“My personal experience with carrying two sets of role expectations—
male as well as female—has taught me that both sexes enjoy certain
privileges and both sexes have their crosses to bear.” — Cat Saunders
By Cat Saunders
I can’t say I really know how it feels to be a man, because I’m a woman. But I did cross-dress a few Halloweens in a row, just to see what it’s like to appear as the opposite sex. It was quite an eye-opening experience, to say the least.
In the last couple of decades of adult life, I’ve used Halloween to explore some aspect of my psyche. Usually I like to explore a part of me that doesn’t get enough “press time” in ordinary life. On two or three different occasions, for example, I dressed up as a fool in harlequin-colored leotards with a purple cape, bells on my toes, and gold stars on my face.
On another Halloween, I dressed as a mime. I covered my face in white greasepaint. My body was totally “exposed” in a silver-white leotard, like some hairless two-legged animal. Being a mime celebrated the part of me who, in fact, enjoys being more like an animal. By that I mean all action and no words.
One of my favorite Halloween costumes was to dress like a man. I’ve done many years of work cultivating my “inner male,” and people often tell me I look androgynous. Men’s clothing often fits me better than women’s. And customer service representatives sometimes call me “sir” when they hear my voice on the phone for the first time. That always makes me laugh.
When I was doing a lot of personal growth intensives in the mid-eighties, one of my mentors told me to read The Hazards of Being Male in hopes that it would help me understand my (now former) husband. Much to my mentor’s and my surprise, I identified with the male perspective all the way through the book. That made me realize I was raised with both sets of gender expectations, in terms of personal and professional roles.
I’m mentioning this because my personal experience with carrying two sets of role expectations—male as well as female—taught me that both sexes enjoy certain privileges and both sexes have their crosses to bear. I found out more about this on a visceral level when I dressed up as a man on Halloween.
In preparation for my cross-dressing costume, I combed secondhand stores looking for a man’s three-piece suit. I couldn’t find any good suits. So I hit on the idea of dressing up in men’s clothes borrowed from my longtime companion, John Giovine.
John has owned and operated his own shop as an import mechanic since the mid-1980s. So he had plenty of “mechanic’s blues” on hand. With three layers of shirts and a Volvo jacket on top, I concealed my curves and padded my torso enough to fit into John’s clothes. I have big feet “for a woman” (or so I’ve been told), so I only needed two extra pairs of socks to fit into his shoes.
After I got the clothes right, including a dirty red shop rag hanging out of my back pocket, John helped me do my face. First I smothered my hair in mousse and parted it on the side. Then I brushed it flat against my head, like a true grease monkey. Next, John painted a beard on my face. He’d spent a couple of years in theater during college, so he knew how to make a great “five o’clock shadow.” To do it, he used a dry sponge and black greasepaint.
When he was done, I gave myself a moustache and thickened my eyebrows using the same technique. When we finished, I looked at the overall effect and gasped. I actually looked like a man! The funny thing was, I was attracted to myself. I felt as if I was looking at my soulmate in the mirror. In a way, I guess I was.
The first year I tried my cross-dressing costume, John and I were invited to a party the weekend before Halloween. It was at the home of a former husband named Frank. I figured I probably wouldn’t know anyone there besides Frank, so it seemed like a good place to experiment with cross-dressing.
When we got to Frank’s house, we were greeted by a roomful of all kinds of people. And I do mean all kinds—including a few extraterrestrials. I didn’t see Frank anywhere, so I introduced myself to a group of people and they introduced themselves to me. The first thing I noticed was that the women weren’t giving me that “Who are you, and what kind of competition are you?” look.
Instead, they all seemed to treat me as if I was actually a man, even after they found out differently. It was weird! It was as if the beard and mechanic’s getup triggered more social conditioning than their conscious minds could overcome.
I also noticed that the women at the party seemed to hang on every word I said. This was much different from what I’m accustomed to as a woman. Perhaps I was suddenly more fascinating that evening, but I doubt it.
Men at the party had several different reactions. First of all, there was Frank—a man I spent seven years with. When I finally located him out in the back garden, I stood inches away from him and he didn’t know who I was. That was pretty incredible! When I laughed, he suddenly realized who I was. But before then he didn’t have a clue, so I knew the costume was effective.
Other men at Frank’s party regarded me with great curiosity. A few told me that my appearance was “rather unsettling.” None of them reacted to me as a woman, however. None of them showed any no sexual interest toward me.
