Ashley Delivers a Pizza

Author's Note: I have become distracted by this side story, but I do intend to get back to the main story soon. As always, comments are greatly appreciated. Please do not hesitate to reach out with feedback. Thanks to Fifth Estate and my other beta readers. Also massive thank you to TSF, out there fighting plagiarism.

All characters depicted are age 18 or older.

It was Ashley Carter's first day at work. Not only had she just transferred to Wayside High and joined the cheerleading squad, she had also secured a part-time job at Pepe's Pizza. Since her older sister had just graduated and gotten a real job, she had handed down her old rusty car. It was a discontinued, but distinct model, the Skyliner. Now that it was hers, she had the means to apply for the pizza delivery position.

Pepe's Pizza had a delivery window guarantee. Lately, Pepe had gotten so busy, likely due to the prospect of free, slightly late pizza. His nephew had started off as the delivery driver, but no one wanted to tip the greasy, squeaky voiced young man. So Pepe had advertised for a delivery person and when Ashley came in to interview, he immediately knew he had his new driver. The girl was nice and pretty and seemed reliable. That was all well and good, but Pepe knew her massive breasts and big bouncy butt would be tip magnets. He agreed to hire her on the spot, shaking her hand vigorously as he watched her rippling, supple cleavage.

As a small business owner, Pepe had to be shrewd. There were no two ways about it, sometimes corners had to be cut. In this case, he didn't even bother ordering Ashley a new shirt. The one his nephew had used would probably fit. It was a small, but she was about the same stature, at least height/weight-wise. And of course, he still had the hat. Pepe let the girl choose the rest of her uniform.

"Checking in for work!" Ashley said cheerfully, entering the small dining area at the front and striding behind the counter, smiling her easy, bright smile.

Seeing her report to work only confirmed Pepe's confidence in her tip-generating curves. Ashley stood at the counter, smiling happily. She had a large, heart-shaped face and big blue eyes. Her brownish blonde hair was shiny and soft and bouncy. She was nice and sweet and eager to please. She wore sneakers, daisy-duke style cutoff shorts, a baseball style white t-shirt with red sleeves, displaying the Pepe's Pizza logo on her chest. She also wore a red baseball cap with the same logo.

Pepe eyebrows raised as he regarded her. Ashley had taken the liberty of modifying the nephew's old t-shirt by cutting a long slit in the neckline. Her swelling cleavage was on display, bulging pleasantly with the slit cut in the neck, running just into the top of his logo. The white material of the shirt was stretched over her huge perky breasts and Pepe could clearly see the darker pink color of her large nipples. She obviously was not wearing a bra.

He smiled, seeing dollar signs appear over her barely concealed nipples in his mind's eye like pasties. He imagined the tips his teenage delivery girl's rack would rack up, eyes widening. Ashley paused a bit awkwardly, hands on her hips while her new boss stared. It was a common occurrence. She was used to eyes sticking to her chest. Pepe forced himself to move his eyes from her breasts up to her smiling face, then cleared his throat.

"Ok, today is usually our busiest lunch shift, so you should get loads of tips. We have two orders for deliveries to different addresses. Do you think you can handle two in a row?"

Ashley thought for a moment, then nodded. "Good," Pepe replied. They checked the boxes and stacked them into the insulated carrier.

"The first order is for the Office on the north side of town," Pepe explained. "The other one is across town, at the library." He zipped up the carrier and handed it to Ashley. "Remember, you have to meet the delivery window, or the pizza is free."

"Yes sir, I won't be late," Ashley assured him as she left the store with the big black carrier. Pepe took a moment to observe her bubble butt in the short denim cutoffs.

"Make sure you are on time, otherwise it's coming out of your tips!" he yelled after her.

Ashley hurried to her old Skyliner and put the insulated carrier onto the passenger seat before climbing behind the wheel. She jammed the old rust bucket into gear. The vehicle wasn't fancy, but it was reliable. And free, so the price was right.

'Geeze, I didn't realize how much of a perv Pepe is,' Ashley thought as she began her delivery route. 'He was practically undressing me with his eyes. I hope the uniform isn't too revealing. This t-shirt doesn't really fit over my chest...'

Her mind churned anxiously as she routed to the Office, eager to make her first delivery run a success. She pulled into a spot marked "Visitor" and retrieved the first pizza from the insulated carrier. She took a determined deep breath, then crossed the parking lot to the entry of the building with the large flat box. This was her first actual job, not to mention the first delivery, and she had no idea what she was doing.

