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The Accidental Escort

"A sex-hungry woman allows a case of mistaken identity to unfold…"

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Eleanor pulled the sheer black stockings over her freshly waxed legs with excitement. It has been months since she’d been laid. She had broken up with her boyfriend and then ran straight into a Covid spike. When Covid ebbed she tried her hand at the dating apps and was very disappointed. After several jerks that over-advertised their jobs, hobbies, and fitness, and who were pretty disastrous in the sack, she decided to take a break from trying.

Gay porn and a vibrator let her get by for a while, but eventually, she longed for another human’s touch — and a real dick. She ran into her ex, Jake, on the street one day and they went for a drink. They had a few laughs and a few more drinks. In a drunken moment, he confessed that his new girlfriend was a stiff in bed compared to Eleanor. She rolled her eyes and patted him on the forehead.

“Yeah, sure.” She laughed. “Listen, if, when you sober up, you still feel that way, you can ping me for a booty call. I assume you still have my number.”

She hadn’t really meant it; it was just a drunken joke. But a few days later she got a text.

Hey. Wanna meet on Thursday. GF OOT. The Metro Hotel bar. Like old times.

Eleanor closed the text without answering. The Metro Hotel was where she and Jake had first met. She wasn’t going to fall for it. But after a couple of days, Eleanor couldn’t get it out of her head. Jake was an unreliable boyfriend, but he was a reliable lay.

And so, here she was, getting all sexied-up. It wasn’t for Jake. It was for herself. She just felt like being desirable. The sex would be all the better if she felt beautiful. Her legs weren’t the only things she’d had waxed that day. She’d gotten a fresh mani-pedi, too. And, while Jake would have been plenty satisfied if she’d shown up in jeans and a t-shirt, she was going all out. She’d swung by Victoria's Secret and picked up the stockings, as well as a new black lace demi-bra and matching thong. And now she was pulling on one of her sexiest little black dresses, and her high-heeled black Louboutins, for good measure.

When she walked into the Metro Bar, more than one head turned. The bartender beamed as she took a seat at one of the high tops, and he rushed over to take her order. Eleanor felt very sexy, indeed. She ordered a Vesper and waited for Jake with excited anticipation. And she waited. And she waited. And then she received the dreaded text:

Sorry! GF changed plans. Not leaving town. Talk to u soon.

Eleanor shook her head in disgust and disappointment and then ordered another Vesper. Fucker, she thought to herself. I can’t believe I waxed my pussy for this.

Eleanor felt the second Vesper seep into her brain as she stared blankly at the dinner menu. Suddenly, her fog was broken.

“Um, Ellie. You’re Ellie, right?” a deep voice asked. No one had ever called her Ellie. She looked up to see a very handsome black man. He had a closely cropped haircut, a brilliant, bright smile, and a gray tailored suit. He was gorgeous. And she had no idea who he was.

“Yeah, hi. I’m Eleanor. Nice to … see you,” she said, holding out her hand.

The handsome stranger took her hand “You’re even prettier than your picture,” he said.

Picture? What the fuck is this guy talking about, Eleanor wondered. Her confusion must have shown on her face.

“From the website. Yeah, I’m sorry. Your picture on the website,” the handsome man explained.

“You mean, like, LinkedIn?” Eleanor asked. The guy broke into a loud laugh.

“And a sense of humor, too. This is going to be fun,” he said, holding up two fingers to the bartender and nodding his head toward Eleanor’s mostly empty glass. Quickly, two fresh Vespers were on the table in front of them. “No…I guess it would be your ‘company’ website,” he said, with air quotes.

“So, you’re a client?”

“Um, yeah. I’m John, your client,” he answered, again with air quotes.

Eleanor was super-confused, but the guy was super-cute. And she was super-horny. So, she decided to roll with it a while longer. They sipped their drinks. He laughed at her jokes. He complimented her dress. He clearly liked looking at her. He exuded confidence. She was smitten. Then she noticed a gold wedding band and gave it a quick point, coupled with a “so-what’s-up?” squint.

He gave her a curious look, and said, “Oh, I can take it off, if you like. They usually don’t mind.” It was an odd thing to say; said in an odd way. But Eleanor didn’t really care. She’d likely never see the guy again. And he was so hot — married or otherwise. She could manage to stare at his handsome face and overlook the ring.

