The speakeasy was hopping that night. The alcohol flowed like extremely expensive water and the dance floor was packed with high rollers. But all Kit Massey could do was watch the door, waiting for a certain redhead to appear.
"Are you feeling particularly dumb, that you need to go shopping for trouble?"
Kit shifted uncomfortably in her seat, adjusting her tie with a gesture that was more awkward boy than cross-dressing girl.
"Aw, applesauce," she said, turning away from Flaviana to watch the door again.
"Look at me when I'm talking to you, girl," said the blond waitress hotly, catching Kit's chin between sharp, scarlet fingernails.
"Hey, quit that noise," exclaimed Kit, jerking away. "I'm a boy, okay? Trousers mean boy, for the love of Pete!"
Flaviana smirked, eyeing her friend up and down. Kit was a tall, broad-shouldered young woman who would never be pretty dressed in skirts, but cut an extremely dashing figure in a sharp suit. At least, that's what Kit liked to tell herself anyway.
"Dumb, hick kid," muttered Flaviana. "Doesn't have any better sense than to go shacking up with Big Mike Powers' girl."
Big Mike was the muscle for the local Irish mob, the McReady family. He had made a name for himself busting heads and his girlfriend was just about the most beautiful woman that Kit had ever laid eyes on.
"I'm not shacking up with anyone, I'm just buying her some drinks" said Kit indignantly.
Flaviana rolled her eyes so far around that Kit wondered sourly why they didn't roll out of the back of her head.
"No, sweets, she's just a nun, fresh out of the convent that's here to save his sinning Irish soul, am I right?"
Kit was going to respond but then caught a signature flash of sapphire blue out of the corner of her eye.
"Well, there's Sister Charity Marie herself," said Flaviana with an exaggerated sigh. "Go knock her dead, kiddo."
"I look all right?" Kit pressed her hand against her bound breasts and managed to resist the urge to run her fingers through her carefully-styled hair.
"You look like any alley cat's wet dream," proclaimed Flaviana. "Scoot on now and do whatever damage you're going to do."
As Kit left, Flaviana turned to the bartender.
"Swear to Saint Jude, it'll end in tears and cement shoes," she said darkly. "Kit doesn't have the sense she was born with."
Helena Dunaway was no bigger than a minute, but Kit had to admit she filled every second of it delightfully. The auburn-haired beauty was wearing a tight satin sheath that clung to her like a second skin, revealing a trim waist and achingly round breasts the color of good cream. Kit's mind neatly derailed at the thought of what they might taste like and her 'Hello' was shakier than she would have liked.
"Well, hey there, handsome," purred Helena. "Have to admit, coming out to meet a poor boy like you was worth it just to see the look on the driver's face when we pulled up."
"What do you mean?" asked Kit, steering them towards a table near the tiny stage.
Helena laughed, a throaty, purring sound.
"I mean all this," she said, waving a hand around the bar.
Kit blinked and followed her gesture, seeing her favorite club with fresh eyes.
In the back, a handsome charmer that she knew ran a hophouse was chatting up a kid who didn't have the farm-dust kicked off his shoes yet. Over at another table, a well-known comedian was whooping it up with a pair of giggly things in velvet that might even have been female while a burly dockworker was buying a drink for someone in a ball gown who was definitely not.
"Applesauce," said Kit for the second time in an hour. "It's just harmless fun, isn't it?"
Helena's plump lips curved up in a cat's smile and Kit wondered whether she was lucky enough to be the canary.
"I don't do harmless fun, Kit Massey," she said.
Kit wanted to make some sort of clever, sexy retort to that, but she found that her tongue had thickened in her mouth. She licked her lips nervously, a gesture that made Helena laugh again.
Helena slid her perfectly-manicured hand over the table and touched Kit's sleeve. Kit flinched and then froze, watching Helena with a hypnotized intensity.
"Buy me a drink," Helena said, her voice husky, "and ask me for a dance. Then we're going to get out of here and I'm going to take you to a hotel and we're not leaving there 'til dawn."
"I love them stunned and silent," Kit heard Helena say as she stumbled to the bar.
"She says she's going to take me to a hotel and we're not leaving until sunup," hissed Kit as the bartender made up a sidecar.
Flaviana shook her head, only saying, "Hope you know what you're doing, hon."
As Kit collected the drink and paid, Flaviana thought of something else.
