Roleplay Gone Wrong

by Reed James

“I want you to be my john.”

  “Your what, babe?”

  “My john,” she continued; breath moist on his ear. “You know, the guy who picks up a prostitute.”

  “Right,” he muttered. “I should have realized that.”

  “Having a little trouble thinking?”

  “Well,” he smiled, “it's hard to think with a beautiful, passionate, amazing woman stroking your cock.”

  Her laugh was throaty and wicked. “It must be so hard to be a man and have all that blood pooling in your cock, starving your brain of oxygen.”

  “It definitely has its advantages,” he answered.

  “Umm, I can feel all seven inches of your advantages.”

  “Eight inches,” he protested. “Just like you've been twenty-nine the last six years.”

  She kissed him, her lips salty. “Fine, eight inches. And where would you like to stick this impressive specimen.”

  His hands wormed between her wet thighs and he roughly shoved two fingers deep into her. “I think this'll do just fine.”

  She threw her head back and laughed, rich and velvety. “I think it will.”

  She looks like a goddess, he thought as she straddled his waist. Frank's cock reached for the sky, for the pussy hovering just inches above it. She lowered slowly until his tip brushed her petals, teasing him. Her fingers grabbed his cock and rubbed him across her engorged labia, smearing precum and pussy cream together.

  “You haven't heard the best part of my idea,” she purred.

  “What?” he demanded, frustration tinging his voice. “Can't this wait!” He wanted to be buried inside her. No, he needed to be buried inside her. His cock ached for her embrace.

  “I want to stand on a street corner, out in public, dressed like the trashiest whore. Then you get to drive up and pay me. There's this motel we can go behind and fuck like bunnies in your car.”

  That sounded dangerous, but it was so hard to think with her silky pussy rubbing on his dick. His cock needed to be inside her. He would agree to anything at that moment to feel her sheath engulf him. “Fine. Let's do it!”

  Whatever reservations he may have felt were driven away by the rapture of her pussy engulfing his cock. Warm, wet, spongy. It was absolute heaven. Nature had left her barren and she was as tight as she had been at twenty.

  “Fuck!” he groaned as she rose up achingly slow, the sweetest friction rubbing on his sensitive tip. “Take off the nighty! Let me see those beautiful tits!”

  Evie peeled the negligee over her head, revealing her magnificent, round breasts. Her nipples were fat, pink, and centered in half-dollar sized areolas. At thirty-five, or twenty-nine, or whatever age she claimed to be, they were still perfect. His hands roughly grasped them; his ardor was too great to consider being gentle.

  “I'm going to be your five dollar hooker!” she gasped as she bounced on him, her tits jiggling. “A cheap whore to be used for your pleasure!”

  “Oh Evie,” he moaned. “Be my whore!”

  “Yes, yes, yes!” she panted over and over. “I will! I'll be your dirty, filthy hooker. I'll do anything you pay for! Anything!”

  He couldn't believe it; his balls were already boiling over. It was like he was back in college all over again and able to go three times in a night. He grunted as he erupted his frothy passion into her churning sheath. Evie slammed down and ground her clit into the wet, tangled mess of his pubic hair. She bucked, her pussy convulsing about his cock as her orgasm smashed through her.

  “Holy shit,” he muttered as she leaned down, her heavy breasts rubbing against his hairy chest. “You are a helluva woman. I'm glad I married you.”

  Smiling, she breathed, “You ain't half bad either, Frank.” Her kiss was sweet, loving, as they both came down from their orgasms.

  As Evie fell asleep on his chest, Frank's mind was full of thoughts of the fun they'd have on Friday night. He just had to get through the drudgery of the next two work days.

  Chapter Two: Working the Street

  The last two days had been hell for Frank.

  Friday night had finally arrived and he waited eagerly to see her dressed in her hooker attire. He was excited for tonight and the game Evie wanted to play. It would be the wildest thing either of them had ever done, and his cock had been hard all day thinking about it.

  For the last forty-five minutes she had been busy in the bathroom, doing the hundreds of things a woman needed to do before she was 'presentable'. Frank was ready in five minutes. He peeled off his work clothes, spritzed on a cologne Evie bought him last Christmas, and pulled on some causal clothes: jeans and a T-shirt. Then he tried to watch the six o'clock news, but he was too excited to pay attention.

