Who Chaperones the Chaperones? (Patreon)

So this idea actually came second in the poll but since the winner is getting released on Halloween day I thought it might be a good idea to write this one, keeping it short and sweet, and released it between now and then so you guys have something to enjoy before the last day of the month. 

It was the last Friday before Halloween and the Blue Valley Junior High dance was in full swing. Since most of the upper classmen went went off campus for their festivities the school board stopped hosting a dance for high school several years prior. There was still more than enough of a turnout to make middle school dances viable though and that was how Mrs. Hollis found herself as one of four chaperones for evening. She certainly didn't mind doing it, even if her motivations weren't exactly altruistic. Those reasons were why, although she'd never admit it, she'd picked her costume for the evening. For the occasion she'd gone with some simple but flattering, while keeping completely appropriate of course. A form fitting, long sleeved black gown that stopped an inch or two past her ankles. Despite the collar reaching nearly up to her chin and the entire ensemble leaving nothing but her dusky face and hands exposed she still managed to look quite alluring. Perhaps it was the wide brimmed witch's hat tilted at a jaunty angle atop her wavy auburn hair to partially hide her hazel eyes while fully revealing her full, red lips and slightly upturned nose. Or more likely it was her wide, buxom hips and long legs paired with an ample bosom and an thick ass that simply refused to quit. Her strong blend of German and Italian features suited her choice of costume remarkably well, even though she'd forgotten trademark black rimmed glasses. Thankfully Mrs. Hollis always had a spare pair of contacts in her desk, otherwise she wouldn't be able to cast frequent, smoldering looks across the gym at her former student.

Danny Mueller was more than happy to return her meaningful stares whenever he could. After all she was the sole reason for him being at the dance and nowhere was that more apparent than in his costume. Grabbing the first thing he could off the shelf at the grocery story he was dressed as a rather threadbare version of the Grim Reaper in an outfit a few sizes too small. Both the sleeves of his jacket and the legs of his jeans were visible beneath the cloak and the hood meant to shroud his face barely reached the top of his head. It made for a rather comical sight even if his naturally charming smile and periwinkle blue eyes offset the look quite a lot. And the fact that he was more than twice as tall as many of the kids he was watching over meant he could have dressed however he liked while still being quite intimidating. To the students at least, for Mrs. Hollis and the other teachers present he was just eye candy. Although none of her coworkers knew about the little tryst they'd had a few months prior and they certainly didn't know about the three other liaisons that'd taken place since then. Had they been paying attention they probably could have guessed from the nakedly lustful stares each was giving the other or the way they seemed to constantly drift closer to each other as the night wore on. But, as luck would have it, the other two teachers were just a bit too preoccupied with keeping the students in line to notice the lack of subtlety between Mrs. Hollis and Danny. Even when they both moved to the punch bowl for a moment of hushed conversation. 

“Are you enjoying yourself?” She asked in a neutral tone.

“Oh yeah it's all kind of fun.” He replied, “Almost makes up for all the ones I missed when I was age appropriate.”

“As I recall you always had 'better things to do'.”

“Those video games weren't going play themselves.”

“Of course not. Still, it's a shame you missed out on the full experience.”

Taking a sip of punch and immediately setting his cup down Danny looked around the gym for a moment, “I think I've got the gist of it.”

“Is that so? I guess you would know.” She remarked, turning away from him with an over the top smile.

“What are you—”

“I need to use the restroom, can you cover for me?”: Mrs. Hollis asked of her coworker in a slightly louder tone then necessary.

“Sure thing dear. We'll be fine.”

“Thanks. I won't be gone long.” She stated, glancing coquettishly back at Danny as she spoke.

His eyes widened and he watched her saunter out of the gym with wide eyes and a slightly opened mouth. She couldn't possibly mean what he thought she meant. That wasn't like her at all. Of all the many things he enjoyed about her Mrs. Hollis was a very responsible person. Abandoning a school function to have sex just wasn't like her. Then again he was still learning new things about her every time they saw one another. Who's to say she wasn't exactly that kind of woman? Wracked by indecision Danny stood by the punch bowl for several minutes before making a similar excuse and leaving the gym after her. He made it halfway to the nearest bathroom before he was ambushed by Mrs. Hollis darting out of a classroom and yanking him inside.

“God what took you so long?!” She gasped, swooping in for a passionate kiss.

“I wasn't sure you were serious!” Danny replied between frantic kisses.

“Maybe we should come up with a code word!”

“Or you could just tell me what you want!”

“Where's the fun in that?”

“You're right. This is a lot better.”

“I know—oh!”

