Jane Pays It Forward

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Jane is encouraged to educate a young man.
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Tim heard the side gate squeal open, and checked his phone: 12:30 on the dot. Jacob was punctual, he'd give him that. He was other things too: polite, helpful, pleasant to be around. He was also a virgin. How did Tim know? Everyone knew.

Tim nodded to Jacob's wave, and watched the kid drop his habitual towel and water bottle on a chair and walk to the pool. With hardly any hesitation, he dove into the deep end. Perfect form, nary a ripple, as the kid's smooth form split the water. Upon surfacing, he began to swim laps.

The young man came to use their pool to practice swimming but Tim suspected just as much time had been spent floating as swimming recently. He didn't care; the pool privileges Jacob used were provided in exchange for maintenance and cleaning, and it meant Tim could do more relaxing.

The sun was beating down that day, and Tim was content to stay out of the water, under an umbrella, with a drink in his hand. His wife, Jane, was keeping him hydrated with a steady stream of daiquiris and margaritas, resulting in Tim feeling a bit wobbly. A perfect Saturday.

After a half hour of laps, Jacob swam to the edge and clung there, not even out of breath. Tim felt a flash of envy. He'd been an athlete in school, so knew how well the body could maintain performance, but he hadn't had that level of fitness in decades. He wasn't out of shape now, but he wasn't in shape either. There was a spare tire starting to gather on his middle now that he'd hit 40.

Tim was comfortable not filling the air with meaningless talk - a trait he recognized in Jacob - and so neither of them spoke. He watched the 18-year-old kid floating in his pool from behind sunglasses, waiting for the inevitable.

When it came, it was obvious. Jacob's eyes suddenly locked on something behind Tim, and didn't waver until it was revealed to be the form of Jane, as she brought out a plate of snacks. She was wearing a modest bikini to cover her shapely form, under a short robe that came down to her thighs. Any other husband might wonder if his wife was putting on a show, with her sexily swaying hips and bright smile, but he knew there was no show. It was just how Jane was. He watched appreciatively as she bent over to place the plate on the table between their two loungers, her cleavage bulging as her impressive tits pressed up in her top. The movement caused her golden ponytail to flip over her shoulder, dangling dangerously near his drink.

"Thanks, Hon," he said, grabbing a strawberry from the plate.

"Of course. I'll be back with more drinks in a bit, I'm just on the phone with Betty."

"Okay," Tim mumbled around the strawberry, watching her swaying hips retreat to the house. He quickly snapped his eyes back to Jacob, in time to watch the young man's head turn to follow Jane back in the house.

"Any luck with the girls?" Tim asked, knowing the answer. Sometimes he felt like he was deliberately being an ass.

"Nah. I get dates, but anytime I get friendly with a girl, she ghosts me. I think I might be cursed," Jacob groused.

Tim chuckled. "You'll get there. Just a matter of time, I'm sure."

"You can talk. You've got Mrs. Turner, you're the luckiest guy I've ever met."

"That I am, Jacob. That, I, am." Tim laid his head back, thinking a nap would do him some good. The drinks were starting to go to his head.

Some time later, he woke and saw that Jacob was no longer in the pool, and the snack plate was half empty. Did he go home? Tim wondered. And where was Jane with the next drink?

Standing up, feeling groggy from the nap and the alcohol, Tim made his way to the house. The blast of cool air from their air conditioning hit him like a slap in the face. Instantly awake, he took a step towards the kitchen before stopping. He'd heard laughter.

Creeping forward, he listened intently, catching a few words and then more laughter. He didn't think it was her phone call with Betty, as she never laughed like that with her friends. The other party had to be Jacob, but what were they talking about?

"Tim? You there?" Jane called out.

Tim stepped around the corner, putting a smile on his face and taking in the situation. Jane was leaning on the counter island, her robe thrown over the back of a chair. She was playing with her hair, stroking down to the point of her queue. Jacob was standing on the other side of the island, doing his best to not get caught staring at her cleavage.

"There you are," she said. "I was going to bring your drink but you were sleeping. Are you ready for it now?"

"Um, yeah. I just need to pee."

"Okay," she said, turning back to Jacob, who was blushing furiously and bent over awkwardly.

Tim padded to the bathroom, and set himself up in front of the toilet. When the stream of pee hit the water, he relaxed and picked at a nagging thought. The scene in the kitchen seemed familiar to him somehow. He searched his memory, coming up blank, until it hit him: It was almost a mirror image of him and Mrs. Johnson, 22 years ago.

