Jennifer and the Grumpy Old Man

This story is fiction. The author does not condone these actions in real life. The characters are of age. Story features forced, reluctant, ass play, spanking, public humiliation, and mmmf.

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Jennifer needed some work to get by. She needed something to keep her busy and earn some income. Keep her mind off the wild adventures her and her body have experienced lately. So she found a lot of side gigs online to work. One of those types of work she found is babysitting. Jennifer found it helpful at the moment and simple enough to do. Nothing could wrong with babysitting.

After doing a couple successful babysitting job through an agency that found her assignments, Jennifer sees an ad to babysit a young lad for an afternoon. Apparently the ad was from the grandpa who was willing to pay for it because he didn't want his grandson to wait in the hospital with him. The message explained that his son (the grandson's father) was taking him to the doctor's and his grandson was still working on a lot of homework. So instead of being stuck at the hospital because of the old man, he set up this time to finish his homework.

"Ok I can do that. Simple." Jennifer says as she clicks to accept.

~~~~~~~~ The day of the babysitting job.

The job actually goes without a hitch. The family is polite and the boy went straight to homework and then tv. He didn't want to talk much. Secretly, he's in shock and awe to view this babe Jennifer watching over him that day. Her curves are obvious and her skin is stunning to him. He would love just to get a pinch on that sweet round ass of hers.

"You sure I can't get you anything?" Jennifer practically twirls into the living room. She stands with her midriff exposed and jean shorts hugging her ass. The shorts were old and Jennifer's butt was filling up the cut shorts. Still her butt was covered at the moment. She wore a small white t-shirt. It ended right at her navel. Her clothes are more filled as she's grown up.

The boy stammered that he's fine. Sooner than later the family came back; while the young lad was cumming in the bathroom, thinking of his babysitter. They wasted no time in dropping off grandpa and getting their son in the car. Somewhere in the goodbye's, she thought the kid snuck a grab of her ass.

"Thanks for watching my grandson, lady. Let me get the cash over to you." He turns around and walks into a different room, out of sight. Jennifer stands in the living room. Shifting her feet, she looks around at the room and hopes the old man doesn't notice. She didn't want him to find out what she had done earlier. See, earlier, Jennifer found the old man's whiskey bar. She decided a swig would be nice. She saw the nice bottle and figured a quick swig would be nice. She even poured a little water in it to bring it back up. So Jennifer did a bad thing and she is hoping to get out and away. But she has to wait for the old man to come back and pay her.

He returns. With his phone in his hand. "Ok, I can pay you with my phone. I know how this shit works." He closes in on Jennifer. She brings out her phone to open the app from her babysitting agency. The old man suddenly grabs her phone and arm. His face gets inches from her stunning face.

"But first...why don't you tell me, how water got in ma fucking whiskey!" He waves a whiskey glass next to her.

~~~~~~~~~~~~~~ Minutes Later ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Outside, Harry is walking up the pebble road of the small mobile home area, and wants to visit his old fart friend Butch. He knew that Butch went for a hospital check up and wanted to meet up with him now. Make fun of him for getting a finger up his ass. Harry, a balding man, gets to the door, knocks on the screen door, and is replied with a young female squeal "OW! SPANK OH! PLEASE! SPANK! Ow oh!..." Then a pause.

"Come on in!" Butch rings out from inside. Harry opens the doors and walks right in his friend's little mobile home.

In front of Harry, is an unexpected glorious display of flesh. Butch is sitting in his favorite recliner and over Butch's lap, is the sight of a half naked 21 year old woman, glistening with a red perky bottom. Her small shirt fallen to expose her bra underneath and jean shorts at her ankles. Her round mound ass facing directly at Harry big eyes, giving him a grand view of her humiliated ass. Her panties are wedged so hard up her ass crack. It got pulled so tight her pussy lips are peeking out.

Despite all that, Jennifer couldn't really move. All she does is kick her legs back and forth with hands stuck holding her up, trying to keep her face from hitting the dirty floor. The old man really has her vulnerable over his lap. The exposed perky ass cheeks are high and center in the room.

"Oh my god! Someone's here! Stop spanking me! Ooh." Jennifer dumbly tries to use her hand to block any exposure, but Butch grabs the arm and pins it to her back. Jennifer is effectively pinned just as this other old man walks in.

She squirms her hips and whimpers in humiliation. Jennifer never thought it would get to this. After Butch yelled and confronted her about sipping his favorite whiskey, he sat down and whooshed Jennifer over his lap. He seemed more mad about the pouring water into his alcohol.

