Here's a little Headmaster Arc thing made possible thanks to Kcid4229.

Enjoy.

Jaune was staring at his worst nemesis across all of time and space. Blue eyes bore into molten gold as a grin split her face and his hands clenched preparing for the worst. A slim and feminine hand reached out in front of him and he sucked in a breath. Jaune had his fate sealed as the piece settled into its final resting place.

"Checkmate."

"NOOOOOOOOOOOO!"

Glynda barged in panting and dropping the papers ready for a fight. Her eyes scanned the room for intruders but only found a motherly smile from Kali and a depressed Jaune as he lost yet another round of chess. The blonde professor let out a disappointed sigh and straightened her stance.

"Mrs. Belladonna, I assume he hasn't improved?" She had been hoping that chess would help Jaune improve his ability to read situations past the immediate future and thus make him a better leader. So far all of her hints had been ignored much to her displeasure.

"Not at all! Still as easy to read as a children's book!" The cheery tone in her voice did nothing to soften the blow to Jaune's gut.

"Thank you for today, perhaps tomorrow?" The headmistress opened the door as Kali stood.

"Perhaps, farewell Jaune! Just practice what I told you and you'll get better." Kali softly patted his head which made the blonde feel slightly better.

"Yes ma'am." As Kali left the room Jaunes shoulders sagged until he looked at the board again and began studying it intently. That was up to the point a crop slammed down onto the board but surprisingly none of the pieces moved. If one looked close enough they might see from them… shivering?

"Jaune! We have to work on how you present yourself!" The confusion was clearly written on his face. Glynda turned and walked a few steps, and before Jaune could fully appreciate how tight her skirt was she turned back around and fixed him with a stern glare. "Look at me, how I stand, how I project an air of confidence. Even if I don't feel confident in the situation, my projected confidence will allow others around me to respect the decisions I make and follow my lead." Jaune was starting to understand as he slowly stood and nodded his head. A desire slowly building in his gut. Glynda closed her eyes as she continued.

"If you make others feel your confidence you can then even do something outrageous but if it works, then others will follow. You've done this many times in the past but it has been blind luck. You need to learn to channel it and control it." She didn't know Jaune was right next to her until his lips were pressed against hers. A muffled squeak of surprise tried to escape her lips only to be swallowed by Jaune's. One of his hands gently wrapped around to the back of her head while the other found the small of her back. She put her hands on Jaune's chest to push him back but her resolve weakened when she felt the muscles under his shirt. H-had he been working out?!

Suddenly Glynda found herself falling backward on a bed as Jaune stared at her lustfully. This was not how she planned this night going. She saw Jaune begin to strip and got a good look at his body, he had indeed been working out! The headmaster leaned over and planted another kiss on her lips but this time she was aware and pushed into the kiss surprising him. Glynda's hands snaked around his body drawing him close before switching positions so Jaune was on the bed with Glynda holding him down with an authoritative foot to the chest as she panted to catch her breath.

"V-very good Jaune, that's the confidence you need at all times. Now wait right there and you'll get your reward." Glynda smirked as Jaune nodded. The dressed blonde turned and sway her hips teasingly as she walked and turned the corner.

Jaune lay on the bed excited that it worked! It looked as if a little confidence did indeed go a long way. He shifted himself further on the bed as Glynda rounded the corner as he found himself picking his jaw off the ground. Her clothes left little to the imagination, the outfit she wore now made Jaune's rock hard cock almost painful.

Glynda stood there with her crop gently smacking against her free hand, she still had her glasses covering her lust-filled green eyes while the black see-through top barely covered her generous breasts. Jaune's gaze drifted lower drinking in every detail as he saw a 7-inch strap-on, leading to creamy smooth skin that bled into leather thigh-high boots. His eyes were mesmerized by how thicc Glynda actually was, not that he would say that to her outside the bedroom.

Glynda walked closer, one step in front of the other, making sure to swing her hips with each step that carried her at a tantalizingly slow pace. Suddenly Jaune felt the crop smack against his exposed thigh muscles, and while there was a small pain he got very excited from it, especially when he saw the look in Glynda's eyes and the smile on her face. Glynda leaned down to Jaune's ear while tracing a small circle on his side with the leather crop.

"You like that?" A single nod from the man.

