The Waitress Next Door Pt. 01

Freddy sat in his car staring up at the sign on the front of the restaurant. Peaks and Valleys. "Experience the tallest peaks and the tightest valleys."

"Gross," Freddy thought with shame, knowing he was about to walk in. He had never been to or never would have expected to go to a breastaurant like Hooters or The Tilted Kilt, but there were a lot of things he hadn't expected that happened in the past year.

He got married at 23 years old. That was expected at least. Victoria and he had been together for 8 years, since their freshman year of high school together. They had moved to the suburbs of a city he had never been to to be closer to her step-mom. Then they got divorced at 24 when Victoria fucked her new boss within two weeks of starting a new job.

Freddy let out a sigh. A 24 year old divorcee about to walk into a restaurant whose marketing strategy is big tits and tight asses.

"Were the asses supposed to be the valleys?" He thought to himself as he exited his car and walked through the front door. He was immediately hit by the smell of fried food and a pumping AC system. Freddy shivered, and couldn't tell if it was the stale smell or the cold air.

The next thing he was hit by was the sight of the girl standing behind the hostess stand. She couldn't have been older than 21. Straight black hair with bangs framed a cute face with an upturned nose. Her hair fell to the top of her chest, which was squeezed into a tight, white, tank top. Her tits weren't as big as the tagline of the restaurant would suggest, but the neckline of the shirt was deep enough to show ample cleavage. Her nipples were very visible poking through the thin fabric.

"That explains the AC." Freddy muttered to himself as he walked up to the girl.

"Welcome to Peaks and Valleys! Dining alone tonight?" She greeted him enthusiastically with a smile.

That's probably not the only time she's going to say that tonight. Freddy thought, but he tried to hide his embarrassment and sound casual in his response of "yep".

"Anywhere you'd like then! Your server will come around with a menu once you're seated."

"Thanks, Jenny." Freddy responded, taking the chance to look at her tits one last time and hide the glance behind reading her name tag.

He walked past the booths and took a seat at a high top with a good view of a tv behind the bar. It was 8 o'clock and a basketball game was on. Freddy didn't care much for basketball, but it was a decent, veiled excuse for coming somewhere like this alone.

He looked around at the other patrons of Peaks and Valleys. 95% were men. Most in groups of two or four laughing and putting back beer and staring at the servers swinging their hips in an obvious attempt at better tips. There were some single diners. Most at the bar, but some at tables. Freddy thought they all looked pretty sad eating alone, but he may have been projecting his own insecurity.

A pretty voice jolted him out of his thoughts and made him physically jump.

"Hiya! Here's a menu, can I start you off with something to drink?"

Freddy turned to look at his waitress and his heart leapt into his throat. She was absolutely gorgeous. Long wavy brown hair cascaded around a heart shaped face. You could tell the natural color was dark brown, but bleaching by the sun had added blonde highlights. Long eyelashes hung over piercing dark blue eyes, above a button nose, above full lips coated in subtle peach lipstick.

He felt like he was staring into her face for way too long, but it must have only been a moment because she continued speaking with no annoyance.

"You know most guys are entranced by us servers, not the other people eating here," She smiled.

Freddy smiled back and chuckled, "I can see why."

His face immediately fell. "Holy shit what a disgusting thing to say. Oh my god I'm so sorry, I don't mean to objectify you. I just mean you're very pretty."

The waitress laughed, "It's not a problem. I mean I'm the one that works at Peaks and Valleys. I'm kind of asking for it aren't I?"

"You absolutely are not asking for anything," Freddy continued. There was a pause as the waitress softly smiled in his direction and Freddy stared into her eyes back. "Uhhh, I'll just have whatever lager you guys have." He continued, as not to extend this painful experience longer than needed.

"One lager, you got it. My name is Callie, let me know if you have any questions." Callie smiled as she turned and headed to another table.

Freddy had been stunned by her face, but now he had time while she wasn't paying attention to him to take in the rest of her body. The natural blond highlights in her hair made him think of a beach volleyball player, and the rest of her body did the same.

