Recently, I read some comments by a trans, female blogger on adjusting to being the object of the "male gaze," which reminded me of my own discomforting experiences with it during transition, and caused me to reflect on the nature of the gazes that fall upon me since I decided to present a more butch and androgynous appearance.
The arrival of the male gaze is disconcerting when transitioning from male to female. When walking through the world as a man, other men unknowingly grant you the courtesy of generally averting their eyes. Men (well, straight cis men) rarely give each other a once-over as they pass, and even more rarely do they lock eyes.
With women, the once-over is nearly prerequisite. So when a trans woman begins presenting as female, the sudden increased weight of all those stares is palpable. It can trigger a number of feelings and interpretations. It can signal anything from the person having a sexual attraction and not recognizing she's trans at all, to the person reading her as trans and wanting to hurt her for it. It's a bit maddening to never know what feelings and motivations are lurking behind those gazes.
Mostly the unwitting once-over is pretty unremarkable - a man spies a creature with long hair or tits or in a dress, gives her a quick look up and down, (half-thinking) he renders a judgment (e.g. "Not bad," "Nice ass," or "She's busted."), then continues on his way. All this occurs in maybe one second, and is forgotten almost just as quickly. That's the male gaze - a look of entitlement and privilege. As much as it's about unchecked desire, it's about duty. Men are expected to inspect.
When I presented femme I was no stranger to the gaze. Regardless of whether I fulfill the notions of conventional beauty or not, I'm a 6-foot-tall woman with red hair, so people noticed me. They still do, but the way in which they notice me is different when I present butch. The gaze is no longer an inspection; it's a question, investigatory. I can tell because the gaze lasts much longer, and I frequently catch peripheral glimpses of furrowed brows and puzzled, slackened mouths. I feel this returns a modicum of power in the dynamic to me. It feels as if I'm confronting everyone who sees me with the failure of the gender binary. Instead of absent-mindedly looking at my legs or my ass in a lackadaisically sexual manner, the onlooker now becomes conscious of a discord - something's different about that person, they think. They are being challenged to reconcile false notions of gender with the reality that just walked past in a tank top and big, black boots.
It is only a modicum of power, however. I'm far from having the upper hand. The confusion that effects this gaze has an insidious side as well. When many are confronted with the failure of the gender binary, their reaction is just to push harder on the square peg in the round hole. Reactions to trans people rejecting the binary and to those trying to pass on either end of the spectrum provide a fascinating paradox. It's a catch-22 - presenting as one side of the binary, people focus on the few things about the trans person that don't fit (an MTF with a masculine-sounding voice, for instance) in order to kick them out of their chosen gender. On the other hand, if they choose ambiguous/androgynous presentation, the uncertainty will cause onlookers to latch on to the few things that do fit (Are there tits? Any signs of facial hair?) to forcibly assign them a gender.
This happened to me in a gay bar a few weeks ago. Trying my best to flag down a bartender, I noticed the stolen glances of a gay male couple to my left. Postures inclined slightly and their voices dropped to whisper level. Some additional quick, over-the-shoulder looks confirmed that I was the subject of their sub-rosa communique. Not wanting anything other than my beer and to return to my friends, I decided not to address them or tip off that I noticed them noticing me. They had a quick back-and-forth until one of them slyly motioned to his chest while mouthing a few silent words to his partner to call attention to my breasts.
Then they both nodded. My gender had been decided. Despite my purposefully chosen androgynous presentation, despite having zero direct interaction with me, two gay men who (presumably) feel no physical attraction for women and who (presumably) are allies of the trans population concluded that my place was the F pole of the gender binary.
It's almost as if I pass as female better now that I'm rejecting conventional femininity. Everyone is too uncomfortable with ambiguous gender, so when they see a bit of mascara  or traces of my breasts they quickly assure themselves, "OK, she's female," and once again all is right with the world.
When you try to be one of them, they kick you out. When you refuse to be one of them, they make you into one of them. This hypocrisy illuminates the fact that there are no principles behind such discriminatory practices. It is blind ignorance, fear, and hate - the unknowing violence and antipathy toward transgender people that our culture and society implicitly instills in people.
Whatever the trans person's desire, it's wrong. Want to be a "real man" or a "real woman?" Too bad. A reason will be found to disqualify you: Your body is different. You don't look right. You weren't always the gender you say you are. Don't want to be a "real man" or "real woman?" Tough shit.
An argument will be made to make you one: You still look like a girl to me so you're a girl. You say you're a man but your body's genitals dictate what you are. Surgery gave you the genitals of the gender you claim? Well, you were born with something different and surgically constructed genitals aren't natural. You don't produce sperm, so you're a woman. You don't have a uterus, so you're a man . . . . The basis of the argument is incidental to undermining the trans person's claimed identity, whatever it may be. The only purpose of these cultural machinations is to marginalize and isolate the trans person, to disenfranchise that which is different or takes more than a few seconds to understand.
The scary thing is that those who harbor these sentiments and motivations rarely express them so explicitly, or even realize they're there. Trans people do occasionally hear comments like the above directed at them in conversation, but much more often they occur as onlookers' automatic thoughts that are never vocalized, or if they are, whispered discreetly in a companion's ear. Like the story related above, this happens even among our allies. They don't even know they're doing it.
An androgynous person's appearance always triggers the question: "Boy or girl?" be it posed to someone else or solely internal. If a conclusion cannot be reached, further investigation always occurs. "It's a guy, his shoulders are too broad." "No, it's a girl, look at her chest. It looks like she has breast tissue." These inner monologues and whispered dialogues are running all the time in our presence. We might not hear or notice, but we know it's happening. We know our bodies and mannerisms are being examined, mentally poked and prodded, stuffed into boxes, stripped of and stamped with labels . . . and much more rarely than we'd like to believe, do we have a say in the matter.
 Personally, my solution to this was to keep telling myself, "They're not reading you, you're just passing as a woman now, and this is what women have to deal with."
 And perhaps sex and sexuality as well, if they find me attractive. I always say the look I'm going for when I present butch is to make people think, "I don't know if that's a boy or a girl, but I want to fuck them."
 Being an A cup, my butch look involves a light sports bra with moderate binding action. Unless you're looking for them, my breasts often go unnoticed in this look.
 My butch side still loves eye makeup.