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The Lucky Paperboy

"18 year old Harrison is about to become the luckiest paperboy in the world, Kim fresh from her break up with Matt agrees to a date."

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2.5k words 2.5k words

Author's Notes

"Continuation from repaying the debt."

What an invitation

Harrison cycled the familiar streets, never varying in the last five years his route. He still enjoyed delivering the papers even at eighteen, the round had allowed him to save for college and he would genuinely miss the customers. especially the Roger's house.

Of all his stops, he enjoyed delivering to one particular house: the couple were not only good tippers but Mrs Rogers usually paid and she was incredibly hot. In her late twenties with long blonde hair, she had a great figure and no matter what she wore, she looked great.

She was, indeed, a teenage boy’s fantasy, and although it was always just a short polite exchange, he loved the contact with her.

Propping his bike against the wall, Harrison reached into his bag and pulled the paper out before killing the music blasting from his earphones. He wouldn’t allow anything to deflect his concentration in the next few minutes.

About to step onto the porch, Harrison was startled by the sudden appearance of Mr Rogers. Quickly recovering composure, he said, “Hi, Mr Rogers…paper money.”

“Ah, young Mr Harrison. Thursday already is it?”

The boy smiled at him but he was really wishing his wife would come to the door. “If you’re going out, I can always ring the bell for Mrs Rogers.”

Instantly, he worried that he might have offended the man but Mr Rogers simply smiled and asked, “Would you rather Kim paid you?”

“No, it’s not… I mean, I was only—”

“It’s okay, Harrison.” Mr Rogers smiled knowingly. “Yes, I know Kimberly is very attractive but I’m going to tell you something.” He looked over his shoulder at the door and back at the young man. “We’ve separated. I’m leaving her for her sister, Jess.”

Mr Rogers pointed to the red sports car across the road. “That’s her sister’s car.”

At that moment, Jess came out, carrying a bag. Harrison assumed it was Mrs Rogers’ sister as she looked like her, a little slimmer and, if possible, prettier. She definitely had a bigger bust and dressed with more style. 

As she stepped past Matt and Harrison, Jess slapped her bum and the boy giggled.

“She’s a little hottie, isn’t she Harrison?”

“Matt,” admonished Jess and stared at him. “Right…well, I see I’m not going to get much help from you today. Maybe I should take you on holiday with me, young man, but I guess your mum would come looking for such a sweet young thing.”

“I’m going to college in a few weeks,” said Harrison lamely as Jess resumed walking toward her car.

“I’m starting the engine, honey. Please don’t be long, the airplane won’t wait, not even for a handsome man like you.”

“College, eh? you have grown to a responsible young man”

“Yes, Mr Rogers, three more weeks and I give this paper run to my little brother and I start my studies.”

“Good for you.”

The boy handed the paper to Matt and waited.

 “Ah, the money. Well, as I said, Kim is single now so how would you feel about her owing you something? She can be very accommodating.”

 Harrison frowned. “I’m not sure what you mean.”

“Oh, I think you do know what I’m talking about.”

 The boy blushed.

“Matt,” Jess called, leaning out of the car window. “Hurry up. If you’re not here soon, I’ll need to use the gear stick.” She laughed and ducked back inside the car.

“I’ve got to go, son,” Matt said and tucked the paper under his arm. “Go in and tell her she owes the money. Look, I promise you, you’ll know what to do.”

Matt jogged down the path to the car but waved for Harrison to go inside the house before he got in the car. They drove off as Harrison walked to the door and pushed it open.

“Hello,” he said through the open doorway but didn’t receive an answer. “Hello,” he repeated and thought he heard movement. He stepped into the hall and peered into the living room. Empty. “Hello, Mrs Rogers, are you here?”

 “I’m up here… can you give me a hand?”

Harrison climbed the stairs and entered the first bedroom. Wearing a light blue housecoat, Mrs Rogers was leaning over and pushing down on a bulging suitcase. He watched as her chest bounced as she tried to close the lid.

“Mrs Rogers.”

“No, not any more,” she gasped with her exertions. “I’m just Kimberly now.”

