Putting in the Work

Taking what you want was an easy lesson that Josh learned early on in life. In childhood, that manifested itself as bullying, often as not. He wasn't a bad kid, he was just an assertive child who was regularly told he needed to learn to share by teachers year after year.

He wasn't that interested in things like that, though. Instead, if he wanted something, he went for it. However, eventually he grew out of it. By the time he was a little older, he'd found a better way. He didn't need to shake his classmates down for a buck or two when there were better opportunities.

Soon, he was shoveling snow, mowing lawns, cleaning pools, and making more money than he could spend by putting in a little hard work most afternoons. His friends thought he was being left behind, but by the time they were going off to college, he was already making most of them. When you were getting paid in cash, and busting ass with a growing business that had customers across half the city things really started to add up.

At the parties they went to in his early twenties, they tried to convince him that he was missing out, even after he explained to them that by this time next year, he'd be making more than they would, even after they went a hundred thousand dollars into debt to pay for their fancy computer degrees.

"Yeah, but you're forgetting one thing," Terry told him. "The babes."

Everyone laughed at that, especially Josh. "I'm serious," Terry pushed back. "Maybe you can make as much money without going to school, but where on God's green Earth are you going to find more young, hot, slutty women in one place? I'm telling you, Josh, they're practically giving it away. You should be going to school for the college experiance, if nothing else..."

That time, there was a mixture of laughter and agreement, but Josh just shrugged and took another sip of his beer. Young wasn't something he'd had a lot of experience with, for better or worse. Girls his own age were still somewhat of a mystery to him. They ran hot then cold, and flirted hard and heavy before changing their mind. It took him a while to figure out it was that they didn't know what they wanted.

He didn't blame them for that. Most people his age didn't.

Older women, though, like the housewives he ran into every day while he cleaned their pools and shoveled their mulch? Well, a lot of them needed some extra service that only a strong young man like him could provide, and they made that clear enough that even an idiot like him wouldn't miss it.

He wasn't about to tell Terry that, though. Why should he? He was fucking the guy's mom once or twice a month at this point, and he wasn't going to blow a good thing just for bragging rights.

So, instead, he took the ribbing, and he promised to consider going to school one day. In reality, the only thing he was going to consider was who he was going to add to his route next.

In the beginning, Josh had knocked on every door, looking to drum up work so that he could afford to buy a car during his senior year. That had worked well enough for a while, and cash stacked up fast once you had a route of 40 yards that needed to be mowed every other week. He'd gone without weekends for just long enough to begin to resent it when Ms. Stephenson had invited him in for a nice cold glass of lemonade and taken his virginity a few weeks after he'd turned eighteen as an extra special tip.

That was a hell of a moment for a young man like him. One second, he'd been pissed that he wasn't going to be able to party at the reservoir next week because he had too much work, and the next, he was sitting at a stranger's kitchen table while a beautiful thirty-something Milf was on her knees devouring his dick while she told him how handsome he looked with his shirt off.

Mrs. Stephenson had rocked his world that day, and as he buried his dick for the first time in her hot, hairy pussy, he knew there was no going back. There was just something about blowing his load in a woman that hadn't had a good fuck in years that changed him.

After that, and a couple of similar encounters with beautiful neglected housewives and divorcees, he was hooked. Now he was no longer just offering the usual menu of services like weeding gardens and cleaning gutters. He was also laying pipe pretty regularly.

From then on, he still knocked on every door, but he only quoted reasonable prices for the women he wanted to fuck. Josh made a wish list, and after getting tired of waiting for them to make the move, he learned to hit on them at the first signs of interest.

That was how he'd banged Terry's mom while he was away at his first year of college last spring. One minute, they'd been talking about school and whether or not he'd attend after he saved up some more money, and the next, he'd had the forty-five-year-old cougar bent over the kitchen island while he pounded her pussy with a hunger that bordered on desperation.

