Screwed the Bet, Forced to Cross Dress

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Screwed the Bet, Forced to Cross Dress

Hi, um… I have a small problem. My name is Tom. I’m 18 and I, um, made a bet that the Michigan Wolverines were going to beat the Tennessee Volunteers in football.

Well, it got out of hand and I either pay $250 all around or live like a woman for a week- panties, bra, makeup… the whole thing. I don’t have $500 so I’ll go with the woman thing. I need advice. I’m not asking friends because I want to keep it between us three guys. Please help me. -Dragged to Drag (Franklin, TN)

Sweetness, there are two things you must keep in mind:

1) The only sure thing is that most bets have a 50-50 chance of losing. If you are not prepared to be on the wrong side, don’t bet in the first place.
2) There’s nothing uglier than a macho man dressed in drag.

The only advice I have is find a sister, best girl, or any other female with a sense of humor and borrow some clothes. No one said you need to look like a femme fatal- jeans and a t-shirt, some lipstick, and goop in your hair will suffice. Any tranny will tell you that Payless goes all the way up to a size 13 in women’s shoes… find something you can walk in!

Then it’s your decision to either stay in the house all week and watch daytime TV where you can listen to more fools in a similar predicament to yours or go out and have fun with it! At least you’ll have a zany story to tell your kids down the road.

Hope you’re not pulling my leg with this email, or I’ll have to tell my local she-male, Helga and the Angry Twelve Inch.

–January 5, 2002

Published on January 05, 2002

Sharon Haver

Resident fashion expert- With just about 20 years experience in the glamour industry as a New York-based photography fashion stylist, syndicated columnist, contributing editor, lecturer, on-air television/radio fashion expert, and founder / editor in chief of FocusOnStyle.com. Sharon Haver knows the modern-thinking woman wants easygoing style that suits her individual needs, spiced with just the right amount of flip and wit to make it personal.

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