Jennifer's Misadventure Pt. 01

This is an entire work of fiction. It is not condoned to be real. The characters in this story are 18 years old and over.

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Jennifer's hand slid down her underwear and into her panties. This was her rubbing time.

Moments in feeling her pussy, she remembered having her legs held in the air and how humiliating it all felt.

"Oh sir! Please! Not my ass! OH! Ow! I'm sorry sir. Oh, sorry you lost your job. Ungh. Ungh! It wasn't me! Ungh. Oh, I didn't steal before! Oh fuck!" She pictured her body on a big black man holding, rather impaling, her onto his lap. While current Jennifer rubs herself some more, eyes closed on her bed.

With his grip on her, the big man bounced her up and down on his raging cock. Every sweet part of Jennifer bouncing away as a fat cock pumped into her asshole. Making the dumb babe, squeal and moan from the ass fucking was fueling him for...more ass fucking. But Jennifer didn't know that, she just thought he was an angry man committed to butt fucking her for all his worth.

Oh, she couldn't believe how much that enraged man slammed her down on his fat cock. She pets her pussy harder and faster. Oh, she couldn't describe how humiliated that anal position felt. She rubs harder. Oh, she couldn't imagine she would take another big cum load in her ass, but she did. And then Jennifer found her spot and creams her pussy.

Oh fuck, oh damnit. Jennifer thought to herself. She hated how memories of her humiliating sexual experiences sneaked in her head when she's alone in bed. Still, she loved how good it felt to cum. She smiled and went to sleep.

Ready to look for more work again. Jennifer returned to her babysitting job for another four months. Simple short babysitting gigs that she did. Nothing special. Other than obvious male stares at her ass or tits. She swears one house squeezed her butt, from both the man and lady of the house.

Her next job seemed like a big deal. It was a 6-hour gig. Being the longest gig to offer, Jennifer got excited because she knew that was a good payment. So she clicked it quick. Then read that the assignment was for a caretaker of a teenager who would have some friends over while the parents were out.

"Well, I just gotta keep it a clean party. Shouldn't be too bad for me. They'll be busy with the party." Jennifer lasts thoughts the night before her job date.

The next day, she took the bus and got to the house. Arriving dressed in a small buttoned white cardigan, blue tanktop, and tight white jeans. The folks of the house instantly greet her at the door. Wait, didn't the parents look familiar? Oh well, no matter. They left quickly and again explained the job details; parents are gone on a date and their son will have some friends over. He was upstairs until the parents were gone.

"Hey, my friends are coming soon. Can I bring out soda for them?" In a sudden entrance, he asks but quickly walks by Jennifer to the kitchen, regardless of her answer. Wait didn't I see him before? Jennifer thought.

DING-DONG.

She opened the door and two of Brandon' s friends are there, both a young 18 years of age. She led them to the living room where Brandon was waiting. He greeted saying what's up and passing them a soda. Wait, when did I see him before? She questioned again.

DING-DONG.

She again opened the door and found one more friend to led inside. Then Brandon passed both her and the new guest a cold soda. She drank and shyly stared at the young men, trying to recognize the one she is sitting for.

OH! FUCK WAIT! NO! YOU WERE THAT BOY WITH THE GRUMPY GRANDPA? YES! THE ONE THAT FUCKED ME! Jennifer yelled in her head after taking another sip. Jennifer started to remember more of the humiliation that his gramps did to her. She stays tight lipped (and tight asshole) and hoped the boy didn't remember her. Then Jennifer slowly blinked, things suddenly felt slow, and she closed her eyes.

Moments later.

Jennifer opened her eyes again. Coming out of a haze, Jennifer felt like she was somewhere else in the room. She's in the middle of the living room but she's on the leg rest, ottoman. Then her senses come back more, and she tried to move but realized her knees and elbows were tied to the small cushioned leg rest. It was small so Jennifer had her legs in tight and ass high in the air. Jennifer lost any idea on how she ended up there in that vulnerable position. She was about to scream for help, until she suddenly noticed Brandon again standing in front of her.

"So, I finally got you again. The sexiest babysitter I've ever seen." Yup, he knows Jennifer alright.

The young lad explained that he wanted this moment so bad. That he was annoyed his mom and dad would use a baby-sitting service on him, even though he was older now. And since his 18th birthday was a couple days ago, convincing his parents for a cool weekend with his best friends was easy. Almost as easy as lying about the child's age in the babysitter app. Apparently, he referred the babysitting assignment straight to her once he found her. But how did he know her employee number? She thought to herself.