He enjoyed banging anyone, of course. They were all adults, and most of the older women still managed to teach him something new every month. There was just something about fucking someone's mom, though. It wasn't something he understood, and honestly, Josh didn't try. He was no deep thinker, and he was happy to be led around by his dick. It was pretty smart in its own way.

So, while his high school friends were busy swiping right and buying drinks, hoping to catch some young hottie's interest, he was getting paid to drain his balls into a new woman every few days. It was hard to beat that.

For a long time, he didn't find a way, and then one day, Mrs. Lewis asked him to start cleaning her pool. Like every guy with a pulse, he'd had crushes on half of his high school teachers, but if he'd only ever gotten the chance to fuck one of them, it would be Mrs. Lewis.

Despite being 38, she had a body that competed with half the student body. Her fat ass, wide hips, and ample bosom certainly made that easy enough. She was like a walking fertility symbol, and though he knew nothing about bra sizes to estimate, he was pretty sure that 'tits as big as his head' was as accurate a measurement as he needed.

She also wanted him. He could tell.

Maybe not at first, or right away, but he'd only visited her house half a dozen times before her patterns started to change. Soon enough, she was out there sunning herself every time he came over to scoop some leaves and check the chlorine and all the other little chores that made pools look nice.

When he'd started doing these jobs, he'd just assumed that sort of behavior was a coincidence. However, at this point, other than coming out to pay him while wearing a housecoat with nothing on underneath, or asking him if he wanted to come inside for a nice cold drink, it was the surest sign of interest he knew.

He always wanted to cum inside, and if some sweet woman twice his age offered to let him use her shower, she would usually join him within a few minutes, wearing nothing but a smile.

Mrs. Lewis was no different from any of them in that sense. The only difference was that he wanted her more, so he took his time with it. After all, why fuck up a perfect fantasy like this?

Instead of complimenting her rack or kissing her hard and finding out if she'd slap him or kiss him back, he just took it slow. Every other week, he saw her, and every time he did, he made sure he was shirtless, tanned, and looking good. After that, he let her talk about whatever she wanted to while he worked.

Usually, that came down to complaining about the kids she was teaching or other minor bits of gossip, though looking at the pictures of the man, it didn't look like she was missing much. To Josh, Mr. Lewis looked like a weasel in the family photos he'd seen, but he didn't mention that.

He didn't take any of the easy bait. Instead, he just bided his time, waiting for a perfect pitch to hit his home run. After all, why was he in a hurry? He'd gotten his balls drained three times this week by three different MILFs. So, it wasn't until she asked if he had a nice, sweet girlfriend waiting for him to finish his work that he made his move.

"Nah," he answered, looking her right in the eyes as he leaned the pool net against her house. "I'm just not very interested in girls my own age if you know what I mean."

"No?" she squeaked, trying and failing to sound natural. "I-I'm not sure I do..." The color in her cheeks as he walked toward the busty redhead certainly suggested she knew exactly what he meant, and her denial was almost as transparent as the teal bikini she was wearing once it got wet.

The whole time that she'd been chatting with him, she'd been basking in the sun on a lounge chair. When he reached her and crouched down so that he was less than a foot from her face, she only flinched a little.

"No? Then let me spell it out for you?" he said with a smile. "Girls my age are pretty, but they have no idea what they want. I prefer women who know exactly what they're looking for."

"Exactly?" she said, licking her lips. "I hate to disappoint you, Josh, but--"

At that moment, she was looking to explain to him why there were good reasons that they didn't do this, but he wasn't about to let his old teacher talk herself out of what she wanted. Instead, he kissed her hard enough to silence her, and after trying and failing to pull away, she started to kiss him back.

Hesitation didn't last long, and soon, it became hunger. He let the moment linger, though, and it was only after their tongues had been wrestling for half a minute that he finally broke the kiss.

"It looks like you know what you want to me," Josh said with a cocky grin, "But if you want some help figuring it out, I'm pretty helpful with these sorts of things."

