Benji’s New Bully

 Cassy walked down the street that autumn day taking in the new season. Summer had come and passed, and where there were pool parties there was now pumpkin picking, and where there were bathing suits there were now hoodies. The hot air was cool and the green leaves were now red and yellow. Everywhere Cassy looked she could see fall - until she turned the corner and found a peculiar sight of Benji hanging up on a fence by his underwear. No sign of fall, just hang. 

Cassy started giggling as she walked up to Benji, who noticed her approaching and pouted. 

“Another day of hanging around, Benji?”

“Yeah, just living the dream,” he moaned. 

“How’d you get up there? Alice?”

“Yeah. Alice hung me up here a few hours ago before she left for Boston.”

“A few hours?? I’m surprised your underwear hasn’t ripped yet.”

“Well, they’re not exactly hooked on the fence like normal…”

Cassy peeked behind the fence and saw that Benji’s boxers were pulled through to the other side but wrapped in a knot around a baseball too big to fit through, leaving him trapped in midair with no sign of ripping. 

“Wow, that’s intense!” Cassy laughed. 

“Yeah. Alice said she wanted me to still be hanging up when she gets back.”

“When’s she coming back?”

“December.” Cassy paused and thought for a second. 

“December? That’s in 2 months! Well, have a good hang!” Cassy began walking away, waiting for the bait to be taken.

“Wait! Can you please get me down from here?!” Benji cried, taking the bait. Cassy turned and went back to Benji. 

“I could, but should I?” she asked, pushing him a bit, making him swing. 

“Please! I’ve been up here for 3 hours! This hurts!”

“Hmm… I dunno…” Cassy playfully swung Benji back and forth like a cat playing with a ball on a string. 

“Please I’m begging! She’s not coming back and they won’t rip!”

“Hmm… well if Alice is gone for 2 months that means you need a bully then to fill in for her, don’t you?”

“What? No I don’t.”

“Oh I think you do.”

“I don’t!”

“Really? Well I think you do. And if I let you down, then I’m your bully until Alice gets back.”

“Okay okay fine! Just please let me down, my butt crack is on fire.”

“Okay, baby boy.” Cassy grabbed Benji’s legs and began pulling down. Benji’s face contorted from the pain. 

“WAIT NO NOT LIKE THAT PLEASE!” he cried as Cassy pulled anyway. After a few seconds, his boxers ripped and Benji fell down on the ground. 

“OW FUCK!” he cried. 

“Say thank you, Benji.”

“Thank you…”

“Thank you who?”

“Thank you, m’am.” 

“Good boy. Now go home and get yourself back together. I’ll be over.”

“Huh? Be over when?”

“When I feel like it. Now go home or you’re going back up on that fence.”

“Yes m’am!” Benji cried, rushing off in fear, leaving his ripped boxers hanging from the fence and the other half sticking out of his pants. It wasn’t until he was home and out of that ripped pair of underwear, massaging lotion between his butt cheeks that it occurred to him - “what have I done?!”

Three days later, Benji came home from the store holding 2 bags of groceries. He entered his apartment and shut the door, and put the groceries down on the table, when Cassy’s voice rang out,

“About time you got home.” 

“AH!” Benji screamed in fright, not expecting her. 

Cassy walked into the kitchen from the living room, dressed in a white shirt and blue overalls to the petrified Benji in his black basketball shorts and grey T-shirt. 

“Hello, Benji.”

“How the fuck did you get in here?”

“Now is that any way to talk to me, your bully? Or ANY woman, for that matter?”

“No, how did you get in here?!”

“I have my ways. I told you I’d be coming to see you.”

“Yeah but,”

“I noticed you ignored my texts the last few days. Is that any way to treat me?”

“I.. I’ve been busy, and,”

“Mhm I bet. Too busy buying…” Cassy looked inside the bags Benji brought in. “…hot sauce, huh?”

“Listen Cassy, I-“

“Is that any way to address me?”

“I…. Listen, *m’am*,”

“You know, I don’t appreciate that attitude. You know we’re gonna have to do something about this, don’t you Benji?” Benji was in a bind. She was his bully, and he knew it. He sheepishly looked to the floor. 

