Why Women Wear Men's Clothes

The three sharply dressed salesmen in Bert’s Men’s Shop make a beeline for the stunning blonde in the cutoffs and halter top who has just wandered through the front door. "Can I help you?" they ask in unison. Grace flashes a brilliant smile toward the best-looking clerk, then answers, "I’m interested in a suit."

"For your husband, perhaps?" inquires the chosen salesman as his two comrades slink away. Grace shakes her head, then points her forefinger at her large jiggling boobs.

"For me," she declares. Surprised, the young man tells her, "Oh, I’m terribly sorry, miss. We only sell men's apparel."

"You got it," chirps Grace. "I’m a 34 short."

Later, inside her studio apartment, Grace hangs the gray pinstriped suit on the back of the closet door. Anxious to try on her new purchase, she fumbles with the bows that secure her flimsy top. The halter falls to her slim waist, and her round tits bounce free. She squirms out of her clinging denim shorts, then runs her hands over her large breasts and down through the silky yellow curls of her bush.

Grace walks over to her dresser and picks out a small pair of men's jockey shorts and a roll of wide Ace bandages from the bottom drawer. She steps into the white underwear, yanking it up over her thighs and pulling it tight against her furry mound. Then, holding the end of the bandage at her cleavage, Grace begins to wrap the bandages around her chest and back, and over her full, soft breasts, painfully squeezing them together. She winces and wraps herself even tighter, smashing her firm, luscious boobs flat beneath the white elastic fabric.

From the top drawer she removes a starched men's shirt, slips it on, then has trouble buttoning it over her flattened chest. Damn, she reminds herself, the buttons are on the wrong side. Next she loops a tie around her neck, then takes down the suit-pants and steps into them. Sitting down on her bed, she slips on men's socks, then steps into a small pair of boy's black leather lace-ups. Grace stands and puts on the vest and suit-jacket, her transformation nearly complete. Gathering her long blond hair into a bun, she dons a men's hat. Then she walks to her full-length mirror and gazes at her masculine image.

Grace feels both constricted and free in her male clothing. As she stares directly at the "man" in the mirror, she senses the wetness gathering between her legs. She slides her hand into the pants and under the jockey shorts, pressing her fingers against the nub of her clitoris. She begins to rub her pussy fast and hard. With her other hand she lightly touches the slick material of the suit and toys with the silky tie. Nearing climax, she pinches her clit and twitches with delight. Drinking in her own contrived manliness, she takes a deep breath and shivers with the pleasure of the onrushing orgasm.

Crossdressing for Sexual Pleasure

Dr. Andrew Marotta, a Los Angeles therapist, ran a newspaper ad hoping to find women who were willing to be interviewed about this fetish. The ad stated that only women who crossdressed for sexual reasons should contact Marotta. He was not interested in women who routinely wore pantsuits or men’s slacks for comfort or because of the nature of their jobs. Rather, Marotta wanted to speak with women who experienced sexual pleasure from donning men's clothing. Marotta explored the sexual needs of those who identify as women and get sexual satisfaction from dressing as a man.

He found that female crossdressing is practiced by both heterosexual and homosexual women. "There are many reasons for crossdressing as practiced by both sexes," explains Marotta. "The vast majority of folks have had an experience with crossdressing at some time in their lives. Most of us have tried it as children. A young boy or girl will try on his or her parent's clothes without regard to gender, merely to see and feel what it’s like to be a grown-up. As adults, those of us who have crossdressed for a costume party have discovered the surprising power of assuming the dress (and the role) of the opposite sex."

From his investigations, Marotta has discovered that crossdressing generally can be divided into three categories. Some women, like Grace, our opening example, wear men's clothing as part of an occasional sexual fantasy or adventure. Others have incorporated men's clothing as a routine component of lovemaking but don’t need to cross-dress to get off. Others still need to wear men's clothing to achieve sexual release.

Crossdressing as a Fantasy

According to Marotta, masturbatory crossdressing is fairly common, with different women finding sexual satisfaction for different reasons.

"When Grace gazes at her masculine image," he says, "she still feels very much like a woman; she enjoys her squeezed breasts and the sensations from her clitoris. But since she looks like a man, she experiences the pleasure of having a man with her while she masturbates."

Some of the women interviewed revealed a different crossdressing fantasy that involved role reversal. These heterosexual women said they sometimes exchange both clothing and behavior with a male partner as a sexual adventure. Shannon G., a twenty-nine-year-old housewife, said that she and her husband, John, occasionally play a switching game: "We often experiment with new ways to have sex. One night John suggested that he play the woman. Since we're both about the same size, we can fit into each other's clothing, so we decided to give it a try."

"When we started making out, I made all the moves. I put my tongue in his mouth, stuck my hand down his panties and pinched his nipples. He resisted a little, but kept giving in to my advances. When I finally got the clothes off him, I climbed on top of him and controlled the fucking. The game was great for both of us—I got into taking the lead for once, and he enjoyed the passive feminine role. We've played the fantasy out about once a month since that first time."

The practice can do more than add a little spice to a lovemaking session; It can become an important turn-on. Nancy R., a thirty-three-year-old waitress, prefers to wear boy's jockey shorts and a tight t shirt more often than just during sex. "It’s not that I can’t live without the clothes," she told Marotta, "but I really enjoy wearing them."

"I have a steady boyfriend who was freaked out when I first got into bed wearing a pair of men's underwear. He asked me what was going on, and I told him that I really got off having my boobs squashed by the shirt and my pussy held by the shorts. He asked me why I didn’t just wear a tight pair of women’s underwear... I couldn’t answer that one. I don’t know—panties and bras just don’t excite me."

Crossdressing as a Sexual Necessity

The next type of crossdressing is compulsive and necessary. Some women cannot be sexually satisfied without it. Anne, a twenty-three-year-old lesbian, falls into this category. "I wear fatigues mostly, overalls, tank tops, and boxer shorts, both while I’m at work in the factory and during sex," she said in a taped interview. "Jeannie, my lover, is a frail-looking woman who wears skirts and frilly clothing."

"I always wear the underwear when we fuck, and sometimes I keep all my clothes on. I have a long, double-sided dildo that I strap on beneath the clothes and shove up my pussy, and then I use it just like a cock on Jeannie. She's always very passive and lets me do whatever I want with her during sex. It’s great to rub the coarse fabric of my clothes and my long rubber rod all over her soft little body. Sex just isn’t the same when I take my clothes off. I can’t have an orgasm unless I’m dressed up. I feel in control of her when she's naked and I’m dressed, and that feeling is what gets me off."

Masculinity implies strength and power in our culture, and by extension, so does male dress. Femininity, on the other hand, as embodied in lacy dresses and delicate underclothing, stands for passivity and submission in today's society. Many women dress like a man to display her superior position, and the symbolism can become a necessary element in her sexuality.

Crossdressers as Sex Symbols

Women who dress like men can both deaden and excite men's passions. The woman in dirty fatigues and a t shirt may be an immediate turn-off for some, but Marlene Dietrich decked out in a tight tuxedo and top hat is a classic sex symbol. One thing we can be sure of: As long as men and women are expected to dress differently, there will be people who take that difference and turn it upside down.