Forced to avoid shaving my face due to an impending trip to Electrolysis 3000 in Dallas, I am quite a sight. I don’t look much like my old self or my new self, but something hybrid, resisting category. I avoided going to town all weekend and instead got a lot of chores done, but the time came to go get groceries.

I briefly considered wearing a skirt, tight blouse, and makeup, and thought better of it. I wasn’t interested in causing a scene, and I knew that no amount of makeup would disguise the fact that I’ve got 2 days’ growth on my face, diminished though it might be through laser treatments. No, I put in trousers and a work shirt, paying homage to Joyce with diamond earrings. I combed my long hair back and put on a straw hat and then headed out into the world.

At the store, I must say I felt very, very odd — I’ve been Joyce for quite a while, and I felt (and you’ll no doubt recognize the hilarious irony here) like I was in drag, or drab, to be more precise. [If drag is shorthand for “Dressed as a Girl,” then the opposite is drab, or “Dressed as a Boy.”] I still had my backpack purse and my mannerisms and I certainly felt completely Joycean, but I also was aware of being tentative and feeling like hiding, and it reminded me of years ago when I first went out in drag: afraid, tentative, feeling as if I didn’t fit into society at all.

I did my shopping as I always do and talked to the butcher as I bought 4 nice ribeye steaks to cook tonight and I had almost forgotten about the disconnect between my appearance and my essence, when an interesting thing happened in the checkout aisle. I was thumbing through O[prah] magazine while a young woman scanned my items, and the bag boy, a youth of perhaps 16, asked, “Do you like Oprah?”

“Well, I don’t know. I suppose so. Why do you ask?”

“I used to like her,” he said, “but she said some things about religion that really turned me off.”

I told him of hearing a news story on NPR this past weekend about a woman in Chicago who is living the entire year of 2008 adhering to every single bit of advice Oprah gives, whether it be from O magazine, her show, or the internet. This woman was having quite a bit of trouble with it, but found it an interesting exercise.

His eyes got big. “Really? That sounds fascinating.”

“Well, it’s like doing anything to its extreme, isn’t it? That sort of thing reveals a lot about the system you’re adhering to, or studying, if you think of it.”

We started walking out to the car, still engaged in conversation, talking about avoiding the extremes of life, like whether this past weekend’s productivity was better than a couple of days on the hammock.

He shook his head. “I’m going to have a hard time balancing it all it this fall — I’m in a university track at my school, which means I go to school three days a week, but have homework the rest of the week. I have to balance that schedule with my work here at the supermarket, and with my dual-credit courses.”

I told him this 3-day-a-week curriculum must operate under the assumption that the student is self motivated since it can’t use absences or tardies to control students, and he agreed entirely. “I’m very motivated!”

The groceries loaded, he looked warmly at me and said, “Thanks for talking. See you around.”

“Yeah. Good luck balancing all that stuff on your plate.”

As I sat in my car and reflected on my outing, it hit me (although I’m sure it hit you, dear reader, a lot faster than it got through my dense skull) that the reason this bag boy and I were getting along so great is that he was a young gay man and my androgyny and chattiness was taken as a sign that I was a gay man and we were flirting. I didn’t mind it, not being homophobic, but I found myself chuckling at the layers of irony, that I appear to be a scruffy gay man instead of a transsexual woman, that I can’t “butch up” any more, even with a beard, that I am gay in the sense of being in a same-sex relationship with my wife so that that bag-boy got something right, but just not the flavor of my same sex existence.

It was interesting and even somewhat pleasant, and I have one more day of drab adventures before getting to return to my normal self, and that will be quite a relief.

This is a follow-up post to my previous post on the nature of authenticity and legitimacy in any sort of transition.

I’m well aware of the tension and fear about not being a legitimate woman when my transition is complete — I think it’s often a constant fear for transsexuals, sometimes one that plagues them and other times something that’s they’re mildly aware of. I’m feeling quite authentic, but I’m anxious about being legitimate.

But what about sexual orientation? Mary Jo and I have discussed the fact that assuming I’m taken to be a woman, then we will be taken to be a lesbian couple. We talk about it from time to time and brainstorm how that social perception is going to affect both of us, but it has not sunk in for me that this identification involves belonging to a category called “same sex couple.” Having just come out to a lesbian couple who are longtime dear friends, though, I felt this morning a sudden pang of illegitimacy.

Not only do I feel illegitimate as a woman, never having been a girl or had a period or worried about being pregnant, but I also feel completely illegitimate as a lesbian. Just as I’ve enjoyed the male privilege all my life, Mary Jo and I have enjoyed the heterosexual privilege all our lives.

What rights do we have to identify as lesbians? How do you get to be lesbians? Is it a simple matter of private practice, or these days is there an expectation of a larger social identity? Helen Boyd often remarks on that crossdressers would be a lot more sympathatic if they actually took the time to learn about women instead of imitating them, and I feel something similar about same-sex relationships.

As I look ahead to deeper and fuller transition (we’re only 10 weeks from May 24th, when everyone knows), I find myself anticipating challenges to legitimacy from various directions. I expect to be taken aside and be put in my place by women (you’re not a legitimate woman), men (everything we did together in the guise of a masculine bond was illegitimate), and lesbians (you’re just a straight couple who got thrown an interesting curveball, but you’re not legitimate lesbians).

I don’t know what to to with these feelings except to acknowledge their legitimacy and to engage my friends and colleagues authentically and humbly. I may not have been a woman, or a lesbian, or an activist, or a queer-studies theorist, or any number of categories into which I may transition, but I have an authentic desire to learn.