I've never been a manly man. I'm not into sports, I'm not good with my hands, and even though I've tried to work my body into something resembling good physical condition, I feel like a different species than some of the men you see, the ones out on a nice day jogging or playing soccer. Compared to them, I am a small, unimpressive thing with smoother, softer skin and a more rounded body. I lead with my hips when I dance. I can grow the facial hair of a 14-year-old boy if I don't shave for a month. The last time I counted—two months ago—I had exactly 37 chest hairs.

I'm a heterosexual man with a normal-to-high sex drive and a girlfriend of three years, but men and masculine attitudes have always bored me. When I was 6 or 7, while my cousins and uncles would congregate in the living room to shout at football players on television, I would stay in the kitchen and talk with the women and help them clean up. I was always fascinated with the gossip and the nuanced interpretations of everyday events that the women in my family shared. They were so wise that I had no desire to be anywhere else. Listening to them talk through their lives was like getting a road map to what was ahead of me, a way to learn how to be in the world. It was something that the men in my life wouldn't—or couldn't—teach me.

Middle-aged women are more than tolerant of a young boy, of course, but when the boy hits puberty, things in the kitchen get a little weirder. An unspoken discomfort with having a teenage boy in their space eventually pushed me away. I'd stand in the living room for a while, watching the men watch football. Though my exasperated father tried again and again to explain the rules to me, I never developed any interest at all—I still, to this day, don't understand how the game is played. Separated from the women in the kitchen by gender and separated from the men in the living room by interests, I would go up to my room and read.

In high school, people mocked me relentlessly for my weight, my glasses, and my nerdly pursuits—but most of the jokes revolved around punishing me for my unmasculine behaviors. I didn't walk in that careless way that jocks do. I was about as aggressive as an overfed hamster, and for that I was called all the names that men who don't act manly are called. One day after school, I was thrown down a flight of stairs by a guy who hated me because I couldn't stand up to him. I was bounced off lockers after gym class by guys with muscles and facial hair because I tried to hide my pink, hairless body in a corner when I changed.

The only male friends I had tended to be gay or barely functioning science-fiction geeks who made me look positively cosmopolitan in comparison. Most of my friends were women. If real men wanted nothing to do with me, I certainly wouldn't have anything to do with them. Eventually, I intentionally fucked with my nonmasculine tendencies by toying with the feminine. I'd have mud-mask parties, for instance, or three female roommates and I would dye our hair. These attempts to try on feminine affectations generally ended in failure; whatever else I was, I certainly wasn't pretty. Nail polish and steaming water facials felt in many ways as ridiculous as sports.

I wasn't a girly man, I was just more of a non-man. A woman at a party once insisted that I was gay because during a game involving a hammer she said that I had "the swishiest swing" she'd ever seen in her life, including among women. It was a white-trash-themed party, and all the men had fake mullets and belched and swore and played recklessly with power tools. Though I'm from a family of carpenters and car mechanics, I've never really handled any power tools—I find it impossible to be in the same room with them without picturing all the different ways I could accidentally dismember and mutilate myself. Hair stylists always comment on my inability to grow sideburns. "You're the most hairless guy I've ever seen," a stylist at Rudy's once told me when she picked up a razor to trim the back of my neck and discovered that there was no need.

Dudes—the kind of men you see at bars on Saturday night with porcupiney hair and striped, button-up shirts with stiff collars open down to there with a white wife-beater T-shirt peeking out from underneath—are as alien to me as the Amish, or people with Asperger's syndrome, or television newscasters. And here's the thing: If you want to try to understand masculinity, asking men isn't the way to go about it. When I was 13, I asked a neighbor why he liked motorcycles. "I just do, okay?" he said. I asked him to further explain what it was, precisely, about motorcycles that he liked. "Nothin'," he said. "I just think they're cool." I asked him a couple more times, in a couple different ways, and finally he just shouted "Faggot!" and hit me and ran away.

Neither are women good to ask, if only because they are better at talking about what masculinity isn't. On subjects like manliness, they're often as tongue-tied as men. Hetero women I've known who are enthralled with male bodybuilders, for instance, can usually only go so far as explain that they like them because they're—and here would be a big, unconscious sigh—"so big," and their glassy stares would indicate that they weren't going to be able to explain any further.

Which is why, after many years of thinking about it, I decided to visit Dr. Peter Shalit, a medical doctor who has worked with transsexuals in his private practice since 1990. He was the first person I've ever talked to about my masculine deficiency without cautiously framing it as a self-deprecating joke. We met in a cramped First Hill examining room decorated with yellowing Far Side cartoons. Dr. Shalit is smallish and balding and gives the impression of a young boy dressing up as a doctor. He listened with a real acuteness, choosing words with patience and certainty. "The biggest part of masculinity, physically, is the hormones," he said, beginning with the most obvious signifier of manhood. "Testosterone will make you hairier."

