Ryan almost jumped off the couch, releasing his hard cock, without even the presence of mind to use his dry hand when he reached for the TV remote. The doorbell startled the fuck out of him, as would any such intrusive noise coming from outside the little shell into which he had retreated this particular morning.

Wracked with nervousness, he transferred the remote hurriedly into his dry hand, frantically pressing at the power button. But the bottomless blonde on the TV kept bouncing lewdly and noisily up and down on a thick cock. She had gone to her friend's house to go shopping with her, but her friend had forgotten and left with her boyfriend, so she was left standing there with her friend's brother ogling her in her halter top and tiny shorts. Ryan forgot what the conversation was like, or wasn't paying attention, but sure had been enjoying watching the ensuing XXX-rated blowjob and graphic display of the starlet riding the brother on the couch.

After he got the remote turned the right way around and found the proper button, the sight and sound of the girl's tight pussy getting fucked close up was replaced by dark silence. Ryan scurried down the hall toward his bedroom, his bouncing cock slick and slimy from his spit. As he retrieved a pair of gym shorts, his nervousness dissipated and his breathing became more regular. He wondered to himself why he was so worked up. No one could see what he was doing from outside, right? But still, the intrusion was quite a shock.

Ding-dong!

“Fuck,” Ryan muttered, as he realized he'd just put his t-shirt on backwards. He pulled it off and flipped it around as he made his way out out of his room toward the front door. He checked the TV again just to make sure, and yes, it was still off. He hadn't had time to find underwear, so he was freeballing it in his gym shorts, his erection having lowered but still poking into the material uncomfortably. He adjusted his cock as he set his eye to the peephole.

It was Miss Prestine from next door. Panic set in for a moment, his thoughts rushing toward a worst-case scenario. Maybe she heard the screams from the TV if he left a back window open and was checking to see if something was wrong? Maybe she had an emergency and would plead with him to perform CPR on her 90-year old visiting uncle? Whatever it was, he thought he had better open the door, because, fuck, he just banged his knee against it, so now she would know someone was in here and he couldn't just hide.

“Oh, hello, Miss Prestine,” Ryan greeted her, sheepishly, opening the door a crack.

“Oh, thank goodness. I was hoping Mr. Tennyson was home? Or you. I have, um, something.... I hate to ask, but maybe someone could help me for a few minutes?” She was obviously agitated.

“Um, sorry, my dad's not home. He goes to the office now usually.” Ryan's dad had been working from home for a few months as many other people had been, but he was back to commuting by this time. Same went for his mom. “My mom's at work too.”

“Oh, okay, well, maybe you can help?” She wasn't dressed for work, just in a tank top and leggings, so she probably didn't need a ride anywhere.

Ryan opened the door further and tried to peer next door, wondering what the deal was, reluctant to offer assistance. “Um, what's up?” he asked. He tried to stand sideways and hold his hand in a way that shielded his half-boner from his neighbor's view. She was actually not bad looking for an older woman, and wow, when she turned and walked out toward the yard, that ass looked pretty nice in those tight pants below the shirt that ended just at her waist. He had admired her ass before, but never quite like this.

She pointed out of his view, obviously wanting him to come look. He had to, even though he knew his boner would be noticeable unless he stood behind her or tried to hold his hand just right. Standing behind her ass in those tight pants sure wasn't helping his cock to get any softer.

“I had this delivery this morning,” she told him. There were two pallets with bags on them, and two huge pots with little trees that must have been five feet tall sticking out of them. “And they just left the shit there.” Sounding embarrassed by her language, she corrected herself. “The stuff there, in the street.”

“Oh, that sucks,” Ryan replied.

“They said they couldn't carry it into the back yard because I didn't pay for 'delivery', just 'drop-off' or some shit- um, something like that. So I was hoping ...” her voice softened, “that maybe a strong young man was around to help me carry them into the back yard?”

“Oh, um, sure, I guess. I can't right now, I mean, it will be a few minutes.”

“Oh, thank you, and sure, right, you might be in the middle of something, just, whenever.”

“I mean, I have to put shoes on.”

“You mean now, in a few minutes? That would be great.”

“Sure, I guess. I can be over in a few minutes.”

