My first experimentation with cross-dressing was not self induced. I was 4 years old, and my Kindergarden class was holding a very special event that devoted an entire day to all of the children embracing clothing of the opposite gender (I'm not joking). I look back at this and wonder how this was at all possible, especially in a largely Christian community. Somehow, both my Mrs. Carson and the people of Terry Fox Elementary School were miraculously on board with this very progressive idea in 1990. Mom says that my Kindergarden class hosted this event in order to expose the sensitivity of the opposite gender so that one could learn to appreciate and sympathize with another person's struggle with one's sex. I'm sure at the time she didn't give a shit about that and was just curious to see what her Brown son would look like in a dress but that's only my assumption. Like with any challenge, I looked at this one with great determination. It was very difficult to put together an appropriate outfit in such a short amount of time. There was no way I could grow out my naps to an appropriately feminine length nor would there be time to order the perfectly sized weave. So I used with what I could scrounge up from my older Sister's closet. There, I found a beautiful green and white checkered dress with a white lace trim, cap sleeves, and a white satin belt that tied around the waist with matching white shoes. It was absolute perfection. It was the only thing in the entire closet that worked with my butterscotch skin tone. It HAD to work! I showed up with great pride that beautiful October morning! I was positively radiant in my checkers. My legs looked absolutely amazing! I remember the feeling of complete liberation which probably had much to do with the wind I felt through my inner thighs. The soundtrack to the Sound of Music was playing at full volume through my mind "Climb every mountain....". I sashayed into my class full of confidence. I was greeted by a slew of fellow cross-dressers who's outfits paled in comparison to my ensemble. Clearly I was the only person in the class who had a full length mirror. I am so appreciative of the fact that I had such a liberal Kindergarden experience. At that point in my life, at 4 years old, I discovered that I had the need to delve further into this arena of pageantry.
My second adventure into womanhood occurred much later in life, in fact, quite recently. It was only this past October here in Dallas when my building, South Side, hosted its annual Halloween party. They held a contest for "best-dressed" with a $250 prize! I was determined to get this money. This was a matter of survival! Yet somehow, only until the very night arrived did I realize that I had not yet figured out an outfit! This was going to be a disaster. I had 2 hours to put something together. At first I tried on a purple unitard with goggles. I was going to say I was going as Esther Williams. After one look in the mirror I realized this wasn't going to go over well. So, in my feeling of defeat, I did what I always do when I need a pick-me-up. I went right to the kitchen and prepared myself a Bacardi and Coke! The alcohol/caffeine combination is deadly and consistently enlightening! After a few swigs of my freshly prepared cocktail with lime garnish I stripped myself naked of the purple unitard and began running around the house in search for ideas. I stopped for a moment in front of one of my MANY full length mirrors to gaze at my naked body when all of a sudden I was distracted. I saw it! Out of the corner of my eye, there it was! Some weeks prior I had purchased a lovely bright red vase covered completely in plumage! Yes, it was a vase decorated entirely in fire-engine red feathers and came with a matching boa! This was the inspiration for my outfit. I didn't know how at the time, but it was going to be the centerpiece of my ensemble! I picked her up and began running around my house looking for clothing options. After what felt like an eternity, I stumbled upon a tiny Black unitard (I have many) with short shorts. This was perfect! It just barely covered underneath my nips and cut just above my thighs with tiny black straps over the top. My mission was clear. I went into the bathroom and shaved all of my French Canadian hair off (there is much to shave off!). I slipped on the unitard and began searching for make-up! I found some beautiful bright red lipstick from Mac that perfectly matched the vase. I applied a generous amount and finished with a top layer of shiny gloss to make sure I could be seen from a mile away! After copious amounts of cocoa butter all over the rest of my skin and the slipping on some shiny black man-pumps, I was out the door wearing nothing but that strip of Black fabric with a red vase in one hand and my 3rd