The Waitress Next Door Pt. 02


As Freddy stood on Callie’s doorstep waiting for her to come to the door, he racked his brain trying to think of something to say. He had been watching her through his window for the past 6 months, and if he said the right thing here, he may be able to see her inside her house for the first time.

It’s not like they had never spoken. They were friendly in passing, and he had even interrupted a masterbation session of hers that he believed ended with an orgasm with him in her mind. He would have been fine continuing their relationship behind a pane of glass if he hadn’t seen her and her cute friend pointing up at his window and giggling in their bikinis.

That’s what took him to her doorstep, and luckily a lightbulb hit right as Callie answered the door. Even though he had been watching her all afternoon, he was still taken aback when she finally did come into view, as he always was when he saw her up close.

Her light brown hair flowed down to the top of her large perky chest, which was covered only by the bikini top. Her tits basically spilling out the sides and barely covering her hard nipples. She was wearing a white sarong wrap that was tied off and held by her hips just above her bikini bottoms. One strap was sticking out the top. She wasn’t wearing shoes. The all white outfit made his dick twitch.

“Hey, I — Oh I’m sorry, I don’t mean to disturb you if you’re swimming or something,” Freddy played dumb with a line he thought up while waiting at the door.

“Hey Freddy!” Callie responded, with, to Freddy’s delight, no level of annoyance or embarrassment. “Not disturbing at all, I wish I was swimming, but no, just tanning. I don’t have a pool.”

Freddy felt so smooth, slyly claiming he didn’t know what her backyard looked like, even though he knew in which direction every blade of grass grew. He continued the script he had worked out in his head.

“Is your wifi out? Mine just crapped out and I wasn’t sure if it was just me or the whole neighborhood or something.”

“Ummm hold on, let me check.” Callie turned and walked back inside leaving the door open a little bit. Freddy watched her hips sway and stared at the whale tail now visible out the top of her sarong. He adjusted his hardening dick into his waistband and tried to steady his ragged breath.

Callie came back out with her phone in her hand.

“I still have mine, must just be you. Sorry about that!” Callie said sympathetically.

“Damn, alright. Guess I’ll have to find a book or go to bed super early or something.” Freddy chuckled, hoping she would take the bait. To his delight, she did.

“Do you want to hang out here? I have a friend over, and we are just chilling.” Callie asked.

Freddy tried to hide his excitement.

“Are you sure? I don’t want to intrude if you have a guest.”

“Yeah no problem! Honestly, it would be nice to have a friendly face. She’s from work, and I don’t really know her that great. You’d be doing me a favor.” Callie smiled and opened the door wider for Freddy to enter.

Freddy smiled back and stepped inside. Callie’s house was almost exactly the same as his. They lived in a cookie cutter neighborhood, so it was no surprise. The furniture was much nicer though. Considering the age of her parents, that made sense.

“We are in the backyard.” Callie said, leading him to the back door. She stopped right outside so he was standing in the doorway. She was so close to him he could smell the floral shampoo she used in her beautiful hair.

“Jenny, this is my neighbor Freddy. His wifi is out so I invited him to come hang out.”

Jenny was laying on her stomach and lifted herself onto her elbows as Callie spoke. Her long black hair fell over her shoulders to the lounge chair framing her tits. Her elbows pushed them together and Freddy could see the outer coloring of an areola.

Over her shoulder her pale, round ass was eating her thong swimsuit. She smiled at him seductively under her bangs making his cock ache against his waistband.

“You’re young and cute,” she smirked. “What are you doing living in a neighborhood like this?”

Freddy smiled, mainly because his fear of her recognizing him from his excursion to Callie and Jenny’s restaurant Peaks and Valleys was clearly unsubstantiated.

“It’s a long story.” Freddy looked to his side at Callie who was looking up at him with a look in her eye that he couldn’t place. Like she had an idea or something.

“It’s getting cold, want to go inside? I can open a bottle of wine.” Callie asked looking from Jenny over her shoulder to Freddy.

“Oh yes please!” Jenny jumped up. “I’ll go get dressed real quick.”

She hurried past Callie and Freddy, and Freddy didn’t miss that when she squeezed past him in the doorway she brushed her ass against his arm. With how tiny her swimsuit was, the bare skin gave him goosebumps.