“Okay, great, thank you. Finish getting dressed, and—” she noticed the point in the front of his shorts, realizing she had not agreed with him about shoes, but rather commented about his dress in general. “Yeah, your shoes on, whatever you need.” She could tell he was embarrassed as he turned away, sure that he knew she'd seen a little more than she should have.

“Alright, I'll be over in a little bit,” Ryan said, almost hurrying inside. “Fucking... fuck!” he cussed himself audibly as the door clunked shut behind him. He couldn't believe his neighbor fucking saw his boner. He wondered if things would be weird, if she would try to avoid him and shoo him away at the first opportunity after the heavy stuff was in the back yard, thinking his boner was for her instead of having been left over from jerking off to the porn he was watching.

Ryan took a few minutes to get rid of the setup in the living room, disconnecting the external hard drive from the the USB port on the side of the TV, and grabbing the towel he had been sitting on from the couch. He had this morning all planned out, and was annoyed that it got interrupted. A few months ago, his buddy had showed him where to download archives of porn movies, so he had gotten a drive fairly full, and now that his parents were back at work and school had just let out for the summer, he could view porn for several hours per day some days. As a fairly industrious seventeen year old with one year left in high school, he was taking an afternoon summer class that would count for college credit next year, but he still had a bit of free time, and used it to indulge his continued exploration of sexuality by watching and masturbating to his growing porn collection.

Stashing his hard drive in his room, Ryan selected a pair of snugly-fitting boxer briefs and the heaviest shorts he could find. If he started getting a boner again, he wanted something to suppress it. He smiled at his dirty thoughts, now that he'd had some time to sort out his nervousness and embarrassment. He wouldn't be surprised if he did get another hard-on being around Miss Prestine for the next few minutes. She wasn't bad looking for a mom – yes, she had a small son who was probably school age by now, so that made her a proper MILF – and he had on occasion fantasized about fucking her.

- | - | - | - | - | - | -

Jennifer Prestine got busy in her back yard, moving some wood that was stacked against the fence, raking the old mulch away into a pile, clearing spaces for her new trees and plants. Ryan would be there in a few minutes, and she didn't want to keep him for long, trying to arrange things so that he could just help her carry the trees to their spots, lug a few heavy bags, and then get back to his day.

She giggled at herself for the naughty thoughts that popped into her head. That really was an actual semi-erection she saw in his shorts. It was unmistakable, and he was embarrassed, so she kind of felt bad for him. He hadn't just woken up, like with a morning wood, had he? Or was it possible that he had a hard-on for her? She liked to think that she was decent looking, having kept herself in shape, especially after her divorce two years ago. Not that she fancied Ryan, although he had been developing into a fine young man, but it sure was a boost to her ego to think that just maybe she was able to attract the gaze of someone younger and more desirable than dirty old men.

When Jennifer grabbed the last two scraps of wood and turned toward the house, there was Ryan, clattering through her gate to join her in the yard. He greeted her, hoping she wasn't appalled at his display of horniness a few minutes ago.

“Hi Ryan, thank you for your help. Should only be a few minutes.”

“It's being neighborly, Miss Prestine. No problem.”

She raised onto her tiptoes and reached up to place the wood on the top of the shelving on the patio. “Oh, and call me Jennifer. Miss Prestine makes me sound old.” She bent down to grab two pieces of metal yard art, placed them on the shelf, and then took the last pieces of scrap wood.

“Okay, sure, Jennifer,” he responded. “Sorry, but it's just a polite thing. You sure don't look old, that's not what I meant.” She looked not just not-old, but pretty damn good, from where he was standing. Even in his fantasies, he hadn't called her Jennifer, but that was probably because it highlighted their age and social difference, making the experience excitingly dirty. He recalled at least twice when he was face down on his bed, naked, trembling, fucking his mattress, whisper-moaning “oh yes, Miss Prestine, I'm cumming, oh, fuck, Miss Prestine,” while stuffing a hand towel under his erupting cock to protect the sheet from his spewing gushes of sperm.

