The Shemale Flapper

It started out as a random face I drew with two different eyes and different lips. I decided to make it showing two types of Flapper styles on the same person. (Mostly in the hair and the eyes) THEN I came to the conclusion that the girl (The main one, not the one on the wings) in this picture is a shemale.

Her story goes:

Her name was Jon Kemper, and in the 1920’s when prohibition was enforced, he frequented speakeasies.

One night, Jon saw the most beautiful flapper girl dancing with some other flapper. All night he watched her and he was mesmerized by her beauty. By the end of the night, he was confident and planned on going up to talk to her, maybe ask her out, but he stopped dead in his tracks when he saw another flapper grab her and kiss her. She didn’t fight either. She rather enjoyed hi.

Embarrassed, he left the speakeasy and didn’t come back for about a week. But when he did come back, he watched her again. His heart ached at the sight of the beauty he’d never hold.

A few hours late, and very tipsy, Jon got the bright idea of dressing up as a woman to attracted the girl he’d been watching. Lucky for him, he wasn’t a big manly man and with the right makeup, no one could tell it was him.

The day he bought some pretty dresses, a couple bras, some makeup, a couple wigs and some jewelry. He shaved his arms and legs stuffed his bra up with whatever he could find that would feel realistic. He sat and tried two styles. One was a dramatic style like Louise Brooks, with the straight, bobbed wig. The other style was more soft yet wild and still a little dramatic, like Clara Bow. This was the one he chose. It seemed to fit him a bit better.

That night, when he entered the speakeasy, all eyes turned to him. Even his drinking buddies didn’t recognize him. The girl who he had watched took notice too, and invited him to dance. The entire night they danced and talked and had a wonderful time.

This went on for a month. It got to the point where he and the girl would go out shopping together and just be together. His dream was coming true. He was finally near her.

One night, as he left to go to the speakeasy, the girl caught up with him and pulled him into an alley. There she kissed him and told him how much she loved him… Or at least how much she loved the woman he pretended to be. Guilt took over him. He was misleading her. He hugged her and told her the truth.

When he was done explaining, she looked him in the eye, took off his wig and kissed him again.

“It’s all right.” She said. “I go both ways.”

Wow, that story sucked. TT__TT