Tiffany's Timidities Ch. 03

"Touch yourself, Tiffany, with that; right where we talked about."

Her eyes flicked up to his. Her blush deepened. "Now? In front of you?"

"Yes. And look at me while you do it."

Her shoulders cringed forward, squashing her breasts together. But she knew she wanted this.

Everything he'd told her so far had felt good. She was starting to believe he understood her fantasy-world better even than she. And maybe, she thought while looking into his dark eyes, maybe she really was a passenger, sexually-speaking at least.

He stared right back, unforgivingly perceptive.

"I've..." she whispered, looking back down at her hand. "I've never had one of these."

"Never?"

She shook her head.

"Oh Jesus, Tiff'... I have so much to show you. Now put that on your clit and look at me."

She lowered the little toy down until it was against her trimmed pubes, then paused, not quite brave enough to continue. She looked up at him, needing more.

"Lower," he said.

She crept the buzzing thing down, sliding it onto her clit's swollen hood. Instantly her eyes flashed wide as pleasure rushed in.

"Find that spot," he instructed her sternly.

She was aware of his arms moving around, brushing her hips as they fiddled with something behind her. The vibrator soon eclipsed that awareness, however, at the very moment it touched the right side of her clit.

"HHHNNG! N'God!" she whined. Fresh flames of joy lit her crotch, reaching high into her core.

"Yes!" Grisholm hissed, relishing her expression. "Keep it right there!"

She fought for control of the little bullet, trying to do as instructed but almost fumbling it in her slippery juice. Keeping it on her most sensitive spot was too much to ask. It was too strong and too outrageous in its effect. Her eyes rolled back.

Grisholm lifted a hand to her chest, taking a break from whatever he was doing behind her, to raise the silk shell off her breasts. Then his mouth latched onto one of her distended nipples and started sucking.

She squealed anew, incited by this diversity of pleasure.

Then, as if that weren't enough, she felt something nestling between butt cheeks, almost like finger but cooler and smoother. It pushed up against her backdoor.

She gasped. He sucked her nipple harder while his lower hand pushed.

An inch of something penetrated her butt.

"AHNnn-NN!" she wept, shaking her head so that her earrings and disordered hair swung.

Still the bullet buzzed her clit, her own fingers unmoved by her anxious dismay.

His mouth came off her nipple with a pop and he beheld her open face.

"Just relax Tiffany, and keep that vibe on your clit like a good girl."

Both his hands were behind her butt again, clutching the narrow butt-plug he'd covered in lube.

He pressed it higher, incrementally widening her anus.

Her head tipped rearward and her young spine arched, lifting her breasts toward him. Still the bullet remained in place, held by obedient fingers.

Carefully he adjusted a knurled dial on the insert in the butt-plug's narrow stem, rotating it until the vibrator inside came alive.

Tiffany fairly exploded, snapping forward so hard she almost head-butted him. Her buttocks, hands, feet and face all clenched at once, then a guttering sob burst from her mouth and she buried her head against his shoulder.

"Surprise," he whispered.

She heaved-in a wet breath and then began to bounce and shiver, moaning against his collar.

"That's in your ASS, Sweetheart. And you're loving it."

This goading only worsened her condition. She was non-verbal, awash in pleasure, having gone from never having experienced a vibrator to being caught between two at once. Her vulva conveyed pure liquid joy.

He inched the little plug in, deepening its vibrations. Her hands were sliding all around her mound, unable to keep the silver bullet in place. It really didn't matter anymore though; everything felt too good to be evil and too intense to resist. All she had to do was hang on.

The rubber plug slowly widened it climbed, turning her every breath into a moan.

She was bouncing rhythmically against him now, evincing her body's native impulse to fuck. Combinations of pleasure heretofore unknown stripped the last remnants of shame away, leaving her primal hunger exposed.

She bit his collar, then turned to his neck and sucked, desperate to satisfy all her cravings at once. He brought a hand up behind her head, grabbed her hair firmly and relocated her lips to his own.

They Frenched through her moaning, tongues to the hilt, right up until the moment he shoved the toy home.

That made her scream.

She dropped the silver bullet, reaching back instead to search for the plug. He held her tightly, pulling her head by the hair, and covered the toy's rubber base with his fingers.

"Fuck no!" she cried toward the ceiling, clawing at his hand.

He kept the base steady, letting the toy buzz in her rectum.

"Shhh..." he soothed her. "Just leave it."

