Pool Boy

Story Info
BBW milf seduces 18-year-old pool cleaner.
4.6k words
3.94
163.2k
23
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"I never thought I'd be a cougar. But there's a certain amount of attention you just can't ignore." Shelby and Brenda were day-drinking in the shaded part of the patio. The sun shone in shimmering reflection off the rippling blue pool.

"Yeah. I know what you mean. But he's at least legal right?"

"Just."

"Well, so that's good. Me, I'm lucky I guess. I don't really have the cougar bug. You know I actually used to worry about it?"

"How do you mean?"

She took a sip of her drink. "I can't believe I'm about to confess this to you. Guess it's what I get for drinking margaritas during the day. But I guess you started it so here goes. I used to worry that I'd grow up to be a lady-creeper. Like Humbert Humbert with a pussy."

"Really?!" Brenda cackled, and immediately lowered her voice, embarrassed at what she heard as a loud, old-lady crack in her laughter. "Why the fuck would you think that? And when was this?"

"So, like, what? When I was sixteen. So like twenty years ago. You remember that line from Dazed and Confused, where Matthew McConaughey says he likes the high school girls?"

"They keep getting younger—"

"And I stay the same age! Exactly! Well that got me thinking—"

"Jesus, is that movie twenty years old? God we are old."

"Maybe not twenty but—like early nineties, right? Anyway maybe I was eighteen already but whenever it was I remember having, like, this very clear chain of logic. Basically it went, (a), a lot of high school-age boys are hot, like, objectively hot, and (b), eventually I would stop being high-school age myself so therefore—"

"God you had a depressing streak even then!"

Shelby laughed. "No but it made perfect sense: Therefore there was going to come a time when there would be like this whole crop of objectively hot guys who were totally off limits forever and ever until you died, end of story, and how depressing would that be?"

"You're depressing me right now!"

"But it has a happy ending, though, at least mine does. Because it turns out it never really happened the way I thought it would."

"What did happen?"

"Like, when I was twenty-three there were totally some eighteen-year-olds who could turn my head, right? But by the time I was, like, twenty-eight? Uh-uh. They just seemed so much like children by then."

"Interesting."

"And the weird part, it wasn't even just the lack of anything in common to talk about. They started to look like children. Like, a guy closer to my age just... looks better to me."

"Yeah. You know I've never thought about it before but I think I've had basically the same experience."

"So now, an eighteen-year-old kid... I mean: nothin'. Not even a tingle. If he don't have graying hair and crow's feet he don't look right."

"Ha!"

"I'm kidding but I'm not, y'know? And it's lucky because, I don't know, I think it really would be kind of torture to just be lusting after kids your whole life."

Brenda was pensive, inscrutable behind her oversized sunglasses. She shifted the paper parasol in her glass in order to access the straw and took a thoughtful sip. Finally she said: "But what about what's-his-name? Grad student—"

"Steve. Yes! Sealed it. Totally sealed it."

"So that was sort of your last hurrah?"

"Well, like, not even that so much as I thought I'd be open minded? Take a chance? Yeah, no."

"And he was twenty....?"

"Something. Let's leave it at that. Anyway, it totally didn't work. He was still smoking pot and you couldn't plan shit with him. He would cancel with like an hour's notice. Sometimes less, like after we were supposed to meet. Infuriating."

"But the body...."

"Yeah, there was that. But no, not so much really. It just felt strange and awkward to tell you the truth. To be with someone so... so unseasoned. I really do like 'em my own age."

"Hmmm. Yeah. I think I know what you mean. Which is why this is so weird for me. I've never experienced this before."

"Midlife crisis?"

"Jesus. Not quite as ahead-of-schedule as I'd like to think, if that's what's going on. But I'm not sure that's what's going on."

"Sounds like you've got a theory."

Brenda drew a deep breath, removed her sunglasses, and placed them atop her straw hat. "You know what I think it is? I think it's the novelty. I mean, the way he looks at me? Jesus! He ought to have semaphore flags!"

"I... don't know what that is."

"Sorry, my navy jargon again. Point is he's really obvious. Just... really freakin' obvious."

"And you... haven't had that before?"

"Not like this. Look, you have to understand, I know there's this age range that all boys go through where they're, like, super-horny. Like fuck-a-drain-pipe horny."