As she reached up to place the scraps on the top shelf, her shirt rode up, giving him a brief view of her bare midriff. She wasn't as skinny as his teenage classmates, but if someone said she was in her twenties, he'd have believed them. Her toned tummy, lack of any kind of muffin top, and curvy but firm hips and ass, got his dick back to stirring in his pants again. By the way she was dressed, he imagined she worked out, or otherwise had some kind of exercise routine. Maybe he should try to find out when, and try to peek in her windows.

“Okay, ready?” She walked over toward the flower beds along the fence, explaining, “I just finished clearing these spots. You can help me carry the stuff in here and I'll show you where to put it.”

Will you show me where to put this? Ryan adjusted his growing cock in his pants, relieved he hadn't said that out loud. “Sure, I'll put anything wherever you want.”

“All right, let's go,” she replied. She had half a mind to tell him that what he just said could be dirty and taken the wrong way, but she kept silent, not wanting to draw attention to it.

Out at the street by the pallets, she tried to move the the big bags of mulch and soil around, determining which she'd need him to carry. The mulch bags were bigger, but lighter, so she tried one of those. He threw a heavy bag of soil over his shoulder, and she hoisted up a bag of mulch. She was able to carry it okay, and decided to continue because she wanted to feel competent, confident, and mostly independent, certainly not wanting to fake the “I'm weak and need a strong man” play.

With three of her trips to each of his two, they got all of the bags to the flower beds and started bringing the smaller trays of flower pots. Little did Jennifer know, Ryan was ogling her. He intentionally broke up his trips such that he could be behind her, admiring that toned ass while it plodded in front of him, excited for the glimpses of the bare skin of her tummy when she bent to pick the bags up and again to place them on the ground.

Lastly, they needed to move the trees. They decided to pick them up by grabbing their pots on opposite sides and sidestepping together. Ryan's eyes studied his older neighbor's tits as she went. When he watched MILF porn, the women were always tall and had big, cushy asses and huge, fake tits, but Jennifer was maybe five-foot-five and fairly slim. And her tits were certainly not DD mature porn-star tits, smaller but still pretty full, just not enough to push out against the stretched material he'd seen in so many videos. She had on a second layer under her tank top, but probably not a sports bra, because her tits seemed supported and jiggling rather than being smashed flat into her chest.

Jennifer felt him looking. She saw him looking. She was kind of repulsed at first, but by the time they were carrying the second tree, she felt a little excitement again. Rather than a dirty old man just wanting to get his jollies, here was a young guy who could probably get his fair share of perfect perky teenagers, who was definitely checking her out, she was sure of it.

“Hold on, hold on, put it down,” Jennifer instructed him, and dropped her side of the pot. “Whew,” she breathed, not really sure she needed a break, but testing Ryan's reaction. She bent down to touch her toes and run her fingers in the grass, half to stretch and half to give him a view down her shirt. Then she stood up straight and stretched her arms over and behind her head, half to relieve those muscles and half to lift her breasts for him.

He noticed, trying not to stare as he caught sight of that tummy again and feeling his eyes tempted by those pert tits.

Fuck, did I really just do that? Jennifer asked herself. I'm not really a fucking tease like this, am I?

His cock lengthening in his pants, Ryan tried not to stare at her jiggling tits as they carried the tree the rest of the way.

“Okay, thank you Ryan,” Jennifer smiled, wiping her forehead with a gloved hand. “I don't know what I would have done without you. Maybe rang every doorbell in the neighborhood.”

“Sure, no problem.” Ryan was looking forward to returning home to his porn, but the thought of actually interacting with a real live woman, even in a non-sexual way, was making him want to stay a bit. By now, he was sure that he'd jerk himself off to thoughts of her later today, so why not feed that fantasy some more images? Watching her bending over and squatting, maybe getting a few peeks down her shirt, would give him some wank material to think about, for sure. “Um, you need some help, like, are you going to plant them now?”

“Oh, I can do it from here. I planned to spend part of the day back here. I think I've interrupted your day enough already.”

“Oh, I didn't know if you could get the trees out, if they were too heavy. The neighborly thing to do, if you still need some help.”

