Jessie and James

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Another erotic story from the FLOGMASTER!

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Jessie and James

(****, m/f, Intense, spanking)

A sweet tale about a childhood spanking relationship that blossoms into true love. (Approximately 5,170 words. Originally published 2007-10.)

"Would you spank me?"

The question startled -- no, shocked -- the sixteen-year-old boy. The little girl was ten years his junior, the neighbor's brat. Her name was, uh, Jessie, that was it. He looked at her now. She was a cute little thing, with blonde hair and big blue eyes and tiny white teeth bursting from a friendly grin. It was nearly ninety out and she wore a tiny two-piece bathing suit and James could see a faint sheen of sweat on her upper arms. The suit didn't conceal much, not that there was much that needed concealing. She was much too young for breasts but she did have a cute chubby bottom. A bottom that she was showing him now, offering him.

"Let me get this straight," said James, trying not to laugh. "You're asking me to spank you?"

"Yes sir," said the girl solemnly. "Usually my Daddy does but he's in Tornado."

"Tornado? Oh, you mean Toronto. In Canada."

"Yeah. So will you do it?"

"I still don't understand. Spankings hurt. Why would you want to be spanked?"

Jessie giggled. "I didn't say I *wanted* to be spanked, silly. I asked if you would!"

"So you're just testing me? You don't want me to actually spank you."

"No, I do want you to spank me. I've been naughty and I need to be punished."

"So you DO want to be spanked!"

The girl looked horrified. "No, of course not! Spankings hurt, you dumb-ass!"

James frowned. "Where'd you hear language like that?"

"On TV."

"You shouldn't watch programs where they talk like that."

"Well? Are you going to do it?"

"Spank you? Of course not. Don't be ridiculous."

"Why not? I've been bad!"

"What did you do?"

"Well, today I let Mr. Rover's dog out and he dug up Mrs. Davis' flowers. Then I put salt in the sugar container so Mrs. Waldrop would get salt in her coffee!"

"Who's Mrs. Waldrop?"

"My babysitter."

"Then why don't you ask her to spank you?"

Jessie pouted and stamped her foot. "Because I want YOU to do it! You're much nicer than mean old Mrs. Waldrop."

"You don't even know me. We've never even spoken."

"I see you all the time. You wave at me when you ride your bike by."

"That doesn't mean you know me. I could be a mean guy."

Jessie shook her head firmly. "Nope. You're nice. You're dreamy. I love you."

"What?" James laughed. "You're nuts."

"We're going to get married," said Jessie in the same no-nonsense voice.

"Really. How old are you?"

"Almost seven."

"And I'm sixteen. I'm like, ten years older than you."


"So when I'm like twenty, you'll still be a little girl."

"When you're thirty I'll be twenty. That's when we'll get married."

"So I have to wait until I'm 30 to get married?"

"Yup." The girl spoke with such finality, James didn't know what to say. He wanted to laugh, but she was so serious that he sensed that would hurt her feelings. So he said nothing. Finally, after a lull, Jessie said, "So? Are you going to?"

"Going to what?"

"Spank me!" she cried with an exaggerated sigh and shaking her head as though James was an idiot.

"Oh." He reached out and smoothed down the wildly curly hair on her head. "You're a funny kid."

Growling with frustration, the little girl pulled down her swimsuit bottoms and leaned across James' lap. "Now make sure it's a good one," she said firmly. "It's got to be hard or it doesn't count."

"You're crazy!" But the girl was crawling across his lap and James was suddenly entranced by the round buttcheeks bared before him. The bottom was tiny -- surely his palm would fully cover both cheeks -- but it was deliciously chubby and he couldn't help but realize that he was becoming aroused. This horrified him, but then was sixteen and glimpsing 81-year-old Grandma Sue coming out of the shower had given him a woody, so he was pretty used to such happenings.

"Look, I can't spank you," he said, his hand really wanting to palm that cute butt. "I'd get in trouble."

"No one will know," said Jessie. "I won't tell."

James felt his resistance weakening. The lure of that bottom was mesmerizing. "This doesn't make any sense," he muttered.

"Of course it does. I was bad, now I get spanked. Simple. How many will you give me for the dog?"


"How many spanks? For letting the dog out?"

"Uh, I don't know. What's fair?"

