STORY - The Stay-At-Home Boss (Patreon)

Hey, folks! It's been a quiet month on the patreon, but a very productive month behind the scenes. With several things being worked on, I haven't had time to do much editing - and with Luffy316 being the ace he is, we have several stories on the grill waiting to be sent out. So! Rather than keep you all waiting, I'll be kicking myself off the editing board for a bit and sending these stories out as soon as they're done. First up, we have another winner of our last poll - The Stay-At-Home Boss! Enjoy!

------

The evening lull at Pizza Thot was always the easiest part of the shift. It was too late for lunch and too early for dinner, and nobody but the horniest of customers would come for the T&A. The staff took the time to restock and refresh whatever they needed, but it always led to smalltalk to make the work go faster. It was where the various Thots caught up with each other and vented their various woes. In this case the woes were Boss'.

"So between the hole in the roof of the apartment building, the work on the foundation, the busted elevator, spraying for ants... well, they say the whole building's gonna be closed for about a week as of tomorrow," Boss explained. She was seated at one of the empty tables, sorting over some receipts.

"Tragic news, my girl," Chadsworth tutted as he helped Pineapple sweep up. "Whatever will you do?"

"I don't exactly have another place. I was thinking I could hide out in a motel for a while. Maybe put Mortimer in a kennel if they don't allow cats. He'd hate it, but he's always in a mood anyway."

"Oh nonsense!" Chad insisted, dropping his broom to throw out his arms. "You're always welcome in the casa de Chadsworth!"

Boss did her best to hide a frown. Chad was her best friend for years now, but she always did her best to avoid spending the night at his house. Chad lived with his boyfriend and their walls were definitely not soundproof. Boss had barely slept a wink with all the moaning.

"Oh I couldn't put that on you, Chad. How about you take care of Morty for me? At least he tolerates you."

"I would be glad to be of service," Chad assured. "I will treat him as my very own."

"Cool. I can drop him off with you tonight after work. At least I don't have to worry about him at the motel."

"Hey, Boss! Why don't you just stay with me!?" Tips jumped out from the kitchen entrance with a pointed grin on her freckled face. Boss winced at the suggestion. If Chad was perverted enough to keep her up at night, then she hated to imagine what living with Tips would be like.

"Mmmaybe not?" Boss answered carefully. "I'll have to see what's available before I settle on that."

"Well there's always room at my place," Pineapple offered. "I've only got the one bed but the couch folds out."

Now THAT caught Boss' attention. Once you got past Pine's ridiculous package and general shyness, he was a perfectly sweet guy. He was also probably the least perverted of her coworkers who owned his own apartment. "You know that does sound pretty tempting," Boss admitted. "And I've never actually been to your place before." She shrugged, unable to find any good reason to turn down the hospitality. "You know what? Sounds good. I can pack my stuff and meet you after work tomorrow."

"Yayyy. Sleepover!" Pineapple chimed happily.

Everything went according to plan from there. Boss wrangled her cat into carrier and dropped him off with Chad before packing everything she'd need for the week. A short day at work later, she was walking into Pineapple's apartment. Pineapple hefted one of her suitcases onto a comfy little loveseat with a soft grunt of effort. His apartment was fairly roomy, looking about as big as Boss' place. It had some soft carpeting and all the furniture seemed to be selected to be as comforting and inviting as possible. A few cute toys or collectables rested on shelves or end tables.

"Make yourself at home, Boss," Pineapple said brightly.

"You don't have to keep calling me Boss, you know. We're not at work," she reminded him as she started to sort through her things for some old clothes to sleep in. They had both worked a late shift and they both had the same idea: a quick snack, brush their teeth and head to bed.

"Oh right! It's a force of habit by now. I see you at the Thot more than anywhere else so it's kind of a reflex."

"Well, y'know... that place won't run itself."

"Just glad to be part of the team," Pineapple said brightly as he peeled off his shirt. Boss politely averted her eyes as she started to change out of her shorts. They were coworkers in a job that involved a lot of tomato sauce and semen, so showers and a changing room full of spare uniforms was a necessity. Between that and keeping the customers happy, Boss had seen him naked plenty of times. It was still a little stunning every time he whipped out his dick, the happy and slightly absent-minded boy was blessed/cursed with a tool that was just over a foot long (Tips had been all too eager to measure for herself). If his soft bubble butt and cute face didn't win people over, his plump horse cock would do the trick.

She finally tore her eyes away long enough for them to finish getting dressed. They boiled up some noodles and called it a night. Pine helped her unfold the couch into a bed and dug out a fuzzy pink blankets and pillows (though Boss declined a nightlight). They said goodnight and hit the lights as Pineapple went off to his room.

