Straight Sex with a Cross Dresser
"Eyeliner and Lace," a Dirty Martini story by Lauryn Bee
Shelley had not intended to spend her Friday night in a drag club.
She had been taken by surprise; that was the story she was sticking with. When Amanda had popped her head over the tall front desk, Shelley had been busy filing away the last of the day’s paperwork. She didn’t work on Saturday or Sunday and was eager to leave the library, return to her apartment, and forget the annoying patrons and her sore feet until Monday.
“You!” Amanda boomed.
Shelley let out an involuntary shriek and dropped the unruly stack of late fee receipts she had just wrangled into order. Amanda laughed apologetically until Shelley recovered herself enough to croak out a weak, “You scared me,” and ask what her coworker wanted.
“You,” Amanda repeated, launching into what clearly was a prepared speech, “are coming out. With me. Tonight.”
No, I’m not, Shelley thought, but because she couldn’t think of a nice way to say so, she said instead, “Oh, Amanda, that’s really nice, but—“
“It’s not an offer.” Amanda might have been tall and thin, but she was no pushover. Now, with her red hair flowing and her hands on her hips, she looked like an adamant, cinnamon-colored bulldog. With a French manicure. “I’m not going to spend my entire weekend knowing that you, my dear friend, are parked on your couch watching some god-awful, twenty-hour-long Jane Austen costume abomination from the BBC, with no booze and no prospects, while I’m trying to tie on a perfectly respectable good time.”
Well. Shelley had planned on Sense and Sensibility, and maybe on finishing the pair of socks she was knitting, and definitely on some tea, but there was no way she was about to tell Amanda that now. Not that there was any need to, apparently. “It’s just been a long day,” she said, “I’m—“
“Tired? Like every Friday when I ask you to come out?” Amanda smirked. “That’s not working this time, Shelley. I’ll pick you up at your place at 9.” She hitched her purse higher up on her shoulder and turned to flounce off, then remembered: “We’re going to The Pearl Necklace, so spiff up.”
“The Pearl Necklace,” Shelley muttered to herself later, standing in her robe in front of her open closet. That didn’t sound scary at all, nothing like the sort of place she always imagined Amanda went after library hours. Much more tea and croquet, must less body shots and table dancing. Altogether more her thing. She even ventured a smile as she pulled her grey pencil skirt up her round hips and slipped into a lacy camisole and rose pink cardigan. She fixed her blonde hair back into a stylish ponytail in the mirror before pulling on her peacoat and running to meet Amanda’s insistent beep-beep on the horn. Maybe she’d have fun, after all.
As Amanda led her by the wrist into the cloying, smoky darkness of the club, however, Shelley’s visions of an evening amongst nice, civilized society were shattered. She had the unpleasant sensation of having been dragged bodily into some Cabaret, neo-Victorian, black velvet nightmare, full of people she’d never imagine sitting beside on the train, much less talk to. She was absolutely certain that she had made a mistake and should have stayed home with the BBC.
Amanda smiled luxuriantly and pulled off her coat, revealing more cleavage than Shelley knew Amanda had. She shook out her hair, turned to Shelley, and asked, “This is great, right? Well, come on; let’s see what you’re wearing.”
Shelley slipped each arm slowly out of her coat, revealing the now ridiculous cashmere sweater she’d been so proud to buy with her last paycheck.
Shelley expected Amanda to screech at her, so it was a relief when she simply looked disappointed, muttered that there was nothing to be done about it then, and led Shelley to one of the tiny round tables littering the room.
Shelley glanced around, looking more closely at the bar. Now that her eyes had adjusted to the gloom, she could pick out more detail: The corsets and ornate jewelry on some of the women, the light glittering of martini glasses, the. . . Oh, no. This was definitely out of her league.
Shelley hadn’t been to many bars, but she was sure that something was amiss here. Instead of cocktail waitresses in low-cut shirts, a gaggle of men paraded around the room, balancing black trays of drinks and wearing—could it be?—heels, garter belts, stockings, lace panties.