Callie led Freddy to the kitchen and grabbed a bottle of wine from the fridge. It was a large kitchen with a big island in the middle. The wine fridge was almanbahis on the side of the island facing the stove, and Freddy followed behind Callie with the fortunate result of watching her bend over. It was only for a moment, but her sarong fell to the side and Freddy got an eyeful of ass in front of him. Her bikini bottoms were being eaten by her globes, and he could see the outer lips of her pussy.

The moment was gone, but led to another sexy moment of her opening the wine. Her tits jiggled as she spun the corkscrew and popped out the cork. Freddy was rock solid at this point, so he turned his waste into the island to hide what he assumed was his obvious boner.

Callie had just handed Freddy a glass when Jenny came down the stairs. He was glad he had hid his erection, because Jenny was wearing her work uniform in its entirety. Skin tight deep necked white tank top, tight booty shorts that were essentially underwear the way the girls’ asses hung out, no bra, no underwear. Freddy accidentally let out an audible gasp to the joy of Jenny. She giggled as she put her hands behind her back, pushed out her chest, and rocked back and forth on the balls of her feet.

“It’s all I have, I came from work,” she explained while rolling her eyes and acting annoyed.

Callie also took note of Freddy’s reaction and announced she would go change as well as she handed Jenny a glass of wine. Freddy heard her whisper “whore” with a smile in Jenny’s ear as she passed by, which made Jenny giggle even more.

Jenny leaned her elbows on the island presenting him with her cleavage. She kept her legs straight so her ass was sticking straight out behind. Freddy gulped as he realized he was either being seduced, or messed with. He prayed for seduction.

“So, Freddy,” she said, emphasizing his name. “Tell me this long story about how you ended up in a neighborhood like this. When Callie invited me over I never would have suspected someone like you walking through the door.”

“I’ll save you the gorey details. I got married young, we wanted to settle down, then she cheated on me, so we got divorced, and I got the house.” Freddy shrugged. “A tale as old as time really.”

“A divorcée huh. That’s unexpected. When did all this happen?” Jenny continued in a serious tone. A rare situation Freddy found himself in, speaking with a smoking hot breastaurant waitress, falling out of her skin tight clothes in a serious manner about his divorce.

“Oh I dunno,” he answered. “Like 8 months ago?

“Ah…” Jenny paused for a moment before continuing. “Fucked anyone else yet.”

Freddy almost spit out the sip of wine he had just taken.

“What?” He managed to get out.

“Your wife cheated on you. Have you fucked anyone else? Like to rebound or revenge or something.” She wasn’t smiling or giggling or anything. She seemed perfectly serious and interested.

“No, no. I haven’t,” Freddy answered truthfully. “Honestly I haven’t really put myself out there though.”

“You haven’t really put yourself out there,” Jenny repeated to him. This had elicited a smile out of her. “Interesting.” She continued to herself.

“What’s interesting?” Callie interrupted from behind Jenny.

Freddy actually did spit out his sip of wine this time. Callie was wearing a see through white crop top with a black lace bra underneath. Her abs were exposed above a really short red plaid schoolgirl skirt that came to mid thigh. Her wavy brown hair had been quickly curled and fell beautifully to her shoulders.

“Well first off, THAT is an interesting choice.” Jenny laughed as she turned around and leaned back against the island. If Freddy had looked he could have seen straight down her top, but he was way too distracted by Callie.

“Fuck off,” she laughed in response to not come off as actually upset. “I never have guests or see anyone outside of work. I wanted to get cute.”

You didn’t get cute, you somehow got even hotter than you usually are, Freddy thought to himself.

“I was saying that it’s interesting that Freddy hasn’t fucked anyone in 8 months. Wouldn’t you agree?” Jenny teased.

Callie cocked her head and smiled as Freddy fidgeted in discomfort.

“That is interesting.” She softly said to herself.

“Come on,” she started louder again. “Let’s go to the living room, Freddy grab the wine.”

Jenny jumped off the island and skipped forward a step to Callie and they walked towards the living room. Freddy’s mouth was agape as he walked a few steps behind them. Both of their hips swayed in unison and Freddy couldn’t keep his eyes off their asses. Jenny’s biker shorts were in a wedgie up her ass crack showing everything, and Callie’s skirt bounced up and down revealing more of her upper thighs.

These two smoking hot waitresses were definitely flaunting themselves to him, and he couldn’t control himself. Freddy stole a little rub of his cock as he followed them to the living room.


Callie and Jenny sat next to each other on the almanbahis giriş couch, and that left an armchair for Freddy. The room was set up so the couch and armchair faced each other with a coffee table dividing them. Freddy took his seat and looked across the coffee table at the two beauties sitting in front of him.

