The Holiday Discovery Ch. 09

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Messy dares, desperation, public date and roleplay.
12.9k words
4.9
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Part 9 of the 9 part series

Updated 06/14/2023
Created 01/02/2017
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tach14
tach14
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Before we begin the next chapter, Anna and I have an optional fun interactive task or challenge for you as the reader. That is if you're up for it.

First, put on a pair of panties or underwear you won't mind getting a little wet or messy in. If you want have some naughty fun, first is holding and teasing your bladder. You'll drink 2 water bottles. Whatever size you have on hand is fine. Once you finish drinking all your water, then you will wait until you have an urge to pee to begin reading this chapter. I suggest reading chapters 1 through 8 to help pass the time as you bladder fills.

An additional task is to read this chapter while having an urge to poop. I suggest waiting until your usual time during the day that you have to go and then holding it. As you read and become more desperate to pee or poop, feel free to pleasure yourself for a naughty distraction. If you can't make it to the end of this chapter without needing to go, then you have to use the toilet with your underwear or panties still on. If you successfully hold your bladder and bowels until the end, you may use the toilet. Feel free to comment your results of your fun challenge.

Chapter 9

It's a cool Friday morning. Jane stirs and stretches her arms with a quiet yawn in Anna's bed. She snuck over the night before to spend some time with Anna before going to her internship today. "Good morning Anna," Jane whispers kissing Anna's soft lips.

"Mmm morning Jane. Did you sleep okay?" Anna asks running her hands underneath Jane's little pajama shorts. She gropes Jane's ass as she wakes up.

"Yeah I did thank you. It sucks I've got my internship today," Jane sighs enjoying her butt being played with as she rubs the sleep from her eyes.

"Oh cmon now it's Friday! Maybe I can make it interesting for you. Besides we've got dinner and evening plans right?" Anna replies.

"That's true Anna. What do you mean by interesting?" Jane asks sliding out of bed. She lowers her soft booty shorts and pulls off her sleeping top and is fully nude. Rummaging through her backpack, Jane pulls out her work clothes.

"Oh I'll think of something... I'm enjoying this little show right now," Anna whispers biting her lip as she stares at Jane. She climbs on all fours to the edge of the bed where Jane's ass is swaying in front of her face as she digs out her clothes. Anna bites her lip as she lightly pulls Jane's waist closer. She quickly buries her face into Jane's bubble butt.

"Ah! Oh Anna! I've gotta get to work soon!" Jane hisses. She shivers as Anna's tongue slithers around her tightened little asshole.

Anna slides two fingers inside Jane's warm pussy feeling how wet she's quickly become. She forces her tongue deeper into Jane's ass while gyrating her fingers in Jane's pussy.

Jane doesn't protest again as Anna's tongue and fingers work their magic. Jane moans softly hoping to not alert Anna's family members as an orgasm builds. "Oh fuck babe I'm... I'm gonna cum!" Jane gasps as her body shivers intensely. She feels Anna lick and slurp deeper into her ass and her fingers pleasuring her clit until Jane climaxes.

Anna feels Jane cum and slows down. She slaps Jane's ass before backing away. "Such a tease stripping for me like that," Anna winks wiping her mouth.

Jane catches her breath, "I wasn't... even trying... I think... you just wanted... to eat my ass," Jane whispers as she quickly pulls on a black push up bra. "I've got to go Anna I'm gonna be late!" Jane whispers sharply grabbing a light blue pair of panties and slides them up. This was followed by a tight dark grey pencil skirt that fell to just above mid knee. Jane then tucked in a white dress shirt and a dark grey jacket. "I'm just gonna use the bathroom quick then I'll slip out!" Jane smiles grabbing her bag.

"Um not so fast!" Anna says standing up and holding Jane by her waist. "First, my dad will be up with my siblings looking to use the bathroom any minute. Second, you'll have to hold it until you receive further instructions once you're at your internship," Anna whispers. "Cmon quick I'll sneak you out the back!" Anna says pushing Jane forward downstairs.

Jane freezes at the bottom of the stairs as she hears noises in the kitchen. "It's your mom!" Jane whispers her heart beating fast.

As Jane is focused on looking for a way out of the house, Anna quickly slips a small paper folded package in Jane's purse. "Okay we'll use the front door. Go now," Anna replies following Jane quickly. She opens the door and Jane stumbles outside. "I'll text you!" Anna whispers with a wink closing the door. She quickly returns to her room to grab her phone. Opening her snapchat, she plops down on her bed and quickly gets to work with some dares and tasks for Jane at her internship.