SMACK

"You want more?" More nodding as he hissed.

SMACK

Jaune let out moan after moan as repeatedly Glynda whipped him with the crop. Eventually, he found himself on his hands and knees with Glynda behind him slowly stroking the strap-on aimed at his tight back door. Glynda pushed forward at the same time Jaune grew impatient and pushed back. The closet dominatrix pulled back and whipped her boss again. Jaune whined as he let her have control. He could feel the cold from the lube touch his skin and Glynda's hands were on his hips. As she pushed forward Jaune felt himself falling face-first into the bed before being lifted up and suspended mid-air.

Jaune opened his eyes to find himself fully clothed with a huge erection being suspended in a purple aura and an angry Glynda standing below him. "Good morning headmaster." She didn't seem pleased to hear that he was moaning her name in his sleep, not that he knew that. Jaune blushed at being caught with morning wood while Glynda blushed as certain thoughts raced through her mind. She wondered what he had been dreaming about with her, and wondered if he would have the courage to act on them.

"G-good morning Glynda." He caught the blush on her face before she turned back to him with her usual stoic mask on.

"Time to get the day started, we have lots of paperwork to do so get dressed." She released her hold on him and he tumbled down straight towards the floor. As his face was about to meet bare wood, his bed suddenly slid underneath him and he fell into it with a soft thump. Glynda softly smiled at him as she closed the door. Jaune came out a few minutes later after getting dressed, and fixing his issue with morning wood.

He greeted the staff as he sat down for a cup of coffee that slid in front of him thanks to a friendly smiling Neo. Something about this day was already feeling off. The day continued this theme of being weird with absolutely no trouble coming from either Peter or Oobleck, Neo actually taking time to put the ice cream away, Sienna and Blake getting along marvelously, Kali not pestering him and instead sitting him down for a drink and friendly chat... the strangest of all was Winter not throwing around another crazy theory that he was somehow a criminal bent on remnants destruction. Beacon was about to face the apocalypse and Jaune was on edge for it.

As the headmaster entered his office he saw Glynda sitting behind his desk scribbling away furiously, clearly frustrated at something. He took a quick glance while she was distracted but couldn't make out what was on the paper outside of smudges.

"Good afternoon Glynda."

The simple greeting caused the witch to jump a full foot in the air like a startled cat.

"Ja- Headmaster! What are you doing in my office?!" Jaune curiously looked around and it was, in fact, HIS office not hers.

"You do realize this is my office, not yours?" He took a sip of coffee, oh so sweet and merciful liquid nerve relaxer from the gods. She spun her head to her right then did a full turn in the opposite direction before slowly turning back to a smiling Jaune with a sheepish smile.

"It seems I am in the wrong office please forgive me." Jaune chuckled a bit before taking another sip of coffee.

"Not a problem. Do you need me to help you back to your office? I don't mind if you want to use my desk but if Sienna or Kail saw this they'd get the wrong idea." Glynda had her head hung low and mumbled something.

"Glynda?" Jaune was worried that she might snap. If she did, who would help him run beacon?! Being honest, he didn't do much, it was all Glynda who kept everything running and in order. Suddenly her head snapped up as she stood staring at him with a heavy blush on her face.

"Headma- Jaune, we need to talk." Jaune, for his credit, was a whirling mess of emotions on the inside. Confusion mixed with worry and anxiety flooded him as he rapidly started filtering through the last six months trying to find where exactly he fucked up. When a woman called you out to 'talk' it wasn't talking, she was about to blow her top and vent every little frustration directly at you. The only hope Jaune had was figuring it out.

Glynda didn't do mad, she didn't lose her cool, she calmly ordered everything and made sure the world was balanced on a fine thread as it demanded of her. At least that's what the world saw, in reality she was a bundle of nerves and it was an honest surprise she hadn't ripped her hair out from working with Peter all these years.

The blonde witch stood there, her shoulder slightly shaking for a minute until she took a deep breath and calmed herself. She strode forward with a look in her eyes that had Jaune backpedaling quickly. Glynda didn't stop and neither did Jaune till his back hit a wall and the angry woman glared up at him.

"Jaune, do you have any idea how hard I work every day?" He rapidly nodded his head as he did indeed know what she sacrificed to ensure the running of the academy.

