Tiffany's Timidities Ch. 04

"Perfect," he enthused.

"Ow," she lied, but the undertone of her pleasure was clear.

"Close your eyes and relax," he said. "Enjoy it."

"No. Lemme go." He drew his finger partway out and then pushed in again.

The ointment's reactivity bloomed. She gave a long whine as her panties began to saturate in response.

"You like being naughty, don't you?"

"Noh."

"Don't worry. You're still a good girl."

She hugged him tighter, unable to respond.

He pumped his digit carefully in and out. Her mouth fell open above his shoulder. There was no way this was supposed to feel so good.

"Isn't that's nice?" he goaded. "Ready for two fingers?"

"No!"

"Or better yet, imagine my cock. How would that feel?"

"God!" she gasped, pinching again.

"I think you'd love it."

Her nipples went stiff. This was too intense by far.

"Want to try?" he offered, ever-hopeful.

"No, my God, please stop."

Despite her efforts this answer came out girlish and horny. She was exhaling in soft little whines. The thought of what anal sex might do to her in this condition was worrisome. Her anus was so excited it was practically massaging his finger. Whatever ingredients were in that ointment made movement feel incredible.

Grisholm had been fantasizing about her all night. There was no question in his mind that she embodied every one of his fantasies. Her contractions around his finger only made him hunger more. His erection bloomed, straining his pants. He widened his stance and groaned as his self-control wavered.

She tightened her hug. Warm ointment wetted his finger.

"Once before I die," he whispered. "That's all I ask."

"No! I've never even tried before!"

"I'll make sure you enjoy it."

She gave no audible answer to this, only puckered tighter.

"God," he breathed. "You're incredible."

"Please lemme go. I'm so late."

He eased his finger out and allowed her legs to drop, snuffing his urge. He knew patience was his only chance.

As soon as her feet touched the floor she stepped back and grabbed her bottom. Her eyes darted nervously about.

"Listen," he instructed her. "Run along and see Mitchell. But keep in mind what I said. You're practically made for this, okay?"

She looked up.

"That's right," he affirmed. "There's a whole world inside you just waiting to be discovered."

She clambered into her wedges and scurried toward the door.

He was still staring at her butt when she pranced over the threshold.

An anxious grin hijacked her face en-route to the next office. Her bottom was alive with pleasure.

SCENE TWENTY-ONE

Doctor Ian Mitchell's door was halfway open. He was seated in his high-backed leather desk chair, swiveled toward the window.

"Good morning sir!" she sang, not realizing he was on the phone.

He spun and checked his watch. Then he gestured for her to shut the door and approach.

She did so immediately; anticipating his biding by standing right in front of him with her hands gathered behind her.

He made no effort to greet her; just let his eyes wander.

She tried to tug her shorts down but they barely moved. A petite camel-toe remained in front and the rear cuffs were halfway up her ass.

Ian wore a pressed dress shirt, dark slacks and polished shoes.

"No," he continued curtly into the phone, "I'm not going to resubmit it with your new diagnosis codes. The ones I used were valid. It's time you guys quit stalling and reimburse my practice or so help me God I'll complain to every regulator you've ever heard of and a couple more besides. I'm sick of this run-around!"

Tiffany shifted in her sandals, feeling wildly horny. She noticed her nipples tenting the ribbed cotton of her top.

"I don't care what your system says," Ian continued, eyeing her up and down. "No. I've already talked to your TPA. They sent me to you. No, you will not transfer me back there. You're the carrier! You have to authorize payment, it's that simple. This is for work I performed four months ago, understand? Yeah...? No, you listen, I didn't spend a third of my life memorizing every possible human ailment just to be told that I need to learn your ever-changing codes as well! I've got two more you need clear after this one, too. Uh-huh. I know... you decline everything; decline, decline, decline. I'm sure that's all your bosses want, but it's a scam. You are obstructing valid medical insurance claims, and that's illegal. That's called fraud, okay? Yes, I know we're on a recorded line. Yes. Yes, I would very much prefer to speak with your supervisor."

He made a twirling gesture with one finger.

She opened her mouth to say something but didn't. A brief hesitation later, she turned around. When she glanced over her shoulder his eyes were already on her ass.

'Jesus,' she thought, rolling one ankle outward and clinging to a lungful of air, praying he wouldn't discover how wet she was.

The expectation of his touch toyed with her, becoming a certainty. She stared at the ceiling, wishing her clothes were less provocative.