"You're, ah, equipped for the evening, aren't you?"
Kit blushed a brilliant crimson and nodded wordlessly.
"Well, then. Prepared as any Eagle Scout. Okay, good luck, slugger, and watch out for her teeth, she looks like a biter."
At the table, Helena took the sidecar with a warm smile that made Kit's heart beat a little faster.
"Thank you, handsome," she said. "Ladies love a sweet drink like this."
Helena dragged the tip of her finger along the rim of the glass, picking up the stray grains of sugar. Looking directly at Kit, she licked the sugar off her fingertip with an achingly pink tongue.
The effect of feminine delicacy was ruined, however, when she tossed the drink back in a single, long gulp. There was something about the fluidness of her body, however graceful, that told Kit that it wasn't her first drink of the evening.
Helen blotted her lips with the pads of her fingers and then stood up, offering her hand imperiously to Kit.
"Come on, then," she said. "Show me what you've got."
The band had struck up "Chinatown," a slow, insinuating number, and the couples on the floor were holding each other close.
"Not like that," chided Helena as Kit clumsily rested her hand on Helena's waist. Helena stepped closer until her pointed shoes were nearly between Kit's boots and Kit could feel every grazing touch of Helena's body on her own.
"Now isn't that better?" she asked and Kit could only nod.
The top of Helena's head only came up to Kit's chin, and when the redhead looked up, Kit was lost in her sparkling blue eyes and pretty little mouth. Up close, she could see that Helena had a small splatter of freckles on her slightly snub nose. Kit found them cute and she was lost in thought, wondering where else Helena might have freckles. Helena's words caught her off-guard.
"Like the view?"
Kit was going to murmur something soft and appreciative when she realized she also had a breathtaking view of Helena's mostly exposed breasts.
"Very, very much so," she said honestly, still staring.
"My eyes are up here, Kit," remarked Helena.
"I know where your eyes are," admitted Kit without thinking. Blushing at what she had just said, her head snapped up, but Helena was laughing.
"My, my, you really are a hick, aren't you? Oh don't look so wounded," she said at Kit's hurt look. "It's nice. Boys like you are so direct. It's refreshing."
Still not sure whether to be offended, Kit kept her mouth shut until the end of the song, concentrating instead on the feel of Helena in her arms, how Helena found a way to press every part of her body along her own. By the time the dance was over, Kit was surprised that steam wasn't coming out of her collar, and that she could even walk.
When the music ended, Kit reluctantly let her go, but Helena seized her hand, not even bothering to go back to the table. Kit started to open her mouth, but then permitted herself to be dragged out, only pausing to wave at Flaviana, who watched worriedly from the bar.
The room they got was much less grand than the cathedral-like lobby had promised, but all that Helena seemed to care about was the lumpy double bed. She threw herself facedown on it, kicking off her shoes and heaving a dramatic sigh.
"C'mere, baby," Helena said, her voice only lightly slurred. She glanced over her shoulder at where Kit was standing, a predator's glint in her blue eyes. Kit's breath caught at that riot of messy auburn hair, and at that moment, she wanted nothing more than to bury her hands in it, to use it to drag Helena's luscious little body closer to her own. Instead, she gripped the satchel that she had slung over her shoulder a little tighter.
"I...I have to use the john," she stuttered, her voice higher than it should have been.
"Well, hurry up, then, or I might start without you," said Helena, mischievously.
She flipped over onto her back and teasingly inched her skirt higher until Kit could see the top edges of her silk stockings and the clasps where the garters snapped on. With an impish smile, never taking her eyes from Kit's face, she eased her hand under her dress. Kit could see the outline of that hand moving under the slippery fabric and it felt like the top had blown off her head.
"Be right back," she said, making it sound like a plea.
Helena's laughter followed her down the hall to the floor's washroom, where Kit locked herself in with a sigh of relief.
She opened the satchel and took out the rubber cock with the flared base and the confusion of leather straps. She had to slip out of her trousers and shorts to get it on and she silently thanked the hotel for having a real door and not just a curtain. She had had a very bad moment with curtains in the past, but the person who had inadvertently walked in on her was a junkie who hadn't been in the least surprised to see that her penis was detachable.