"Do you know how frustrating it can be?" He thought about this for a second, between Kali, Sienna, Blake, team RWBY, Pyrrha, the rest of team RVVN, Neo... he nodded quickly as she tapped her foot. Glynda's shoulder sagged and she rested her head on Jaune's chest. He grew even more worried when she brought a hand up and placed it beside her head on his chest.

"Do you know how lonely it is?" Jaune furrowed his brow at first but then a realization hit him as hard as Neo during training. His heart thumped wildly, his stomach felt light and his cheeks heated up quickly as Glynda sighed.

"Didn't you find it weird that everything was perfect today? Nothing went wrong, Neo didn't cause a fuss, Blake was well behaved, no loose Grimm from Peter's class, even Roman Torchwick behaved himself." She chuckled at that and everything started clicking for Jaune. His eyes drifted over to where Glynda had been seated and spotted a calendar. One date in particular, today, had hearts around it like a school girl's mark. Was that Glynda's? Her eyes followed his and her blush grew as she pressed her body closer.

"You know what day today is?" Again he wracked his brain trying to figure it out. Glynda could tell he was struggling as she softly chuckled.

"It's been a whole year. Care to live in the past for today?" Jaune swore he felt his heart stop at her words. So uncharacteristic of her, she'd been dodging the advances for so long he thought about giving up. He slowly brought his arms up and rested his hands on her back and hugged her tightly. She'd done so much to ensure that this moment would happen, it would be rude to not reward her efforts. He'd have to put more effort in if he wanted Glynda in the future. She made that abundantly clear.

The beautiful witch was looking up at him with misty eyes and Jaune brought his head down till their lips connected. Glynda grabbed Jaune's shirt and deepened the kiss as his tongue traced across her thin lips, begging for entrance. Her lips parted and tongues battled for dominance, it was a show on Glynda's part as she gave ground letting Jaune take control as she led them to his bedroom. Before disappearing behind the door she broke away for some air which Jaune took as an opportunity to attack her neck causing her to gasp. She glanced out the door for a moment and flashed a thumbs up to the six pairs of eyes watching before shoving the headmaster in the room.

The group all quietly cheered as the day had gone perfectly and Glynda could finally relax a bit. She'd been on them for weeks about today and threatened everyone with a punishment worse than Salem's imagination if they screwed up.

Back in the room, Glynda sat Jaune down on her bed and had to hide her smirk by letting down her hair. The bun burst, sending hair in every direction before falling perfectly to hide most of her features. It wasn't often she let it down. She walked over to Jaune with a swing in her hips as her slim fingers undid the buttons to her top and slide it off her curvy frame. She leaned forward, letting her barely covered breasts slightly swing in the headmaster's face. One hand came up to cup Jaune's cheek, tilting his head back. Their lips mere inches from each other, and as blue eyes meet green, Jaune saw the raw hunger that Glynda normally kept hidden so well.

"Lay down on the bed and wait for me to freshen up will you?" A simple suggestion, but the tone she used gave the words more of a commanding tone rather than a suggestive one. Her hand slid away, helping him down on the bed and she disappeared behind a door.

Jaune couldn't get his clothes off fast enough. As he flung the last piece of cloth off his body he lay naked on the bed as Glynda rounded the corner in the same state of dress as himself. Jaune shivered at the pure sexiness his fellow blonde radiated. He wondered why Jinn didn't have more counseling sessions with students confessing their love of the terrifying teacher. He also realized he just answered his own question.

"I have something special in mind for tonight Jaune. Mind indulging me this once?" Jaune nodded and if his twitching cock was anything to go by then he was looking forward to it. Glynda smiled and reached under her bed pulling out a blindfold.

"Put this on for me will you?" Again the silky smooth tones made argument impossible as Jaune gingerly took the cloth and secured it around his eyes. Some rustling from Glynda's direction followed by a few moans, which got him thinking and his dick twitching led to her voice coming forth again.

"You can take it off now." Jaune slowly did and his jaw fell open. Glynda was wiggling her hips, waving a ten-inch long strap-on in the air. His dick stood at full attention and his legs spread, more than willing to submit and accept Glynda's toy.

