A Woman's Wager

"I don't really know what to say to that, Jake," said Ed. "If you don't mind me saying so, and I mean no offense to your inner beauty, but it's all a bit bizarre to me seeing you in drag. There's just no way I'd ever dress up as a woman. Now that I recall, though, there was that Halloween party I attended so long ago where I dressed as Marilyn Monroe and if I say so myself, I looked pretty hot."

"I bet you did," said Jake. "You'd make for a pretty woman. You have a nice figure," said Jake looking around at Ed's ass. "Say, speaking of Marilyn Monroe, don't you just love this flared dress that I'm wearing? Doesn't it make me look skinny, in the way it pinches in at the waist and flares out at the hips. You think that it wouldn't but it hides my hips," said Jake looking down at himself before twirling around. "Dressing like a woman makes me feel so sexy and I like the way men look at me."

"Don't do that, Jake."

"What? Don't do what?"

"Don't twirl around like that. People are starting to stare and I think that elderly lady, the one who left our aisle a moment ago, is calling for the manager," said Ed taking another step away from his effeminate friend. "Listen, Jake, let me give you a newsflash," said Ed with a laugh. "Men don't look at you because they think you look pretty or that you look sexy. They look at you because they've never seen a 6'5" man in 2" pumps dressed as a woman before. To be honest with you, you don't look anything like any women I've ever seen in my life."

"Oh, well, okay, that's good to know," said Jake suddenly looking sad, embarrassed almost. "I don't care. I still feel pretty and that's all that matters, how I feel."

"I'm sorry, Jake, but you look ridiculous," said Ed. "You're as tall as the shelving in this place. Maybe if you shaved your mustache, you could at least fool the toll booth attendant on the parkway, but unless you're in a room full of sightless people, everyone knows you're a man, a cross dressing man. Trust me."