Neither relaxed into the couch. Both were sitting at the edge of the couch with straight backs and their hands in their laps. The position pushed their tits out and squeezed them together. Freddy gulped loudly as he took in the sight, adjusted himself uncomfortable and crossed his legs to hide his boner.

Smiles hinted at the corner of the girls’ mouths making Freddy think they knew what he was thinking. He knew there was no way it wasn’t written all over himself.

“Sorry I don’t have a TV down here,” Callie started. “I don’t have many guests and I don’t really hang out in this room.

“I don’t mind at all, I’m all for riveting conversation.” Freddy responded with a smile. “How long have y’all been friends?”

“Oh I don’t know, when did you start working at Peaks? 6 months ago? Took about three before we started talking?” Jenny answered, looking at Callie.

“That sounds right.” Callie responded.

There was a pause. The tension was palpable. Freddy couldn’t tell if it was sexual tension or awkwardness, and he didn’t want to tempt fate, so he continued with what he thought was casual conversation.

“What’s it like working there?” He asked. “Do you get… like… objectified a lot.”

“Oh yeah sure. Most of the customers are gross old men that say stupid shit. But you don’t take that job if you aren’t confident or have thick skin.” Jenny answered candidly. “Plus it’s hard not to look hot as fuck in these uniforms. Don’t you think so?”

She stood up and turned around showing Freddy her tight ass and gave him a wink over her shoulder. Freddy turned red and took a large gulp of wine finishing off his glass. He went to pour himself more as Jenny sat back onto the couch and laid back with a giggle. She left her legs spread open a little, giving Freddy a full view of her camel toe.

Freddy noticed Callie shoot Jenny a look and Jenny raised her eyebrows back. Callie downed the rest of her wine.

“Good idea,” she chirped as she stood up and grabbed the bottle of wine from Freddy.

She placed her glass on the table and leaned over to fill it up. She kept her legs straight and bent into a full 90 degree angle. Her tits practically spilled out of her top a foot away from Freddy’s face. She then spun and bent over pouring the rest of the bottle in Jenny’s glass. She again dropped to the 90 degree angle, causing her skirt to ride up high on her thighs. The hem came halfway down her ass, so Freddy had a full view of the rounded bottom of her cheeks. He didn’t see any underwear

She stayed in that position a couple seconds longer than needed, and must have made a face at Jenny, because it elicited a tongue stuck out in Callie’s direction. These girls were playing a game at Freddy’s expense and he was all for it.

“I’ll grab another bottle! Drink up.” Callie sang as she skipped away into the kitchen.

Freddy watched her all the way until she was out of sight. When he looked back at Jenny he jumped. She was sitting at the edge of the couch with her legs spread apart and her hands on her knees. She was leaning forward with her shoulders back presenting her chest to him. The fabric of her tank top was stretched thin over her rock hard nipples.One eyebrow was raised to her bangs and she had a sultry smile on her face.

“Freddy, I can see your erection.” She quietly purred.

Freddy spit wine onto the coffee table and instinctively shot a hand to his crotch to cover any bulge. Jenny laughed and leaned back into the couch. She pulled lipstick out of god knows where and started applying it very seductively.

Freddy grabbed some napkins off a small table next to his chair and started wiping up the wine.

“What happened?” Callie asked innocently as she came back into the room.

“I, uh, spilled some, uh wine on the table.” Freddy forced out while Jenny giggled to herself.

“Oh no problem!” Callie chirped up. “Let’s just move this table anyway. I wanna play a game.”

Freddy helped Callie push the table to the side, while attempting to hide his boner as much as possible. Once moved he sat back down and crossed his legs again. Callie poured everyone another glass and placed the empty bottle of wine in the middle of them.

“Spin the bottle? With three people?” Jenny asked, seemingly not against the idea, just curious.

“No! How old are we?” Callie chuckled. “Truth or dare.”

“Is that much better?” Freddy laughed.

Callie pouted in his direction. “What you don’t want to play?”

“Truth or dare with two beautiful young women? I’m definitely in.” Freddy said emphatically, immediately turning red realizing what he said. The wine was definitely doing what it was supposed to do.

Much almanbahis yeni giriş to Freddy’s delight, both girls beamed at him.

“Callie you’re idea, you go first.” Freddy continued quickly.