"You can't ask me, I'm the naughty one!"

"Well, what does your dad usually give you?"

Jessie frowned in thought. "I dunno... it depends on his mood, I guess. Maybe twenty or thirty? It depends on what I did. For really naughty things it's much more."

"Is letting out Mr. Rover's dog really naughty?"

"Oh yes!" giggled Jessie. "I've been spanked for doing that before. Daddy calls that a 'repeat offense' and spanks me double."

James gulped. "So that's like sixty spanks, then."

"Yup," said the girl, unconcerned. "And then there's the salt thing. That's REALLY naughty."

"That was pretty mean."

"You should have seen Mrs. Waldrop's face when she drank her coffee! She looked like she'd just swallowed medicine!"

"So another sixty for that?"


"You really want me to do this?"

"Yes, please. I won't feel good unless I'm punished for my naughtiness."

James couldn't believe he was actually thinking of doing this, but there was something so compelling about it that he almost felt like he wasn't making any decision at all but merely obeying someone else. Besides, the brat was practically begging him. What was he supposed to do, refuse?

Then he realized his hand was on her butt. He could feel the smooth silkiness of her skin, the young flesh unblemished and perfect. She wiggled slightly, getting into a better position across his lap, and his body reacted to the quivering buns in his palm. His sudden erection was almost painful.

He raised his palm and brought it down with a gentle pat. Jessie giggled. "That didn't hurt at all!"

"I'm just getting started." He spanked her a little bit harder, and then a bit harder yet.

"Ah! Ouch! That's better," she said. She nodded as he spanked her again.

Her skin bore only the faintest pink blotch where his hand had struck, giving him confidence that he wasn't truly hurting her. He spanked her again and again, harder and faster, sometimes alternating between cheeks just to see them bounce independently.

Jessie cooed and sighed, wiggling playfully across his legs. "Ow, oooh, ahhhh!"

She didn't seem in any particular distress and so he continued the spanking, picking up the pace and striking her rump with increasing force. Three to the left cheek, Slap! Slap! Slap! Three to the right, Slap! Slap! Slap!

This was kinda fun, he thought. It made no sense at all -- in his mind spankings were horrible events of violence and pain -- but the girl wasn't bothered and he was certainly entertained by her reddening bottom shuddering under his smacking palm.

Finally, after what seemed like a long time, James paused. Jessie's buttocks were glowing a hot pink and he could feel the heat radiating from the punished flesh.

"How many is that?" panted Jessie.


She rolled her eyes. "How many spanks?"

"Uh, I don't know. I forgot to count!"

She sighed. "You are new at this, aren't you."

"I've never spanked anyone before, if that's what you mean."

"You just need practice. I'll come back tomorrow and we can do it again."


"Give me a few more to finish up. Make them really hard and fast!"

Again it was as though he had no control over his actions: James simply obeyed. He spanked that bottom really hard. Not as hard as he could -- Jessie was a little girl -- but harder than he thought she'd like. She yelped and wiggled and "ouched" a few times but did not scream or try to run away. He counted out twenty hard slaps and stopped, rolling her off his lap.

"There! Are you happy now?"

"Yes sir, thank you sir!"

Little Jessie turned away, showing him her tomato bottom, and carefully pulled up her swimsuit. "That was a pretty good spanking," she said. "Not as hard as Daddy, but then he really knows how to spank. You'll learn."

And then she was gone, scampering off who knows where, leaving James aroused, nervous, and bewildered. After a few minutes he wondered if he'd imagined the whole thing, it seemed so unreal, and yet his hand was throbbing and was a bit red. He went inside the house to the bathroom and locked the door. Quickly he undid his pants and brought out his raging hard-on. He hardly had to pump at all as he spurted within seconds. It felt so good and he couldn't get the image of Jessie's plump little red bottom out of his head.

The next afternoon, she showed up again. James was in the hammock reading the new "Hellcat" he'd bought that morning.

"I'm ready for my spanking!" she announced, appearing out of thin air.

"What?" James tried to sit up and almost fell out of the hammock. "Shhh! My mom's home!"


"So she can't see you here... us..."

"Why not?"

"Because... because she can't, that's all. I'd get in trouble."

"Would you get spanked?"

James glared at her. "No, I would not get spanked! I'm sixteen. I'd get grounded."

"What's that?"

