The Shy Boy and The Ageing Whore

"I, I..."

"Well, the answer's yes. I have worked as a prostitute, for a long time but not so much these days, what with me getting long in the tooth. They want... a younger model so I moved into the admin side of things. Sometimes I still do it, if a man comes in wanting a mature experience, we'll charge him a helluva lot extra and I'll do whatever he wants. Within reason. I've been involved with sex-work for, wow, nearly thirty years and I don't plan on changing any time soon. I have a mortgage to pay and it put both my kids through college."

"I wasn't..."

"I never walked the streets. We always use condoms. I have done porno and no, I won't tell you the titles so you can Google 'em."

James gulped. Lucy adjusted her hair and her dress, this dreaded part of a relationship always made her feel like her skin was on fire but she found it best to get it over with quickly.

"Did that answer you question?"

"No."

"Oh."

"I was going to ask if you like horror movies."

"Oh."

Lucy gulped. He looked like he'd done something wrong but he didn't know what, so he plowed on hoping he could recover the evening's light and pleasurable atmosphere that seemed to have evaporated. He often had this effect on people.

"There's one on tonight, at the cinema just around the corner. It's not supposed to be very good, but I thought, we... thank you though, for telling me, all that. I, I, er, appreciate your honesty."

"I am going to use the bathroom," Lucy gathered her jacket and bag, "If you were hoping for a discreet and non-embarrassing way to leave me, this would be that opportunity."

Lucy drank the remains of her cocktail and walked inside the bar. In the Ladies' loo, she had a wee then spent several minutes examining herself critically in the mirror over the wash-basins.

'What are you doing?' This question repeatedly fired through her mind as she saw, with an eagle's clarity, every last wrinkle on her face. 'You old fool. You stupid old cow. What are you doing?' She re-applied her lipstick, smoothed her hair in place and steeled herself for disappointment. She walked through the bar and stepped outside. He wasn't there.

A couple, a YOUNG couple had taken their place and were having their own intimate discussion. Despite her iron-like armour, despite her many years of tough, hardened living, her heart dropped like a stone. She stood transfixed by the boy's absence.

"I think we lost our table."

She whirled around to see James struggling through the heavy door with a glass in each hand. She held it open for him.

"Whew, thanks. I went to get us some drink-"

He was interrupted by the tightest hug he'd ever felt. He was immobilised by the glasses in his hands but Lucy did not lessen her embrace and buried her hot face in his neck.

"I thought maybe you'd run out on me," he said to the top of her head.

She pulled back and touched his face.

"Run out on you?"

"It's happened before," he handed her the dark cocktail and sipped his water, "She emailed me later to say I'd been painfully awkward and she couldn't bear a single second more in my company. We were twelve."

He chuckled and she joined in, in spite of her tangle of emotions.

"When's this film start, James?"

"Erm," he checked his phone, "We have a few minutes, if you wanna go?"

Lucy took a long swig of her drink, took James' glass and plonked them both deliberately loudly on the table they'd had stolen. The couple at the table looked offended. Lucy took James' arm and they walked off.

*******

They sat in the cinema with a small carton of popcorn between them. When their fingers touched, reaching for a piece of popcorn, they would linger at the contact, their digits gently playing. During one of these intimate moments, Lucy looked down and caught a glimpse of her fingers in the weird illumination of the flickering film and, compared to the flawlessly smooth skin of the youngster, noticed how old her hands looked. The ungenerous grey light of the movie made the wrinkles at her knuckles seem as deep as craters on the moon. She looked at the boy sitting next to her as he watched the movie and she began, again, to question what she doing. Was she fooling herself? She glanced around at the other movie-goers, did they all think she looked like a foolish old trout?

She was beginning to feel quite low when James leaned over and kissed her.

"I'm so glad you're here," he whispered, "I'm so glad I met you."

He kissed her again and the weight lifted from her soul.

"You're bolder in the dark, aren't you?" she whispered back.

"I feel more handsome in the dark."

He laughed at his own joke.

"I think you're very handsome."

She kissed him and compressed into her passion a reward for all the joy he had brought her. She hadn't realised quite how unhappy she'd been for such a long time, her everyday miserable loneliness had become normal; it took a sudden burst of genuine glee in glorious technicolour to bring home to her how much she missed being adored, being the subject of a young man's infatuation.

