kiyohchan21
12-13-2008, 04:56 AM
It's a bit of a long story, but I do enjoy recalling it and telling it because it brings back fond memories for me. Actually I think I told my story here before, but it may have been a different site, oh well lol. I started "dressing" in the summer of 92 when I was 9 and I was at my friend Angie's house. We went to the same baptist church and I went to her house after services were done. We were playing the usual games we played when I was at her house, which was mostly board games. While we were playing she got an idea in her head and thought I would look cute in one of her church dresses. So after a long time of her bugging me to try it on I finally gave in. I should point out at this time in my life I never had any thoughts of wearing girls clothes, but I knew somehow it was something my parents wouldn't like me to do especially my dad. Anyways she lent me her green church dress, light green cotton panties, white tights with little hearts on them, black shoes with small heels on them, and a matching hairband with little roses on it. I put on the clothes in her bathroom. After I had the clothes on I loved the way they felt. They were so comfortable I loved it so much. I stayed dressed like that the rest of the day. Eventually when Angie's mom came to check on us she looked at me had a look on her face I can't really describe it. I started to apoligize and said I would change back into my clothes. She interrupped me and said how cute I looked and said it is okay to stay dressed in Angie's clothes if I chose to, to which I said I would. She then asked me if I wanted to spend the night I called my mom and asked if it was okay she said it was fine. I also asked Angie's mom not to tell my parents that I was dressing up like this, she never told them and said it would be our secret. She told me if I was dressing like a girl I should have a girl's name and she named me Ashley Lynn. Angie and I went back to playing some games. Angie's mom ordered pizza for dinner and after we ate she asked Angie if she wanted her nails painted pink, she said yes. She then asked if I would want my nails painted too. I said no at first, but then she said she would remove it before I went home the next day, so I said yes. While she was doing my nails she told me if I ever wanted to come over and dress up again I was more than welcome. As you can guess I went over a lot. After our nails were done Angie's mom asked if we wanted to go see a movie. I said yes after I change. She told me that I didn't have to and we could go to a drive in theater, I said okay. Before we left Angie's mom brushed my hair into a more girlish style. When we got to the drive inn Angie convinced me to go get snacks with her at the food concession stand. I was very nervous that someone would know I was really a boy in a dress. When we got there the guy running the stand said "What can I get for you two pretty little girls?" That really shocked me and felt relieved because I thought for sure he would know I was a boy. When we got back to Angie's house we got ready for bed they lent me some white panties with a purple nightie. To this day that was one of the best days in my life. Like I said earlier I started going to Angie's house alot more often and always dressed up while I was there. It wasn't long before Angie's mom started to buy me my own set of clothes for when I visited them. To this day I think of Angie's mom as a second mother I even call her mom and she thinks of me as a second daugther, and she has told me so on many occasions. I consider Angie as a sister and vice versa. Anyways that is when and how I started crossdressing. I would love to tell you girls another story of when I went on vacation with them, but I will tell that story later on if you girls are interested.