Jennifer was just about to tell him she could easily dig the holes and tip the pots near them and roll the root balls out to drop them into place, but she sensed Ryan was wanting to stay, so she didn't want to deny him that. Maybe he was bored at home with school being out. Or, possibly he was attracted to her? Likely not, though he was definitely eyeing her boobs a minute ago. But he probably eyed every female's boobs – that's just what guys do. She fought off thoughts of having a steamy encounter with the young neighbor boy, but did enjoy the more reasonable thought that in general she still had enough sex appeal to catch the eye of younger guys.

“That's true,” she agreed. “I could put you to work. If you don't mind hanging around with an older woman, if you don't have somewhere to be with some cute girl your age.” She felt stupid the second she said this, like she was reaching.

“Nah, I don't have a girlfriend right now.” He wanted to tell her that she was kind of hot for her age, but didn't know how to say it in a way that wouldn't sound weird or offensive.

“Okay, well, as long as you're willing, let's start with the crepe myrtles.”

He stared at her blankly, muttering something like “okay,” like he didn't know what she was talking about.

“The trees – they're called crepe myrtles.”

“Oh, okay, yeah,” he smiled.

“That's okay, you'll learn. I need you for your muscles, not for your horticulture expertise.” Fuck, I really just said that? she thought as she smiled nervously.

“Heh,” Ryan snickered sheepishly. “I don't know about that, but yeah, I can help.”

Jennifer had one shovel and one trowel. Both of them knew that Ryan's dad just had to have tools as well, but Jennifer didn't ask and Ryan didn't offer, since neither really wanted the work to go any faster. They got the holes dug and the crepe myrtles planted after some time, and started in on the other flowers. The talk was a little awkward, but he did like her anecdotes about being younger and starting life after school, a bit like there were nuggets of advice in her experiences.

Ryan found out that she'd be home during the day all summer, if not into the fall, too. She wasn't working currently, but had income from three rental properties that she still retained from the divorce settlement two years before, enough income to keep her current house while she decided what to do with the other properties and perhaps rejoin the work force when her son got a little older. Ryan learned that the reason her son wasn't around that day was that the younger kids still had two weeks of school left before they were out for the summer.

And Jennifer found herself a little more interested in Ryan, his voice deeper than she remembered, and his work ethic a little more ambitious than she expected. She felt herself having to intentionally try to dismiss a dirty thought now and then.

Ryan set a couple of the flowers in the pits he had dug, but Jennifer had to coach him a bit. “You have to go deeper.” They looked at each other. “Make the hole deeper, dig down some more.” She felt her face redden a bit. They blew off the comment, just for a second, until she followed up with “Here, pull it out.”

They both snickered, knowing full well that her directions were full of sexual innuendos. She shook her head, rolling her eyes, and all she could say was “sorry.”

They replanted the two flowers Ryan was working on, and finished the row. Horny as ever now, he had a had boner in his shorts, and a decent view down Jennifer's shirt as she worked on her hands and knees in front of him. Admiring her ass when she turned a few times, he thought back to at least twice when he had seen her underwear. Not too long before, he was walking back home from a friend's house down the street and saw her bent over in her front yard pulling weeds, her shorts loose enough in the back so that he could see a plain blue waistband. But the first time he thought about her while masturbating was the night of a cookout at a neighbor's house when she was wearing low cut jeans and a short sleeveless top, and every time she went to sit down or bend or crouch slightly, at least an inch or two of her red lacy panties attracted his gaze.

It was early afternoon by the time they finished in the garden. Having cleaned up the debris, spread the new mulch, discarded all the trash, and put the tools away, Jennifer stood with her hands on her hips, admiring the way things had turned out. She wished the “man” with her was “hers” so that she could hug him close, but that would be weird with Ryan. She retrieved her phone from the patio and took a few pictures to post to social media, but she thought it would be best for him not to be in them, lest someone get the wrong idea about the two of them together.

“Thank you so much, again,” Jennifer said. “I could have done it all myself, of course. I'm not just weak and helpless, you know. Well, maybe I couldn't get those crepe myrtles back here, but other than that.”

“No problem, Miss Prestine,” Ryan replied. “Glad to help.”

“Jennifer?”

“Um, right. Glad to help, Jennifer.”

“Come in,” she told him, opening the back door to go inside. “I'll get you something to drink. ”

“Sure, thanks.” Ryan followed her shapely ass into her house.