"No TV for a week, no going out. Stuff like that."

"A whole week? I'd rather get spanked and have it over with."

"Yeah? Well most people aren't like you. They think spankings are awful."


"Because they hurt. And they're embarrassing."

"But spankings are supposed to hurt. That's so you won't want another one."

"Exactly. Most people don't want another one. But you... I can't believe you're back. Didn't you get enough spanking yesterday?"

Jessie shook her head. "You didn't spank me very hard. You need practice. And today I was naughty again."

James almost smiled. "What did you do now?"

"I put Geeby in the fish tank."

"Who's Geeby?"

"My cat."

"Uh. That didn't go well, did it."

Jessie giggled and shook her head. "Geeby didn't like it at all. He hopped out of the tank, getting water everywhere. And he ate Peebers."

"Peebers is the fish?"


"So what did Mrs. Waldrop say?"

"She said I ought to be spanked!"

"But she didn't do it?"

"No. She's too old."

"She's going to tell your mother, then, and you'll get spanked tonight."

Jessie shook her head. Something about her seemed almost forlorn. "No, Mommy doesn't spank. She's too tired after working all day. She just yells at me and locks me in my room."

"That's terrible."

"Yeah. It's much worse than a spanking. Daddy always hugged me and held me after a spanking." Tears glittered in Jessie's eyes. "I miss my Daddy."

"Oh. But he's coming back, right? You said he was in Toronto?"

"Yeah." Suddenly she brightened. "But you can spank me until Daddy comes home!"

"No, I can't do that." James looked toward the house as though it might be watching. "I'll get in trouble."

"Oh. Your mom. She doesn't like spankings."

"It's... more complicated than that. But, yeah."

"I know! We can go somewhere else. Where your mom won't see us!"


"My treehouse."

"You have a treehouse?"

"Yeah, Daddy built it for me. It's really cool. Come on."

The next thing James knew Hellcat number 14 was abandoned on the hammock and he was following the girl through the fence.

Though the Venderly's house was near the main road, they were the last house on the block and owned considerable property. Their backyard was huge and beautifully landscaped with a forest of flowers and a small grove of fruit trees near the back. Near these was a giant oak that towered over everything. It was at least a couple hundred yards from the house and the trees in between meant there was no direct line of sight. There were no neighbors this far back either. It was perfect seclusion. James began to feel tempted. Who would find them out here?

The treehouse was surprisingly spacious: a nice ten by twelve room built in the crotch of the oak about fifteen feet up. A sturdy wooden ladder was built into the trunk of the tree making it easy to climb up. There was even a deck with safety rails where you could hang out when it was too hot and stuff to be inside the room.

"Your dad built this? This is really cool."

Jessie grinned. "Come inside, I've got lots of neat stuff inside."

The ceiling was not tall at six feet, but James could easily stand without hitting his head. Inside the walls were covered with Disney posters, Hillary Duff, Hannah Montana. There was a small set of chairs and a table in one corner, and an old cooler. A cabinet was on one wall, its door open revealing plates and cups. There was a wooden toy chest which Jessie ran to open, pulling out stuffed animals and blankets and books and other items.

"See, I've got coloring books, games, books, all kinds of stuff. I keep it here so Mrs. Waldrop doesn't get into it."

James was still in awe of the construction. The place felt more solid than his parent's home. "Does your dad work in construction?"

"Yeah. He builds homes and shopping centers and stuff."

"That's explains it. This is really nice."

"Ah, there it is!" Triumphantly Jessie held up a white plastic hairbrush.

"You found your hairbrush."

"Yup. Now you can spank me." She handed the brush to an astonished James and proceeded to take down the miniature jeans she was wearing. She took them completely off, standing only in tiny white panties and T-Shirt and socks. "Come over here. There's more room."

James found himself sitting on the toy trunk, the little girl at his side. She pulled down her panties and climbed onto his lap. "Okay. Start with your hand and then use the hairbrush."

"You mean I'm supposed to spank you with this?" He looked at the thing and realized that the back of the brush was quite smooth, like a little paddle.

"Yeah. What did you think it was for?"

"I thought-- never mind. You know, a spanking with a brush like this could really hurt."

"Good. That's what I need. I told you, I've been naughty."