“Amanda,” Shelley hissed, mortified, “You didn’t tell me we were going to—to a gay bar!” She looked around as though she thought someone might have heard her and was going to kick her out. Though that wouldn’t have been such a bad thing, she considered.
To her chagrin, Amanda just laughed. “This isn’t a gay bar,” she said, comically matching Shelley’s tone of scandal, “it’s just a bit of fun. You know, like Rocky Horror Picture Show, that sort of thing. Relax.”
Shelley did not want to relax. But before she could voice further protest, a distracting bulge appeared in her periphery. Almost of their own volition, her eyes traveled up from the black lace barely containing the waiter’s package, along the smooth lines of his flat, pale stomach and over the curve of his shoulders. His name was written on his left pec in what looked like liquid eyeliner: Mark. She took in his face in reverse, noticing first his thin lips, painted dark red, working up over his nose and to his eyes. His eyes. Even in the gloom they burned bright blue against the dark eyeliner and shadow, staring into Shelley’s from under strong brows. He tossed back an errant lock of black hair and asked, “Can I get you ladies something to drink?”
She hadn’t thought his voice would be so deep. It made her think of hot caramel, of warm sheets, and then she realized that Amanda was saying something. . .
“Shelley? Shelley!”
They were both staring at her. Save face. “Huh?”
Amanda grinned up at the waiter. “Um, she’ll have a vodka and cranberry, too. Thanks.”
Shelley watched him saunter back to the bar to place their orders. His heels clicked audibly as he walked, but all she could focus on was the white flesh peeking over the tops of his thigh-high fishnets.
Amanda made a guttural, feline sound of appreciation. "Phwoar! I wouldn't mind letting him riffle through my top drawer!"
Shelley whipped her head around and shushed Amanda. What if someone--what if he--heard?
"What, like you didn't notice?" Amanda's expression shifted from skepticism to a bright look of revelation and sudden potential. "Hey. You want him?"
It took a second for Shelley's mind to make the leap and understand what Amanda had just asked her. Then, all she could imagine was the two of them in the club store room, her pushed up against a wall as he lifted her leg up over his hip, opening her as he pushed himself inside. . . The familiar heat of embarrassment left her face, trickling down her body and settling into something less familiar and decidedly more pleasant.
Amanda grinned. "Well, we've got to do something about what you're wearing. Go in the bathroom and make yourself presentable." Her eyes flickered over Shelley's shoulder. "Here he comes! Go! Go!" she barked, like some sex drill sergeant.
Shelley examined herself in the bathroom mirror. Suddenly, the cashmere cardigan she'd spent her last paycheck to buy seemed ridiculous. One by one, she undid the pearl buttons, revealing the sheer camisole that hugged her curvy waist and did nothing to hide her erect nipples. She tugged her thin underwire bra into place so that it pushed the tops of her breasts to peek over her frilled neckline. Then she pulled out her ponytail and shook her hair so that the curls settled around her shoulders. She scrutinized her new reflection and decided that it wasn't half bad. At least with her hair down she didn't feel so naked.
When she returned to the table, the drinks were waiting and Amanda emitted a low whistle. "Much better!" she said. "Now. You have to go talk to him."
Shelley nodded, stood, smoothed the wrinkles from her skirt. She could do this. Just a few yards and she'd be standing right in front of him, her eyes even with his Adam's apple, her hands closer to something else. She imagined hooking her fingers underneath the elastic waistband of those silly lace panties, pulling the black fabric lower. She imagined how thick his cock would be and how warm it would feel as she took it in her hand. One more step, and another. Almost there. She could feel her pulse pounding in her neck and the heat creeping up.
I can't do this. Shelley swiveled around on her heel and stiffly speed-walked back to the table. She sank into her seat, grabbed her vodka and cranberry, and, pushing the straw aside, downed a gulp large enough that she coughed and sputtered.
When she looked up, she saw Amanda glaring at her.