  He wolf whistled when she stepped out of the bathroom, his mouth salivating at the sight of her.

  She was absolutely stunning in a black bustier that cupped her generous breasts, transforming them into round, succulent orbs. The bustier was so low-cut the merest pink of her areolas peaked out the top, sending an erotic thrill through him as he drank in her beauty. Her flat stomach was left bare by the top, and the waistband of a black thong peaked out above her low-riding, and very short, tartan skirt. Thigh-high, fishnet stockings, like a black spiderweb, covered her sleek legs, and stiletto heels added a couple of inches of height and a very sexy sway to her hips when she walked. She went heavy on the makeup, tarting herself up with heavy eyeliner; a vibrant, blue-gray eye shadow; and deep-red, shiny lipstick. Dangling from her ears were large, trashy, gold hoop earrings Frank had never seen her wear before—she preferred studs as he learned the hard way while they were dating.

  “Damn Evie, you are gorgeous,” he groaned. “And those legs just won't quit.” The frustration of the last two days was worth it to see his wife in her hooker getup. “We are going to have so much fun tonight, babe,” he grinned.

  “You bet your sweet ass we are!” Evie fired back, positively skipping as they headed out the door.

  Tonight would be the riskiest – and the most exciting – roleplay they had ever done.

  They went in separate cars. Evie in her cute, red Audi and Frank in a silver Lexus. He could tell how excited she was as he struggled to keep up with her. She always had a leadfoot, even when she wasn't in a hurry. But when she was excited, she was like a NASCAR driver, weaving in and out of traffic like she was racing the Datoyna 500. She never received tickets though; Frank figured she was so pretty the cops must let her off with a warning. He lost her on I-5 about halfway there, but he knew around which block of International Boulevard in SeaTac she would be at.

  The sun was setting behind Frank when he reached the stretch of Highway 99 known as International Boulevard, and looked for his wife. Heavy traffic rolled both ways on the five lane road. It was a few miles from the airport and full of seedy motels with names like: the 'Cheap N Easy Motel', 'The Truck Stop', and the 'Beaver Inn'. They all advertised 'affordable rates' and discounts for 'short stays'.

  Scantly clad women lounged on the street corners, calling out to passing cars. They were a mix of the surprisingly attractive to the downright skanky. Frank scanned for his wife or her car as he slowly drove up the street. Where was she? Panic churned his stomach, like a blender making one of those disgusting vegetable juice drinks Evie consumed for breakfast.

  Then he saw her at a corner all by herself, waving at the streaming cars like a common whore. She looked even sexier on the street – in her black bustier, thigh-high fishnet stockings, and tartan skirt – than she had at the house. Before she had merely been a sexy woman in her home, but here, on the busy street, she was a hooker – a common whore – looking to debase herself for a stranger's pleasure.

  Frank's cock was a telephone pole in his pants.

  She blew kisses at the cars, and shook her tits, barely contained in her bustier and liable to pop out for all of SeaTac to see. She'd flip up her skirt, shaking her ass and letting the cars get a good look at the piece of floss she called a thong that disappeared between her supple b
utt-cheeks. Then she would stretch out her stockinged legs for the admiration of all the passing men, sensuously stroking her lithe thighs.

  Frank could hear the cars honking their appreciation.

  Other men are lusting after my wife, but she's all mine, he thought, a smile crawling across his broad face. He had to adjust his rock-hard dick so it didn't rub against the metal zipper so painfully. He decided on going commando tonight; ready to fuck his hooker-wife.

  He pulled up slowly, rolling down the passenger window. She smiled, leaning in, popping a big piece of pink gum. “You lookin' for a good time, sugar?” she purred. Her voice had a sultry, yet bored, tone to it, nothing at all like her normally warm dulcets.

  “I sure am,” Frank answered. “How much for a date.”

  “Twenty for a BJ,” she purred, popping her gum again. The minty scent tingled in his nostrils.

  “How much to let me do whatever I want?”

  She leered, eying his crotch. “A hundred and fifty and you can use me in whatever, nasty ways you can think of, sugar.”

  “Deal,” he answered. “Get in.”

  “Uh-uh, you pay up front, sugar.”