“…yes, M’am.”

“Look up at me.” Benji lifted his head to look at Cassy, who put her finger under his chin and lifted his head up towards hers. 

“Tell me. Ask me for it.” Not breaking eye contact, Benji let out a squeaky little,

“Will you please punish me, M’am?”

“Yes, I will, you silly little boy.” Cassy took Benji by the hand and walked him into his living room. She had a big smile on her face; he had a grimace. 

Cassy stood in the center of the room and stood Benji up in front of her, and she looked him up and down, deciding what to do with him. 

“Hmmm… I have some ideas…” 

Cassy turned Benji around, lifted up the back of his shirt and saw the waistband of his blue boxers sticking out. She grabbed them with both hands and hoisted him up, lifting him off the ground by an inch or two.

“Ahhh! Ahhh!!” Benji groaned as Cassy wedgied him. 

“How are these Hanes treating you?” she asked, chuckling. 

“Ow ow ow!” Benji cried in response. As Cassy lifted him up a bit more, she realized they weren’t going very high. 

“Hmm… boxers are hard to wedgie. I probably can’t even get these over your head!” Cassy complained, still trying to pull Benji higher. 

“Thank god!” Benji exclaimed. Cassy narrowed her eyes and her nostrils flared. 

“Oh is that so?” She let go, letting Benji fall down to the ground. As Benji stood up, Cassy went to her bag that was on the couch and dug in before pulling out a pair of panties, grey with pink lines going across. “Perfect!” She held the panties out to Benji who was still pulling the boxers out of his ass. “Here, put these on.”

“What? I’m not putting your underwear on!”

“You really want to sass me, Benji? Do you want to make your predicament worse?”

“…fine, I’ll go put them on.”

“No, put them on right here.”

“What?! Are you serious?”

“Boy, you really aren’t well behaved at all. Come here, naughty boy.” Cassy took a seat on the couch and Benji walked over to her. “Turn around.” Benji did as he was told, turning his back to her. Cassy took the sides of Benji’s shorts and pulled them down, letting them fall to his ankles. She then took the sides of his still wedgied boxers and unrolled them, pulling them down to his ankles. 

“What a cute little bottom you have!” she giggled, giving his right cheek a little pinch. Benji whined. “Okay, step out of those now.” Benji did as he was told, stepping out of his shorts and underwear and kicking them to the side. Cassy took the panties and brought them down to Benji’s feet. “Step into these,” she commanded. Benji stepped in and Cassy lifted the panties up so they covered him up. “There we go, perfect in your little panties!”

“I don’t like wearing used underwear…”

“Hey, first of all they’re mine. Second of all they’re clean. Now let’s try this again.” 

Cassy stood up and wedgied Benji and the panties went right in snug between his cheeks. 

“Ow ow ouchhh!” Benji cried as again Cassy lifted him skyward. 

“Much better!” she laughed demonically as she stood up on the couch, lifting Benji up in the air by the panties. 

Benji kicked and flailed his legs, making it worse and tighter as Cassy lifted him up and up. She began doing hard, short tugs, yanking him up and up.  

“Ouch ouch ouch!” Benji cried as Cassy used her own panties to give his butt the business. 

After about 2 minutes of wedgie time, Cassy let go and got down off the couch. 

“Don’t pick that,” she warned. She took her seat on the couch once more and took Benji by the hand, taking him over her knees, his wedgied butt landing square in her lap. She began rubbing his exposed cheeks. “Look at this adorable tush! So cute but so white. We’re gonna have to do something about that, aren’t we, Benji?”

“…yes, M’am,” came the sheepish reply. 

Cassy took hold of Benji’s panty waistband with her left hand, pulling the panties as far as they could go and exposing his almost entire butt, which she began spanking with her right hand. 

Cassy began a rhythm of going back and forth giving Benji’s cheeks firm, open palm slaps. 

“Ow! Ow! Ow!” Benji yelled out with each smack. With each smack, Cassy gave the panties a tug, making Benji uncomfortable both on his cheeks and between his cheeks. 