"What the fuck was that?"
Shelley wiped her mouth on the back of her hand. "I can't do it," she said, then added, "I want to go home. Now."
Amanda crossed her arms. "No."
"Yes. Please."
Amanda was quiet for a moment, then said, "I knew you would do this." She had never sounded so angry. "I knew it. You always hide, you always push everyone away. What are you so scared of? God, Shelley, you're gorgeous, you're young, but you live like you're eighty."
Shelley wanted to defend herself, but the words stuck in her throat.
Amanda watched Shelley, waiting for her to say something. Finally, she reached into her clutch and pulled out a wad of money, which she thrust across the table in Shelley's direction. "Here's cab money," she spat. "I'm going to go dance." She stood, grabbed her drink, and stomped away in search of more exciting company.
Left alone, Shelley felt miserable and horrifically conspicuous, sure that everyone in the club had heard Amanda's accusations. Her mouth opened and closed, fishlike, as everything she could have said to Amanda ran through her head.
It wasn't true, what Amanda had said. It was unfair. Who was she to judge Shelley? Why had she even dragged her out? The sick desire to humiliate her, to make her chase after some waiter neither of them even knew? Pity?
Pity. That would have been the worst. It would have meant that Shelley was some overgrown child, too scared to go out on her own. It wasn't like she couldn't manage. She'd had dates.
Shelley took another, smaller, drink, feeling more confident and more angry. She wasn't some virgin in need of worldly-wise Amanda and her contacts in the world of thrilling sex. She'd had plenty of sex, great sex, in fact. . . Haven't I?
Shelley tried to recall one truly amazing night, one scandalous escapade. She'd walk right up to Amanda and throw it in her face, she thought. There had to be something.
But nothing came to mind, either especially good or especially bad. Nothing remarkable at all. A short--but respectable--list of names and their corresponding bland, good-natured faces, men she'd met through family and through friends from college. Commonplace dinners and romantic movies--she knew her dates had picked them for her benefit--followed by ten to twenty minutes of normal, kink-free sex. She could have mapped the encounters on some perfectly ordered chart: the kiss, the hand on her breast, the fumbling off of clothes, the sedate in and out. Perfectly orderly. And perfectly boring.
Shelley drew the last drops of pink vodka up through her straw. A slight, tingly warmth suffused her body, rendering her not quite drunk, not quite as angry, and just fuzzy enough to actually do something. She wasn't much of a drinker, but, she thought, this wasn't too bad. Where's that waiter?
There. Shelley caught his eye, and her hand lifted itself of its own accord, beckoning him to her table.
"Yes?" he asked.
Even that safe monosyllable sent a lick of fire across Shelley's thighs. She ignored the urge to run, and smiled back at him.
"I'd like another one of these," she answered, indicating her empty glass.
"Anything else?" he asked when he had brought her drink.
"Yes." She almost heard the purr she'd heard sometimes in Amanda's voice when she was describing weekend adventures that usually made Shelley blush and glance around to ensure that no children were within earshot. It was almost easy. "I have a question."
He lifted one eyebrow, wary but inviting her to continue. It was amazing how much the lipstick added to his smirk. Shelley realized that she didn't mind the makeup at all.
"Why this?" By gesture of glass and eyes, Shelley indicated the entire length of his tarted-up body. She wanted to giggle when he inadvertently looked down at himself. It was cute, almost childlike. Unlike what she saw herself doing to him later.
"It's fun. The tips are good." A pause. "And I get to be practically naked in public. In front of gorgeous women. Without getting arrested." He grinned.
"One more question." Shelley bit her lip. "When do you get off?"
"Soon. I hope."
He looked different with clothes on. When he met her after his shift ended, he had put on jeans and a blazer, an old-fashioned driving cap, a threadbare T-shirt that spoke of comfort and innumerable spin cycles. Shelley didn't care. He'd wiped off his lipstick, but he'd left on the dark eyeliner. Even though he now looked more like someone Shelley would normally have gone for, those black smudges reminded her that he got ready for work by pulling on lingerie she would have been embarrassed to look at in a store. It made him naked even when clothed.