It wasn't the most comfortable thing in the world, but it did the trick. It had been another busy day, so Boss fiddled with her phone for a while until she dozed off. She slept soundly for a couple of hours until she was woken up by the sound of a door. When she glanced up, she saw it was just Pine getting up to use the bathroom. He was dressed in nothing but some pink shorts, and he looked even more out of it than usual in his sleepy state. Boss shrugged it off and curled back into her blanket, thinking nothing of it... until Pineapple climbed into bed with her. The feeling of her employee's huge, rock hard erection against her ass woke Boss right up.

"Uhh... Pine? Whatcha doing, buddy?" Boss asked warily, giving him the benefit of a doubt. She could feel the head of his massive prick poking against her back where her shorts didn't quite cover.

"I'm goin' ta bed," Pineapple mumbled in her ear, tossing an arm over her. "Jus' need a new teddy bear..."

"Pine, I'm trying to sleep," Boss sighed. "I don't have time for this."

"But the president's going to be in tomorrow, teddy..." Pine mumbled as he squeezed her tighter.

"Great. Pine's a sleepwalker," Boss grumbled. He shifted his position to get more comfortable behind her. It rested his hefty shaft right between Boss' ass cheeks, something that made the shorter woman shiver. She'd never slept with Pineapple, unless you counted teaming up for some very intimate strip teases and lapdances. People still adored him for various reasons, but she didn't see a dick that huge all the time and not wonder about it.

"Pine," she repeated, trying to get through to him with her commanding work voice. "You've got five seconds to wake up or I'm going OHHHH WOW! That's happening!"

Pineapple had wiggled around and rearrange Boss and himself until his massive cock pushed between her thick thighs. It rubbed the thick head of his shaft right along Boss' crotch. Boss got over her initial shock of having something so huge between her legs fairly quickly, starting to relax into Pineapple's warm and unwitting cuddlefuck session.

"I mean... as long as I'm already awake," Boss muttered. Pineapple's warm breath blew over her neck as he started to moan, humping her thighs with some semblance of rhythm in his sleepwalking wet dream. Getting a little excited herself, Boss figured it was easier to cooperate than just let him have his sleepy way with her. She let Pine keep up his hug as she started to wiggle her way out of her shorts. The grinding of her ass against the rest of his erection made him moan into her ear as she awkwardly stripped out of her bottoms.

"Okay, fine," she muttered. "But you owe me." She grunted and twisted around a little to pull down his briefs, letting his erection spring eagerly out of his underwear. It slapped against her ass hard enough to make Boss wince and shake her head.

"Oh no you don't. We're not getting that crazy that fast." She managed to reposition herself where his cockhead found her pussy instead. Pineapple let out a happy little sigh and rolled his hips to finally push his way inside her. Between his clingy hug around her and the sheer size of him, Boss felt most of her body slide slightly higher on the foldout bed. Boss hissed through her teeth as the fat shaft pushed its way into the smaller woman, but once it was firmly pulsing inside her she immediately relaxed and leaned into it. Her thick booty bounced against his stomach as Pineapple thrust between her legs, fitting as much as he could inside Boss' tight pussy. Even if he couldn't get it all inside her as once, he certainly wasn't complaining about the snug-fitting snatch. He hugged her tighter and moaned louder as Boss braced herself to take one of the biggest cocks she’d ever seen.

“You’re a good teddy...” Pineapple panted dreamily, his voice growing higher as he humped faster. His thick ass bounced behind him while his balls rubbed between Boss’s thighs, keeping him plenty satisfied. Boss was starting to find her own pace, sliding her hips up just before his thrusts so that she teased him with her pussy, just to be pumped even harder when his cock slammed to a stop against her clit. Her whole body tingled every time his giant member filled her to the brim and then some, sending shivers up her spine. Her body started to pulse and clench, their fucking starting to generate a thick squelching noise thanks to the mix of precum and pussy juice formed by their mutual arousal. Boss shut her eyes and let out a short, high-pitched cry as orgasmed, burying her fingers into the blankets. She didn’t bother holding back her shaking or loud grunts, figuring that if Pineapple wasn’t going to respond to his name or being inside of her, then he wouldn’t mind some sex noises. 

It certainly didn’t stop Pine from cumming inside her. His thick and creamy load flooded her with a steady stream of jizz, making Boss keep wincing as she bit her lip and held even tighter onto the blanket. She’d seen Pine cum with a few customers and he always had plenty to go around. It was the first time she felt the hot seed dumping out inside her, and it was a lot to take in. She finally let out a shaky breath, relaxing as Pineapple’s heavy breathing turned into high and soft sighs of relief.

