Pain & Pleasure
- This story was inspired by the following posts and the conversations therein: my own Ask Anything, Madeleine Mitchell’s On Women and Submission, and Thoughts on Submission by Lifeofalovergirl. I reveal, somewhat, how and why I write erotica. I like to explore and work out ideas in the telling of a story. I like to see if I can realistically capture certain behaviors and attitudes that we all share. It helps me work through ideas on sex, sexuality, and my favorite love and subject, women. If you’ve read these other posts, let me know what you think of the story; if it captures some of what we discussed; and if it’s at all true to your own experiences. Don’t know if there’s any depth to it.
—Thanks for the drink.
—My pleasure, he answered.
She was on a bar stool wearing a black, sequined, one-piece dress, zippered along her spine. She was leaning forward, one elbow on the bar, danging a paper umbrella over a Whiskey sour. When she leaned, her black dress followed the inward curve of her spine from her shoulders to the small of her back. Men were looking at her, some by themselves, some with wives. She knew what they were thinking. The curve of a woman’s spine is the curve of fucking. The dress stretched, filled and glittering, around her hips and ass, then ended midway to her bare knees. She didn’t wear underwear. She wore nothing but the dress.
He sat, or rather, leaned on the bar stool next to her, facing the opposite direction. He wore a black suit, black shirt, top button buttoned, and no tie. He was bald, middle-aged, wiry, medium hight, but muscular. His cheeks were sallow, one being scarred, and his eyes were steady.
—Finish it, he said.
She sipped from the whiskey sour.
—Look, she said, I’ve got a meeting tomorrow. I’ve got over a hundred employees–
—I’ve got to be in Rome tomorr–
He had moved behind her. For now, nobody, could see what he did in the dark lounge. He’d yanked her ass back off the edge of the barstool, a quick, decisive yank. She stopped talking. He pinched the fabric to either side of the zipper and yanked. The little stretch of zipper over her anus parted, and so did her anus. She stared, blankly as his finger, rough and calloused, pressed upward and into her.
—Shut up and finish it.
He jammed his knuckles up hard, his finger deep. If there was anything to see, it was just his fist hard against her ass, at t he center of her broad underside, pressing her from behind. Her fingers shook when she lifted the Whiskey sour to her lips and drank. She finished it. He didn’t remove his finger from her ass. He left it there when he threw a fifty on the counter, when he told the barmaid, a smaller and younger women, to keep the change.
—Are you okay, hon? the barmaid asked.
—Answer her, he said, his finger curling insider her.
—Yes, she stiffened..
—What’s your name? he asked the barmaid.
—You seem like a nice gal.
—You care. You notice that about people. I like that. What’s that tattoo on your wrist?
—For a boyfriend?
— Sort of. His name’s Edgar Allen Poe. Anything else I can help you with?
—Yeah. Room service.
—No, will you, as in you, bring me and my lady a gin and tonic in about 20 minutes? Room 632.
He unfolded five one-hundreds, with one hand, and smoothed them on the counter. The girl cautiously looked around her. The diamond piercing in her nose glittered.
—Hotel staff aren’t–
—And another five hundred when you deliver, he interrupted.
She hesitated, slipping her tongue under her top lip, then slowly slipped the bills off the counter top. She glanced at the older woman, took the empty glass.
—Okay. Twenty minutes.
She turned, eying the couple as she did so, then half-backed thorough a door to the rear and side of the bar,
—Get off the stool.
Jennine stood, slowly, gingerly, his finger still in her ass.
—Do I need to keep this finger in your ass?
She leaned forward, elbows on the bar top.
—Stand up straight.
—And straighten your fucking dress.
She pulled it tightly down by the hems, awkwardly rolling her hips left, then right. He slowly removed his finger and she shuddered, exhaling softly.
—Guess there’s a little a hole in your dress. Better not bend over.
He pressed at the small of her back, an impatient gesture. She moved out of the lounge’s darkness, through the company of other guests talking and having dinner, and into the lobby. There were always men who looked at a woman’s ass. She pinched her lips as she moved from the restaurant, into the lobby and to the elevators.
