Tiffany's Timidities Ch. 02

"Oh! Good," he answered, completely unflustered by her panting proximity. "Sorry. I had no idea that would be so loud."

"Jesus, I know! It scared the crap out of me!"

"Now, now; there's no call for language. Why are you wearing different clothes?"

"Oh. I was just trying these on for fun. They're on sale but I was gonna put them back."

"You seem to have lost your dress."

Tiffany looked at the bundle in her hand. "Shi—I mean shoot. I must've left it in the dressing room! Sorry! I'll go get it."

"I'll come with you. No sense in getting separated again."

"Really sorry, sir. I guess I lost track of time."

Grisholm appreciated his view as he followed her barefoot strut to the far end of the store. The elasticized denim shorts she wore were festooned with tags but hugged her nicely nonetheless. Triangular rear pockets drew attention to their brevity by pointing at one-inch cuffs encircling the very tops of her thighs. The cuffs arched upwards as they traversed her butt, exposing just enough skin to reveal the tantalizing initial swell of each cheek. He stared at her blemish-free legs, imagining her skin rising in smooth, twin domes beneath the denim. Above the shorts, her midriff was bare from her sacroiliac dimples to the pinch of her waist. The cropped tank top was snug and rose to a racer-back that flattered the muscle-tone in her shoulders.

He wiped a minor burst of perspiration from his forehead and asked: "You like those?"

"You mean the shorts?" she answered, turning her head and tugging at their waistband. "They're okay. I thought they'd be cuter on, but..."

"But what?"

"Oh nothing. I just shouldn't be shopping. They're a little too young-looking anyway."

Doctor Grisholm cleared his throat. The way her hips rocked back and forth was driving him crazy.

"Well," he ventured, "maybe you just need a different size?"

She didn't miss a beat. "Nah, these fit. I just can't be buying stuff yet. Not until my first paycheck."

They reached the entrance to the dressing rooms and stopped.

"What about the shirt? That looks good on you."

"Does it? Thanks. I only tried it on 'cause it's like five dollars or something. Everything is so much cheaper here."

"Five bucks, huh?" He studied the way the ribbed cotton hugged the padded cups of her bra.

"Yep," she sighed, adjusting the top a bit, trying to hide her navel.

"Tell you what," he volunteered. "Since it's your first day I'll buy 'em for you. How's that?"

She looked up quickly. "Oh... no doctor Grisholm. Don't be silly. I don't need another tanktop, really."

"I meant the shorts too. Just go put your dress back on. Then we'll see if they have them in a better size."

"But—"

"I insist. Go on."

"But they aren't—"

"Please hurry," he cut her off with a wave of his hand.

Tiffany was soon standing next to him at the rack of white denim shorts. Her sundress was back on with its halter top fully in place but she felt increasingly uncomfortable. He had already found a replacement tank top two sizes smaller than she'd wanted. It now lay in his cart.

She glanced around nervously, on the lookout for anyone who might recognize what was happening.

Grisholm was sliding hangars aside in rapid-fire, flicking through the denim short-shorts searching for the size he wanted.

"Aha!" he proclaimed. "Here we go: extra-EXTRA-small."

Tiffany twisted above her sandals and pressed her palms together in a vague plea as he tossed the absurdly small shorts into his cart.

"That's really not my size, sir, PLEASE!" she begged.

"It's too bad you won't be able to wear them to work," he mused, pushing the cart toward the registers. "I'd love to see them on you."

"But they won't fit me... Please don't buy them, sir! It's totally unnecessary."

"Nonsense. You'll fit into 'em; they're stretchy. Anyway they're a gift. A practically free one too."

"But they're too small!" she protested, imagining how unwearably revealing the shorts would be if they did fit.

"They'll be perfect."

He reached the check-out line and stopped. Tiffany crossed her arms and stared into the cart.

After a few seconds she whispered over his shoulder: "Can't I just quickly run and switch them for even one size bigger?"

"No, and you know what? I just thought of something."

"What?"

"Wednesdays are our paperwork days. You could wear them both then."

Her face lost color, making her freckles more obvious. "You mean... the office?" she whispered.

"Sure. They're no patients on Wednesdays. I'll check with Mitchell, but I don't see why not. That'd be cool, wouldn't it?"

She was stunned. Again she looked into his cart. A crystal-clear vision of how she would look wearing both garments flashed through her mind. She knew he was right about the stretchy shorts too; they could probably be forced on, if only barely. The result would be a four-inch white band around her hips that revealed everything.

