Tiffany's Timidities Ch. 01

He moved his hand to her front and rubbed her slippery clit in tight circles, faster and faster, making her knees weaken with pleasure. Then he hooked two fingers inside her and began shaking her pubic bone. Her short moans escalated, vibrating into his open mouth.

Her panties fell to her ankles.

Just as she was about to cum, he broke contact and spun her away, bending her over the desk again.

"WHACK!"

"AH! Fuck Doctor Ja—"

"Say nine, Tiffany."

"Nine, sir!"

WHACK!

"OW! Ten, sir!"

"Good girl. See how fun this is?"

WHACK!

"Yes! Eleven, sir!"

WHACK!

"Twelve, sir!"

WHACK!

"Thirteen, sir!"

Tiffany's jaw was shivering, chattering her molars until she sucked her lower lip behind her front teeth to quiet them. She panted heavily through her nose, emitting little squeaks of anticipation. Her face was wet and mottled pink.

WHACK!

"Fourteen!"

"Just one more, right?"

"Mm-Hmm! Yes sir!"

His hand strayed to her crotch again, dipping between her inner thighs and then scooping upward to her impatient sex. Her legs danced around and she arched her pelvis higher. He ran his thumb smoothly into her vagina, all the way in, as his fingers scissored her clit.

A guttural cry escaped her. Her body clenched on his buried thumb. She felt like her clit was the size of a golf ball. It was so sensitive she panicked, swinging her arms wildly. Newspapers flew everywhere along with pens and other sundries that had decorated his desk. The empty coffee mug shattered on the floor.

He pressed her lower back down and started banging his thumb into her, clapping her clit.

Tiffany cursed and came. Clear fluid gushed from her pussy, soaking his hand and the backs of her thighs.

"Oh my God you little slut!" he exclaimed as she writhed under him. He had not seen a woman orgasm so strongly in decades.

Tiffany's head twisted back and forth, flailing her short hair and earrings. Her buttocks clenched repeatedly. She cried out as if in pain.

Amidst all this, there was a knock on the door.

Doctor Jacobsen kept fucking her with his hand for several moments and then paused to savor the ebbing contractions of her small vagina. He watched as her nubile body gradually calmed. Her knees ceased their restless fluttering.

The knock repeated. This time they both heard it.

"Who is it?" he asked loudly.

"It's me."

Doctor Jacobsen chuckled. He returned his gaze to the glossy, handprinted bottom between his hands and called out: "Come in!"

Tiffany, through her delirium, discerned that someone new was about to enter the room behind her. She tried to stand, but Doctor Jacobsen kept her firmly pinned over his desk. Post-release endorphins zigzagged through her nervous system. Her ass cheeks felt aflame.

She felt his thumb withdraw as the door opened.

"God... DAMN!" a new male voice said. "She's in trouble already?"

"Yes Doctor Adams, this..." Doctor Jacobsen answered proudly, "is Tiffany. As you can see she's quite a peach. And we're just about to finish up her first disciplinary lesson, aren't we girl?"

Tiffany twisted her head to see this new person, Doctor Adams. She caught a glimpse of sandy hair and a tan face moving across the room behind her, but then he disappeared to the right of her upturned bottom and was out of view.

"Tiffany, I asked you a question." Doctor Jacobsen prodded.

"Sorry sir."

"Do you remember where we are?"

"Yes sir. Just one more, sir."

"That's right. Which side would you prefer?"

"Oh, um... um... my right, please. It's not as s—"

WHACK!

"-ORE! Oww! Thank you... sir. That's fifteen."

"Very good, Tiffany. One for each minute you were late. Now your bottom has a nice warm glow. I think that should serve as a good reminder. Don't you?"

"Yes sir. I won't be late ever again. I promise."

"Good. Doctor Adams? Do you think she looks sufficiently reminded?"

"I'd say so, yes. What a cutie. Do you mind if I...?"

"Not at all."

Tiffany felt a new hand grip the back of her buttered thigh and slide upward to her sensitive ass. She set her forehead onto the desktop with a 'thunk' at the realization that yet another man was now fondling her.

Doctor Adams' hand squeezed her naked ass, one cheek at a time. Then he slid his fingers between and gently traced the slippery folds of her sex.

"My God she's soaking wet. What did you do to her?" he asked.

"Oh, not much," Doctor Jacobsen answered nonchalantly. "But I agree, she did seem to enjoy it in the end."

