The Best Neighbor - Day 38 (Patreon)

For those wondering this is the second to last installment of this particular saga. Tomorrow I'll wrap up this experiment but until then enjoy some simple, straightforward smut!

After more than a month living at one two seven seven Shadeview Drive and loving just about every minute of it Anna had settled into a comfortable suburban routine. Albeit one that was still far more adventurous than what many of her neighbors were enjoying but a routine all the same. Every morning she'd eat a nice healthy breakfast, film something for her OnlyFans, and either go to work or do a specific exercise based on the day. When she returned home she'd usually visit one of her companions, usually Beatrice and Mark but often times Joy and occasionally Clark, and then round out the day by watching whatever show she was currently working her way through. Depending on how she felt or the kind of day she was having she'd hookup with either of her local fuck buddies or call out to a friend in the industry if her regular bedfellows were occupied. Once a week she got groceries, took the cans to the curb, and did all the other banal aspects of living in a proper house. It'd become so normalized she almost didn't realize how easily she'd slipped into the same habits day after day. But the strangest thing of all was how little she actually minded that realization. There was something quite reassuring about a stable, easily predicted life. It was certainly a far sight better than the more hectic life she'd had in the city.

Of course that didn't meant she wasn't interested in spicing things up a little bit should the opportunity arise. And almost as if was planned out ahead of time that chance arrived in the form of an ex boyfriend named Chester Smithson. She recognized his tall, dark, and handsome physique from across the grocery story parking lot the moment she stepped out of the car. Practically sprinting across the parking lot Anna called out to him, enthusiastically waving as she did so. He turned towards her with a quizzical look but his broad features immediately lite up in a grin upon seeing who was shouting at him. It'd been nearly eight years since they last spoke to one another beyond the occasional text and pretty much the instant they locked eyes it was like they were back in high school again. Upon reaching him she had to fight the urge to jump into his arms like she used to. More than a foot taller than her and built exactly like the athletic man that excelled at every sport he tried Chester was every bit as attractive as he'd been in high school. Maybe even more so now that he'd shaved his afro and was wearing a nicely tailored suit.

“Oh my God!” She exclaimed, throwing her arms around him for a tight hug, “I can't believe I just ran into you like this!”

“Neither can I!” Chester replied as he returned her hug with just as much enthusiasm, “It's been forever since I saw you!”

“It really has! I can't believe how good you look?”

“I was gonna say the same thing to you! Remember when Marcy Donovan said we were the kind of people that only got fat and ugly after high shool?”

“She must have been talking about herself huh?”

Both of them burst into laughter, completely unconcerned with the people they were blocking in front of the supermarket, “Man . . .” Chester looked her up and down for a moment, “You really haven't changed at all Anna.”

“That better be a compliment!” She replied.

“Hell yeah it's a compliment! You were the sexiest girl in school!”

“I think you're confusing sexy with wildest!”

“Nah, you being wild just made you fun. You would've been sexy even if you dressed like a Mormon.”

Anna loudly snorted, covering her mouth and looking shocked at the sound that'd just come out of her mouth. It really was like she'd been thrown back nine years in the blink of an eye, “What've you been up to all these years? I never thought I'd see you in a suit!”

“Me neither! And you're not gonna believe this but I'm actually an accountant now.”

“No fucking way! Don't tell me it's at your dad's office!”

“It is. I'm on track to be a manager.”

“Who the hell are you?!” Anna exclaimed, playfully smacking his arm, “What happened to the kid that said he'd rather dig ditches than work with his dad?!”

“He got a mortgage and a house.” Chester laughed. “Turns out partying all the time doesn't make much money.”

“Yeah you're telling me!”

The two of them lapsed into a short silence as they smiled at each other and thought about the weird paths their lives had taken, “So does that mean you've got a wife and kids now too?”

“Hell no! I mean I want a wife and shit but kids? That's still at the bottom of my to do list—”

“Right above cutting off your dick and diving in front of a semi truck.” She finished for him.

“Of course you still remember that.”

“You said it all the time!”

“No I didn't!”

“Yeah you did! Like every time we saw someone with kids!”

“That's only because you were always acting like you wanted kids!” He laughed.

“No I wasn't! I just thought they were cute! You think I wanna squirt out a couple of brats that're gonna be just like us? We'd kill them in five years tops!”

“That's for sure. I'm amazed our parents did kill us back in high school.”

