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Carly and Jack aim for a personal record for most orgasms under her feet in a single day.

            “Five,” you heave gracelessly as you send another load into the squishy void. Your clammy limbs flail momentarily in the darkness before being pinned back beneath the mammoth weight of Carly’s colossal toes again.

            It’s been a long time coming; it’s taken you the better part of a half hour to coax another orgasm out, considering how tricky it’s been to get a grip on your erection in the pounding pitch-black and disorienting pressure-cooker space. Your aching member begins to wilt almost immediately following this latest jacking against the velvety, gridded underside of your giant sister’s foot. Gulping for air, your heart pounding mightily in your tiny chest, you let your face fade back into the crevice between the girl’s titanic big and second toes, letting the fleshy grooves massage you back into coherency.

            Her digits are only too happy to reciprocate, hugging you into the fray. Again and again you’re mashed up against the bucking ceiling of doughy toes until at last she claps you down against the base of the shoe again. You know what it means, of course. There’s nothing you can move but your neck and your jaws. Opening your mouth and pressing it against the undulating mass of feminine skin is the only choice.

            So you lick. Tongue lapping obediently at the curved wall of sticky, salted flesh, you feel your lungs steadily refilling with her humid air after the exertion. No doubt about it, you can’t beat the workout you get from these “assignments” Carly gives you every morning before lovingly laying you down in the mushy insole of her shoes and clobbering you into the corner with her incredibly sociable toes, all squirming and wrestling for the opportunity to dominate your hapless body.

            She’s going to be disappointed. Not mad, certainly, never mad anymore, but disappointed, which is quite possibly the worst outcome you could experience in her presence.

            Your sister deserves nothing less than to be the happiest owner in the world.

 

            Carly’s chosen the single-occupancy restroom with its blindingly lime-green tile and startling low echo effect to remove you from her shoe for a break.

            This place is normally reserved for staff, but virtually never used: a favorite resting place for Carly during the day when the dormitories are far off and she feels like checking on you. You’ve come to enjoy the little rests, watching the laugh lines in her adorable, enormous face creasing at the sight of your nearly three-inch nude body coming back into the light. It usually takes a minute for you to adjust to the blaring glow after so long in the darkness, but it’s always worth it to see the look on her face.

            She genuinely is happy to see you, just as you are her, and you can’t say you often see that look in her eyes gifted to anyone else in the world, at least not on accident. That joy is reserved for you, and you alone.

            Is there anyone luckier in the entire universe?

            “Well?” Carly queries cheerfully as she brandishes you between her thumb and forefinger, letting your exhausted body drape gratefully over her firm digits. She massages your back with her pinky, digging at the soft knots formed after your excursion. “How many times did you cum?”

            “F-Five,” you announce, unable to hide the trace of shame from crossing your voice, in spite of your excitement to see her again.

            “Five?” she repeats back, blinking in puzzlement. Her fingers open up, allowing you to tumble back into the soft awaiting palm below, where you become splayed out, as if spreading a snow angel into the expansive plain of tanned skin. You notice those oceanic baby blues squinting, zeroing in on your weary junk, examining for potential problems.

            “Uh-huh,” you gulp.

            “Is something the matter?” she says with obvious deep concern etched into her forehead as she draws back again. Her lower lip puffs up and curls into her teeth as she thoughtfully chews it. “Yesterday you had eight by this time. It’s lunchtime already.”

            “I know,” you grumble, bowing your head and shutting your eyes as you allow the cool, sterile air of the bathroom to wash over your overheated skin.

            “Is my little bro’s cute little cock getting tired already, hmm?” Carly’s thumb appears over the crest of her palm. Delicately she dips under your pitiful dick and props it against her finger for a better look.

            “A… a tiny bit, y-yeah. I’m sorry.”

            “Don’t be sorry,” Carly chuckles, shaking her head. A few wisps of that luscious golden hair sweep over your chest from on high. “I know I’ve been using you a lot like this lately… what, the last three days?”

            “Four,” you correct, a dumb grin unavoidably crossing your face.

            “That’s a lot of time fucking my pretty toesies, isn’t it, little bro?”

            “Uh-huh.”

            “Yes it is,” she confirms in that cutesy-baby voice she so enjoys using on you. It used to be a sign of condescension, to remind you how little you had become, but now it just feels more like a precious reminder of who’s wearing the shoes in this relationship.