Pepe seemed to mention tips a lot, so that must be important. She would have to make sure to focus on that.

-----

Carson Dixon was immensely pleased with himself. He sat across from three young Asian investors that he was courting for a new account, a career staple type of account. His firm at the Office had pulled out all the stops for the investor team, flying them out from the east coast, setting them up with penthouse suits in the nicest hotel in town, really spared no expense. Now was the critical hour. They needed the investors to sign. His boss, Ms. Lacey, had even gone as far as setting up a stripper.

And he had to admit, the deck of slides his interns had assembled was impressive and the investors reacted favorably. Carson had aged into management and was worried about losing touch with the future generation, but it seemed that his new interns had struck a chord with the young Asian businessmen. Now that the meeting was wrapping up, they would move to seal the deal.

"Gentlemen, you see that our firm can provide the exact services you require. As you deliberate further, I have a little surprise for you that should be arriving momentarily," Carson said with a wide smile.

The investors were childhood friends from an affluent neighborhood in Tokyo. They huddled together, speaking in low firm voices. Akio, Hiroshi, and Nobu had pooled their substantial inheritances and invested wisely. This firm was already a top contender as their next big step. They just needed the opportunity to break through. This Carson Dixon seemed to be their man.

"Very good, Mr. Dixon," Nobu said in his halting but firm voice. He was the most outspoken of the three, though shorter and stouter than his friends.

Hiroshi was the tallest. He nodded his approval, the knot of his hair on top of his head bobbing slightly. Akio also nodded, smiling a tight-lipped smile. He had the barest trace of facial hair, unlike his clean-shaven partners.

Just then, a firm series of 3 knocks rang out on the door of the large conference room.

"Come on in!" Carson said eagerly. "And make sure you lock it behind you," he added, watching as the stripper entered, carrying a box, apparently pretending to be some kind of delivery girl.

-----

Ashley stood at the end of a long corridor, looking at a big door in the middle of a beige wall. The carpet was also beige, as were the paneled ceiling tiles. She hated office buildings.

'This place is like a maze,' Ashley thought. 'The receptionist said the lunch room was down this hall, sixth door on the right.'

"Dick Butkus Conference Room?" Ashley read the sign on the door. "Hmm, maybe someone inside can point me to the lunchroom. I don't wanna be late..."

She stepped up to the door and gave it three firm knocks.

Upon hearing, "Come on in!" from the inside, she opened the door and entered. One of the men inside instructed her to lock the door. A strange request since she was only here to deliver pizza, but she made sure the door was locked anyway.

"Pizza Delivery!" Ashley said proudly, her big tits jiggling in the tight shirt as she held the pizza below them.

Carson regarded the curvy young woman holding the pizza box. She had thick blondish-brown hair, tucked under a red baseball hat, big blue eyes, and a broad white smile. His eyes fell to her big tits, and he could see her darker nipples right through the thin white material of the t-shirt.

'These strippers seem to get younger and younger. And I guess they have no problem dressing like complete sluts,' he thought, standing, and crossing to her.

"Oh, is that the extra-large we ordered?" Carson said, stepping up to her and staring at her big tits.

Ashley smiled, turning back and forth slightly. It was time to earn her tips.

"Yes sir," she said cheerfully. "It's fresh and still hot!"

He continued to ogle her, taking the box, and moving behind her to check out her ass.

"Wow, you aren't kidding. Looking piping hot to me," Carson said, putting the box on the table, then putting his hands on Ashley's waist from behind. "Ok, so did you bring a speaker or anything?"

Ashley was confused as the older man took the box, but then puts his hands on her waist.

"Uhm, a speaker?"

"Yeah, usually the girls bring music..." Carson said dismissively, using his hands on her waist to guide her to a group of seated younger Asian men.

"Oh, they only gave me the pizza," she said, confused, letting him guide her.

The young men shifted their chairs to allow her to stand in the middle. They were all staring at her with excited looks of anticipation.

'These guys must be really hungry,' she thought to herself. 'They are looking at me like I am lunch...' Ashley felt her nipples stiffen in the thin top. The worn material was a bit scratchy and was stimulating her nipples. She had very sensitive big pink nipples.