It all came rushing back. His obsession with the neighbourhood MILF due to her sexy good looks and her friendly manner. Him hanging around her and her husband's place every day until one fine summer day in her pool, she gave him his first hand job. Her talented fingers had drawn out his orgasm in record time, and she'd left him twitching and spurting his cum into the water. Later on, she'd given him a blowjob, and they'd even been close to having sex until Mr. Johnson came home. Tim had had to run out the back door to avoid getting caught, and never got up the nerve to go back.

It had been his entry into the world of sex at the age of 18, and he was able to go on to get laid a week later, losing his virginity to Sandra Huggins.

Good times. He was sure that without Mrs. Johnson, he'd have languished in virgin purgatory for years. The thought sunk into his brain until it came full circle: Jacob was like him as a young man: inexperienced and naive in the ways of sex and women. The comparison sent a surge of sympathy through him.

Jacob needed an older woman to spend some time with him. Give him some experiences he'd never forget, and put him on the path to success. If only Mrs. Johnson was still around...although she'd be in her 60s by now. Someone younger, like Jane. Like Jane.

A mental image popped into his head, and suddenly Tim's dick was rock hard. He left the bathroom, doing his best to push his cock to one side to hide it. When he got to the kitchen, he found his wife alone. "Where did Jacob go?" he asked, walking up behind her. He abandoned his attempt to hide his rigid dick now that they were alone.

"He had to run suddenly," she said. "Ohh, I thought you had to go pee?" she cooed, feeling his hardness press into her ass cheeks.

"I did. I was thinking of how sexy you are, and now I'm glad Jacob left. I think we should head upstairs." He kissed her neck, thrusting into her butt suggestively.

Jane giggled and followed when he led her by the hand to their bedroom. Stripping their suits off quickly, they tumbled onto the bed. Tim had intended to take some time with foreplay, but was surprised when she spread her legs and pulled him on top of her.

Hard cock met wet pussy, and soon he was balls deep within his wife. She moaned, and he cursed. "Fuck, you're so wet."

"Stop talking and fuck me," she urged, pulling at him with arms and legs.

He did, going at his wife with a gusto rarely seen nowadays. He rammed his cock as hard as he could, as deep as he could, egged on by her cries and pleas for more, more, more.

Years of intimacy meant Tim knew exactly how to drive his wife to a satisfying climax. He fucked her until he heard her orgasmic cries twice before unloading himself into her.

Rolling off of her, husband and wife lay panting side by side. When they caught their breath, they each said, "What brought that on?" almost in sync.

"I remembered something from my youth," Tim said. When she didn't reply, he looked over and said, "What about you?"

Jane was staring at the ceiling, luscious tits still heaving after her exertion. "It's silly. When Jacob left, I thought I saw a bulge in his shorts. I think it was his, you know, penis," she said.

Tim was a bit surprised. "That's why you were turned on? Seeing the neighbour kid's hardon?"

"I think it was because of me. Are you upset?"

"Did you do anything to encourage him?"

"What? No! How could you think that?"

"Just wondering...don't worry about it. At that age, erections can happen anytime."

"So, you're saying it wasn't because of me?" She managed to sound relieved and upset at the same time.

"No, I think it probably was you. You're a sexy woman, Jane. I don't blame you for being flattered," he chose his words carefully. She'd never shown any inclination to notice other men before. Surprisingly it didn't bother him.

"What was your memory?" she asked, turning it back to him. "Some old girlfriend?"

Tim searched his pretty wife's face, wondering if he dared to say what was on his mind. As he searched her face for a clue as to her mood, he could see her piercing green eyes roving over his face in turn. He decided to be honest. "No, seeing you and Jacob in the kitchen reminded me of when I used to hang out in Mrs. Johnson's kitchen, staring at her in her swimsuit."

"That's it? Seems pretty tame."

"Well, actually she gave me my first handjob, and then my first blowjob. That's what got me going."

"Oh!" Jane looked shocked. "That's a bit predatory, isn't it?"

"Are you kidding? It was the greatest experience of my life, up to that point. I was over the moon for days."

Jane shook her head and smiled at him. "Boys. At least I got to benefit from the memory. My lucky day!" She leaned over and kissed Tim thoroughly.

