The Shy Boy and The Ageing Whore

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A prostitute and a virgin save each other from loneliness.
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Crisp packets, empty cigarette cartons, scraps of paper, disposable coffee cups and other assorted detritus was blown along the grubby, grey street in the brilliant Spring morning sunshine as James hurried along in the same direction as the pirouetting litter.

He too was being led by his own invisible winds; a breeze of turmoil had compelled him to Alexander Street, searching the doorways for number 415. The buildings were tumbledown old but gaudily painted. Eventually he stopped before the right numbers. It looked like every other two-storey house in the street. As he stepped up into the porch he glanced down at a pile of discarded cigarette butts. He almost wished that he smoked so that he would have a reason to delay his entry. He took a breath and pushed open the unlocked front door.

The house was quiet. Eerily so. He stepped further in. On his left was a doorway with no door. He challenged his cowardice then entered the room. It had once been a lounge but was now a reception area with a normal looking desk, on top of which was a telephone, a laptop computer and other normal-looking objects. James hadn't known what to expect but everything appearing so extraordinarily normal surprised him. There was a sofa, a coffee-table strewn with magazines and a potted plant growing high in the corner. He stood and waited. A woman entered carrying a cup, she looked surprised to see him.

"Oh, hello. Can I help you?"

"I, er, I'm, um..."

James had been fearing the worst and was immensely relieved to see her. When he'd had the idea of visiting a prostitute he had thought long and hard (this was his own personal pun) about how to go about it. He'd scanned the online adverts searching for somewhere he wouldn't get ripped off, stabbed, robbed or catch a disease. This place had a professionally worded description, its own discreet website and he even found online reviews by satisfied customers who left gold star ratings.

He knew he couldn't expect a supermodel. Really he was just hoping for someone who was kind and wouldn't ridicule him. He was anxious that the experience wouldn't leave him permanently traumatised and in an even worse psychological state than he was already in.

And yet. The woman sitting down behind the desk was perfectly older than he'd dared hope (for a long time he'd been developing a cougar kink to his masturbatory fantasies) and she flashed him a wonderfully calming, friendly smile as she flipped open a diary on the desk while blowing across the surface of her steaming drink.

"Are you James? The ten-thirty? You're early, honey."

"I didn't want to be late."

"You'll have to wait, I'm afraid. Would you like a coffee? A tea?"

Out of all the myriad questions he'd been expecting to be asked, this was not one of them. The normality of the scene was flabbergasting him.

"No. Thank you. I'm fine. Thank you."

"Please take a seat, you have a little while before your appointment."

The woman gestured to the sofa and James wanted to run: Out of the door, up the street, past the Japanese noodle shops to the bus-stop, jump on the next bus and head home to the safety of his bedroom. He sat down. He twiddled his thumbs. The woman laughed inwardly, she'd seen plenty of nervous clients but she'd never actually seen someone twiddle their thumbs before.

"The kettle is hot," she said, "I can make you a drink."

"No, thank you. I'd probably just tip it all over myself."

He laughed and raised his jittery hands. The woman was careful not to laugh but smiled in a reassuring way. They both sat in silence while she began to type on the laptop.

James tried and failed to not stare at her while she worked. He became aware that he was rubbing his palms quite vigourously on his thighs so he forced his hands to stop. They instinctively went back to twiddling. The woman before him was in her fifties, dressed in an elegant (and deliciously tight) office skirt and blouse. Her statuesque face was enhanced by a practiced dash of blush to accentuate her cheekbones, a touch of dark colour on her lips and a smoky eye-shadow that drew out the vivid hue of her affectionate eyes. The effect on the young man was startling and he was beginning to be very pleased with his choice of prostitute.

He looked under her desk and became, for the first time that morning, still.

James had long since been a devotee of opaque tights, leggings, yoga pants, sheer pantyhose, stockings, hold-ups and knee-socks. He was, he knew, a 'leg man' and this refined lady was sporting one of the finest pairs of pins he'd seen online or off. The fact that her fine, svelte, touchable legs were encased in gorgeously soft-looking, sheer, coffee-coloured nylon was driving the boy to distraction. Incongruously, she was wearing a dark pair of sneakers (she'd spent enough years tottering in provocative but painfully high shoes to earn the right to say to hell with heels).