—You like men looking at your ass?
—That’s why you like it.
She didn’t answer, instead she turned, she liked his chin, she kissed him.
—That’s what I get for a thousand?
—No, whatever you want me to call you, whatever you want me to do – Sir, Master, Owner.
—Whatever I want?
A younger couple, early twenties and smelling of hard liquor, joined them as they waited. The elevator bell rang and both couples stepped into the elevator.
—What if I want to fuck you right here?
—I don’t think this is the place–
His finger found the zipper’s hole. She flinched.
—Are you saying ‘No’ to me?
He found her anus. Her knees came together. She inhaled, hands panicked for balance, then flying to the hem of her skirt, pushing it down as her abdomen swiveled back. She looked away from the couple. The younger man had backed against the wall and his girlfriend had backed against him. He tugged at the younger woman’s nipple through the purple fabric of her top.
—Want to tell them what’s wrong? asked Devin.
—His finger is up my ass.
—Look at them and say that.
She grunted, bending forward as his finger more forcefully lifted her ass.
—His finger is up my ass and he’s fucking me with it, right now.
She said it quick, matter-of-factly, words struggling. The girl cagily met Jennine’s gaze. She pressed her ass against her boyfriends pelvis. The palm of her hand brushed his crotch, began to search for his zipper, but the elevator’s stop interrupted them. The girl wanted to see more, but she was guided out of the elevator by her boyfriend, his hands on her shoulders. She glanced backward with an impish smirk as the elevator closed again.
—Fifth floor, he said, matter-of-factly.
—Didn’t I hear you say ‘No’ to me? That’s an issue and we’ve got some time to kill.
She pressed 5. When the elevator stopped he pushed her out, finger still in her ass. They rounded a corner. There was ice and Coke machine, and then the door to the stairs. He stopped her at the ice machine.
—Bend over. Put her hands against the ice machine.
She did as she was told. He shoved his fist into the ice machine, letting it grind out a handful of crescent shaped ice-cubes.
She watched him with a bemused grin.
—You’re going to need it to cool your ass when I’m done with it. Spread your legs.
He put two of the ice cubes in his mouth, spit them out, then pressed the tip of the first one through the hole at the back of her dress and against her anus. She inhaled sharply. Her fingers spread, straight and fingertips lifted. The first ice cube parted, then slipped into her, drawn inside by her own muscles. She gasped, a high pitched intake of shook, and her spine bent as her hips swiveled. He pressed the next, and then the next into her ass, her clenching muscles betraying her each time, sucking the ice cubes into her bowels.
She pressed both palms against the base of her abdomen.
—You’ve got a choice. We can go back to the bar. Maybe we’ll find another couple. We’ll strike up a conversation and all that ice can melt in your ass. The ice Queen thaws. You can try not to squirm in your seat, fidget, bite your lip like a little girl. You can clench as all that ice turns to ice-water. Maybe I’ll diddle your clit under the table. You can try to hide it all. Maybe you won’t be able to. Maybe you’ll have to slide your ass back over the edge of the chair as all that ice-water spurts out of your ass. Then again, we can go up the stairs. How don’t know how many there are, but you’re going to stop on each one, bend over, hands behind your neck, and I’m going to smack your ass god-damn ass hard for saying ‘no’ to me. You can squat right now and push out all those ice-cubes. Then again they might come out one by one, stair by stair. What’s your choice?
Jennine made her choice. She pressed herself against him, breasts against his chest, one hand drawing his lips to hers, the other pulling him against her midriff. They kissed. She fumbled for the fly of his pants. She wanted to suck him, to taste him, to worship him. but he stopped her with a knowing smile that creasing the corner’s of his eyes.
—Make me suck your cock, she whispered. Come in my mouth.
—Oh, no you don’t.
He brusquely turned her round, opened the stairway door with one hand and pushed her through with the other. She heard the slide of his leather belt through linen belt loops.