“So, you want to join me for dinner?” Eleanor asked as the vodka and gin zapped all that remained of her inhibitions.

John, again, gave her a curious look. But, after a moment’s hesitation, he said, “Yeah, sure. This is nice. The room can wait. And I haven’t done GFE in a long time. You’re fun, Ellie. And damn, you’re my type to a ‘T.’ I love that long brown hair and those deep brown eyes. And those dimples.”

Now it was Eleanor’s turn to give him a curious look. GFE must be some kind of dietary thing, she told herself. But she enjoyed his compliments. She felt herself blush.

They shared a few appetizers and had another drink. Eleanor began to steel her resolve. He’d mentioned a room. There was that weird ring remark. I think we’re going to fuck, she thought to herself with a smile.

John felt a buzz against his thigh and pulled his phone out of his pocket. He held up his hand in apology and glanced at the screen. I hope it’s not the wife, Eleanor thought. John’s curious face was back, followed by a shake of his head and a half-laugh.

“It’s a text from your agency. It says, ‘Very sorry but Ellie will not be able to make your appointment. Your account will be credited the Bitcoin equivalent of $250.’ What the hell?”

Eleanor processed the odd strands of information that had spun out over the last half hour as best she could. The Vespers made connecting the dots harder. He thought her name was “Ellie.” She didn’t look quite like her picture. That picture was on a mysterious website. He was a client that she had never met or heard of. His name was John. He hadn’t shared his last name. An appointment with “Ellie,” which involved a Bitcoin deposit of $250, had been canceled.

My god, he thinks I’m a fucking escort, Eleanor realized as she nearly spat out her drink. She weighed the bizarre circumstances. She balanced her propriety against her lust for the gorgeous man in front of her. And then, to her own astonishment, she uttered, “Must be some kind of a glitch. Should we head upstairs?”

“Absolutely,” John said, as he waived to the bartender for the addition.

~

John badged the hotel room door and pushed it open for Eleanor to step through. She felt lightheaded, and her knees were shaking. She was nervous. It was a well-appointed suite with a large seating area. Pretty nice for an escort, she thought to herself.

“I don’t think I can make a Vesper, but I can manage a vodka soda. Would you like one?” John offered.

“Sure,” Eleanor managed to squeak out, as she sat on the sofa and tried to catch her breath.

John handed Eleanor her drink, clinked glasses, and sat beside her. She struggled to find words or to know what to do next. John ended the brief, awkward silence.

“Oh, yes, of course,” he said, as he pulled an envelope from his breast pocket. “I don’t know what’s up with the Agency fee, but here’s yours,” he said, handing Eleanor the surprisingly thick package. “I understand $1,000 will cover it.”

Eleanor took a gulp of her drink. “Um, yeah, sure, um, please excuse me for just a second.” She mindlessly stuffed the envelope into her small purse and headed to the bathroom. She stared at herself in the mirror as she struggled to slow her heartbeat.

Why are you so nervous?! She asked her reflection. You’re just here for a good fuck. You’ll leave the money. You’re not a whore. You’re not doing anything illegal. You just want some dick. Go get it.

Eleanor stood up straight, took a deep breath, and stripped out of her dress. She pulled up her stockings and pushed up her tits. She touched up her lipstick and walked back into the room.

“Damn,” Ellie. “You are fine. Get over here.”

Eleanor straddled John’s powerful thighs and wrapped her arms around the back of his neck. He gently stroked her ass, back, and waist. He reached up to push a strand of her hair away from her face. That did it for Eleanor. She leaned in and planted a kiss on his pillowed lips. He seemed surprised but returned her kiss with intensity. They necked like teenagers, complete with heavy petting and dry humping.

“My god, Ellie. You are the sexiest. I like how slow you’re going. You aren’t like the others.” John said in his deep voice. Like the other escorts, Eleanor thought to herself, both pleased and horrified, with his compliment.

John unsuccessfully fiddled with Eleanor’s bra, like an awkward teen. Eleanor pushed his hands away and stood. She slipped out of her bra to fully reveal her 34Cs, and then pirouetted on a Louboutin and pulled her thong past her ankles with a gymnast’s pike. She righted herself, flipped her hair, and walked seductively toward the king-sized bed on the other side of the suite. John’s eyes followed the flexing globes of Eleanor’s heart-shaped ass.