A tiny part of James wanted to argue, to protest, but a much larger part, a growing part, was staring at the plump bare bottom before him and itching to get started. There was no trace of yesterday's spanking. The cheeks were smooth and unblemished. He reached out and caressed the silky skin, emotions stirring within him.

Smack! Slap! Whap! He began to spank her, and spank her soundly. He was familiar with this now and knew what worked and what didn't. He had less fear of actually hurting her now and so he spanked without hesitation.

After a few dozen hand spanks, he paused, admiring her ruddy bottom, and then he picked up the hairbrush. He brought it down almost as hard as some of the spanks he'd been administering and suddenly Jessie let out an anguished scream.

"Owwwwww!" She writhed on his lap, sobbing miserably.

"Oh! I'm sorry!" he gasped, realizing the hairbrush really stung. "Are you okay?" He rubbed the bottom vigorously.

"Owww. That really stung," moaned Jessie. She sniffed and wiped tears from her face. "I'm sorry I yelled. I didn't know that brush could hurt so much!"

"You're okay?"

"I'm fine. I was just surprised, that's all. Go on. Finish the spanking."

"Are you sure?"


"I'm not using this hairbrush any more."

"Oh but you have to!" cried the girl. "I've been very naughty. I'm supposed to get the hairbrush when I've been naughty."

"You really want me to use the hairbrush?"

"Yeah, but not so hard."

"Okay, if you're sure."

"It's okay. I deserve it. I'm a bad girl."

James started spanking Jessie again with the hairbrush. This time he was much more gentle, starting off with mild pats and slowly getting to real swats. He gave her ten solid spanks to each cheek with the brush and stopped.

"I think that's good."

"Thank you for spanking me," said Jessie softly, wiping her face off on her shirt.

"You're welcome, I guess."

"You still need practice, though. Come here at this time tomorrow and we'll make it a bit harder spanking."

"Another one?" James couldn't believe the girl, but his heart was pounding with excitement and he didn't really care about her motivations. If she wanted him here to spank her tomorrow, he'd be here!

* * * * *

Over the rest of that summer, James spanked Jessie all the time. Not every single day, but most days, certainly. It became a regular thing. They didn't even talk about it, much. There was no need. Often Jessie would be naked in the corner waiting for him, the hairbrush on the little table. After a while, James stopped questioning it. It was just this thing they did, it happened, and no one needed to know and it wasn't weird or odd or unusual.

When school started, James didn't have as much time for Jessie, but they still continued whatever it was they were doing whenever he had the chance. Two or three times a week he'd slip out of the house and go to the treehouse. He'd spank Jessie until her bottom was scarlet.

This continued for years. Jessie grew into an adorable ten-year-old, her body showing hints of blossoming womanhood. She was going to be a heart-breaker. She still needed spanking, though, and James was happy to oblige.

It wasn't until the next summer that he realized her father still hadn't come home. He never spoke to her about it, but he brought it up at dinner one night at home, trying to make it some casual rumor he'd heard at school, and his mom confirmed that Mr. Venderly had left his family. James was horrified. "But why? he asked.

His mother shrugged. "I've no idea. The story I heard was that he just got up and left one day. Moved to Canada, I think. Horrible. Left behind a little girl. Such a sweet thing. Very polite. You know she helped me bring in the groceries the other day?"

"Oh yeah?"

"Very nice of her. So sad about her father."

James was deeply trouble by this news. Jessie talked about her dad all the time, but she always spoke about him as though he was returning soon.

As the years went by, James didn't think about Jessie's father as much and she didn't mention him as often either. They talked about other things. James found her a surprisingly good listener. He would tell her what he was doing in school, any problems he was having, and she would listen and ooh and ahh.

He found he really liked talking with her. She was cute and funny and did whatever he said. When he ordered her to bring him the hairbrush she did. When he said her spankings needed to be with her totally naked, she agreed. When he suggested that he spank her with his leather belt, she agreed.

By the time she was ten, Jessie could take amazingly hard spankings. He'd always spank her with his hand initially, mostly because he enjoyed the physical contact of his hand on her ass. But hand spankings weren't enough for either of them and so spankings always included at least a dose of the hairbrush, wooden paddle, or belt. James had discovered switches, too, thin branches from the nearby fruit trees, and these left thin welts across Jessie's bottom and thighs and stung like bees. She did not like switchings at all, but she still obeyed whenever he ordered her to fetch one. Her eyes would grow sad and she'd bit her lower lip and reluctantly climb down from the treehouse and return a few minutes later with a switch.

