Unexpected Changes

Ryan sharply tugs upwards and rips the two tapes of Heather's sodden diaper. She flinches and squirms under his hands but doesn't stop him as he repeats the process for the lower two tapes but once those tapes were loose she suddenly stretches her hand out and presses over the unrestrained face of her diaper, hiding herself from him as she breaths rapidly. Her right hand protected her groin from being uncovered and her left held her pacifier hooked over one finger and pressed against her chin in nervousness.

"W-wait... are you... s-sure about this... I'm... it's..."

Ryan lays his right hand over hers and smiles at her. A genuine smile. His misgivings about her were being washed away by the second upon seeing this masked side of her. He'd never have guessed at this being what she does in private. "Don't worry, little Heather. I'll manage. Just walk me through it, okay?" Ryan was intentionally putting on a more gentle voice. He was already a bit baritone and had a bit of that "dad voice" going on, which he made great use of in mock trials during law school to garner sympathy or could use it to command attention and generate presence in a noisier court but here it seemed to have a very different effect on Heather as she blushed, squirmed, and looked away as her hand slid out from beneath his and joined her left at her chin.

"Oooo-kay. G-go ahead... Mister Leyland..."

Ryan raises an eyebrow at her as she timidly gives him permission. "Mister Leyland? Not Ryan?" He teases as he carefully grips the front flap of her heavy diaper and begins to pull it open. She can only shake her head in a short arc as her diaper pulls open and the acrid scent of urine wafts up and gets caught in the nostrils.

The kneeling man takes a sharp breath seemingly of surprise and pauses as Heather's hands shoot down from her chin to grab his wrists as he holds the flap upright and open. Her legs were folded up tight and her knees had been spread wide, almost touching the changing mat beneath her as she left her groin totally exposed to Ryan. But as he pauses from his first whiff of her urine, she starts to raise and shut her legs again. "N-no! I'm sorry! I shouldn't have- it's dirty, I'm so sorry! This was a mistake-!"

"Heather." Ryan's voice drops into that fatherly tone he used to put emphasis on serious topics and Heather freezes, shutting up immediately as she stares at him breathless and lets her legs slowly spread back open with each word he spoke. "We can talk about mistakes once we're done with your diaper change. Just help me through it, it's my first time."

Earnest appreciation floods over Heather's face as her hands hold on for a moment longer and finally release his wrists to slide back to her chest, resting on top of her bra-supported bust. She watched quietly as Ryan fully opens her diaper and lays the pee-soaked pad out on the mat. She lets out a quiet gasp as cool air breezes over her wet crotch and her legs finally spread completely open, her knees sideways on the floor as the soles of her feet almost touch one another, separated only by the width of her open diaper laying between her feet. "Y-yes, da-... yes, Ryan. S-start with the... wipes... you'll... need to, uhm... clean me up a bit."

Ryan gives her a patient smile as he takes the packet of wet wipes in hand and peels it open. He takes one and cautiously brings it down between her legs which finally forces him to look down at inspect her groin. Minutes ago this woman had been berating him loud enough for the entire floor to hear. Now she was showing off her pussy and asking for a diaper change. Ryan takes the wet wipe and presses it to Heather's completely smooth pussy lips. Her labia were utterly hairless and, as he swipes and rubs the cleaning wipe over her skin it starts to come up yellow as it cleans off urine residue. She was still sitting up and taking shuddering breaths as he cleaned her crotch up. Some slight belly rolls showed on her lower abdomen as she hunched over a bit to watch with shallow breaths as her subordinate wiped her clean. He pauses to refresh wipes and gives her a quick look as she returns it. "This... might be easier if you were laying down, you know. Don't I need to clean all of your... down there?"

Heather bit her lip again and meekly nodded. She looked like she wanted to protest but couldn't find the words and acquiescence was easier to achieve than finding a way to refuse him. Before he took out a new wipe, Ryan shifts forward and reaches for Heather's neck which makes her sharply inhale before he gives her a look.