She didn't want to make a scene in the register line, but the idea of flaunting herself in those things at the office twisted her stomach queasily. Doctor Adams would assume she was a whore. Moreover, the rest of the team might be inspired to do utterly unspeakable things. She began to swoon.

"Did you find everything today?" the lady behind the register greeted them without looking up.

"Yes," Grisholm replied with a Cheshire grin. "We sure did."

Tiffany could barely keep her eyes open. She clung to handle of the shopping cart as the stout doctor swiped his credit card.

Outside in the parking lot, he fished out her two new garments and handed them to her before arranging everything else alongside her bicycle in the back of his truck. Tiffany accepted them and climbed into the cab's bench seat without speaking.

As they began their journey to her grandmother's house, she tried to gather the courage to ask about the office rules. The undersized clothes in her lap were a cautionary signal that her protests might not be well-received but still, as they got closer she sensed her window of opportunity closing.

"Doctor Grisholm...?" she blurted out of nowhere. "Can I talk with you about something?"

He turned his head and stared silently for a moment before answering: "Sure. What's up?"

"Um..." she hesitated, suddenly feeling unscripted despite all the time she'd spent preparing these thoughts. "You know the uh, the rule... at the office?"

"Which one?"

"The one, um... about... for every minute I'm late? The spankings?"

"Oh that one. What about it?"

"Well so... I've been thinking, and... I... I mean. Don't you think it's a bit, like, inappropriate?"

"No."

Her heart sank. The accumulated indignities of the day began to rise to the surface. She was suddenly close to tears.

"You-you don't?" she stammered. Her lower lip protruded shakily. "Really? But... have you ever heard of anything like that? I mean... it's... it's just so mean!"

"Mean? What are you talking about?"

"Doctor Jacobsen spanked me really hard today!" she cried, facing him suddenly with eyes fully moist. "And then Doctor Adams came in and saw me like, practically naked! And they both... their hands—"

A sob choked off her words.

Doctor Grisholm reached across the cab and patted her thigh gently.

"There, there," he soothed, steering one-handed. "Don't be upset. They didn't mean to frighten you. And those little swats aren't meant to hurt too much. They're just reminders. You didn't get any welts, did you?"

"Nuh... No!" she managed between gasps.

"See? We all talked about this before you started. The rules are designed with your safety and training foremost in mind. All we want is for you to become the best little office girl you can be."

"But it's— And why does everyone keep calling me that? I'm the Receptionist!"

"Oh, well... that's just your corporate title. Your functional title is Office Girl. Cute, isn't it?"

"Nuhhhoh," she moaned into one palm as wet lines rappelled her cheeks.

"Suits you to a tee, I think."

"But you can't just... I mean—"

"Tomorrow we're having a staff meeting to go over the rest of your training program. I think it'll all make more sense once you know the big picture."

"There's... there's more?"

"Don't worry about it tonight. You're in good hands, okay?"

Tiffany looked down at the new clothes in her lap and blinked out a few more tears. The abject failure of her mini-insurrection left her spent. She wiped her eyes and went quiet.

"'Atta girl. Dry those pretty eyes. By the end of the week I promise you'll love working for us."

One wordless minute later he smacked the truck's thin steering wheel and exclaimed: "Shoot! I completely forgot!"

"What?" Tiffany asked, looking over at him nervously.

"I meant to make one other stop. Do you mind?"

She shook her head.

"Thanks."

Soon they were back across the river on a dusty street that was cut off from the main part of town by an earthen berm. The narrow strip of pavement was poorly patched and lined with garbage dumpsters. Grisholm stopped his truck behind a low brick building. It had no exterior signage, but there was a red light bulb above the door.

"Just wait here," he said as he shut off the motor. "I'll be five or ten minutes."

"Okay," she mumbled, unsure what else to do. Her mind felt soggy.

When Grisholm disappeared inside the store, she rubbed her nose and checked her appearance in the mirror. Her eyes looked slightly bloodshot but she was relieved to see her makeup still in place.

He eventually returned to the driver's seat carrying a crinkly black plastic bag. Once his door was closed, he fished around inside.

"Here," he announced, handing her something small. "I saw this by the register. Couldn't believe they had one with your name on it!"