No matter how conflicted she felt about this job, these moments of anticipation were undeniably affecting. Just standing there listening to his voice, each incremental rise in his frustration made her muscles tighten. She shifted her weight and crossed her legs, trying to distract herself by studying the art on the walls. It was to no avail however. Her pulse remained firm. She could feel it in every erogenous zone. She tried to tug the shorts down again but their central seam and lowermost button seemed stuck in the worst place; right against her clit.

For Mitchell, watching her fidget was therapeutic. Absent her presence he would have been yelling and banging the receiver on his desk.

Conversely, her mental state began to deteriorate. She started doubting her attractiveness, imagining her butt looked too big and perhaps showed some dimpling too. Restraining the urge to hunt for these phantom flaws, she crossed her arms and switched her weight back to the other foot, tucking one leg tightly behind the other.

She soon found herself actually wanting his touch; as an affirmation of her attractiveness if nothing else. This rattled her even more. It was a paradigm she was unready for.

When Mitchell finally secured some vague promise from the insurance company, he hung up.

She spun around, radiating discomfiture.

"You're late," he announced. "Why didn't you call?"

"I tried sir but the main number went to voicemail and that's the only one in my phone," she blurted in a rush.

"Really."

"Yes I... I got a flat tire on my bike. Otherwise I'd have been here on time."

"Don't you think you ought to have everyone's cell number and office extension in your phone by now?"

"Yes. I'll fix that today, sir. I'm sorry."

"You're half an hour late. And don't tell me you walked here dressed like that."

"No. I changed in the washroom and, um, I got a ride."

"A ride? From whom?"

"Just this guy who stopped."

"Really?"

"Yeah—I mean yes, sir. He was really nice."

"I'm sure he was. Where's your bike?"

"Outside."

"And it's got a flat?"

"No. He fixed it."

Ian raised his eyebrows and leaned back, lacing all ten fingers behind his head. "So... let me get this straight: You got a flat tire, some random dude pulled over, fixed it and gave you a lift to work?"

"Yes sir. See—"

"All within half an hour? Baloney. You overslept, didn't you? You just made all this up."

"What? No, I didn't. Honest, sir, you could ask him. He works at a repair shop on Railroad Street."

"It's Railroad Avenue, and there're four or five shops like that over there."

"I'm not lying! He... he said his name is Cartwright and the shop is like, Mick's or Mack's or something."

Ian harrumphed.

She twisted her wrist in one hand, regretting divulging so much about Cartwright. It seemed like a dumb move.

His silence only compounded her stress. She adopted a sulk, rubbing her bare knees together and toying with one of the belt loops on her shorts.

"You don't believe me," she pouted. "But it's really what happened."

"I want to believe you," he answered, "...because I like you."

She alternated her gaze between his left and right shoe, still pouting.

"I just hope you thanked him properly."

"I did!"

"Honestly the thing I don't believe is that ridiculous outfit you're wearing. Did Grisholm really buy you that?"

"Yes sir."

"It makes you look like a spoiled brat."

"I know and it's really uncomfortable. But he said I had to wear it 'cause there're no patients today."

"Turn around," he ordered, sitting up.

She nearly tangled her feet. Butterflies swirled in her stomach.

His touch arrived all at once, just as she'd imagined.

"What size are these things?" he wondered incredulously.

"Um.... Extra-Extra-Small, sir."

"And you normally wear...?"

"Small... sir."

He adjusted her position manually to behold a three-quarter view of her butt, prying more of her soft flesh out from under the cuffs until her cheeks fairly bulged.

"Yes," he commented salaciously. "These are very tight. You must be quite uncomfortable."

"I tried to tell him, sir, but—"

"But it's not your choice anymore, is it?"

She sucked in a breath and said: "No, sir... I know, but please let me—"

"They do show off your assets."

"They're way too—"

"By which I mean your ass, Tiffany."

"Nn-mm."

"That's what Grisholm likes, you know; this round little rump of yours."

She looked back just as he delivered a cross-wise swat, animating both cheeks.

"Ah!" she jumped.

"Deplorable. Not at all in good taste."

"No sir. I, um...I can change into something else if you'd prefer."

"Really?" he enthused, making eye contact with her for the first time in a minute. "You brought alternative outfits? How prescient!"

"Well, just some leggings and a sweatshirt."

He stilled, nonplussed. "Is that supposed to be funny? Is this a game to you?"

She bit her cheek and looked away.

