very feminine face. I have medium length dark hair and I am thin and not very tall only five foot five so when I put on my s****r cloths and makeup I was surprised by how much of a girl I looked like. After that day I did it all the time and then started shaving my body so I was smooth. I started watching and got really into Shemale porn jerking off to it all the time. I would start stealing my moms dildo and using it when her and my s****r weren't home. I of course kept all of this a secret but after awhile I wanted more then just using the dildo and watching porn videos. My friend told me about Craigslist so I went on there not expecting anything but made a post looking to have sex while dressed as a girl and attached a picture. Twenty minutes later I had a response by a guy names Marcus who said him and his two friends were looking to meet up at a hotel that wasn't to far from my house. I was so nervous but agreed to meet them and after my mom and s****r left I grabbed some of my s****rs things and makeup put them in a bag and headed to the little hotel.
I arrived and went into a bathroom in the lobby and put on all of the cloths a black thong, a pair of pink sweat pants that said "Pink" on the ass in white letters and a tank top. I put on some eyeliner and made my way up to the room. I knocked on the door feeling my stomach turn when a large black man opened the door with a smirk inviting me in. His two friends were sitting at a table playing cards and drinking "OK" one of them said with a grin looking at me.
