When I was a little boy, around the age of 3 or 4, I always wanted to wear diapers. I remember going over to my auntys house and stealing some diapers she had by her front door, she ran a day care and always had diapers. I remember taking some girl pull ups, I put them up my shirt shortly before we left and when I got home I put them on. Wow, I remember feeling the tight plastic as it wrapped around my butt and front section. It wasn't quite my size, but it did the job.
A year later my parents went on a trip to Las Vegas and I had to stay with my aunt. I was potty trained, but I don't think her kids were. I remember her saying that because she didn't know if we were potty trained that she would have all the kids in daipers; I was so excited. I remember standing in line and getting diapered. Aunty was so getnel, making sure to rub me with cream and powder me well, and then wrap me in a sung diaper, I felt so loved.
Fast forward 7 years,I am now 14. My mom and dad divorced and my mom got custody. I am an only child and my mom is very protective of me. I want to play sports badly, but she never approves. I spend a lot of time alone, as mom works a lot of overtime at work. I usually spend most of my time watching T.V and playing on the internet.
One day I remember watching Oprah on T.V and the topic was cross dressing. I was only 14, but it intriged me, so when my mom went to work, I went in her room. I put on panties, pantyhopse, and a dress and lipstick. I also put on a bra, I had to stuff it with toilet paper so it would fit.
By the time I was all dolled up, I felt pretty good. But just when I got downstairs, mom came home because she forgot her purse. I would never forget the look on her face. She put me over her knee right away and spanked me until I was crying, which didn't take long. She allowed me to run up to my room unitl she could figure out what to do with me.
About an Hour later she came up to my room and explaind to me that she wasn't angry with me for dressing up in her clothes, but a little upset because I wasn't shareing my feelings with her. I told her about the Oprah show, and that I got curious about what if felt like to dress as a girl, and she didn't get mad.
Surprisingly she said we were going to go shopping. When I told her I didn't want to go, she said I really did, but I didn't want to say so. I asked her what we were going shopping for, and she said I needed some outfits if I really wanted to know what it felt like to dress like a girl. When we got to the store we started out in the panty section. I didn't know what size I needed, but mom did. I was a size 5, just the size that was perfect mom said for me to get some really good deals on clothes.
After putting a few different styles of panties in the shopping cart, mom said I needed some mini skirts. I rally didn't want anything short, but mom insisted. We got some black mini skirts, and a few other different colors, and then we went for some shoes. After trying on a few different pairs, mom decided to get a pair of mary janes and a pair of sandals. After getting some pantyhose and a few other excessories, mom took me home.
When we got home she told me to get in the shower, I was still curiouis, so I followed her commands. She handed me a razor and shaving cream, and told me that girls don't have any hair, so I better get rid of it. It took me a while to get rid my my hair, but when I was done I was smoooth, and I liked the way it felt. Soon after mom told me to come to her room, she helped me get dressed in a tight skirt, panty hose, a bra (with padding), a sweater and some mary janes. She then showed me how to aplley make-up. When she got done I must admit I looked pretty good.
Mom told me that she always wanted a girl, and that as long as I wanted to expermient, she would always be there for me; She suggested that if I want to be a girl, she call me Jackie instaed of Jake, I thought that would be OK. Sometimes we would go shopping for clothes and she would ask the cashier if she thought her baby girl was the most adorable thing in the world, the cashier would always smile and and say of corse.
Mom later found out that I also liked to wear diapers from time to time, so she started to buy me some. Some days she would dress me in a short skirt and a diaper and a nice shirt, and take me to the mall. My diaper would be sticking out, and most of the time it would be wet, but mom told me not to worry about it. She told me that babys grow up so fast that mommys don't mind changing diapers, even if their baby is a little older. Sometimes she would have to change me in the girls bathroom in public places, but mom never let the negative comments she got from other women effect me, she told me that not everybody has a girl and that sometimes they get jelous. I will never forget the times I had as my mommys little girl.