He stuffed the still-full bag behind the bench seat as Tiffany examined her latest gift. It was a leather choker necklace, wrapped in black satin with a small crucifix hanging from a D-ring at the front. Centered above the sturdy leather tab that held the D-ring, 'Tiffany' was spelled out in cursive pink embroidery.

"I think it's a bracelet or an anklet or something," he elided.

"It's a choker," she corrected him.

"A what?"

"A necklace. I used to have one like this, just without my name or the metal thing. They're sorta Goth."

"That'll fit around your neck? Wow."

"Yeah. But why did you buy this if you don't even know what it is?"

"Oh, just for fun. I thought it might cheer you up. Try it on."

Tiffany carefully undid the buckle and slipped it around her neck. After one quick adjustment it fit snugly and was centered. She looked across the cab at him.

"Oh... my," he began slowly. "That is incredible. You have to wear that."

"Come on, sir. I can't."

"No. I'm serious. You must. It's really, um... nice... on you."

Tiffany flipped down the vanity mirror behind the passenger sun-visor. As soon as she saw herself, her mind flashed back to a scene she had watched earlier. The steel D-ring at the base of her throat looked similar to one she had seen used to leash a girl to a leather-clad mistress who wielded a strap-on with startling brutality.

"No..." she said softly. "I mean, thank you but... I don't think I should wear this."

"I insist. Wear it tomorrow. Otherwise I'll send you home to retrieve it and then you'll be really late."

He chuckled as if kidding but added: "And I know you don't want to go through that again."

She fixed him with a look and retorted: "I wasn't late today, sir. I was only late bringing Doctor Jacobsen his coffee!"

"All the same, that thing looks great on you. Wear it until further notice. Okay?"

Tiffany harrumphed, slouched into her seat and folded her arms. Her lower lip stuck-out fractionally in protest.

Doctor Grisholm started the engine and reversed out of the alley without another word.

Ten minutes later, just as they were approaching her grandmother's neighborhood, he spoke up again: "So, are you really worried those shorts will be too small?"

"Yes," she said, still sulking.

"Alright then, why don't you try them on? If they don't fit, I'll take them back."

She looked at him skeptically. "Where am I supposed to try them on?"

"Right here. No one can see."

Rolling her eyes she responded: "Except you."

"Well look... I was just offering to help. If you don't want to that's okay, but I'll expect you to wear them on Wednesday."

She lifted the shorts from her lap and turned them over.

"Fine," she sighed.

Grisholm pulled off the road into a vacant lot. The sun remained only a few degrees above the stony horizon. He slowed the truck to a halt on the edge a dirt field and let it idle.

Tiffany took off her seatbelt, unbuttoned the empty shorts and tore off their biggest tags. Then she carefully looped them over her sandal-clad feet and drew them up around her knees. She gave Grisholm a sideways glance before dragging them up to mid-thigh, bunching her dress she did so.

A thin smile of anticipation creased his face.

The shorts already felt tight despite being scarcely halfway on. The next part would be embarrassing, she knew, because her underwear would show. She scooted her bottom forward and squirmed to pull the stretchy denim higher, grunting out little involuntary noises as she finally got them onto her hips.

"See?" she asked plaintively, sitting again and gathering her dress to show him how wide the shorts' unbuttoned fly was across her lower abdomen. "They don't fit."

Grisholm was enthralled. The gaping fly revealed her panty's lace waistband and tiny sheer front panel. He set the parking brake and killed the motor.

"Try buttoning them."

"But, sir... they're already too tight!"

"Just try."

"Urrg!" she groaned in exasperation. She arched above the bench seat and pulled her dress further out of the way. Then she sucked in her bare tummy and pried the shorts' ultra-low waistband together.

Doctor Grisholm chuckled, delighted to see her athletic body wriggling beside him. Her navel rose and dipped as her abdominals flexed to keep her hips aloft.

One by one she managed to get all five buttons closed.

"Oh my God I could never wear these," she whined breathlessly. She tried to sit normally but the shorts dug fiercely into her crotch. "They're so tight they hurt, sir."

"Lemme see the back," he ventured.

She attempted to tug the shorts out of her crotch but they refused to budge. "Please, sir... It feels like half my butt is showing. I can't wear these!"

"Just show me. Come on, roll over."

Tiffany huffed once more, but rolled away from him and propped herself onto one hip.

"See?" she asked, turning her head and pulling her dress askew to show him her thong's exposed side-strap. "They're WAY too small."

He didn't respond immediately.

She inched her bottom backward to emphasize her point.