"No I can't, I can't, I can't... oh God!"

"Yes, you must. This is your training."

"No, please! Please take it out!"

"Not yet."

"Please! It's so fucking big!"

"No, it's not, T'. It's a wisp of a thing. You're just way too tight. You need to calm down; relax."

"Please..." her voice softened to a whimper. "Please."

"This is your punishment. You will wear it all morning."

"Oh, God no. No way."

"Yes. And if I catch you taking it out, you'll get a spanking and then a bigger one."

"Ah—a bigger what?"

"A bigger one of these," he emphasized, tugging the neck of the toy outward against the vice-like grip of her ass.

"Fuuuck!" she wheezed. "Don't do that! It's killing me!"

"Such a dramatic little minx; you know that?"

"But it's ON, sir! You can't expect me to work like this."

"Well, I suppose that'll teach you to pay more attention to detail, won't it?"

"Oh God, sir... please take it out. I can't... I can't meet people... out in the lobby. Not while it's in me. Fuuuucking ay... at least turn it off!"

He brushed her hands away and let go of the plug, telling her to leave it alone and not swear so much. Then he pushed her up onto her feet.

Once she was vertical above her tall shoes he hoisted himself from the floor as well.

He checked her plug once, just to make sure it was still firmly planted. Her tiny asshole was cinched so tight around its neck that nothing could have dislodged it without significant pain.

Then he instructed her to get dressed.

He walked, smiling, back to his swivel chair and sat down. The left-hand bottom drawer was still open.

"Your skirt," he added calmly. "Will conceal the base of the plug and you'll be fine. I'll let Mitchell know we decided to forego your spanking in exchange for this."

"But—"

"Hurry please. The doors open in just a few minutes."

Tiffany squatted carefully to retrieve her underwear and suede skirt from the rug. She stepped into her g-string and then slowly straightened, raising it up onto her hips before wrapping the miniskirt around her waist. Lastly she collected her grey headband from among the pillows and used it smooth back her hair.

"I should go clean up, sir," she said, facing him, traumatized. "I'm sure I look ridiculous."

"You look adorable," he answered honestly. "But sure, that's a good idea. Before you leave would you mind cleaning up the rest of those toys off the floor?"

She looked at the colorful pile and empty Ziploc bags beside his desk. Without hesitation she stooped over and cleaned it all up, sealing both bags snugly before handing them over.

"Thank you," he smiled.

SCENE SIXTEEN

A few minutes later Tiffany was perched atop her tall stool in the lobby, alone. The front door was unlocked and the message indicator on her headset was blinking. The daily scheduling calendar looked moderately busy. She glanced outside through the glass entryway and saw two cars turning into the parking lot.

"Mother of Christ," she whispered under her breath, "How am I gonna do this?"

At least Doctor Mitchell had let her wear her sweater again, abiding by his rule that she be allowed one item of business-appropriate clothing while in front of the patients. Her skirt was still far too short for comfort however, especially considering the rubber toy still quietly blurring the interior of her rectum.

She put on her headset and dialed into the voicemail system to retrieve the new messages.

Beneath her short skirt the vibrator ran continuously. She tried crossing and uncrossing her legs to ease its intensity while somehow managing to transcribe the voice messages into her touchscreen. It wasn't easy.

When she hung-up, the front door squeaked and the day's first two patients wandered in. She climbed down off her stool very carefully to greet them, trying to keep her voice from betraying her breathless state. The butt plug was giving her chills.

She had to fetch milk for one of the visitors' coffee, and remembered to squat to access the low mini-fridge, rather than bend over, as she knew her brief skirt and ribbon-thin panties were useless in terms of coverage. The plug's stubby base would be obvious if she bent from the hips.

Especially in such tall shoes.

The morning's remaining hours unfolded in an incessant haze of arousal and discomfiture. She did her best to mask what was happening to her but the clear Plexiglas podium offered little concealment and Grisholm's device played an unmerciful game.

Despite her buttoned-up sweater she had to keep her elbows tucked-in due to the immodesty of her nipples. Every patient stared at her. She was in no doubt that this was her life's most embarrassing day.

The older male patients in particular were agog at her condition. The flush across her cheeks was obvious and the shocking brevity of her skirt didn't help either.

Tiffany felt as though everyone knew she was on the verge of losing control. Worse, whenever she sat down the vibrations reached deeper. Sometimes they made her unexpectedly whine, mid-sentence, or even gasp a little by accident.