"Relax, I'm just helping."

The woman blushes as she starts to trust him and lean backwards. He supports her weight as she tilts back and rests in his arms as he lays her flat on the mat. Ryan slips his arm out from behind her head and kneels back down between her feet and picks out a fresh wet wipe to resume cleaning her up. "J-just... clean a-anywhere... my pee... my urine might have s-soaked into... it'll s-stain the fresh pad o-otherwise." Heather stammers out some instructions and lets Ryan work. She shivered and exhaled softly each time the cold wet wipe brushed over her clitoral hood or sideways across her labial folds and her hands shifted now to her cheeks. She inserts her own pacifier and her elbows contain her chest as her hands clench into fists and press into her cheekbones as she lets Ryan wipe her clean.

Finding himself pleasantly surprised by her willingness and marveling at her physique at her age, Ryan gets a bit distracted as his eyes trace up her fairly flat stomach, ample chest now squished by her own arms, and to her blushing face which was intentionally avoiding his eyes as she lay flat on the changing mat. His hand was starting to roam on its own, moving out to her inner thighs at the joints or up her groin to just beneath her belly button.

Anywhere the pee might have soaked into... I guess... lower too...

Ryan gets a fresh wipe again and places one hand on Heather's left thigh to keep her legs spread as his hand presses the wipe to her pussy and dives down, rubbing along her skin until he bumps into something... hard? His fingertips nudge and explore the item and he watches Heather jolt and start to sit up but only gets as far as her head coming off the mat and staring at him with wide eyes. She doesn't even spit out her pacifier as Ryan slips his hand under her leg and lifts. He hefts up her hip and peeks underneath her buttocks to see what he'd run into but when he sees nothing beneath her he looks at her. And, just beneath her pussy, he spots a flesh-colored circle. He glances up at Heather as she curls her toes again once he touches the item and runs his wet wipe around the base and hooks under it. He pries it up as she squirms and whines into her pacifier and he manages to pull the neck of a buttplug out from her anus, revealing the flesh-colored item he'd initially run into was a butt plug base and her anus was clenching onto whatever was left inside her as he looked at the neck of the toy.

His mouth feels dry as Ryan looks at the woman and he wonders a single thought.

Just how kinky is this woman?

Letting the toy slip from his grip, Heather's anus sucks the item back inside and Ryan presses on the disguising flesh-colored base to snug it inside. Heather moans into her pacifier as he gyrates his fingertips on it for a moment and gives it a light tap. "Naughty girl... I guess you knew what I meant when I said friends used sex toys. At work too...?"

Heather has no response as Ryan resumes wiping her clean until, finally, he puts the third wipe into the growing pile of yellow-stained wipes and lifts her hips with his right hand and takes the diaper with his left. He slides it out from beneath her and sets her down with a shared sigh of relief.

She finally removes the pacifier for a moment to give him an instruction. "R-roll it... from the front... and-and then you can tape it shut... with the t-tapes... holds in the... in the..."

"Holds in the smell?" Ryan says with an interrupting comment. "Got it. Like this?" He says as he sets it on the floor beside her, within her view, and rolls it slowly and carefully. He thinks ahead to not squeeze the pad and wring out her urine and successfully rolls it shut and tapes it up, as directed, leaving him with a cooling pouch of his boss's urine and shame. "Good... roll over, please. I'd like to get your backside before the fresh one goes on."

Heather wastes no time in obeying his order and shifts her weight, with some help, and rolls onto her stomach. Ryan pauses for a moment as her backside, by no means unappealing, looked a fair bit smaller than her skirt usually suggested. That skirt which suggest such a plush ass... no way. Starting to wipe her butt cheeks clean, Ryan starts to quietly question and tease her. "Are you... always wearing a diaper in the office, little Heather? Is that why your ass always looks so..." he raises his hand and playfully spanks it back down, making her soft ass cheek jiggle. "Plush?"