When strapped into place, it rested comfortably low between her legs, though it did stick out at an embarrassing angle unless it was actively in use. Kit put her shorts and trousers back on, letting it poke through the unbuttoned fly. She stroked it just once, pressing the flat base onto the fleshy area over her clit and stifled a whimper. Kit slid a questing finger through her fly, touching the wet and aching flesh that lay underneath. She couldn't touch her clit, as it was mostly obscured by the straps and rubber, but she slowly sank first one and then another finger into her cunt. Kit shuddered, but drew them out again reluctantly, washing her hands before doing up her pants.
When she returned, she saw that Helena had turned off all the lights except for the small reading lamp, which was on the far side of the room. Kit breathed a silent sigh of relief; that would make her necessary deception much easier.
"Welcome back," said Helena, when Kit had locked the door behind her. "I was getting ready to ring the coppers. Figured a couple of New York's finest could do me right if you weren't available."
Helena was kneeling on the bed, lazily mussing her hair and Kit could smell her perfume faintly, something rich and exotic, sandalwood, maybe.
"I... I'm very available," said Kit, and it seemed that Helena preferred enthusiasm to elegance because she opened her arms in mute demand and Kit all but stumbled onto the bed, making it creak alarmingly.
They kissed hungrily and clumsily, Kit lowering the straps of Helena's dress down around her arms to get at the tender curves of her collarbones. With an impatient hiss, Helena pushed her back just long enough to whip the constricting fabric over her head and throw it to the floor. Her hair sprayed everywhere and Kit finally gave in to the urge she had had all evening, burying her hands in it and roughly dragging Helena close to her.
"You crude little hick," giggled Helena, and then her eyes opened wide as she was pressed flush against Kit.
"My goodness," she said. "Is that all for me?"
Kit could only nod mutely. She pushed Helena onto her back, crouching above her and planting wet, sloppy kisses on her neck and chest. On impulse, she pressed her lips to the fabric of Helena's lacey bra and licked and sucked until she could feel the nipples rise up underneath the sheer fabric. They were shockingly dark, and Kit lifted Helena's full breasts out, sliding her fingers along the satiny skin.
"Not like that," murmured Helena. Kit drew back, alarmed that she had done something wrong, but Helena put her hand over Kit's and clenched hard, forcing Kit to squeeze her breast with nearly bruising strength.
"Doesn't that hurt?" asked Kit, wide-eyed.
"Yeah, and it feels really good too, baby," said Helena, sighing happily. "You want to make me feel good, right?"
Yes. There was only one guiding light in Kit's world just then and it was to make Helena feel good.
She squeezed again, not as hard as Helena had directed, but harder than she would have dared on her own, and was rewarded by a pleased murmur. She bent her head down and suckled gently on the other nipple as she squeezed and then, impulsively, she nipped at it. This time, Helena's moan was half-laugh as she gripped the pillow under her head.
"That's right, honey," she purred. "Give it to me like that.
Reassured, Kit kneaded Helena's body, glorying in her softness, her pliancy. Helena twisted gently underneath her, only pausing to tell her that it was all right, that she could certainly do that harder.
Helena didn't even try unbuttoning Kit's shirt, which left Kit feeling both relieved and disappointed. Of course Helena couldn't see the bandages that bound her chest, but Kit longed to have this gorgeous woman touch her everywhere, wanted it more than she wanted to breathe. She contented herself with stroking and tasting Helena's soft body.
Kit had to unsnap the garter belt to take off Helena's panties, but she couldn't stand to remove her stockings. The stark contrast between Helena's pale thighs and the stockings made Kit feel nearly dizzy. She traced skin above the stockings first with a gentle finger and then with an inquisitive tongue, which made Helena giggle when she got to the inner thigh.
"What a talented mouth you have, Kit," she cooed, "but don't you think it'd be more... useful elsewhere?"
Kit agreed and positioned herself between Helena's legs, spreading them wide with her hands. For a moment, she breathed in the spicy, musky smell of her lover before sliding the tip of her tongue along Helen's slit, from top to bottom. Then she parted the folds just a little more, repeating the motion, more deeply this time. Helena's appreciative moan told her she was doing something right, and on the third, slow pass, she just barely grazed the tip of Helena's clit, making her jump as though she had been electrocuted.
"You awful little beast," whimpered Helena, and Kit though she had never heard sweeter, sexier words than those.