“Wow, okay,” Boss shuddered. “That was… somethin’ else.” She shook from another little aftershock of an orgasm as she felt Pineapple finally pull himself back out.

“You did super good, teddy,” Pineapple sighed happily. He finally let go of Boss to roll onto his back.

“Yea, that was fun,” Boss admitted to the sleepfucking coworker. “You wanna go clean up, Pine?”

“Sure thing, angry teddy.” Pine clumsily got to his feet and returned to the bathroom. Boss slid out of bed to swap out her panties, watching Pine as he drunkenly stumbled back to bed. Content that he was back in his own bed, she flopped back into her blankets and fell right asleep.

“Sorry for being a burden on ya, Pine.” Boss was up early, packing her things back into her suitcase. “But I should probably find somewhere else to sleep tonight."

"Aww you weren't a burden, Boss." Even Pineapple's shrug made his bulge shift around. "It's not like you kept me awake or anything."

Boss held her tongue. She wasn’t angry at Pineapple; it was one of the bigger orgasms she’d had in recent years. On the other hand, she did have work to be done. She wouldn't be able to keep up her busy schedule with a sleepy cuddlefuck going on every night (no matter how fun they were).

"No, you were huge... I mean, great, Pine," Boss insisted as she zipped up her bag. "But I'll see you at the Thot tomorrow, okay?"

"Oh! Sure thing!" Pineapple gave Boss a big hug. It mashed his soft but still huge member against Boss' chest. "We should hang out like this more often."

"Yea, maybe then you'll learn to stop calling me Boss." Boss shooed away any urges for another quickie and made her way back to work. She spared the crew the details but she was back to the same problem as yesterday.

"You could stay at my place!" Tips offered again. "I'm so big you'd take up no space at all! Gyahaha!"

"Thanks, Tips," Boss grumbled with glare.

"I mean... she's kind of got a point." Cash cut in, getting Boss to aim her scowl at her instead. Cash just popped her gum indifferently. "How much space do you actually need?"

"Well... I'd be living out of my suitcase. Just somewhere to sleep and keep my bags, really."

Cash shrugged. "You willing to pay a little rent?"

Boss started to see through her offer. "How about twenty bucks to let me stay at your place?"

"Sounds great," Cash quickly agreed.

"I'll pay thirty!" Tips pitched in.

"What!? Are you even looking for a place to stay?" Boss snapped.

"No, but I just want in on the sleepover."

Cash grinned back at Boss. "Only room for two, and that's the best offer I've had all day," she said in a teasing voice.

"Fine. Forty for the week," Boss begrudgingly agreed.

"Sold," Cash mused with a casual point towards Boss. "Room 212 at the Hawkins Dorms. I'll buzz you in after work."

Tips pouted for a moment before happily going back to work. Boss had dropped out of college to run the business, so it wasn't the first time she'd had to stay in a dorm. They were small and basic, but it would do the trick for a short visit.

Boss stepped out a little earlier that day to head home with Cash. Cash's dorm room was everything Boss had expected: small and decorated with lots of black. She had some posters of trendy metal bands taped to the walls and a small cork board with pinned up tickets  concerts, shows and events she'd attended. The room was dimly lit, carefully by a setup of several smaller mood lighting rather than actually hitting the light switch. The trendy goth's style clearly outweighed her sense of practicality.

"Go ahead and settle in wherever. Front desk knows me, so you can borrow my badge if you need to step out. You can take the bed or the futon, whatever's easier." Cash went to the desk where she kept her laptop and a small plastic bin. She opened the case to reveal an impressive stock of gum and cigarettes, grabbing a pack of each and stuffing them into her pockets. It certainly seemed to go with her oral fixation.

"Take and eat whatever you want, long as you can replace it later. Milk lives on the next floor up if you need anything, but I gotta go get to class. I'm just gonna wash up and head out. See ya tonight."

It was as easy as that. Cash was out for most of the evening between classes and hanging with her friends. Boss caught up on some bills and got some dinner; she hadn't been out of college for that long, but she decided she'd feel old if she went to the cafeteria. Even with the dark emo look, it was a cozy little place once she realized Cash was a social creature. She was probably leaning on a wall somewhere around campus, smoking with her other edgy friends.

Cash came back around seven o'clock with a pair of portable cooler slung over each shoulder. "Hey, Boss. Got a party coming over."

Boss looked around the confined space she's spent the day in. "You sure about that?"

Cash just set down the coolers and unzipped one of them. Boss peered around her waist to see them stuffed full of ice and beer. "Yup. A few of the guys are coming over. And Milk. You know Milk, right?" Cash asked with a cheeky smirk.

