Chapter 1: The Deal

I looked at my sister and couldn't believe what she'd just asked me to do. "What are you saying?" "I want you to go with me and Colin to his frat's Halloween party! You'll have fun!" She said, totally skipping the strange part.

"No, what was the other thing you said?"

"I want you to go as Colin's friend Rob's date. No strings attached. Just a date."

"Kimmie, has being a sorority girl bruised your brain? Let me point out a few things: A- I'm not in College; B- I don't date College men; and C - I'm A GUY!!"

"Look, I'm not asking you to 'show him a good time' or anything, just pretend to be a "High School senior for me for one night, go out with him, then never see him again.

Besides, it's not like you've never dressed up like a girl before. And don't tell me you didn't like it, 'cause I know it's true. You even looked good, cute even."

That was true; I had dressed like a girl on a few occasions. My sister used to give me "makeovers" when she herself started experiments with makeup and girls clothing.

And there was one Halloween where I went out dressed as a girl, a Cheerleader to be exact. I looked so much like a freshman cheerleader (and I was an Eighth grader), that one of my sister's junior boyfriends tried to get my phone number. It was the thrill of fooling this guy that led to some of my more recent "cross dressing" experiments, the ones she doesn't know about. Like how I've mastered the art of passing for a female, using makeup padding and the right underwear. I've tested my skills a couple of times; one time the cable guy was met at the door by a sexy, flirty co-ed wearing really short shorts and snug little tank-top.

I know the guy was completely fooled, because he invited me to meet him for drinks. Poor guy, I'm only 16! (Though I told him I was 22, and he believed it!)

My favorite memory of "dressing" was at this year's Youth dance at the youth center. I convinced my parents to let me go alone to the dance. They went to dinner; I went deep into my mother's closet. I found a sexy little cocktail dress, hose and shoes. I took a cab to the dance, with the cabbie checking me out all the way! At the dance, I was astonished! I figured they would think I was a High School girl, or maybe a College intern working at the center, but almost everyone thought that I was one of the 20ish year old community mentors for the local girls. People would tell me how great it was that beautiful, young woman would take time out of her life to provide a good role model to troubled girls in our community! When the women chaperones said it, they meant it; when the men said it, they were trying to check me out! My former soccer coach even slow danced with me! And I kissed him goodnight (O.K. so there was more than 'goodnight' kissing going on then.) Since then, I have been expanding my wardrobe and looking for another opportunity to "dress up". You see I wasn't bothered by the concept of going out dressed as a girl.