So I suddenly had this bag of my sister’s clothes, essentially an entire second set of clothes, and they all fit me comfortably, but I didn’t know what I would do with it. I certainly wasn’t going to just start wearing them. Not only was I not particularly interested in wearing women’s clothes, but I knew of course my sister would recognize her clothes if she saw me in them.
There were a few things I knew I could wear without anyone noticing, like socks and underwear and t-shirts. There were no socks in the bag, but there were bras and panties and shirts.
I was 14, and the idea of wearing my sister’s panties without anyone knowing was strangely exciting to me. It wasn’t out of a desire to cross dress, but just the fact that there was something naughty and yet appealing about it. And it helped that my mother had recently bought me some underwear that was a size too small, so my sister’s underwear was actually a better fit and more comfortable than my own.
So it started very slowly at first. I would sleep in her panties sometimes, but then put on my own underwear during the day. Soon I was sleeping in them every night and then occasionally even wearing them during the day. I was very pleased with myself to be in my sister’s presence wearing her panties without her knowing it. As time went by and I realized no one was really paying any attention to my underwear choices, I became much more comfortable with it.
By age 16 I was wearing only panties. I had a few pairs of men’s underwear for situations where I would need them like doctor visits, but for the most part my sister’s panties had become my normal everyday underwear. When I had to wear men’s briefs, they felt weird on me.
This created a whole new problem I hadn’t really anticipated. All of those panties I had taken from her were now several years old and were getting worn out. I was at the age finally where I had a driver’s license and a part time job that gave me a little bit of income, and one day something dawned on me that I had never realized until that moment. I could actually just go out and by my own panties.
It was like a whole new world had opened up to me. I remember how nervous I was the first time I went panty shopping. I was walking around the lingerie department of a chain store and sure that someone would complain to management that a teenage boy was looking at the panties. I bought some packaged panties, which was all I really knew about because it’s what my sister wore, and was so excited to bring them home.
This soon developed almost into an addiction. Over the next year I kept buying new panties every chance I had. I soon had literally over 100 pairs of them. I’d also become almost too comfortable with wearing them, and was almost no longer hiding it anymore.
My underwear drawer was filled only with panties, and at any given moment you’d be likely to see several pairs just casually laying on the floor of my room. If I went to take a shower in the bathroom I shared with my sister, I’d take a clean pair of panties to put on. Often I would just hold them openly in my hand as I walked to the bathroom, not even concerned someone would notice.
We went on a family vacation and I packed only panties, which I left practically visible in my open suitcase for the whole trip, and no one caught on.
I realized that I wanted to get caught. I wanted it out in the open. I wanted to not feel like it was something I needed to keep hiding from everyone. I was a normal teenage boy who happened to like to wear women’s underwear.
Loading comments...