"Yes, I know Milk," Boss said curtly. "Do you need me to clean up or get out or anything?"

"Nah and nah. The more the merrier, and I don't want it to look too tryhard in here. Real casual, you know? Got to act natural."

"Natural," Boss repeated with a slow and suspicious nod. "When were you going to tell me about this party when I paid you to stay at your place?"

"Like... right now." Cash shrugged. "I only started planning this thing an hour ago."

Within the hour, Cash's small dorm room was packed with black-clad bodies. People sat on the futon, the desk, the floor, or whatever else they could fit their asses on. Everyone was drinking and laughing while loud music played over Cash's laptop. Boss had found a spot on the bed next to Milkbar, each of them nursing a bottle of hard cider and a bowl of chips. They passed their time being awkward with each other while Cash did all the actual mingling.

"Oh my god, Drake. That's so fucking cool!" Cash praised as she clung to one of her guests. She had been talking to a tall guy in a black coat and a stylishly torn shirt and jeans. She ran her hand over his muscular forearm, tracing her fingers across his freshly healed tattoo of some kind of monstrous black bird. Drake smirked and took a swig of beer with his free hand.

"Yea, the guy does great work. He's a little ways downtown. A place called Dragon Ink."

"For real though," Cash gushed in a way that Boss had never seen her bother to use on customers. It was becoming more and more clear to her why she threw the impromptu party. "I've been thinking of getting another one myself. I already got the one..."

Cash conspicuously pulled down on her top, exposing the heart tattoo on her chest just at the edge of her black bra. She took Drake's hand and pressed it against the tat, making him cup her breast in the process. The drunken coeds locked eyes with their hands all over each other, too buzzed to think about much else until they mashed their lips together.

"I've never seen her lay it on that thick," Boss muttered to Milkbar. At least with their music, they weren't easy to overhear.

"Oh yea. She likes the cool bad boy types," Milk said as if she'd seen it all before, taking another casual sip of cider. Cash always remembered to get her favorite brand.

Cash and Drake started making out more heavily, the gothy Thot wrapped her arms around the taller guy's neck. She pulled down on a handful of his dark hair, forcing him to kiss her even harder. Even with the thumping music filling the room she was pressed hard enough against him that they could feel each other's deep moans and grunts. His hand slid underneath her shirt and around her bra to squeeze her bare breast, making the slender girl shiver. Cash pressed her hips against his jeans and couldn't help but start grinding against his bulge.

"Maybe we should move," Boss suggested as Drake started to lean into her, guiding Cash towards the bed. She and Milk scooted over just in time to avoid them dropping onto the bed, the occasional party goer hooting or whistling at the lusty display. Cash wrapped her legs around his to hold him against her, her painted eyes shut tight as she savored the drunken makeout session. While one of his hands busied itself under her shirt, the other had slid down Cash's pants. Cash gasped softly as his fingers found his way inside her, probing around her damp pussy until he brushed against the small piercing.

"Nice," Drake muttered to her softly as he parted his lips from hers.

"Glad you like it," Cash replied. It was one of the few times Boss could remember seeing the pale girl blush. She let out a sharp gasp and arched her back as Drake pressed two of his fingers deeper into her.

"Yea, you know what? I'm kind of partied out," Boss decided as she hopped off the bed. With all the loud company, she clearly wasn't going to bed anytime soon. "How about you Milk? Feel like turning in?"

The shy girl nodded and polished off her cider with one big gulp. The two excused themselves, figuring that the loudly moaning Cash wouldn't mind if they didn't say goodbye. Even on the third floor, they could hear the faintest thumping of Cash's party music.

Milkbar's room was much more simply done. A large bed, nice little TV, and a few photos (digital or physical) were about as decorative as the room got. A bunch of thick fluffy pillows were piled up on one end of the bed, a few snacks and a small container of meds on the headboard.

"Sorry if it's a little last minute," Boss apologized, setting down the smaller of her suitcases she'd pulled out from under a seated goth.

"Oh no! It's totally fine!" Milk insisted. "It's not big deal at all! Honest!"

"Alright, alright. I'm just saying thanks," Boss assured her as she looked around the room. There was no sign of another bed or even a couch. Milk clearly didn't expect to throw as many parties as Cash. It still meant they'd sharing a bed, but at least she could sleep in peace and quiet.

Thankfully, Milk seemed to respect Boss' personal space as best she could. Milk curled up into a surprisingly small shape to give Boss more room, but there was the inevitably bumping together of their curvy hips. They ignored it as best they could and soon Boss was yawning and dozing off.