James, as always, was a little startled by the passion with which he was being smooched. Emboldened further, he placed his hand on her knee.

James had been, if he was being completely honest with himself, quite disappointed with how Lucy had dressed for the date. In particular it was the long skirt that reached down to her calves that was tantalisingly hiding all but a flash of sheer black nylon at the top of her boots. It was a very pretty skirt, no doubt very stylish and expensive, but he had wished she'd revealed more of her lithe legs. He'd been thinking about her legs a lot. When she'd crammed herself into the narrow cinema seat, Lucy had to bundle up the hem of skirt to get comfy, revealing more of her nylon-clad curves and this had held far more fascination for him than the tedious horror movie. He knew it was odd to be so enamoured of a pair of knees so he tried to keep his admiration of them covert. Now, though, he touched one.

The feel on his warm palm of the soft fabric stretched over her flesh was every bit as arousing as he'd ever dreamed of in all his leg-based web-porn wanks. Lucy immediately sensed his devotion and slid the hem her skirt even further up, revealing her thighs. James looked in her eyes and she smiled back at him, encouraging him to be bolder. He slowly traced his palm along her leg until it came to rest under her skirt.

"Kiss me," she whispered.

As they kissed, his hand began to wander around, exploring the tug of the smooth material. She opened her legs and his hand sailed naturally down her inner thigh. He paused, his breathing was hard. She placed her hand upon his and pulled his palm on to her nylon crotch and moved his fingers against her. She kissed him and parted her mouth. He slid his tongue into her and they shared their first delightfully dirty snog.

They could both hear screaming and loud bangs from the ignored movie. Flashing light penetrated their closed eyes. Her hand pushed his hand against her, grinding the fabric gusset on her hot, wet, squished pussylips.

Eventually, they came to a natural pause and they came up for air, blinking in the light. They gazed at each other in wonder at the powerful emotions they were experiencing.

"Can I... sorry, I'm not being rude," James put the popcorn carton on the floor then wriggled stiffly in his seat until he could push his hand down the front of his pants.

"What are you doing?" Lucy giggled, looking to see if anyone else was watching him.

After some fiddling he sat back down properly.

"My dick is so hard, and it was, like, being snapped in half, I had to, y' know, rearrange things."

Lucy laughed. This made people look around because it was one of the quiet scenes of the film.

"I'll take that as a compliment," she whispered.

She reached over and softly stroked the bulge in his pants.

'A huge compliment,' she almost said, but held back at the last second, thinking that it was the kind of lie she'd use at work, praising some pencil-dicked 'John' so he'd hurry up and cum.

James then did something which reinforced to her that she hadn't been to the cinema with a date for quite some time. He lifted the arm-rest between them.

"I didn't know they did that," she whispered.

He put his arm around her and she nestled in against his warm body. She pushed two fingers through a gap in his shirt, where the buttons meet, and her fingertips stroked his belly as they watched the rest of the movie.

*******

James walked her home when the movie ended. They were turning the corner of her street as he told her that something had happened during the film.

"You know when you went for a pee? While you were gone, the guy who was sat next to me leaned over and said, 'Izzat your girl?'" James imitated a low, tough voice, "I said you were, I hope that's alright,"

"That's fine," she replied.

"Then he said, 'She izza MILF!' then he put his fist up, like this," James held up his fist.

"You fist-bumped?"

"I did, then he said, "You's one lucky motherfucker, she is hot!'"

"What did you say?"

"I said, 'Yes she is, and thank you.'"

"It's flattering to us both, in a way, I suppose."

They walked for a while in silence.

"Is that what you think?" she asked, "Am I a hot MILF?"

He pulled her close and kissed her.

"Unquestionably," he said.

"This is me, here."

She indicated a nine-storey building and stood on the first of the steps that up to a pair of thick, glass doors.

"Well, um, goodnight," he said, "Can I... call you again?"

She stepped back down to the street and stood close to him. She put her hand on his cheek.

"I want to make love with you," she said softly, "Won't you come in?"

"I... didn't... want to assume."

"You were right not to assume. Very respectful, thank you," she leaned closer and whispered in his ear, "I want you."

"I have no idea why."

"You're very attractive. And charming. And, on top of that... your innocence makes me so fucking horny."