  Frank pulled out his wallet. He had two hundred in cash in there. He hadn't been sure how much his wife was going to charge, and wanted to be ready. He counted out $160. “You got change?”

  “ 'Fraid not, sugar. Think of it as a tip.” Evie popped her gum, leaning deeper into the car so he could get a good look down her cleavage. Her breasts strained to against the bustier, wanting to spill free. “Don't worry, you'll get your money's worth.”

  He took the money, wading it up, and shoved his hand into her bustier and gave her tit a nice squeeze, leaving the twenties behind. She stood up, pulling the money out, and quickly counted it. What a nice touch, he thought. Smiling, she slipped it back into her bustier and opened the door, sliding in. His hand instantly went to her thigh, dipping beneath her skirt.

  “Go around this motel,” she pointed. “There's a nice alley that's very private.”

  “Why don't you start sucking my cock, whore?”

  Grinning, she spat out her gum and stuck it into his ash tray, then she stroked his hard bulge as he eased back into traffic. His zipper came down with a metallic rasp and his cock popped out like a pink snake leaving its hole. He almost missed the turn as her magnificent mouth engulfed his cock, her tongue rapidly twirling about the tip as she sucked.

  “Christ, you're good, whore,” he moaned.

  He turned into the ally. It was dirty, trash lining the corners, blown in by the wind. Six or seven large, green dumpsters, their exterior paint chipped and the exposed metal rusting away, lined a high, wooden fence on the left and on the right was the brown, peeling facade of the Beaver Motel. He parked between a pair of dumpsters, using them to shield his car from the street.

  She sucked harder, slowly working her mouth up and down on his cock. He reclined back in his chair, groaning as pleasure surged inside him. Adrenaline pumped through his blood, heightening the pleasure. The thrill of his wife pretending to be his cheap whore and the risk that they could get caught at any moment, added a spice to her blowjob that was quickly bringing his balls to a boil. He didn't want too cum so soon, but he couldn't help it.

  It was all so exciting.

  The load rap on the window caused Frank to jump and Evie to bolt upright.

  Fear chilled his body like an icy breeze, and his cock wilted like a thirsty plant beneath the desert sun. Standing at the passenger door was a police officer peering into the window. A big man, ebony skin, his face stern as a statute. Mirrored sunglasses hid his eyes, making him seem even more intimidating; an implacable, unfeeling, law enforcement machine.

  “Step out of the car, miss,” he ordered sternly.

  Flushing, Evie gave him a worried glance, then opened the passenger door and slid out as he quickly tried to put his cock away. The cop eyed her up from head to toe as she stood before him. Was that a smile playing on his lips? He looked again, and the cop's face was still stern, implacable. Must have been my imagination.

  He put his dick away and opened the car door.

  “Sir!” barked the cop. “Stay in the car!”

  Frank froze beneath the power of the cop's tone, demanding his complete compliance and hinting at dire consequences if he didn't obey.

  “Uh, yes officer,” Frank answered. “This is just a misunderstanding.”

  “What part about catching a woman sucking your dick did I misunderstand?” the cop asked. “Was she performing first aid on you. A little mouth-to-cock resuscitation?” He laughed like he just said the funniest joke in the world.

  “It's not what it looked like,” Frank continued.

  “Really? You're not a john paying some piece of trash hooker to blow you in an alley?”

  “I am his wife,” Evie piped in. “We were just having some harmless fun.”

  The cop laughed. “Well that's a first. I've never heard a hooker try that lie before. Hands against the car, cupcake.”

  “I'm not a hooker,” his wife protested as she placed her hands on the hood, her short, tartan skirt rising up her sleek thighs as she bent over. “Please, mister...”

  “Connoly,” he answered. “Officer Connoly.”

  “I'm Evie Reynolds, and that's my husband, Frank Reynolds. I'm not a prostitute!”

  The cop frisked Frank's wife; his large, dark hands roaming over her body as she trembled, bracing herself against the silver Lexus. “If you're not a prostitute, cupcake, then why did I see you standing on the corner showing your very ample body to passing cars. Then you accepted money from this man, and when I followed the two of you, I caught you sucking his dick. Seems pretty cut and dry to me.”