A pink tongue flicked out briefly to wet her lips as she swayed her hips, closing the distance between them. Her hand started their journey at her thighs slowly trailing up. Just the fingertips made contact with her flawless skin as she passed the plastic cock. She visibly shivered as she tickled herself on her sides and ended with cupping her perky breasts, playing with the nipples.

"Does this excite you Jaune?" Her wispy voice barely above a whisper. Jaune suppressed a shiver and slowly nodded. Glynda's hands followed the dangerous curves of her body downward but blue eyes could only focus on the object that gently bounced with each step. Jaune's eyes met Glynda's lust-filled emerald orbs as the plastic cock fixed to her hips was almost touching his wet lips.

"Go ahead, we both know you want to." A breath was inhaled while his lips parted just enough to slowly wrap around the toy. Glynda's eyes closed as she suppressed a moan. The toy extended both ways, meaning that any movement Jaune caused on his end moved the plastic cock currently inside the witch's snatch.

She hadn't been planning this. Not at all.

Her eyes fluttered open as the toy was moving more now. When her vision fully focused she could see Jaune dutifully working on lubing up half the toy with a bit of effort. He seemed to be into this as much as she was, making her question how long he had wanted it. Slender hands weaved through his blonde locks as a slow smile spread across her face. She pulled his hair and leaned back till their eyes met. A silent question passed between them with Jaune moving his hands and placing them behind his back.

The smile Glynda wore was downright predatory as her hips pulled back and let Jaune suck in some greedy breaths of air. Once the subtle nod was given, Glynda placed her other hand on the man's cheek. Glynda moved the hand to his hair and slowly pushed the toy forward till Jaune gagged. The older blonde stopped and pulled back a bit. A flash of defiant blue eyes lit a fire in her stomach sending the message loud and clear.

The same smile that struck fear into the hearts of children across beacon sent shivers of pleasure up Jaune's spine. He opened his mouth as wide as he could as the grip on his hair grew tighter. He had read books and seen vids, he had an idea of what was going to happen. Nothing could have prepared him for a sex-deprived stressed beyond belief huntress that could move objects with her mind.

Jaune got in one last breath of air before his windpipe was filled with plastic cock. It felt like a solid minute before it was violently yanked out of his throat and put itself back just as quickly. The process was quickly repeated for several minutes, with Jaune's throat being stretched around the toy. His saliva kept it sufficiently lubed while the grip on his hair was growing tighter with each thrust. The vibrations she felt told her he was humming.

Suddenly the tip of the plastic cock found the back of his throat and stayed there. Darkness ate away at his vision rapidly as the toy jerked a few times before pulling out. Panting could be heard as Jaune's vision quickly cleared. His eyes trailed up from her pale thighs to the lust-filled orbs staring back at him. Glynda's hair was an absolute mess considering she had probably been bucking her hips hard and fast. Her hands were still in his hair, though not exerting as much control. His throat protested the rigorous abuse it had just undergone by taking away his ability to speak without some pain. His libido, however, was on fire and begged for more!

Jaune found himself being pushed back, with her hands still firmly gripping his hair, as she leaned down and pecked his lips for the briefest of moments. Her lips left a trail of kisses down his wanting body. She finally stopped before his twitching cock and she smiled. Such pleasurable times she had thanks to it and the man attached to it. Her tongue stuck out and her mouth opened wide to engulf the head. At the last second, she stopped and looked at her lover. His eyes were pleading, his hands gripped the sheets instead of her hair, she knew exactly what he needed at this moment and pulled away before standing up at the edge of the bed.

"Get on all fours for me and back your cute ass up Jaune," she commanded with half-lidded eyes, slowly bouncing the strap-on up and down as she spoke. A grin split the headmaster's face as he turned over hurriedly and back crawled to where his knees were on the very edge. The blonde witch took a step forward and rubbed his puckered hole with the lubed cock. Leaning over next to his ear she whispered to him, her hot breath washing over his skin.

"Have you been bad Jaune? Do I need to punish you?" The almost inaudible whimper was the only response that Glynda got. One blonde leaned up while the other brought a pillow toward them as the cock pressed against the ring of muscle. Feminine hands found Jaune's hips and pulled him back as her hips pushed forward. Every movement against Jaune's ass meant the double-ended strap-on hit the most sensitive spots in Glynda, causing her to moan. After one short thrust, both blondes were moaning as Jaune was finally penetrated.