"Grisholm has been waiting since Monday to see you in this," he continued. "I'm not going to deprive him of that for a lousy sweatshirt!"

"No Doctor Mitchell, I didn't mean—"

"Are you sure you're in the correct frame of mind for this job today?"

"Yes sir," she answered, glancing at the ceiling.

"It doesn't seem like it. I would suggest a bit more deference. Otherwise you may attract the wrong sort of attention."

"No sir, I didn't mean—"

"Don't tell me what you didn't mean. I heard your tone clearly."

"Ung'kay. Sorry."

"And less smirking would help too, unless you want me to extend your probationary status indefinitely."

She bit her lip this time. She didn't dare look back.

"Now," he continued. "Tell me again the name of this fellow?

She delayed a few seconds, praying she wouldn't giggle. "Um... Cartwright, sir."

"And how exactly did you thank him?"

"Well I... I, um, just said thanks."

"Orally?"

"What?"

"With words; by mouth. Nothing else?"

"No sir, nothing else."

"He didn't ask you to return the favor?"

"No."

"Did you get his address so you could mail him a thank-you card? Or a gift?"

"Wh—? No."

"Why not?"

"That would be w—"

"Is he unattractive? Is that why you're so reticent?"

"No, he's..."

"Then what kind of person are you? An act of chivalry saves you from danger and inconvenience and gets nothing but a simple 'thank you'? That's it?"

"Yeah, that's like, normal sir."

"I emphatically disagree."

"Well..."

"Shall I try to locate this gentleman to thank him for you?"

"No! My God that would be so—"

"How will you clear your conscience?"

"I don't—"

"Goodwill ought to be reciprocated."

"He's fine."

"He's fine? You still aren't listening, are you? Maybe we should both go see him; so I can watch you thank him in person."

She blanched this time, imagining how embarrassing that would be. It muted any lingering risk of laughter.

"How else will I be sure you've done it?" he continued.

"Please don't; I'll thank him when he calls."

"He shouldn't have to call. You should call him. It's about respect. And besides, going down there might be a marketing opportunity. I'll look into it."

"No, you're insane!" she announced without thinking.

"Excuse me?"

"Uh..."

"That caps it," he growled, grabbing her by the wrist. "I'll not sit here and be mocked by a twenty-two year old."

"Kidding!"

Before she could react he flopped her face-down across his lap, muttering: "Over my knee."

"Wait!" she squealed.

"We're going to get to the bottom of this once and for all. Not listening... disrespectful... excuses. I don't care for any of it."

"I didn't mean it!"

He hooked his left hand around her waist and, despite her squirming, managed to get her ass centered atop his lap.

"What you need is a brisk warm-up."

"Please no!" she protested, scrabbling for traction with her feet and fingers. Blood rushed to her head and her hair hung forward.

"Keep still," he insisted, securing her with his left forearm and straightening one knee so his other became the sole high point supporting her pelvis. This crushed the shorts' buttons against her mons pubis, which she felt acutely, and canted her ass upwards before him.

"Fuck, come on sir!" she complained.

"Don't add profanity to your list of sins."

"Let me go!"

"Absolutely not. You may be accustomed to a world in which pretty girls get away with murder, but not anymore. You're about to experience some accountability."

"I didn't do anything wrong!"

"See? You never take responsibility."

"Yes I do!"

"Oh? Then tell me: How many ways did your tardiness negatively affect my clinic this morning? Hmm?"

Her mind raced: "I, uhm... Three?"

"Wrong."

"But it wasn't my fault!"

"Again with the denials. Clearly you're overdue for this."

"No!"

"Raise your bottom higher, up to my palm. There is a right way to do these things and we are going to adhere to it, understand?"

Her brows furrowed and she arched slightly.

Displeased, he gripped her shorts' rear cuffs and yanked them skyward, dramatically steepening the pitch of her lower back.

"Eek!" she complained, straight-arming the carpet and pointing her feet.

"Like that," he affirmed, releasing her shorts.

A whimper escaped her as she struggled to balance in this new bridge-like pose. Her fingers were in the carpet and her toes were balanced on the nose of each sandal. She hardened her core to keep her butt as high as possible.

He cupped her ass gratuitously, squeezing each cheek in turn.

Keeping this position consumed a significant percentage of her athleticism. Her hands and shoulders began to burn. She lifted her head and whined: "Please hurry. This is hard."

"It's difficult, Tiffany. 'Hard' is something you'll be covering later."

She hissed through her teeth at this implication, but managed not to collapse.