“You know you deserve this for sassing me and being disrespectful, right Benji?”

“Ow! Yes m’am, ouch!”

After a few minutes, Cassy stopped. She began inspecting Benji’s cheeks - they were a light pink. Hardly punished. 

“Benji, I want you to stand up, go to the bathroom and get the brush, please.”

“Which brush?” 

“What do you mean?”

“I mean there’s the brush for my hair, my toothbrush, the brush I use in the shower…”

“In the shower? A bathbrush?! Perfect. Bring me that, now.” 

“Fuck,” Benji said, standing up and realizing he’d fucked himself. 

“What was that, young man? Are you being a potty mouth? Is that any way to speak to me?”

“No m’am, I…”

“I don’t think so. Let’s go.” Cassy stood up and grabbed Benji by the ear and began walking him to the bathroom. 

“Ow ow ow ow ow ow!” Benji cried from how hard she grabbed his ear. Once they were in the bathroom, Cassy stood him in front of the sink. Cassy turned on the sink, took the bar of soap that was on the sink and washed it under the water and turned it off. 

“Open your mouth and stick out your tongue,” Cassy commanded. Benji, knowing what was coming, cringed as he opened up. Cassy immediately stuck the bar of soap into his mouth and began scrubbing his tongue. Benji cringed and moaned as Cassy scrubbed his tongue clean. “This is to wash your dirty mouth so you never use such foul language at or around me or anyone. Do you understand, Benji?” Benji nodded.  After a few moments, Cassy held the soap between his teeth. “Bite down on the soap,” she instructed. Benji complied. Cassy then took a seat on the edge of the bathtub and pat her lap. Benji took his position over her lap once more, still biting the soap. Cassy reached into the shower and pulled the wooden bathbrush out and brought it to Benji’s exposed cheeks. Using the other hand to wedgie him again, she pressed the bathbrush against his butt. 

“You’re going to get 30 with this. It’s going to hurt. You’re to not let go of that soap, young man. If you do, the soap goes back in and we start over from 1 and go to 60. Do you understand?” Benji nodded, holding on tight. 

Cassy began spanking Benji with the bathbrush, doing hard smacks across the cheeks. Benji moaned and wailed, holding down to the soap for dear life, trying his hardest not to scream and cry as Cassy brought the terror down on his poor backside. Cassy hummed a jolly tune to herself as she worked, almost sadistically, as she used the bathbrush to make Benji’s cheeks go from pink to light red. Benji gripped the side of the tub as hard, trying to deal with the pain. After 20 smacks she stopped, giving Benji a second to breathe and deal with the pain she’d just inflicted. 

“The last 10 are going to be just on your sit spots. So hold on tight.” With her left hand she pulled up on Benji’s left cheek, exposing his poor sit spot, which immediately got 5 quick hits. 

“MMMPFHHH!!” Benji cried, holding as tight as he could to the soap, his eyes tearing. Cassy then lifted his right cheek, applying 5 hits to his right sit spot. Finally, she lay the bathbrush down and inspected his cheeks once more. His sit spots were pink and his cheeks were red. She put the back of her hand up to his cheeks and felt the warmth. 

“Nice and warm. Stand up, go to the sink.” Benji did as he was told, and Cassy stood alongside him. She took the soap out of his mouth and put it back on the sink. “How does it feel?”

“It hurts,” Benji sobbed. 

“I know it does, baby boy. But when you deserve punishment, it has to hurt. Now you rinse your mouth out with water and come join me again in the living room. Don’t pick your wedgie, and do NOT rub your butt. Do you understand?”

“Yes m’am…”

“Good. I’ll be waiting. Don’t be too long.” Cassy walked out to the living room again as Benji sobbed into the sink, pouring water in his mouth to rinse as he wiped tears from his eyes. 

A few minutes later, Benji rejoined Cassy in the living room, waddling in front the wedgie. He kept his hands behind his back, holding them at his waist. 

“How do you feel?” Cassy asked. 