Does that mean it would be possible for me to grow facial hair with a testosterone treatment? "It depends," he said. "FTMs"—female-to-male transsexuals—"get hairy based on their genetic background. People from Mexican or Asian backgrounds aren't as likely to get hairy, but if you ask them, they'll say that men in their family can't grow a beard, either." Facial hair is genetic, but it varies from person to person, and patients simply don't know how they'll turn out until the treatment begins.

One common assumption is that, somehow, as soon as a male's body develops testosterone, he becomes a jackass. That's because, after puberty, a great many men become jackasses. Once, when facing financial ruin, I tried to work as a landscaper. In my first weeks there, Pete, the owner of the landscaping company, turned to me out of the blue and said: "So, Paul, what do you think about titties?" He was driving us in the company truck and we were heading out to plant sod in front of a brand-new house that resembled a wedding cake. I was speechless for a moment; then, ingeniously, instead of answering, I asked him what he thought about titties. He went on to list a dozen manly uses for breasts in the most colorful language imaginable, concluding with the ever-popular, "You can just shove your face right in there between 'em and go, you know," which he said while waving his face violently from side to side like a dog shaking off water. He let his mouth hang slack and issued a roar of pleasure, yodeling in a canyon of gigantic, imaginary cleavage. After that sloppy display, there was an awkward pause, and I demurely told him that I was more of a leg man.

Another fellow landscaper, Ron—a wiry little man who had a small tattoo of a swastika on his hand, whose license had been revoked for drunken driving, and who was on parole for beating his wife in public—was an utter animal when it came to women. Occasionally, we'd drive past a middle school and Ron, admiring a girl far too young for him, would mutter, "I'll come back and see you in five years, honey." As we'd rake out the shrubs of wealthy homeowners, he'd hoot, "Hey, baby, you got a license for that ass?" and "I'll take you home and show you a good time!" and so on. The women he was hooting at would keep walking, or very occasionally flip Ron off, and he'd laugh and tell them that they knew where to go if they wanted to get fucked. One day, I started shouting at him. Why did he persist in this repulsive behavior when the women clearly didn't want him to, when it was wrong and unwelcome? He smiled and replied, "Most of the time it doesn't work, but one out of a hundred times it does work."

Testosterone isn't an excuse for dogged, brainless horniness, and neither is it an excuse for aggression. Those steroid-addled men who work their bodies into patties of muscle for sport are freaks of science, not exemplars of manhood. "There is this thing called 'roid rage," Dr. Shalit said. "But those are really extreme steroids." In the name of science, men have been given four times the normal amount of testosterone and there's almost no discernable effect. "The steroid rage may come from the fact that they're doing high doses. In a way it's like PMS, because they're having big fluxes in their bodies." Testosterone is, in fact, better at creating feelings of amorousness than inciting violence. "When they discovered testosterone a little less than a hundred years ago, they gave it to gay men to see if it would make them less gay, but it just actually made them into hornier gay men."

Testosterone might have a lot to do with the physical characteristics of being a man, but Dr. Shalit doesn't think it has much to do with masculinity itself. "Most of the FTM individuals that I've dealt with have this sort of guyness, this sort of masculinity that's not exaggerated. They're just guys who don't have a body to match their psyche."

When pressed to rate factors in terms of masculinity, he offered a rough list: "I'd say it's the psyche first, hormones next, and the physical body is the least important."

The body is relatively unimportant in how many FTMs view themselves. When I made a clumsy reference to transmen "changing their equipment," Dr. Shalit corrected me: Most FTMs don't actually acquire penises anymore. Genital surgery is expensive and the results are not always satisfying. "We used to be skeptical of transgender folks who say, 'I don't want to have genital surgery,' but more and more I'm accepting of them," Dr. Shalit said. "Many of them will do what we call 'an upper,' which is a mastectomy, and then there's a minor surgery where they can trim a ligament to release the clitoris so it resembles a preadolescent penis. I think as long as they're happy with their bodies, that's cool."

Dr. Howard Leonard, PhD, is a psychotherapist who has been seeing transgender people since the "very late 1970s." Trans patients make up 15 to 20 percent of his client base. Sitting in his roomy, darkened office on a comfy couch, I had to fight the unmasculine urge to spill my life story. He's a gentle man with quiet mannerisms, but he's forceful to correct a mistake or address an attitude in society that he finds unjust.

