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Sissy in Sotckings

By Sissy

Every morning when he wakes up, Robert looks out the window to the house across the street. It’s the house where his mistress lives, and he knows how lucky he is to have her so close these days. It didn’t start out this way, but now, he’s totally under her spell.

He goes to the closet and selects an outfit that he knows she’ll like. Sexy bra and matching panties, stockings, pencil skirt and silk blouse, modest heels. He puts on the lingerie and lays the clothing across the bed for later.

First, he must put on his make-up. He has a lighted vanity with all the necessary supplies laid out in perfect order. Primer, foundation, contouring cream, blush, eyeliner, eyeshadow, two kinds of mascara, brow pencil, lipstick. He knows more about makeup than most women. He knows how to apply it with expert hand to look sexy and yet not overdone. Putting on his face is pleasurable, a freeing experience that lets him be who he really is.

A sleek pageboy wig completes the process, and then he steps into the freshly pressed clothes and looks in the mirror.

All in all, he’s happy. Pleased that he can so easily pass. On the street, men always give him the approving once over and he knows they see him as a sexy woman.

With confidence in that knowledge, Robert crosses the street to Monica’s house. She’s the one who has made this fantasy life of his come true. Oh sure, he’s always been able to dress and to pass, but to finally share it with someone who understands is all he’s ever wanted.

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