"I'll say! Her labia are small but they're totally enflamed."

Tiffany wanted to die. Nothing in her wildest dreams could have anticipated this level of humiliation. She rocked her head back and forth against the table, unable to conjure any defense of her self-worth.

She felt Doctor Adams' second hand join-in. They pried her throbbing cheeks wide apart.

"Wow," he spoke solemnly, "What a tidy little package. How old are you, Tiffany?"

She lifted her head and shivered at the novel sensation of two thumbs astride her anus, stretching her soft skin in opposite directions. "I'm... I'm twenty-two, sir."

"Have you ever tried anal intercourse?"

"God sir, no!"

"Well, that's a shame. You have a perfect ass for it."

She had no idea what might happen next. Her pulse thudded loudly in her neck and temples. Her anus puckered, tightening itself into a miniscule knot as the two doctors looked on.

They exchanged a glance. Both grinned.

Doctor Jacobsen was next to speak, finally lifting his hand off her lower back: "Tiffany, you may turn around now and greet Doctor Adams properly."

She straightened up so quickly that she got a head-rush and nearly lost her balance. The lower half of her dress fell back into position, covering her naked hips. Her thong remained at her ankles though. She shuffled her feet around.

Her push-up bra stood well clear of her sagging dress, holding her young boobs daringly aloft. Two pink half-moons of areola showed above it. Her hard nipples protruded obviously outward, barely concealed by its top edge.

Doctor Adams offered her a damp handshake. She accepted his grip while attempting to tug her dress upward.

"Nice to finally meet you, Tiffany," he said, "I'm Doctor Adams."

"Thank you sir. It's nice to meet you too. Sorry it had to be... like this. I'm not—"

"Nonsense," he grinned, pumping her forearm up and down so hard that her breasts shook, "I can't imagine a better way to get to know our new office girl. Welcome to the team!"

Tiffany cringed but tried to keep smiling. She realized that Doctor Adams was by far the best looking of all four partners. He looked like a forty-year-old Robert Redford.

"Um... okay," she smiled weakly. Had her face not already been fiercely blushing, it would have begun to now. His steel-grey eyes bored into her, bracketed by crow's feet that creased his tan. His teeth were clean and white but irregular enough to look honest. Scattered grey hair seasoned his honey-colored locks. His hand felt big and solid around hers.

After a moment of silence he broke their gaze and addressed Doctor Jacobsen: "Do you mind if I take Tiffany for a while?"

"Of course not," Jacobsen said. "We're all done."

"Great. Come on, sweetheart. Let's go to my office."

He allowed Tiffany to pull her thin panties up, but then quickly towed her from the room by one hand. Her shoes clacked along unevenly behind him as they navigated two turns into the room next door.

SCENE 5

Adams shut the door.

His office was messier and more comfortable than Doctor Jacobsen's. The blinds were pulled down and the only artificial light came from a brass desk lamp with a green swivel-shade.

He led Tiffany around behind his wide built-in desk, rolled his chair away and brushed a pile of mail back from the writing surface.

"Have a seat," he encouraged her, gesturing to the cleared spot.

Tiffany carefully inched her still-glowing bottom up onto his desk and scooted backward, tugging the lower hem of her dress down to cover as much of her thighs as she could. Doctor Adams flopped into his chair and looked her up and down. Then he rolled forward and lifted her shoes to his lap. Tiffany tried to cross her legs but he caught her bare calves and stopped her.

"You looked pretty excited in there. How's your first day going so far?"

"Uh, it's... its' not what I... I didn't expect you guys to—"

"The spankings? I know. I told them that was crazy."

"Really?"

"Of course, I mean... this isn't Victorian England."

"Exactly! Right? Why didn't they—?"

"I got outvoted three to one. So... here we are."

"No, it's gotta stop! I'm not like, okay with it... sir."

"Well you seemed pretty lit-up when I saw you."

Tiffany looked away. She could not admit that to herself yet, let alone to this gorgeous man holding her knees slightly apart.

"I think your body has different ideas," he continued soothingly, "about what it enjoys."

"NN-mm," she shook her head, still unable to look at him. "No it doesn't. You guys are doctors. You're my employers. You can't just..."

Doctor Adams moved his hands to her thighs and pushed her dress back softly.

She tensed.

"This all seems very strange to you, I know," he said quietly. "And since it's your first day, you're probably feeling extra sensitive but I think... what you need now is some way to calm your nerves."