Anna feels herself getting wet as she types, "I hope you had a good start to your morning ;) Your first task is to drink a cup of coffee before settling in. This help get things moving. I'm sure you already have a slight urge to pee Jane, so your first dare with involve your bladder. As you become desperate, you can either use the restroom, but piss through your panties, or a trash bin in a cubicle and you can pull your panties aside. Your next task is to hold in your shit until your lunch break. I'm sure with the coffee you'll have a strong urge to empty your bowels. Your second dare is to relieve your bowels somewhere outside near the office, or you can use the bathroom, but it must be the mens room and you'll leave your panties in the stall. Finally Jane your task is to keep me updated the best you can. Also I'll hold in my shit all day to make it fair. I'll see you this evening for supper! Good luck! -Anna."

Jane briskly walks towards her house, which is just a few doors down and gets to her car. "Damn I wish I could've peed before I left. Well at least I don't have to shit right now though," Jane thought backing out of the driveway. She sees her phone vibrate and light up as she drives to work.

Upon pulling into the parking lot, Jane parks and grabs her phone. Her jaw drops as she reads Anna's message. She blinks a few times before typing a quick response, "I'll do my best Anna! These are pretty naughty even for me!" Jane's heartbeat quickens as she gathers her purse and walks inside the office building.

Jane's internship is in a two story office building where she assists full time employees with organizing files, typing memos of upcoming meetings, conferences, and company wide events, as well as keeping the workplace clean.

Jane tugs her short skirt down before taking the stairs up to her cubicle and the break room for the other interns. "I'll clock in and then get some coffee," Jane thought. "These dares from Anna will surly make today a bit more interesting," Jane thought remembering her naughty Halloween dares she created for Anna.

Jane brushes her blonde hair aside as she enters the break room. One of the other male interns Edward is sitting at the table playing on his phone. She smiles at him as she reaches for the pot of coffee. Jane bends down to the lower cupboard and rummages for a mug. Her pencil skirt rode up slightly as she wiggled around. Grabbing a mug, Jane quickly stands tugging her grey skirt down. Her cheeks blush bright red hoping her co worker didn't see her light blue panties.

Jane smiles and strides out of the break room with her coffee. She sits at her cubicle and texts Anna, "I just got my coffee. Might have accidentally flashed a bit of upskirt at a fellow intern!" Jane types. She boots up her computer and crosses her legs as her bladder presses into the tight waistband of her skirt.

Anna's phone buzzes as she gets ready for the day. She's now wearing a pair of little black athletic shorts and a pink tank top with no underwear. Anna's face lights up as she sees Jane's message and replies, "wow already getting into trouble this morning. I'm going shopping for a fun outfit for this evening just for you. Keep me posted Jane!" Anna grabs her purse and heads out to do some shopping.

Jane reads Anna's text and begins going through work emails. She adjusts herself a few times as her aching bladder slowly begins to distract her. "Fuck I gotta pee soon," Jane thought slightly wiggling in her seat. She gets up and walks to her managers desk and grabs a stack of files waiting to be sorted and put away. Jane swiftly heads to the filing cabinet's in the back corner of the office.

She puts a few files away and texts Anna, "I'm gonna have to pee soon. My bladder is pretty full and I've barely started on my coffee!" Jane wiggles some more as her growing urge to piss continues to hinder her sorting progress. "I really don't want to wet my panties and sit in them all day. Shit I better find an empty cubicle soon!" Jane whispers to herself reaching a hand down to her crotch to help hold her bulging bladder. Suddenly she hears footsteps and she freezes her pee dance.

"Oh hey Jane I didn't know you were back here. Thanks for taking care of the files," Edward says with a smile. He takes a quick glance at Jane as her skirt had ridden up with her wiggling. A few inches of her bubble butt were exposed.

"Oh yes no problem Edward! Thank... thanks for checking in!" Jane stutters pulling her skirt down again and blushing. She watches Edward walk away hoping he didn't catch her predicament. She waits a few more agonizing minutes and then carefully goes searching for empty cubicles. Jane quietly sneaks past her coworkers desks to the stairwell. She gingerly takes the stairs and reaches the empty first floor.

Her bladder throbbing, Jane takes short brisk steps towards the dark and dusty cubicles. "I can't wait much longer there better be something I can go in!" Jane whispers to herself checking the first few cubicles with no luck. She pee dances to the next group of cubicles checking under their desks. Jane finally spots a small black trash bin with crumbled up paper inside. As she reaches down Jane hears a voice calling, "Jane? Are you down here? I just wanted to let you know I finished up sorting your files!" Jane stops reaching for the bin and shoves a hand in her crotch.