Carson was staring at her chest from over her shoulders behind her. As he watched, her nipples rose as if to announce themselves to him. His cock stirred in his pants as he moved his hands from her hips to her shoulders.

"Well, we certainly don't care about music if you don't, right boys?" he said with a chuckle. "I'm Carson. This is Akio, Hiroshi, and Nobu." He indicated each with the wave of his open hand. "Now if you wouldn't mind, I think the boys would like you to start by taking off your top... Miss...?"

Ashley's mind rang momentarily, causing her to tilt her head. 'Start by taking my top off?' She thought that was an odd request.

"Um... Ashley... my name is Ashley," she heard her voice say mechanically. The man behind her was turning her back and forth by her shoulders as the seated young men watched. Their heads were at eye level to her tits, and they were swaying heavily as Carson showed her off.

Her nipples stiffened even further against the rough fabric, and she felt her pussy throb.

"Did you say take off my top?" she said quietly.

Carson didn't hear her though.

"Hmmm, never heard of a dancer going by a regular name like Ashley before..." he said absently, but boy was he eager to see her topless. "Out of the ordinary, but nonetheless, nice to meet you, Ashley. Now let's see those big tits!"

Carson reached in front of her and pulled up the crop top.

"Oh, uhhhm..." Ashley said, lifting her arms as the tight material was pulled up her body. Then her head and arms were bunched in the shirt. "oooff..."

Her soft, massive tits lifted with the tight shirt at first, but quickly succumbed to gravity, tumbling out heavily before coming to rest high on her chest, perky and round. Carson hastily tugged the thin shirt over Ashley's head and beheld her huge teen tits in all their glory from above and behind her.

"Jesus Christ, what are they feeding you girls?" he marveled, balling up her shirt and tossing it aside.

The three seated men gasped.

Ashley sighed as her bare nipples hit the air. 'Oh god, it feels so good to get them out of the shirt,' Ashley thought. 'That material was driving me crazy...' She smoothed her palms over her aching stiff nipples. 'This should definitely improve my tip,' she realized, smiling.

But her hat had fallen off. She couldn't have that. Ashley bent to retrieve it and then stood with her legs slightly parted, gathering her long soft hair. She secured it into a ponytail and put the hat on, letting her hair thread through the hole in the back.

"Well, it's my first day and I'm not really sure what I'm doing. I hope this is ok?" she said, putting her hands on her hips and smiling, topless.

Carson had crossed in front of her. His eyes were laser-locked on her tits as she adjusted her hat. His hands were rising, palms toward her with fingers curled open. "You won't mind if I..." he said softly just before his large hands roughly latched onto her supple orbs.

"Oh, Mr. Carson," Ashley sighed, her hands holding onto her hat as the man suddenly grabbed her.

"Holy shit boys, these knockers are real!" Carson reported before lowering his face and lifting Ashley's heavy tits to his mouth. "MMMMnnnNNNMMM," he said, slathering spit from one large nipple, back to the other, nipping, pinching, and squeezing as he explored the girl's chest, having no idea she was here to innocently deliver a pizza.

"Oh... um, Mr. Carson," Ashley sighed. She absolutely went crazy when her tits were played with, and she found herself suddenly a bit weak-kneed as he went to town. "Mmmm," she cooed. "I hope this will earn me a nice big tip..." she said absently, moving her hands to his shoulders for stability as she started panting.

With his face in her cleavage, he adjusted himself. 'Hmmm, already asking about the tip? This one is a real slut; I wonder if she'll let me fuck her...' Carson's mind ran as his mouth worked. He felt her arch her back, encouraging more attention. '...said it was her first day...'

He lifted his face, now smeared from sucking on her stiff nipples. "You boys must have a squeeze. Ashley's tits are phenomenal," he said, turning her by her shoulders and moving her closer to one of the guys. Her bulging tits wobbled as she settled into place.

The seated young man was smiling at her with a crooked smile. He was dressed identically to the other young Asian men, non-descript dark suit, white shirt, dark tie. The first guy was the shortest of the group, but Ashley couldn't remember his name. She had been too distracted to register any of their individual names.

She looked down at the top of his head. He had dark, straight, shiny hair.

He was staring at her huge bare tits. "Very nice to meet you," Nobu said haltingly as his hands followed his eyes to her breasts.