She whines from the spank but more so from the correct guess on his part and looks over her shoulder to nod and confirm it. She had returned her pacifier to her mouth and refused to say anything as he wipes her completely clean and finally moves to roll her back over again, which she helpfully shifts her weight for. Once on her backside again and her utterly-smooth crotch exposed to him thanks to her spread legs, she shifts herself sideways to center herself on the changing mat and timidly starts to raise her knees to hide herself just to have her legs spread back open by Ryan's hands.

"Ah-ah, little girl... I don't think I'm done down here just yet... so keep those legs open and we'll get you wrapped back up, okay?"

The dark-haired woman's nod, timid as it was, makes Ryan's confidence only grow. Seems I'm not half bad at this. With her going along with it... I wonder just how far she'll take it.

Grabbing the fresh diaper, Ryan unfolds it and twists and turns it in his hands to try and figure out which end was the back and which side was the inside. Heather watches him fumble for a moment before almost reaching for her pacifier when Ryan gets it and looks down at her. "Hips up, let me get this underneath you." He says, reverse-engineering her diaper change; he'd wiped her down first and then removed her wet diaper, he figured he would put her dry one underneath her and use the baby powder she'd helpfully kept available on the changing table. Heather does as she is told immediately and bridges her hips up by flexing her gluteal muscles and pushing up on her knees. Her hips rise and Ryan slides the diaper underneath her buttocks and he watches and listens as the diaper rustles and depresses under her weight. The thick padding was almost a half-inch thick which, for what she wore in public, was a daring amount of thickness.

She starts to reach for the bottle of baby powder, perhaps to try and hurry this along as she was evidently at her maximum amount of humiliated blush and was starting to sweat from the nerves but Ryan snatches it before she can reach it and inspects the bottle deliberately slowly to leave more time with the woman's lower body totally nude for him to admire while he feigned looking at the powder bottle's label.

Going on forty-five and she looks tighter and cleaner than the college sluts sleeping around at parties...

He upturns the bottle and begins to sprinkle a heavy amount of the floral-scented powder over her groin and Heather flinches and shivers from the ticklish sensation. Her eyes pop wide open as Ryan's hand presses down against her thigh joint and starts rubbing the rash-reducing powder into her delicate skin. Her skin gets more delicate as he rubs left from her leg and over her pussy, lingering over her labia and starting to press his fingers into her lips and coating her entire crotch with an even layer of her baby powder. "How do you get your pussy so soft, little Heather? It's the softest thing I've ever felt... so smooth and tender..."

Ryan was intentionally laying on the vulgar talk of his boss's genitals and Heather was showing her humiliated discomfort. She squirms beneath his rubbing hand and curls her toes more as his fingertips graze over her clitoris and sucks in a saliva-heavy breath around her pacifier before pulling it free and whining quietly. "Hhnnn! It... I u-use a... d-d-depilatory cream... e-every... mmf, often, it's... often... it f-feels better... if I'm smooth."

He smirks at her as he feels satisfied with how much powder was covering her groin and softening her joints. More than likely he'd used way more than was needed, but making her squirm was always worth the effort. "I'll say. You feel like heaven down here." He teases as he sets the powder bottle aside and brings both hands together over her groin. His thumbs press into her tender labial folds and start to rub up and down. Each swipe makes her shiver harder and he even begins to spread and fan out her pussy without so much as a peep of protest. Heather replaces her pacifier and rocks her head back, panting heavily through her nose as dribbles of aroused pussy juice leaks out of her cunt and soaks into the heavy coating of baby powder covering her genitals.

