Miley Gets Regressed Part Four (Patreon)

“We always like to greet our new arrivals with a little check up,” Alice Smythe said with a sinister smile. Settling herself into a comfy chair near the changing table, she looked at Miley and beckoned. Reluctantly, Miley shuffled across the room, unconsciously tugging at her onsie at the back to stop it from bunching up uncomfortably. The onsie was just a little tight and made from a stretchy material... it clung to her body and accentuated her womanly curves as she padded over to stand nervously next to the head matron.

     “Come here,” she said, patting her lap and looking up at her expectantly. Miley stared back, eyes wide, her heart pounding in her throat. Slowly, hesitantly, she complied, lowering herself into a partial prone position across Ms. Smythe’s thighs. Without hesitation, the head matron took Miley under the arms and pulled her firmly into position, her full weight supported by the older woman’s warm, firm lap. Suspended in the air, her feet dangling inches off the floor behind her, she shot a look of fear over her shoulder when Alice patted the plumply padded seat of her onsie before reaching between her legs to unsnap them. The wide, puffy seat of her pampers came into view-- Ms. Smythe chuckled, and she reached around, carefully pealing the tapes open before folding it down to reveal a jiggling bare bottom.

     “NNNOO!” Miley squealed, kicking her legs and clenching her buttocks. “You can’t spank me!” she said, bratty and defiant, reaching back to shield her butt with her hand.

     Ms. Smythe easily gathered Miley’s wrist into one hand and pinned it at the small of her back, effectively trapping her in place. “Rest assured, young lady, that if I wanted to warm your bottom, I would have you crying your little eyes out by now,” she assured her charge confidently, delivering a handful of open palmed swats to each delectable buttock, making Miley scream and kick and writhe helplessly in place, and she had no doubt that Ms. Smythe absolutely meant what she said.

     “You should be thankful that you’re not in for a spanking... at least, not yet,” she warned with a tight smile. Reaching into a nearby drawer, she removed some small objects.

Miley sagged when she heard she wasn’t in for a spanking, relieved. But if I’m not here to get a spanking, she thought, wriggling uncomfortably over Alice’s lap, then how come I’m laying here with my bare ass hanging out?  

Peering over her shoulder only netted her further questions when saw Ms. Smythe smearing a glass cylinder, about the circumference of her thumb, with a clear, gel-like substance. Her suspicions were confirmed when, moments later, Ms. Smythe, utterly without warning, squeezed a glob of the jelly onto her forefinger and stuck it between Miley’s butt cheeks and began smearing the wrinkled pucker of her delicate little anus.

    “Whoa! Hey!” She squealed, her feet fluttering urgently in the air behind her. “Just what do you think you’re doiiIIIIIING!” Miley gave a surprised, mortified squawk when the head matron suddenly pushed her finger inside her, the tip disappearing with ease right up Miley’s tight little asshole.  

     “Hold still young lady,” Ms. Smythe said absently, easily pinning Miley down in her lap and thoroughly greasing up her back passage. Miley wiggled and fought for a long moment before the finger was slowly withdrawn.

With a sigh, she relaxed, hanging limply over the older woman’s lap, breathing shakily... at least she had that part over with. But now she felt Alice’s steely fingers gripping her buttocks to spread her cheeks apart once more, and Miley blushed, conscious of the cool breeze across her greasy, glistening anus. A hesitant peek over her shoulder revealed the bulbous cylinder of the over-sized thermometer currently bearing down on her butt-hole.

     She tensed and tried squirming away, but with her wrist locked in place behind her back, Miley was utterly powerless to stop the headmistress from pushing the chilly glass tube of the thermometer past the quivering crinkle of her anus and firmly into her rectum.  

     “GGGUUHH!” She grunted, kicking her legs in the air behind her and clawing at the carpet with her free hand. Ms. Smythe just chuckled, holding her in place with one hand while patting her smooth, bare rump with the other. Miley settled in with a shaky sigh, trying to focus on anything-- the warmth of the head matron’s lap beneath her, the chilly air of the nursery on her naked,  goose pimpled flesh-- anything besides the embarrassing sensation of the cool glass tube that had been shoved up her well-lubricated anus.  