Katrina gasped as she was lifted off her feet and hurriedly carried into the small supply closet near the teacher's desk. Danny kicked the door shut behind them and kissed her in earnest. His hands roamed her body while her slid down to his tight butt and held on for dear life. She wrapped one of her legs around his and gently grinded against his unmistakable bulge. Soon their lips were parting and their tongues danced in one another's mouths. Neither paid any heed to the sounds they were making, all thoughts of the dance or being discovered completely gone from their minds. Passionate gasps and the constant sound of connecting lips and ruffling clothes filled the room. At some point her hat was knocked off her head and she weakly attempted to catch it. Her flailing hand was intercepted by one of Danny's and their fingers quickly interlocked. They finally broke apart to smile at one another, Katrina's body pressed up against a tower of boxes and his keeping her firmly pinned there. A quiet moment passed between them as both took the chance to silently stare into each other's eyes. Once it was over the lust immediately took over and he made his move.

Sinking to one knee almost like he was proposing Danny pushed up her dress, slid his hands beneath the skin tight cloth, and pulled her panties down past her knees. While she was still panting from the whirlwind start of their rendezvous his head disappeared beneath the remainder of her gown. She felt his breath against her bare pussy and goosebumps spread across her body. A split second later she felt a lot more than that as his tongue slid inside her sex and his lips pressed against her puffy outer folds. A powerful, full body shiver danced up her spine and it was all she could do to not collapse as soon as he started. With shaking hands she lifted her dress up until she could see Danny's face and her garment was little more than a shirt. Gripping the bunched up hem with one hand she grabbed the top of his head with the other and let her head fall back against the wall. He was well beyond the point of needing any sort of guidance of coaxing. His tongue was already swirling around within her pussy in a way that just never failed to make her quiver. Like it was nothing he hit every single spot that'd ever caused her to gasp, moan, or whimper. And both of them knew it was only his opening maneuver. 

While Katrina's juices gushed into his mouth and he dutifully drank every last drop Danny slowly started to pull away. His retreat was both gradual and calculated as his tongue never stopped moving around her slit for a single second. Even after it'd completely withdrawn from her pussy it still glided along her silky folds to collect the dew gathered there. It darted across every centimeter of her folds in a seemingly erratic pattern than always left her mind playing catch up to the pleasure exploding through her body. With his strong hands keeping her thighs spread open so he had complete access at all times she almost felt like his plaything despite what was actually transpiring. About all she could possibly do was spread her fingers through his tousled hair and let him know how much she enjoyed his efforts. As loudly and enthusiastically as possible. Her voice only grew louder when Danny furtively slid the middle finger of his right hand into her pussy while at the same time wrapping his lips around her clit. Crying out with enough force to make her throat hurt Katrina had to cover her mouth with one hand to keep from giving their position away. Although her trembling fingers barely affected the sounds spilling out of her mouth. Nothing short of the ball gag she'd been wanting to try out could really stop her by that point. She'd always fantasized about someone going down on her while she was at her desk or doing something equally mundane and this was about the closest thing to that she could experience. Without risking the loss of her job or jail time. And once that realization took toor inside her mind there was nothing else she could focus on.

Perhaps with the possible exception of his strong finger curling inside her slit and his equally talented tongue flicking her tender bud. Those were excellent distractions from the overactive fantasies bouncing around in her head. She was helpfully given another distraction, along with a burst of added pleasure, when Danny pushed his ring finger into her slit as well. All of a sudden he was able to massage and tease her g-spot with almost unbearable efficiency. Within seconds her legs were trembling and her voice was starting to fail her. She pushed herself as hard as she dared against his mouth while his fingers continued to probe and rub her inner walls. Yet every time she attempted to grind against him a powerful surge of ecstasy would rock her body and she would reflexively pull away. The first few times he simply allowed her to retreat and continued fingering her with practiced ease. But eventually he started matching her movements, leaning in when she moved back and pulling away when she shifted forward. Like a dance they shifted in tune with the ebb and flow of her pleasure again and again as she grew more flustered and overwhelmed by the second. Her toes curled inside her shoes and she constantly muttered half formed words and syllables while he continued reading her like a book. There was no telling how long they'd been going at it in that darkened supply closet, the only measurement of time she had was the rhythmic shifting of his tongue and fingers against and within her pussy. And even that was unreliable as her enjoyment continued to rise. Before long all she could really be certain of was just how close she was getting to a nice, shuddering climax. Along with how badly she wanted it and how much she adored him for bringing her to that point.

“Yes, yes, yes, yes, yes, YES, YES, YES!” Katrina moaned, slamming one fist against the wall and tearing a few hairs from Danny's head as her whole body shook, “OH GOD YES!”

