The Holiday Discovery Ch. 08

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Anna's gift from Jane leads to very dirty tasks.
7.5k words
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Part 8 of the 9 part series

Updated 06/14/2023
Created 01/02/2017
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tach14
tach14
34 Followers

It's October 31st and one of Anna's favorite holidays is finally here. She's been home from her university this fall as this new pandemic has made it so online classes are her only option. Now twenty year old Anna is forced to celebrate Halloween at home. Anna's best friend Jane, the girl that Anna messed around this past summer has been quarantined with her family out of town. The last time Anna and Jane got together, they had a wild adventure, and it was a bit much for her at the time. They are on a break so to speak for the moment, and could possibly make things work in the future.

It is a dark and chilly afternoon in Anna's town. It's been an overcast Halloween so far, which compliments the spooky decorations on the houses in Anna's neighborhood. It definitely helps to add to the spooky Halloween spirit. At the moment Anna is wearing a dark blue pair of tight jeggings that cling to lovely waist and curvy ass. She's also wearing an orange sweater and black vest with a black bra and a black thong that rides up her ass a bit.

Anna has just finished up her lunch with her parents and younger siblings. Mother made a heavy casserole called shepherds pie with all sorts of vegetables as well as chicken. Anna looks out the window as she cleans her plate. She downs the rest of her tall glass of apple juice and cleans her face with a napkin.

It's foggy outside from a morning drizzle and will make trick or treating interesting later this afternoon and evening. Anna leans back in her seat feeling her heavy lunch beginning to settle, "Mmm thanks for lunch Ma that was delicious," Anna sighs with a smile.

Mother smiles and replies, "you're very welcome honey help yourself to some dessert! It's nice to have you around." Anna smiles back taking her plate to the sink wishing she could be with Jane. "Hey Anna would mind watching the door for trick or treating for a little bit when it starts this evening? Your father and I are taking the kids out before it gets too dark. Can you believe Halloween was almost canceled?!" Mother shakes her head laughing to herself.

"Um okay sure mom that works for me. I was honestly thinking about trick or treating later just for old times sake" She replies. Anna hears the pitch of the mail truck pulling away from the house and leaves the kitchen. Anna's been expecting a package from Jane and Jane won't tell her what it is. "I swear if it's more junk mail I'm going to be so pissed," Anna thought strolling out the front door.

Anna opens the door to find a package resting on the welcome mat. "Yay! It's from Jane! I wonder what it is?" Anna quietly squeals. The cool autumn air ruffles her light brown hair in the breeze. Anna shivers and gathers the other mail and rushes up to her room with the box. Closing her bedroom door behind her, Anna sets the box down on the bed and texts Jane, "OMG it finally arrived!" She finds some scissors and opens the cardboard box without hesitation. Anna eagerly folds back the cardboard lid and gazes on the contents of the gift. Her face lights up with a big smirk.

From what Anna can tell there's a letter from Jane and underneath is some articles clothing. Anna reads the letter, "Dear Anna, Happy Halloween! I would love to be there with you and go on one of our naughty adventures, but since we're so far apart I thought I'd try to give you something exciting for spooky season. Inside this box you'll find a bikini cut pair of bright orange panties with a candy corn pattern on them, a special costume for an extra dirty and naughty witch that includes black and orange knee high socks, a purple pleated skirt that falls just above your knees, a long sleeved black top that's low cut with strings crossing over your cleavage, and of course a black witches hat. You'll keep me updated on your day with videos and pictures. I've got some rather naughty dares for you to complete on Halloween listed below. Dare number one is to strip off whatever you are wearing, try on this costume, and make yourself orgasm. Oh and don't soak the new panties right away Anna I want you wearing them for the whole time on Halloween. Dare number two is something you struggle with, but with a twist. You will no longer be able to use the toilets in your house to relieve you bladder or bowels, so you'll need to get creative on how to go about relieving yourself. No buttplugs either Anna. That's cheating and you'll have to find other ways to hold in your messy poop. Dare number three is to also make this a pleasurable evening for you, as well as a few others. If you're gonna go trick or treating, give a few of the homeowners a tease if you are up to the challenge. Have fun And don't make a huge mess! Love Jane."

Anna reads the letter a second time to absorb the dirty tasks given to her. She snaps Jane a selfie showing her cleavage with the opened box in the background and makes the caption, "I accept you're dares! I'll have to make up something for you soon!" Anna sets her phone down and removes the contents from the box. Laying out the costume and panties on her bed, she looks outside her window and sighs with a smile, "I think it's going to be a fun Halloween after all."