“My butt hurts…”

“Good. You didn’t rub, did you?”

“No m’am.”

“Good. Now I noticed you brought home some hot sauce today. What’s that for?”

“For eating with chips.”

“I see. Well first we’re gonna do something else with it,” Cassy held up the hot sauce, opened. “Turn around.” Benji whined and turned around. Cassy pulled the back of his panties back, and poured the hot sauce down. After about 30 seconds of pouring, she stopped and put the bottle down and let the panties snap at Benji’s ass. “Now, let’s see what we can’t do here.” With that, Cassy began wedgieing Benji again, and he moaned again but more aggressively. “How’s that feel?” she laughed. 

“It burns!”

“I thought so!” Cassy began pulling harder and harder, the fabric and hot sauce rubbing up and down Benji’s butt crack making him groan and moan in pain. Cassy pulled as hard as she could, getting the waistband up to around Benji’s head. “I think we’re gonna do it!” she cheered. 

“Ugh…”

“I think we’re gonna get… an ATOMIC WEDGIE!” Cassy cheered, reaching the stretched out panties up and over Benji’s head, finally letting go and letting the waist band snap on to his forehead. “Hehe, nice hat, dork.” Benji stood kind of trying to get his footing, his butt crack in flames. 

“Ouch ouch ouch!” he cried. 

“This is amazing,” Cassy giggled, walking the poor Benji to the couch. “If you can, kneel on the couch.” Benji slowly kneeled on to the touch, the panties rubbing harder and tighter with each leg movement. 

“Owwwww…” he moaned as he knelt down, sticking his exposed red cheeks out.   

“Perfect….” Cassy went into her bag of toys and pulled out a leather strap. “How’s your crack?”

“It burns!” Benji whined. 

“Now let’s make your cheeks burn to match! 20 with the strap. Here we go.”

SLAP! 

“OW!”

SLAP!

“OUCHHH! Casssy please!”

SLAP! 

“AHHHH!”

Cassy began mercilessly strapping Benji, giving him 5-6 second breaks between hits to breathe and cry before giving him the next swat. 

After about a minute and a half, all 20 were given. Benji had red splotches across his ass, nice and hot. He moaned and cried from the pain. 

“This hurts this hurts!!” he cried. 

“Poor baby…” Cassy said, putting the strap down. “Stand up,” she instructed. Benji quickly stood up and Cassy pulled on the panties again, this time taking them off his forehead and letting them snap back over his head to his back. “Go ahead and take your panties off.” Benji gulped and took the moment to finally pick the wedgie out, and he let the hot sauce drenched panties fall down to his ankles before he stepped out of them. 

“Okay, bend over again and touch your toes,” Cassy instructed. Benji did as he was told, not wanting to upset her. “Now, I spoke with Alice yesterday. She told me some of the punishments she’s given to you before. Very funny, very cute stuff. But she did mention one thing she HASN’T done…” Cassy walked off to the kitchen. 

“Huh?” Benji asked. Cassy walked back into the kitchen holding a narrow wooden cane about 3 feet long. Benji’s eyes went wide and he began shaking his head no. “No. No!”

“Mhmm. She mentioned you’d never been caned and bestowed upon ME the honor to give you your first taste of it! Aren’t I lucky?!”

“No! I can’t take that!”

“Ahem, you little booger, you will take what I give you. Now bend over and touch your toes.” Benji let out a whine as he bent over and got into position. Cassy positioned the cane and rubbed it along his already sore cheeks, making him moan and cringe. “Since you’ve never taken this before, I’m going to just give you 10 strokes. It won’t be THAT intense, but it won’t be a walk in the park. And you stay in position or I start over and double it. Am I clear?”

“Yes m’am,” Benji let out, already starting to tear. Cassy gave the cane a light tap or two before swinging back and CRACK! against Benji’s ass. 

“OUCHHH!” Benji cried. Cassy put her left hand on the small of his back to keep him in position. 

“Good boy. 1/10th of the way there.” She stood back again and once again gave him the CRACK! of the cane. 

“OWWW FUCKK FUCK FUCK!” Benji cried, holding position as hard as he could. 