“I have sun tea,” she said, retrieving the large jar from kitchen window where the direct sunlight had been brewing it since morning. “Or...” She opened the refrigerator, bending slightly to peer inside. “I have lemonade, milk, apple juice.” She felt Ryan's eyes on her ass as she was turned away, but smiled for a few seconds instead of standing up and turning around straightaway. “I don't have any beer, sorry,” she laughed, finally turning and closing the door. “Haven't had any in the house since the days with my ex husband.”

“Heh,” Ryan snickered. “Um, tea would be fine, thanks.”

Jennifer got two glasses, filled them halfway with ice, and poured some tea for them. They leaned against the counter, together, close, and his arm touched hers when he set his glass down. She was pretty sure it was intentional.

“Eww, we're pretty sweaty,” she said. She wet two kitchen towels slightly and handed one to Ryan. They both wiped their arms and faces, cleaning a little sweat and dirt off themselves. Back to downing their tea, they chatted for a minute, neither really wanting to part ways. Ryan poured another glass of tea for both of them. “Well, if I ever need someone to help me pull weeds, maybe hang Christmas lights, I'll know who to call. But next time, I'll pay you, you know, more than with just tea.”

“Oh, you'll have beer then?” It took Jennifer a few seconds, but then she busted out laughing at his joke. Of course, Ryan's cock stirred in his pants, a little more that it had been, thinking, You can pay me with some of that MILF pussy!

“You missed a spot,” Jennifer told him, reaching up to the side of his face with her towel. He hadn't missed a spot, but she just wanted to give him a playful swipe.

It was at least ten seconds later when their lips came apart. Neither one knew who actually made the move, but when their faces backed off from one another, they were both a little shocked that they had just kissed like that.

“Um, oh, sorry, I—” Ryan said, shaking his head, unable to form any more words.

“Oh... ha, I was just about to say sorry myself,” Jennifer replied. “I thought I did that. Did you do that?”

“Umm, I guess.”

“I think we did that.” After a moment to ease the nervousness, she added, “And this.” Reaching her lips up to his, she planted another one on him. He returned the kiss, this time moving a hand up her arm and behind her shoulder.

Without saying a word, Jennifer picked up their half-drunk glasses of tea and led Ryan into her living room. She unstacked a set of coasters and set the glasses on them, settling into the middle cushion of her sofa. She sighed and smiled up at Ryan, who had a noticeable bulge in his shorts by this time.

“Well, if you don't have a girlfriend to get to, and your class isn't till later this afternoon,” she said, patting the cushion beside her. Ryan sat, smiling excitedly but nervously, and moved his arm to rest on the back of the sofa behind her. “I promise, I didn't ring your doorbell earlier just to seduce you. I really needed help with that shit they just left in the street.”

“And I didn't come over just to, well, do this,” Ryan said. “It just kind of happened.”

“But I'm fine with it if you are. I mean, no husband, so it's not like I'm cheating.”

“Yeah, it's fine. I mean, weird, I guess.” He squirmed. “But I liked kissing you.”

“Why weird?” She was teasing a little, wanting to see if she could make him say something about her being so much older.

“Um, I don't know.” He was trying not to say it. “Well, you're my neighbor. And you have a kid.”

“What are you? Eighteen?”

“Seventeen.”

“Hmmm, I'm thirty-six.” She grinned. “More than twice your age.”

“It's okay with me if it's okay with you.” He boldly leaned into her and kissed her again. This time she put an arm around him and got into it a bit more. By the time they were testing out some tongue probing, Ryan pretty much had a full hard-on. He had seen stupid R-rated movies about it, and seen porn about it, but here he was, actually making out with his hot MILF neighbor!

“Well, aren't you excited!” she teased, noticing his obvious erection and placing her hand on it. Running her finger up and down, she told him, “I saw you looking at my boobs earlier, just so you know. You weren't that discreet about it.”

“I'm sorry,” he replied. “But yeah, I mean, they were right there, you know.”

“Hey, you're a horny guy, I get it. And no need to apologize.” She stroked his cock through his shorts a bit more. “It made me know you were interested, and if you hadn't, well, we might not be here right now.”