Glynda panted for a moment gathering herself. She didn't expect this would work as well as it had but she was glad that she decided on this particular toy. Being left unsatisfied just wouldn't be fair. Looking down she saw only about an inch made its way in and that was just a shame.

"Only nine more to go Jaune. I believe in you." Her words soothed him even though the single inch was enough to have him on edge. He nodded his head once and felt the grip on his hips tighten. The lubed plastic softly scraped and slid against the soft muscles as it made its way in. Jaune felt nothing but the rush of endorphins and a light-headedness that came from having a dream fulfilled.

The resistance caused the dildo to move inside Glynda making her moan as it hit sensitive spot after sensitive spot. Finally, all ten inches were buried in Jaune's tight ass. She looked down to see the normally strong and powerful frame of Jaune Arc now a whimpering mess that begged for more. His head was face down on a pillow, one hand disappeared below him while the other grabbed the sheets. Repositioning her hands to his ass she slowly pulled out and a fresh chorus of moans escaped the man.

Not able to control herself for any longer, she pulled back as fast as she could then slammed forward. The cry that echoed around the room was pure music to her ears, so she repeated it again and again and again. Every time she thrust forward the cries became moans, and the moans turned into begging. A pace that was comfortable for her was finally found, where the dildo could only be seen for a quick second before vanishing back into his tight hole.

If the moans were anything to go by, Jaune loved it. He loved getting fucked by her as much as she did by him.

As time went on, Glynda's will diminish and she couldn't hold out. She finally came as she pushed her hips forward and held them there. As she was riding out her orgasm she felt the toy move in her, causing her to gasp. She was still hypersensitive so any slight movement drew forth another reaction. Looking down at Jaune, she noticed him biting the pillow as his hips jerked as a white liquid shot out of his cock. It appeared that she wasn't the only one to be pushed over the edge.

His nerves were calming down with every ragged breath. Jaune's hands gripped the sheets tightly as his mind focused again and the grip around his insanely hard dick was loosened. Two soft pillows pressed against his sweaty back as hot breath washed over his ear causing him to shudder. Some blonde hair tickled his cheek as he saw her flushed face beside his.

"That was amazing." The words came between the soft panting of them both. He turned his head to the side in time to capture her lips. They parted after a few minutes, panting hard for breath. "Do you have anything planned tomorrow?" Glynda smirked at his words.

"It'll be hilarious to see you walking around to all your meetings." Jaune's face grew pale and his eyes went wide as she flipped him over. Somehow the plastic cock hadn't moved in or out but the turning caused a fresh moan to escape his mouth. Slim fingers wrapped around his twitching cock, making his head jump up as blue eyes lock onto emerald ones. The promise of an all-night fuck session from the horny witch had him excited beyond belief.

They wouldn't last all night, but they would go on for a very, very long time. Throughout the night, one of six people would venture near the room and immediately leave once they heard the noises, congratulating the boy's fortune while not knowing the true nature of the bedroom's events… well, one of them did.

Jaune woke with a start to a cold bed and a gentle breeze blowing in. After rubbing his eyes into working order he noticed several things. Glynda was no longer in bed, his ass was sore, and Neo was sitting on the foot of his bed smiling. Several things should have had him worried, the first thing was Neo, but he couldn't bring himself to care that much. Suddenly Neo was on top of Jaune smiling down at him as she licked her lips.

"N-neo?! Good morning!" The mute pointed over to his bed stand where a note lay. He reached over and grabbed it.

I hope we do this again, and not in another year xoxo
-Glynda

Jaune smiled. That wasn't a bad idea. Maybe they'd do it again in a week… maybe a few days… tonight even?

He was brought out of his thoughts by very familiar noises. He turned to see Neo watching a video on her scroll. Jaune leaned over to see what it was and… he was more surprised at his lack of surprise that Neo secretly recorded their night. The mute looked at him with a smirk and wiggled her eyebrows.

Jaune just sighed. He was not in the mood to argue with her. "Look, just don't show that to anyone, ok?" Neo nodded and pulled her pointer finger and thumb across her closed lips before giving him a thumbs up. Well, at least he didn't have to worry about that. Now, he just had to worry about if he had a limp or not.

Thanks for reading, have a great day :)