When she was done, Tim said, "It's funny, the memory, and the parallels with you and Jacob in the kitchen, kind of got me thinking...maybe it's time I pay the universe back for its generous gift."

"Yeah?" She smirked cheekily. "How are you supposed to do that? Are you going to give him a handjob in the pool?"

"Ha ha. No, I was thinking someone a lot sexier, with perfect tits, and a peach of an ass could do it. Someone laying next to me, who's name is Jane."

His wife's mouth dropped open, eyes flicking back and forth between his. "What? You're kidding!" When he didn't answer, she continued, "I can't even begin to list the number of things wrong with that idea."

"Yeah? Like what?"

"It's dumb! I'm your wife! I'm old enough to be his mother! What on earth makes you even think I'd even be interested?"

Tim rolled to her and ran his hand down her belly, across her mons and trimmed blonde pubic hair, to her pussy. He deftly stroked his fingers through her wet labia, easily splitting them and finding her gooey entrance. "You were pretty wet from seeing his tented shorts. I think you're more interested than you're letting on."

Jane moaned and spread her legs as he pushed a finger deeper.

He whispered in her ear, "Don't you want to see what he was hiding in his shorts?"

She moaned even louder, eyes closed and head pushed back on her pillow.

Tim spent time playing with her pussy, finger fucking her slowly until she ramped up to another sighing climax.

When she came down, she looked at him searchingly. "What's gotten into you? Are you serious? What your suggesting is fucked up, on many levels. Just because I got a little excited doesn't mean I'm willing to...jerk him off!"

Tim felt the discussion getting heated, but the wrong type of heated. "Look, I know it's odd, but I remember what it was like being a young man, desperate to get laid, and not having any luck; it eats away at you. Mrs. Johnson made a big impact, and I think you could do the same for Jacob."

Jane stared up at the ceiling for a while, before saying, "I don't know, Tim. What about our marriage? It's opening a can of worms that we might not be able to close, and there won't be any going back. You know I can't unjerk him if you get upset. It just, it feels like a recipe for disaster...honestly I'm shocked you'd even suggest it."

Tim smiled, and said, "I admit, it's new, but if it helps...a good part of my excitement just now was from the thought of you and him in the kitchen."

Jane chewed on her lip, cheeks flushed from her orgasm. "You're crazy. You really want me to do that?"

Tim nodded, hands playing with her pussy. "At least think about it?"

"Mmmm...," she sighed deeply, still sensitive. "I...I'll think about it. Assuming you're not teasing me, and assuming I can work up the nerve, I'll consider it. But I'm serious, you need to make sure this is what you want."

Tim rolled on top of his wife, renewed hardon plunging deep into her cunt, showing her how serious he was.

"Ohhhh," she sighed, hands on his shoulders, as he fucked her again.

It had been a few years since he could go again so soon. Something about the image of his wife's hands on another man's dick...

***

Jane had been seriously thrown off by Tim's suggestion. Giving Jacob a handjob? Seriously?

He'd always just been the kid that hung around the street when his family moved here a few years ago, until one day he asked if he could use their pool. They'd let him, on the condition that he help clean it. He'd just been a scrawny teenager until this summer...

Jacob filled out a lot in the past year, and he was now sporting a man's body. Jane had stolen a few glances at him ever since the weather turned nice enough to have the pool in use, and was impressed with what she saw. A lean, swimmer's body with strong legs and, well, she was sure she'd spotted a sizable bulge on a few occasions. Those had only been visible the last couple weeks, but it seemed to be present more and more often when she wore her bikini around the pool. The coincidence wasn't lost on her, and she found her mind wandering.

This afternoon had been the most obvious erection yet, and it sent a jolt of warmth to her vagina seeing the impressive tent in his shorts. When he'd suddenly left, she allowed herself to imagine what it might look like, and then Tim came and 'accosted' her in the best way possible.

After their mid-day sex, and Tim's surprising second bout, they cleaned up and he went back outside with a fresh drink. Jane stayed inside, mind whirling at her husband's shocking request.

Several questions stood out to her. Should she do it? He was so much younger than her. Could she do it? She wasn't the most outgoing when it came to this kind of stuff. How would she do it? Did she just grab his dick and start pumping? The whole thing just seemed so unlikely, whether she was willing or not.

She brought this up to Tim later at dinner.