Boss woke in the middle of the night to something soft and squishy being pressed across her face. The sound of Milk snoring slightly above her head told her everything; the big girl had rolled over in her sleep and buried Boss' head in her tits. Her loose tank top left some of the warm, dark skin exposed to press against Boss' cheek. She blinked up at the eclipsing set of tits that threatened to swallow up her entire head.

"Well... some part of me knew I would die like this," Boss admitted. She grunted and shoved at Milk's rack, but their difference in size was ridiculous. It was lightest of the Thots trying to get out from under the heaviest, so Milk didn't even stir from her sleep.

"Milk!" Boss whispered harshly. Her words came out muffled from being buried in Milk's massive udders. "Milk!" she tried a little louder. "Get up! You're crushing me!" When that didn't work, Boss tried to wriggle her way out. When that failed, she tried poking and then pinching at Milk's belly. While Pineapple had been a sleepwalker, Milk just slept like a log. There didn't seem to be anything she could do to make the bigger girl move. She was certainly one of the less mobile of her employees, unless you counted all the bouncing and jiggling she did in a customer's face.

That thought got Boss to pause. It had worked on Pineapple...

Boss couldn't escape, but she could shift her face underneath Milkbar's smothering boobs. She put herself right under the snoring girl's nipple and started to nuzzle up against it. It was no secret that Milk's breasts were incredibly sensitive, and soon her snorting started to turn into a soft cooing sound. Milk's chubby thighs rubbed together eagerly as Boss felt her starting to shift. It was humiliating, but it was actually working.

Boss managed to tug on Milk's top until enough of her big round breast popped right out, the erect nipple ready and waiting for more of Boss' attention. She started groping the other one while popped the other into her mouth, fondling and suckling Milk like her life depended on it. Milk's soft warm breath blew against her hair as she felt her tightening up, the inevitable sweet flavor hitting Boss' tongue. Between her meds and overstimulation, Milk was not only famous around the restaurant for her big figure but her naturally lactating tits. Boss sucked down a big mouthful while she felt some more trickling past her talented fingers, nosily milking Milk as she took a quick gulp to get back to work.

Milkbar's panting turned into soft mewls, clearly growing more excited. Her legs kept rubbing together and her breasts wobbled against Boss' face. The rippling flesh gave Boss some time to catch some fresh air before plopping back on top of her. Boss even pinched down on Milk's nipple with her teeth, getting a firmer squirt of milk from the cooing cowgirl. Boss tried to reach down with her free hand to grope at Milk's pussy, only to find her hand coming up short and rubbing over her soft belly.

She was starting to wonder if she was going to be stuck there for the night when Milk's moans suddenly turned into loud and passionate cries. Her body bucked as her pushed her breasts into Boss' face over and over, practically fucking the manager's mouth with her hard nipple. Boss grunted in surprise but kept her lips locked around her teat, surprised at her success when Milk quivered against her with a long, low moan. There was a familiar dampness against Boss' thigh as Milk flopped back to the other side of the bed.

Boss boosted herself up to catch her breath, staring down at the wet patch in Milkbar's panties. Apparently she had cum from Boss doing nothing but playing with her breasts. "Wow... learn something new every day," Boss mused. Milkbar still didn't wake up, but she did shift a little closer to Boss. She wearily slung an arm around her, cuddling her short manager against her chest. Boss sighed and took one of the plush pillows, tucking it between their stomachs as a simple wedge in case it happened again.

"You're lucky you're a good cuddler," Boss grumbled as she rested her head on Milk's plump breasts. Somehow they were even more comfortable than the whole pile of pillows.

"This is so super awesome!" Tips gushed as she threw open the door to her apartment. "I'm real glad you finally took me up on my offer."

"Well it's either this or I deal with sleepwalking, late night parties, or getting titsmothered in my sleep," Boss admitted as she followed her in, dragging her suitcases behind her. She had finally resorted to taking up Tips on her offer, already prepared for the worst. "Just don't make me regret it."

"Gyahaha! What's to regret!? I finally get a roommate!" Tips gestured around the room, and Boss had to admit it was the biggest apartment she'd been to all week. It was a little messy, but not the worst she'd ever seen. Bras, makeup and spare wires were left randomly around the apartment, but at least she didn't have any dishes or food laying around. She had some odd little collectables around, though none of any particular sort. There was a strange little statuette on one shelf with a little toy mecha posing next to it as if they were fighting. A big plush of a blue, bug-eyed dog with its tongue out was seated on a tiny rocking chair right beneath some framed piece of nonsensical modern art. A big TV She wasn't a hoarder, but she certainly had strange tastes.

