Wikipedia defines sissy this way: (derived from sister; sissy baby, sissy boy, sissy man, etc. is a pejorative term for a boy or man who violates or does not meet the standard male gender role. Generally, sissy implies a lack of courage, strength, coordination, testosterone, male libido, and stoic calm, which have traditionally been important to the male role. A man might also be considered a sissy for being interested in traditionally feminine hobbies or employment (e.g., being fond of fashion), displaying effeminate behavior.
Sissy is, approximately, the male converse of tomboy (a girl with masculine traits or interests), but carries negative connotations. Even among gay men, behavior thought of as sissy or camp produces mixed reactions.
Growing up, our neighbors across the street had a niece that would come to the “country” to visit for several months every summer. Ann and I would climb trees, sit in the limbs, cut our initials in the bark and play and run in the woods. She was a “Tom Boy”, as they called girls like that back then. She wore rolled up jean with oversized shirts, and only for church on Sunday did I see her in a dress (against her will). I saw a lot of myself in Ann. It did not take me long to determine society has more tolerance for tomboys than it does for sissies.
I loved cooking with my grandmother, read woman’s magazines and studied the woman’s section of the Sears Catalogue at every chance. I hated that girls could openly be a tomboy and were even spoken of as being cute. Why couldn’t I be both? As I got older, I had to accept that this was not going to be something I was going to outgrow. To adapt, I created an almost dichotomous personality.
I became well-adjusted in the male world. But in order to express what I regarded as my feminine side I would at times dress feminine. In that way I could explore, temporarily, the feminine capabilities I felt. Reluctantly, I would always return to the safely of my masculine identity. Finally later in life I was able to be the feminine person I needed to be. Sadly, I spent a great deal of my young adulthood trying to run away from the femininity that was just below the surface.