Started crossdressing at an early age. Have a sister that was older, but we were similar in size that I could wear her clothes. She had dressed me up in her skirts, dresses, and school uniforms several times. My mother had seen us playing several times and commented that I looked cute as a girl.
Then one day my sister didn’t want to play dress up any longer. I still liked dressing up, so continued to do so in secret. My sister had some hi-cut stretchy nylon panties I found in her panty drawer one day and felt I just had to try them on. They fit me perfectly, and I instantly fell in love with them.
I had more breast-tissue than most boys, so I could fill out her old training bra and didn’t need to stuff her bra very much. At the time, I didn’t know what was happening, but I hoped my breasts would continue to grow, so I could wear a bra like my sister did. I preferred wearing girls’ clothes and just felt better wearing skirts and dresses.
When alone, I would wear her panties along with her old bra, blouses, skirts, socks, and heels or wear one of her dresses and got quite good at zipping myself up. I practiced walking in heels and got quite good at it. I looked forward to being alone, so I could get out of my boy clothes into the clothes I preferred wearing.
I was afraid to talk to my sister about it because I didn’t know how she’d react to me still dressing up without her knowledge and wearing her bra and panties. I liked her panties so much better than my own underwear that I started wearing her panties everyday. I liked being able to wear panties, but soon someone found out.
My mom was going through some clothes one day and stopped me asking for me to try on some things to see if they fit. She handed me some shorts and I took it and turned to go to my room to try on. I was planning on taking off the panties and putting on my underwear and coming back out, but she told me to hurry up and do it right there.
I was wearing my sister’s white hi-cut stretchy nylon panties that day and even though they were plain, I knew they couldn’t pass for my underwear. I was worried about changing in front of her and I tried to get her to let me try them on privately, but she insisted that I do it right there. I hoped my shirt which was long would hide the panties.
Trembling, I unbuttoned my shorts and slid them down and stepped out of them. I was getting ready to try on the other shorts when she stopped me and gave me a shirt to try on instead. She had me take off my shirt and I was standing there embarrassed wearing only my sister’s hi-cut panties. I felt naked.
My mother did the laundry and shared that she had realized something was wrong because my sister had been using about twice the amount of panties she should have been, and I hadn’t been using any underwear. Her suspicions confirmed, she called my sister in so she could see me standing there wearing her panties. My sister didn’t seem mad about it, but did looked shocked to see me wearing her panties.
My mother seemed upset and asked why I was wearing my sister’s panties. I tried to explain about liking the way her panties fit and felt and about liking them better than my own underwear, but that must have been the wrong thing to say because my mother became angry and screamed at me telling me that panties were only for girls. She grabbed a belt and had me bend over and then started slapping my bottom with the belt all the time screaming about me wearing my sister’s hi-cut panties.
Me dressing up wearing skirts and dresses had been okay, but me wearing panties was terrible to her. I didn’t understand why a boy preferring to wear panties was so terrible, but learned that some women were not understanding at all. I told my sister that I was sorry for sneaking into her things and she gave me a hug.
I found out that my sister didn’t like those stretchy nylon panties very well and preferred cotton panties. She later gave a few pairs of her stretchy nylon panties to keep, and I was careful to hide it from my mother who remained a bit suspicious of me and I knew she didn’t understand. When my sister switched to cotton panties she wanted to wear, I was able to save the rest of her stretchy nylon panties from being thrown out.
Submitted by Wendy