—First step, he said. That’s it. Now bend over.
The first crack of the belt echoed in the steel stairway. So did her cry. She took another step. She braced her hands against the worn steel edge of the stair above and cried out again. When she reached the last step before the landing, midway between the two floors, her cheeks and lips were stained with moisture, as were her thighs. The belt stung again. She pressed her knees together. She spread them. She lifted her ass. She clenched her thighs. She crawled on hands and knees to the landing. They heard a door open at the bottom of the stairs.
She stopped midway along the landing. She curled her spine, lifted her ass, spread her knees as far as the hem of the dress would allow. She spread her hands, palms down on the concrete and peered behind her. Anything. She would do anything to stop the discipline. She would do anything to relieve the icy ache in her gut. Warmth. A cock. Anything.
He knelt behind her. The whole made by pulling the zipper apart had lengthened during her struggles. Her anus and the top of her pussy, red and parted, were visible through the lengthening hole. He entered her with a single thrust that made her sharply cry again. The filling heat of his cock felt all the warmer penetrating the iciness of her abdomen. He thrust hard. She reached forward, bracing, drawing one knee forward and under her. The fucking didn’t stop. He yanked her knee back. He pushed her head down, hand between her shoulder blades. He yanked her cunt against the blunt punching inside her. She was going to come, but he came first. He held her, fingers in her hair, her wrists crossed behind her back in his other hand, forcing her hard against his pelvis. He didn’t move, only his cock, smoothly pumping his orgasm inside her. A final last, spit of semen seized him before he fell over her back. He breathed. She turned, just her lips, and they kissed.
—Don’t move, he whispered.
Another door opened and closed beneath them. He straightened. He withdrew his cock slowly, enjoying the wet and glistening smear of her cunt. When his head popped out, semen gushed, dribbling down the back of her skirt.
—I’m not done with you.
He stood and so did she. He didn’t see her flickering smile as he told her to go up the rest of the stairs. He slid his belt back through his pants. He zipped up his fly and followed her swaying hips, the curving black sequined dress, up the stairs. Cum. his semen, dripped and streaked the back of her dress from the hole to the bottom hem. She’d been fucked from behind and her hips moved with the loquaciousness of the fucked. When they stepped into the sixth floor hallway, and when there was another older couple that stepped out of the elevator, he didn’t hide the rear of her dress.
He let them see that she’d been fucked.
The elder couple passed them by. The woman glanced at Jennine, then sized up Devine. Her husband cupped her ass. A matter-of-fact push at the small of her back guided Jennine into Room 632. He made sure the door didn’t shut behind them, but only almost. Then he yanked the covers off queen bed, leaving only the bottom sheet.
—On the bed. On all fours.
—Do you want me to take my dress off.
—The dress makes you more vulnerable.
She put one knee onto the bottom of the mattress, then climbed onto the bed. She waited on all fours, in the middle, as her lover pulled out his cock and slowly stroked it.
—I’m going to fuck you again.
—You know you’re a cunt,
—You know your cunt is dripping down the back of your dress.
—I can’t stop it.
—Have you thawed.
—I can make that better.
He stepped next to her. He reached under her neck, at her collar bone, and forcefully yanked her dress down, tearing it, freeing her tits.
—This was an expensive dress.
—Did your husband by it?
—Then it wasn’t expensive.
—So what am I supposed to wear?
He yanked her head up and back by the hair.
—Look in the mirror over the desk. Can you see yourself?
—Good, keep looking.
He left her for a bag at the bottom of the bed. He unzipped it. He pulled out a red dildo, large, shaped like a large cock with a dolphin. He could hear the trembling in her breath as he moved behind her.
—It’s too big!
—Look in the mirror. Watch.
—I won’t fit! It’s too big!
—Arch you back! Keep it arched! Show me your pussy.
He smacked her ass hard. She lifted it. He reached forward, slapped her face.
—Yes! Yes, Sir! I’m looking!
He slapped her face again, not a swinging slap, not a hard slap, but a stinging one.
