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Story Notes:

This story was done as a commission.

As you can probably guess from the tags, this one is for the boob-men (and women) in the audience.

Interested in commissioning me for your own custom story? I can write your ultimate macro fantasy, from a wide range of genres and lengths. Read details here: https://thejacksmith.deviantart.com/journal/Story-Commissions-698491757

I also have a side-shop for miscellaneous pre-written & discounted goodies, such as flash fiction, unfinished tales, and deleted scenes from series like Time-Out and A Little Blackmail. Check it out here: https://www.deviantart.com/thejacksmith/journal/New-Special-Stories-Shop-802615692

Karen Delmonte settled her juicy thighs down against the slats of the poolside recliner and crossed her bare legs at the end, letting the warm summer breeze dance across her whole body, from between her toes to the strands of her long bombshell-blonde hair. The rubber stripes of the seat buckled slightly under the roomy mass of her pearly-white ass cheeks, tight and rounded despite their jiggly volume.

            Getting cozy now, Karen chuckled to herself and casually ran a fingertip over the high curves of the twin hills that formed her enormous buxom tits, for the time being contained in a red-and-white polka dotted retro-chic swimsuit top, matched by the corresponding bottoms wrapped taut around her ample caboose. Like her pale butt, her girls were firm yet wobbly, and dotted with numerous freckles that hinted at her mature age but also, Karen felt, acted as beauty marks upon her gifted cleavage. Her hand traveled from the side of her boob down her abdomen, by no means a washboard but not oversized either, then over the noticeable slope that transformed into her hips. It was just lucky the poolside chair was wide enough to fit her generous broad-set hourglass frame, or the bawdy golden-haired milf might’ve grown uncomfortable during these lazy summer afternoons spent by the water with her best-friend-slash-next-door-neighbor Alison.

            Today the pair were just settling in, each with a mimosa in hand, to chit-chat over the latest reality TV and gossip about slutty neighbors. Though Karen enjoyed spending this time with Alison, she increasingly savored the chance to flaunt herself by the pool thanks to a shift she’d begun seeing in Alison’s son Derrick.

            The boy, now eighteen, had always been a quiet shy thing, which the conversely boisterous and sociable older woman loved to exploit by teasing and complimenting him, just to see his cheeks burn red. This year in particular, however, Karen noticed Derrick blatantly gazing at her, especially when she was dressed this way, her tits out to play and accented by the polka dots, her eye-catching ass slung in a lawn chair, with the sun and a fashionable gleam of muggy perspiration on her luscious skin. As a woman who’d spent her youth toying with thirsty men like it was a sport, but now having semi-retired from that lifestyle, it was a secret thrill for Karen to display herself and keep Derrick dangled on a metaphoric string, as his obvious lack of romantic or sexual experience had led him to desperate perving on the neighbor.

            Which he just so happened to be doing at this precise moment. Derrick, scrawny and awkward as he was, had no concept of subtlety, and was standing at the porch window, peering between the blinds with a pair of binoculars. Thinking he was concealed by the shade, he studied all of Karen’s luxurious shape, especially those desirable tits. Though he couldn’t hear the conversation between her and his mother Alison, it was always a treat when Karen broke out into lyrical cackles, which was often given her raucous personality, thus causing her breasts to bounce and quake. The sexy middle-aged blonde never once looked directly at him, but kept her attention seemingly squared to her best friend, sipping her drink and occasionally tugging her swimsuit shoulder strap or giving her hair a toss. Had the boy realized that the crafty woman was in fact almost-exclusively focused on the horny teen peeping on her from inside the house, and not only appreciating and deliberating on this fact, but also scheming how to use his interest in a way that both entertained her and taught him a life lesson, Derrick might’ve sprinted to his bedroom and never looked at Karen again. But he didn’t.

            Three mimosas in, the magical milf was feeling adequately bubbly. She lit a long cigarette between her teeth and took slow drags, continuing to converse with Alison, but now cast intermittent glances to the porch window. Worried of being exposed, Derrick backed off and hid his binoculars, just as he received a text from his mother.

