Chapter Seventeen

The Cross-Dresser

Stage one is packed, Marilyn Manson blasting through the sound system. Every chair is full and the crowd is raucous. As the beat crescendos, strobe lights flash and money rains from the sky. A man sitting at the end of the stage places a folded five-dollar bill on the tip rail. I crawl toward him, my eyes locked on his. I see him swallow and lick his lips. In his eyes, I am the only thing that exists.

He is white, early fifties, with thick grey hair pulled back into a low ponytail and a matching grey beard. He looks like any average white, middle-aged, American male, little stomach pushing over his belt but otherwise fit. Except that he’s wearing women’s clothes.

Large glasses with pink frames cover his eyes; they are of the early 1980s style still favored by my grandmother. His blouse is a complementary peach paired with a mid-calf grey skirt, tan pantyhose, and low black heels. As I approach he slowly reaches up and unbuttons the blouse, one faux pearl button at a time, until I can see the top of a functional white bra. It’s stuffed, pushing out the front of his shirt over a flat chest covered in grey hair.

My gaze never wavers, the small smile curling my lips widening slowly. But behind my seductive gaze my brain is whirling. I know that cross-dressers are almost exclusively cisgender, heterosexual men. Drag queens are of a different category entirely but cross-dressers are often assumed to be gay. I know that they’re not, but I have never before encountered one. I’m powerfully curious.

I kneel before him, wearing only a G-string and heels. His eyes travel up my body, lingering on my belly, up over my breasts, to my face. He licks his lips again. I rotate my hips slowly and his gaze drops to the slow gyration of my pelvis. When I pull the string of my thong out, he places the five-dollar bill against my hip, conscientiously avoiding touching my skin.

Before I can move away, he peels a second five from the roll in his hand, but instead of placing it on the tip rail, he inserts it into the exposed edge of his bra. I laugh and he smiles back. We are not supposed to take money with anything other than our hand, and so I lean forward, placing a hand on either shoulder, bringing my chest close enough to feel his breath. Holding myself with one hand, I run a fingertip down his chest, covered in wiry grey hair, and under the top of the elastic. I feel him take a quick breath. Slipping the bill out of his blouse, I let my breath tickle his ear and then flip neatly backward, somersaulting away.

After my set I quickly skirt the stage, thanking the customers for the tips. The man still sits at stage, but he’s tipped over $10 for a single set and so I pause and ask his name.

“Doug,” he says and then gives a small shake of his head, as though correcting himself. “But can you call me Donna?”

“Donna.” I hold out my hand and he shakes. I notice that his nails are carefully manicured and painted pale peach. “I’m Nora.”

“I’m so pleased to make your acquaintance,” he says.

“Likewise,” I reply. “If you want to have a drink together later, let me know.”

He glances at the stage where Bambi is working her magic. “After this set?”

“Sure,” I say and step away. That stage is now the territory of another dancer and I try not to poach. I catch Bambi’s eye and she tips her chin toward me. I lean in over the stage and she hugs me, her body against mine.

“What’s up with the faggot?” she purrs in my ear, her hair hiding our exchange.

“He’s not gay,” I say, biting back irritation. “And he’s loaded.”

“Fair enough,” she says and releases me.

I go to the bar and watch Bambi dance. I notice that she doesn’t stay in front of Donna long; for each customer at the stage she performs for a minute or two depending on the size of the tip. With Donna she turns her back, twerks her butt, and moves on. He gets up and leaves halfway through her second song.

I give the waitress a nod and walk to the table he’s taken against the wall with a good view of the stage action. “May I sit with you?” I inquire and he nods enthusiastically, leaping up to pull my chair out for me.

“So. Donna.” I rest my chin on my hand, looking up at him coyly through my eyelashes. “I haven’t seen you in here before.”

“I haven’t been in for a while. You’re new.”

“I am, I guess. I started a few months ago.”

“You’re so beautiful,” he tells me.

“Thank you,” I say. “I like your top.” I don’t, but flattery works a variety of magics.

His smile widens. “Thank you so much!”

I can tell that he’s not complimented a lot.

“But do you think this color goes with grey?”

“Hmm.” I narrow my eyes as I consider the outfit. “It depends on what you’re going for. It’s very office chic.”

“Like what a secretary would wear.” He nods, satisfied. “I think office girls are sexy.”

“Are you an office girl?” I shoot him my best suggestive smile.

“Why?” He flutters his eyelashes coquettishly. “Do you think office girls are sexy?”

I laugh. “That depends on the office girl.”

He laughs along with me and then returns to my question. “No, I am not an office girl. I’m a lawyer.”

