Hiring the Bully

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
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TheMilkman
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Hiring the Bully

Post by TheMilkman »

It was a tough decision but it had to be done. He was unruly and needed to be taught a lesson. But she just couldn't do it herself, so she made the call.

This was a crisis situation. She had second guesses but it wasn't enough for her to back out. With a knock on the door she let him in. She almost couldn't believe how he was dressed. A leather jacket and tank top was while for a thirteen year old. And his little shorts I mean come on what is going through this kids head. As they sat down across from each other Kathy leaned forward readjusting her seat only for the obvious to come forward. Damien's eyes were fixated forward on the low hanging fruit. With a bit of blush Kathy cover her tank top covering the exposure of her photo.

"Oh sorry I didn't realize the kind of shirt I was wearing." She tugged on her clev trying to pull herself together. "This was a bad idea." With the tip of her finger between her teeth she tried to pull back.

"Relax, please, don't trouble yourself for my sake, I'm here to solve a problem of your's." She knew what she had to do and just nodded her head. "You said over the phone he needs to be taught a lesson to get him straightened out?" Again she just nodded. It goes against every code as a mother but he left her with no choice.

"I just want him to listen to me." It was as if tears wanted to come out. Damien just moved next to her.

"Yeah I know, let it all out, trust me he's gonna listen to you after this." He just rubbed her back slowly.

"I mean you are the professional after all." He just pulled her chin up.

"I've been doing this for years now let me see that smile." She did as instructed letting him see her warm up.

"Is it gonna hurt?" Damien had to be honest with her.

"Only emotionally, probably gonna scar him for life but he needs to understand your the boss around here." Finally she could contain herself.

"How embarrassing does it have to be?" She just stood trying to get some distance.

"If we want this to work it has to be extreme, he has to know never to talk back to you again." There was a pause as she turned away. "So I need to know if there is any dirt you got on him, his biggest fear, an embarrassing story, you know something." She hesitated before reaching behind the couch. What was in her hand when she pulled herself upright caught Damien's eyes as they widened. The word diary was front facing with a pink cover.

"If I do this I can never go back." Damien couldn't take his eyes off the book. "I'd be a monster to let anyone read this, especially someone of your reputation." Damien had to come up with words fast. "So I won't." Damien stood ready to protest something he didn't need to. "I'm just gonna leave the book right here and go into the other room." And like that she was gone. Without hesitation he pulled open the book as his eyes danced across the words with chuckles under his breath.

The research began...

With his feet to the grind Jackson slid his board across the curb before flipping it into the air catching it. With his smooth walk be hopped up the stairs. The door was locked. No biggie he thought as he turned to the side combing his hair back in the window. He jumped the side railing as he popped open the gate to the side yard. As Jackson cut through the grass to the back porch something hit his ears. It was the biggest slurp he had ever heard. His ears helped his eyes track it as he narrowed in on the pool. He just watched the monstrous lips of Damien slurp through a bendy straw, floating on a floaty in the middle of the pool as care free as could be. Adding to the care free was his basic swim trunks and lack of shirt covering his chest.

Jackson almost didn't know what to say. Was his mom really that desperate for money she was renting it out to the local rebels. This was a good question for his mom. As Jackson turned to the sliding glass door it opened. Count it, four beautiful girls met his gaze as they left the house in swimsuits. Let's go down the list.

Tall blonde in a two piece,a long brown hair with thick hips in long shorts, a very pale redhead in a pokedot bikini, and a petite girl dressed in only a tank top and panties.

Oh Jackson knew them. One grade above him. Highschool girls. It was a dream come true. Jackson wasn't sure exactly what was going on but he liked it. The girls just giggled as they walked by him. He found himself in a trace until his mother stepped outside with drinks for the girls. Putting his tongue back in his mouth he tried to shake off the nerves.

"Oh sweetheart." Kathy spoke with remorse in her breath as she turned to her son. Jackson was concerned about her tone but basically ignored it as he reached for a drink only for all of them to be taken. Kathy lowered her tray as she tried to find the words. "I really wish you hadn't come straight home today." With her hand on his shoulder she consoled him. Confused, Jackson just looked past her at the beautiful women.

"Kathy remember what we talked about!" Damien's force caught a lot of attention as everyone turned to him. The girls gently waved as Kathy pulled herself straight.

"Right, I must remain strong." Kathy took the pose of a marching army, almost like she was taking orders. Confused was an understatement, Jackson had no idea what was going on. She just stood stiff flipping around. "Jackson you have been misbehaving and I think it's about time I make you listen to me!" With a scratch of his head he just kept watching her. "So with my hired help you will be taught a lesson!" It was finally starting to make sense. This all seemed pretty foolish so foolish indeed that Jackson couldn't stop himself from laughing.

"So you hired this punk to what, beat me up, in front of these girls?" Jackson was not afraid of Damien, not when his was confident in his abilities of swinging his skateboard around. When he beats up this bully in front of all these girls he'll be the talk of highschool before he even gets there.

