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According to Jason:
If the way I choose to dress or present who I am threatens or affects the way that you or society perceives you then perhpas you need to work on your own self image and worth before you question mine. If I am too painful a reminder of things you have worked hard and possibly been unable to completely stamp out in yourself I will understand if you don't want to enjoy a tasty adult beverage with me.
Since the title of the page is “Skirted Issues” that’s as good as any other place to start!  : I am a man, married to my second wife who does her best to deal with me and all associated issues on a daily basis. (Come on now, you didn’t think skirts or dresses were the only issues in play did you? That is a 7 foot tall server rack in my computer room.)
I discovered my first article of traditional women’s clothing when I was 12 years old. I was looking through a house that had partially burned down for leftover electronics items to tinker with. Instead I found a pair of pink underwear. There was simply something about them that I couldn’t explain then and to this day still can’t.
I also learned in short order that boys do not keep them about or make the mistake of telling their friends about the very idea of putting on an item that girls wear. At least if you don’t want the sideways look and sudden unavailability of your former friend. I further learned after one of my brothers helped my parents “find” my collection and following a very red faced conversation (at least from my side) that it was a road I didn’t want to go down. I was asked to promise never to bring home another pair and with one short lived and guilty exception I kept that promise.
Somewhere between 1985 and 2000 I saw a talk show about lingerie the looked just like women’s but was cut for and made to fit men. It was presented as a giant joke and it was made clear the show hosts and the audience didn’t expect to see it catch on anytime soon. In 1997 I saw another talk show, this time a Jerry Springer episode, “Freaks.” Among the notables were a couple who really, really enjoyed their food and adult activities, often at the same time, a person with extreme piercings and tattoos, another who had gotten surgically implanted artificial whiskers and tattoos to make himself look like a leopard and a man who wore women’s lingerie. I’ll give you three guesses which of these individuals caused the most commotion.
As they mocked this man to no end I came out of the bedroom in a pink nighty and told my wife (before she was my wife) that I was like him. Unfortunately or fortunately depending on how you look at it, she though it was all a big joke. Later when it became more clear it wasn’t a joke she felt hurt and betrayed that it had been kept from her. Had she realized it wasn’t a joke the rest of “us” and the fact that we just celebrated our 15th anniversary would likely have never happened. We have both worked hard to find a compromise we can both live with on it. She is not and likely never will be a fan of it. Fortunately for me she also didn’t feel it fair to demand “her or the skirts” option and does her best to deal with it as she can.
As I tried more and found things I did and didn’t like about it I wanted to research and learn more about it. So far I had the knowledge that I liked women’s clothing, men don’t do that and I was on the wrong path. I started looking on the internet (insert groans here) where I found that some men do like to wear women’s clothing, pretend they are women and further use it as a crutch for “activities” that they couldn’t or wouldn’t accept as “men.” The net happily yielded a very dark underbelly to cross dressing which is the closest label match for me. I turned to the library and read every book I could get my hands on at the time about it. All four of them. I added to that a couple purchased from the bookstore and continued with internet searches more refined from the resources in the books. I learned about umbrella terms like transgendered, (a grab bag of anything out of the accepted gender binary) cross-dresser, (could be anything from liking the underthings to all the way with wig, padding, makeup and forms) transsexual, (born in a gender that doesn’t match their internal gender) and androgynous (on the fence about which gender to present or purposefully choosing neither.)
I eventually found a couple of places on the internet where you could find others who cross dressed to varying degrees and who had more interest in chatting with others than what color your underwear was for a given day or what was underneath it. With these places came a new set of challenges. They could readily accept that I would wear a skirt or dress but seemed very insistent that I also have a feminine name and wear a wig to feel and look my feminine best.
The thought of anything less than all the way was downright abhorrent. How could I dare to harm the cause by going out in public dressing halfway, from the neck down or my favorite colorful term “skag-drag.” Didn’t I realize how much harm I was doing the passable CD’s and TS’s who had risked the loss of jobs, families and possibly their very lives to get where they are and scratch out their places of acceptance in the world? How dare I not view ultimate femininity, passability or just being the best woman I could be as the revered and Holy Grail mark of the “true” (insert preferred label here except my FtM brothers of course!)
Fortunately to offset this smaller but incredibly vocal minority were opinions that ranged from “I wouldn’t be caught dead out looking like you but to each their own,” to “you’re incredibly brave to go out and about your own way” and as far as even the occasional compliment on how I look or an improvement made. I’ve tried to get people not to sling “man in a dress” as such a pejorative insult and also had to un ruffle my own feathers and realize that it’s not always offered that way. I’ve found far more resistance to me being me in the online community than I have in the real one I live in. I’m not naďve enough to think there aren’t giggles, stares or outright laughter at my back but those things were old news long before my first appearance in public in a skirt. Mothers haven’t gathered small children in their skirts in terror at the sight of me and instead have talked to me like any other person at the grocery store. There hasn’t been a breaking news story “Man in rumpled cargo skirt and electric pink pumps buys Girl Scout cookies outside local grocery store.”
I put a lot of thought and soul searching to determine what was up with me. Did I miss the day in how to be a man class where they told us to run screaming from the mere thought of anything traditionally feminine? Did they just forget to ask me when they passed out what was masculine and feminine? How did my wiring get so crossed? I sure seemed to like things and identify with feelings that had been relegated as feminine. Never was worth much at most sports and didn’t have much interest. I would much rather walk or talk my way out of a fight than punch my way out. I wondered if I was supposed to have been a girl instead. I tried a few feminine names but none really seemed to fit the way Jason always has. If I were a girl nobody would question what I wore, patience and empathy would be expected rather than shunned but being a boy by itself never felt wrong to me. Then it occurred to me. The problem never was what gender I am it was the automatic restrictions the infamous “they” would hang on me for it. “They” were at least flexible, I could trade one set of restrictions for the other as long as it was a complete swap.
I can’t give you a dedicated why I am who I am. In truth there are probably as many different reasons as there are people who step so much as one degree off “normal.” I decided to look at the individual pieces and keep the ones that made sense and discard the ones that don’t. Wigs, forms and padding aren’t for me. I’d rather be more selective about what clothing I buy so that it fits me as is. Wearing things long enough to cover the underwear or observing enough decorum while sitting to keep private things private seems like a good idea regardless of gender. Whether it’s boxers or thongs it shouldn’t be common public knowledge what choice you’ve made. Being selective about your surroundings and your company, absolutely. The kind of places where I would likely catch a beating for going in a skirt while obviously male would equally likely earn me a beating if I went there in pants. (Yes Nancy O’Negative you’ve made my page.) I am pretty sure if I chose to hide either in my home or under the disguise of passability (a pretty far stretch for me if I were interested) I would not help the cause any. If nobody realizes there is anything different they haven’t accepted you, they just haven’t noticed. My hope is that while people who encounter me will certainly remember the “man in a dress” they ran into they will also remember he was polite and courteous as well.