The Peaks and Valleys tank top looked even better on Callie than the hostess, probably in part to the bigger tits under the plunging neckline. She had to have at least large C's if not D's compared to the small B's of the raven haired girl, but her nipples were similarly protruding. No bra must also be part of the uniform. Her breasts overhang a tight, athletic waist that couldn't have any fat on it. Her hips widened into an even tighter ass.

The bottoms of the uniform could barely be called shorts. Maybe this is where the thought of volleyball players entered into Freddy's mind, because the servers all wore small tight spandex that cut pretty close to the ass. A girl like Callie, who obviously did a lot of squats and had a round bubble butt, had trouble keeping the bottom of her ass cheeks from peaking under the booty shorts. And when she turned in his direction, Freddy saw a clear cameltoe between her long tanned legs.

Freddy had definitely been stunned by her beauty, but his heart had leapt because he knew this girl. Callie lived next door to him.

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She had moved in about two weeks ago, or at least that was when Freddy had first noticed her. He had been pretty depressed after Victoria moved out of their place three months ago, and Freddy didn't leave the house very much. One of the only perks of living in the suburbs is the size of the houses you can get, so there wasn't much he needed to leave for.

He worked from home (thanks Covid), ordered all of his groceries and meals (thanks doordash), and had some weights and workout equipment in the garage. He could move from his bedroom, to his office, to the gym, to the kitchen, and back to bed without having to step foot outside.

Freddy worked in sales and was pretty damn good at it, which meant he had not much oversight and a lot of down time. As long as he hit his numbers, his boss didn't care. That meant a lot of staring out the window during his work day. It was during one of these moments of day dreaming that he first saw Callie.

Freddy's office in his house was on the second floor, and the window looked straight into the backyard of his neighbors. Up until now, it had been a boring sight. A well manicured lawn with an unused hot tub right outside the back door.

Then one day about two weeks later, his interest in the neighbors yard skyrocketed. He noticed Callie, laying on a deck chair, in a bathing suit. Her body was glistening with a thin film of sweat in the sun. A small tan bikini barely covered her privates, but the color was so close to her tanned body that it didn't look like she was wearing anything at all.

She was wearing sunglasses and reading a book, unaware of her voyeur not 20 feet above her. Freddy stared for what felt like hours at this new seductress tanning outside. He didn't notice his erection until she flipped over and untied her top. Her bikini turned out to be a thong swimsuit and he had a full view of her essentially naked ass. She laid on her belly, and her tits spilled out the side of her, flattened against the deck chair.

Freddy had instinctively reached down to adjust himself when his sweatpants had felt tight, and felt his hand slip around his rock hard cock. He started jerking off vigorously for a couple of seconds before jumping up and running to grab his binoculars. He had to see if he could catch a glimpse of her nipples or pussy.

Unfortunately for Freddy, when he got back to his perch she was gone. He sat staring out the window until the sun started to set before he gave up on seeing her again that day.

That night he had wrestled with a lot of feelings. The creepiness of watching someone tanning outside his window, the absolute unparalleled levels of horniness of watching someone tanning outside his window (he hadn't been in the mood to even jerk off since Victoria had left, so this welcome bikini clad sight had been an opening of the floodgates), and the loneliness that he had been experiencing for the past three months.

Now that the outdoors was much more interesting to him, he found himself glancing out the window more and more. He wasn't sure if something had changed, or if he had never noticed it before, but the shades were drawn open in the window directly across from his office. He had a direct sight into the room, and specifically a full length mirror angled perfectly reflecting a neatly made bed.

Freddy's heart fluttered at the thought of what he could peek at through this window. Before he did any of that though, he had to ensure he was entirely concealed. He pulled his shades down all the way, except for a sliver at the bottom. He had to be laying almost completely flat on his desk to see through the gap. If he turned off the lights in the room (which he did), the way an awning shadowed his window there was no seeing inside it. Only out.

Freddy was lucky he had sprung to action, because his efforts were fruitful that very night. After work, he went to his garage gym and did his daily work out. He made himself a protein shake and took his seat back in his office. He looked out the window and waited.