Grisholm's calm veneer cracked. Right there in the confines of his otherwise unremarkable Ford he was confronting his core vice.

His eyes raked her bare legs, absorbing their uninterrupted display of smooth skin that now reached all the way up to and beyond the pale dents of her gluteal crease. Her posture made the shorts appear to have no inseam whatsoever. Stretchy white denim emerged from the hollow of her crotch in a narrow wedge. Too snug by far, each folded cuff dented her skin as it curved across her butt, evidencing her supple elasticity rather than concealing it. The tiny triangular pockets pointed at the exposed half of their respective cheeks, encouraging his eyes to reverse course and follow the descent of the cuffs back to where they converged on the shorts' thin central seam and disappeared into her crotch.

"Fuuu..." he drooled.

Myriad mental obsessions distilled themselves to one pure object: Tiffany's ass.

"See?" she repeated, snapping her exposed panty-strap against her skin.

Without thinking, he leaned over and grabbed her bottom.

"Hey!" she yelped.

"Shh for a second," he mumbled, barely in control. "I'm just seeing how tight they are."

He lifted her ass, squeezing its soft flesh. Then he worked his thumbs up under the rear of her shorts, stretching the fabric still tighter against her crotch.

"What are you doing?!" she pleaded. "Ow!"

He pried upward, tilting her pelvis until she was mooning him. Her upper body flopped across the cab. She scratched the plastic door panel searching for traction and let out a stream of explicative squeals as he squeezed his grip, cranking the shorts higher and ogling her beautifully petite camel-toe.

In his mind she became essentially naked. He leaned closer and planted a wet kiss on her inner cheek, right beside her anus.

"Let me go!" she responded.

"So... damn... nice!" he whispered, glassy-eyed with lust.

His right hand moved, releasing the rear of her shorts and quickly hooking under her hips. He pulled them closer and higher, almost into his lap. His left hand stretched her butt cheeks this way and that.

Salvaging just enough mental bandwidth to lie, he said: "They don't look TOO tight, Tiffany."

"Yes they are!" she squealed.

He ran two fingers down the dented line of her camel-toe until he found her clit. It was a bump, tortuously pinned to one side by the pressure of the shorts' central seam.

"You mean right here?" he asked, kneading his fingertips.

She gasped.

"Oh, you like that?"

"No! Please don't!"

He stroked her clit again.

"Fuck!" she cried. "You're hurting me!"

"My goodness you're sensitive, honey. I can feel how swollen you are right through your jeans."

"Please!"

He rubbed side-to-side. She kicked her long bare legs and tried to dislodge his forearm from under her hips, but it was useless.

"These are really gorgeous on you, you know that?" he announced calmly, still stroking her clit with two fingers while the pad of his thumb wiggled against the taut layers barely covering her vagina.

Tiffany's head clunked against the armrest and her eyes clenched tight. Her body was responding in ways she did not like. A glow-stick of pleasure connected her clit to her brain and blocked out all rational thought. She knew she shouldn't be feeing this way, but it was overwhelmingly intense.

His fingers kept moving, working her wedgie side-to-side.

"Please!" she whispered, letting go of the armrest and collapsing. Her face and shoulders landed on the vinyl seat. Using both hands she tried to dislodge his stocky forearm but it remained immovable.

For a while he kept rubbing her, saying nothing but clearly relishing her position and burgeoning arousal.

Eventually he spoke: "I tell you what; if you promise to finish what I'm doing when you get home, I'll stop."

"Okay," she whispered, not processing what he meant.

"And wear these Wednesday."

"Yes. I promise. Please just stop, you're really—AH...! Really... "

He let go.

She scrambled from of his lap. Still dizzy, she sat and brushed her dress down to conceal the tiny shorts. Her heart thumped in her chest like a crazed rabbit.

It took Grisholm a minute to recover his senses too. His higher brain functions had ceased while staring at her ass.

"No... sorry actually," he stumbled out of the fog at last. "I didn't mean to scare you there Tiffany, I um, it's just... your skin looked so perfect. I mean, it IS perfect. I couldn't think straight."

She glanced at him once, then looked down at her hands. They toyed with the shorts' top button through her thin dress.

A few moments of anxious silence passed.

"I can't breathe," she whispered finally.

She reached under her dress to unfasten the shorts and let out a gasp of relief as they opened. Quickly she peeled them down to her ankles and started fishing her sandals out of them one at a time.

Grisholm watched, still amazed.