Anna sets her phone up on her dresser and starts recording. She first takes off her black vest and tosses it towards her closet. Next are the jeggings. Anna faces away from the camera and slowly slides off her tight pants. She struggles a bit taking them off and hops around her room. Anna returns to the view of the phone with a smile. Anna carefully unclamps her bra and and covers her perky breasts with her arms. Her thong remains the only thing left covering her ass. "It feels so thrilling to be stripping at home! I hope no one walks in right now," Anna thought just imagining the look on either of her parents faces if they caught her in the act. She returns her mind to her thong. She dances around a bit freeing her boobs. Anna finally slides off the black thong, which is a bit damp already from her excitement.

Now fully nude, she can resist sliding a hand down towards her wet pussy. Anna slowly massages her clit and sits down on her bed. Breathing heavily, Anna moves her fingers quicker. Feeling her pussy begin to tighten, and an orgasm starting to build. Her hips thrust gyrate on her bed as Anna tries to moan quietly. "Mmm I'm gonna cum. Such a naughty girl," Anna breathes as she gasps loudly. A loud moan escapes as her body shudders from her climax.

As she catches her breath, Anna grabs a water bottle and takes large gulps almost downing the whole thing. "That's much better. Jane must've had some fun just thinking about coming up with this for me," Anna thought.

Anna ends the recording and snaps some cute photos of herself and sends everything to Jane. As Anna begins to look over her clothes she feels her tummy rumble slightly as a fart squeaks out of her butt. "Oh! Haha I guess lunch is kicking in. I better start thinking on where I can go to relieve myself soon," Anna thought grabbing the candy corn panties. She slides the soft orange underwear up her legs. They are a bit snug, but look super cute. After snapping more photos of the panties for Jane, she pulls on the warm orange and black stripped socks. Anna then puts on the purple skirt. It falls a half a foot above her knees. "It's very short. I wonder if I could even bend down in this thing. Thanks Jane," Anna says rolling her eyes and grabbing the black sweater.

Next Anna pulls in over her head and adjusts it. Jane didn't include a bra, but it's a thick and comfortable material. She still doesn't want to risk getting too turned on and revealing her perky nipples. The top is rather low cut and shows a few inches more of cleavage than her usual shirts. The string crossing over the cleavage is just a tease as anyone within several feet could easily make out her delicious looking breasts.

Satisfied with how the costume looks, Anna puts the witch hat on over her curly brown hair and snaps more photos for Jane. She feels a bit of discomfort in her bladder going down the stairs as a slight urge to pee creeps in. Anna pushes aside the thought seeing her parents and siblings getting ready to leave. "Um hey guys trick or treating doesn't start for another hour. Where are you going?" Anna asks.

Mother replies, we're going to visit our friends on the other end of town and trick or treat over there." Mother finishes adjusting her siblings costumes and says, "there's a little costume contest and your father and I want to win this year if you're questioning our outfits!" Mother snickers looking at her husband. Totally oblivious to her witches costume. Her father is dressed up as Dracula with a black cape, makeup and all. Her siblings are vampire bats, but mother seems to be looking for a bit more attention this year.

"Oh my um well I think I'll just stay back then mom. No worries here!" Anna says looking at her mother's costume. Mother also went for a vampire theme. Makeup and all, but with very tight black leather pants that are almost a size too small. They show off her rather curvy waist and plump ass that apparently her father can't take is eyes off of. Anna rolls her eyes and continues her gaze upwards. Mother is also wearing a torn white sweater with fake blood exposing most of her cleavage. Her boobs are one bounce from popping out. Anna blinks a few times before saying anything, "well... have fun everyone! I'll hand out candy for a bit before maybe going out myself."

Her mom and dad reply with the typical okay sounds good and be safe while clinging to each other. They take the kids out to the car and drive off. "Wow that's going to be quite a night for those two," Anna shakes her head with a smile.

Now home alone, she decides to throw a frozen pizza in the oven for dinner as she's still pretty full from lunch. Anna takes a moment to update Jane. She snaps an up skirt photo of her putting the pizza in the oven, and uses the caption, "I'm finally home alone! I also have a slight urge to pee. I better start thinking on where to go lol." Anna sends the picture with a smirk on her face and sees that Jane has replied to her earlier photos.