  The cop's hand suddenly shoved into her bustier and shock spread on his wife's lips, then Frank heard her sigh, a throaty sound he's heard many times in their bedroom. No. I must have heard her wrong. That must have been an indignant sigh. Anger boiled inside Frank. How dare he grope my wife while pretending to search her!

  “You keep your hands to yourself,” Frank yelled. “I'll report you for sexual harassment!”

  “Frank, don't make things...” her words were cut off by a sharp, cooing sound that issued from her throat, while delight lit up her eyes as the cop continued groping his wife. “Don't make things worse!”

  The cop's hands came out with the wad of twenties. “This say's you're a hooker, cupcake.”

  He shoved his hand down her other bustier, groping her breast as he searched her. A sick feeling bubbled in Frank's stomach. “Hey!” he objected, opening his car door. “That is going way too fucking far!”

  “You try to get out of the car one more time, sir, and I'll arrest you, too,” Officer Connolly threatened coldly, his hand still groping her tit. “And it won't be for solicitation. Now I got to search her for any drugs, weapons, or other contraband. So let me do my job, buddy!”

  He swallowed, What should I do? Fear clutched at him. He didn't want to get arrested, but the way the cop was treating his wife made his blood run cold. Fuck it! This guy's going too far. He didn't care about getting arrested; his wife needed him.

  “Hmm, you're pretty good at that!” Evie moaned. Frank was shocked to hear the lust in his wife's voice, and his arm froze as he reached for the door handle.

  “You like the feel of my hand, whore?” the cop chuckled, pulling it out along with her breast. Her pink nipple was hard and she wiggled her hips. To Frank, it looked like she was pressing her ass back into the cop's crotch.

  Evie's favorite roleplay was the hooker fucking the cop to keep from being arrested. The sick feeling in his belly intensified, feeling like it was eating a hole through his stomach. She's playing out her favorite fantasy for real, he realized as he watched his wife getting turned on by the cop's search. One of his hands white knuckled the steering wheel, the other slipped down to rub his crotch.

  Then he realized what he was doing, and was shocked by how hard his cock was. Wh
at the fuck is wrong with me?

  The cop's hands slid down her body, disappearing beneath her skirt. Evie gave a low, throaty purr. He's fingering her pussy, Frank realized. Sweat broke out on his forehead and his hand started to absently rub at his crotch again. And she's loving it. Though the cop's hand was hidden by her skirt, his fingers were obviously pumping in and out of her sheath. His wife squeezed her eyes shut, moaning as she enjoyed his touch; tongue pursed between red lips.

  “You are such a dirty whore,” Officer Connoly laughed. “You like my cavity search?”

  “Fuck yes,” she moaned. “I love it! You're very skilled!”

  “I've had lots of practice.”

  His wife gave a throaty, wicked laugh. “I bet you have, Officer! Oh fuck!”

  The cop glanced at me, grinning broadly. “This little whore's going to cum all over my fingers!”

  “Yes, yes!” she gasped, arching her back. “Search my pussy! Be very thorough, Officer. I've been very naughty!”

  Frank swallowed; his hand still rubbed his cock through his pants. I should be stopping this. The cop's molesting my wife and she's enjoying it. It hurt to watch his wife be the whore for the cop. The betrayal and lust churned his stomach acid until he felt like throwing up—and made his cock as hard as a steel I beam. Why do I find this so goddamn exciting?

  “Oh my god! He's making me cum Frank!”

  Evie writhed, her one freed breast swaying as she exploded on the cops probing fingers. Her face contorted, a wild, exulting expression grew on it as she screamed her passion for all the world to hear. Grinning, the cop pulled his fingers out, dripping with his wife's juices, and wiped them off on her skirt.

  Like she was filthy. A filthy, disgusting, cheating whore!

  “I'm placing you under arrest for prostitution,” the cop announced, reaching for his handcuffs, while he pulled her hands behind her back.

  “Wait,” Evie panted; her cheeks still flushed from her orgasm. “He's my husband, really!”

  The handcuff ratcheted around her wrist. “You have the right to remain silent.”

  “Really, officer!” I shouted. I was confused about the entire situation; hurt, arousal, betrayal all mixed together in the storm brewing inside me, but I didn't want to see my wife go to jail. “I can prove it!”