Transitioning to A Better Self...16 Years Later

Recently, I decided to make a major announcement in my life. I announced on my fb page that after 16 years of countless photos, YouTube videos and many memories along the way, I decided I wasn't going to wait any longer and finally begin to live as Kayleah on a full-time basis. Over these years I have actually lost count on how many pictures of me that were taken, but it was well over 400. Then I started doing the YouTube videos (around 30 at last count), which are still up and running to this day. Most of these pics I also put on my flikr page as well, even those taken off my webcam. OK, from the day I first saw myself dolled up in 1998 to the present, I never said I looked anything like one of those ultra-skinny supermodels that walk the fashion runways in Paris or Milan. Then again, neither do my fellow T-girls of color. We look just how we look, only a little bit happier. This was a pinnacle chain of events that happened to me. It's as if God was wondering, "What took you so long"?

1998 was somewhat of a breakthrough year of sorts. I got to attend a few meetings of the Gemini Gender Group, a gathering of cross-dressing/transgendered individuals, which met at a church on in suburban Milwaukee. Yes, I shall admit that the CD's were all originally Caucasian men and myself. They still welcomed me with open arms. So what they never attempted to find their feminine voice? They could look very feminine and still use their everyday voice. It was quite comfortable, telling one another about our attire, makeup, hair styles, etc. There was this one person, whose name has escaped my memory, that I got close to. She was a full-time transgender, who became a close ally. Maybe a bit too close. After a GGG meeting one night we went to a LGBT-friendly bar and stayed until near bar time. She got to give me a lift home to (sadly) my dad's house, gave me a hug, then we kissed for about 10 seconds until I noticed someone driving by my house from a nearby bar, believing he was seeing two lesbians making out. I quickly ceased this warm moment, pointing to the uninvited company. We stayed close friends until I moved here to Illinois.  One of those meetings is where I first met Mariah (you know the rest of the story from there). We got to show off hair get-ups from Rachel's Hair & Wig Salon in Chicago. I got to talking to one person, who did like how I did my makeup for that night. It was there that I mentioned that I wanted to maybe live like this. Yet like them, life usually gets in the way. 

That spring was also the first time that I went out to a bar dolled up, too. There was this now-closed bar one Milwaukee's South Side right by 1-94 near the LGBT district called Just Us. This was a nice place to hang out. I had myself a brew and just watched the scenery of life go by. I didn't have a great wardrobe for me to have so I went to the usual place to get some threads-Goodwill!! The outfit I wore that night was something your grandma would wear for sure, but it did the trick. I even wore gloves! Lo and behold when I arrived, they had a little drag show that night, too. Not professional impersonators, mind you. Just some folks who wanted to have some fun on a Saturday night. I got to eventually do a number myself there, too. My drag performing debut wearing this borrowed purple gown that I barely got zipped up, doing "Give Me One Reason" by Tracy Chapman. Made a few friends that night, using our feminine names, of course. I did make a few more appearances there, including the bar's final night, where we said goodbye to Just Us. I can say I should have thought up something better to wear that night.

In Milwaukee, we have an attraction called Discovery World Museum, a place where people can learn about how math and science in daily routines. I got to work there during part of the summer doing some cowboy or sorts, explaining about leverage to the kids. There was a co-worker there who I may have guessed I was different. She was actually bi-sexual, and she showed me the ropes of the LGBT scene in town, especially where bars like Just Us and LaCage were located. I wish I kept in touch with her! She did a few things for me, including help me get dolled up one night as an escort, and seeing me do my Just Us drag bit-two weeks after getting fired because some girl scout ( of all people) saw me with glitter in my face. Girl Scout told the higher-ups, and I got the pink-slip. This is a true story!!! I tried to use that only for my hair, but that shit was hard as hell to get off!! I didn't know how to wash it off. Ironically enough, I got that hair glitter (as well as my first good bra) at Frederick's of Hollywood, where cross-dressers have quite a following...or so I was told!

Having this experience did come with a cost. During this time of year I was singing in church with a Pentacostal church. This where women basically only wear dresses/skirts, no pants for religious reasons. I had make the mistake of trying to surprise one of my choir mates by dressing up as a girl to startle her. Let the floodgates arise! Like the popular phrase, "Loose lips sink ships", she told the choir and the church about this encounter. I was confronted eventually by the choir director just before service one Sunday. I told her that I cross-dressed and I didn't see the problem. She basically told me that God made me a man, yadda, yadda, yadda, and barred me from singing with the choir that day. Spent that whole service in the bathroom, chillin'. That next practice on that following Wednesday she asked the entire choir to pray for me to get rid of this kind of sin. Whatever.  I saved them the time and trouble by leaving the choir and the church. Besides, my family is mainly Missionary Baptist, anyway!

I got to experience being a part of Milwaukee Pride Fest, the country's largest volunteer-run LGBT festival! Volunteered all three days of that weekend. It was quite nice on our lakefront that weekend. I did security the first day. I had this matching jump suit with pink, turquoise and white on it. Good thing it matched the pink SECURITY cap! The next two nights, however, I wanted to express myself in front of the Pride Fest crowd. What did I do? Of course-I dressed up. However, since my dad knew nothing about this, I had to dress up, makeup and all, in the men's bathroom at the Summerfest Grounds where the festival took place. As one would expect, I did see someone eyeing me as I applied my makeup in the mirror. All I was hoping was this shit head mind his matter and let me finish my face! Nothing happened. I got to do some vending that night in front of the Miller Oasis stage, selling Pride Fest items and LGBT flags. The entertainment wasn't to bad, either. Two bands played while vending, including a female duo (one played keyboards, the other drums) and a male leather a capella quartet. I do believe one gay guy wanted to see if my boobs I had on were real, so I let him feel me up. Day Three I was at the information booth near the front gates and those unruly anti-gay protesters. This time I painted myself in the car in the parking lot. Not comfy, but still I was expressing myself. That is where I met my eventual drag mom Janice. She got to paint my face a few times, looking quite dark compared to the way I do my makeup now. I got to hang with her for a while, not knowing she was a petty thief. 

Janice also helped me enter my first ( and only) drag pageant. This happened Thanksgiving weekend of 1998. Sunday night. Where I normally stay home. I got to have acryilic nails topped with imitation jewels. I got to spray paint orange some pumps that actually did fit me one time or another. The gown was borrowed from Janice (a transgender who already had the surgery), standing about a full foot taller. She even had a bathing suit for me to wear, plus padding to give me some natural curves. Nobody needed to see my legs! Thank God for (two pairs of) pantyhose! I performed Jennifer Holiday's I'm On Your Side. Sometimes I wonder what it is with heavy-set women singing their butts off? Someone enjoyed my performance so well that when she commented, I thought she was insulting me! Don't get me wrong, I knew I didn't want to be a performer. I did this for fun. I wanted people to see me as myself, not the entertainer. This was also videotaped, too. I had my own copy of this thing, which I was too embarrassed to even watch at her house. I did view it, back at home, to see what I did right and what could use some improvements. I got to trade that video for Janice's burlap-sack like one-piece slipover dress. I still have it to this very day. Janice reportedly lost the tape. Oh well. Time to make more memories!