"So welcome to the Tips house!" Tips said proudly. "Help yourself to whatever you want!" She gestured to one of the nearby dressers. "The vibrators are in the top drawer of the little dresser. Just clean them off when you're done. The bigger stuff's in the middle drawer. Butt plugs in the bottom. Gyahaha! Get it?"

"Ha! Yea," Boss chuckled as she started to unpack. She plugged in her phone near the sofa. "I guess I'll take the couch, if that's okay."

"Oh please! You're the guest of honor. You can have my bed," Tips insisted.

"That's... actually really generous of you, Tips. But I'll be fine. I've been sleeping on couches all week." Boss managed to hide her cringe as she imagined the kinds of things Tips must do in that bed with god knows what sort of people.

"Well the offer still stands. Hey! How do you feel about chicken alfredo? My mom gave me some of her homemade sauce a while ago and I've been looking for a special occasion to use it!"

"That... actually sounds great. Thanks, Tips." Boss would have imagined she'd be tired of Italian food after working in a pizza place for so long, but it sounded surprisingly tempting when Tips put it like that.

"Awesome! Go ahead and pick out a DVD while you get settled. We can watch while we eat and then I can do your hair!"

"Do my...?" Boss just watched Tips hurry off to the kitchen, humming happily to herself. Boss shook her head, but she had to smile. Tips was a happy go lucky ditz, but she rarely saw her look this happy unless she was surrounded by dicks or money.

It was a shockingly pleasant night. Tips handled dinner herself and it was surprisingly tasty. They binged on one of her box sets while Boss moved to sit in Tips' beanbag chair, conceding to let Tips undo her hair buns and start messing around with a braid. The strangest she got was halfway through the braid, she clapped her hands and suddenly stood up.

"Ooh, excuse me a sec. I'm gonna go use the bathroom." With that she hurried off to the bathroom and locked the door. Nothing that unusual until Boss heard the familiar buzzing of a vibrator through the door. She sighed and popped out her phone, turning on a random video to block out the noise.

"Still not as bad as Chad," she admitted to herself. Tips came back a few minutes later with a big fanged grin on her face, merrily sitting back behind Boss. "Done venting?" Boss asked knowingly.

"Yup!" Tips replied without a hint of shame. "Thanks for asking! Could you pass me that hair tie?"

Boss had a pretty relaxing evening, watching shows and chatting about them with Tips until she noticed the time. "I should probably get to bed. I gotta be in early to sign off on our sausage guy."

"You could always leave the sausage man to me! Gyahaha!"

"I absolutely could not. You know where it would all end up, and we can't serve that shit. This is supposed to be Tips-free sausage. I can't just tell everyone we're out of sausage because Tips fucked it all."

"Again," Tips giggled. "Well then I'm gonna go get ready for bed. Go ahead and knock if you need anything!" With that she did just as she said; she carefully brushed and flossed over her braces and fangs before removing some of her makeup. heading She went into her bedroom and shut the door tightly before she climbed into bed. She calmly opened up her nightstand’s drawer and pulled out a twelve-inch long, lime green vibrator. She couldn't kick her panties off fast enough, barely past her thighs when she stuffed the thick head into her neatly shaved pussy.

Tips' fang bit into her lip as her eyes rolled back, slowly pushing it deeper to fill her wet pussy. She let one hand manipulate the toy, grinding its tip around her clit while her other hand peeled off her t-shirt. She licked some drool from her lips in anticipation before she switched the vibrator on. It hummed to life, shaking right next to her clit in a way that made her toes curl and an eager squeak escape her lips. She slid it deeper inside her slit as she spread out her pale thighs, sliding the panties down around her ankles as her hips lifted off the bed. She started groping at her freckled tits, bouncing them in her palm while her fingers teased their way around her nipples. For as active a sex life as she had, she had perfected her masturbation ritual. Nobody knew Tips' body better than Tips. It wasn't log before she grit her teeth and let out a low, drooling chuckle as she shoved the vibrator as far as it could fit and squirted around it, leaving a wet puddle at the foot of the bed. She flopped back onto the bed, sighing contently with the still shaking sex toy stuck between her legs.

"Well that was a good day," she decided out loud. She switched off the toy and gave it a quick once-over with a towel. By the time she had it hidden again, she was read to pass right out to sleep.

A few days went by that were much of the same. Tips would excuse herself for some furious masturbating once in a while, but otherwise she was an excellent hostess. Their coworkers were surprised when Boss started showing up to work well-rested and with no complaints to speak of. When Wednesday rolled around, Boss came back to the apartment and was greeted by a saucy smell.