Perhaps picking up on his intense attention, the woman at the desk crossed her legs. The quiet rasp of fabric being rubbed together seemed to fill the young man's head like a symphony. Her feminine subconscious gave her a spidey-warning (a primordial defence mechanism that most women have ~ we can sense when we're being ogled and maybe under a possible threat). She looked up from her work and the young man quickly looked away at a blank piece of wall. She re-crossed her legs and watched his eyes flicker, darting a furtive glance under her desk.

This was the first time she'd really paid him any mind. She picked up her coffee and sipped while she looked him over. In his early twenties, James was just blossoming into a very handsome man after a prolonged adolescent awkward phase. He was tall but no longer gangly, he was broad but not chubby, he looked fit but not in an artificial 'work out twelve times a week' way. She was happily gazing at him when an alarm bell rang somewhere in the back of her ever-cautious mind: This one's so cute he's probably trouble.

"You must be a kinky one," she said.

The sudden sound made James jump.

"Must I?" he replied.

"Are you?"

"I... don't know."

He was frantically wondering if he'd been caught perving at her sexily long legs under the desk.

"We have two kinds of people that come here," she explained, "Those that are here for obvious reasons, not to be unkind but they find it difficult to attract women because they're, well, too fat, too ugly, too annoying, too arrogant... bad breath, bad attitude, whatever. We have disabled clients, senior citizens... sometimes it's just that they can't be bothered to pretend to be interested in a partner. These people just want sex, straight up, in and out. And good luck to 'em. It pays the bills. And then there're people like you."

James wondered exactly what 'people like him' were.

She got up from behind her desk, bringing her coffee, and joined him on the sofa. He immediately began to feel overheated and regretted wearing a teeshirt under his shirt and jacket. He tried not to allow his beady eyes to wander lasciviously over her nylon-covered legs but he couldn't help himself.

"If there is something special you want," she said as she unconsciously smoothed out the hem off her skirt just above her knees, "If it's something wet or dirty... spit, piss, shit, puke, you know, if you want to put something up a bottom or have it put up your bottom, you should tell me."

The naive lad was shocked.

"Is there any way we can do this without anything going up anyone's bottom?"

"We may have to get out the rubber sheets. There'll only be a small extra charge but it's only fair that you give me some warning."

"I..."

"It's okay, I know, you're here because you want try the things your girlfriend won't do."

"I, I, I don't have a girlfriend."

"That's a shame, honey, did you split up over this kinky stuff?"

"I'm not ki- I..." James' eyes were fixed to the floor, "I've never had a girlfriend."

She didn't know if she believed him. Now she was closer she could see was even more pleasing to look at. If this was California, this pleasant looking young man would definitely be an aspiring actor, he'd be a shoe-in for some soppy teen romance. He was (she recalled the word from her own distant teenage infatuations) dreamy.

"Really?" she said.

He nodded.

"I have anxiety, chronic anxiety. I can barely bring myself to talk to people, even people I know, my family... and when it comes to pretty girls, I just fall to pieces. I..."

"But you're talking to me?"

"Yes, I am."

He raised his eyes off the floor, the full beam of his desperate but vivacious eyes hit her and she was stunned. He looked so adorable. She felt herself flirting before she knew it was happening.

"Is that because I'm not a pretty girl?"

"You're the most beautiful woman I've ever seen."

Despite her many years, she blushed. She touched her hair, tucking a stray strand behind her ear. She looked away and sipped her coffee. James gulped audibly.

"I, I don't know how I can talk to you. At this stage of a conversation I'm usually reduced to a puddle of twitching effluence on the ground."

"Well, I'm glad you're not that," she put her coffee cup on the table, "I wouldn't want to have to clear that up."

"By now the room would be spinning and, um, my ears would be ringing from the gathering pressure and I have, um, no way of, aw shit, now I can't stop thinking about it, it's, I, I..."

James' breathing was shallow and fast. She became concerned when he began hyperventilating. She didn't know how to react to the young man dissembling in front of her. She acted entirely on instinct. She kissed him.

Her lips pressed softly against his and she felt his every tremor. She raised her hand and touched his face to soothe him. After a minute she sensed him calming and she paused the kiss to see that his eyes were closed and his large, sexy, pouty lips were ready for more, so she kissed him again. A soft, sensual smooch that they both relished and savoured. The only sounds in the room were quiet involuntary moans of pleasure.