Then Helena grabbed a fistful of Kit's hair, pulling her forward, and Kit found herself licking and sucking feverishly. She stabbed at Helena's clit with the tip of her tongue, and then laved it tenderly, making Helena's thighs tremble. Even as she did so, she pressed two fingers into Helena's dripping cunt, setting a steady rhythm that made Helena wail. She was tight and slick around Kit's fingers and all Kit wanted to do was slide the fingers of her other hand into her own aching cunt.
Just as Helena was nearly vibrating with pleasure, just as Kit was beginning to wonder if she was really as good as her old girlfriends had said, Helena pulled her back by her hair. Kit tried to shake her off and go back to what she was doing, but Helena slapped her lightly on the face. Kit looked up into the eyes of a woman who was nearly mad with desire.
"Fuck me now," Helena growled, every trace of her composure gone, and Kit was helpless to resist. She fumbled with her fly and as she did so, Helena turned around and got up on all fours, looking at Kit over her shoulder with marked impatience until Kit was positioned behind her.
For all of Helena's longing sounds, Kit had to pause for a moment to examine the sight before her. Helena's ass was beautifully rounded and Kit ran a gentle hand over the unmarked flesh before taking a small bite. Helena yelped and then growled, and something in her tone told Kit to stop fucking around and get down to business.
The rubber had warmed up from being between them, but to be sure, Kit ran the tip up and down Helena's slit, as she had used her tongue earlier, getting it wet and slippery. She eased the tip gently between the plump lips of Helena's cunt, watching the way the muscles tightened along her back and shoulders with fascination as she slid in. She was going to go slowly, tease her until she cried, but then Helena groaned low in her throat, a pleading, longing sound, and Kit couldn't have stopped if she wanted to.
She grabbed the curves of Helena's hips roughly enough to leave bruises, and started driving into her fast and hard. With every thrust, the cock was pushed back onto her clit, which was nearly painfully sensitive, making Kit wonder if she was going to soak through her shorts right to her pants
Helena moaned and whimpered, throwing her hips backward, trying to take as much in as she could, and Kit raked her back with her nails, leaving long red streaks.
"You fucking gorgeous slut," said Helena through gritted teeth, "Beautiful, fucking..."
Something about her words made some part of Kit nervous, but then she reached around and started toying with Helena's clit, rubbing that pretty little pearl until it was raw and Helena's cries turned into one long wail.
When Helena came, she somehow made Kit feel it, too. Even as Helena bucked and arched, the fake cock hit her clit in just the right way and Kit came as well, though she managed to stifle her yell somewhat and avoid making it sound too feminine. They both collapsed into a sweaty heap on their sides, their limbs shaking from the aftershocks of pleasure.
Kit knew that she should get up and take care of the cock, or at least pull it out of Helena, but it seemed that there were more important things to think about, like how warm and soft Helena was curled against her chest, and how her small, fluttery breaths ruffled the stands of hair that lay over her face. After a moment, Helena pulled away, but before Kit could even mutter a tired protest, she was curling up so that her head was under Kit's chin.
Kit didn't know how long they stayed like that, only that it felt wonderful It occurred to Kit again how beautiful Helena was, how soft and sexy she was. Kit dreamily decided that Helena could play with her breasts all night if she wanted to.
Kit stopped, going cold from head to toe.
Helena had unbuttoned her shirt and slyly loosened the bindings underneath until she had exposed a nipple and now she was simply toying with it, watching Kit's face with amusement.
"I..."
"You're a little fool who's playing an extraordinarily dangerous game," said Helena calmly. "You're lucky it was just me who caught you, and not some prissy society miss who would have hauled you in for perversion before she thought of her own reputation."
"I've done this before, okay?" said Kit, somewhat stung. "I know what I'm doing."
Helena snorted inelegantly and counted off on her fingers.
"You didn't put anything into your pants to convince me that you had a pecker before you got a raging hard-on. You didn't pull out before you came so that I would think you'd come on the sheets rather than inside me. You come like a girl. You didn't get up and take care of the dildo, you just lay there like a self-satisfied boy, which you are not." She arched an eyebrow. "Shall I go on?"
"It's never been important before. All the other girls..." Kit paused.
"Were idiots," said Helena briskly. "You can't rely on that, Kit, not when you're so goddamned clumsy."
"I suppose you want me out of here," said Kit, hating the petulant tone in her voice.
"Not at all," replied Helena. "You're cute and a terrific fuck, and with time and work, something could be made of you."
"Aw, thanks, loads," grumbled Kit, but it was hard to stay mad at Helena when she was smiling so sweetly.