"Oh please! Sir! Come on! You've spanked me a lot already! Ow! Ah sir please!" Jennifer speaks to the old streaky grey hair man holding her half naked body. The young babe was in shock that Butch wanted to discipline her this way. For that last few minutes he has spanked her bottom over her jeans then her yanked those down to smack her bottom like this. With a tight very wedgied blue panty covering none of her ass cheeks. Jennifer's bottom is starting to get red at this point.

Harry walks up closer to the stunned girl and smug looking old man. "Alright, what the fuck is this Butch?" He stomps. "Not cool." Jennifer thinks to herself that maybe this man won't allow it anymore. She's wrong.

"Why didn't you tell me you hired a hooker over?! I would've bought another one!" Harry raises his voice to make his point. Butch soft chuckles and then giggles Jennifer's butt cheeks.

"Nah, Harry. This bitch here, SPANK SPANK,...this dumb girl thought she could try gramps drink and water it down to fool me! SPANK SPANK" Butch looks back at the damsels cheeks whenever he palms her young bouncy bottom. Jennifer yelps to each palm.

"Oh well I see. Hmm..." Harry goes silent. Jennifer can't really turn her head well enough to see his face. She wishes she can cover herself and end this. Surely, this man has spanked her enough. She is starting to regret agreeing for this client to apply his own punishment. He never gave her the payment so Jennifer felt trapped and wanted to end this privately. Suddenly Jennifer's mind is smacked by to reality when she feels a different hand smack her tush.

"So what can I do to help?" Harry squeezes her bum. "Help lay it down on this bottom?" Jennifer squeals when she realizes what Harry is implying.

Moments Later

Jennifer is on her hands and knees with her jean shorts still around her ankles. The old men are standing in front of her discussing something. They spoke too soft for her to hear what they had to say. What they had planned for her beautiful naïve body.

"How could I be so stupid, Jennifer! Damnit. The old man found out so badly. Surely, he'll let me go soon." Jennifer thinks this to herself as she watches the men approach her nervous body.

Butch speaks look darling, you fucked up when you took my booze. On the job and stealing and shit. Tsk Tsk. So like we agree on earlier, I'm going to punish you for damages. And then! I'll pay you." Butch gets closer to her face. "Ok? you got that?"

Harry reaches into his pocket and pulls a little switch knife out. He puts the knife in front of her and then steps behind her. She feels nervous to what he's thinking, but then suddenly, she hears a loud rip. The knife is cutting through her underwear. Harry shreds right thru her blue undies and leaves her ass exposed. He then slaps a cheek and walks away with the panties in his hand. "Souvenir" Harry says as he smells the panties and tucks it away.

"Dude...what the fuck with the knife?" Butch tells Harry. He motions for his crazy neighbor to put it away. Then Butch walks back to Jennifer still on her hands and knees. He admires the now naked ass crack of this young dumb babysitter.

"Ok, it's Jennifer right?...Jennifer, yer still getting punished by me and now my associate here. And so we're going to move to his place. It's just a short walk from here." He reaches his hand out to get Jennifer up. "Oh but this shirt is staying here with me." Then as Jennifer stands up, Butch grabs the shirt and pulls it off the distressed Jennifer.

"Hey! Whoa sir! My shirt! I don't know about this! I can't go outside like this." Jennifer hands cup her bra covered breast. She's surprised to find her shirt in the old man's hand. He's a fast one, Jennifer surmises. Then she gives a light squeal when she realizes that her bare pussy is exposed. The young babysitter stands there covering her bare pussy now.

"Darling, pick up those damn shorts!" Butch tells the confused young woman. He can't believe this girl is still going through with everything. He thought that maybe she would run out of here soon or smack his head and call him crazy. But nope, here she is, wearing only a tight bra and short cut off jean shorts like daisy dukes. Ass and pussy exposed for him to play and punish.

Jennifer squirms to get on her shorts over her hips. The men watch momentarily as they watch her ass squeeze into the tight clothes. Then quickly the men push her out of the home. She knew she couldn't run away because Butch had her phone and hasn't paid her yet. She didn't think this discipline thing would take long, he shouldn't be that mad over the whiskey.