"Is that chow mein?" Boss asked as she set aside her purse and a couple of shopping bags. She went to find Tips already cooking in the kitchen.

"Yup! Just a little something I've been meaning to try out. I kept swapping ideas with Chef until I finally went for it tonight. I think it turned out alright."

Boss smirked at the sight before bringing up her point. "So they called me at work today. My apartment's all fixed and I can move back in tomorrow."

"Oh! Well that's good!" Tips turned and hugged Boss tightly against her stomach. Boss begrudgingly let her squeeze her while her tits rested on her head. "I'll miss ya, roomie."

"Yea, well... you were actually really nice through all of this," Boss admitted. Once Tips let her go to check on the chicken, Boss held up a large shopping bag. "So I got the guys that helped me out a little something back at work, but I thought you'd like this as a thank you gift." Tips switched off her burner as she took the bag and peeked inside. Tips gave a happy gasp as she lifted out a big plush of a busty goblin making a winky face.

"OMG she's so weird and cute! I love it!" Tips gushed.

"Yea, I noticed you like weird stuff. I just thought you helped me out, so I'd do something for you. Sooo..." Boss' eyes roamed around the room as she worked up the nerve to finish. "If you... wanted some help getting off tonight, I'd be okay with it. Just this once." She trailed off as she blushed, but Tips' eyes went wide.

"Seriously!? Yes!" Tips' blurted, bouncing up and down so hard her tits nearly knocked over the frying pan. Boss smiled from Tips' infectious excitement. It wasn't hard to predict that the offer would go over well. Whenever Tips was in the other room, the sounds made it obvious she was either masturbating or really enjoying mowing the lawn.

Tips quickly started to combine the chicken with the the noodles. "Come on! Let's hurry up and eat so we can pick out a strapon."

"Still in the middle drawer, right?" Boss asked casually as she climbed into her seat.

"You know I never actually got to use one of these before," Boss confessed. Tips hopped into her bed naked while Boss adjusted the straps around her hips. They had settled on a midnight black number around 9 inches long, not too detailed but still keeping the general shape of a real cock. Tips had wanted big, but it was a happy compromise of something decently sized without looking too ridiculous on someone as short as Boss.

"Oh they're a blast! I dated a guy who was really into those," Tips said conversationally. Boss climbed into bed after her, balancing on her knees. As the glistening rubber rock wobbled, she could see Tips' eyes follow its every movement. "Sooo...?" Tips pried eagerly, her fingers digging into the bedsheets to contain her excitement.

Boss smirked at her and stood up to level the strapon with her face. "Well it's not going to lube itself, slut. Hop to it!" Tips squealed with delight and grabbed the rubber cock, obediently stuffing it into her mouth. Boss smiled down at her with some slightly sadistic amusement. Tips had asked for her to go a little rough on her, after all. She assumed it was some combination of her being a fraction of Tips' height and also her manager, but she didn't mind. In fact, she felt her legs shake a little. Tips had pointed out the much smaller piece of rubber just inside the crotch of the strapon that was currently teasing her clit now that the freckled nympho was really getting into it. She rolled her lips and tongue over the first few inches, slobbering all over it just as Boss had ordered. Whenever she pushed it especially hard, it made the inside twitch against Boss' snatch like an orally operated joystick.

"Come on," Boss ordered impatiently as she tugged on Tips' curly hair. "One more big one before I let you take it."

Tips nodded and opened her mouth wider, baring her braces briefly before she pushed her face forward. She opened her throat to take it up to the hilt, resting her nose against Boss' stomach. She gave a few wet gulping noises, but Tips' gag reflex had always been exceptional. Boss let out a brief moan as she grabbed Tips' hanging breasts, kneading the huge and soft orbs around like she was milking a cow. Tips looked up eagerly at Boss until she pet her head lightly.

"Good enough. Now show me that big ass of yours so I can put it to good use." Tips nodded again, making Boss' end of the strapon twitch before she let the soaking wet shaft back out of her throat. She gave it a quick kiss and turned around on all fours, Boss slapping the pale freckled booty as soon as she saw it bouncing into view.

"Pick up the pace, bitch, before I change my mind!" Boss scolded.

"Eep! Right, Boss!" Tips chirped happily as she turned all the way around, raising her ass into the air and spreading her chubby thighs enough to offer her invitingly wet pussy. Boss sized up the well-used holes before she slapped her hands on both of Tip's cheeks as once, sending them jiggling wildly as Tips lowered her hips obediently. The repositioning left Boss the reach to slide in closer and press her cockhead against Tips' anus, rubbing the wet tip around the hole before she finally pressed it inside. Tips let out an appreciative little cry as she hugged the pillow in front of her. Boss smiled to see her long legs kicking childishly behind her.