'Well,' she eventually thought, 'I can't do this all day.'

She sat back and watched him open his eyes. He looked so charmingly astonished that she had to pull him close and kiss him once more. Just once more, she told herself as she felt his lips squishing against her. Finally she let him go, their faces remained close enough for their noses to touch.

"Is this, is this part of the thing?" he asked.

"No," she laughed gently, "I'm just kissing you."

"Why would you want to do that?"

"You're very kissable."

She rubbed her thumb across his lips.

"Lipstick," she said.

"You thought," she pondered, "Being with a woman would, um, break the spell you're under? Give you some confidence? It's not a bad idea."

"It sounds stupid when you say it out loud."

Her hand explored his soft face. They were so close it seemed a shame not kiss him again. Their lips touched. A door opened loudly down the hall and they both jumped at the sudden noise like they'd been caught up to something naughty. She picked up her coffee and sat back against the sofa as heavy footsteps approached. A bulky, wobbling lady strode in and went straight to a cupboard built neatly into the wall.

"We gotta get some more cherry flavoured rubbers, these blueberry ones make their junk taste moldy."

She pulled a box of condoms out the cupboard and swung it shut with her hip. She stood in front of the pair on the sofa, James looked up at her, bewildered and confused. She was heavily overweight, her straggly hair was dyed a dark pink, she was wearing only red silk sagging panties and a pair of spike-heeled boots.

"Who's this? Are you next? You're early, sweetheart."

"I didn't want to be late," James repeated.

"I'll soon finish up in there, alright darling? Victoria will look after you while you wait."

The chubby woman clumped off and they heard the distant door click shut.

"Are you, are, are you not Elizabeth?" James asked.

"No, I'm just the receptionist."

"I thought..."

"You must be relieved," she smiled, "I bet you thought you'd got stuck with some old bird."

James glared at the floor and muttered.

"What was that? I didn't catch it."

"I'd much rather it was you," he said, still under his breath.

She kissed his cheek.

"I wouldn't let her hear you saying that."

James looked miserable. She was having fun. She decided she needed some more fun in her life.

"If I gave you my number," she said, "Would you call me?"

"How do you mean?"

"To meet up. For a date."

His face lit up, "I would like that very much."

She stood up, wriggling to get out of the low sofa, and crossed to the desk. She tore off a scrap of paper and wrote down her telephone number. She looked over her shoulder and smirked at she caught him looking at her, his eyes roaming up her legs to her behind. She turned and held out the scrap. He stood to take it.

"You won't forget to call?"

"No, I won't forget."

"I'm not really Victoria, by the way, and she's not Elizabeth. My name's Lucy."

She held out her hand and he shook it very formally.

"I'm J-James."

"Yeah, I know."

She didn't mean to giggle and she was glad when he too giggled and made a stupid face.

"Course you do, sorry."

James walked to the doorway.

"Don't you want to wait and go in?"

"No, not at all. I didn't really want to in the first place."

She walked across the room and kissed him, another long and tender smooch.

"Call me."

"Erm, how much... do I pay?"

Her eyes flashed dark with anger.

"For me?" she said coldly.

"No, no, no," James held up his hands in a gesture of surrender, "No, I mean for the thing."

He nodded down the hall, indicating where the fat faux-Elizabeth was going about her squelchy business. She turned back to her desk and breathed, recovering from her mistaken insult.

"Oh, nothing, I'll tell her you skipped. Happens all the time."

James hovered at the door, eventually he said, "That doesn't seem right."

"No?"

"I assume my appointment meant... well, she'd be earning money if I hadn't... erm..."

"It's alright to change your mind."

"But I don't anyone to be out of pocket. How much would it've been?"

She ran her finger down the page in the diary.

"Seventy-five," she said.

James walked over, pulled out his wallet and began counting out notes. She picked up her coffee but noticed it had gone cool. James was finishing up the amount with the last of his coins.

"This is very conscientious of you."

"It only seems fair."

"You sure you got enough?"

"Don't worry, I'll have enough to take you out," his voice was earnest.

She laughed lightly and kissed his cheek.

"I wasn't worried,"

He shook her hand again.

"I'm glad I met you, Lucy."

"And I, you, James."