Each of the doctors visited her often; ostensibly to check the schedule but often just trying to coax her into the hallway for a quick grope.

She abandoned all hope of removing the trembling toy. It was pointless; she had no idea where to hide it if she did take it out, and felt sure the doctors would keep checking her often.

Getting caught without it would be awful. The last thing she wanted was a larger one AND a spanking. Besides, as the hours wore on, the little thing's battery waned, reducing its intensity to a survivable level.

Doctor Mitchell, for one, seemed more interested in the number of appointment-calls she was fielding. He clearly trusted the news of his sexy new receptionist would spread quickly to every young man in the county. To his mind anyway, her ongoing exhibition seemed like perfect fodder for word-of-mouth marketing.

Tiffany, on the other hand, found it difficult to focus on such commercial concerns. Her thoughts were far too colored by arousal. The fact that she'd kissed every one of her bosses earlier wasn't helping. It made her interactions with them seem overtly sexual.

By a quarter to one the lobby was empty. She was hungry, footsore, overstimulated and slightly hung-over.

Mitchell appeared at her side holding, to her delight and surprise, a frozen popsicle.

"Here," he smiled. "I made a batch this morning."

"You did?" she asked, eagerly accepting the proffered treat. "What flavor?"

"This one is vanilla but there's also a salted-caramel batch. Let me know how you like it."

"Gee, thanks!"

She gave the whitish column a lick and then, after a short pause, grinned and said: "Not bad."

"Great. Come get another when you're done. They're protein-pops; my very own recipe. With all the good stuff in there, a few in a row can actually be a meal-replacement."

"Really?" she asked, genuinely interested. She licked the icy phallus again and then inserted it into her mouth. Her cheeks dented and she rotated the handle several times, polishing its first inch.

Ian stared, mesmerized, as she withdrew the whitish thing and swallowed. He chewed the inside of his cheek, praying she wouldn't recognize the underlying taste.

She slurped the popsicle noisily, happy to have a healthful distraction from the buzzing inside her butt.

When she noticed Mitchell's rapt attentiveness, a novel insight dawned on her as well. It wasn't difficult to guess his thoughts, and a certain element of her newly-freed id decided to try an experiment of sorts. In her present state it seemed like a fun idea.

She widened her blue eyes, emoting as much innocence as she knew how, and gradually slid the popsicle deep into her mouth. Then, while staring upward at Ian, she sucked and sucked, denting her cheeks all the way and repeatedly fluttering her eyelashes. Her forehead wrinkled as if in need of his approval.

Ian stopped blinking.

Still playacting, she eased the cold shaft slowly out, letting her tongue emerge to drag its underside. When the tip came out she grinned openly, sloshing a pool of the melted mixture around on her tongue before swallowing and smiling again.

Ian still hadn't blinked.

She wanted to laugh, but instead bit the popsicle and chewed it, making him flinch and look away.

He suddenly remembered to appear less fascinated, but it was too late; she already had him pegged.

"It's tasty, sir," she said around the chewed-up mouthful. "I guess I was hungry."

He felt relieved and delighted, but also uncharacteristically self-conscious.

"Well," he fumbled, "I'd better get back to work. When you're done with that why don't you come get another, you know... so you can try the other flavor."

"Sure... and listen; I'm sorry about not reading my contract. I—"

She cut herself off as the vibrations in her ass suddenly ceased. The battery was dead.

"Wow..." she whispered, completely losing her train of thought.

"What?" Mitchell asked. "Everything alright?"

"Y—yes. It's just this... thing... I'm doing for Doctor Grisholm."

"Oh, right. How's that going?"

"Fine. It was just... really distracting, but I... I think I, actually sort of handled it."

"Good. Well, keep sucking that. Don't let it drip."

"Okay," she smirked, glancing up at him. She briefly extended her tongue and gave the icy shaft a demure lick.

Ian watched a moment longer, longing to see more of her tongue. He figured she had an inkling of his principal fetish, but felt confident she was oblivious to the quantity of semen she was ingesting.

When her tongue declined to play along, he forced himself to walk away.

He wanted her little mouth on his cock acutely; but that had to wait.

Anyway, having a headful of such anticipations is a marvelous torment.

He retreated to his office and shut the door till it clicked. Then he dropped to one knee and began opening the heavy FedEx parcel.

His plan for Wednesday's training would make Grisholm's look like a cakewalk.

*