"And gramps told me everything you did for him. You naughty ass girl." He seemed to lick his lips after speaking, almost savoring this moment.

"Oh well, I don't know what you mean but this is going too far! Let me go...uh...umm...what's your name again...sorry." Jennifer looks up with big eyes and seems to wiggle her hips in efforts to get loose.

"And you don't even remember my name! What the fuck!" He stepped back, rubbed his head, and pointed to one of his friends. He says "Hey, show her what we have."

Suddenly Jennifer had a camera screen brought to her face. She gasped at the images on the phone. It was her on the couch with her hands on different cocks, the teenager's cocks. Then her tits were out and in their faces. Then her bending over a couch with her head in every one's lap, cock in her mouth.

"Oh my! Whoa! You do all that?! Why! Oh, why are you doing this?" Jennifer pleads.

"Because now these photos can make you look real terrible on the job and become criminal. So, if you want me to delete the photos, you gotta play nice with us. Okay? Can you play nice with your sweet ass body?" He lowered his faces to hers and looked more serious than before at her. "Can you?"

She gulped and said "Y-yes. Yes, I can play nice. Please just delete the photos. I'll be good." Jenifer feeling completely lost in the situation.

"That's great babe." He stood up erect. "Oh, and my name is Brandon." Jennifer saw his friends encircle him and they tried to discuss in secret. The young woman felt uneasy about what they were saying and then felt even worse when she finally realized what she was now wearing. Earlier Brandon had her complete focus, but she now sees her damsel attire.

Now with her tank top and bra completely removed, Jennifer sees that only her buttoned white sweater is on her. She notices how only one button is holding her big tits in cover. Jennifer groans where she looks to her hips and notices a white skirt. No longer wearing pants, she feels her bare butt peeking out on the other side. She can't believe it's escalated to this already.

"Oh, it's about to get worse...for you." Brandon walked up to Jennifer again, and he placed down a small box. He quickly rummaged in it and pulled out a headband with white kitten ears attached. He placed it on her head. Her dumb face expression was priceless.

"That's for your head there." He looked back in the box. "And this...this is for your butt." Then Jennifer gasped when she saw what came out of the box. Brandon showed her a chrome butt plug. One that included a fluffy white cattail extending from it.

"Oh no! Please don't. You're not putting that in me!" The buxom twenty-one year old nervously pleaded.

2 Minutes later.

The buttplug was in her ass. It was snug in her tight butthole. Brandon had lubed it up and entered her ass with a forceful push. She had gasped and moaned when it entered her anal ring. His friends were so intrigued that they all took turns removing and reinserting the plug into Jennifer's asshole. Her tush was shaking to each penetration and swaying the tail nicely.

"Oh fuck! Whoa! Oh please! Not my ass. Oh ow. Not in my ass please. Ah fuck." Jennifer tried to look over her shoulder to better see the long white tail.

"HA! That looks A-mazing!" Brandon was genuinely excited. Jennifer watched the boys huddle together and speak quietly. She wondered if they were having second thoughts about doing this to an innocent 21-year-old buxom brunette.

Then one of the friends ran to another room and returned with an old happy birthday balloon floating in the air. He smiled and walked behind Jennifer. She is completely lost to what could happen, then she felt hands spreading her ass.

"OH! Hey, wh-what are you doing?! Hey! I'm not this type of girl. Aye!" Jennifer noticed a tug on the plug lodged in her asshole. And that it didn't go away. She peered over her shoulder and was shocked to seeing a balloon tied to her cat tail. The floating balloon was holding her cat tail straight up in air and lightly tugging her ass plug. Jennifer was stunned speechless to this treatment. Groaning to her treatment but not fighting back against it either.

"Oh fuck yea!"

"That looks so sick!"

"Yo, that was a good call to tie the balloon."

"Damn her ass is nice."

Jennifer heard all their comments. Then it got quiet. But before Jennifer could say anything, the boys started spanking her bottom. She's flushed with humiliation realizing that these teenagers are touching her exposed body and tormenting her. Suddenly the bindings loosen, and the dazed babysitter was forced to stand up. Jennifer sways her hips standing up, then she noticed it. She noticed her skirt being pulled up from the dang balloon that they tied to the cat tail.

"Yes, now she looks like she has a happy tail! It worked!" The nerd looking friend was excited to see his idea in full humiliating effect. High fives were given.