There were many boring hours between his workout and 11:42, but his patience finally worked out. He saw a light flip on in the bedroom, and the slender legs of Callie walked into frame. She was wearing the same uniform he would admire her in at Peaks and Valleys.

This first time he saw it immediately hardened his cock under the desk. He pulled off his pants quickly and started massaging his head. Callie paused in front of the mirror, and Freddy looked into her piercing blue eyes as she looked at herself in the mirror.

His eyes fell down to her tits and he quickened his yanks as Callie pushed her tits together first with her biceps and then with her hands. He didn't know whether she was practicing her tip making strategies or what, but he was grateful for it regardless.

Whatever she was doing, it didn't last long, and she turned to walk out of frame. A gasp of excitement quickly changed to a grunt of disappointment as she began to take her top off, but was out of sight before Freddy could see anything.

He did see the tank top and spandex thrown onto the floor in front of the mirror. His mind danced with images of what she might look like naked, just a few feet out of sight. When she didn't return for a few minutes, Freddy booted up his computer and looked up where Peaks and Valleys was. There was only one in the whole city, only a ten minute drive from their neighborhood.

His search quickly led him to a subreddit of breastaurant employees in various stages of undress. He was distracted by one specific video of a pair of giant tits smothering a huge cock. The head of the dick was poking out through the cleavage as the headless server methodically worked her breasts up and down. The melons were constricted by a see through Hooters top that was eventually sullied by an outpouring of cum from the tip of the penis.

When Freddy had the ability to pull his eyes from his screen, he found the shades drawn and the light off across the street. He grumbled to himself before finishing himself off with the titty fucking video.

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Freddy watched Callie leave for work for the next few days out his front window. Every night he considered going to the restaurant himself. He finally convinced himself on the following Monday when he saw her heading out. Tonight was the night.

He hadn't planned to sit in her section. He just wanted to observe her from a distance, which is why he was so startled when she served him.

"Here's your beer, any food?" Callie's voice snapped him out of his daydream, thinking back to her ass cheeks displayed before him in her backyard, and her tits pressed together in her bedroom window.

"Uhhh yeah," He quickly opened the menu and ordered the first thing he saw. "Southwest Salad please."

"One Southwest comin' atcha," She smiled and slipped away. Her ass jiggled as she sauntered, and Freddy pushed his chair in closer to the table as his cock began to stiffen.

His erection didn't go down for the rest of the night. No matter where he looked, a low cut top or tight ass was there to keep him hard, and everytime Callie was in view he received another rush of blood to his dick.

He ended up drinking 4 beers and staying for three hours. Callie was friendly enough with idle chit chat and smiles, but Freddy wasn't naive enough to think anymore of it than a service industry worker.

The restaurant began to clear out as it got closer to the 11 o'clock closing time. Freddy paid and waited for Callie to be out of eyesight before he dipped away, hiding his boner the best he could.

When he got home, he stayed at the front window waiting for Callie to come back. She finally did around 11:35. It was a short walk from her car to her front door, and Freddy didn't blink as he watched her complete it. She looked exhausted from work, but her perky tits still bounced with vigor as she walked.

Once her front door closed, Freddy went straight to his voyeur's nest. Unfortunately, her shades were drawn, so he went straight to bed. He blasted two loads to the thought of titty fucking Callie in her tight white top. Her face and upper body took the place of the headless video in his mind's eye. His cock poked up the top of her cleavage and reigned cum onto her tits. Her piercing blue eyes stared into his soul, and her pretty peach lips sucked and lapped up the cum from herself. He didn't go soft until he fell asleep.

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Freddy saw Callie daily over the next couple of weeks. Mostly he caught glimpses of her in her bedroom. Waking up or going to bed and passing by in an oversized t-shirt and underwear. But sometimes he got lucky. Other times, he got really lucky

Spring was turning into summer, and as the temperature warmed up, she spent much more time outdoors.

Everytime she was laying out on her deck chair, Freddy had one hand on his binoculars and one hand wrapped around his hard cock. He could see every curve of her body. Her tits pressed together in her bikini. The mound of her pussy under the thin fabric of bottoms. On multiple occasions he could see the outline of her cunt.