—Is the cunt watching?
—Your cunt is watching. Your cunt, Sir, she half screamed.
—Is she beautiful?
She paused for moment, swallowing.
—Yes, the cunt is beautiful.
He slapped her again. Water spurted from her ass and she she squealed with surprise, quickly pulling her knees together, biting her lips, then spreading them again. She tightly lifted her ass, her back a U of supplication. He place the giant spaded head of the dildo at the small of her back, hanging it straight down from his fingers, then let the broad tip slide back, over her anus, until the head fell into the nook of her pussy, resting there, too large to slip inside.
—Do you see it?
He pushed, straight down, forcing the lips of her pussy to part and swallow the head of the dildo. She stiffened. Her fingers tightly gripped the sheets. She watched in the mirror as the red thing slowly began to sink into her. He pulled it back up. The stretched lips of her pussy widened over the flange, then quickly closed, sliding together until they kissed the tip of the red cock. She was panting.
But she didn’t answer. He pushed downward again and this time she moaned aloud.
—Do you see it?
—Yes, she answered, her voice stretched around the width of the cock.
—Where is it going?
With a twist of the end, the dildo began to vibrate. He pushed and she give a high-pitched, feminine yelp. He didn’t stop this time. She mewled. Her heels rose up behind her, toes straight as the thing continued to slide into. She gave a guttural cry and reared back, then collapsed, head down, onto the mattress as the cock bottomed out and the dolphin pressed against her clit.
—Not too big, is it.
—Oh fuck, her fingers twisted in the sheets. Oh fuck.
—Stay like that.
—Now I’m just going to watch.
He pushed just slightly at the butt of the dildo distending the skirt that trapped it. She stiffened and inhaled. He let go and watched it stretch the fabric. He saw it twitch. He imagined it inside her, the way women are made, the broad tip deeply in her abdomen and and he squeezed his own hardening cock. A traced the curve of her spine. He ran has palms over her still youthful calves. He stood. He felt her ribcage, her breathing, then cupped her breasts. He squeezed and pinched her nipples until her ass lifted and her hips swiveled behind her.
They heard a knock at the door.
The barmaid held a tray – two gin & tonics with a slice of lime. She was small. Her straight, dark brown was feathered at her shoulders. Her eyes were dark brown.
—Bring it in.
She stepped into the room and stopped.
—I’m really not sure I’m comfortable with this.
—Did you think I paid you a thousand dollars for a gin and tonic?
—You paid me five hundred.
—And the other five’s on the table. You want it? Give me fifteen minutes of your time and you can have it.
—I don’t swing.
—You don’t have to.
The girl studied the woman on all fours. Her gaze was curious and a game smile briefly played her lips.
—I’ve seen a lot. This is different.
—Have you ever seen another woman come?
Many stared. Jennine returned her gaze. The butt end of the dildo twitched and the older womans blinked. She lowered herself to her elbows.
—Keep your back arched. Didn’t I say to keep your back arched?
—Only in pornos, answered the girl.
—What are doing working as a barmaid?
—Paying for school.
—You watch pornos in your free time?
—What do you watch?
—I watch guys fucking girls.
—You like to watch?
—You like it when a guy spanks a girl?
The younger woman studied Devin, considering.
—Whose that other gin and tonic for?
She reached for the glass, drew the slice of lime around the rim, and drank.
—Yeah, I do, she said.
Devin stood, he walked to the side of the Queen bed and unzipped. He pulled out his cock and began stroke. He slid a finger’s tip along Jennine’s spine.
—Pain and pleasure. I guess I know what it feels like. Men don’t get it. For men, food, drink, sex, life, it’s all about pleasure – avoiding pain; but women… Women aren’t so lucky. God condemned Eve to suffer, right? Life is pain and pleasure. You learn there’s never one without the other, and you start forgetting which is which. Love and hurt. Hope and heartbreak. At first, you tell yourself you deserve some pleasure after so much pain, but then you get confused. You start telling yourself you deserve pain too, after the pleasure. The more pleasure, the more pain because you don’t deserve it any other way. If you’re feeling good, somebody else is hurting. It’s the way women are made. Seeing another woman, when she’s coming, when she can’t tell it’s because of pain or pleasure, I guess I know what it feels like. I want to tell her its okay. I want her to tell me it’s okay. I want her to see her come. Maybe I want her to see me come.