rum and coke in the other! This was going to be fantastic. As I ran down the steps to the Halloween party I was somewhat distraught, disturbed, and perhaps slightly embarrassed at the fact that I was seemingly the only person in costume. Did I get the month wrong? Canadians have their Thanksgiving a month early, is it the reverse for Halloween? I was quite concerned! The people around me seemed completely horrified at my style choice. This is Texas after all. I felt better once I found my friends whom showed up looking equally ridiculous....well almost. Shoniqua was dressed as Alice from Alice in Wonderland and Evangeline (who was wearing the "Diana" hairpiece at the time) was dressed in a sexy burlesque tu-tu situation. We matched! How fantastic! I was still slightly self conscious about my choice of outfit at that point but that all changed once I found the food and beverage station ("beverage" is the operative word here). After several swigs of wine from plastic cups I was feeling quite sensational and it was just in time for the announcement of the winner of the costume contest! I quickly ran up into a huddle of persons who like me had taken time to actually dress up in something. A hostess came out and began passing a microphone down the line. Each person took the microphone and introduced themselves as the character they had dressed up as. Shit! What was I going to call myself? I was wearing nothing but duct tape and a vase! What could I possibly call myself that would actually pass as reasonable? I saw the microphone getting closer and closer to me. I felt the diarrhea stirring. I was so nervous! I couldn't think! Before I knew it, I had the microphone in my hand! Just as I opened my mouth, Jesus came to me! He told me exactly who I was. "Hello everyone! I am Josephine Baker!" (Google it bitches!). The sexy African-American controversial banana wearing vixen had been manifested in my body that night! And I realized it just in time. This was perfect! Surely with my creative outfit and brilliant explanation I was sure to win the money! I stood tall with pride as though there were a small crustacean in my vagina. I was still in anticipation as the microphone was passed back to the hostess who bared a bizarre resemblance to K.D. Lang (Google her after Josephine!). After much deliberation with her associates she returned with an envelope. She slowly opened it up and began to speak. I tried to pass gas in that moment so the smell would be gone by the time I made my acceptance speech. As I trumpeted the new dawn, my spirits were crushed when it was announced that the winner was some Lady Gaga costume wearing bitch from one floor below me! What the Christ was this shit?! I couldn't believe it! Lady Gaga! Really? I was a piece of history for Christ's sake! Black history even! I almost pulled a Faith Hill moment but somehow I kept it together. I kept my dignity and my plastic cup of cheap Merlot in tact. I made my way back up to my room in defeat. I held back the tears for as long as I could in order to stop the mascara from running. I entered my room, sulking. I washed all the make-up off, put the vase and boa back on the self, took a shower, made myself one last adult beverage and collapsed onto my air mattress to wake up the next morning no longer Josephine. As horrific as the experience was, I am grateful to at least know that I have the confidence to pull off the very difficult color combination of red and black in an outfit while showing that much skin, as long as I've had Bacardi....
Ultimately my ventures into the vagina world have been as few and far between as they have been invaluable to my experience as a human being. I've learned so much. It's hard to be a woman! My gosh. I don't know how they do it. I'm so fortunate that I am able to pick and choose when I want my estrogen to be at the top of my priority list. Just imagine being a woman without the hastle of tampons, mood swings, and Spanx! It's the most convenient and magical experience in the world! And I have Dennis Rodman to thank for this awareness. If it weren't for her, I never would've even considered putting on the red feather boa nor the green and white checkered dress. Thanks you talented basketball bitch! I knew since the first time I put on that green dress at 4 years old that my curiosity in the arena of cross-dressing would not easily be satisfied. After a few ventures into this world of the vulva, I have felt enamoured with a newfound joy and enlightenment. The one lesson I have learned most importantly from the experience is....When attending a Halloween party as a transvestite bi-racial Canadian it is best to go as Rosie O'Donnell so you can punch Lady Gaga in the vagina. Watch out for Halloween 2011 BITCH!
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