"Come on," said Helena, stripping off Kit's shirt and bandages. "I want to see what my handsome girl looks like."
Hours later, they were sound asleep, naked and clinging, when a heavy pounding came on the door.
"You bitch, Helena, come on outta there, or I'm gonna break the door down!"
Kit nearly fell out of the bed, wide-eyed, but Helena only turned over, annoyed and clamped the pillow over her head.
"I know you got a man in there with you and I swear I am going to break every bone in his goddamn body!"
That would be my body, thought Kit numbly, shaking Helena's shoulder.
"Helena," she hissed, "Big Mike's at the door!"
Helena came awake instantly then, but the look on her face was not one that Kit expected. It was pure glee and Kit wondered nervously if being discovered in another woman's arms had driven her insane.
"Quick, put this on." whispered Helena, "and follow my lead."
She handed Kit a bundle of cloth that had been inside her large purse and sauntered to the door, naked as the day she was born. Kit only had time for one horrified look before shoving the garment over her head, which turned out to be a high-necked gingham nightgown.
"Helena you open this goddamn door-"
In the middle of his sentence, Helena threw open the door and Kit got her first look at Big Mike Powers, the hammering fist of the McReady gang.
He was younger than she had thought, with a round, nearly babyish face surrounded by a frizz of blond curls. He would have looked near-angelic if it weren't for his prize-fighter's nose, broken so many times that it seemed smashed flat, and the decidedly unholy rage that radiated from his six-foot two-inch frame. He towered over Helena like a thundercloud and Kit was certain he would crush her like a bug.
"Will you shut your mouth, Mike," said Helena, sounding only annoyed and sleepy. "There isn't any man here." She looked him up and down before saying, "Present company included."
Mike scowled and Kit fumbled for her boot, ready to throw it at his head should he lift a hand against Helena. The motion made drew Mike's notice her though and his brow furrowed even more.
"Here, now, what's this, a horgy?"
Helena rolled her eyes and stalked over, taking Kit by the arm and dragging her to the door.
"Does this look like someone who goes to orgies?" she demanded. Mike and Kit stared at each other for what seemed like a very long moment. Kit knew exactly what Mike saw: a confused, plain young woman with terribly tangled dark hair and skinny legs attached to huge feet.
"I guess not," he admitted.
"Thank you," said Helena, acid on her tongue. "Mike, I'd like you to meet my cousin Kit, from Sallisaw. She's having a bit of a rough time of it with her family and came up here. I'm to be keeping an eye on her, you see." There was just the right amount of annoyance and disdain in her voice that Kit winced and this seemed to convince Big Mike.
"Well, what're you doing wandering around buck naked, then?" Kit had to admit that she was wondering the same thing, and was glad that Big Mike had asked.
"Oh honestly!" said Helena. "I'm not going to change my ways for some little bible-thumper from the Ozarks, now am I!" She tossed a scathing glance at Kit. "She can damn well live with it, or she can pay for her own goddamn room."
"No call to be speaking to the poor kid like that," said Mike. "What a fucking mouth you've got on you!"
Kit, to her horror, found herself blushing madly, but this only made Mike nod decisively.
"There, see, you embarrassed her," he said to Helena.
"God protect me from idiots" said Helena, throwing up her hands. "I'm going to bed. If you two have gotten be such chums, then you can go out dancing for all I care."
"Just let me know where you're going next time, so I don't have tear this town apart looking for you," growled Mike, but he turned around and stalked off, muttering about over-educated broads and their high-handed ways.
He wasn't gone nearly long enough before Helena burst into a fit of giggles.
"Oh, that was brilliant" she laughed. "We had him so snowed he didn't even want to come in looking for men! Not that there were any to start with, of course...."
Kit waited for her heart to slow down to something resembling a normal pace before turning an aghast eye to Helena.
"You enjoyed that?" she gasped. "You're... you're insane!"
"Yeah, I guess I'm crazy," she said, smirking. "Cause I'm not the one who's running around in a pair of pants and trying to pass as a man. Yeah, crazy as a three-legged tomcat, that's me."
"Well, I..."
"Hey, don't worry about it," said Helena. She caught Kit's face between her hands and gave her a long, kiss that made Kit weak in the knees. "I'm also crazy about you, and that's the important part."
Originally published January 2006 - "Spanked!"