The Bully Tutor (Patreon)

The story itself has been around a while but took me some time to settle on just how to write and pace it. Bullying’s wrong and all, but I try to keep the tone pretty lighthearted beyond some teasing I’d probably use in any of my other stories. It’s femdom at heart, but more pushy and controlling.

Molly had like 3 or 4 names I had to keep going back to edit. Originally I went really tomboy and called her Sam but that felt weird after a while. While the story’s been around a while in my head, it didn’t really spark until my fiance and I played Deltarune and I knew there was something to harvest from Susie the weird dinosaur bully girl. So here we are!

Jeff was old enough to recognize that the methods of Molly’s bullying were downright archaic. He had gone through middle school and high school being shoulder-checked to the ground, punched in the arm, stuffed into lockers and the anything else Molly could get away with (which felt like everything). She got in trouble now and then, but Jeff couldn’t bring himself to snitch on her. He imagined it would only make her angrier, removing the bitter playfulness that flavored her tormenting. It was to a point where he would strategically plan his routes and schedules in the hallways so he could avoid her attention. It didn’t always work, but it minimized his trouble.

Of course, school was always more than just that. Even with his contact with Molly kept at a minimum, he found himself struggling in U.S. History. His teacher was understanding and suggested for a tutor to meet him later in the week to help him prepare for the upcoming test. Jeff wasn’t about to flunk out of school, so he optimistically accepted. They would meet him that Friday night.

When the fateful night came around, Jeff had the house to himself. At his age, his parents didn’t mind leaving him on his own and they had felt like going out to dinner to celebrate dad’s promotion. Jeff just sat around with some snacks set out and his books ready until he heard the knock at the front door. He hurried to open it, smiling politely for a half second before it vanished from his face.

Molly was standing just outside the door with a notebook and her history textbook were under one arm in case there was any mistake what she was here for. She was tall for her age and a little stocky but had more noticeably gotten her breasts early. She had only kept growing until she was ahead of the game with her double-D’s that pushed at her t-shirt, tempting bait that would only lure victims in like a venus flytrap. She had boyishly short brown hair that curled at the edges, light freckles running across her nose where her uneven tan didn’t completely cover them. As some small consolation, her eyes went just as wide when she recognized Jeff as the other way around.

“Hi… Molly,” he managed quietly. Her nostrils flared as she took a deep breath.

“Hey,” she said in her husky voice. She glanced around the house briefly before her eyes locked back on him. It still made his blood run cold to meet her eyes. “So you’re fucking up in history?”

“Yea…” Jeff said like he was walking on thin ice.

“Figures,” she sighed. “You always were a dumbass. Look… they caught me fucking with the soda machine, so they’ve got me doing community service. That’s the only reason I’m here.” She gave him a glare that spelled out what she didn’t feel like saying in the open; it was the only reason she wasn’t making his life hell right now.

“So are you going to let me in or not?” Jeff realized he was blocking the door and swiftly stepped aside, letting Molly step into his house. She bumped her shoulder against his for good measure, her stocky build easily knocking him the last step out of her way. She threw her backpack onto the couch and dropped herself just as unceremoniously next to it. Jeff realized that left him with nowhere to sit but directly next to her. He moved in with some visible reluctance before she just grabbed him by the shirt. He flinched and expected the worst, but she just dragged him onto the sofa.

“Quit being a pussy and let’s get this over with,” she demanded.

Molly actually started to go over the recent classes and he was actually starting to believe she was serious. If this was her punishment, she might have been too worried about getting into worse trouble by messing with him. 

“So your test’s on the Civil War. That’s the easy stuff,” Molly laid out. “Bloody fights and the president gets shot. Crazy shit. So let’s start easy. Name me a Northern general from the war.”

Jeff took a deep breath to stall. He was always bad at names. “That’s… uh… general…” He was drawing a blank. Molly raised her eyes from her book to watch him expectantly, something that got his blood to run cold. He turned his book to face him, hoping to catch someone’s name in bold for something. He flipped through a couple pages rapidly before Molly grabbed him by the wrist.

“Whatcha doing there, loser?” she asked as the tingle ran up his spine.

Molly’s lips curled into her wolfish smile, baring the edges of her teeth. “You seriously don’t know.”

In a quick motion she was clearly used to, she snatched the book out of his hand and clapped it shut. She tossed it to the other side of the couch while she moved closer, mounting Jeff and pinning him to the arm of the couch. Her taller and heavier body easily kept him trapped.