Within Seattle's progressive culture, at least, he thinks that the idea of what masculinity is is changing. "Even as recent as 10 years ago, people were trying to stick themselves in a box," he says. They thought "that being a guy means I'm supposed to do these things, dress a certain way, walk a certain way, be aggressive, be gruff, be like the Marlboro Man." He paused. "Society relates to a person, they don't relate to a pair of genitals, but being a man sounds like it's objective. It's not, but it sounds like it: 'If I have a penis, I'm a man.' Masculinity is a state of being, a set of traits or characteristics. It used to be more like, 'I must be a guy because I'm interested in these things.' Now I think it's way more: 'Here's the type of guy I want to be.'"

There's so much more to gender than my relatively banal experiences, of course. Gender is fascinating. For example, FTMs and MTFs (male-to-female transsexuals) experience a very interesting trade-off, according to Dr. Leonard: "It's way harder to feminize than to masculinize. A meek guy doesn't stand out as much as an aggressive woman." Some men are frustrated when they find out that they have a smaller range of accepted behaviors to choose from when they become external females. "It's totally counterintuitive. Men have to fit into a narrower range of options, but in the trans world, it's the opposite. It's easier to act/behave/walk/present as a guy than it is for someone who was raised male to tone down enough and slow down and present in a way that seems female."

Which means that a lot of becoming a man has to do with being treated like one. Dr. Leonard talked about the transcendent sense of relief when someone is finally accepted for the gender that they feel like inside, although it's entirely possible for FTMs to get frustrated in different ways when they become men, too. "We're raised differently as men and women. There's a male entitlement that goes unnoticed by men because it's just their normal life and it is noticed by women because it's not their normal life."

I thought of a female friend of mine who once complained that sharing a room with a man took effort. "It's as though," she said, "his being there, his existence, demanded some of my attention." Talk to most men about male entitlement and they'll look at you like you're crazy. But it's real and it's more than just being able to walk around the city after dark without the fear of being raped. It's the way strangers look at you on the street, or the way they relate to you on the phone, or the way their bodies in space interact with your personal space. Think of the inconsiderate seven-foot-tall oaf who sometimes winds up in front of you at a concert and then imagine that man appearing everywhere in your life, stepping on your toes and stumbling back into you and all the while not so much as acknowledging your existence. Many MTFs experience these losses of privilege—the abstract privilege that's concomitant with masculinity—as a series of surprising, disheartening blows. Their gender transformation is going to take a bit longer than they thought, it turns out.

Dr. Leonard describes what FTMs deal with as a simultaneous attraction and repulsion: "If you have someone who's raised in a female body and they suddenly get that male entitlement, there's a sense of both I want to use this because I've got it and also My feminism says that I abhor the fact that I want to use this. I like this but I don't like that I like this."

Aidan Key is a short man with broad shoulders and a firm handshake. He has muscular arms and a confident stance; he occasionally strokes his goatee thoughtfully, just the way people do on television. He was born a woman, with an identical twin sister who happily remains a woman to this day. His voice is a bit nasal, but it's nothing that would cause anyone to think twice; I know many natural-born men who have higher voices. If we were to quiz people at the coffee shop where we held our interview, pretty much everyone—myself included—would pick him as the more masculine of the two of us.

It's weird, waiting in a coffee shop for someone you've never met who you know is transgender. Is that bodybuilder a seriously overcompensating FTM? That reedy boy with the long hair is sort of feminine—is he who I'm looking for? I gave up guessing and called Key's cell. Just then, his phone rang. He was standing right in front of me, a guy I hadn't even considered. Key, who runs Gender Odyssey, a Seattle-based transgender conference now in its sixth year, sometimes speaks at schools on the subject of transsexualism, and he often begins by having the class make assumptions about him without telling them the subject he's there to discuss: What's my class status? What's my education level? What kind of hobbies do I have? Pets? "The answers are all over the map. You should try it sometime," he says.

Key shares a prevailing opinion among transsexuals: Masculinity is something you're born with. "Growing up, I had a natural level of masculinity, certainly in contrast to my sister, who showed more stereotypically feminine girlish behavior and all that. I was more of a tomboy." Key didn't have any close male role models, and even in high school when he found some male friends, "They viewed me more as dating material."

Later, Key started identifying as a lesbian. He found a subculture that seemed to accept him. "I got connected with these [women] 15 to 20 years older than me. The masculinity they saw in me was something to be celebrated, something that was desirable. That was a pretty good time for me."