"Someone's getting a bit messy again. I didn't think you'd be the type to let me do this... you must be even naughtier than I thought, Heather." Ryan teases as he continues to masturbate her with his thumbs. She doesn't respond, not verbally, but as he calls her naughty he feels a fresh shiver run through her body and her vagina clenches, her pussy lips visibly throbbing and squeezing out even more of her own arousal. Ryan chastises her with a few clicks of his tongue. "Tsk-tsk-tsk, little Heather... getting horny are we? You wouldn't want to soak your last diaper before you even get it on, would you? That sounds almost like the kind of..." Ryan pauses as he realizes he was getting caught up in the moment but Heather's head pops up from the changing mat to stare up at him with needy eyes. She's enjoying this even more than you, I think. Okay, Heather... let's see how much I can keep up. He clears his throat to cover his pause and continues. "Eh-hem, sounds almost like the kind of thing I ought to spank you for. Being so wasteful of my efforts to change you..."

Heather's head tipping back and her rolling her hips up to meet his fingers tells him he was right on the money. She pants even heavier as he sizes her up and just how to deliver this spanking she so clearly craved.

I can't very well ask her... that'd ruin the whole mood. I could make her get over my lap... but then she'd get off her diaper and... no, it'd take too much effort. It has to be fast, and right now. What if-

Ryan shifts himself forward to get more in between her spread legs and grabs her right knee. Still kneeling on the changing mat, he lifts and tips her leg over to meet her left and grabs both of her legs and picks them up as Heather whines and moans into her pacifier. Her noises were getting more desperate by the second but it isn't until Ryan places her feet onto his right shoulder and pins them there with his left hand does she mewl into her pacifier and curl her toes, rubbing one foot against his ear presumably accidentally or just by necessity as his right hand drops low and rubs against her vertically-raised ass. With her ass exposed by way of lifting her legs up and out of the way, all Ryan had to do now was swing his right arm back and send it forward to spank her directly, his fingers pointing at the floor and her ass fitting perfectly into his palm as he measured the angle and gripped her firmly once he was satisfied.

"Good girl... but not so good if you're just gonna wet every diaper I put on you. So... let's spank you quick and get you padded... I think we might be getting suspicious if we spend too long in the bathroom... don't you?"

Heather whines into her pacifier but still nods. Her eyes were starting to get glassy from how deep into her headspace she was getting and as Ryan releases her ass and swings his arm back to prepare to spank her she sucks in a sharp breath and looks at him directly.

Do I see... adoration?

S m a c k

Ryan's arm launches forward and smacks his palm cleanly over Heather's ample buttock and makes her yelp into her pacifier. Her legs twitch and jerk against his chest and her right hand leaves her cheekbone to grab his shirt by his hip, just grabbing something as he lines up a second spank when they are once again interrupted by the whoosh of the bathroom door opening and a pair of voices chatting casually as they enter and go to use the facilities.

Ryan and Heather sit frozen in place with pounding hearts as their coworkers use the bathroom as intended. Ryan is forced to examine his situation again and cannot believe he has his 44-year-old boss all but naked, laying on her back with her nude legs held up and on his chest, her backside resting on a diaper and her ass cheek firmly in his hand after he spanked it.

Nobody in the office would believe me... and yet I think I'd get more high-fives and congratulations than a sports team winning a championship game.

After a tense wait the two newcomers depart and return to work and the pair let out held breaths before Ryan surprises Heather with another smack. She squeaks into her pacifier as he starts to lower her legs again. "We'd better finish this up... otherwise we'll be here all day with people coming and going... okay? Just sit tight... spread out again, please."

Heather doesn't even nod, doesn't even blink as she stares at Ryan and spreads her legs open for him again. He notices that her cunt was drenched now, with her coating of powder turning to all but mud on her pussy as her vagina drooled in lustful and aroused need.

This time, and only for fear of eventually being overheard and found out, Ryan takes the front flap of the diaper and folds it up and over her hips. Ignoring her weak whine of dismay, he lays it flat on her groin and pulls the side flaps up and around her hips as she clutches her hands over her chest, tilting her head up to watch her own diapering as Ryan figures out the rustling item and seals her drooling pussy behind the thick padding. Once the diaper was taped, and her whining hadn't yet quieted down, Heather lifts and pushes her hips into his hand, trying to signal that some part of her didn't want the padding on just yet. But as Ryan clearly shows he wasn't taking his hand away or letting her peel the padding back off, she slips the pacifier from her mouth just enough to helpfully offer some advice with a stuttering and breathy tone.