“Oh, I have a cousin in law,” I say. I always try to make personal connections. “He likes it. What do you like about it?”

He considers. “I like helping people,” he says finally. “I feel like I’m making some small contribution when I can really make people feel like someone’s in their corner.”

“That’s beautiful,” I reply honestly. “What kind of law do you practice?”

“Mostly workers’ comp cases. People who have been jerked around by their employers after being injured—I like to help them get the care they need.”

“Do you ever get people you think are lying? Or injured themselves out of real negligence?”

He shrugs slightly. “I find that most people are honest.”

I nod. “I find that, too.”

“Even working here?”

“What do you mean?”

“I just assumed …” He pauses, searching for the right words. “Don’t men try to take advantage?”

I laugh. “Oh, yes. But they’re honest about it! Most of the time they tell me exactly what they want, or what they want to do to me. Then I get to say yes or no.”

“Then let me be honest with you.” He leans across the table and takes my hand.

“Okay.” I lean in, matching his serious tone.

“Do you have a gown? Something elegant?”

“I do.”

“Can you change into it and give me a private dance?”

I grin. “Of course.” He releases my hand and I stand. “I’ll be right back.”

In the dressing room I peel off the black vinyl micro skirt and crop top I’m wearing and root quickly through my locker for a floor-length gown in emerald velvet. Its halter top is crusted with rhinestones and a slit runs up one leg to my thigh. I pair it with a pair of patent pumps and silver bangle bracelets.

His eyes light up when he sees me. “That’s perfect! You’re so elegant.”

I hardly think that skintight velvet qualifies as “elegant,” but I keep my mouth shut. Stripper elegant, maybe.

I take him to the private dance section and sit on the edge of the small stage while he situates himself in the cushy chair clients sit in.

“May I ask you a question, Donna?” I ask.

“Shoot.”

“What pronoun do you prefer?”

He positively glows at my question. “Thank you so much for asking!” he exclaims. “That is so thoughtful! I am a man and I identify as ‘he.’”

“That’s what I thought. But I wanted to be sure since you prefer a woman’s name.”

The next song begins and I begin my dance. I keep the gown on, seeing how his eyes are drawn more to the garment than my body. I play with the clothing, squatting, legs apart, so that the slit gapes open, flashing the rhinestones on the velvet thong I wear underneath, untying the straps but letting the top ride low on my breasts while still covering me. Only at the very end do I let the dress glide down my body to puddle on the floor at my feet.

When the music ends, Donna claps long and hard. “That was wonderful!” he gushes.

I’m amused and touched by his appreciation. I’m getting the feeling that he needs to feel seen for who he really is.

“May I have another dance?” he asks, handing me a 20-dollar bill.

I check the dancers on stage. “I have to go to stage here in a bit.” His face falls. “But right after?”

“Yes! That’s great.” He takes my hand again. “Thank you.”

“For what?”

When he looks shyly back up at me, I meet his eyes steadily.

“For taking me seriously.”

“Lots of people don’t?”

He shrugs and looks down. I see his chin quiver. “I come here because most people don’t treat me any different than anyone else. But only some of the girls will dance for me. And some guys threatened to beat me up in the parking lot once.”

“That’s awful.” I give his hand a squeeze.

He glances at me very quickly and I see tears in his eyes. “It’s okay. Donnie came and rescued me.”

I glance at the door where Donnie lurks, a hulking figure of at least 300 pounds of muscle. My opinion of him goes up. “Good for Donnie.”

He lets go of my hand and swipes his eyes furtively. “I just want to wear pretty things.”

I pick up the green velvet. “So do I.”

Two months later Donna asks me to go shopping with him. I’m always cautious about accepting invitations to meet customers outside of the club, and so I ask “Shopping for what?” to buy myself time to think.

He’s holding my hand, gently stroking my lacquered nails the way he likes to do. I think he likes to see his polished nails next to mine.

“Clothes,” he says. “You have such wonderful taste.”

I wonder why he thinks that, given that all he ever sees is stripper clothes. While what I wear in the club is a partial reflection of my personality, my wardrobe is a careful presentation of the femme fatale to appeal to my mostly male clientele. Red catsuits and schoolgirl skirts are not what I wear grocery shopping.

“You want me to take you shopping for women’s clothing?” I’m still baffled. His style, what he wears to the club, can only be described as “liberal granny”: sandals with white socks, tweed pantsuits, sweater sets.

“Yes!” He squeezes my hand. “I need to update my look.”

“What do you have in mind?”

“Just take me wherever you go.”