"It wouldn't take much, believe me. A smile, some teasing, and he'll be eating out of your hand. Maybe just flirt a bit, and see what he does. Flash him accidentally."

Jane still couldn't believe Tim was okay with this, but decided to take him at his word. Even the thought of showing off a bit of her body to the lean, athletic teenager had her blushing.

"Okay, but remember, you asked me to do it," she warned. "What if he, like, tries to touch me? What should I do?" she asked.

Tim considered the question. "Hmmm, well it might kill the mood if you're slapping his hands away. I'll leave it up to you. Whatever you're comfortable with is fine. We're both going to benefit when we have sex after, if you're worked up from having his hands on you."

"Let me get one thing straight. I'm not going to have sex with him. It's wrong, wrong, wrong, I won't do it, you get me?"

"Yes, of course. No sex," her husband assured her, though his cheeks were red when he said it.

"Fine. So, assuming you're not going to hang out and watch, where are you going to be if I go through with this?"

"Let's come up with a signal. If you're going to make your move, ask me to go get ice. I'll know to head out and I won't come back until you text me again."

"Okay," she said, face burning.

The planning seemed to get to them both, and they ended up fucking again, on the kitchen table.

Later, in bed and heading to sleep, Jane reflected that this Jacob talk had resulted in more sex between them in one day than they'd had in the entire last month.

***

The next day, a Sunday, Tim found himself out by the pool once again. It was his favourite spot to hang out in the summer, whether drinking, reading or napping, but today he found himself unable to relax. It didn't take a detective to realize that he was hoping Jacob would come over. The question of whether Jane would go through with his request was still in the air, but even the thought of it had his dick hard.

Jane joined him around lunch, bringing out sandwiches. They discussed the coming week, and how much he'd be around the house. Tim was a high level manager with his company, able to set his own schedule for the most part, but still tied to meetings now and then. During the summer he did his best to spend as much time at home with Jane, keeping her company with outings and lunches. Jane, an elementary teacher, had her summers free.

Just as they were finishing eating, they heard a telltale knock on the side fence gate. Jacob had come for his afternoon swim. Tim locked eyes with his wife, feeling his cock stir.

"Come in, Jacob!" he called.

The young man swung the gate open, saying, "Hi, Mr. and Mrs. Turner." He headed to the pool, dropping his towel and a water bottle on a chair.

Tim didn't miss the lingering look he gave Jane, taking in today's bikini. He didn't blame him, as she was wearing one of her sexier swimsuits, consisting of small bottoms that showed plenty of ass cleavage and a top that displayed the side of her breasts.

Jacob managed to tear his eyes from Jane long enough to dive into the pool, probably to hide his reaction.

Tim caught his wife's eyes, winking. She blushed and stood up, grabbing their lunch dishes and heading inside. Was she backing out? She'd never actually said she would do it...

Jacob swam several laps, his strokes strong and confident. Tim did his best to stay calm, but grinned when he noted himself adjusting a leg to hide his hardon, feeling like a teenager himself.

Jane didn't reappear for a while, prompting Tim to get up and head to the house. If she wasn't going to do it, he may as well know so he could 'stand down' and relax before Monday arrived.

The cool air of the house was refreshing, as usual, cooling his ardour and clearing his head. He went searching for his wife, finding her in the living room on the couch, staring at nothing. When he entered the room, she turned to look at him.

"I can't do it," she said. "It feels like cheating on you. I don't want to do that."

"Why don't you come outside and hang out? Forget about doing anything and just relax. I asked you, so it's not like you're cheating, but I get it. It's a hard adjustment to make in your mind, right?"

She nodded, and stood up, coming over to hug him. The feel of her sexy body molding close to his never got old. He whispered in her ear, "Remember how you felt when you saw his shorts yesterday? It'll happen again if you let it." The small gasp in his ear told him what she thought of the idea.

Pulling away, Tim took his wife by the hand and led her out to the pool.

***

Despite his request for her to relax, Jane felt butterflies in her stomach as she followed Tim out to the pool. She felt a bit silly; this was her house, and nothing had happened, nor had to, and yet here she was feeling like she was going on a first date or something.

When she got to the poolside deck and lay down on a lounger, she took a deep breath and let it out, grabbing sunglasses to dim the sun and hide her eyes. Using the cover of the dark lenses, she scanned the pool for Jacob, finding him floating at the deep end on his back. All normal.