“I thought you dorks were supposed to be smart,” she laughed, her chest hovering close enough to his face that Jeff couldn’t help but stare. “Come on. Give me a shot. Northern general.”

Jeff’s mind raced for any name he remembered from class. “Uh… Ford?”

“PFF! Seriously?” The aggressive tutor laughed and leaned into him, burying his face in her tits. “Ok, you’re going to need some motivation. Something you’ll really remember…” Molly’s smile widened as Jeff started to breathe heavier. Her crushing weight was one thing, but the thin fabric of her shirt over his mouth and nose forced him to breathe through her cleavage. He could smell the sweat on his old bully, something that triggers his survival instincts despite her not really hurting him in any way.

“C’mere. I’ve got a better idea.” She stood up suddenly, pulling on Jeff’s collar. She pushed the scrawnier boy onto his back, flattening him out on the couch. She wasted no time in letting him consider what was going on before she stepped over him and planted her ass into his face. Her curvy ass pushed against her jeans hard enough that his face could feel the difference between her round cheeks, her sock-clad feet curled back and resting next to his head.

“Grant, Chamberlain, McClellan, Sherman,” she rattled off. Jeff tried to ask what she meant but could barely get in a word before she pushed her weight back, sealing off his mouth beneath her butt. “They’re your important officers for the north. Now who were they?” She sat up to let him talk, perched on her knees to keep her ass hovering over his face menacingly.

“Uh, uh… Grant…” When she didn’t answer, he kept going. “Mc…Kraken…”

“McClellan!” she corrected as she slammed her butt back down. Jeff gave a miserable grunt as her cheeks swallowed up his face, leaving just his eyes to look up at her and recognize his punishment. It wasn’t as smelly as anyone would have told him about the dreaded bully, at least not through the denim. It was oddly pleasant with how soft she was, and the subtle head radiating off her hips. He tried to push at her cheeks but while it shifted and jiggled in his grip, she wasn’t budging.

“Grant, Chamberlain, McClellan, Sherman. Now give me a squeeze when you have an answer.” Jeff spent the next minute or two playing her punishing game, trying to ignore the dizziness and distracting pulse in his crotch. She wasn’t an ugly girl… sort of a tomboy but too curvy to complete the look. Being buried underneath her always came with some strange feelings, especially now that she wasn’t hurting him. In hindsight, she was more into embarrassing him that just beating him up… not that it wasn’t still awful to go through in the past.

Molly started with her hands planted stubbornly on her hips, but after popping up and down a few times, her hand was resting on his thigh. He prayed she didn’t notice the bulge in his pants as she went on quizzing him, idly shifting her weight to push her ass higher up his face. Jeff could feel the heat coming more distinctly as she lightly brushed her crotch right over his mouth. She was bent far enough forward that he could see the edges of her purple-pink panties riding up over the edge of her pants.

Once he’d finally given her a few correct answers, she sat back up. He gasped in some air as she pushed his legs out of the way and sat by his feet. “Nice job. Took you long enough,” she gloated. “You must like being stuck under me. Just like old times.”

“Yea. Ha ha,” Jeff muttered meekly, hoping his blush came across as him being short of breath from the smothering. Molly threw an arm over his shoulders, reeling him into her and smirking.

“I’m just having fun with you, dumbass. You’ll remember it. I promise. When that question comes up on the test, just remember staring at my ass for the last five minutes.” Jeff fought back a shiver at the fresh memory. “Come on. I got one more idea. We’re having a lightning round.”

“And what? You smack me for each wrong answer?” Jeff asked cautiously. Molly squeezed his shoulder firmly.

“That’d be fun, huh? But nah. You show up with bruises and this is all coming back to me. I’m not gonna hurt you, bitch. It’d be too easy.”

Molly grinned as she pulled him even closer, forcing him to sit in her lap. It was an awkward fit as he wasn’t that much shorter than her, but she didn’t seem to mind. In fact, she wrapped her arm around his neck. Not a full-on chokehold, but firm enough that he couldn’t squirm his way out. Her other hand reached around his front and lifted his shirt.

“Now get your cock out.”

“Wh-what?” Jeff blushed even harder.

“Take it out and start stroking. You’re not allowed to finish until you give me five right answers. Or are you too chicken about that little dick of yours?”

“I am not,” Jeff defended, even as his voice quivered. He took a deep breath before he did as she asked. A low chuckle teased his ear, making her breasts bounce against his back.