"Nn-mm." "This will make your whole day seem easier," he whispered as his elbows spread her legs apart and his face dove to her crotch. Tiffany slumped backward, gasping loudly as his mouth latched onto her swollen vulva and sucked her clit and labia through the sheer panties.

"Oh Doctor! What are you—? Stop! Oh... God!"

She clawed at the desk behind her, trying to scoot away, but he pulled her hips firmly closer. His mouth attacked her pussy so adeptly that her panties may as well have been invisible.

She struggled but his hands bent her legs back until her feet were over his shoulders. She tipped backward, onto her elbows.

Within seconds Tiffany's neck slackened as her groin endured a flood of ecstatic sensations. It had been ages since anyone had gone down on her, and after her gushing orgasm in Doctor Jacobsen's office her body was well-primed for more.

She stopped fighting altogether. Adams took a breath and yanked her underwear to one side. Then he immersed his tongue inside her folds, licking and sucking every millimeter of her bare sex into his mouth. Tiffany collapsed completely and grabbed his head.

"Oh God, oh God, oh God, oh God..." she panted. He was obviously an expert at this.

His hands pushed her legs farther back, folding her knees to her chest until her shoes were inverted high above her face. Her toes curled-up tight.

He peeled her panties out from under her and gathered them into a rope around her knees, enabling him to keep her legs pinned back with just one hand. His free hand then took up a position alongside his chin, thumb extended to probe her labia. Moments later he buried that long digit deep inside her, rocking it back and forth while her clitoris grew inside the vacuum of his mouth.

Tiffany's little body squirmed against his face. Her tailbone lifted off the desk.

He shivered his mouth against her, slurping her folds between his lips while his thumb probed her narrow depths.

For Tiffany, each successive minute of this was more ecstatic than the last. Finally she let out a desperate and plaintive cry.

Juices from her interior mingled with his saliva and trickled down the crack of her ass. The tempo of his mouth and thumb accelerated.

Her fists balled. One strafed his desk while the other lodged itself between her teeth.

Her clit was being pinched between his lips and shaken. His tongue flicked like a rabbit's foot. Then he wiggled his index finger into the slippery ring of her anus.

She felt all her orifices tighten at once. His finger push deeper and wiggled.

He chose that moment to suck her clitoris extra hard.

She screamed as the climax hit her. It arrived with the force of a rogue wave, crushing everything in its path. Her jackknifed body quaked and wriggled. Her breathing stopped.

As she came Doctor Adams carefully squeezed a second finger into her ass. Still he flicked and sucked her clit unabated.

A string of wavering sobs burst from her throat. Her hips jerked under him. Fresh secretions oozed from her.

Finally she grabbed his hair and shoved him away. It was too much.

He raised his face, sucked in a lungful of air and surveyed her body.

Her outer labia were puffy and gaping. Her delicate inner petals were bright pink and awash in lubricant. The head of her clitoris held itself high, entirely too swollen now to fit beneath its narrow hood.

His fingers remained half-inside her slippery butt, gradually creeping outward.

"How's that for a warm welcome?" he asked through a greedily glistening grin.

Tiffany rocked her head from side to side, unable to speak. Eventually she reached down and pushed his hand from her ass. He obligingly removed his fingers, but kept her legs pinned back for a moment in order to watch her pale anus recover its pucker.

Then he released her knees and sank back in his chair. For the next dozen seconds he simply admired the sprawled beauty lying atop his desk.

Her slender legs were slack, draped wide apart. Her sandals were heel-to-heel in front of her butt. Her nipples pointed at the ceiling, having completely escaped her bra.

Her petite, carefully-shaven pussy was in full bloom; slick and aglow.

She tried to sit up, but only managed to get to her elbows. Her eyes were half-lidded. Her feet slipped off the desk and fell, drawing her legs somewhat closed. She gazed at him sleepily.

He stood up and eclipsed the distance between them in a single step. She did not move other than to track his approach. He bent over, cupped her face in both hands and pulled her into a kiss.

Tiffany was so far gone she answered his tongue's probing requests with eagerness, kissing him back as though he were a newfound boyfriend. Her heart fluttered in her chest.

None of this made sense. She was hooking-up with another of her new bosses, giddy after a pair amazing orgasms. Anything seemed possible now.

It was nine fifteen in the morning.

*