            “I don’t mind,” you gulp. Grimacing, you shoot a glance to your tired member, still undergoing a gentle prodding by Carly’s enormous thumb. A shudder shoots up your spine, in spite of yourself, at the direct attention paid it. A few millimeters of adjustment allows Carly’s skin to grind up the length of your rod, and you can feel it reacting again, lengthening, no matter how sorely.

            How typical. Then again, given Carly’s voracious appetite for sexual offerings, you’re probably better off having such an eager libido.

            “Maybe we should take a break from going around like this, huh? Maybe I’ll just stick you in my purse,” she suggests as she feels your member shivering under her finger, flashing you a wink. She presses her digit down flush against your dick. “I can reach in and fiddle with you the whole class period. Wouldn’t you like that?”

            Tempting as it is to imagine your gigantic sister’s twinkling eyes and broad, smirking lips filling up the zippered barrier from within her purse, followed by probing fingers arcing in to clutch you by the balls and overcome the boredom of a class lecture, you don’t want her to be making concessions for you. Not when you’ve come this far.

            “P-Please?” you beg softly just as Carly’s hand begins to shift down toward her deposited handbag. “Please give me another chance?”

            “I don’t know how you’re expecting to get that many more out when you’re only at five by now…” Carly sighs with a forgiving shrug, furrowing her brow in continued befuddlement at the exceptionally low number. The pink blush of her lips flows from one end to the other as she nibbles the opposite corner in contemplation. “Maybe I’m expecting too much. You’re just a little boy, after all.”

            “I know,” you say. You wrap your hands around your sister’s gigantic finger as it continues rhythmically kneading your crotch. Warmth floods just beneath your skin.

            Carly chuckles, ruffling your hair with a finger on the opposite side of her expansive palm as she lets you hug her thumb. Her chin tilts lower down toward you until her hot breath steams against your skin, collecting in her cupped hand. You’re surrounded on all sides by stroking fingers and your sister’s titanic lips.

            “Tell you what,” she whispers soothingly. The tip of her tongue laps out from the corner of her lip and drags a line of saliva along the lower rim. “I’ve got a compromise.”

            “Compromise?”

            “Mm-hmm,” she hums mischievously. “I’ve been expecting you to do all the work yourself, when you’re down there in between my toes and you can’t see or hear anything. I think I owe you a little help now.”

            “S-Sure,” you huff, your breath getting shallower already as Carly continues teasingly squeezing at your minute cock. The little thing, even fully erect, is swallowed up at embarrassingly proportion by the pads of your sister’s loving fingers.

            “But not yet,” she giggles, abruptly releasing her gentle grip on your junk. Your body sags almost immediately in her palm, pre-emptively disappointed.

            “Okay,” you grunt. It takes a second of readjustment to avoid feeling the painful tug of blue balls.

            “I’ll talk to you after lecture,” she says with a wink. A final tousle of your shaggy hair and you’re being lowered in Carly’s caged fingers back down toward the sickly green tile floor. Her foot writhes inside her shoe until her heel breaks free with a quiet pop. The girl’s sole arches up, beautiful wrinkles glinting off the bright reflection of the floor, while her toes press up from the bottom, creating just enough space for you to be wedged inside.

            And wedged inside, you are.

 

            A shift. Your sister’s damp sole flesh peels away from your body.

            Light leaks into the cramped, sweaty habitat of Carly’s shoe sooner than you were expecting. Is her class already over? The glow isn’t quite as dim as the lamp in your sister’s dorm. It fills in the soft creases of her steadily arching foot, shadow and dark peach. You’re mesmerized, as always, by the chance to witness this dance of her skin, and she knows it. She’s inviting you for a closer look.

            Pinned as you are beneath her toes, you can pull yourself just far enough in this newfound space to get a front-row seat to the show, until most of your body is hunkered under the ball of her foot.

            No fingers come in to collect you, though, as they usually do. Nor does Carly’s foot begin to slink out of its muggy prison, with your naked body clamped between her toes.

            That’s when you hear the voices. A distant, droning timbre rambling through the finer details of a sports psychology textbook. Nearer, the whisper of younger voices under breath. Scribbles of pencils. Tapping of keyboards. The clack of fingernails touching phone screens under the table and out of view of the professor.