“I need the paper money, Mrs Rogers.”

“I told you, it’s Kimberly.”

“Okay, sorry. Err, paper money, Kimberly.”

She stopped pushing on the suitcase. “Didn’t Matt leave money for you?”

“No.” He shook his head, then added, “He said I was to see you for the money, said you can be very accommodating.”

“Hmm, did he? Well, yes I can,” she said, turning and smiling at the boy. He felt out of his depth in this hot woman’s bedroom. “So, Harrison isn’t it? You can call me Kim.”

The boy nodded, unable to move and unsure what to do.

“How about you give me a hand with this?”

“Oh, sure.”

Kim slowly sat on the case, her legs spread on either side of the fasteners but holding the edge of the housecoat to cover her modesty. Her bare legs were smooth and toned.

“Come on, help me fasten it.”

Harrison moved closer and nervously reached down. With her weight on the case, he was able to effortlessly clip it shut. His gaze returned to her bare legs again before she lifted his hands off the clips.

“Good boy.” She smiled again. “Can you manage to carry it downstairs for me?”

He nodded, feeling his mouth too dry to speak, and struggled with the case down the stairs to the hall. He left it beside the front door.

Standing straight and taking a deep breath, he said, “There, all ready for you. Are you going on holiday with your sister?”

“Oh no.” Kim shook her head, standing at the bottom of the stairs. “I’m moving back to my parents' house. My sister and Matt are selling this place and buying somewhere new.”

“Oh, I see.”

Kim’s housecoat had slipped open and only the loosely tied belt stopped it from being fully agape. “Thanks for your help,” she said.

 “No problem,” he managed and gulped. “So, my paper money?”

“Oh, right.” She walked around him, brushing a hand along his chest and a white t-shirt. “Such a strong boy. Tell me, Harrison have you ever been with a girl?”

He was taken aback. Significantly smaller than his younger brother, he’d never been told he was strong and he’d never been good at sports. In fact, he’d always been shy and timid.

“No,” he croaked and coughed, trying to clear his throat.

 “No girlfriend?”

He swallowed hard. “No”

 “Would you like one?” Kim was now back in front of him and very close. She whispered into his ear, “Would you like me to show you how to get a woman and make her happy?”

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The nervous eighteen year old bobbed his head.

“Well, you see, I thought we could do an exchange.”

“Yes, Mrs Rogers.”

“No, no…it’s Kim,” she said, “don’t forget that. So, what terms should we barter, Harrison baby?”

“Like, what do I want?”

 “Oh, you’re direct, aren’t you? And I thought you were going to be nervous and bashful.”

 “I meant as in what you… I mean, err, oh, I don’t know—”

 “Easy there. Just tell me what you want to pay off the debt.”

 “Anything?” he cautiously asked.

“Anything,” she purred.

 “Would you go out with me?” The question came out as nothing louder than a timid whisper.

“Where?”

 “Like on a date, something to eat, a movie.”

 “I like that idea, but there’s one problem… I don’t have any money.”

 “I’ll pay,” he said quickly. “I have a little saved and I would love to take you out.”

“Deal.”

Kim offered her hand and they shook before she pulled him in for a quick kiss on the lips. 

Amazed by the kiss, he recovered to tell Kim about a pizza place and a new movie he wanted to see. She agreed that it sounded like a great night.

“What should I wear?”

 “Well, lots of my school will be about so I was—”

“You want me to dress sexy for you?”

He thought his head would drop off if he nodded any more.

 “Okay, so you will come back for me later?” she asked, walking him to the door. He backed up while looking at her and clumsily bumped into a wall unit, then against the door.

 “Harrison, it’s not going to work if you’re so nervous. How can you pass us off as on a date if you’re acting so jumpy?”

Swiftly, she pulled open her housecoat and placed his hands on her breasts. His hands were cold and he trembled as he felt her warm orbs. “Don’t be shy, give them a squeeze.”

He did — and his touch became firmer and he literally warmed to the job in hand before Kim wrapped the grown around her naked body.

 “Okay, that’s better. So, I will see you soon.”