With acceptance came the desire to take the next step, but when he told his new friends that he wanted to become a man, everyone became less accommodating: "In the lesbian community, we could express masculinity as much as we wanted, even to the point of growing facial hair, wearing men's clothing, wearing a strap-on, or binding breasts. You could do all of that, but you had to do it in the context of the word woman." This is because, the thinking goes, white heterosexual men "keep you down as you're fighting to empower yourself. Our society sets us up as an enemy to overcome, and it happens to be embodied in that particular person I'm transitioning to."

Key looked into his Americano for a moment and I fiddled with the filter in my pot of tea. "When I was transitioning, I was working as a body piercer. It was at a point when people would use male or female pronouns when they talked to me. People would come in for a piercing and I would be trying to assess who they're seeing and respond accordingly. If a person would come in with a couple of friends, and two of them would be using male pronouns and the other would use the female, all of a sudden I couldn't even talk anymore. Everyone who walks in to be pierced is a little bit nervous or a lot nervous. My job, besides poking a hole in them, which is not rocket science, is to help them navigate that experience, to soothe them and to help them get through this as quickly and painlessly as possible. I thought I was going out of my mind. I did 10 to 15 piercings a day, so finally I was like, Forget it. I'm just going to be and I don't care. The minute I did that was when I started getting consistently read as male. One of the lessons I learned is that my natural masculinity is there. People see it and if I relax and be myself, that will serve me best in the long run."

Everyone makes snap judgments about sexuality hundreds of time every day, and gender is one of the first things that we unconsciously decide about a person. Many men with long hair have been mistakenly hit on by drunken homeless guys or confused for young women by old folks with myopia and a nosy demeanor. People get unsettled, even nervous, if the initial gender assigning doesn't go well on meeting someone new—it's one of the reasons why transsexuals can unnerve so many otherwise progressive/sophisticated/open-minded people.

"I have a more masculine presentation than a number of transmen. I have some muscles, and I have either a goatee or a full beard so I can move down the street and not have to interact with anyone, whereas before, every person I would pass I would question who he or she was."

Another element of masculine privilege is developing with age. "I'm 44 years old and no one's looking at me like I'm used up or past my prime. My sister is the same age and she's struggling with that. Society is shifting their perceptions of her because they see her as a 44-year-old woman. Privilege is something that most white transmen struggle with."

The Royal Knights, a drag-king troupe, perform every Saturday night at a bar called On the Rocks on Tacoma's waterfront. It's less a bar and more a compound, with four or five large rooms spread over two floors. The Knights' manager takes me on a tour of On the Rocks as the Knights put on their beards and costumes. They only want to talk to me while in drag.

Charlie Menace is physically imposing, but he has a laid-back demeanor, kind of a big teddy-bear-ness. He says, "I'd never even heard of drag kings before and I ran into an old buddy of mine who explained it to me, and so I worked out a piece and went and auditioned." Charlie mostly identifies as a man all the time now, and he credits his drag experiences with helping him come to terms with who he is. Derek Ryder is a hyper-outgoing African American who asked not to be photographed for fear of repercussions at his job, where he is a she whose most sophisticated coworkers assume is a lesbian. He's a fireball onstage, though. "It's a rush. It's a hook," he says.

Damien seems like an average working-class guy, talking a lot about his wife and kids and work. "I started because my wife saw their website and said, 'You should totally do this. You want to be a boy, anyway.' That's your choice. A hundred thousand dollars for a penis or a hundred thousand dollars for a house? This is definitely as close as I'm going to get to being a boy."

Two of the Knights identify as male, and most of the others pass as male from time to time outside the bar. Derek says, "I can pass without the drag. I've been called 'sir.' I've gone into women's bathrooms and women threaten to hit me with their purses. One time, this lady screamed for me to get out of the bathroom because I'm a guy. I showed her my ID and she swore that I'm not the person that my ID says I am. Finally I said, look"—Derek gestures at his chest—"do you want me to whip 'em out?"

The kings have different ideas on matters of privilege than Dr. Leonard or Aidan Key. "All my guy friends treat my girl friends like crap," Charlie says. "Some drag kings treat their women totally like a guy would do it. Women will complain that they don't like the way that men treat them, but then when they become a man they do it, too."

Derek volunteers, "Everybody loves control. When you get power, you get crazy. When you're playing a masculine role in a lesbian relationship and you're doing that power play, you get into it. I get the power; I get to tell you to get my beer, get me dinner. If the person you're with allows you to act that way, it's gonna be that way."