"Sure. Or a pie, like in that movie?"

"Right. And so I think most women, you learn to be a bit dismissive of the attention you get from that age bracket. It's... artificial somehow. They're all on this slightly defective algorithm where their dicks are like little divining rods for any pussy in the room and you just have to realize that your pheromones are going to be a little... a little disabling for a while."

"Or enabling."

"Ha! Good point! Is it kryptonite or is it... What's the opposite of kryptonite?"

"Um. Spinach? But that's Popeye."

"Anyway, you get the idea. Point is there's this phase where teenage boys are walking around with this precarious... meniscus of semen and if you get too close they'll spill some on you."

Shelby had just taken an ill-timed sip from her drink and now craned her head around, laughing through her nose so as not to spray Brenda in the very probable event that her drink exploded out of her mouth any second now. Brenda was courteous enough to wait for the seizure to pass before continuing.

"Well, thing is, thing you might not realize is that when you're a fat chick—"

"Oh, Brenda, you're not—"

"Shelby, please. Come on. Don't. I do own a scale you know."

"You're voluptuous."

Brenda ignored the compliment. "When you're shaped the way I am you really don't get as much of that. Like, even when they're at peak horniness. They ignore you. In fact, I think it was worse when I was younger."

"Really? Why'd you s'pose that is?"

"Well, funny you should ask. Because it turns out that I have given this way too much thought. And I chalk it up to two things. One. When you're closer to them in age it's like the fat is a genuine flaw. When you've got a few years on them they can kind of bundle the fat into this larger sort of, sort of milfy fantasy they're composing for themselves and just imagine it goes with the territory. You're not fat because you're really fat, you're just fat because you're old. Something like that."

"Hmm. Not sure I buy it. But two?"

"Two, I think fat women are becoming more eligible right now. It's some kind of... national... trend in sexuality or something."

"My stylist was saying that. She's, you know, plus-sized, and she was saying it's starting to become okay. Like, where she used to always have guys wanting to hook up with her but then not want to really date her or whatever, now it different...."

"Fat is the new black. Lucky me."

"I think it's the internet."

"I try not to think about it."

"I mean, I think there's all these, you know, fat appreciation sites..."

"Seriously, don't." Brenda shook her head. "God, he wants me for the novelty."

"Well I don't know about that. I mean I think what you said before about the horny stage—I'm sure there's a lot of that in there. But just because guys are starting to like... bigger women, that doesn't mean it's like some new and different thing for him. Maybe it just never occurred to him not to find you attractive." Brenda sighed heavily, and Shelby noticed. "This is really weighing on you, isn't it?" she asked.

"Meh. It's just... like I said: surprisingly hard to ignore."

"Well, you know what they say. Supposedly we're at our sexual peaks right now too, whereas boys it's like eighteen. So you and him are both peaking right now."

"Oh, Jesus, that bodes well!" she shook her head with a shudder.

"Well, it isn't like it's already happened. When do you see him next?"

"Tomorrow at ten. Unless I hire a different pool cleaner by then." She shook her head again and, with another shudder, exclaimed "a fucking pool cleaner, can you believe it? I mean: It's the plot of a porno for God's sakes!"

"Ha! Don't feel so bad. I mean, those clichés have to come from somewhere. There's a UPS guy comes to reception in my building? Like half the phone pool's rubbin' out to him I swear. Nothin' subtle about it. And that's like straight out of pornos."

"What are you doing at ten tomorrow?"

"Sorry. Nails. You're on your own."

"Jesus, what am I gonna do."

"I think you're gonna do what you want to do."

"In my experience 'what I want to do' is a moving target."

"Well then step out for Starbucks at quarter of. Or else... just try to keep it in your pants, homegirl."

Both laughed as Brenda poured the remains of the pitcher into their glasses.

* * *

The next morning, nine forty-five found Brenda face-down on her raft, bikini top unfastened in the morning sun. By the steps beside the pool her iPhone chimed the marimba tone she's been too lazy to change. She paddled over to the steps, blotted her hands on the folded towel, and retrieved the phone. "Brandon," read the alarm screen.

"God," she sighed aloud, thumbing the alarm off. "Brandon and Brenda. Everything about this is ridiculous."