All three step outside in dusk light. Jennifer is feeling flustered because she's exposing her tight body to everyone. Her bra is only a C cup holding her perky D's. Jennifer has been outgrowing some of her clothes and regrets at the moment not replacing this bra. They were standing in a mobile home street area with many trailer homes surrounding her. Jennifer's gazing at all the homes that might have someone looking at her. She couldn't believe she was suddenly outside and just then she's yelps. She groans when Butch yanks the jean shorts and pulls it far up her ass cheeks. Jennifer's young peachy ass jiggles in display as the jeans dig up into her butt.

"I said for you to pick up those fucking shorts!" Butch gets Jennifer's small shorts so far up her ass that most of her bottom is exposed and she has to stand on her tip toes as he wedgies her. Then he forcibly grabs her hand and begins walking to Harry's trailer home.

Jennifer is embarrassed and in shock to all of this. She wants to pull the shorts out of her behind. She wants to get her shirt back on. And she definitely doesn't want to expose herself to any more old men. But then they spot an old man unloading his groceries into his home.

Butch calls out to him. And they all approach. Jennifer is silent and mortified. She didn't want anymore encounters. Butch tells trembling dame to behave so he doesn't change his mind on getting her fired. Then, Butch asks if the old man would like a smack to her bottom. He obviously obliged and gave Jennifer's exposed bottom some hearty slaps. Butch orders her to bend over the parked car and she yelps to how hard he spanks her. Followed by a soft 'thanks sir' from Jennifer's pouty mouth. Next, they leave and finally make it into Harry's trailer home.

All three walk in the dusty trailer while Jennifer's rubbing her booty from the abuse. Jennifer starts dreading what may happen next, she's starting to flashback to her terrible embarrassing morning in the alley with a couple of bums. How they molested her, touched her body, and humiliated her throughout. The young woman stands there zoning out and hoping this won't turn into something like that.

More moments later.

Jennifer finds herself bent over from the waist with her face shoved in an old couch cushion. Her hands are on top of her head. Her humiliated body has legs slightly spaced apart and her ass in glorious round display. The jean shorts are digging right into Jennifer's ass crack and pussy lips.

Quivering in front of Butch and Harry, a red round tushy is swaying side to side, begging for more spanking. Red marks are clearly laid over her ass cheeks.

"See I'm glad you still have that paddle" Butch admires the work on Jennifer's butt and rubs his hand across it. For the last few minutes, the guys have been laying this paddle down on Jennifer's ass. "That thing smacks her real good" SMACK! He lays another one on her cheeks and enjoys Jennifer's moan of despair and how she bounces her butt.

The young babysitter is trying to keep her breathing normal. She feels so humiliated and so much pain from the paddle. Jennifer hates having her butt so exposed to these old men and now her ass is on fire. She's whimpers from the paddling but stays in position. Jennifer's regretting to agreeing to this idea of punishment. But she knew she did a dumb thing, so she also kind of thought Butch punishing her made sense.

Suddenly, there is a knock on the door. Harry opens it and in walks another old man, who whistles when he sees Jennifer's exposed butt. Her round behind jotting out in the air from the couch.

"Hey darling, this is Richard. He's the other one who, um put money into that er...whiskey you tried to ruin." Butch tells Jennifer while she keeps her embarrassing position of her face in the sofa and ass out bent over.

"Well umm...how much longer do I have to stay like this? Can I go now?" Jennifer tries to ask while faceplanting the sofa. She keeps shifting her feet, which gives great wiggles to her round behind. The men were talking to each other and Richard is having a big grin looking at their damsel's prized ass and pussy.

Then, Jennifer hears in her ear. "You're here 'til that ass get more beat red" Then Richard yanks her tiny jeans shorts down. The shorts land on the floor at Jennifer's feet. The new old man takes the chance to get a close eye view of her tight pussy and butthole, now exposed.

"Hey! What's going on here?!" She squeals and tries to stand up. But, Harry intercepts her and pushes her down on the couch cushion. She groans but reluctantly stays stuck in this position. Jennifer doesn't want to fight back because she knows she's outnumbered. She dumbly wonders what they want to do with her and her naked butt.

"Well, lets get on with it then." Butch then hands the medium leather paddle to Richard. "Have your way sir" Big smiles come across their faces like little teen boys.

Over the next few minutes, Richard enjoys using the paddle on the humiliated brunette. He landed many hard smacks on the young booty. Jennifer has no problem yelping into the cushion. It blocks most of her groans but the old geezers could still hear the sweet damsel's voice.