"You like that, you overgrow buttslut? Wait until you feel the rest of it," Boss threatened softly. She buried her fingers into Tips' meaty booty and leaned into it, bending her short torso over Tips' ass as the sextoy slid inside her. She caught and pulled on some of Tip's hair to make the entry easier. She had known Tips to take even bigger and rougher than that, so she wasn't worried about hurting her. Tips gave a husky purr of delight as Boss buried it up to the base inside her, slightly masking Boss' own grunt of pleasure. Boss kept the double-sided strapon pumping in and out, the meeting of her hips with Tips' ass making a satisfyingly loud slapping sound to go with the tingling impact with her pussy.

Once she really started getting into it, Boss reached around one of Tips' thighs and started to roughly finger the taller girl's pussy. The quivering coo that it got out of Tips told her it was just what she'd wanted. She found Tips' pussy already dripping wet just from having Boss in her ass, drool running between her fangs as her face rubbed against the pillow.

"You're seriously that horny from all this?" Boss asked, leaning as close to the taller girl's ear as she could as she did her best to humiliate her. She took her hand back out to slap the cummy hand across Tips' ass, setting it right back to work singling out her employee's clit. "I can't believe I asked your horny ass if you wanted to do this and you actually said yes. You gonna cum, you dirty girl? Gonna cum like a horny bitch?"

"OHHH YES! THANK YOU, MOMMY!" Tips cried happily. Just some firm strokes of Boss' fingertip had Tips squirming and squealing beneath her, raising her ass higher like some kind of horny offering. Her huge tits squished out on either side of her torso, too big to fit underneath her upper body as she put more weight on them. Her ass cheeks bounced along to the rhythmic pumping as Boss leaned harder into the thrusts, digging deeper into Tips while her shorter end pressed more firmly against her clit.

Tips finally broke into a screaming orgasm, her high-pitched voice cracking as her butt bounced in a rapid humping motion. Her hips bounced from Boss' cock in her ass to her fingers in her pussy, effectively plowing her from both sides as she gushed her sloppy orgasm over her roommate/employer's hands. On Boss' end of things, Tips' wildly bucking hips made it feel like she was riding a mechanical bull that had just got turned up to Expert. The stubby attachment pumped her pussy until her eyes glassed over and she felt her own quick rush of heat and moisture rush through her loins, trickling down Tips' tensing legs.

Tips finally eased her legs to a halt and melted into the bedsheets. She gave a long sigh as she relaxed enough for Boss to pull the toy back out of her. Boss caught her breath as she leaned on Tip's ass, giving the massive booty an appreciative pat.

"I'm starting to see why the customers like you so much," Boss admitted, her voice a little higher and breathiner than usual. "I guess just having a dick helps."

"It's just that everyone likes service with a smile!" Tips chimed as she rolled over to lean on her elbow facing Boss.

"Oh yea? Then why do customers keep coming asking for me?"

"Cuz you're nice on the inside! Even when you yell and swear at people like me and smack me on the ass." Boss started to crack a smile before Tips went on. "Or tell me to stop snacking on pepperoni or to stop volunteering to clean the men's room when there's guys already in there or to stop grind dancing on Chef when there's paying customers or-"

"No," Boss cut off with an annoyed expression. "No, I get it. Thanks anyway." She sighed and started to tug at the bits of leather that kept the strapon clinging to her curvy hips. "How do you get this thing off anyway?"

"Aww, you wanted to get rid of it already?" Tips asked innocently.

Boss rolled her eyes and let go of the straps. "I mean as long as we have it on... it IS our last night together after all."

"That's right! So let's celebrate! Gyahaha!"

Boss spent her last night sharing the bed with Tips in more ways than one and headed out the next morning. She picked up Mortimer  and unpacked her things while she let him loose. He'd been fine and moody over at Chad's, but he seemed to enjoy being back on his own turf. "Yea, yea. I'm glad to be back in my own place too," Boss agreed.

She finished unpacking and went down for her shift at The Thot, just to find Tips' wide and familiar ass squashed against one of the windows. She sighed and stepped inside, giving Tips a dismissively quick smack to her tits.

"Hey! If you're sitting around on the clock, at least don't get ass prints on the window!" Boss snapped.

"Gyaha! Gotcha, Boss!" Tips chirped as she hopped up with an eager salute. Boss gave her a nod and smirk.

"Atta girl. Now go clean that up." Tips quickly started unbuttoning her pants. "The window, dummy! Not your giant ass!"