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Eleanor looked over her shoulder with a come hither smile, and said, “Let’s see how else I’m not like the others.” She flung herself onto the bed like a rambunctious child and then rolled onto a hip. She supported her head with a crooked arm and drank in the tall handsome black man walking toward her. John began to crawl on the bed after her, but Eleanor held up a hand.

“I want to see you strip out of that suit…really…really…slow.”

John chuckled and shook his head in disbelief, but followed her direction, peeling off his Canali threads and laying them carefully on a side chair. “Nope. Not like the others at all.”

“Socks, too, big boy,” Eleanor chided. And “big boy” was accurate in more ways than one. In place of Italian wool was now his smooth, dark skin, stretched taut over firm muscles. Broad, muscular shoulders framed his large pecs, and a washboard six pack led to his chiseled groin. And, while she tried to keep her eyes from going there, she eventually gave in to her curiosity. Don’t be small, don’t be small, don’t be small, she found herself thinking as John dropped his small, black briefs. A lovely, large, uncut cock swung free and came to full life in front of her eyes. She involuntarily licked her lips.

Eleanor rolled onto her belly and undulated her way to the edge of the bed. She supported herself on her elbows with her legs spread wide behind her. John’s cock stood before her in all its glory and she stuck her tongue out to flick at a bit of pre cum. She grasped its base. It was thick and warm in her fist. She admired its gentle curve and perfect proportions. She wished she could take a mold of it and take it home.

Eleanor felt her confidence suddenly wane. I bet a high-end prostitute could take this kielbasa all the way down, she thought. There’s no fucking way. So, she decided to make love to it. She pushed his foreskin back and took just the fat tip between her lips as she slowly, gently encircled it with her wet tongue. John’s groan encouraged her. She slowly kissed and tongued her way over every bit of his perfect pole. She traced a thick vein that ran along its length, back and forth, back and forth, until John gasped. She then put attention to where the dark wrinkled skin of John’s contracted balls met the smooth skin of his cock. It was not a quick lick. She lingered. She alternated kisses, with light suckling, and generous laps.

“Sweet Jesus, Girl,” John moaned. “Your attention to detail is fucking amazing. I need to fuck you, now, or I’m going to blow all over that pretty face.”

John’s warning only inspired Eleanor further. She continued her slow, sensual tour of John’s cock until he was unconsciously thrusting his hips and clenching to hold back a building orgasm. Eleanor suddenly twisted onto her back, tilted her head over the edge of the mattress, and stuck out her tongue with a begging whimper.

“Ah, fuck,” John cried as he slid his cock into Eleanor’s wanton mouth. Eleanor pressed one hand against the hard muscled wall of John’s groin to regulate his speed and depth, while the other fondled her smooth mons Venus.

Being enveloped in the pretty brunette’s warm, soft mouth, while staring down at her lovely twenty-something body as she pleasured herself, proved too much. As much as he wanted to stretch his time with this quirky, sexy girl, Ellie got the better of him. He fondled her pretty breasts and even pinched her nipples, hoping he would be able to deflect his impending explosion. But it was to no avail. He pulled out and shot three or four thick, ball-wrenching ropes onto her belly and breasts.

“Ah!” Eleanor exclaimed with disappointment, “I wanted all of that!” She guided John back to her mouth, and licked his head, as she savored the last of his cum.

“Jesus! You’re fucking amazing, Ellie,” John groaned. He brought Ellie some tissues and then joined her on the bed. He pulled her to him. Cuddling was not something he typically did with prostitutes. But she was different. She really did the “girlfriend experience” well. He half wondered if acting was her day job. She was so natural. John surprised himself as he began kissing Ellie’s cheek, then neck, then continued down, suckling her nipples, tracing a line along her stomach with his tongue. He pulled off her high heels and tossed them aside, then slipped her left stocking off, followed by the right. He reversed his adoring direction, kissing her pretty arched feet, calves, and thighs, before lingering at her plump, smooth mound. He kissed all around, and then used first one, and then a second finger, to play with her wet lips and clit.

Oh god, why doesn’t he eat me already?! Eleanor screamed inside her head. Oh, yeah, because I’m a whore. Guys probably don’t eat out whores.

John was plenty skilled with his digits, however. He sucked on Eleanor’s breast as he put two fingers and his thumb to work. He teased and edged her until she was literally begging.