            Come outside and say hello to Karen, it read.

            Gulping, the boy waited a moment to open the door so it wasn’t obvious he’d been standing right there. Then he shuffled out, walking around the pool to the opposite side where his mother and the next-door-neighbor awaited. Karen puffed on her cigarette and breathed it out in a dramatic wisp, alternately crossing her legs and smiling in greeting.

            “Well, hello there, Derrick,” she purred.

            “H-Hi, Mrs. Delmonte.”

            “Oh, honey. For the sixteen-thousandth time, I haven’t been a Mrs. since that penny-pinching second husband of mine, and I don’t intend on repeating the mistake anytime soon,” Karen groaned, rolling her eyes, but also sharing a side-giggle and a clinking of glasses with Alison. “You’re to just call me Karen, remember?”

            “Sorry. Um, hi Karen.”

            “Hi, Derrick. Why don’t you take a seat and join us?”

            Nervous, the teen sat on the only remaining pool chair beside Karen.

            “Good boy. Now, would you care for a sip?” she offered, holding out her half-finished mimosa.

            Derrick’s eyes darted between Karen’s serious conviction and his mother’s stern expression. Before he could decide to accept it or not, though, both women burst out laughing, especially the blonde visitor, with piercing peals of lilting sound that echoed through the whole suburb. Still, he couldn’t help sneaking a peek at Karen’s cleavage in motion as her arm reached out to him, then retracted once the jig was up. New freckles seemed to emerge right out of the divot between those meaty globes.

            “Relax, sweetie. I’m only pulling your leg. You know your mother would never let me hear the end of it if I started a nice clean boy like you onto my bad habits. Have you got any bad habits, Derrick?” Karen smoothly continued, taking a slurp from her drink.

            “I, uh, don’t think so. I hope not,” he fumbled. Of course all he could think of was his tendency to “bird-watch” the neighbor ladies, and none more feverishly than Karen herself. It was getting harder and harder to keep his eyes locked to hers, rather than exploring her half-naked body, full and lush and glistening in the summer heat.

            “None? Well, you must be some sort of saint, then,” Karen snickered. Setting her drink down, she held the cigarette by her full pink lips, taking another drag and dabbing the ashes into a tray on the table. Derrick couldn’t help but fixate on the pink lipstick stain smudged in a halo around that paper cigarette, now hovering just a short distance over the fleshy gulch of the woman’s magnificent pair. “A young man like you. Strapping, smart, handsome, cool under pressure, and no bad habits? You must be a real hot ticket for all the girls at school. I’ll bet they just can’t keep their hands off you.”

            Derrick fidgeted. He was basically none of those things, and Karen knew it. Still, despite his clumsiness, the combination of this intoxicating up-close view of her bathing suit bod, plus the woman’s domineering personality just batting at him like a cat with a mouse, and the boy started feeling warm. Tingly, even. This was so not the time, but his biology didn’t know.

            Lost in thought, Derrick was startled abruptly when the straps of his chair snapped in unison, causing him to fall off in surprise. He didn’t notice the motion of Karen’s spellbinding fingertips.

            “Be careful, Derrick,” Alison warned. “Now we’ll have to get that replaced. Another reason why you shouldn’t be tasting adult beverages yet.”

            “S-Sorry. I don’t know how that…”

            “Whoops! Well, that’s a pickle, isn’t it?” Karen laughed. “No more chairs now, hmm? And we were just starting to catch up, too. What a shame.”

            Derrick stood up, preparing to make his quick exit before this got weirder, but suddenly found his wrist captured in Karen’s hand.

            “Leaving so soon? There’s no need to leave on account of cheap building materials. There’s plenty of room in my seat dear, see? Why don’t we just share?”

 

Chapter End Notes:

A little buildup before the size-changing. More to come soon.

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