"Oh please! SPANK. Ow! I'm sorry! SPANK. Oh, so sorry! SPANK. Oh sir! Please. SPANK. Ah! It stings!" Jennifer says constantly as the paddle bounces off her perky bottom. She has never felt her butt on fire as much as this moment. Her ass is so hot and red. Jennifer hardly noticed how wet her pussy is, but the men sure noticed.

The other two already had there fun with Jennifer, before Richard showed up. So they just watched as Richard worked his tennis swing on Jennifer's big round butt. Harry is so happy to have this young damsel's ass receive a hard spanking in his home. He enjoys the jiggle in her ass from every smack on her sweet cheeks.

Richard turns the new exposed flesh of Jennifer's ass into a bright red burn. She's told to hold her position after Richard is finished with her. Face down, ass way up. Jennifer's bottom is on fire and she feels so completely humiliated to be spanked like a naughty little schoolgirl. She just wants to rub her butt and get away from these old grabby hands.

"Oh...ok...ok" Jennifer tries to find words. "So, my ass is on fire. Ow. I know umm...I fucked up. I am sorry! Please Butch, let me go now. My booty is stinging! You three spanked me good. Okay, I learned my lesson sir." She looks over her shoulder to make eye contact with Butch. But when she turns around she sees the men getting there shoes back on. Then even worse for Jennifer, Harry stands her up and starts pushing her out the house. She struggles to find something to say as she desperately covers her pussy and rubs an ass cheek.

Butch speaks to the nervous looking brunette. "Ok sweet red ass, we're going over to Richards, to finally get what we need to finish this." He slaps her bottom once more before he walks out the door.

"But before we go, I need a souvenir. This is going to stay here with me. SNAP." Harry closed in behind Jennifer. And with swift motion, his wrinkled hand popped off Jennifer's bra. And since it was a strapless bra, it came right off and scooped up by Harry.

"Hey! Oh my! What the fuck!" Jennifer rushes cupping her naked D-cup breasts. Then she hears the door slam shut and remembers she's now standing outside half naked. Wait, Jennifer looks down and realizes that her cut off jeans shorts are still around her ankles. "Oh fuck, my shorts!" Jennifer desperately tries to grab her little shorts with one hand. The other hand is stretched across her tits trying to contain her nipples.

Yet, Butch is waiting for her outside and grabs her free hand before Jennifer could actually get her shorts up. "Come on hold my hand. I don't want to bust a hip out here and end up looking stupid. Stupid like you." Butch grins and tells the others to hurry up.

Harry and Richard approach and still can't believe what's in front of them. A naked brunette bombshell trying to cover her naked body with one hand while arm linked with their good friend Butch. Something they haven't seen...in about twenty years.

"Whoa! B-but I'm naked. Let me please get my shorts on. Butch, hey! Where are we going? Ugh. Wait stop pulling me. Please. I'm like, completely naked out here." Jennifer pleads for anyone listening in the group.

"Don't worry, you'll be naked inside real soon. Hehe." Harry says aloud to Jennifer. She shivers at the thought. But she also hopes it's true so she can escape from public view.

The young babe is humiliated to be out displayed like this. She can't get her arm away from Butch. So with only one free arm she tries to cover her tits while having tight legs to hide her pussy. Unfortunately for the punished babysitter, her little jean shorts are making Jennifer take small steps. Since the guys didn't let her pick them up, the jean shorts have slowed her walk. Now, Jennifer is walking with a shuffle down the road. She looks like a humiliated slut. Harry and Richard are enjoying the sight of her perky round bottom jiggling and bouncing all naked. The red on her ass is quite obvious.

The dazed dame hears the shuffle of pebbles on the ground as she embarrassingly walks with Butch. His pace is slow enough for her to keep up but she wishes they try to move a little faster. Because Jennifer is frantically looking around the old folks homes, hoping no one else is watching her humiliation. She regrets agreeing to this old pervert's way of discipline. The dumb girl thought she would just get some spankings from an old timer and then apologize. Walking down this little road is beyond embarrassing for Jennifer. She still hates being in this kind of situation. She's naked with only one arm to cover her tits and has a very red ass. Plus she's shuffling down the road with her shorts around her ankles. The old men smile and occasionally slap the butt cheeks of the nervous brunette while they inch closer to Richard's trailer. Jennifer is dreading this night. She wanted to fall to the floor (but the rocks would hurt like hell), or she wanted to knee every geezer in the balls (but then what? Run home naked with no phone? Nope, can't do that).