Jennifer's thoughts struggled to process because she felt so embarrassed and shocked to be in this outfit. Her skirt constantly raised from behind, showing off her naked butt that was holding onto a cattail buttplug. Jennifer was whimpering because of the constant pressure of an object lodged in her ass. She stood up wiping her tears.

"Ok, that looks great. Jennifer, you look great." Brandon walked around her and enjoyed every angle on her. The ass was revealed by the yanked up skirt. "She looks like a happy kitty. A nice happy pussy."

BANG-BANG

Suddenly a bang on the door and Jennifer gasped like she got pinched on the ass. "Oh yea, I forgot to mention..." A friend opened the door and two old men started walking in.

"Hey gramps!" Brandon yelled. He embraced one of the men coming in. Jennifer turned around and couldn't believe what she saw. The same old man that tortured and humiliated her last time she was near this boy. Oh fuck! Jennifer what am I into?!

The two old men walked inside and smiled at the damsel looking uncomfortable in front of their presence. Jennifer didn't run away but stood in place looking embarrassed.

"Damn boy, you did it." Butch walked closer to this very familiar babysitter. He touched her face and enjoyed the sight of her. He whistled when he saw the raised skirt and cattail plugged in her naked ass. He pinched her juicy butt and slapped it hard. Her squeal greeting Butch's ears.

Brandon peered around for someone else. "Hey Gramps, where's Harry?

"Oh, he died." Butch stood straight up. "The old fart died just two days after pounding this sex doll." SPANK. He spanked her to get over his conversation. Next, he looked around the living room, then looks elsewhere. "Hey, your folks have that nice backyard. Come on, y'all." Butch pulled Jennifer by the arm.

He led everyone to the backyard. Soon, Butch and Jennifer were standing outside in the middle of the afternoon. The other new friends and old friend Richard stepped outside to join them. Butch looked around the backyard. He spotted the outdoor table and ordered Jennifer to get on her hands and knees on top. She showed hesitation and then reluctantly climbed on the tabletop. She got in position and immediately felt her skirt raise up in the air. Her small cardigan barely holding her tits from spilling out but the tit flesh was still very much exposed. Jennifer's face was getting red as the guys stared again at the happy cattail in the air that leads to a plug stuck in her asshole. Her tight pussy peeking out to say hello kitty as well.

For about the next ten minutes, the two old men and four young teenagers rub, squeeze, and spank Jennifer's humiliated plugged ass. They each gave her round butt hard spanks and the sweet squeals from Jennifer gave them no reason to quit but continue. They went on to squeeze any part of her body that they wanted. Her tits and pussy received many gropes. She hated how everyone was touching her body and making her yelp when they smacked her behind. Jennifer hated how the plug felt large in her butt.

"Ow! Oh ow! Hey! Oh please! Oh...ow! Ah!" Jennifer squealed and swayed her hips. Offering every pair of eyes, a dancing ripe bottom. Even the pair of eyes watching from over the fence.

"Alright then" Butch grabbed and pulled Jennifer off the table. "Now that your ass is dressed. I want yer to listen. Go inside the house and get me two whiskey glasses with ice." SPANK. Butch's slap to the ass cheek got Jennifer scurrying towards the house. She hurried inside trying to keep her tits covered while at the same time, rubbing her sore butt.

"We're going to wet our whistle" Butch told his friend Richard.

Richard, still fixated on the sexy dame walking away, makes a whistle call. "Yup, we suuure are."

Soon enough, the dazed 21-year-old brunette walked back outside with two glasses for gramps. Then Brandon ordered her to retrieve their drinks, when she came back with the soda. Brandon pulled her over his lap and walloped her ass until it was bright red again. She was then told to get the beer from the fridge."

Moments later.

"I don't know man. I don't feel good about this"

"Is it right? Prolly not. Should we, do it? I don't know."

"Honestly, it's more upsetting than I thought I would be."

"Yea same."

"Should we tell Brandon something?"

Three concerned teenage faces meet with Brandon to share something. Something they found a little bit upsetting. Upsetting their stomach. "Hey, Brandon. I don't know if this is right... But I do not want to drink this beer, man. It's gross. Got my stomach feeling all shitty." He placed it down and patted Brandon's shoulder. The other two guys do the same.

Brandon took another chug of his beer and nodded to his friends. He then yelled "Hey grandpa this beer sucks. Give us some of your booze!"

"Fuck off! Not a chance. Enjoy the show!" Butch waves them off as he stares at the show in front of him. Jennifer was over Richard's lap getting spanked and groped.