“OK!” She chirped. Staying in her seat she leaned over to spin the bottle, her tits pressed against her knees making Freddy very excited for this game.

The bottle spun and landed on Freddy.

“Freddy, truth or dare?” Callie asked.

“Truth.” He said, wanting to start off playing it safe.

“Are you currently in a relationship?” Callie asked, to the eyeroll of Jenny.

“I am not in a relationship.” Freddy answered truthfully. He then spun the bottle and it landed on Jenny. She also said truth, and Freddy asked the same question.

“Oh my god how boring. No, I am not in a relationship and neither is Callie. Better question.” Jenny said annoyed, refusing to spin the bottle again.

“OK, uhhhhhh. What is a hidden talent?” Freddy asked, trying to be uncontroversial. Jenny definitely knew where she wanted the night to go, however, and controversy was the name of the game.

“I can deepthroat a cock better than anyone who’s ever touched lips to your dick.” She said casually. She followed up her answer with a wink at Freddy and an eye raise at Callie.

Freddy turned bright red and squeezed his legs tighter together. Callie also turned red, but it seemed more out of annoyance than embarrassment.

Jenny spun the bottle and it landed back on Freddy. He responded with ‘truth’ again.

“How big is your cock?” She asked quickly and confidently, continuing down her path of uncomfortable truths.

Freddy somehow turned an even brighter shade of red and looked at Callie. She was also blushing, but looking at him intently.

“Oh I don’t know. I’ve never measured.” Freddy deflected.

“Buuuulllshit,” Jenny called out. “Every guy measures their cocks.”

“Sure but when they are teenagers, I haven’t in a while.” Freddy continued to deflect.

“If you can’t answer the question you have to do a dare.” Jenny and Freddy both looked at Callie for support. Callie paused a moment before nodding in alignment with Jenny.

“Fine, dare then I guess, but I really don’t know.” Freddy said dismissively.

“I dare you to show me your cock.” Jenny said with a smirk, having won.

Freddy was beaten. He looked back and forth between the two girls who had both leaned forward instinctively to get a better look.

Freddy sighed and responded with a compromise.

“You know what, I think we can all see where this is going. I will show you my cock, but I want a verbal consent from everyone that if we start to get uncomfortable, we will stop it.

“I consent, now show us your cock.” Jenny called out with a smile. Callie also consented.

“Ok.” Freddy slowly stood up. “In a way to keep this game moving at a manageable pace, I will show you the OUTLINE of my cock.”

It was Callie that called out this time, “Buuuullshit.”

“No no, I’ll allow it. I appreciate a man who can take his time.” Jenny agreed, leaning back into the couch. Callie pouted but looked on.

Thankfully Freddy was diamond hard, so his cock was as big as it would ever be. He grabbed the leg of his jeans and pulled it taught, creating a bulge down his leg the length of his dick. Both girls’ eyes went big and they leaned forward.

“Holy fuck it’s huge…” Jenny whispered no longer cocky.

Freddy had been willing to play along with this game because he was very well endowed. When his wife used to suck him off she would use both hands and still fit more than the head in her mouth. Freddy stood definitely in front of the girls that were entranced by the outline.

“It has to be 10 inches,” Callie said softly, eliciting a nod from Jenny.

Freddy knocked them out of their trance by sitting down and depriving them of the sight. He was imbued with a new sense of confidence. He spun the bottle and it landed on Callie.

“Truth,” she said, not ready to make the leap quite yet.

Freddy paused to think before asking, “Did looking at my cock just then make you wet?”

Callie was already flushed, but that question made her squirm a little in her seat.

“A little,” she said with a coy smile, letting everyone know that her pussy was way more than a little wet. Her hand dropped into her lap and pressed down a little bit before shooting up to put her hair behind her ears when she realized what she was doing.

The bottle spun to Jenny who confidently exclaimed “Dare!”

“Masterbate.” Callie confidently retorted.

It was Freddy’s turn to go wide-eyed as he watched Jenny shoot Callie a confident smile and lean back into the couch.

“So much for taking our time,” Jenny said as she slid her right hand down her spandex and started rubbing her clit.

She softly moaned as she rubbed her fingers in small circles. Her eyes were locked on Freddy’s with her mouth open as she breathed heavily and gyrated her ass on the couch in rhythm with her fingers.

Freddy couldn’t help but slowly rub his cock through his jeans without breaking eye contact. Jenny smiled at that and lifted her left hand to her right tit. She started pinching her nipple through the fabric while oohing and ahhing.

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