James knew he enjoyed spanking Jessie. He did not know why, exactly. He assumed it was somehow sexual, though there was never anything overtly sexual between them. Early on this had bothered him a bit, but over the years he just accepted it. It was just something he and Jessie did, that was all. She seemed to derive some comfort from it (he wasn't sure if it was pleasure, exactly) and he made no secret that he enjoyed it.

Then James went off to college. It was a sad time for Jessie, but James had had less time for her lately and she had learned to take advantage of whatever time she could get.

When he came home for Christmas, he saw her regularly, and it was almost like old times. It was cold up in the treehouse, but Jessie would bravely strip for her whippings and was soon plenty warm, at least in a certain area of her anatomy.

The next summer James had gotten a job in town and wasn't around much. She saw him a few times, and he commented at her developing body as he spanked her, but he also talked about his new girlfriend. Her name was Sarah and she was 19 and "smokin' hot."

As the years went by, contact between the two faded. James had his own life. He graduated with a degree in marketing, got a job in Chicago, and married a journalist named Karen. They divorced after two years. Jessie heard about it from James' parents. Jessie was fifteen at the time and her heart ached for James.

She saw him, once, at Christmas, the year she was sixteen. She'd developed into quite a stunning young woman. Guys at school were all over her, but though she was polite and dated frequently, she did not encourage any of them. Her heart was elsewhere.

The Harper's were having a Christmas party and she'd been invited. She hadn't expected James to be there -- she'd heard he was working and wouldn't make it. But suddenly as she came out of the bathroom he was there, spilling his drink he was so surprised.

"My God, is that you, Jessie?"

"James! You made it! Your mom said--"

"Well, I wasn't going to come. I just started working for this new tech startup, you heard about that? Great opportunity, and I'm in on the ground floor, but they got me burning the candle at both ends. So I'm only here for the night. I fly back tomorrow morning."

"Oh." Jessie felt a sharp pang of disappointment, but she nodded bravely. "Work is going well, though?"

"If you like chaos and missed deadlines and ninety-hour weeks, it is."

Jessie laughed and saw James watching her closely. He was impressed at her beauty, she knew. She was all grown up now, with a woman's body. Still petite, still cute, but with a lot more curves. Her ass was still fantastic, though a lot larger than the last time James had seen it. He openly gawked at it, then broke off when his mom came up the hallway saying, "Oh James, I see you're talking with Jessie. You remember Jessie, don't you? The girl next door? She's growing up, isn't she? So lovely!"

"Er, yeah, mom, she's lovely." He gave Jessie a weak smile of helplessness, and then the two were dragged off to sing Christmas carols with the others. They caught each other's eyes a few times that evening, but never could find time alone. Then James was gone, back to Chicago, back to his new life.

Jessie graduated from high school and headed off to college. She'd heard James had moved to California. The company he was with was doing well, apparently. They'd merged with another firm. But she wasn't sure where he was. His parents had retired and moved to Arizona, so her main source of information was gone.

One day she looked him up on the Internet and found his bio on the Zinkster corporate website. The company was in Fremont and it said James lived in Palo Alto. No mention of a family. There was an email address, though, so she fired off a letter.

"Hi James. It's Jessie Venderly. I'm sure you remember me from when we were kids. I'm all grown up now. I'm in college. I don't have a major yet as I don't know what I want to do. I would like to see you, if you're interested. Perhaps I could come out to California sometime?"

She attached a recent photo of herself and fired it off with a beating heart. All afternoon she worried and wondered. The more time without a reply the more nervous she got, but the next morning when she checked her account, there it was.

"Jessie! So good to hear from you. I trust you are doing well. You look wonderful. The little girl next door has all grown up! I would love to see. If you're out California way, please be sure to visit. I've got a big house so there's plenty of room if you'd like to stay. I was involved with a woman for the last year or so but we broke it off and now I'm alone in this big house. Please tell me you'll come. I'm enclosing a Southwest Airlines voucher for your trip. It's good any time in the next year. Just let me know when you'll come!"

Jessie could hardly believe it. She was so excited. James had included his cell phone number so that evening she gave him a call. He answered on the second ring.