Pleasure washed over her like a cresting wave. Every muscle in her body tightened for a moment, then they all started to spasm uncontrollably. Her legs attempted to close around Danny's head while her hips grinded against his mouth. The walls of her pussy clamped down around his fingers and coaxed them deeper than ever into her slit. At least until her wild, unpredictable contractions attempted to push them right back out again. But her man was no stranger to how her body reacted and he managed to counter or overcome everything she did to keep his tongue on her clit and his digits pressed against her g-spot. For his dedication he was rewarded with the most adorably genuine whimpers and moans Katrina could make. Sounding completely unlike the strong, even demanding, woman she was the sounds coming from her mouth would've been more fitting for a woman half her size. And the way she stared uncomprehendingly down at him, her eyes glazed over and her mouth hanging open was simply delightful. It took all of his willpower to remain between her sweat soaked thighs instead of standing up to kiss her as he so often did. Even if she hated the taste of her own pussy that burst of passion hitting her like a bucket of cold water would have been worth it. His indecision made the choice for him and he pulled away as Katrina slumped against the boxes and a trembling heap. The aftershocks of her orgasm continued to ripple through her while he lifted up his costume and freed his painfully erect member. She stared listlessly down at his prick, part of her very much wanting to tell him to slam it inside and go wild. Unfortunately she was having trouble find her voice and he decided to err on the side of caution. Stepping forward and slowly entering her quivering slit Danny thrusted as slow as possible, fully aware of how sensitive she was post climax.

“We don't have much time.” She panted as his cock was buried inside her pussy.

“Do you want me to stop?” He asked as he slowly thrusted in and out.

“No of course not! I want you to go faster!” She purred.

Her hands cupped his face and she smiled at him with that lusty grin that never failed to drive him crazy. He nodded and pulled her into a slightly more convenient position, his hands gripping her waist tight. She felt him shift as his stance widened and he readied himself with a cute little squaring of his shoulders. In the blink of an eye her amusement melted into an open mouth, pleasure wracked stare as he started pounding her tight little slit. Starting at a speed it usually took him quite a while to work up to he moved his hips like a jackhammer as he bared his teeth and groaned like a wild animal. The speed and ferocity of his movements only continued to grow as he truly let loose. Their little closet was absolutely filed with the sounds of flesh colliding against flesh, the wet slaps of their bodies spilling out into the classroom beyond at a such a volume they might as well have been fucking in the center of the room. Katrina's almost timid moans were completely drowned out by the sound of his cock furiously slamming into her like a piston but Danny was more than aware of how much she was enjoying it regardless. Even if he couldn't feel the wild twitching of her pussy his eyes were glued to her face as she stared at him. They momentarily darted down to her hands as she grabbed his forearms and held him tight. In the trip back up to her face he noticed her breasts bouncing and jiggling beneath her dress, the tightness of the fabric making them seem even larger then they already were. Suddenly his eyes could find nothing else to look at and his hips unwittingly moved a little bit faster. Smiling at his obvious and continued fascination with her breasts Katrina subtly squeezed them together between her biceps. Rather instantly she felt his dick throb at the added visual stimulation. When it continued to throb harder and harder she knew it was only a matter of time before his big finish.

“Are you close?” She asked despite knowing the answer.

“Yeah!” He groaned.

“Pull out!”

“What?”

“Pull out!”

Doing as he was told Danny's cock emerged from her pussy in a shower of fluids. Katrina sank to floor and wrapped her lips around his shaft, momentarily grimacing at the taste of herself. Since there was no way he could finish inside her without ruining her panties and dress she only had one choice. It was a fairly easy one all things considered and once she'd gotten past the initial unpleasantness her head was bobbing back and forth along his shaft at the same speed he'd been fucking her just moments ago. After a few seconds Danny was grabbing her head and pulling her down to the base of his prick. She smiled around his shaft and closed her eyes while his cum erupted into the back of her throat. She swallowed what little didn't gush directly into her belly. Her soft moans and slurps were barely audible over her partner's labored breathing but they still managed to make his dick throb and his crimson face grin. He pumped a considerably amount of spunk into her belly, more than he had in quite some time, before it was over. Towards the end Katrina was actually lamenting the circumstances of their tryst. Such a healthy amount of semen deserved a lot more than simply being swallowed up. But the overall thrill of sleeping with a former student yet again while blowing off her duties as a teacher managed to overshadow that minor issue. This time at least. He'd have to give her a nice, messy facial the next time they were together just to keep things balanced. She slowly pulled back from his softening prick, her eyes locked with his as his member slipped from her mouth and twitched in the open air. She gave the thickest part of it a little kiss and laughed at the look on his face. It was a cute mix of amazement and adoration that never failed to make her feel both slutty and cared for.

“We should go back to the dance now.”

“Yeah . . . do you think they noticed we were gone?”

“I'm sure they did.” She replied, taking the hand he offered her and rising to her feet.

“Right. Do you think they know what we were doing?” He wondered as he tucked his cock back into his pants.

“I have no idea.”

They took a minute to get themselves as presentable as possible before stepping out of the supply closet and into the classroom. After pausing to share a quick kiss Mrs. Hollis turned towards the door to leave first, only to stop dead in her tracks. Standing outside peering in through the window was the two other teachers she'd left chaperoning the dance. Both were wearing ear to ear grins and looking so smug they could have won awards for it. Looking utterly mortified Mrs. Hollis slowly turned her head to stare at Danny, her eyes as wide as his and her face even more pale. Neither knew what to say or even what to do as they stood there frozen in time until he finally spoke.

“I think they know . . .”