“Not bad for such a little guy,” she teased softly. “Now start jacking it.” Jeff felt the brief urge to say no… to squirm free or threaten to tell on her. But the way his cock throbbed, it didn’t feel like such a bad offer. Being held and intimidated by his bully like this was better than some of the alternatives. He held his pulsing erection and sighed at just how good it felt to relieve that building pressure.

“So… when was the battle of Fort Sumter?”

“I dunno. 18…60?” Jeff guessed.

“Close! But wrong.” She giggled in his ear while she glanced towards his slowly pumping hand. “Is that seriously how you jerk off?”

“Yea?” Jeff defended meekly.

“That’s slow as shit!” Molly laughed. “Try to put some actual muscle behind it.” Jeff awkwardly started to pump a little harder, following his tutor/bully’s instructions as best he could.

“Oh never mind! Just let me handle it. You work on remembering this shit.”

Molly pushed his arm aside and wrapped her hand around his erection. Jeff gave a short gasp as she squeezed harder than he tended to. It was shocking but not unpleasant. As her hand pumped from just short of his cockhead down into his balls, Jeff had barely shuddered by the time she was tugging back up, working him rapidly as she leaned her breasts into his back.

“Come on. You were close the first time. Don’t pussy out already, cuz if you cum, I’m adding five more answers until I stop. And I bet I can make you pop a whole lot, like it or not.”

Jeff blushed and took a deep breath as he shivered in her grasp. He couldn’t remember the real answer so he took another shot. “1861!” he blurted.

“There you go!” she praised in an uncharacteristically sweet voice that made it feel that much better. Jeff nearly lost his load from her unexpected praise alone, but he gulped and steeled himself. He’d overindulged enough to know he wouldn’t cum repeatedly without hurting himself, especially at the pace Molly was going.

“Alright, now name me two reasons that started the war.”

Jeff squirmed in her grip as she kept the questions coming. She didn’t let up on her stroking, but she’d snicker in his ear or tease him when he gave a wrong answer. She reached lower to lightly squeeze his balls or softly corkscrew her fingers around his cockhead but she never actually hurt him so much as she drove him crazy. He was so mind-numbingly sensitive that he could feel the trickle of his precum down his shaft and her hard nipples pushing against his back. He had to admit, she was certainly making the lesson memorable.

“Oh, uh… shit shit,” Jeff hissed under his breath as he squeezed the arm of the couch.

“Come onnnnn,” Molly purred in his ear. “Shut up and nut, pussy. I’m not ready to stop having fun with you yet.”

“No! No, I know this one,” he insisted. “It’s uh… Ford’s Theatre!” 

Molly scoffed as she ran her thumb up the length of his shaft. Jeff felt like his brain was fried from holding out so long and couldn’t take another second.

“Lucky guess,” she muttered before she bit into his earlobe. Another quick pump of her wrist got Jeff to cum all over her hand, shaking in her squeezing arm. She let out a hearty laugh as she held him steady and let his cum fall over her hand and thigh.

“Okay, that was worth it!” she cackled. “You make the stupidest squeak when you jizz! Is that every time, or am I just special?”

“Shut up,” Jeff mumbled, but he was too weary to form any real argument against her. He just slumped back in her lap as she wiped some of his cum on his shaft.

“So that must be it! You must jerk off to me every night.” It wasn’t true, but Jeff couldn’t guarantee it would stay untrue for long. Not after today.

“God, I can’t get that sad little squeak of yours out of my head!” Molly went on laughing as she pushed him out of her lap. “You cum like a fucking virgin, dude.”

“Um…”

Molly raised an eyebrow, but Jeff clammed up. He shifted his eyes away from hers.

“NO FUCKING WAY!” Molly’s eyes lit up as a wolfish grin crossed her face. She punched him in the arm, but in a much more sporting way than she would otherwise. “Are you serious?! Dead fucking serious!”

“Yea…”

“Fucking how!?” she laughed. “You’re a cute little nerd! You’re no jock, but some girls care about sissy little fuckbois, right.”

“It’s not funny,” Jeff grumbled, too distracted to put away his dick. He avoided looking at Molly but her snickering kept making him blush.

“Yea, you know what? It’s not.” After a couple seconds, something soft hit Jeff in the cheek. He looked up to see Molly’s dark red shirt resting on his shoulder. He looked over just as she was unbuckling her bra.

“It’s fucking sad is what it is. Come on. We’re fixing that.”