I shop mostly in thrift stores and Hot Topic. I don’t think it’s what he has in mind.

“Where do you shop now?”

“JCPenney catalog.”

That explains it. I think quickly. “Dillard’s?” I finally suggest. They have edgier items while retaining modest sensibility. Plus, I need a dress for a family reunion and maybe he’ll spring for it if I agree to take him.

“I’ll go wherever you say.”

We make plans to meet at a local mall.

Getting dressed to meet Donna takes some planning on my part. He’s cast me as a fashion icon without ever seeing how I really dress. And how I usually dress to go to class or run errands is jeans, a tank top, and flip-flops with my hair piled on top of my head. I don’t want him to see me and realize that he’s made a terrible mistake.

I settle on skinny black jeans, motorcycle boots, and a babydoll T-shirt with “goddess” written on it in red glitter paint. I brush the makeup on heavier than usual but lighter than I wear at the club, foregoing the black eye makeup and dark lipstick. I twist my hair up into an elegant roll on top of my head.

I meet Donna in front of the mall at 11 a.m. I’ve never seen him dressed like a man, and it takes me a minute to recognize him in jeans and a white T-shirt. He looks grandfatherly with his white beard and little potbelly.

He greets me by telling me how beautiful I look and kissing me dryly on the cheek.

“So, Don,” I say, shortening the name he asked me to call him to a male moniker. “What are we shopping for?”

“What I really want is a ball gown. With all the accessories. And shoes!” His eyes light up. “But I’m not good in heels.”

“You got it. Let’s start at Dillard’s and work from there.”

I’m a little concerned about his body shape in dresses. He really is shaped like a middle-aged man, as opposed to a middle-aged woman. He turns down my initial selections as being too frumpy. He wants sexy.

I flip quickly through the plus-sized selections and find a floor-length gown in deep blue satin. It hangs almost straight from rhinestone shoulder clasps, and I like the weight of the fabric and the cut.

Donna looks at me doubtfully.

“I think it will hang really well,” I explain. “The fabric will cling just enough to make you feel really alluring and move with your body. I think you should try it on.”

At that, Donna looks truly alarmed. “I can’t.”

“What do you mean?”

“I mean …” he stumbles. “I can’t go in the men’s dressing room with that. And they won’t let me in the women’s.”

“Ooooohhhh.” I clearly haven’t thought through this whole cross-dressing thing. “Give me a minute. Stay here.”

I make my way quickly out of the women’s section and go over to lingerie. The sales clerk is a friendly-looking woman in her mid-sixties. She looks nice enough and there are no customers around.

“Excuse me,” I say. “I have a bit of a problem and I could use your help.”

She smiles warmly. “How may I assist?”

I don’t beat around the bush. “I have a friend. A male friend. He likes to wear women’s clothing.” I pause to gauge her response.

“That is a bit unusual,” she says. Her expression stays blank and warm. “What seems to be the issue?”

“He can’t try on clothing in the men’s room because … well … it can be dangerous for him. And he can’t go in the women’s room for obvious reasons. So he has to buy things, take them home, try them on, and then return items that don’t work.”

She narrows her eyes thoughtfully. “You know, I think I have just the thing.”

“Yeah?”

“We have a handicapped changing room that’s unisex. Just around the corner here. Bring your friend over and I’ll take care of you.”

I grin. “Thank you. Thank you so much.”

She smiles primly. “It’s really no trouble at all.”

I think that Donna is going to hug me when I tell him the news. He takes the sapphire gown from me and insists on trying an orange sundress with an empire waist. I think it will make him look like a pregnant orange, but whatever.

I’m right: the floor-length blue hangs over his figure in a flattering line. His wide shoulders and hairy arms look a bit odd but I’m getting used to that.

I select lacy panties (loose in the crotch area), a matching bra, and stockings with a garter belt. We hit jewelry next for a rhinestone choker and clip-on faux diamond earrings. Finding pumps with a low heel in his size is a bit difficult, but we finally agree on a pair of Mary Janes that aren’t awful.

Under the bemused eye of the sales clerk we also buy a whole array of skirts and tops in modern prints and fabrics. She rings everything up without ever losing her cool little smile. At the end of the transaction I ask for her card.

“If my friend comes in alone in the future, will you help him?” I ask.

“Of course,” she replies.

“Just don’t let him buy anything peach or orange,” I say. “Hideous with his complexion.”

She laughs merrily and Donna shrugs with a small embarrassed smile. “That’s why I brought you,” he says.

That Friday, Donna arrives in the full sapphire ensemble. I tell him that he looks fabulous.