"Joshua Thompson, I am your teacher!" she said with a note of ferocity. Her message was almost completely undermined by the fact that his right hand was now palming her left tit like a basketball, and he could feel her hardened nipple pressing into his palm.

"No, you aren't," he growled. "You were my teacher, and though this would have been creepy then... well, I'm old enough to drink now, and you've been aging like a fine wine all this time."

He kissed her again as he slid his hand underneath her bikini top. She struggled again, but not so hard that she wasn't kissing him back and gasping by the end of it.

"But I-I'm a...mmmhhhh... an old woman," she protested as he twisted her nipple.

"Not even close," he countered, not that she hadn't mentioned her husband. For most women, that was usually their first fig leaf, not that he cared if they were married. "But if that's the way you feel, I know a really easy way to make you feel young again, Mrs. Lewis."

This time, there was no resistance, and when he peeled her out of her chair and took her into her nice air-conditioned home. He'd been tempted to fuck her on the edge of the pool. He'd even worn swim trucks for that reason, but there was just something about the voice of a woman who'd lectured you about wasting your potential, and he didn't want her to stay quiet in case the neighbors heard her. He wanted to hear her scream.

"This is so wrong," she murmured.

That didn't stop Josh from leading her by the hand to her master bedroom, though. "It is," he teased. "You're about to get fucked by your former student in your marriage bed. How does that make you feel?"

As he spoke, his second had ground against her clit through her bikini bottoms because there was only one right answer to a provocation like that, and that was to moan as the shame ran through her. "Joshua... " she breathed.

She didn't get the chance to finish, though. Instead, as soon as they were in the bedroom, he pushed her back onto her bed and then crawled on top of her, heading straight toward the tits he'd spent years fantasizing about.

This was probably the part where he was supposed to make some clever teacher joke or remind her how beautiful she'd always been to him. He didn't, though, because he knew he didn't need to. Doubts would have already been handled in the hallway or the living room. Now she was looking up at him with partially lidded 'fuck me' eyes, and even as he pulled down her top so he could suck on her big, saggy tits with his hungry mouth, he was already kicking off his shorts and sandals.

Mrs. Lewis was gasping and squirming beneath him, "We shouldn't be doing this..." she murmured as he attacked her body. "I-I.... unnhhh... I shouldn't want this so fucking bad."

"You shouldn't," Josh agreed, reaching down to finger fuck her as he took a quick break before switching to her other breast. "You're a married woman, and I'm half your age..."

"We're... mmmuhhhhh s-s..." she gasped. "Fuck. We're separated, but you're... you're... oh fuck... right there...Mmmmmmm... but you're twice the man that he ever was."

She blushed as she said it, reveling in her shame, but he ignored her words as he pulled his fingers out of her sloppy, shaved pussy, and pulled the strings of her bikini to untie the knots and leave her pussy bare beneath him. Now wasn't the time to get clever. It was time to get laid.

"Only twice?" he growled as he ground his thick prick against her wet cunt, basking in the slick sensation of skin on skin. "I need to up my game."

The combination of the taunt and the liquid friction made her moan out loud, but she said nothing about a condom, so as far as he was concerned, that was permission to shove his cock as deep inside her as he could. Some of the women he banged demanded that he use a rubber, which he did grudgingly.

Pussy was still pussy behind a thin layer of latex, but it had nothing on the real thing. As far as he was concerned, there was no better feeling than that moment when he came inside a new lover and flooded her womb with his seed, and this afternoon, he was going to find out if that little taste of heaven was even better with a woman he'd fantasized about for years or not.

"Please," Mrs. Lewis gasped, legs spread wide beneath him.

The only answer that Josh gave was to rub his swollen cock head up and down her soaking slit twice to get it nice and juicy. Then, with no warning at all, he shoved all six inches inside her.

"Oh fuck..." she gasped as he bottomed out inside her. "Holy... you're in me... you're really in me..."

