Crossing Gender Lines (Prologue)

Prologue: A Different Man

From a young age, I knew I was different from all the other boys. I grew up always crushing on girls, from elementary school to kindergarten. I never believed in cooties, never thought girls were gross, and always had female friends.

I was curious about girls from the beginning, which I assume now is because they’re different from boys. The different clothing girls wore always interested me, and I could never understand exactly why there were unwritten rules about what boys could and couldn’t wear. Girls were allowed to wear boys’ clothes, but boys weren’t allowed to wear girls’ clothes, and it never made sense to me.

My two aunts, who were both quite attractive, were always of interest to me when they visited our home. Not because I was intent on my aunts themselves but more because of what clothing they brought with them. I used to sift through their swimsuits, bikinis, and underwear whenever they would come over, worried about getting caught because society made a boy feel guilty for being interested in girls’ clothing.

It wasn’t until my own sister hit puberty that I had solid access to girls’ clothing. There was no way I was going to investigate my mother’s clothing, as that seemed extraordinarily weird to me. My sister, however, was one of my peers, only two years younger than me, and it felt okay to be curious about what she wore.

Throughout high school, I had lingering fantasies about wearing women’s clothing, especially their undergarments. It was always the bras, panties, bikinis, swimsuits, and other tight-fitting clothing that piqued my curiosity. Lingerie and stretchy fabrics were the central focus of my fascination with women’s clothing, as it was primarily the stuff that a boy could never get away with wearing that got my attention.

My sexual proclivity with women’s clothing began when I was a teenager. Afraid of shame and embarrassment if I took my sister’s clothing or was seen purchasing such clothing from a store, I sunk to a more secretive way to obtain such things. It started with the ease of lifting items from thrift stores and escalated to shoplifting from department stores and mall clothing stores.

With the advent of online shopping, I was able to procure items for my fetish without shame by having them delivered to the house.