Butch's friend found it necessary to keep the damsel's ass a bright red. Butches takes his final sip. Soon, Jennifer's squealing and yelping became the only noise around. Her squealing voice heard loud over the backyard.

A friend leans into Brandon and says, "Besides, I want to be ready to handle this ditzy dame that we got right here." He points towards the yelping brunette with kicking legs and bouncing bottom.

"Yea man. This is going to be great."

"Is it right? Sure is. Should we do it? Absolutely."

"Honestly, it's more beautiful that I thought it would be."

"Hey Brandon, everything okay over there!? Hmmm? What you got going on over there, neighbor?" Suddenly an adult male was heard over the south fence. Will Sanders is Brandon's neighbor and was watching Jennifer get spanked and groped. He wanted to test his luck and see if he could get in on the slut. He called over the fence just enough to see his eyes.

Brandon didn't want his neighbor to rat him out and he knew what his dorky neighbor needed; Jennifer's fine body. So, it didn't take much convincing when Brandon asked his neighbor Will Sanders to stay quiet about this naughty night. Will didn't think twice to answer when Brandon offered a sexual experience with Jennifer. Brandon promised him the first go at her in the bedroom, just him and her.

"I am not doing that!" Jennifer looked around hoping someone was going to say it was a joke. But everyone just ogled her and smirked at her situation. Looking confused, the babe looked around hoping that someone will say 'no' to the naughty act. Instead, Brandon grabbed her arm and led her back into the house.

Moments later.

Jennifer was waiting for the neighbor to enter the room, waiting for the neighbor, Will Sanders, to enter her. She's in Brandon's parents' room, on her hands and knees waiting on top of the bed. She was shaking and dreading what's about to happen. She can't believe that Brandon would be so cruel and allow this. She can't believe she was going through with it. She couldn't believe the bed was so damn huge.

"Oh fuck, this is bad." Jennifer told herself and stared at the many pillows on the bed. "They've plugged me and now someone's coming to fuck me? Coming to fuck me! Why am I doing this? I should stop - CLICK". The bedroom door opens, and calm footsteps enter the room. Jennifer shivers and hesitates to look behind her.

"Umm... hey, oh wow. You umm look amazing. I mean your body is gorgeous." The man walked up to the nervous brunette. "Oh, I'm Will, the neighbor. I'm here. Umm...I'm here to get a chance to fuck you." Will encircled Jennifer saying it.

"Oh! Sir! Well...I guess that's true. Ok, so let's get this over with." She puts her head down and offers her behind into the air. The neighbor takes a big gulp as Jennifer presents her round ass and tight pussy. He enjoyed the sight of a plug in this babe's big ass. He approached her and unzipped his pants.

For the next 10 minutes, Brandon's neighbor, Will Sanders fucked Jennifer in all three of her young sex holes. He first put his cock in her mouth to get it wet and then entered her moist pussy. Finally, her was rocking his cock back and forth in her tight asshole. She moaned and groaned during the ass fucking. But despite that awkward feeling of being ass fucked, Jennifer felt like this man was generally being sensual with her. That he fucked her with gentleness and slowness that she hasn't experienced in a while. It was different and it was great to her. His cock was nothing extraordinary, but it wasn't small either. She rocked her body back to him eventually. She wanted more of Will's thrusting in her pussy, and even when it was in her ass, she was okay with it. She wasn't grunting from a hard pounding but instead softy moaning to Will's tamed pace. When banging inside Jennifer's asshole, Will tensed up and orgasmed deep in her rectum. Jennifer squealed feeling how deep it was. The neighbor pulled out, she gasped, then he quickly reinserted the ass plug, and she gasped again.

"There, let's keep that in there. In that nice naughty ass." He patted her squirming bottom. "Well Jennifer, thank you for you that. Have a fun time being Brandon's fuck toy." SPANK. He landed a few more slaps and exited the room. Jennifer was trying to catch her breath and didn't say anything to Will. She hated how the plug was keeping the cum in her ass. But maybe, she thought, it could save her the humiliation since they didn't need to know that Jennifer got anal cream pied.

Jennifer slowly walked into the main room again and trying to adjust her small sweater and skirt. She heard the front door slam shut. The sex kitty did a visible jump in reaction from the noise and the balloon whooshed a bit behind her. She didn't enjoy the sight of 12 leering eye fuckers. Oh Jennifer, how do I get in this mess.