"S-start... high... with th-the top two... then the b-bottom two... and re-tape the... the top two... to make it nice and... mnf, nice and snug."

Ryan, still on his first time diapering an adult woman, follows her direction and tapes the top two tapes to seat the diaper, tapes up the bottom two to start securing the tighter fit, and re-tapes the top two to perfectly bind it around her waist and, with a poke of her covered crotch, confirms it was on, secure, and that she was padded.

"There you go... diaper on. We... should probably get out of here. Come on." Ryan felt reluctant to do just that as he slowly stands up and notices a sizeable tent on his slacks. Grunting as he awkwardly tries to force his erection into a more comfortable position, he looks down to see Heather aggressively looking to the side but still caught her eyes flicking over to it as she nibbled on her pacifier. Shaking his head and sighing he reaches a hand down to help her up. "Look, it's a natural reaction... you're very pretty and I just got my hand all over your... ahem, alright? I can admit that..."

Heather weakly giggles into her pacifier shield as she sits up with Ryan's help and lets him help haul her to her feet, standing a bit unsteadily on quivering legs. She carefully pulls her pacifier from her mouth and tips her head towards her clothes on the changing table. She speaks quietly, as if afraid someone might overhear her, "Y-you know... I'm not... seeing anyone else at the office today... an-and..." she takes a step forward, leaning into Ryan a bit to mumble even quieter, "we could... finish up... in my office? I think... you... may have wanted to... finish that spanking?"

The 24-year-old intern stares at his boss as she timidly tucks her shoulder-length hair behind one ear and blushes red as a strawberry, standing with her right arm under her bust and her left playing with a lock of hair as she crinkles with each twist and twitch of her leg thanks to the diaper he put her in.

Last chance to not do this and have a somewhat normal working relationship, Ryan...

"I'd like that. Let's get you dressed... unless you wanted to be paraded through the office like that."

Heather stiffens up and sucks in a sharp breath as she was clearly considering it but shakes her head violently as Ryan holds up both hands to making a "calm down" gesture. "Relax, I wouldn't actually... but it'd be adorable. Come, I'll help."

Offering his hand to her, Ryan leads Heather off the changing mat and onto the bathroom tile. She rustles with each step and he vaguely wonders how he never heard her before. He starts with her cream colored shirt and helps slide it over her head and tugs it down, smoothing it over her stomach as she lets him take the lead on dressing her. He smirks as he notices a distinct lack of panties among her folded clothes and grabs her semi-sheer stockings and sits on the toilet seat and gestures her over. Heather obliges and steps over, lifting one leg and letting him slip the stocking up her smooth skin and tugging it taut against her mid-thigh before repeating the process on her other leg. He lets her foot down and grabs her skirt. Ryan unzips the skirt and crouches down in front of Heather, holding the black garment out in a loop for her to step into. His diapered boss politely steps into the ring of fabric and he stands slowly, drawing it up her legs and around her hips before reaching around her to zip up the skirt behind her, each of them breathing a bit heavier by the moment but Ryan could tell that each garment added to Heather's body was having a diminishing effect on her "little" state. Her glassy eyes were fading and the timid fidgeting of her fingers slowly stopped as her arms dropped to her sides and then eventually her blush started to fade.

As Ryan held her jacket up for her she put herself into it, slipping one arm and then the other in easily and turning around as he grabbed her shoes and knelt down. She caught his shoulder and held out her other hand and her voice, which had been barely able to assemble a sentence before, was much closer to what he was used to but Ryan could hear a slight amount of gentleness in it now. "That'll do, mister Leyland. I... thank you, for your help. I'll get my own shoes, thanks. If you could pack up the-"

"Yeah. I got it." Ryan says back bluntly, stepping away as Heather seemed to have reverted to her boss-like nature. But he held a smile as he crouched down to start folding up the changing mat and she got her heels back on.

