First Time In Girl's Clothes

I had been trying panties on since I was eleven. That was a daily ritual for me. Coming home knowing I'd have maybe 45 minutes before my sister came home. I'd go to her room or my mom's and get a pair of their panties. I'd model them in the mirror for awhile but always put them back. Some time around thirteen I got brave and would leave them on under my clothes and also sleep in them and eventually also wore them to school. Around the time I was fourteen years of age my sister had left home but left some of her old clothes behind. I had started experimenting with her shorts, shirts,blouses and even skirts. But it was these two pairs of jeans that I absolutly loved. They were quite form fitting. Even though I was a boy I was a bit shaped in the hip and butt area. One pair was a basic Wrangler 5 pocket ladies jeans and if you evertried that brand or seen a lady in them you know how tight they are.. The other was a pair of Rocky Mountain jeans which had no back pockets. You know that rush you get first time you secretly try on panties? I got that same feeling with the jeans. As with the panties ,in the beginning trying on the jeans was a secret thing and then it was back to boy clothes but by then the sessions were a bit longer. I would put on panties and something of my sister's sometimes shorts, sometimes the jeans or some of the khaki stretch pants she had, and I'd add a top to that. I was not good at make up so I'd just put on lipstick. I would walk around the block practicing my girl walk. Eventually I got brave and on a few occasions wore my sister's jeans to school with a regular shirt. There was this one thing that happened in which my little outtings stopped for awhile. There was a carnival in town but my mom had to work double shift. I figured I could go and be back in time before she returned. I put on some panties and the Rockies with a top. I put on some light make up and lipstick since I was better at it now. My hair was longerso I fixed it up a bit and added a cap. Any way at the carnival I walked around a bit.Rode the rides then headed to the area where they had music.To get tothe section that had my music I had to walk through a crowd. At some point I felt some man pinch my butt. My voice was not feminine so I said nothing. A few minutes later he caught up to me again this time fully grabbing my behind. All I did was jump in surprise. I ended up just going home. That event was scary enough for me.
chris76 chris76
31-35, T
3 Responses Jul 27, 2010

Sounds like you had some truly extraordinary experiences during your teenage years. Unfortunately, I never had any sisters so I was mostly out of luck.

But you must have felt so pleased that you butt in panties and jeans was so attractive like any girl honey<br />
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roxanna

Those love pats must have gotten the adrenaline flowing.