They made out some more, with him caressing her thigh through her leggings and feeding her more tongue as she stroked and squeezed his hard cock. Breaking the kiss and leaning back with her chest out, she smiled over at him, hand still on his erection. “Come on, you can touch them!”

Ryan had never had such tits in his hand. They were C cups, but he didn't know that; he was just excited about the way they felt. His two previous short-term girlfriends, and one unofficial crush before that, all had smaller tits, firm to the touch and with almost nothing to lift. But Miss Prestine's were softer, fuller, and had some weight to them, providing some substance as he lifted. Groping and squeezing a real woman's tit, tongue kissing her, and feeling her hand stroke his hard cock through his shorts made him moan audibly.

“I don' t think the tea is enough thanks for helping me today,” Jennifer whispered into his ear. By now she was welcoming instead of suppressing the thought of fucking his brains out, but that would be too much for this first time. She really wanted to see that cock, though, so she found the zipper and pulled down on it. “I think it's my turn to … be neighborly.”

Ryan leaned back and let her guide his stiff dick through the fly of his boxers, and squirmed as it popped out. He had only had his two girlfriends feel his bare cock before, and not many times nor for very long, so he had nowhere near the experience to handle the sensitivity. Miss Prestine's fingers felt so good caressing and squeezing it, but he inadvertently tried to pull away.

Jennifer giggled to herself, trying not to laugh out loud to make Ryan feel uncomfortable. His cock wasn't that big, but that's not why she felt this way. It was quite young looking, which made sense, but she came to the realization about just how young. Here she was approaching her late thirties, and this was the youngest cock she'd ever had. When she had lost her virginity and started experimenting with sex, she was in her late teens, and every guy with whom she got to this point was at least twenty.

The dirtiness of jerking off a boy less than half her age got Jennifer even more excited. She spit in her hand to reduce the friction, and smiled at Ryan, who seemed to be calming a bit. “Yes, relax. It's better when it's wet like this, right?”

“Oh, fuck. Yes, that's... uh, good!” He started to pinch the peak of her breast while she jacked him off, feeling the stiff nipple, even through her shirt and bra, contrasting with her soft tit flesh. Her pinkie finger nudged his tightening ball sac and her thumb ran over his dick head as she stroked him steadily up and down. He closed his eyes and leaned back, letting her work his boner. Dropping her face down and toward his cock, she wanted to take him into her mouth, but didn't want to miss seeing the moment of his emission, so she just drooled a blob of spit down onto it. “Oh, fuck,” Ryan breathed as the warm, wet feeling sent him over the edge.

It had been more than two long years since Jennifer had had a sexual experience, but even so, she recognized the moment. Her hand moved a bit faster, making lewd squishing sounds as her saliva coated his shaft and oozed between her fingers.

Ryan shuddered, groaned, and drew in a large breath before exhaling sharply. Jennifer watched a small stream of semen ooze out of his dick hole, followed by a large spurt that splattered his shorts and probably the couch beside him. As she continued to jerk his cock, at least two more gushes of thick sperm flowed out, covering her fingers as he squirmed and sighed.

Opening his eyes, Ryan surveyed the mess and looked at his naughty MILF neighbor, hardly able to believe what had just happened. She was smiling big and giggling, tongue jutting out between her teeth, still squishing her fist up and down his messy slimy cock. “Oh, shit!” he exclaimed.

“Oh, shit is right! That sure is a lot. I didn't know you could have so much bottled up in there!” She got up from the couch and started toward the kitchen. “Stay there – let's get that cleaned up.” She returned with a roll of paper towels and one of the damp hand towels, and the two of them cleaned up what mess they could, from their skin at least. He had to tuck his cock back into his wet boxers, and there was nothing they could do about the cum that had soaked into his shorts.

“My son will be home from school pretty soon,” Jennifer announced. “But hey, it's been fun.”

“Yeah, I have class later this afternoon, so I need to go. But thanks, for... well, you know.”

“Yes, I know. The least I could do for you being so nice to help me with the yard. Don't always have to pay in cash, you know.”

As she walked him to the door, she caught herself hoping she would need some more help around the house or yard soon. With Ryan just next door, their demonstrated willingness to barter could lead to quite a neighborly arrangement.