Unless your mother dresses you up in girls clothing at age 3, I would assume about age 11 or 12 years old for most boys . I was probably an exception. I wore my first pair of panties at age 5. I was staying at my grandmother's for the summer. One day, she left to go to a neighbor's house to borrow some flower and chat for a few minutes. At this time I saw my chance to go into her room and look in her undies drawer. Since I've been think about wearing girls undies for the last several months, this was a good opportunity!
I looked in her drawer and fondled several pairs of panties, finally choosing a red pair. I dropped my shorts, took of my Jockey shorts and proceeded to put on her panties. Even though grandmother was very petite, wearing size panties 5 panties they fell off. So much for my first experience wearing panties. I carefully rearranged the panties in her drawer and left the room very disappointed.
During the following weekend we went to the house of a friend of my grandmother's. Sally had her grand daughter staying with her. Nancey was age 7. We liked each other immediately and had a nice time playing games. One afternoon, grandmother and Sally left the house to going shopping for a few minutes. At that time, one of Nancey's friends came over and wanted to play. I told them that I was tired and wanted to watch TV. I figured that this was the time to go Nancey's room and look at her undies.
I went to her room and looked in the drawer where her undies were at. I pulled out a pair of white panties, went into the bathroom and tried them on. I got a feeling of excitement that I never felt before . I put my Jockey shorts in my pocket and went into the living room to watch TV. Grandma and Sally came home a few minutes latter from shopping non the wiser.
We ate lunch, stayed the afternoon and went home in the evening. That night I went to sleep wearing Nancey's panties and dreaming about wearing more of them. The next morning grandmother woke me up and asked me how I liked our visit. I told her that I was looking forward to going to Sally's house even staying for a few days.
I looked in her drawer and fondled several pairs of panties, finally choosing a red pair. I dropped my shorts, took of my Jockey shorts and proceeded to put on her panties. Even though grandmother was very petite, wearing size panties 5 panties they fell off. So much for my first experience wearing panties. I carefully rearranged the panties in her drawer and left the room very disappointed.
During the following weekend we went to the house of a friend of my grandmother's. Sally had her grand daughter staying with her. Nancey was age 7. We liked each other immediately and had a nice time playing games. One afternoon, grandmother and Sally left the house to going shopping for a few minutes. At that time, one of Nancey's friends came over and wanted to play. I told them that I was tired and wanted to watch TV. I figured that this was the time to go Nancey's room and look at her undies.
I went to her room and looked in the drawer where her undies were at. I pulled out a pair of white panties, went into the bathroom and tried them on. I got a feeling of excitement that I never felt before . I put my Jockey shorts in my pocket and went into the living room to watch TV. Grandma and Sally came home a few minutes latter from shopping non the wiser.
We ate lunch, stayed the afternoon and went home in the evening. That night I went to sleep wearing Nancey's panties and dreaming about wearing more of them. The next morning grandmother woke me up and asked me how I liked our visit. I told her that I was looking forward to going to Sally's house even staying for a few days.