—Do you want me to spank her?
The younger woman was quiet. She licked her lips and took another sip of gin before putting back on the tray.
—I’ve got half an hour.
—Do you want me to spank her?
She spoke again, quietly, almost a whisper.
Jennine gasped with the first smack. He waited. He smacked her again. She tightly gripped the sheet, turning her gaze downward.
—No. Look up, he said, quick and flatly.
She did. He smacked her again. The younger woman expression changed. Her hand reached under her blouse, finding her nipple; another unbuttoned her jeans. She opened her legs. She slipped her hand beneath the seam and exhaled.
This time she shouted each time she was smacked, maybe it was because she had an audience, maybe, like the girl said, there was somebody taking pleasure in her pain. The older woman opened her knees, twisted, and caught the girl’s stare. She pulled at the edge of the mattress with each smack. She see-sawed her hips though impaled by the monstrous cock.
—Pinch her nipples, said the girl. No. Wait. Do you have nipple clamps?
—Put them on her.
The younger hurriedly released two safety-pins from the back of her blouse. The older woman panted and groaned as the nipple clamps were attached. The safety-pins forced her nipples almost to the bed sheet. The girl stepped back and shimmied out of her jeans, then pushed down her panties. She backed against the desk chair. She sat, opened her legs and stroked her pussy.
—It turns me on.
—Why, asked Devin.
—I don’t know. Good fucking is like good literature. It’s archetypal. I mean, what the fuck’s more symbolic, more female than this? I mean, it’s our tits, right? We can’t hide them. Tits. They’re like advertisements. Fuck us, inseminate us, put a baby in us. Check out our tits. All you have do is put a cock in our cunt and you’ve got us.
Her eyes fluttered and her back snapped with a first spasm.
—Look at her, trapped by her tips, held by her tits, her cunt in the air behind her. I mean, how fucking symbolic is that? Fuck her like that.
—There’s a dildo in her cunt.
The younger woman gradually smiled.
—Why me? I mean, you’re at a fucking swinger’s convention, and you don’t swing.
—By why me?
—You care. People who do this year in, year out, they stop caring. They know how the play goes. They stop paying attention. You? You want to see it all. You don’t want to miss anything. That’s worth a thousand dollars.
The older woman abruptly grunted and her eyes blinked with confusion. Her spine stiffened and water spurted down her thighs. The butt-end of the dildo twitched rhythmically. The girl quickly knelt at the foot of the bed. She grabbed the older woman’s hair by the back of the head and kissed her, furiously rubbing her own cunt.
—Make her cum again, she gasped. I wasn’t ready.
—Did I give you permission?
—No! cried his lover. No, Sir! I–
She inhaled, almost swooning. Her abdomen gripped the embedded dildo once more.
—It’s so deep1 I can’t help it. It’s just– when it’s there like that. I can’t help it.
—Of course you can’t, said the girl.
The older woman’s eyes widened with shock when she instinctively rose up, spanked again, only to have the sheets painfully stretch and tug at her nipples. She lowered her chin and raised her ass. She abruptly widened her knees.
—Take the dildo out of her cunt and put it in her mouth.
—I just want to see her fucked like that. I don’t know– One cock in her mouth, gonna’ spurt come down her throat, another cock in her cunt, gonna’ spurt from below. She needs to know her place. She needs come filling her from both directions. Has she ever had come in her cunt?
The girl smiled.
—She’s just a naïve girl, isn’t she?
