That First Big Leap

My former sister-in-law's fashion sense and occupation was the birth of my early experiments with crossdressing. She worked at a Parklane Hosiery outlet and wore pantyhose all the time. I was already obsessed with a middle school teacher’s hosed legs so one thing led to another.

One Thanksgiving she showed up at our house way overdressed; little black dress, strappy heels and sheer black pantyhose with a back seam and bow on the heel. Slightly embarrassed, she went into my bedroom and changed into more casual clothes. As soon as I could, I made a beeline for those pantyhose and held them in my hands. The feel of the sheer nylon on my fingers was an utterly amazing sensation. It was like some mysterious key to a kind of femininity I desired. I desperately wanted to put them on but thought better of it.

Later that year, I spent the summer at her house. When my brother and sister-in-law were working, I went through her lingerie drawers marveling at her slips, bustiers, garter belts, stockings and pantyhose. I would try them on and admire myself in the mirror, thinking of the glamorous women on the soap operas my mom watched.

Watching her get ready for work became a habit. I loved watching her apply her makeup and smooth out her hose before going to work. I began walking around the house after they left, fully dressed in her work outfits with a little bit of perfume on my wrist. Wobbling on heels, I would sit in the living room crossing and uncrossing my legs, feeling the wonderful sensations of hosiery and silk. She dressed so feminine and stylish and her hosed legs were almost always on display. I wanted to feel as feminine and attractive as she looked to me.

That was really where I unlocked something inside me that still to this day doesn't feel unnatural at all.