"I wish it were so easy." Kathy looked like she could faint as she spoke. She fell to her knees as she grabbed her son's shoulders. "I'm sorry but you leave me no choice, to insure I'm done dealing with your awful shenanigans your going to be stripped of your dignity in front of a pear along with these girls an age above you." Kathy just hugged him tight as he tried to process these words.

"What are you saying?" Jackson asked as he pulled back making eye contact with her.

"She means you're gonna take your pants off for us!" Damien yelled from his comfy floaty. With his eyes locked on his mother's they both dropped to his shorts. Without warning silence broke out. As he looked up all the girls playful eyes watched on as they sipped their sodas. Suddenly his mind jumped to another moment in time.

Jackson stood safely behind a fence placed between two missing boards. With a turn to the left or right he was visible but on his side he couldn't be seen. It was those same girls on the other side playing in a sprinkler as they tossed water balloons at each other. Jackson couldn't help but get excited watching them but what would be even more exciting was if they saw him naked. Impossible really, that would be embarrassing and insane for a scenario like that to happen. But they couldn't see him so they couldn't know he was naked and because of that they wouldn't see him shaking his weenie in the fresh breeze.

Suddenly this felt just like that moment. Had to just be a coincidence of course because the only person who knew that story was the pages of his diary. Nonsense he thought, this was all just a ruse.

"Woah good one Mom you had me going there for a second." Jackson laughed it off as he wiped a joyful tear off his face. The silence only seemed to grow as the girls continued to suck with their eyes fixated on his shorts.

"A man in denial." Damien's words came with a head shake as he paddled himself to the edge of the pool. Jackson remained calm as everything just kept happening around him.

"Thank you girls so much for coming." Kathy turned as she expressed how thankful she was they all came. "It just means so much to me." With their cups on the patio table one of them spoke up.

"Our pleasure, when Damian told us the severity of the situation we hurried right over." The girl with the baggy shorts pulled her hands together as she raised herself up on her toes happy to help.

"It's just so awful the way he treats you." The redhead spoke up quickly with a pouty face. Ok now this was going to far.

"Alright jokes over, Mom I want these people gone!" His voice boomed but not a single person paid any attention to him. The girls just huddle together in hushed tones.

"I don't see how you put up with him."

"He deserves a good spanking."

"I think he needs some extra attention."

Just as Jackson was starting to make out what they were saying Damien came up behind the girls throwing his arm around them.

"Ladies relax, your guests here just get ready to enjoy the show." With the ease of his words the girls relaxed.

"Right thanks Damien." One of them pipped up.

"Yeah it's good Ms. Kathy here paid for quality service." Another sweet voice called out.

"I sure did, I mean look at this one girls." Kathy just leaned forward pulling on Damien's chin as she admired him. "He's so adorable you all might just eat him up." The girls laughed as they all blushed looking at Damien.

"Hello?!?" With anger on his lips Jackson pulled out his words trying to grab hold of the situation. Everyone turned as Damien pulled back eyeing his job.

"Oh right sorry Jacky boy." Damien walked around the girls as he moved closer to his target. "Don't worry we didn't forget about you, shows about to start." Jackson just gripped his pants hard as he dropped his skateboard. Everything seemed to go in slow motion as the mother figure started making her way to the back door. "Ms. Kathy where you going, your not gonna wanna miss this." She stopped just at the door as she turned back.

"Oh I'm sure it will be a hoot but I don't think I have the stomach to watch." She looked back at her son with worry in her eyes as she grabbed the handle of the door.

"What did I do? What do I do?" Jackson's words slowly rolled off his tongue as the girls started giggling. With a crunch of his knuckles Damien moved in close.

"Take off your pants." Like a farmer sneaking up on a greased hog Damien moved in close mouthing either his intent or his intent for Jackson.

"Wait wait wait!" With panic in his voice Jackson threw up his hands trying to stop the situation in its tracks. Everyone paused their expressions. The girls had the cheekiest smiles as they just watched everything unfold. "I understand, I'm being punished for my behavior, just give me a moment." Kathy paused with her hand on the door as she watched everything in the reflection of the window. With his hands floating above his waistband the pressure was on.

"We're waiting," Damien said, through the giggles of the women. Jackson grabbed his shorts as all eyes looked on. With one fell swoop he dropped his shorts to the floor. In full display everyone saw the white exterior with a blue trim. He just kept his eyes closed listening to the reactions.

"Huh oh my."

"Look girls."

"Hehe."

The girls were just beside themselves giggling over the sight in front of him.

"Nice underpants." The girls burst into fits of laughter as one of them pointed out the obvious attraction in front of them. Jackson underwear were as expected a nice white pair of tighty whities. Damien just whistled enjoying the show in front of him. The laughter slightly erupted into more fits of giggles as Jackson turned to his mother showing off his rear end to the small crowd.

"Alright I'm sorry I'll try to be better for you mother." As he pleaded his case the girls just lifted their hands pretending to squish and squeeze the tightly packed tush tucked away in the underwear. Kathy bit the tip of her finger before she turned around. Kathy kneeled down putting her hand on his shoulder.