He ran his fingers through his hair, flashed her an awkward grin then exited. She leaned back against her desk. Her heart was fluttering. She hadn't felt this apprehensive in a long time. It suddenly dawned on her that she was really hoping the young man would call. She reprimanded herself for being so silly and got back to work.

*******

It was a nervous couple of days for Lucy until she received the call. James didn't know any bars so she picked an Italian cafe-style cocktail bar she enjoyed visiting, knowing it would be a calm, quiet place for him. The interior was a sombre red and black, the music was soft, voices were kept low. As she sat waiting, she sipped her dark, sweet drink and agreed with herself over her sensible choice of venue. She'd been waiting a while and was just beginning to fear she'd been stood-up when James bustled through the door.

"Am I late? I lost track of time because I've had about eighteen panic attacks on the way here."

During the three nights she'd kept her phone close by, just in case the call came at a weird hour, she'd been imagining and fantasising and playing with herself; her typical method of self-stimulus was two fingers dipping in and out of her aroused pussy while the palm rubbed her hot little button. Her favourite fantasy, one she returned to whenever she felt an increasing urge to climax, was thinking about sitting on his face, watching his beautiful eyes looking up at her through her trimmed pubes as she taught him how to eat a woman. In none of her fetid fantasies, however, did she picture James as he appeared now in the bar: Red-faced, sweating, clutching his chest, breathing heavy and some kind of terror in his eyes.

"Have you been running?" she asked.

He nodded and his words came at a sprint, "I got off the bus in completely the wrong place, then my phone didn't know where I was and I was lost but too scared to ask anyone and... I ran because I hated the idea that you'd think I wasn't coming. Did you think I wasn't coming?"

"No. Maybe. A little."

She stood and walked around the table. He watched her from beneath a messed brow of sweat soaked hair. She loosened his tie and undid the top buttons of his shirt. She pulled over her bag and found a tissue, she reached into her drink to fish out an ice-cube, rolled the tissue around it and rubbed it on James' forehead. His breathing worsened.

"How do you usually cope when you're feeling anxious, James?"

"I skulk away and, and detest myself later."

"Nothing helps?"

He shook his head, he was obviously suffering mental anguish. She leaned closer and placed her lips on his. It had worked earlier, she reasoned to herself. After a few seconds his breathing softened and he returned her kiss. She gave him a series of delicate kisses, soft and loving, as she calmed his raging senses.

"You are magic," he said when he could finally speak again.

She sat back down and took a drink.

"Maybe it says something about me that... you find my kisses the opposite of exciting."

"You couldn't be more wrong," James tidied his hair away from his eyes and placed a finger and thumb on his forehead. She watched as he drew them slowly together.

"You focus me," he said, looking very intense, "When you, you're... kissing me, I can't think of anything else in the world except how amazingly wonderful it feels and how lucky I am to... whew, I, er..."

"Let's go sit outside, in the air, shall we?"

Lucy had another tall cocktail while James opted for fizzy water. The evening air did indeed help James and he cooled his jets enough to relax and shine a little of the charm he hoped he had. It was a busy part of the city and the sounds of urban life helped distract his thoughts from becoming too disordered.

To his amazement he discovered Lucy was a fan of Star Wars and had been ever since seeing the first film as a young girl; he was so thankful because he'd had a number of brain haemorrhages trying to imagine what on Earth they'd talk about. She was pleased to discover that he hated modern pop and had a fondness for the music that she'd enjoyed as a teenager, although part of her was uncomfortable that he talked about Adam Ant and Billy Idol as figures from History.

During the couple of hours they sat together, Lucy would occasionally lean over and kiss the boy and then sit back and sip her drink with a sexy, satisfied smirk on her features.

"I like the way you look when I kiss you," she told him after a particularly long and sensual exchange.

"How do I look?"

"Like you can't believe it's happening."

She smiled broadly at him and he blushed and looked away at the passing traffic.

"Lucy, I, I have a question."

'Shitfuck shitting fuckfuck,' she thought, 'Here we go with The. Fucking. Question.'

"I know what you're going to ask."

"You do?"

"I work with a prostitute. Am I a prostitute? What kind of a prostitute am I? What do I do? How often? How much do I make? How could I possibly do something so sordid? What went so wrong in my life that I would choose to do it? Exactly just how much of big ol' whore am I?"