He held her bare waist and continued groping as his erection inflated beneath her.

She tried to rationalize all this, conjuring various excuses and ameliorations as to why it was okay, but none of them made any sense.

"Tomorrow," he segued, "You'll need to wear something prettier."

She didn't answer. Too many other thoughts were stampeding through her head.

Fresh goosebumps ran down her legs as he stroked her gluteal crease. The way her shorts disappeared between her cheeks was one of the greatest incitements to lasciviousness he'd ever seen.

"A little dress perhaps?" he ventured. "Something wispy I can get my hands under?"

She dug her nails into the carpet and grunted: "Hm'kay."

"What was that? Speak up."

"Yes sir! I'll wear something prettier tomorrow."

"Don't disappoint."

"I won't sir."

Without further ado he raised his hand and delivered a crisp smack to her right butt cheek.

"HAh!" she cried, twisting unsteadily.

"Hold still please."

"But—"

The next spank interrupted her.

"Ohh!!"

Four more times he did this, making each side of her ass wobble in turn. Satisfying noises resounded off the walls.

It was exactly the sort of wickedness that suited her. She tried to suppress the thrill but that only made it worse. Her skin warmed and her knees dipped.

"As for today's outfit," he lectured, pausing to cup her bottom again. "We'll just have to make do as best we can, won't we?"

"Yes sir," she exhaled, slackening across his lap with a sigh of relief.

"We're not done. Rise again."

She swore under her breath and re-tensed, elevating her ass as high as possible.

"Keep the position this time. I'm going to give you six more now, quickly, and I don't want you to move."

"Sh—Nn... M'kay," she grunted.

He spanked her young bottom briskly, enlivening its firm swells.

"Oh GOhh-D!" she cried, face aghast as her feet slid backward and the swatting continued.

After the sixth spank he laid his palm across the gap where her cuffs vanished and enthused: "Very good."

"Can we be done now?" she begged, nearly breathless.

Her bottom was ringing. Half-exposed handprints had bloomed across it, peeking out below the shorts.

"Do you feel sufficiently reminded of your manners?"

"Yes sir."

"Will be you be selfless and attentive to others today?"

"Yes sir."

"Alright. Just four more then."

Before she could protest he landed another pair of smacks atop each cheek, deepening the blush of her skin. She kicked a foot back and squawked. Her earrings got tangled in her hair and she collapsed over his knee.

"Done," he said. "You may stand now."

She scrambled to her feet and swayed before him, furiously rubbing her bottom. Her face was a picture of appalled wonder.

"Remember," he said, raising a finger. "You still owe my thirty on your bare bottom for being late. This was just a warm-up to get your head screwed-on straight this morning."

"Yes sir," she breathed.

"Now turn and face my desk."

"Now?!"

He stood and abruptly hustled her to the edge of his broad wooden desk, reassuring: "I'm only going to fix your outfit, not spank you."

She found herself relieved. But then his manhood pressed itself against her tailbone, pinning her to the furniture. Her mouth formed an 'O' and her glutes tightened, either with expectance or stress, she couldn't tell which.

He opened a drawer and retrieved some stubby scissors.

At the sight of them she squealed: "No! Not shorter!"

Ignoring her, he grabbed a fistful of her hair and tucked the cool metal blades up under her shorts' right cuff.

"Please sir, come on!" she begged, arching and tensing as the snipping began. "They're already tiny!"

He cut a new vertical slit up through her shorts' right side, letting the stitching pull wide as the fabric's tension eased. Soon the slit was halfway to her beltline. Then he switched hands and repeated the same on the other side.

She pinched her legs together, silently chanting that somehow everything would be alright. But inside she was panicking. His cock was only millimeters away and her clothes were vanishing.

"Please," she begged, mussing his paperwork with her sprawled hands. "Please stop."

"Sure," he said, releasing her hair and calmly stepping back. "Isn't that more comfortable?"

She straightened and looked down at her flanks.

"Oh sir... I'm... I'm almost naked."

He traced her newly-bare skin, reinforcing her sense of exposure. The denim curled back from his touch.

"See?" he said. "I didn't make them shorter."

She spun to face him. For a moment there was total silence.

Then he hooked two fingers into her top's neckline and stretched it forward, capturing the black fabric in the scissors' bite. A wide V burst open as he cut, spilling her cleavage into view.

"NO!" she cried, grabbing herself.

She crowded her hands together, smashing her breasts into a pair of kissing domes.