"Oh Anna you're so hot!! I can't wait to be with you again. I'll help you with finding somewhere to pee just this first time. Anna I want you to hold it a bit longer and continue drinking water for this evening. Don't ruin those panties yet though. You can pee in floor overflow drain downstairs in your basement." Anna's face quickly reveals a naughty grin as she reads Jane's response.

"Okay Jane I can do that for you! I'll keep you updated. I'll do my best to not soak my candy corn panties yet lol!" Anna replies. As she stands near the oven, Anna begins to shift her weight rubbing her legs and cute socks together as the urge to relieve her bladder grows a little stronger. Anna grabs a can of Mountain Dew from the fridge and takes some sips to keep herself distracted. She runs a hand over her bladder feeling it start to push against the waistband of her panties. Anna continues to wiggle in place next to the oven as she sips on her pop. Before she knows it, the bottle is empty. "Wow I drank that pretty quick. I better head to the basement in a minute," Anna thought.

As Anna turns to walk to the basement door, the timer beeps and shows a two minute warning. "Ugh! I really gotta pee now! C'mon Anna you can wait a few more minutes," she thought sticking a hand between her legs. Anna's bladder is getting full and difficult for her to hold. She bends forward and moans, "oh this is the longest few minutes of my life." Anna takes her phone and sends a few selfies to Jane with a worried look on her face and a caption, "I really gotta go now! Jane it's gonna be close."

Anna squirms and bounces in front of the warm oven. She bends down to look at the pizza, still grabbing her crotch. Her bladder spasms and Anna barely manages to keep the floodgates closed. Finally the oven beeps and Anna slides the pizza out of the oven. "Oh my gosh it's about time!" Anna cries as she closes the oven and hobbles towards the basement. She reaches the steps and halts in her tracks as another spasm hits her bladder. Anna gasps as a few dribbles of warm pee drop into her panties. "Oh no I'm so close now," she breathes very worried.

Anna gently takes the stairs down and sighs when she reaches the bottom. On the bring of a major accident, she reaches the drain. Anna sets up her phone and starts recording. Anna stands up and does quite the pee dance as she holds her tiring bladder for a bit longer. Bouncing her legs and moaning softly, Anna looks at her phone with a very desperate face, "oh Jane I really need to pee I'm so desperate. I can't wait any longer!" Anna turns around and bends over flashing her orange panties and her skirt rides up. She carefully slides down her underwear and squats over the drain.

Anna sighs loudly of relief as she releases a warm stream of hot pee trickles loudly down into the drain. As her bladder continues to empty, Anna breathes, "I feel so much better now thank you Jane," as she looks back at the phone with a smile and wink. She stands up and pulls her panties in again. "Just a few wet spots. Not too bad," Anna giggles to the phone before stopping the recording. She returns to the kitchen to have some supper and relax before another desperate situation arises.

Adjusting her costume, Anna grabs a tall glass of water and a plateful of some greasy meat lovers pizza. "Mmmm my favorite pizza brand too. Thanks mom!" Anna thought digging in to her dinner. She ate carefully not to make a mess on her costume. After eating her third big slice, Anna finishes the cold glass of water. "Oh I'm definitely stuffed now. That was really good pizza," Anna sighs cleaning up.

As Anna washes her few dishes and bends over to set them in the dishwasher, her stomach makes a low grumbling noise. A small fart ripples out from her ass. "Oh my! Um well I guess I'm gonna have to take a big shit later tonight. I should be able to wait till everyone comes back," Anna thought now done in the kitchen. She sits down on the couch to relax and as Anna reaches for the TV remote the doorbell rings. "Oh my gosh already?" Anna thought rushing out of her seat. She hustles to the front door and grabs the bowl of candy.

Anna opens the door and gets bombarded with a few kids yelling, "trick or treat!" She puts on a smile and hands out some candy. As the thank her and leave the porch, Anna looks around the neighborhood. There's a few hours of overcast sun left and there's a lot more people out trick or treating than she thought. Anna closes the front door and leans on the half wall next to the front door. She feels her full and heavy stomach gurgle again.

The doorbell rings again. "Oh boy more trick or treaters," she sighs reaching for the door knob. As she opens the front door with the candy, a juicy fart slips out. Anna clutches one hand to her stomach grimacing slightly. Luckily no one got scent. She breathes relief as that group departs from her house. Anna grabs her phone and updates Jane on what's going on.