She wrapped her arms around his neck and they kissed.

"I have to warn you, I, I have no experience."

"Have you any idea how exciting that is?"

He shook his head.

"Everything I do to you, will be the first time anyone's ever

done it to you," she kissed his neck and purred, "And I have so many things I want to do to you."

She took his hand and lead him up the steps. She unlocked the doors and began walking up the internal flight of stairs.

"There's no elevator in these old buildings. Still, it keeps your legs fit."

"I love your legs."

She glanced behind her and was thrilled by his gaze of adoration as he lingered so he could see up her skirt. She turned and lifted the front of her skirt, revealing her black pantyhosed thighs. James stepped up and slowly sailed his hands up her legs, visibly aroused. As his hands reached higher, he pushed her skirt up until he was facing her luscious nylon-covered cunt. He pressed his nose to her and inhaled his first ever scent of woman. He kissed her through her tights and her legs turned almost to jelly.

"We'd better not do this here," she said.

She dropped the hem of her skirt and turned to ascend the stairs. James lent against the hand-rail and let his accelerated heart rate drop to a non-lethal level and then followed her up.

Three flights up, and quite breathless, she let him into her apartment. Her home was chic and sophisticatedly furnished, everything colour co-ordinated. She switched on an elegant lamp and leaned on the arm of a long sofa to pull off her boots. He couldn't help watching voyeuristically as she wriggled her delectable nylon-encased toes in relief at their escape from captivity.

"Mmm, that's better," she murmured.

He wanted to drop to his knees and adore her cute toes and sexy feet and calves and... he restrained his perversions, not wishing to appear the gibbering horn-dog that lie barely underneath the surface. He turned instead to look out of the large windows. The apartment overlooked a park and he was thinking that she must be doing well out of... out of... his brain didn't want to acknowledge how she made her money.

"Do you want anything?" she stood behind him.

He turned to face her.

"Only you," he said and blushed.

She kissed him, a slow, all-the-time-in-the-world kiss. James began to undo some buttons on her gypsy lace jacket. She looked down and chuckled.

"They're ornamental, babe, the zip is down the side."

He looked crushed but had enough growing trust in their friendship to laugh it off.

"You must think I'm so dumb."

"Don't be silly."

She pecked him on the cheek then stepped away as she unzipped her jacket. She pulled it off then tugged the sleeveless teeshirt she wore underneath off over her head. She undid the ties of her skirt, it dropped to the floor and she stepped out of it. She picked up her skirt, carefully folded the designer item and placed it on the arm the sofa. Then she was hit, standing there in only her black bra and black tights, by a sudden and unusual lack of confidence. She cared what he thought. She was worried about what he thought.

"Do you like what you see?" she asked.

He rubbed his chin to check he wasn't actually drooling. He wanted to rush at her and devour her like a fat boy eats cake. He held himself in check with what he hoped was an obvious masculine control. Mustering his most debonair swagger, he crossed the room and slid his arms around her waist and began to feel her wonderfully grope-able bottom.

"I want to tell you something, but it'll sound goofy," he said, kissing the nape of her neck, breathing in her subtle perfume, "It's like some higher power reached in my head and plucked all my... dirtiest fantasies and bundled them together to make you."

He kissed her shoulder, down her arm and then dropped to his knees and ran his tingling palms over her pantyhosed curves. The shape of her bumcheeks under the thin layer of soft material seemed especially fascinating to his fumbling fingers and he could've happily stayed there for a few hours, luxuriating in how good she felt to touch.

Remembering their encounter on the stairs a few minutes ago, he pressed his mouth to her warm, damp crotch and began to kiss her. Lucy looked down at her inexperienced lover and felt such power at his utter immersion in her sex, her fragrance, her taste, the sight of her, the feel of her.

"Am I right in thinking you've got a bit of a thing for pantyhose, James?"

He looked up and nodded, his nose rubbing teasingly but accidentally on her clitoris.

"See," she said, "I told you you were kinky."

She allowed him to spend several pleasurable minutes snuffling and snogging her cunt though the nylon barrier but she felt a growing need to feel him more intimately. She hooked her thumbs into the tights' waistband and shoved them down to her knees. She liked the awestruck look on his young face as he, for the first time, came face to face with pussy. Her pussy.

"I want to give you everything you ever dreamed of."