Once folded, she took the mat and tucked it into what was evidently her diaper bag, put the bottle of powder and the packet of wipes into their respective organizer sleeves inside the bag, and grabbed an opaque trash bag from the front zipper pocket of her rectangular bag. She tucks both her original diaper and the one she'd wet upon being startled by Ryan into the trash bag and ties it tightly before setting it on the changing table, shouldering her bag, and turning to Ryan with a friendlier smile than he'd ever seen.

"Okay... uhm... today was... it was nice, thank you."

Ryan can't help but notice just how different she was now that she was back in her usual outfit, her "in charge" demeanor was coming back by the second and he could tell he wasn't getting into her office again today. At least, not for that spanking she suggested while her diaper and bra were exposed.

Take what you got, Ryan. She could be dialing HR right now and she's not.

"You're... welcome, little Heather." Ryan pauses as he notices her flinch at his jab. "I-, I'm sorry, I-"

"No. It's... alright." She steps forward, heels clicking on the tile and she unlatches the lock before looking back at him. "Just wait a few minutes before leaving... can't go out together."

He nervously chuckles and rubs the back of his neck as she pushes the door open. "Right... I'll... sit here a minute. Gotta let myself calm down anyway."

Heather pauses as she glances back and sees Ryan's half-mast tent still pitched in his slacks. "Hn. I see that." Her eyes trace up to his and she smiles. "Until next time, mister Leyland."

Ryan plops back down on the toilet and starts breathing as calmly as he could as he listens to Heather's heels departing the bathroom. Shuddering breaths eased down into gentle breathing as adrenaline and arousal fade away. He looks down at the floor where Heather had been laying, legs spread, smooth pussy exposed to him and drooling with need. And he remembered the exact expression she had when he taped her diaper on and the relieved yet frustrated look she had.

She's not the only frustrated one now... dammit... I should have pushed to finish things in here...

Ryan sat at his desk and scrolled through emails that same afternoon. The clock was showing an irritating 4:56 PM and he was almost out of here when he heard a familiar stride getting closer. He swivels in his chair just in time for Heather to appear in his cubicle with a Manila folder and slaps it against his chest.

"Here." She says bluntly, not quite meeting his eyes as she steps back and blocks the cubicle entrance.

Ryan's eyes quickly run over Heather and he really notices just how he couldn't detect her diaper underneath that skirt. He wondered if that's why she always wore skirts. Now, she looked and acted nothing like she had when he found her shivering and blushing from soaking her diaper accidentally. Even less than when she was stuttering with his hands on her groin. Shaking himself out of his thoughts and willing himself to not get aroused, he looks down at the folder his hands were pressing to his chest and flips it open. At the top of the first page was a single bold-font line "Offer of employment". Before he even gets to line two he looks up at Heather who was still avoiding his eyes.

"I... wanted to take you on as my... protege, of sorts. You're studying for the BAR... I wanted to see if you might join my attorney team." Heather seemed to be avoiding something but Ryan was a bit too stunned to make a proper reply. "Just... read through it and think about it. Let me know by tomorrow. Or, later this week, I guess... any time, really..." She waits for a second to see if he had a reply now and turns, waving over her shoulder; she never waved. "Good night, mister Leyland."

Ryan watched her vanish from the cubicle and looks back down at the paperwork. Paid intern to Heather's student attorney... how... interesting. Wait... what's... Ryan flips through the pages as he thinks but notices the tab of a sticky note peeking out between the pages and slips it out. In a flowing, neat hand script and utterly diverged from the legalese of the employment offer was a simple note, evidently from Heather. Upon reading it, he knew he was taking the job...

[Part of your new job will be changes and discipline. I hope that's alright with you, Daddy]