“I'm amazed my parents didn't kill you back in high school!” Once more their conversation halted as the two of them shared a hearty, nostalgic laugh. Anna looked him up and down once more as a thought formed in her head, “So you don't do any of the crazy shit we used to get up to?”

“Not really. Most night's I'm in bed by ten or eleven.”

“Wow, you're super boring.”

“Hey we can't all have the kind of job you've got!” Chester replied in a tone that immediately told her he was familiar with her career. But rather than seeming judgmental he almost sounded envious. “Some of us have to be boring so lunatics like you can shine all the brighter!”

“Hey I'm no lunatic these days! I bought a house a month ago! I live in the suburbs!”

“Seriously? Wild Wild Anna settled down? Who's the lucky guy!|?”

“There's no guy you sexist! I just wanted to live somewhere that didn't suck ass!”

“Yeah I can relate to that.” Chester nodded. He stared at her for a few seconds before asking, “So you're single too huh?”

“Yeah I am Mr. Subtlety.”

“What? I was just asking?”

“Uh huh. So you weren't gonna try and hit on me?”

“Not at all!”

“I guess I'll have to do all the heavy lifting like always.” Anna replied with a mischievous gleam in her eye.

The two of them stared at one another for all of five seconds, each absolutely certain they knew what the other was thinking. She arched an eyebrow and his smile widened. In unison they looked towards the alley beside the supermarket and then back at one another. Without saying a word they made an immediate beeline for it as though it held all the mysteries to life. They didn't even care how conspicuous it looked for them to rush off practically holding hands. All they could think about was tearing into each other like the old days. Anna managed to reach the alleyway first and she wasted no time darting behind one of the large dumpsters that would obscure them from casual passersby. Her ex wasn't far behind her and the moment they'd vanished from sight she leapt on him like a caged animal that'd finally escaped. 

Absolutely thrilled she'd worn a skirt that day Anna threw her arms around his shoulders and wrapped her legs around his waist. His massive hands closed around her hips and their lips met for the first time in what might as well have been centuries. She was flooded with more nostalgia than she could handle as his tongue pushed into her mouth like it had so many times before. Hers responded in kind and the two of them shivered like mad in the first few moments of their embrace. A long, passionate moan burst from the depths of her soul and she started grinding against him soon after. His massive bulge strained against his slacks and felt absolutely incredible against her pussy. With only a couple layers of clothing in the way it would be so easy to pull them aside and fuck like they did back in high school. Although back then they probably would've have bothered hiding behind the dumpster but even with that little alteration it still felt so fantastically familiar. Like she'd flipped a switch Wild Wild Anna was back in force and she had her man along for the ride.

His hands jumped down to her ass almost immediately and the way her groped her firm buttocks, simultaneously pulling them apart and squeezing them, made her shudder like few things could. Anna kissed him harder than ever and moaned even more loudly. The feel of his body against hers, his cock rubbing against her pussy, and his hands fondling her ass was beyond nostalgic. All she could think about was getting his dick inside her ass soon as humanly possible. Apparently he was thinking pretty much the exact same thing because not ten seconds after she acknowledged that thought he'd pushed her against the wall. Keeping her aloft with one hand Chester reached down to unzip his pants with the other only to be rebuked by Anna's far more eager fingers. She unfastened his slacks and freed his ten inch shaft so effortlessly it was almost like a magic trick. A moment later she'd yanked aside her panties and lifted his prick up to her sodden, puffy lips. All without breaking their kiss or even slowing the emphatic movements of her tongue.

“Goddamn you really what you're doing!” He groaned as she rubbed his shaft against her slick folds for a couple of seconds.

“You say that like I couldn't rock your world back in the day.” Anna replied.

Chester laughed and stared at her for a second. She had all of a moment to realize what he was about to do. But her mind was still basking in the thrill of reliving her wild high school days and it was woefully unprepared for his sudden thrust. With the kind of force that used to split her in half he slammed his cock inside her pretty much as hard as he could. In the blink of an eye her pussy was stuffed with and wrapped around his giant prick and all the memories she'd already been enjoying exploded into her thoughts. Her whole body remembered the feel of his dick like it was only yesterday and the pleasured scream she unleashed demonstrated this familiarity more than anything else could. Lost among her near orgasmic enjoyment was a long, satisfied groan from Chester. But while she didn't hear his reaction she certainly felt his grip tighten around her buttocks and his cock swell like mad inside her. What had already been a massive shaft that stretched her tight little walls was quickly becoming the sort of thing that could utterly ruin a woman's pussy. And Anna was absolutely delighted by it.

