Where’s the Line: Crossdressing to Transition

This article reprinted with permission from the author, Reid Vanderburgh, MA.

In 2003, I got a distressed call from Ann (I’ve changed all names), requesting to become a client. Ann was 43, married to Carolyn for 20 years and father to three children, all of them still living at home. They all knew her as Andy. At our first session, Ann started crying as she said, “I’ve never said this aloud to anyone before, but I’ve always felt like a girl inside, from the time I was in nursery school.” For years, Ann had secretly cross-dressed. She worked a job that allowed her to have swing shift hours (3pm to 11pm). Her wife worked a regular 8-5 job. Once the kids were all in school, Ann was free to cross-dress at home during the day, which she did at every opportunity.

Ann called me after she went for a walk in the neighborhood one day, and started crying when she got home. She said to me, “All at once, I felt this huge wave of depression and sadness well up in me, it felt so bad to feel like I had to take Ann off and put on Andy again. That’s when I realized, pretty much out of the blue, that I needed to transition. It wasn’t about the clothes anymore, it was about who I was.”

For many years, Ann had been reasonably content cross-dressing. Now, however, her oldest child was preparing to go away to college. Unbeknownst to her conscious mind, this had put Ann in countdown mode — eventually, all the children would be launched, would she then be able to be true to her real gender identity? She had not let this question emerge into consciousness, until the day she took a walk and came home wishing she was Ann permanently.

So, where is the line between cross-dressing and needing to transition? The relatively new concept of genderqueer provides a framework we can use. Those who adopt the terminology of genderqueer are saying, “The binary gender system doesn’t encompass all of who I am. I need language beyond male and female, and more pronouns than he and she.” One 60-something crossdresser said to me once, “If I was 40 years younger, I’d probably call myself genderqueer.” Regardless of the terminology used for self-definition, these are folks whose gender identity doesn’t conveniently fit the available boxes of U.S. culture: Male or Female. There are varying ways this plays out in folks. Some will say, “Some days I feel more male, some days, more female.” Or, “Some contexts bring out the male in me, some bring out the female.” Others might say, “I feel both male and female all the time.” And others might say, “I don’t want to use the terminology “male” and “female”  at all, because they’re too tied to the gender binary, I want a new word altogether.”

Those who use the term cross-dresser as a self-descriptor might say something like, “There is a part of my personality that just can’t find expression if I’m always in male mode. I can only express that part of me when I’m dressed female.” The implication of this statement is that there is another significant part of their personality that is expressed just fine in male mode.

So, what of Ann, and others in her position? Ann was raised in a fairly conservative, traditional family, in a fairly conservative part of the U.S. She was the oldest child, and the only son. And, she knew herself to be a girl from the time she first interacted with large numbers of her peers, in nursery school. Her socialization and social milieu was such that she learned young there would be a huge price to pay if she didn’t do male right. She tried her best to live up to the expectation of everyone around her, and learned quite well what was expected of her as a man. Not wanting to let others down, she followed the proscripted path toward manhood. She did all she could to shore up her credentials as a man’s man: Joined the military, married her high school sweetheart, got into a male-dominated profession, fathered children.

A crossdresser/genderqueer person in Ann’s position might have tried the same path, to hide the part of themselves that needed expression. But there would also be a large part of their personality that was fine living male, and it’s quite possible the daily cross-dressing would have remained sufficient for a content existence. However, in considering the meaning of her children finally leaving home, Ann allowed a chink in her internal armor, and it wasn’t long before the information flooded through: I’m not a man at all, I’m a woman. Cross-dressing in secret is what kept her alive long enough for the information to surface. She said to me, “If I’d had to be only Andy, I think I would have been too depressed to live.”

The person who needs to transition to female (or male) and live that role full time,  is not in the same position as the person who says, “I’m both genders, or a third gender altogether.” The person who transitions fully might say, “There is no part of me that is okay living male (or female), I need to transition away from that completely in order to find fulfillment.” They would be content in a gender binary system, as long as they transition away from their birth gender assignment.

How to tell the difference? There are some questions each person can ask themselves:

– Is there any time when I’m really content, okay, with my birth gender role/bodily sex? Are there certain contexts in my life where I prefer being my birth gender?

– Is there any time when I really don’t want to be dressed as any other gender than what’s on my birth certificate, where it just doesn’t feel right to cross-dress?

– Do I feel at odds with my birth gender assignment all the time, no matter how I’m dressed or what the situation?

It’s not easy self-examination, as it’s hard to shed a lifetime of socialization within a culture that denigrates any form of genderqueer/cross-dressing/trans identity. It’s hard to ask questions like these without our culture’s judgmentalism getting in the way of the answers. It’s hard to ask these questions without regard to the other people in our lives, we may feel selfish or self-centered for asking such questions without considering our spouse/partner, children, or other family members. But here’s a further question for consideration:

– How deep and intimate can my relationships with anyone be if I’m not my true authentic self with others? Don’t my loved ones deserve to know me as I really am? And why don’t I deserve to be able to be my best authentic self all the time, whoever that person might be?

The older we are when we undertake this kind of self-examination, the more life we have to change, the more overwhelming it can seem to even ask the questions, much less take the answers seriously. But take heart: You don’t have to do this alone. The internet can provide great support initially, allowing you to  find others near you who can support you as you live your way into the answers that work for you. That support can be in the form of a therapist, a support group, mentors who have gone before you — you’ll be able to find something, there are many who have gone before you and are alongside you, asking and answering these same questions just as you are.

5 thoughts on “Where’s the Line: Crossdressing to Transition

  1. Thank you (and Reid) for reposting this article here! While I have a strong aversion to the term “genderqueer” (I prefer polygendered) I do associate with what is what is represented in that term in this piece. Several times a week, while in male mode, I’m often finding myself observing when situations in which I find myself would not fit and/or ring quite true had I been expressing my female gender (let alone wrapping myself in the female clothing I so long to decorate my body). Those realizations also prompt me to admit that there would be many other instances, were I to have fully transitioned to (or be born as) a woman, leaving me somewhere in that gray area “in-between.”

  2. I have been dressing as a girl since 5yr old. Now I’m in my early 50″s still dressing as a girl everyday. I dont own any guy clothes and everything I wear in public is conservative girls clothes.
    I generally blend in with the rest of the women, but have never wanted to transition into a woman. I am content to be a guy underneath and a girl on the outside today forever.

  3. we all probably lead our own ways to where we are going and being a therapist one should ask strong questions that do not lead to vague responses.i am somewhat content with my life style and choices. if i made an announcement that i wanted to become a woman that would change the way many think of me and the way i do business and everything else in life. So being who i am when i am where i am is very important to me. It does require me to lead separate lives that do not cross.

  4. Vague questions are stock in trade for therapists, intended to not be leading questions. If they’re vague, then you have to do even deeper thinking about the ways the questions apply in your own life.

  5. Very interesting read. The 3 questions are good ones to ask one’s self, but they’re still kind of vague. I am male but consider myself transgender because of how deeply I feel femminine. I totally enjoy being a woman and like Ann in the story, we have very similar lifelines. There’s a lot of things in this read that are very true and I didn’t notice anything that wasn’t true either.

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