The luckiest he got thus far was one Saturday afternoon a couple of weeks after their interaction at Peaks and Valleys. She was laying out in a small red bikini reading what must have been a particularly spicy novella. Freddy's binoculars were trained at her chest, and he noticed her breathing begin to speed up. Her left hand then came into view softly rubbing up and down her cleavage.

Her chest began to redden as her hand traveled slowly to complete circles around her right breast. Her nipples started poking through the fabric, and Freddy's grip on his cock tightened as she started pinching her nipple.

He watched as she let out a deep breath and put her book down as she continued to caress her breasts. She sat up slightly and started looking around coyishly. As her eyesight shot up to Freddy's window, he dove under his desk. The work he had done to conceal himself proved successful, however, as Callie didn't linger long on his window. From her view it was a window that had been closed since she moved in over a month ago. She must have been satisfied because she layed back down, and much to Freddy's delight slid a hand down to her pussy.

She rubbed up and down her slit over her bottoms while she continued to pinch her nipple. Her back arched and she let out a small gasp of breath as her fingers found the top of her swimsuit and slid underneath. Freddy held his breath with mouth agape as her legs spread and she started working circles around he assumed her clit.

Freddy's first glimpse of Callie's bare nipple came at this time, when she started grabbing her tits under her suit more aggressively. She was in a trance of ecstasy as she didn't even notice her bikini strap fall off her shoulder and her tit popped out as she kneaded and pulled on her breast.

Freddy didn't know where to look as Callie's right hand began fingering her cunt and her left hand shot from her boob to her forehead. He could see her fingers going in and out faster and faster, but that was still under her suit, leaving some to the imagination. Her arms position as her hand held her forehead had led to her other strap falling and both her tits were now fully exposed.

As hot as the vigorous fingering was. Freddy's eyes couldn't leave the upper torso of Callie. Her back arched, tits up and blushed with a pre-orgasm pink. He was about to cum himself when he heard an audible squeal come all the way up to his ears.

Callie's hand shot to her mouth as she writhed on the deck chair orgasming. Her hips bucked and she grasped her pussy and shook her head trying to hold in her squeals.

Freddy blew his load all over his hands and lap as he let out a gasp of ecstasy. Callie didn't know, but they had just cum in perfect sync and harmony.

Freddy sat in a pool of his own semen as he watched Callie's breath slow and her body relax. After five minutes of laying in the sun in bliss, Callie sat up undid her currently useless top, and walked topless back into the house. Freddy's cock hardened again as he watched her saunter to the door. Her thong swimsuit so far up her ass crack she looked completely naked. The swaying of her hips caused her tits to sway back and forth as he caught glimpses around her bare back.

After that experience, Freddy decided he had to talk to her again.

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He made his move one evening a couple of days later. Freddy's sleuthing had discovered Callie didn't work Mondays, so when it rolled around he took his seat in his nest. He was peeking through the window, hoping for a show, when his prayers were answered.

Callie walked into the window frame wearing nothing but a towel. She stood in front of her full length mirror and brushed her wet hair slowly. The rhythmic untangling of her wet strands of hair were some of the most seductive erotic movements she could do. That is until she undid her towel.

After brushing her hair, she threw the brush on a desk and let her towel fall to the floor. She was in a sultry mood, as she posed for herself in the mirror. Freddy's cock throbbed in his hand as he watched his own private show.

Callie started by covering herself with her hands in a Pudica pose. She squeezed herself in her arms and hands, allowing her tits to squish through her fingers. She then leaned forward slightly and blew herself a kiss as she struggled to hold her goods in. She spun around, looked over her shoulder at her ass and winked.

Freddy was losing his mind. It was his first full look at her pussy lips. It was a cute slit that he could see the beginnings of moisture around the lips. He didn't think he could get harder, as precum began to glisten on his head.

But then Callie sauntered to her bed. Through the perfect angle of her mirror, Freddy watched Callie lean to her bedside table, open the drawer, and pull out a huge purple vibrator. She spread her legs and started rubbing her clit.