Jane waits and hears his footsteps disappear upstairs. "That was close! I'm bursting!" Jane sighs with a wrinkled brow as she lifts her skirt. She lowers her light blue panties that now have a little dark damp spot, to her ankles. Sliding the waste bin below her, Jane breathes loudly as her bladder finally relaxes and warm pee splatters on the paper in the waste bin. She sighs of relief as her bladder empties. The bottom of the waist bin is about a half inch full with her pee.

Once Jane finishes, she fixes herself and quickly returns to the upstairs office bathroom to wash up. Ah she sits down at her desk, Edward returns, "Hey Jane I wanted to let you know I finished sorting your files," Edwards says standing at the entrance of her cubicle.

"Oh thank you Edward that's very kind. I went downstairs for a moment. I sometimes use the bathroom down there," Jane replies swiveling around in her chair blushing a bit.

"Oh no worries. I thought the bathrooms were closed downstairs?" Edward asks with a rather confused look on his face.

"Um... the womens is open I believe... thanks for taking care of my files I'll talk to you soon!" Jane replies hoping to get away with her lie as Edward nods walking away. Edward is about her height, skinny but athletic looking with short brown hair.

"I really hope he's not on to me and my naughty tasks. "He is kinda cute though," Jane thought turning around once more facing her computer.

Feeling more relaxed, Jane texts Anna with updates on her risky morning pee and sips on her coffee. She gets up and cleans up the dishes in the break room.

Meanwhile, Anna's phone buzzes just as she enters a dressing room. Anna's picking out a surprise for her and Jane for their after dinner plans. After stripping to just her underwear, Anna feels herself getting wet while reading Jane's updates. She sends a naughty pic to Jane of her ass in the black thong she's wearing and texts, "you're so hot babe! Maybe you'll have to introduce me to Edward sometime lol. Send a pic of your panties too!" Anna then returns to her task in the dressing room. Her full bowels make her stomach feel very heavy as she continues her fun shopping trip.

Jane returns to her desk moments later and checks her phone. Her cheeks flush as she sees Anna's thick ass in the thong. She quickly sits forward and snaps an upskirt picture of her damp panties. As Jane sends her naughty picture, she feels her tummy rumbling and gurgle. "Uh oh I think I'm going to need to shit soon," Jane thought adjusting her legs bending slightly forward in her chair.

A half an hour passes by as Jane works on typing memos for the full time staff on new policies and future conferences. She takes the last swig of her coffee and gets up to return it to the kitchen. Jane's tummy rumbles as she walks causing her brow to wrinkle. The all too familiar feeling of bubble guts forces her to shiver. "I don't think I can wait till lunch. I'll have to ask Anna if I can go soon," Jane thought reaching the kitchen.

As Jane puts her mug in the sink, a smelly pre poop fart bubbles out of her ass. She quickly clenches and nervously looks around seeing she's alone. "Fuck that was close," Jane sighs texting Anna, "hey Anna, can I please use the toilet now? I don't think I can wait until lunch. Please?!" Jane quietly returns to her cubicle anxiously waiting for a response.

Jane's bowels release more rumbling pre poop farts stinking up her cubicle as she impatiently waits for Anna to reply. Typing away on a few memos, Jane attempts to distract herself from her smelly predicament.

Another fifteen minutes pass as Jane anxiously bounces her feet awaiting a reply. Finally her phone buzzes with a text notification from Anna, "Trying to duck out early on your second task? Unless you're on the brink of pooping your panties I believe you can hold it Jane. For trying to get out of your dilemma, now you have to shit somewhere besides a toilet and leave your panties with your phone number inside behind. I'm almost finished shopping! Keep me posted love!"

Jane groans as she reads the text. She quickly types a reply, "Ugh fine. Yes I'm a big girl I can wait! I'll reply when I can Anna." Jane sighs as another fart escapes. She fidgets in her seat and looks at the clock. "Almost an hour until lunch. I think I can wait in here until then," Jane thought noticing a slight urge to pee again.

A few minutes later, Jane hears a repetitive tapping in her cubicle wall. Jane jumps up with a squeal spinning around as she startled. "Who's there?!" Jane breathes as a small fart squeezes its way out.

Edward peeks from around the entrance of her cubicle with a smirk, "Jane did you forget about the intern meeting before lunch? It's about to start." Edward wrinkles his nose but doesn't say anything not seeming to mind the smell of Jane's cubicle.