The Royal Knights start to put me in man drag. The costume is important. I'd been thinking about what kind of masculine man I would be, and the first thing that came to mind was the kind of man I hated most from my childhood in Maine: the white drug dealer who still lives in his mom's basement, plays around with weights a little bit, and totally immerses himself in hiphop culture because he sees himself as "street" and "edgy," although he'd probably cross the street muttering racial epithets under his breath if he ever saw a real African American—a true rarity in rural Maine—walking in his direction.

With the sartorial advice of my friend Kelly, who is along to photograph the transformation, I'd bought an outfit at Value Village for about 20 bucks: super-baggy Tommy jeans, a mesh Michigan tank top, and a yellow velour FUBU short-sleeve, button-up shirt. The clothes feel comfortable but awkward—my arms are so white and flabby that I don't usually let them out into the open air.

The Knights' narrow dressing room is a kind of loosely organized medley of masculine showbiz accoutrement: One wall has a long mirror lined with hair gel and eyeliner and duct tape, the other is a messy line of clothes on hangers—sports equipment, huge cowboy hats, whitewashed denim, some nicely cut black suits. The Knights go thrift shopping three weeks out of every month; they bring outfits in and out of rotation.

Charlie gives me my first—and probably the only I'll ever have—beard and mustache. He uses his own hair trimmings from his most recent buzz. He draws a thin line of glue on my face, then fastidiously applies the hair to the line. I wind up with a skinny Backstreet Boys beard, the kind that requires a tiny razor to maintain. It squares my face a little bit, detracting from my puffy lips. Looking in the mirror is a shock, but kind of an exciting one. My hair, normally too listless and heavy to take any product, stands on end with layers of gel and hairspray.

The binding, though, is the really transformative part: Charlie makes me put my hands on top of my head while he straps back my man-breasts with a dozen pieces of duct tape, first horizontally and then vertically. This forces me to stand up straight and hold my chest forward, and my entire gait is changed. No longer am I the round-shouldered wimp. I have no idea what it is like to be a manly man, and I suspect this is as close as I'll ever come to the reality. I broadly swing my shoulders and arms as I walk—I feel intimidating and potent, for maybe the first time in my life.

I ask them if they act more masculine while they're in drag, and they all say yes. I ask why and several of them grab their crotches. "It's the penis," they say, almost in unison. Charlie says, "Our prosthetics have a lot to do with it, but it's a combination of everything. The facial hair, the stuffing, the binding."

Then, one by one, and with a kind of naughty schoolyard glee, the Knights show me their prosthetic penises. Derek's penis is color-coordinated to his brown skin. I especially like Charlie's, which he jokingly refers to as "the average white male." It is tiny and almost pointer-finger thin. Leave it to the biological women to actually get penises that are in character with their personas. Most men would just buy the 13-incher.

The packing part is unnecessary for me, of course, but they give me some sunglasses and a giant gold cross and stand back to admire the man I have become. I look in the mirror and see something that could have been, if a few chemicals were apportioned differently in the womb. The binding makes my shoulders look prominent, and my beard points down at my barrel chest. There is still no hair on that chest, but there is some on my face, and even the hair on my head seems like an act of aggression (at least against gravity). I look like I don't give a fuck, and it doesn't even strike me as ironic that I had to travel to a different city and sit through 45 minutes of intensive cosmetic work to get that way.

That said, when I try to walk, natural order pretty much restores itself. Kelly, the photographer, bursts out laughing and then explains that I am "gliding like a model" and not walking like a man at all. Derek tries to demonstrate a pimp walk, and the other Knights just laugh my walk off, but Kelly is right: Even in drag as a man, I am a failure. These women with rubber penises in their pants are more manly than I will ever be. I could swagger and drawl and strut, but it would always be a bad act by a nonactor, more parody than reality.

Being masculine is kind of like being cool. It isn't really something that you can adopt; it is something that others perceive and reinforce. This doesn't mean that conservatives who swear that men are a certain way and women are another way are right. Just because you're masculine doesn't mean that you have to be a douchebag. In fact, most of the douchebaggery that's prevalent in so many men comes from the privilege that comes from being born a man, not from masculinity itself. Those little cues—the liking of sports and the scratching of balls—have to do with more mysterious things, like personal taste. Why does a 3-year-old child suddenly decide that he hates mayonnaise and then carry that hatred all through his entire life? Who can ever say? And when it comes to those cues, when I pay real attention to myself, I learned that I've got a few of my own. When Kelly and I were driving around trying to find On the Rocks, we got lost. She wanted to stop at a gas station and ask for directions. I flat-out refused. We can find it on our own, I said. And, goddamnit, I was right. recommended