John and I left the party for a little while to pick something up at the local grocery store. At the store, I noticed that straight men appeared to have two different kinds of responses to me. One response was to ignore me. In this case, I honestly couldn’t tell whether they didn’t realize I was a woman, or if they thought I was gay. Either way, heterosexual men showed no interest in me.
On the other hand, some of the men in the grocery store seemed to realize I was a woman. These men shot me a powerful glance that seemed to say, “How dare you try to pass as a man without actually being one!” Of course, I have no way of knowing what they were actually thinking, because I didn’t interview them. But you know how you can just feel the meaning of someone’s look? It was like that. It was as if those men regarded me as some kind of threat to their precious male territory.
What was curious to me about people’s reactions—whether from men or from women—was this. In all cases, people regarded me with more respect than I’m used to receiving as a woman. This was true whether or not the men and women seemed to like me as a man. The extra respect accorded me as a man was quite palpable.
I thought a lot about my experience dressed as a man in contrast to what often happens in our society when a man cross-dresses publicly as a woman. In most situations, such a person would be ignored, at best. More likely, he (she) might be ridiculed or shunned, or worse, harassed or even attacked. These kinds of double standards around sexual orientation make me very sad.
After the party at Frank’s, John and I went up to Capitol Hill, which has a higher ratio of gays than most of the Seattle. We ended up at a gay bar called The Ritz. Some of the men in the bar were cross-dressed as women and didn’t even notice me. Others who did notice me had a fascinating reaction. Their bodies seemed to instinctively know that I was not a man. In these cases, I perceived no sexual energy coming from them toward me. They were obviously more interested in John.
The strange thing was, even though their bodies knew the score, their conscious minds appeared to be working furiously to figure out exactly what I was. Apparently, I was attractive enough as a guy that I turned heads when I walked into the room. But the men’s feet stayed glued to the floor. No one approached me with any pickup lines. This was in contrast to the women at Frank’s party, some of whom came on to me as a man!
Two nights later, on the actual day of Halloween, I had yet another powerful experience with cross-dressing. John and I were scheduled to go over to the house of one of my closest friends, Naomi (not her real name). We had an appointment to meet with her and a couple of her colleagues to discuss some business ventures.
I didn’t tell anyone that I was going to dress as a man. When we arrived, Naomi hadn’t gotten home yet, so her two friends—a straight couple—greeted us at the door. I’d met her friends once the day before, but John hadn’t met either of them.
Naomi’s friend Paul opened the door and greeted us. Later, he told us that when he saw us standing there with our arms around each other, he simply thought, “Oh, I wonder who these two nice-looking gay men are.” He said he didn’t realize who I was for several seconds. Meanwhile, Paul’s wife was completely baffled. She stood there staring at me for about a minute, until I laughed. Then she knew who I was.
After a while, I heard Naomi unlocking the front door to come in. I moved to a place in the living room where she could see me as soon as she entered. When she did, she dropped her keys, gasped, and jumped back in shock. She had just come from a support group and was feeling vulnerable. She was clearly expecting to see me as a woman.
I was well aware that Naomi had been physically, emotionally, and sexually abused as a child. But I did not know—until that night—that one of the stepfathers who had committed the abuse had been a mechanic. Even though Naomi quickly realized I was in costume, she was unable to overcome the appearance of me as a man. This was especially true because I was dressed in traditional mechanic’s blues.
Naomi regarded me with suspicion, fear, and anger. She wouldn’t allow me to hug her or come any closer than three feet away from her. Although I completely understood and respected her boundaries, the experience was profoundly disturbing for me. I got a sense of what it must feel like to be a man who is truly safe, yet is mistrusted simply because of his gender.
It was hard for both Naomi and me to feel distanced from each other because of my “man” costume. Still, physical appearance is a powerful and mysterious thing, cultural stereotypes or not. After about a half hour, I decided to wash off my makeup. When I came back, Naomi was immediately able to let me come close and hug her. The fear was gone from her eyes, and it felt good to feel her warmth toward me again.
A few days after my Halloween experiments, I got the pictures printed at the local photo finishing shop. I showed them to some of my longtime students and clients. They were amazed. Pointing to one of the pictures of me as a man, one of them said, “I wouldn’t tell that person what I tell you!”
And I laughed again.
This article was adapted and updated from a piece originally published by Spiritual Women’s Times (Winter 1988) and updated in June 2017.
Cat Saunders, Ph.D., is a counselor in private practice in Seattle, Washington. She is also the author of Dr. Cat’s Helping Handbook: A Compassionate Guide for Being Human (available through Amazon). Contact Cat by emailing her or by calling 206-329-0125 (24-hour voicemail).