"Son you are my everything, I care about you deeply, you're so smart and handsome and I know you'll do such great things." Jackson just smiled listening to her. "But I've already paid for the full package." With a kiss on his cheek and pinch of the other Kathy looked into his eyes with passion and comfort. As Jackson tried to process her words Damien threw his arm around him.

"Don't worry Ms. Kathy I'll make sure Mr. Underpants here changes his name to Mr. Nudiepants." Jackson couldn't help but laugh uncomfortably until reality set in. As he froze in place everything around him kept moving.

"Oh Ms. Kathy, could we get a refill before the underwear comes off?" One of the girls wiggled her cup before it was taken by Kathy.

"Mom!" Jackson pleaded but she ignored him. "Mom!" She just took the cups inside. As Jackson reached for the door a hand quickly grabbed the back of his underwear. Just as his feet started to lift off the ground the sliding door opened back up. Everything seemed to freeze as drinks were handed out. The girls happily took sips from their straws as they watched on in excitement.

"Don't mind me dears carry on." With her final words Kathy closed the door behind her heading into the house. With the strength of a thousand men Damien pulled Jackson up off his feet as he turned him to face the girls. With the shear strength of men he pulled hard on the underwear bouncing Jackson up and down. The giggles and laughter filled Jackson's ears as he hung on for dear life.

"What are you waiting for?" One of the girls pipped up. "Just yank down his underwear." The girls seemed to be more impatient then Jackson was. But Damien seemed to have other plans as he pulled the waistband up high almost over his head.

"Not gonna happen, I like to work for my money." Damien just wrenched the underwear up high pulling it far into Jackson's butt crack. "Besides, he's got insurance on these underpants, and I don't mind it coming out of my pay." On his tiptoes Jackson held on for dear life. There was no way to know how much worse it could get. And then suddenly Damien just let go. The elastic underwear snapped back into place as a loud reverberating smack slammed into his butt cheeks. His feet became flat as everything seemed to relax.

"Wooh." With a sigh of relief Jackson relaxed his body letting everything sag, especially his underwear. With a good slouch Jackson just let his mind relax only for the stretched out underwear to do the same. Just like that the underwear became all slack and dropped right to the ground. The girls all pulled their heads up as their eyes widened looking down. Jackson was so relieved he wasn't even focused on what was going on. All the girls just covered their mouths as Damien moved in close.

"How you feeling?" The words of the bully rang loud in his ear but didn't bring him to the realization of the situation just yet.

"So good, I thought for a second there you were gonna rip them right off." Denial was no just a river in Egypt in fact it was a river right here, a river of complete and total denial. Damien couldn't stop himself from laughing as he grabbed Jackson by the hips.

"No chance of that since they are on the floor." Suddenly Jackson's ignorant stare looked down as his eyes landed on his underwear cradled around his feet. The hushed giggles of the girls pulled his eyes up as his hips started rotating back and forth. "Check it out girls, his little peeny wants to wave hi." With the fits of laughter back in full force Jackson could feel this blood pumping quick. The girls all waved high back to it with a collective "Hi" from their voices. Jackson just dropped his hands over his crotch covering up his embarrassment as much as he could.

"That's it I promise to never be mean to my mom ever again." With his words outspoken he just pinched his knees together shaking embarrassingly.

"You promise?" Damien asked grabbing his shoulders as he spoke into his ear.

"I promise!" Jackson yelled hopping on his feet.

"That's all I wanted to hear." His mother's voice came close as she hugged him from behind. This experience assured Jackson he would never talk back to her again. "Ok I'm done embarrassing you in front of all these girls." Jackson just turned hugging his mother before she spoke again. "Damien?" She spoke his name as a question leaving so much confusion in Jackson as he pulled back. Damien just pulled a wad of cash out of his shorts as he slammed it down in her hands. With his eyes crossed he watched his mother count the money. "Yep it's all here," she said stacking it nearly on the table. "So what will it be then?" The confusion only seemed to linger as they continued.

"I'm thinking Christmas card or yearbook photo, what do you think girls?" Damien's words brought action as Jackson watched all the girls pull out camera's in the reflection of the glass door.

"Mom!" Jackson's word hit nobody as his mother spoke.

"Well would you look at that I made all my money back." Her words hit hard as she smashed the money into the cleavage of her shirt. With their cameras raised all the girls spoke at once.

"Calander!" The flashes started to begin as Jackson started running around the backyard trying to avoid cameras. Like violent paparazzi the girls snapped a picture of every angle they could chasing him around the yard.
Ashley cruxley
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Re: Hiring the Bully

Post by Ashley cruxley »

Pretty enjoyable but I doubt Jackson will keep his promise for long
NickTwisp
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Re: Hiring the Bully

Post by NickTwisp »

Ashley cruxley wrote: Sat Aug 15, 2026 5:12 am Pretty enjoyable but I doubt Jackson will keep his promise for long

Agree but am somewhat confused as to how the bully was physically able to force Jackson to take off his pants and eventually underwear, too. Seems like they were about the same age and Damien was not depicted as being a larger, stronger guy.
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