He unzipped the dress and slowly pulled out the bright red cock. It gleamed with moisture. More and more and more of its length appeared until finally, her cunt widened around the spaded tip, and a web of her own orgasm dripped onto her back. He yanked her head back. She closed her lips tightly. She shook her head. He smacked her ass. She squealed, lips tight. Her tits stretched against the clamps and her brow creased with pain, or pleasure, or both. Then she reached behind her, to stop what was already widening the lips of her pussy.
But too late.
A single hard thrust pushed her forward, lifted her toes off the bed, distended her nipples, opened and straightened her fingers. He crossed her wrists at the small of her back.
—That’s it, said the girl. Fuck her, The girl needs come.
—Hold the tip of the dildo, right there, right against her lips, said the older woman’s lover.
He thrust hard, not quick, but deep and firm.
—Let her smell it, he said. Let her taste. Let her get used to it. Every girl has to be broken the first time.
—Go ahead, said the girl.
She pressed the broad, mushroomed, tip of the red dildo against the older woman’s tight lips.
—We’re born to be ruled. It’s biology. We’re born to take cock.
The fucking went on, maybe 5 minutes, maybe 7, and the older woman’s eyes began to roll, lose focus, roll again. Her tongue parted her lips and kissed and tongued the end of the dildo.
—That’s it, said the girl. Kiss it, Taste it. That’s it. In it goes. Why do you think those lips are so pretty?
The woman’s eyes widened, her lips parted, and the swollen bulb of the tip entered her mouth, pressed her tongue beneath it, and slowly moved against back of her throat. The other cock pressed at her womb for behind and it felt as if the tips of each might almost meet in the middle, as if this is what it meant to be a woman.
—She’s gonna’ come. Hold her tight. Hold her hips so it hurts. Bruise her. Make her jerk her tits.
The girl furiously stroked her clit, on her knees, back arched, thighs spread.
—Fuck! Make her orgasm hurt. That’s it sweet girl, she cooed, her voice changed, shaking the movement of her arm and fingers. Go head. It hurts doesn’t it. Come. Welcome to womanhood, sweet girl.
The older woman grunted, her abdomen contracted and she swooned. She exhaled, nostrils flared, her lips stretched around the base of the cock.
—Oh God yes, sighed the girl. Quick. Come in her. Now! When she’s confused; when she doesn’t know what’s happening; when it hurts so much and feels so good, put your semen in her. When she’s confused. Load her cunt.
The girl was coming. She pulled the dildo out of the other woman’s mouth.
—Fuck, you’re beautiful. You’re so fucking beautiful.
The women kissed, mouths open, lips pressed tightly to lips. The woman’s lover leaned back, hips thrust forward. All three shook. The man growled, the tug of each spurt drawing him more deeply into his lover – male, instinctive, animal, uncontrollable.
They fell their separate ways.
After three, maybe four minutes of silence. The girl came to the woman, unhooked the nipples clamps, kissed her neck and spine when she stiffened and gripped the bedsheets in pain. She touched the bruises on the woman’s hips. She kissed them.
—You’re lucky, said the girl quietly. I want to be fucked like you someday. I want to belong to somebody, sometimes like an ache; sometimes ashamed of it. I want to be owned. I want him to fuck me like he fucked you. I want him to be crazy in love with me, and if he is, I’ll let him fuck me just like you. I’ll let him hurt me. I’ll let him mark me ’cause that kind of love is better than tattoos because they go away. Men have to mark you again, and again just to make sure you don’t forget who you belong to.
She smiled. The older woman rolled over embraced the girl, smiling in return, brushing the younger woman’s hair out of her face.
—Thank you, she said to the girl.
The girl rose from the bed. She put on her clothes, took the other five hundred, and left with a glance, a bite of the lip, a reluctant smile.
Categories: Algolagnia, Anal, Consensual, Copulation, CP, Cum, Dominance & Submission, Erotica, Exhibitionist, Foreplay, Insemination, Married Sex, Masturbation, Oral Sex, Paid Sex, Public Sex, Quickie, RedBud, Reluctance, Rough Sex, Sex Toy, Spanking, Threesome, Voyeur