The Boy Meets He-She

Boy Comics, aka Boy Illustories, was a Golden Age comic book (1942-1956) with a revolving cast of boy heroes: a boxer, a pilot, a Tarzan clone.

But the star was Crime Buster, aka Chuck Chandler, a muscular teenager who pulled his underwear over his school hockey uniform, added a blue cape and a monkey sidekick, and set out to foil super-villains, notably the Nazi Iron Jaw.

After the war he dumped the cape and white shorts and wore a standard hockey shirt and blue pants.  He started having high school adventures involving bullying, sports, and stealing test answers from the deans' office.

But he kept the monkey sidekick.

His oddest nemesis was "He She," who appeared in Boy Comics 9 (1943): not a transgender person, but a "half man, half woman," actually male on one side, female on the other. "The deadliest of the species is the female!  The strongest of the species is the male!"

He-She marries a woman for her money (I'm not sure how the courtship worked), and when she discovers he-she's secret, kills her -- and escapes easily just by changing his profile.

The confused Crimebuster then says "Pardon me, Ma'am, did a villain just run past here?"

Twice.