     “There we go!” said Ms. Smyth, her voice sickly sweet, patting Miley’s soft pink buns with her palm.

     “Hhhhuhhhhh!” Miley groaned, her legs scissoring wildly in the air behind her. She was vividly aware of her ridiculous position-- laying across the attractive head matron’s lap, her bare rump thrust up proudly into the air behind her, over-sized baby thermometer protruding from between the pleasantly plump hillocks of her buttocks. Her anus, stretched tightly over the cool glass of the thermometer, quivered ticklishly, and inside, her rectum pulsed wetly, tightening and loosening around the smooth glass cylinder at regular intervals, making her writhe and squirm.

Worst of all, Miley could feel her pussy growing wetter by the second, utterly against her will. The situation was exasperated by the thickly padded diaper under her loins, crinkling loudly with each unconscious thrust of her pelvis against Ms. Smythe’s thigh beneath her. In spite of her blushing humiliation, she was soon involuntarily grinding her pelvis at regular intervals.

     “You naughty girl,” Alice smirked. “I demand that you cease this disgusting behavior this instant, young lady,” she said, rather unconvincingly, as she landed a light but firm swat with her open palm to Miley’s rump. The young pop star squealed and wiggled in a vain effort to avoid the blows, which just resulted in her inadvertently rubbing her neatly trimmed privates on the padding below her (which she noted was getting wetter by the minute beneath her soppy wet loins.

Though it went on for less than five agonizing minutes, it seemed to Miley that her humiliating rectal temp check was actually taking forever… at last, Ms. Smyth began the process of tugging the thermometer slowly from Miley’s asshole. “Hold still, honey-bunny,” she said sweetly, popping the thermometer from Miley’s butt-hole with one final short, sharp tug.

Miley hung limply from Alice’s lap, breathing heavily as the head matron studied the thermometer. “Oops! Silly me! I forgot to shake it down first! Looks like we’ll have to start all over again,” she said with a sinister smile, holding the thermometer next to the air conditioner to make it nice and cool again.  Miley’s eyes nearly bulged out of her head when she heard she was going to have to go through all that again, and she bucked and struggled to get away… but it was a simple matter to pin the young star in place again, and Ms. Smythe clucked soothingly, a sadistic grin on her face and she spitefully pushed the thick glass tube into place once more.

Miley emitted a liquid grunt as the thermometer was pushed unto place again, then simply hung, limp and defeated with the icy glass protruding from between her butt-cheeks, passively accepting her fate.… but Ms. Smythe had other ideas. She took the thermometer between her thumb and forefinger and twisted it slowly back and forth in Miley’s butt, making the girl grit her teeth and thrust her pelvis reflexively. Alice smiled and patted the pop princess’ quivering rump, toying with the intrusive glass object planted firmly in her backside, and soon she had Miley openly humping the diaper spread open under her loins.

At last, sensing an orgasm was approaching, the head matron spitefully pulled the thermometer from Miley’s ass, leaving her dangling, sweating and exhausted over Alice’s lap. “Hmmm… your temperature is a tad high,” she said sagely, patting the girl’s soft buns gently. “Not to worry, though,” she said, unwrapping the suppository she’d taken the liberty of fetching while she’d gathered the thermometer and the lube. “I know exactly what to do,” Ms. Smythe said sweetly, pushing the suppository through Miley’s anus and deeply into her rectum.

And as the diaper was pulled tight over her sopping wet pussy and sealed shut, snapping the onsie closed overtop of it, Miley began to feel a strange tingling sensation building in her colon…

     “Now that we have that out of the way,” said Ms. Smythe, helping Miley unsteadily to her feet, “I think it’s time for...”

An afternoon in the playroom

A nap in the crib

A stroll around the grounds

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