“Please, John. Yes, please. Finish me. Finish me,” Eleanor moaned as she clung to his muscular upper arm. “Fuuuuuck!” she groaned as she spasmed John’s hand.

“Thanks,” Eleanor said with a chuckle.

“You’re quite welcome,” John said, “that was fun to watch.”

Eleanor stroked John’s hard, brown body. Without meaning to, she found his cock. It had returned to its full, rigid state. She stroked it with just her fingertips, then gave it a playful scratch with her freshly manicured red nails.

“Ah…that feels good,” John moaned. “Hey, I know it’s bad form to cum twice, but would you consider giving me a chance at round two? I really need to fuck you. I don’t have any more cash, but I could send a tip in the app.”

Eleanor smiled. “If you don’t fuck me, I’ll charge you double!”

John hopped out of bed like an excited teenager and grabbed a condom from his jacket. When he returned, Eleanor was on her knees.

“Let me,” Eleanor said, taking the condom package from him. He knelt beside her, kissing her, a hand on her waist and the other cupping a breast. Eleanor broke the kiss and gave him a cheeky smile. She brought the foil packet to her mouth, and then tore it open with clenched teeth. Without breaking eye contact she expertly rolled the latex sleeve over John’s rod. It was a snug fit.

“How do you want me?” she asked seductively.

“In every way,” he said as he pushed Eleanor onto her back. She pulled her legs wide apart. John looked down upon her, almost lovingly, as he worked his way into her. She was soaked, but he still had to go slowly. He worked a bit in, and then would withdraw, and then re-enter her, a little deeper each time. Soon enough Eleanor felt his hard groin against her clit, and his big balls against her asshole.

He felt fantastic. Thick enough, and long enough to stretch her more than what she was used to, but not so big that he hurt her. She could take all of him. His brown eyes stared into hers, as he moved within her.

“Fuck this is good,” Eleanor uttered without thinking.

“Yeah, it really is,” John grunted.

“Can we finish this way?” Eleanor asked, almost pleading. John nodded.

They proceeded to fuck in any manner of positions, all over the suite. Eleanor almost came as John fucked her from behind. standing at the window sill. She came buckets as she rode him in cowgirl on the sofa. She was pretty sure John, himself, was on the brink of cumming as he took her, roughly, doggystyle, on the leather ottoman. And then the condom broke.

“Goddammit!” John cried in frustration.

“It’s fine. It’s good,” Eleanor said as she lay back against a pillow and once again spread herself open, invitingly. “I want you to finish, like you promised.”

John re-gloved and enter Eleanor in missionary, once more. “That what you want, baby?” he asked, knowing the answer. Eleanor nodded and whimpered as he filled her.

She stroked his strong arms and chest, then cupped his lovely face. Could there be a sweeter whore, he asked himself as he looked down upon Eleanor’s dimpled smile. “Ready?” he asked. She nodded, again. John lengthened and quickened his pace, but he didn’t pound her. He worked in steady strokes, making sure to drive against her clit on each downstroke, but not so hard as to overstimulate her. When at last he felt her tremor, he sped up just enough to trigger his own release, and they came, together, like lovers.

They lay together in a sweet embrace, but said little, as they recovered their breath. And their senses. John kissed Eleanor on the forehead and addressed the inevitable.

“Hey. This was amazing. Truly. You are a delight. Maybe we could do this again, sometime.” John said, awkwardly.

“Sure,” was all Eleanor could muster.

“You can stay if you like,” John said, disentangling his brown limbs from her white ones. “Order room service. Pay per view. Whatever you want. I’m afraid I need to shower and head back to the burbs.”

Eleanor lay there for a bit as she heard the toilet flush and the shower turn on. I need to get out of here.

She recovered her stockings and pumps. And then her underwear, and finally, her dress, which John had kindly hung outside the bathroom door. She did her best to smooth her bed head, and braced herself for the walk of shame in the hotel lobby.

She pulled the envelope from her purse and stared at it. It has been oddly fun to fuck for money. She set the envelope on John’s suit jacket, where he would be sure to find it, then started for the door. As she grabbed the door handle, Eleanor stopped. She turned around and grabbed a Metro Hotel pen and then scrawled on the hotel stationery: “John — thank you for a wonderful evening — Eleanor”. Then she opened her wallet and pulled out the sixty-five dollars in cash that she had, and laid it next to the note.

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Written by Longing
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