She fastened her top, emerged from the pool, and drew on her floor-length white bathrobe as she stepped into the cool dark house. She went to the bathroom and sat down to pee and then, standing up, regarded herself severely in the mirror. Her blond hair was dark and stringy from having been defiantly dunked in the pool, the better to look a disheveled mess when her horny little admirer arrived. Her makeup was washed away and her freckles shone, as did her wrinkles. In the bright light of her dressing lamps, she looked all of her thirty-five years.

Her e-cup breasts hung heavily in her bikini top, which offered only concealment, no support. The remnant of her hourglass required increasing doses of self-deluded imagination to spot in the mirror as her belly, formerly overshadowed by her always large bust and backside—what Shelby would flatteringly call her "voluptuous" parts—had lately grown more assertive and begun to elide her womanly shape.

Over her shoulder things were equally discouraging. Her bottom, though large, could still be packaged sexily, crammed into jeans, say, presenting an illusion of buoyancy. But beneath the crinkly surface of her wet green bikini bottom, the hail-damage cellulite where buttock moved imperceptibly into thigh struck her as objectively unsightly. This Brandon kid—what they hell was wrong with him anyway?, she wondered harshly.

She experimented with the bathrobe: Tying it off had the virtue of concealing more skin, whereas letting it hang loose had the desirable-under-the-circumstances effect of further obscuring her curves. It looked like a cross between a muumuu and a hospital gown. She attempted a kind of compromise—a loose knot that would cover more without losing the flattening effect of the draped fabric, but nothing seemed to work, so she just decided to tie it.

At last, she stepped onto the scale, and waited while the dial settled in at 275. Well, she thought, five of that had to be water and robe. Just then the doorbell rang. Now, if only I had rollers to put in my hair.

She had succeeded in making herself feel so profoundly unsexy that it caught her a little off-guard when Brandon's face bore that same stupid mix of pleasure and hunger at the sight of her that it always had. "Hello, Ms. Parker," he managed with his dumb horny grin.

"Hi, Brandon. You can go on back. Come through the house if you'd like or, side gate's open if you need to get at your truck."

"Thanks, Ms. Parker. I'll just go around."

She watched as he walked out toward his truck. God but he was pretty, she had to admit that. He had an improbable combination of coloring—over blue eyes he wore a scrub of close-cropped blond hair bleached white by the sun, atop an olive-tinctured skin that took a tan too easily, without any evident reddening. He wore a white polo shirt with the pool company's logo embroidered on it, and tight khaki shorts that flattered his taut physique, especially his dimpled gluteals, the focus of her gaze now as he walked away.

These same muscles were the center of her attention when, five minutes later, she found herself crouched at her bathroom window peering out through a crack where she held up a single fauxwood blind. His back was to her and, as he worked the net back and forth across the surface of the water, she admired the gentle rippling of calf and hamstring and buttock.

"What is it about boy ass?" she'd once propounded to Shelby. "I mean, girl ass is a target, right? Men have ancestral memories dating back a gillion years from before there were even monkeys, back when doggy style was the only style if you were a mammal, so men basically arrive in this world preset and hard-wired to seek out that round shape. But what is it we see in their bony butts? What's the point?"

In reply Shelby only blushed a deep crimson.

"What?"

"I think I know," she said, suppressing a giggle.

"What?"

"A man's ass is his engine," she offered. "A guy's fuck is in his ass." Whereupon the two of them guffawed heartily, and in a most unladylike way.

She cracked a smile on remembering this conversation, but it wasn't just amusement she was experiencing. She felt a giddy twinge of arousal as she contemplated the truth of it, here in the presence of Brandon's statuesque "engine." It was a very short step from the back-and-forth motion he was performing right now to... she tried to avoid the thought but it was too late. In her mind's eye she already had his lithe, supple, muscled form, warm from the sun, stepping up behind her, easing aside her bikini bottoms and... without thinking she reached down and dropped a finger into her pants and drew a circle around her swelling clitoris.

Jesus, Brenda, what the fuck are you doing? She withdrew her hand and let the blind shade fall. Grow up! She scolded herself. She started to move away from the window but then froze. She began what was unusual for her, a fully articulated conversation with herself in her mind—an actual dialogue of the kind an old Warner Brothers cartoon may have illustrated with an angel and devil on either shoulder. Wait, she said to herself, if you fucked him, that would not be grown up. But this? This is a bit naughty, sure, but what's the harm?