 He nodded again and left.

~~~~~~~~

Harrison rang the bell and Kim immediately opened the door. “Don’t you look handsome?” she said in greeting.

As she walked back along the hall, he saw she wore a long grey top with a black belt and her tight black leggings looked great against shiny black heels. She picked up a bag. “Are you ready?”

“Sure.”

She drove them to the pizza place but Harrison was disappointed because he didn’t recognise anyone in there. Damn, no one was there to see him with his gorgeous date. After eating, Harrison duly paid and they left for the cinema.

In the queue for tickets, she stood next to him and several guys checked her out. Harrison sensed she liked the attention. He also noticed a few girls from school were further up the line and he wondered which movie they were going to watch. But they were too far away to find out.

 Once at the front, he stepped forward to the desk and Kim took his arm.

“Two tickets for hall three, please.” 

“We have the back, or middle centre.”

“Back row, please,” said Kim.

“I have right or left. Sorry, centre is taken.”

 “Right.”

Harrison paid and they walked to the confectionary area where several groups of kids around Harrison’s age stood making their choices.

 Kim turned to him and asked, “Please can we get popcorn? Please, please, please.”

Harrison watched a couple in their mid-twenties turn around to look at them, obviously surprised to hear a woman asking a boy if she could have popcorn.

“Yeah, whatever you want.”

 “Goodie.” She clapped her hands, drawing more attention before she took a coke and large popcorn. Harrison paid and they managed to get into their seats and settle down as the opening trailer began.

Harrison noticed three girls from his school sitting just along from him. He sat back to watch the trailers and Kim seemed content with her popcorn. After several moments, he thought the girls had recognised him as they whispered to each other.

He leaned into Kim’s ear. “Those girls that keep looking over are in my school. Obviously, they don’t understand why you came here with me?”

Kim shoved more popcorn into her mouth, leaned forward, and looked beyond him to the girls. They quickly looked back to the screen.

Still leaning forward, Kim waited till all three looked over again. She made sure they could see her moving towards Harrison and her eyes met his right before she kissed him. She wrapped an arm around him and slipped her tongue into his mouth. She got zero response — other than a bulge in his jeans.

She glanced at the girls before relaxing back in her seat. The girls resumed whispering. Obviously, they’d had different opinions about who she was — maybe his older sister, a friend — but Kim had provided a stunning solution to their puzzle.

She took another handful of popcorn and shifted in her seat as the lights dimmed further. Moving her thin jacket from her lap onto his lap, she slid her hand over the armrest and under the garment, slowly edging across until she was on his bulge. She rubbed him through his jeans and his cock responded in magnificent fashion.

“Undo your jeans,” she whispered before running her tongue around his ear lobe as the movie began.

Under her jacket, he slowly fidgeted until his cock was out and she immediately started to slowly wank him. He shuddered and nervously glanced at the girls who were now watching the movie.

Kim continued to stroke his rigid shaft and very soon he turned to her. “I’m going to cum,” he panted.

“Go on, cum, let it go.”

He surged and released his seed, holding his breath, trying not to make a noise. She held him, feeling his cream run over her fingers until he gradually deflated. She then wiped him against the inside of her jacket, cleaning him off.

As he reached down to button up, Kim raised her hand to her mouth and licked the cum from her fingers. She popped more popcorn into her mouth, enjoying the mixture.

“After tonight the debt is paid, okay?”

Harrison nodded, handing back her jacket. “Sorry about the mess.” 

“It's okay,” she muttered and licked what she could from it between mouthfuls of popcorn.

He leaned towards her. “Can we go to your house after this?”

 She looked at him, preparing to say “No.”

“We could call it an advance on next week’s papers,” he said quickly. “I mean, you’re supposed to give me a week’s notice to cancel so, technically, it’s still a debt.”

 Suddenly she felt like agreeing. “Sure, but if I take you home, that’s the debt cancelled. Okay?”

“Hmm, well…” He sat back. “I suggest we go back to your place to discuss the full repayment of the debt. That would be just a part of it.”

 She went back to watching the movie unable to voice an objection.

Published 
Written by Fiona69m
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