            Your heart leaps into your throat. She’s still in class! Carly’s pulling your foot away from the shoe, and she’s still out in the open! Her heel’s risen high enough now that if someone were to, say, lay on the floor and glance in the direction of her playful peds bouncing in the shoes which, frankly, is what you would be doing if you suddenly flashed back to normal size, they would probably see you. They’d see a nearly three-inch nude boy: sleepy, mildly aroused, and painted in layers of his sister’s gummy sweat.

            Rapidly you try to crawl backwards, seeking shelter under your sibling’s marvelous dabbing toes, but you’re not allowed. Another shift. Her toes flatten at the tip. The ball of Carly’s foot is still poised over your torso, and she applies just enough pressure to keep you pinned. You feel your back sinking into the soggy basin of the insole while your sister flushes you under the rotund weight of her foot.

            What is she doing? At least most of your body is hidden under her foot where it belongs, but your head is still visible. Luckily, the floating shadows of her continually arching sole conceal your face for the most part, but every few seconds, light shines over your head.

            You’re exposed, even if only slightly. Vulnerable to the average human beings out there, fully dressed and fully sized, with their own lives and agendas, having their desires only occasionally taken care of while never catering to the needs of something greater than themselves.

            You can’t help but feel sad for them all. It must be a staggeringly pointless existence.

            As if to drive home the point of your pondering, Carly’s toes move again. They squirm, expertly rummaging your legs underneath them until you have a leg splayed under your sister’s mammoth second and third toes. As usual, all you have to do is remain still and comply.

            With the continued sliver of a risk playing tricks with your vision beyond, the sight of your sibling’s hot sole buckling above, Carly’s toes grasp your dick in between with the most impossibly soft touch.

            An airless gasp slips through your lips at the tingling contact that so adeptly strokes the slender walls of Carly’s practiced toes along your member. She doesn’t give you a rest; again, the canyon of slick female flesh coddles your dick. An erection sprouts up within four passes.

            She was right. All you needed was a little help.

            With this change-up in the pattern, granting you not only fresh air but he heart-pounding fear of being discovered mixed with your own mounting arousal, it doesn’t take long. You spurt into the deep crevice of her toes, careful not to let too loud of a sigh out.

            A pause. Carly’s toes separate as far as they can, splayed out and rubbing down on your bare legs as she grants your cock a reprieve. Aching and bursting with sensations, you huff the sweet-and-sour air emanating from her sole above. On its next dip, you stick out your tongue and lap up a fresh line. Her toes scrunch in thanks around you, but remain steady.

            Forty-three. Forty-four. Forty-five seconds, and with a start, Carly’s toes collide with such force and still scientific focus around your dick. After so many years and so many games, she knows precisely when you become useful again.

            The masturbation is more fervent this time. While the last was just a warm-up, coyly coaxing your sixth orgasm of the day, she means business now. You can feel the shoe rocking up and down now, powered by the tips of her toes, even while two of them remain wrapped around your microscopic member. They work faster now, and even if you felt tired a moment ago, your body doesn’t quite agree. It’s standing at attention again with the minute.

            The ball of her foot hammers down against your torso now, compressing the air in and out of your lungs, pumping and controlling your already heavy breaths. But you trust her, and know she understands exactly what she’s doing. She can play you like a harp. If anything, this will help, timing your exhalations with the thrusts of her toes. Her heel bobs against the mouth of the shoe.

            Another countdown. You can feel she’s eager to continue this time, her toes twitching as they play at your thighs, itching to clamp back around your crotch. Sweat is running in rivulets down your back, while fresh supplies trickle down the gorgeous creases continually folding and flexing above you in Carly’s sole. The drops wash over your face and through your dry lips, tempting you with their spice, tainted by only the lightest of strawberry lotion flavors while the rest of it is pure flesh and salt: ragged, animal essence of your sister’s godlike body.

            Your body shudders. The seventh climax comes more quickly than any of the others today.

            The awful forty-five second break ends with aplomb as you feel the toes closing back around your already rising member. The ridges of Carly’s sole meet your head as she seals you back inside the shoe this time, happily mashing your face between sticky insole and blushing skin. It’s impossible not to plant a hard kiss on her flesh every time it massages into your head while her toes swallow up your cock. Number eight is fast approaching, and you doubt your sister will be finished with you after that.

            The both of you just might break the record today after all.

 

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