Josh didn't answer. Instead, he moved his head back to her right nipple and held his dick right where it was for a moment so he could bask in the delicious feelings she was creating in his dick.

"I am," he said finally. "I'm sucking your tits, I'm in your pussy, and any second now, I'm going to give you the fuck you've been dreaming of for years."

"Oh god, why do I want this so bad?" she moaned as he started to slide out of her for the first time. "In our house... on our bed..."

Her words might have been conflicted, but the way her fingernails were digging into her back left no doubt at all what she wanted in his mind. "Because you're single now. You're just a slut for any man that notices how hot you are in that bikini, aren't you?" he growled possessively.

"I'm not...mmmmm... I'm not..." she repeated over and over for the next several thrusts that what he'd said wasn't true. Josh didn't care if it was true or not. All he cared about was that it turned her on.

"I never w-wear things like... oh fuck... like this anymore..." she whined.

"So you did it just for me?" he teased. "Even better."

"I did!" she confessed as he slammed against her womb. "I... I just wanted someone to want me!"

"Well, I want you, Mrs. Lewis," Josh grunted as the speed of his hips increased. "I've wanted you for so fucking long, and now I have you!"

"Oh god, you do..." she moaned, "You do, you do have mmmmmeeeeee..."

"Now I can fuck you whenever I want," he bragged, "and I'm going to. I'm going to devour these tits all the time."

"Y-you do? You w-will?" she stammered, caught completely off guard.

"I do," he promised, hammering the point home with an especially powerful thrust that made both of her saggy breasts jiggle violently. "I'm going to drown this pussy in cum."

"Ohhhh oh... God, that's so fucking hotttt..." she whimpered, getting close to cumming. "But you shouldn't... oh god, I haven't been on birth control in yeaaarsss...."

Josh didn't stop fucking her even after she started cumming on his dick. Instead, he sped up. He was getting close, too. "Well, if you want to tell me to pull out Teacher... If you want to tell me not to drain my heavy balls into your unprotected cunt... you're running out of time."

The timing of that warning made him smirk, even if he was running out of time, too. He was in pretty great shape these days. If his cock cooperated, he could have kept up this punishing rhythm all day, but the pussy he was in now was tight and wet, and most of all, it was new. New always made it harder to last because all his idiot dick wanted was to mark the territory as his.

At this point, the very last thing he wanted was a kid, but somewhere deep inside his primitive monkey brain, he wanted to seed every last fertile female that crossed his path. At this point, he'd devoted way too many masturbation sessions to this particular cunt to leave it empty, and part of him would have wanted to fill it up even if she'd been begging him to pull out.

She couldn't beg for that or anything else, though. At this point, even if she wanted him to pull out and blow his load on her big, juicy tits, she was too far gone right now to form proper words. Besides, her body was telling him everything he needed to know.

As he thrust in and out of her, he could feel her thick thighs wrapped around him, holding him in place. So, with one final thrust, he bottomed out against her poor, bruised womb and roared, "Take it slut!" as his balls exploded and cum jetted out of his throbbing dick.

"Oh... oh... It's so warm..." she moaned, wrapping herself around him as he bucked and grunted and dumped more and more cum inside her.

It was only when he was finally finished that he rolled off her, and she curled up next to him.

"I can't believe I let my student cum inside me," she sighed as his semen oozed out of her battered sex.

"You can't?" he asked. "Maybe you'll believe it the next time it happens, and if not, then maybe the time after that."

"Who says there'll be a next time, Mister?" she teased. "Maybe I only make each mistake once."

"Simple," he agreed. "If you don't want there to be a next time, just wear something that doesn't show off those big beautiful tits, and I'll treat you like the respectable woman you pretend to be instead of the needy little cum slut you are."

She sighed, holding him even tighter. They both knew that the next time he came by to clean her pool, she'd be wearing even less than she'd been today. There was no doubt in the world what she wanted him to do; all that would be left to decide was exactly how he wanted to use her curvy body next.