"James? It's Jessie."

"I see you got my email."

"Yes. Thank you for the plane ticket. It was very generous of you."

"It was nothing."

Jessie frowned. There was something odd in James' voice. He sounded distant, aloof. Or maybe it was cautious. He wasn't his usual warm self. "Is something wrong, James?"

He let out a heavy sign. "Jessie, there's something I've got to get off my chest. Back when we were kids..."


"Well, uh... I did some things. Things I'm not proud of."

"What are you talking about?"

"To you, Jessie. I did things to you. I want to apologize."

"You have nothing to apologize for, James. You did nothing wrong."

"I took advantage of you."

"You did not."

"You were a little girl. I had no right."

"You did exactly what I wanted you to do, James. You were a complete gentleman, too."

"I didn't feel like a gentleman."

"Well you were." Jessie's voice was as firm as she could make it. "Think about it, James. You were sixteen. What kind of sixteen-year-old boy would spank a girl's bare bottom and do nothing else? You were a gentleman. You gave me exactly what I needed and nothing more."

There was a long silence. "I see." He did not sound convinced. "You don't hate me?"

"Hate you? James, I adore you!"

"That was just a little girl's crush. You don't even know me."

"Of course I know you, James. I know you better than anyone. All those hours in the treehouse... of course I know you. And you know me."

"You can't seriously think you're in love with me."

"Why not? Just because I'm younger than you? I've loved you for years, dear James. At first, yes, it was a schoolgirl crush. And later, it was something else. But as the years went on I knew. You and I are linked. It's not temporary."

"I'm almost thirty. I'm getting old."

Jessie laughed. "Thirty's not old! I'm only eighteen and even I know that. Besides, you're not thirty, you're twenty-eight."

"Almost twenty-nine. You'll be nineteen soon."

"Age doesn't matter. I want to see you."

"When can you come?"

"I can be there this weekend, if you want."

"I do."

He picked her up at the airport. He looked good, fit from regular handball sessions and bicycling. She was a dream, shapely and feminine with the face of a goddess. They melted into each other's arms like two halves of a whole.

"God, you don't know how many times I thought of you over the years," said James as they walked to his car. "But I felt guilty. I thought I'd hurt you. I figured you must either hate me or have grown up into a really fucked up young woman."

"Because you spanked me?"

James' blush was deep. "Well, yeah. I mean, that was some messed up shit, wasn't it?"

Jessie put her hands on either side of James' face and held him, forcing him to look into her eyes. "Why do you think I'm here, James?"

He stared at her in astonishment. "You aren't serious!"

"Never more. You've neglected me for years, dear James, and I intend to be as sore as can be on that flight home!"

"You *want* me to spank you!"

"Don't you want to spank me?"

James' voice was rough with desire. "Yes. yes I do."

"Then what's the problem? Do I have to do something naughty to get you to put me over your knee?"

He kissed her then, right there in the parking garage. His hand found her ass and gave the mound a hard squeeze. "These gorgeous buns are going to burn," he hissed.

"I sure hope so," smiled Jessie. "Do you have a paddle?"

"Damn it, I don't!"

She giggled. "Don't worry. I've brought some things in my suitcase."

James shook his head. "You think of everything."

"Of course. If I'd left it up to you we never would have even met!"

They both laughed at that, James shaking his finger warningly at her. "You are a naughty minx. You played me from the beginning, didn't you. Six years old and already pulling my strings!"

Jessie's eyes twinkled. "Guilty as charged. I guess you'll just have to spank it out of me."

He patted her rump as he opened the passenger door for her. "That, I can promise you, I will do."

Jessie shivered slightly at the stern tone in his voice. "Will it be hard?" she asked softly.

"Extremely hard. Severe."

She sighed. "Then get in the car and let's hurry up and get started!"

As the Porsche roared up the freeway she looked around at the Bay Area traffic, the surrounding mountains, and the setting sun and sighed happily. "I think I'm going to like living in California."

His eyes flashed over to her and she laughed gaily. "A long time ago I told you I would merry you, James W. Harper. You just didn't believe me."

"I was a fool."


"Oh, you're gonna pay for that."

"I hope so," she said with a so-huge-you-can't-wipe-it-off grin. "I hope so."

The End

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