“What was that?!”

“I’m sorry I’m sorry it just really hurts!”

“It’s SUPPOSED to hurt, Benji. I’ll let that slide once. But curse again and I’m doubling the strokes and doing them harder. That is your first and final warning.”

Over the next 2 minutes, Cassy caned Benji, each time he let out a scream and cried, trying his best to stay in position and not curse. 

CRACK! The 10th stroke was implemented. Benji stayed in position as Cassy put the cane down and inspected the stripes on the middle and lower half of his butt cheeks, rubbing her pointer finger across the lines. 

“Poor sweet Benji…. I know you can be a good boy, with no sass or attitude or swearing, but sometimes you need my hand to help get you there. I’m your bully but I care about you, you know that right?”

“Yes m’am,” Benji cried, his ass on fire. 

“How’s your butt feel?”

“It burns…”

“How does your butt crack feel?”

“It burns…”

“Right. The hot sauce. But you had it coming. You had all this coming.” Benji kept sobbing, not answering.

“You’re sure your crack really burns? From hot sauce?”

“Yes…”

“Well we can check that…” Cassy walked off to the bathroom. She returned moments later with wet wipes… and a thermometer. She sat down on the couch and pat her lap. “Come on, come over.” Benji, still crying, got back over her lap. Cassy first took the wet wipe and wiped between his cheeks, getting the hot sauce out. Benji cringed, feeling violated - no one else had gone in there ever since he was a baby. But once she was done getting the hot sauce, Cassy spread his cheeks and slid the thermometer in!

“Ow! Hey!” he cried. 

“You said it burns, right? And you’re sobbing like a baby. Let’s see if the baby really has a temperature…” Cassy kept her thumb and pointer finger held on the thermometer, swirling it a bit. Benji cringed, having never had anything go in there before. After a moment or so it beeped and Cassy slowly took it out and read it - “98.4. No fever, you’re fine, baby boy.” She put the thermometer down on the table. 

“It still burns…” Benji moaned. 

“Well baby. I’ve got something for you. Stand up.” Benji stood up and Cassy stood up as well, going to her bag. She pulled out an adult diaper, as well as a bottle of powder. “If you’re gonna cry and whine like a little baby and act like a little baby… we’re gonna MAKE you a little baby.” Benji’s eyes went wide with horror and he began shaking his head no. 

“Mhm. Lay down on the floor on your back, now.” Benji slowly got down on the floor and laid down on his back. Cassy got down next to him on her knees. “Lift up your legs, all the way.” Benji hesitated before doing what he was told. Once his red, sore cheeks were exposed, Cassy poured some powder on them and rubbed the powder all along his sore cheeks and sit spots. Finally, she opened up the diaper and put it below him, bringing his legs down and beginning to diaper him. After a minute, Benji was diapered. 

“How’s it feel?”

“This is so embarrassing and uncomfortable…”

“But you look so cute, my little baby!” Cassy giggled, pinching Benji’s cheeks (the ones on his face for once). Benji moaned in embarrassment, his face almost as red as his butt. Cassy pulled a binky out of her bag and held it to his mouth. “Open up.” Against his better judgement, he opened up, and Cassy stuck the binky into his mouth and he began sucking like Maggie Simpson. Benji moaned, sucking on the binky in his diaper as Cassy laughed and fawned. 

“So cute, my little baby dork. Now let’s get you to bed.” Cassy walked the diapered Benji to his bed and he laid down. “Good boy. Now go to sleep.” Benji moaned and cried in response, which Cassy laughed off, tucking him into bed. Once he was tucked in, Cassy turned off the light. “I’ll be back tomorrow morning to change you. Sleep tight like a good baby!” and she shut the door.

Benji lay in his bed, sore and striped on his ass, his crack violated and burning from hot sauce and thermometers, and stuck in a diaper that stuck to his sore butt and made it sting more. This was the worst day of his life and he’d never felt more violated, pained, humiliated and upset. And from the wedgie to the diaper and all the pain and degradation in between… he fucking loved it.