She placed her hand on his head, her fingers entwined in his curls, and pulled him closer. He immediately and instinctively opened his mouth and parted her wet lips with his eager tongue. She gasped as he lapped and kissed and slurped. Lucy felt her whole body washed over with a rejuvenating energy.

'I have missed this,' she thought, 'I have fucking missed this.'

James' brain was reeling with his own overflowing flood of virgin sensations. Kneeling in a strange lounge, licking a half naked woman, lost in the flavours and scents. Was he actually doing it? He'd wanted this for so long, so many years of being alone. He almost thought he was dreaming. Was he at home, tugging on his dick? His dick felt all aglow. Was he touching it? Was this real? Could this even be happening? He wasn't the kind of person to have such luck. He paused and leaned back, his eyes closed, his head swimming, his bone-hard dick throbbing.

"Are you alright there, babe?"

"Mmm-mm. Just a little... overwhelmed."

Lucy pulled up her tights, then pulled him up to his feet.

She gave him a calming kiss and revelled in the scent and taste of her own pussy on his mouth. She had marked him as her own. Her lover. Her boy.

"You, you, I..." he struggled.

"Shhhhh," she kissed him again.

"It is magic, what you do to me."

"Let's go to bed."

Lucy led him by the hand through her apartment and into her bedroom. She switched on the light and James thought it looked like a five star hotel's suite; he wanted to compliment her on her home but didn't know if that'd sound cheesy. Although his confidence had grown immeasurably, he was terrified that he was going to fuck it up. He usually screwed up human interaction and it was only a matter of time before this too went pear-shaped. If he got 'this close' to finally getting some action and then went and messed it up, he'd never forgive himself. So he kept his mouth shut and hoped for the best.

She sat on the edge of her large bed and crossed her legs in a way that she knew would make her nylon calves and thighs look enticing. Then she decided she didn't like the way her belly looked all podged out so she reclined like the 60s Catwoman being visited in her villainous lair by Adam West's Batman, in a reference that would be completely lost on the millennial in her bedroom.

"Strip," she said.

James almost replied, 'Who, me?' but muted his dumb answer and removed his tie. He ran his fingers through his hair and unbuttoned his shirt. As he revealed his taught torso, Lucy purred appreciatively.

"Keep going, lover."

James kicked off his shoes, whipped off his socks, undid his pants and shoved both them and his underwear down. He crossed the room and stood before her with his perpendicular dick jutting out. She sat up and touched his body, her fingernail delicately scratching his skin.

"You're so pretty," she assessed.

"Aren't I supposed to say that to you?"

She smiled and said, "You've got such a pretty dick, do you mind if I kiss it?"

He thought that this was possibly the stupidest question ever asked in the history of mankind so he shook his head slowly.

She kept trailing her fingers over his chest and tummy as she rubbed her lips on his stem. She smiled to herself as James whimpered and then coughed to try to hide his embarrassing reaction. She left dark lipstick smudges on his flesh as she kissed his cock. She had so many things she could do to the young man but she was enjoying the way he trembled at just the barest, gentlest contact.

"Peel it back," she said and James rolled his foreskin back over his dark-red bulbous helmet.

"Mmmmm, so cute. You smell so good too."

She looked up at him, their eyes locked together as she brought her lips to the tip of his cock. She watched him shudder. He looked so serious.

"I want you," his voice was low and demanding, "Now."

She bit her lip, she couldn't remember that last time she was this inflamed with desire for a man. She was feeling very thankful to her young gentleman for awakening this higher level of arousal. She would have denied him nothing.

"Come lie down," she said.

James joined her on the bed and lay on his back, his cock pointing proudly upright. She curled her fingers around the solid shaft and began stroking him as she leaned down to suck on one of his nipples. A few minutes of this and the boy was asking for mercy. She giggled and got up off the bed. Lucy was still a little worried about exposing her fifty-something year-old wobbly bits to the boy so she switched off the light and, in the sudden blackness, he heard her taking off her tights and bra and then rummaging in a drawer. She climbed up on the bed and he felt an expert set of fingers roll a condom down his iron-hard cock. His eyes adjusted to the darkness. He could see her naked body as she lay on top of him. Her breasts squashed against him. He could make out her dark bush between her legs as she lifted her leg over him. Then his brains exploded.