Most crossdressers/transgenders confront difficulties in going out in public dressed femme for the first time. Of course, another big step is coming out to your coworkers and colleagues about your femme side. I know some people who have had bad experiences with this. Fortunately, I work in publishing, which is a very liberal profession dominated by women and gays (at least in my experience). Before I started freelancing at home as a writer, editor, and artist, I worked as a staff editor for a major educational publisher in the city. Because of my conservative/libertarian politics, many of my colleagues at the time thought I was a bit of a right-wing kook. So when I told them about my feminine, crossdressing side in 2010, I think their opinion of me actually improved, like, "Hey, he's not so bad after all. He's one of us!" Thus, when I came out, it probably benefited my freelance career. That publisher continues to be my main client. But I think they are probably disappointed that my politics remain in the Ron and Rand Paul libertarian camp!
Although I told the folks at that publishing company about my crossdressing, and they expressed support for me over e-mail and telephone conversations, they never met "Jacquelina" until that August 2011 day when I went downtown for a meeting at the company. At the time, I was toying with the notion that I might be transsexual. So I wanted to present the "real me" to my business client. Before I left in the morning, I e-mailed one of the managing editors that I would be coming as Jacquelina. I wanted to warn them ahead of time so they would not be shocked when I showed up in a skirt.
I rode the commuter train for the hour ride into Chicago. Then I walked the 20 to 30 minutes from the station to the central downtown area—an unexpectedly difficult task in my heels, not to mention the uncomfortable summer morning heat. Before I went up to my client, I had my photo taken by the giant, 26-foot-high Marilyn Monroe statue that was in the city at the time. Then I went into a restroom at McDonald's to wipe the sweat off my face, reapply my makeup, and adjust my wig and clothes.
Despite still being a little sweaty and rumpled from the long hot difficult walk, it felt truly wonderful and liberating to walk into that meeting dressed as a woman. Everyone was very nice, friendly, and professional to me, and they all referred to me as Jacquelina. I received a number of compliments on my clothing and jewelry from the women. One woman said she liked my "bling." In between sessions, we went to lunch at a classy place. I had a salad—as any weight-conscious lady would, you know.
After my meetings ended at that client, I took a cab a few blocks north to return some items to another client. In the building's lobby, I ran into a graphic designer whom I knew. When she saw me, she didn't recognize me at first. The look on her face when she finally realized who I was... that was priceless! We hugged and chatted a bit. Then I rode a cab back to the train station to return home.
As I was walking to the train in the station, a black railroad worker (I think he was a mechanic) hit on me. He started walking with me, he asked my name, and he said he hoped to see me again. Wow, you never know where or when you might run into a ->-bleeped-<- admirer!
So my business trip into the big city was an unqualified great experience for me. I had fun, and I got some business done at the same time. I later heard that one of the women at the first client said I inspired her to start dressing better at work! But I also found out that the designer at the second client (a holy roller Catholic lady) was rather disturbed by my ->-bleeped-<- appearance. Oh well, you just can't ever please holy rollers.
Since that first (and only) trip downtown dressed in drag, I've concluded that I'm a crossdresser, not a transsexual. When I went to the same client for meetings a year later, in August 2012, I went dressed as Jack. I'm sure this must have confused some people who thought I was now Jacquelina, but they rolled with the flow, called me Jack, and we again took care of our business together. Frankly, I don't think they care how I dress or what I choose to call myself. As long as I get the work done for them, they'll be happy.
Although I've found that crossdressing/->-bleeped-<- have not hurt my career, I acknowledge that my situation might be somewhat unique in that regard.