"Oh my gosh thank you for reminding me! Let me grab my notebook I'll be right there!" Jane blushes with embarrassment hoping Edward doesn't smell her gas.

Jane quickly gathers her things for the meeting and hurries towards the conference room. Jane blushes as she's the last one inside and quickly takes her seat. Her supervisor has a PowerPoint presentation for office ethics and procedures. "Ugh boring. I'll have to take notes to stay awake," Jane thought looking around. The other interns don't seem to thrilled either. Edward is to the right of her at the end of the long table. She smiles at him before turning her attention to the screen.

The first few minutes go by smoothly but then Jane's bowels begin to gurgle and rumble. She fidgets in her seat and moves her free hand resting it on her bloated tummy while she takes notes. The monotone lesson and presentation isn't helping with distracting her from her growing urge to poop. Jane feels more pressure building up against her anus. She clenches it shut while trying to keep her composure.

Another ten minutes creep by and Jane's slight fidgeting is becoming a bit noticeable as a few of her coworkers glance over at her, "ugh I really need to poop! Just another half and hour and I'm free," she thought with a loud sigh as she scribbles down more notes.

Hearing her sigh Edward leans over, "hey Jane are you alright? You seem a little... distracted," he whispers watching Jane shifting her weight side to side in her chair.

Jane leans over, "um... yeah I'm alright. Well I can't lie... I kinda need to use the restroom," she whispers back her cheeks flush red with embarrassment again.

Edward adjusts himself as his cock begins to harden, "oh no, I'm sure you can hold it until lunch," Edward whispers back encouragingly.

Jane nods her head in thanks as her upset tummy loudly rumbles causing Edward to glance at her again. Jane is slowly losing focus on the presentation as the urge to piss is also becoming a nuisance in her struggling state.

"Cmon Jane like fifteen minutes and you'll be able to go. You've got to prove that you're a big girl to Anna!" Jane thought to herself. Then Jane's tightly closed anus loosens for a second releasing a muffled fart. Jane's eyes widen as beads of sweat roll down from her forehead.

Edward looks over at Jane who's fidgeting quite a bit as she's almost unable to sit still. His hard cock is fully distracting him from the presentation as he eagerly watches Jane's desperate struggle. He carefully reaches under the table and gropes his cock through his pants.

Jane looks over catching Edward staring at her as she wiggles in her seat, "what the fuck? Is Edward turned on by me right now? We're in a meeting and I think... he's touching himself. That's kinda thrilling," Jane thought moving the hand from her stomach to over her panties. Jane accidentally drops her pen on the floor, which rolls under the table, "oops! Oh Edward can you please pick that up for me?" Jane whispers with a smirk. She subtly points to under the table as Edwards smiles back eagerly crawling under slow enough not to bring attention from the other interns.

Once under the table, he looks over seeing Jane's fidgeting legs uncross and reveal her blue panties from under her skirt. Her index and middle finger are pressed against her pussy. Edward grasps the stops for a second as Jane's fingers slowly gyrate. "She's masturbating for me, under the table, during a meeting. This chick is very naughty," Edward thought as he snaps out of it.

A dirty idea pops into his mind and Edward slowly takes the pen and pokes Jane's now damp panties.

Jane sharply gasps while looking down seeing a hand holding her black pen as it teases her pussy. She moves her fingers away and Edward moves the pen gently against her damp patch of her panties.

Moments later, Edward returns to his chair handing Jane her now wet pen. Jane blushes and whispers, "thank you Edward," with a smirk. She brushes her straightened blonde hair behind her ear happy to be distracted from her desperate situation for a few minutes.

As the presentation comes to an end, Jane's fidgeting worsens as she unable to sit still. Her urge to shit is quite strong as she feels a turd beginning to press against her tight anus. Jane's bladder isn't fairing any better as the coffee has effected her urgently need to pee as well. "Almost done! Then I can finally go!" Jane whispers to herself as a quiet pre poop fart bubbles out. "Maybe I can relieve myself quickly behind the dumpster and the parking lot," Jane thought giving up all focus on the meeting.

As the last few slides are finished, her coworkers slowly file out as they talk amongst themselves about where they're going for lunch and weekend plans. "Thanks for grabbing my pen down there," Jane winks as Edward as he leaves the conference room. She seems him smirk as he exits and heads for the break room. Jane walks briskly towards the stairs with a hand in her crotch.

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34 Followers