His first published art was in 'Fated for Femininity', a 1960 Virginia Prince/Transvestia novel that tells the story of Lennie Parks:
Lennie Parks was a great yell leader at his former school. He was surprised that there were only girls at the tryouts, but he easily showed them all up with his acrobatic performance.
The other four members of the squad were girls and they resented the skill he displayed in their practices. Their uniforms arrived for their first official appearance - blue satin overall jumpers, frilly white silk blouses, blue sox and white girl's shoes.
"I won't wear that sissy outfit," he said.
Mona, the head cheerleader, shook him forcefully and said, "You little fool, it's too late for us to get anyone else. Will you put this uniform on, 'Linda', or do we have to dress you?"
Soon thereafter, in order to make him an even more convincing cheerleader, the squad took Lennie to a beauty parlor for a permanent wave.
In advance of their next official appearance, the giggling girls not only fluffed his curls into place, they also pinned him down and applied powder, rouge and lipstick to the squirming boy.
When Lennie arrived for the next game, he was horrified to see how Mona was dressed.
"Darling, I'm afraid I forgot to tell you that we had a last minute change in our uniform."
"Is . . . Is it . . .?
"Oh yes, it's like mine." She was wearing a bright blue slip-on sweater and a cream colored flannel skirt. "At the last two games we all wore trousers for your benefit, but this time we are all wearing skirts, for our benefit."
The girls also trick him out in stuffed bra and panties. He doesn't do any flips that day. He performs carefully, trying to prevent his short skirt from flipping up.
More or less as a joke on him and Mona, his classmates choose him as homecoming queen. Lennie is exceedingly embarrassed to have to appear at the dance in a dress in front of his classmates some of whom are now wondering about his gender.
From here forward Lennie/Linda wears dresses more often until his classmates think he was a girl all along.
Mona is a bit of a sadist who enjoys dominating and punishing the boy/girl.