As long as I can remember, i always coveted my mother's and sister's clothes, and started -er- sampling them when i was around 12. Thanks to my mother's wardrobe, I quickly discovered the pleasures of slips, hosiery, and high heels.

For me, I would try my sisters underwear on when I was a young and I was overwhelmed with emotion. Now I have never told my sister but at that time it meant everything. We all need friendship and being honest to the core is the best solution.

May 13, 2020 · A few years later I dressed up a younger friend in his sister’s clothes, subconsciously wishing it was me who was being feminized. That afternoon ended abruptly when his mother returned and ordered me to leave their house.

Being the same size, I used to dress in my sister’s clothes a lot growing up. She would always figure out though no matter how hard I tried to put stuff back the same, even washed etc. it largely ruined our relationship and fueled her life long hatred towards me.

Unfortunately, I didn't have any sisters, but my mother made me dress in my girl cousins' hand me downs and curled my hair just like theirs. I even had my ears pierced. I have many fond memories of wearing frilly dresses and having ribbons in my hair.

Since then I have been locking myself practically everytime secretly inside bathroom browsing and playing with my sister's clothing and taking them out to wear it. I would tried out every bits of my sister's clothing not to mention even her underwears panty.

I still to this day love to wear my sister's clothes every chance I get. Wearing her things is so sensual to me, and creates extra 'excitement' in me.

Sep 1, 2021 · Me and my sister would play dress up when we were little, but the first time I started doing it on my own was when I was around 14ish. I would sneak into my sister's room and steal her friends clothes they would leave and try them on. Bought my first clothes after I told my wife about it cause she wanted to see. Around the 6-8 yo time.

Yep. I would secretly wear my older sisters dresses and heels whenever I was home alone when I was 13 or so years of age

Oct 22, 2016 · I had tons of mini skirts in the wardrobe, and bear in mind, when I DID wear shorts as a boy, I wore them to my knees. To wear a skirt that barely made it down to mid-thigh was humiliating. I remember going to school and guys were wolf-whistling at me.