"Your place?" he asked.
Shelley thought of her apartment, with its handmade afghans, overzealous collection of dachshund memorabilia, and its dust ruffle.
"Yours," she answered.
Was it stupid to go home with a man she didn't know? Yes. But she didn't stop him when he hailed the cab, when he held the door open for her, when he gave the driver his address. She had been smart her entire life. She was due her share of being stupid. And she decided to begin by kissing him. Right here, in the cab.
She had never kissed like this in public, holding his face in her hands as much to feel the scruff of his cheeks against her palms as to keep him from pulling away. She didn't recognize her voice in the hungry noises that came out of her throat and found their way into his, and she didn't want to. What she wanted was to never stop taking in the taste of his mouth: cloves and the waxy flavor of leftover lipstick.
When the driver stopped, Shelley tossed the money Amanda had left her toward the driver's seat. Mark led her up the sidewalk at a run, grasping her hand. The length of his fingers made her feel tiny. In the elevator, he punched in the correct button with his thumb then pinned Shelley against the wall, kissing her neck. The full length of his cock pressed against her thigh.
Her senses sharpened and distilled the world into a series of rapid-fire vignettes. Elevator doors sliding open. Keys jangling, the lock grating open. A white tunnel of hallway. Her arms up, her shirt off. Mark's lips. His underwear--boxers, she couldn't decide if she was disappointed--sliding down his long, skinny thighs. His hands, pressing her down onto the mattress. The rustle of the sheets and the parting of her thighs.
Fear gripped Shelley. She felt guilty suddenly, as though she were acting, lying. She should warn him, should tell him she didn't do this, that this wasn't who she was.
But then he was inside her, and Shelley forgot what she had wanted to say. Why had she ever talked in her life, when it was so much better to be incoherent and wordless, digging her nails into the soft skin of Mark's back as he stretched her wider and wider with each practiced thrust?
Shelley spread her legs wider and hooked her calves around the backs of his knees. She tilted her hips up to meet his, taking him in deeper. He groaned into her ear and slammed into her faster.
But it wasn't enough to lie there. It was too much like all of the boring dates before; it wasn't what she had imagined when she had watched him in the club, balanced and restrained on his high heels. She had wanted him unbridled, but she had also wanted to feel unbridled herself. She had wanted what he could make her do.
Rough Terrain by Mick Payton (prints available at ObsessionArt, starting at $39.20).
Shelley had never considered herself strong, but carrying stacks of books must have paid off, because she grabbed Mark's wrists and easily pushed him over onto his back. Now she was the one pinning him down, and she didn't know what she liked more, the hot, wet pressure of his cock inside her or the shock she watched slap him across the face.
She loved knowing that he couldn't move; that with her heavy breasts hanging low over his face, he couldn't see anything else; that on top, she could find her own rhythm. She squeezed her pussy tighter around his cock, swiveling her hips as she rode him. She could feel his hips struggling to buck upward, but she wouldn't let him have his way. She refused to relinquish her hold.
She hadn't expected revenge. Mark strained his head upward and caught her right nipple in his mouth. His tongue drew circles on the dimpled flesh. Shelley's resolve wavered with each slow, lazy lap of his tongue, until finally she had to give up. She let go of his wrists and leaned backward, exposing the hard mound of her clit. She touched it gingerly, then harder, seizing with a shudder of pleasure. His hands gripped the smooth, round cheeks of her ass and pulled her down onto him as he thrust upward, free again. She only caught one brief glimpse of him with his head thrown backward, lower lip clenched between his teeth, before her own orgasm gripped her, forcing her eyes shut and drawing out a scream.
The old Shelley would have been embarrassed to have been so loud, but that person didn't exist anymore. Somewhere between the eyeliner and the lace, she had disappeared, gone on what would hopefully be an indefinitely extended vacation.
Originally published June 2011