Her eyes started to roll back in her head pretty much the moment he began to move and her mouth fell open in a breathy gasp. His cock retreated all of four inches before slamming back inside her and yet that short distance had been enough to elicit a full body quiver from her. It's triumphant return to her pussy along with the feeling of his weighty balls colliding with her flesh caused another. Before long that was the new normal for them as he started fucking her properly. Perhaps as a consequence of their shared nostalgia or simply as a sensible tactic he was moving far more slowly than his initial thrust might have indicated. Chester's movements were undeniably faster and the alley was already starting to echo with the meaty smacks of his beautiful ebony body colliding with hers but they both knew it wasn't anywhere near what he was capable of. That knowledge was as much of a source of pleasure for Anna as the actual fucking itself. Having a constant reminder in the back of her mind that soon he'd be fucking her like a five dollar whore made the build up deliciously sweet. Enough that she paradoxically didn't want it to end.

Luckily for them her wildly conflicting urges weren't steering the ship and Chester's hips continued to pick up the pace regardless of what she thought she wanted. Anna's moans fluctuated between gasping squeaks and long, almost guttural sounds pretty much at random while his cock steadily pounded her tight cunt. Her fluids had absolutely soaked his dick and although they couldn't see it both of them knew full well those juices were falling off his prick like rainwater dripping off a log. She was keenly aware of little flecks of her arousal splashing all over their thighs each time he slammed into her and there was no doubt in her mind his balls were similarly drenched. Just as there was no doubt in her mind that if he continued the way he was going she wouldn't be able to keep up. She could never really keep up with him but that fact hardly seemed relevant by that point. Much to far gone to stop Anna was gonna cum no matter what. Even if it meant doing so in front of a cop.

They were lucky enough to avoid testing that commitment for the time being and Chester was free to continue steadily increasing the speed and force of every thrust until they were lifting her off his cock each time he plunged inside her. Anna gave up completely on expressing her satisfaction verbally and instead let the rest of her body to the talking for her. Between the deluge of fluids, the madcap quivering of her inner walls, and the scraping of her nails against his jacket there was no way he didn't know what he was about to do to her. Had she any cognizance of what was going on right in front of her face she would've seen that smug grin Chester always had when he made her cum. And she would've scowled at it just like she used to do, even as she sank into a full body climax. Too bad years of fucking had made her even more sensitive than when she was in high school and comprehending anything beyond his dick was simply a lost cause. Especially as she plummeted into the churning sea of ecstasy that'd been stirred up inside her.

Suddenly finding her voice just long enough to scream his name Anna buried her face in Chester's shoulder and let it all wash over her. Juices sprayed from her pussy in thick, gooey strands while every inch of her body either trembled or tensed seemingly at random. Her breath came in ragged gasps while her hips tried to gyrate against him. And through it all he continued to thrust at the same tempo and with the same power that'd brought her to that point. There was a subtle increase to both but it was far to gradual to register and she was hardly in any position to notice such things anyways. Holding on tight to her while she shook so violently it was like she was having a seizure Chester's soft laugh was about the only thing that registered to her frazzled and broken mind. She wanted to lift her head and make some sarcastic comment like she used to. She wanted to tell him off right before she swooped in for a sloppy kiss. Instead all she managed was another watery cry as her fluids drenched both of them along with the ground below. Her desires were soon swept away as surely as a sandcastle beneath a wave and in their place was unbridled lust and affection for the man and the dick causing all this.

Thanks to his self control and her penchant for long, messy orgasms Anna's climax didn't even begin to fade for nearly two minutes. She experienced plenty of ebbs and flows but now matter how much it might have dipped her pleasure was always the sort that left her utterly speechless. Which meant she had no way to respond when Chester announced he was going to cum a short while later. Under different circumstances she would have enthusiastically encouraged him to drain his balls inside her, to dump as much cum as he could into her pussy like the old days. But since her voice wasn't working her body had to do that for her. It gladly took up that responsibility and in not time at all he was thrusting in that uncontrollable way that always preceded one of his orgasms. She tensed with every furious smack of his hips against hers and when the big moment finally arrived Anna threw her head back to offer a silent scream to the cloudless sky above.