 

What if he sees me?

 

What if he sees your eyes through a sliver in the window? And figures out that you were jerking off? Come on. Give yourself this. It's harmless and you deserve it.

 

So she did. She stooped at the window again and began administering those steady, boring, up-and-down strokes that had so reliably gotten her off for about as long as she could remember—never as intensely as actual sex (when actual sex worked) but far more quickly and consistently. The efficiency of her touch combined with the excitement of this sort of reverse voyeurism (she had never masturbated where the object of fantasy was right there, physically present) was working very quickly—she was more than half-way home and wanted to slow down in order to savor this.

She wanted to imagine him behind her, so, although it required bending sideways awkwardly, she reached around behind her own mighty bottom and put all four fingers of her hand into her now-dripping slit. She felt shudders of pleasure as she moved her hand in and out, jiggling her backside. She enjoyed this new sensation, less certain of producing orgasm than her targeted clitoral attack, as a better simulation of what she would experience with young Brandon.

Happily, she reacted in plenty of time when Brad began to turn around. It had to happen sooner or later—he wasn't going to clean the whole pool standing in that one spot. And when he began to rotate she instantly dropped the blind and backed away from the window. But now she did not want to stop.

She double checked the lock of her bedroom door and flopped back on the king-sized bed. She imagined him collapsing down on top of her as she held her legs high in the air. She knew better than to worry that he would come poke his head in—the doors were locked and, anyway, he was too polite and deferential—but prudence seemed to argue in favor of getting this over with, so she reverted to her fast, efficient vertical stroke, the old standby move in which she would move her foremost fingers up and down, up and down, grazing the clitoris and just breaking the plane of the labia, gathering just enough moisture to lubricate the stroke.

As she drew near the end she reached her free hand under her top and circle a hardening nipple just in time to push her over the edge. Her breathing became jagged and, despite her best efforts she whimpered audibly as the contractions took hold of her. An ungodly large secretion quickly flooded her bikini bottom and mingled with the pool water that had already dampened her duvet cover.

She exhaled a big lungful of air and then mentally counted down from ten, forcing herself to spring to her feet on reaching zero, and moved quickly to the master bath to cleanse her hand of sex smell. On arriving in the bathroom she decided first to risk another peak out the window and saw the blond boy wonder squatted beside the pump with his little rack of plastic chemical tubes. She knew from past observation that this procedure took place near the end of his routine, so she would have to reappear soon.

She began to run the water and caught a glimpse of herself in the mirror. Her eyes were aglow, her lips plump, her cheeks red. She turned off the water and, in a hasty maneuver, tied her hair up in a tousled but not-unsexy bunch, and administered precisely one puff from one of the perfume atomizers arrayed on her mirrored tray.

She sprinted out to the kitchen and began preparing a pitcher of lemonade. Lemonade?! Seriously?! Jesus¸ that's grown up!, she chided herself, before telling herself to shut up. When the batch was made she paused over the ice tray before—I can't believe I'm doing this—plucking out one last ice cube and slipping it briefly under each cup of her top, making her jump as each nipple responded to the cold by swelling erect. She let the bathrobe hang jauntily open as she made her way outside with the tray, just as Brandon was finishing up.

"Oh, thanks Ms. Parker. You didn't have to do that."

"We're shaping up to have another scorcher. Have to stay hydrated."

"Thanks," he repeated.

"Sheesh, speaking of," she shed her bathrobe, shrugging and pushing her shoulders back exaggeratedly, the better to push her breasts forward. She pretended to look down but in the corner of her eye registered that Brandon was staring at her nipples. "I am sweating like a pig in this thing." She draped it over a deck chair.

"Oh, Ms. Parker, you shouldn't say that. You are not a pig."

Brenda suppressed a wince. But he's such a pretty idiot, she assured herself. "Oh, um, thanks, Brandon. That's, uh, sweet of you to say. So, uh, what were you doing out there with the chemicals?"

"Oh I was just testing the levels. We have to look at the pH level and the total alkalinity or what they call 'TA'."

12