She rested her hands on the young man's shoulders as he palmed her tits forcefully. Ashley sighed. His hands were smaller and smoother than Carson's, but still strong. He eagerly squeezed her perky boobs, then pressed them together from the outsides. His eyes leveled at her chest, and he seemed to speak directly to her tits as he groped her.

"Mmmm nice... big... soft... Very good luck... Big tits very good luck." He let go of them long enough to remove his glasses and place them carefully on the table next to him.

Then, suddenly --WHAP-- the young man's face was buried in her supple cleavage in a flash, making a wet fleshy sound as his face impacted her chest.

"Ooooh... um... nice to meet you too. Mmmmm, that feels nice... What did you say your name was again?" Ashley said, her hands easily resting on his shoulders as he attacked her tits. He was too distracted to reply, and she grunted as he loudly slurped on each nipple in turn.

'Oh god, I'm getting so wet now,' Ashley realized, squirming as her bare thighs rubbed together in the short cut-offs. She could feel how slick they were already. 'Maybe I should have worn panties...'

Nobu moved his hands to Ashley's waist and lifted his face reluctantly. He passed her to Hiroshi, who had his turn with Ashley's breasts. Hiroshi then passed her to Akio. Ashley felt the wispy facial hair of the third boy tickle her breasts and tummy as he groped her fervently.

Ashley grew more and more aroused as she was passed around and manhandled. She wasn't sure this was part of the job, but she couldn't stop them. She loved the attention to her big sensitive breasts. It was making her pussy throb and ache. The boys enjoyed another round with her tits, ardently exploring the curvy American teen as she stood between them in her sneakers, daisy dukes, and the red baseball cap. Her breasts grew reddened, and her head swam with all the attention, looking down to see two mouths on her tits, one around each nipple. She could feel the young men's tongues swirling vigorously. Her pussy was on fire.

"Oh gosh and here I thought I was just delivering a pizza," Ashley said, grunting in response to their treatment. "I guess it's okay though...." Ashley huffed, "as long as I get a nice big tip..." She fought the urge to touch her aching slit and firmly bit her lower lip.

Though none of the young investors heard Ashley's comment, Carson thought this was part of Ashley's "act" and was all for "playing along". He heard her mention getting a "nice big tip" and he knew what that meant. TIP was just "stripper speak" for "I am willing to engage in sexual activity for money and am now ready to start."

"You heard her boys, she wants a big tip," Carson said, unzipping his pants and unbuckling his belt.

Ashley stood flat footed on the carpeted conference room floor. She had one hand on each shoulder of the two seated men with her hard nipples in their mouths. She heard Carson say something, but the words were indistinguishable to her in her stupor of arousal. But even in that condition, she recognized the sounds that followed:

Slight jingle as the belt is unbuckled...

Much louder zipping sound as the fly is lowered...

Muted shuffling of fabric withdrawing...

Before she could turn, she felt a thick round shape nudge against her left butt cheek as it stuck out from the bottom of her cut-offs. Then the warm shape prodded her right cheek, leaving a wet trail over them. As she turned slightly, Carson took her left wrist and guided her hand to his shaft. The girl had closed her fingers around it before she knew what she was holding.

Ashley gasped as she turned, pulling her tits out of the suctioning mouths with a wet POP, looking down at the thick hard cock in her hand.

"Mis-mister Carson!" she shrieked, wide-eyed. The hand without a cock in it clapped over her mouth. Her head tilted down, and she observed his girthy twitching erection, palming it fully.

Carson proudly rocked forward onto his tiptoes, turning the topless girl to face him squarely. Her enormous spit-sheened tits wobbled as he held her shoulders. His eyes were locked onto them.

"How's that for a big tip my dear!" he said jovially. "Now don't be shy, use both hands," Carson instructed, hands on Ashley's shoulders. "One of you boys be a gentleman and give up your seat for the young lady."

Being incredibly aroused, but new to the job, Ashley was docile and submissive as a rolling swivel chair was placed behind her. Carson pressed on her shoulders, and she sat down, moving her left hand to join her right on his dick. Her eyes leveled with the solemn one-eyed gaze of Carson's fat knobby head. It was the shape of a large lemon and shiny.

It throbbed in her grip, reddening.

"That is a big tip," she observed, both hands gripping the wobbling pole, fingers not quite meeting around his meaty cock head. She looked up as Carson shifted forward, sliding his thick shaft toward her, through her grip. His bulbous head bobbed, gently kissing her neck just below her chin. She felt the wet precum glaze her skin.