For the first time in nearly eight years his spunk flooded her pussy in a thick jet. The first load to erupt from his dick gushed so deep inside her she could have sworn it was somehow making it's way through her stomach. The second arrived hot on the heels of a powerful thrust and that seemed to send it even deeper than the first. Anna was pretty much ready to call it quits after than but she knew full well he wasn't done. A radiant smile spread across her face as he continued to fill her with cum, just about every spurt being heralded by a thrust. But even the ones that weren't managed to serve the fantastic role of smearing his fluids all across her inner walls. And for that she couldn't have been more delighted. By the time his orgasm was nearing a close it felt as though every inch of her pussy was coated in a thick layer of jizz and even if that wasn't true the sensation alone was enough to make her squirm and whimper in satisfaction. It could only have been better if it lasted just as long as one of her orgasms. Sadly such a thing was impossible but it did little to diminish her enjoyment.

Chester let out a final groan as her thrusted one more time inside her. The last of his cum sprayed into her already overstuffed pussy and Anna moaned in abject satisfaction. Her head fell back against the wall she'd been pinned against as spunk started leaking out of her almost immediately. Like he had every other time before her ex kept his dick buried inside her for as long as he possibly could. And since nobody had come by to chase them off yet that meant he could keep that fat prick of his buried in her cunt until it finally slid out of it's own accord. After nearly a full minute of her inner walls clamping down around it and trying to coax out any cum that still might be left in his plentiful balls. When his shaft finally did slip free it was accompanied by a small moan from her, a shudder from both of them, and a nicely wet pop as her once sealed pussy was suddenly uncorked like a bottle of wine. All the jizz he'd pumped inside of her started leaking out onto the already filthy ground and she happily let it dribble. There was something enormously satisfying about feeling his semen leaking from her pussy after he'd so eagerly and enthusiastically pumped it in there.

“God damn this takes me back.” Chester panted.

“Yeah it does . . . although I don't remember us being able to hang around this long in the old days.”

“That's because we always got caught. Usually cause you couldn't keep your voice down.”

“Most guys would take that as a compliment.”

“Most guys don't wanna get chased out of a restaurant by angry waiters because they got caught fucking in the bathroom.”

Anna laughed and smiled at him for a little while. “That was a lot of fun.”

“Yeah it was.” Chester agreed. He lowered her to the ground as he spoke and stepped back to put his cock away, “I haven't done anything like that in a while.”

“Me neither.” She reached into her purse to pull out some napkins and wipe away the bulk of his cum before it could stain her clothes. 

“Do you ever miss it?”

His question took her by surprise and yet despite that she immediately knew her answer, “Not really. I enjoyed the hell outta this . . . but I think that was more nostalgia than anything else you know?”

“Yeah I get what you mean.” He said with a nod, “This was all kinds of fun but I don't think I could do it like we used to.”

“Well you are getting older.”

“Pfft! Says the girl who used to stop every five minutes because ti was 'too much'!”

“You shouldn't have made me cum so fast!”

“Do you even hear yourself?”

For the millionth time they paused to share a laugh and once they were done and both of them had finished cleaning themselves up Anna took a deep breath, “You sound pretty happy with how things are now.” She observed.

“I am.” Chester stated with total confidence. “What about you? Are you happy living in the suburbs and working as a pornstar?”

“I am.” Anna stated, “I really like where I live and I really like the people that live around me.”

“I'm glad to hear it.”

“Yeah me too. And I'm glad to hear you're happy where you are.”

“Thanks . . .”

“Yeah . . .”

“Man . . . I can't even imagine what our younger selves would think if they saw us now.”

“Well I'm pretty sure the younger version of me would want to fuck the past and present version of you.”

“Oh without a doubt. And I'd probably give in. You always could get me to do whatever you wanted.”

“Yeah I could.” Anna said in a soft voice, smiling up at him as she spoke, “It's good to know that hasn't changed.”

“Yeah it is . . .”

The two of them stood in that alley for a short while, each contemplating their lives as they did so. But then the nearby door to the supermarket opened and they bolted out of there as quick as possible. “Hey do you wanna get a cup of coffee?” Chester asked, “I'd love to catch up a little now that we've caught up a lot.”

“Coffee sounds good. But we can't take up too much time I've gotta pick up some things for a little get together my neighbor is throwing.”

“Yeah I needed to buy more toilet paper and detergent.”

“God we're so boring now!” Anna squealed.

“We sure are.” Chester grinned, “But I'll take that over our old life any day of the week.”

“So would I. Especially if I can still fuck hot guys in alleys every once in a while.”

“Oh well that just goes without saying.”

“Naturally.”