Jane replies, "well that doesn't sound very exciting for you Anna. Why don't you tease yourself some more right until the next trick or treaters show up?" Anna's eyes widen as she reads Jane's naughty suggestion. A little smile curls from her lips as she runs a hand under her purple skirt. Anna gently teases her clit over her candy corn panties with her middle finger. She feels her cheeks brighten as a sharp gasp of pleasure and soft moan could be heard in the doorway. Anna rotates her middle finger as her tight warm pussy aches for more.

Just as Anna thinks about bringing in another digit, the doorbell rings again. She sighs as a little wet spot forms from her damp pussy. Hot and bothered, Anna grabs the bowl of candy and opens the door. Anna's full bowels grumble again, as she's is no longer distracted by her teasing finger. Anna forces a half smile as she tosses candy into the open baskets of the trick or treaters. A few of the male chaperones that are standing a few feet back from the porch are taking in a full gaze of her in this costume. "Well it looks like some people are enjoying this costume too." Anna thought avoiding eye contact and complimenting the trick or treaters spooky costumes.

As the hoard of trick or treaters yell thank you, Noticing the greedy eyes of the guys, Anna "accidentally" drops a roll of smarties behind her. She slowly turns around and leans down with only a small bend in her knees to snatch up the candy. Anna's short skirt exposes the bottom half of her juicy ass with a flask of orange panties. As Anna is bent over, her stomach gurgles louder than earlier as a bubbly fart erupts from between her cheeks. Her bowels shift and she knows a thick warm turd is going to be lurching it's way towards her sphincter really soon. Anna freezes for a moment taking the piece of candy. The last trick or treater looks back hearing her gassy noise, but keeps running down to the driveway and sidewalk.

She quickly stands and faces the group of guys with a bright smile, "happy Halloween!" Anna cries out noticing their eyes suddenly look elsewhere and one re adjusting what she assumes to be a boner. Anna giggles to herself and steps back inside. She suddenly gasps as her bowels continue to churn. Anna has to clench her ass slightly as the urge to shit grows. "Oh my gosh my tummy doesn't feel to good. I hope I can hold it until everyone comes home" Anna nervously thought to herself relaxing her sphincter. The urge to go subsided for now.

Anna sets the bowl of candy down and grabs her water bottle. She takes some sips to calm down after that cheeky experience. She texts Jane the details of her teasing the neighborhood daddy's. Anna sends Jane some up skirt photos and the little wet spot on her orange candy corn panties before the doorbell rings from eager trick or treaters. Anna quickly hands out the candy and returns to her phone screen lit up with a reply from Jane.

Anna sits down on the living room couch to help hold in her poop and to look over Jane's replies. "Oh you're such a naughty girl! I can't believe you showed those guys your ass! I'm sure if they need a babysitter they'll be knocking on your door." Anna smiles as she reads the texts and again slides a finger over her panties to tease her clit. She continues reading, "Anna I love your pictures I'm getting wet just thinking about seeing you in that costume. Speaking of wet, I recall the time last year around the holidays when you said you really had to pee. While on the phone with me remember?" Anna's smile grew recalling her wet fun. Anna presses her finger a little harder against her pussy. She moans and her body shivers with pleasure.

Now caught up with Jane's reply, Anna texts back, "I made a big mess after we finished that phone call. Jane I'm getting wet too. You're dares are so naughty I love it!" Anna types back. She closes her eyes and plays her wet shaved pussy some more, imagining Jane getting turned on. The wet patch grows on her orange underwear as Anna gyrates her fingers a little faster. "There better not be any trick or treaters here for a few minutes. Oh I'm getting so wet" Anna thought.

While slipping a finger under her panties, she feels an urge to pee creeping in. Anna also clenches her ass since her bowels were relaxing too. She doesn't stop playing with herself in hopes to distract her mind from her filling bladder and bowels. Anna's eyes open to the sound of a notification. She sighs and looks down at her phone. Jane sent a photo of her ass in a black thong and a text, "here's some motivation to keep being naughty Anna. I bet you are feeling the urge to pee if you've been drinking more as instructed. Don't think of the ocean or a water park. Especially when you're on the water slide in your bikini with the water sloshing and spraying all over your body. And when you get to the bottom unable to control yourself and drop into the warm pool. So much fun haha! Good luck!" Jane replies.

tach14
tach14
34 Followers