“As in…?” Jeff asked, squeezing her shirt. He could still feel the warmth from her body. She was a little chubby beneath her shirt, mostly around her arms and chest. It was soft in a way that was clearly solid beneath it. Clearly an outdoorsy tomboy rather than just an out of shape nerd. He stared mesmerized as she pulled down her pants and underwear in one pull, tossing her purple panties by his side. So close he could smell that mysterious musk of her crotch from there. Her bush was untended beyond the fact that her legs were neatly shaved, forming a dark brown veil between her thick thighs.

“As in let’s get you hard again so you can lose that v-card, pussy.” 

Molly didn’t wait for an invitation as she moved to the floor. She pulled his pants off entirely before brushing some hair from her face and sliding his dick into her mouth. Her lips and cheeks shifted to fit him inside her comfortably. She sucked and slurped without a hint of shame, no matter how tense and uptight Jeff was acting around her. It was hard to stay that way as she eagerly slid his soft cock around her mouth, almost playing with it as she slid it between her tongue and lips. Jeff started to breath heavily as she licked the cum off his shaft, forcing it to stay steady with one fist. The edges of her big tits rested on his knees as she aggressively sucked him off, slowly pulsing her cheeks to knead the slowly hardening dick around. She kept staring up at him, fearlessly gauging his reaction while remaining blindly confident in her work. She seemed to know what he wanted before he did.

There was finally a wet pop from her lips as she took him back out, leaving his spit-soaked shaft hard in her hand.

“Good enough. Let’s go.” Molly climbed back onto the couch and spread her legs as she flopped on her back.

“Like… you’re serious.” Molly glared at him.

“Look, there’s being a loser I can mess with, and then there’s just… pathetic! I can’t keep looking at you knowing a cute little dork like you never got any. Now stick it in so I can pop your cherry already.”

“Okay okay… you sure you want me on top, though?” She’d sat on him plenty of times before, and she didn’t seem the submissive type. Molly just snorted.

“If I were on top, I’d crush your scrawny ass. Now you taking me up on this or not?”

Jeff took a few steadying breaths before he crawled on top of her. Molly watched him like a hawk as he carefully slid inside her. Her bush tickled briefly but her lubricating spit and whatever juices she already had flowing let him slide right inside her pussy. He let out a long, soft sigh as he let it stay inside her, soaking in her warmth as she let out a short moan of her own.

“Good,” she muttered simply. She took his arms and adjusted them to brace more comfortably on the couch, pinned down near her head. It lowered his body enough that she could palm the back of his head, squeezing him against her breasts. They expanded out beneath him as they cushioned his landing and let him slide even deeper inside her. He started humping slowly, still a little winded by his endurance test a few minutes ago. Molly pulled his hair and got him to thrust harder, pushing deep and hard enough to get her to grunt in mild surprise. Her lips curled into a smile as she kept a grip on his head, pulling him into an aggressive kiss. Jeff wasn’t expecting his first real kiss to involve quite so much teeth to it, but it still worked in spurring on his humping. His increased pace got her soft but solid body wobbling beneath him, making her breasts and belly to bounce against his skin. It helped him keep something like a rhythm as he went on riding her, watching his schoolyard bully slowly shut her eyes and tense the muscles beneath that softness. She squeezed Jeff’s arms tightly right before he came inside her, not built to keep it going for long after her non-stop teasing. He shook violently as his legs gave out and he collapsed on top of her.

“Better, right?”

“Right,” he mumbled as his face rested against her tits. Molly snorted and scratched at his hair like he was a pathetic pet of hers. “So this was weird, right?”

“Nah. I’ve been thinkin’ about it for a while now,” Molly said as she stretched out beneath him like some massive jungle cat. “Good to get that out of your system. Next time, though, I’m not stopping until I cum.” Jeff snorted a short laugh as he slumped against her, but he paused as the thought sank in.

“Wait… so by ‘next time…”

“Are you kidding me?” Molly said with a grin. “You were like a total spaz when you were doing me. I gots to see that again, and it’s way more fun than chucking you into a trash can. Or did you want me to go back to that instead?”

“Well... no…” Jeff muttered, squeezing himself flat against her. It definitely beat any of her other punishments… if you counted being talked into fucking her a punishment. He certainly felt a lot better after he’d let himself go inside her. Way better than just masturbating.

“Great! I’ll grab you online next time we have one of our little dates. Meantime, you’ve got some shit to learn.”

Molly got dressed and went along with more conventional teaching methods from there, but he did end up crushing it on his next exam. With everything that had happened, he had no trouble remembering what happened that night (even if Civil War history was a footnote in all of it). The teacher was so pleased with the results that they ensured he was set up for another tutoring session next week.