Chaperone
Patreon story for Ruffe
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Jonathan checked his reflection in the glass of one of the school's trophy cases, adjusting his bow tie before walking into the auditorium. Music, if it could be called that, was blasting from the speakers in time with dance lights. Teenagers were standing around talking, dancing, and recording video on their phones of one of the biggest nights of school; Prom.
The young men were dressed in fashionable tuxedos, though none were tailored to fit quite as nicely as Jonathan's. He chuckled to himself and walked onto the floor, looking around until he spotted a shorter, male husky in a black tux. Jonathan put a paw on the student and smiled. "Ah, see? You look great," he said.
Robbie, looked up and then smiled sheepishly. "Thanks, dad. I'm glad you came. You look good, too," he said.
The older husky straightened up and puffed out his chest proudly. He looked much like his son; typical husky colorings, but with more muscle, and a bit of greying fur around his muzzle. "I certainly try."
Robbie chuckled and nudged his dad with a shoulder, cheeks red. "Just don't embarrass me, okay?" he said, though he was smiling.
"Now now, I'm just here to keep an eye on things and take lots and lots of pictures. Lots. Just gotta go get my fanny pack real quick so I have a place to carry the camera," he said, feeling around his waist as if looking for the pack.
"Daaaad!" Robbie pleaded, pushing on his dad's arm and laughing. "Just don't make it too obvious, please? And no flash."
"No flashing. Got it. I promise I won't flash your friends," he teased, drawing another complaint from the teenaged husky.
"What's this about flashing?" a feminine voice came, drawing both their attentions.
Jonathan whipped his head around, and found himself standing in front of a rather stunning, young fox. Her black hair was in loose curls that fell past her shoulders and a simple pearl necklace was close to her neck. Sparkling blue eyes shone in the dance lights as they pulsed with the music, and her lips looked delicate and inviting with the fiery lipstick. She was wearing a floor-length gown of blood-red with matching gloves that rose to her elbows. The dress had a slit up one side that showed her bare leg beneath and her crimson heels.
The older husky stared blankly for a few seconds and he felt his cheeks heat up as he tried to remember what he'd just said. "I... I'm sorry, what did you say?"
Robbie rolled his eyes and nudged his dad in the side, ears flicking back. "Hey Jessie," he said.
Jessie laughed and brushed her luxurious hair back over a shoulder and smiled brightly at the young canine. "Hey Robbie. You two were saying something about flashing?" she repeated, lips pursed together in a controlled smile.
Jonathan's mind didn't want to work. An almost feral part of his mind wanted to lean in and bite those ruby lips just to get a taste of her. He blinked at her a few times and then laughed. "Flashing. Camera flashing. Flash. No camera flash," he said, rubbing the back of his head and looking to his son and then back to the vixen.
Robbie looked disgusted and embarrassed, but Jessie just brought a gloved paw up to her mouth to cover her laugh. "Oh, I see. Robbie, I'm guessing this is your father?"
The young husky sighed and nodded, looking between them. "Dad, this is Jessie, Jessie this is my dad," he said, discreetly nudging his dad in the side.
Jonathan grit his teeth at the jab and smiled wide. "Ah, Jessie. I've heard your name a few times, though I don't believe we've met."
She shook her head, curls falling back around her face again. "No, we haven't. But it's a pleasure to meet you, mister Callaghan," she said, bowing her head gracefully.
By now, the older husky had regained much of his composure and bowed his own head. "You as well. You look lovely this evening," he said, glancing over her and chiding himself for some of the thoughts he had. She wasn't an endowed woman at all, but her figure was slim, and her mannerisms graceful.
"Thank you so much, sir," she said, putting a little more emphasis on the last word that briefly caught the man off guard. "Both of you look exquisite tonight, too. I can see where Robbie gets his good looks from," she said, looking from the younger to the older.
Robbie rolled his eyes again and grabbed the girl by an elbow, starting towards the dance floor. "Okay dad, we're going to go dance. Talk later," he said, not looking back.
Jessie giggled and hurried along after the young canine, glancing back at Jonathan and smiling apologetically. He could only watch her walk away, eyes shamefully roaming down along that waving tail and supple rear.
It took him a few moments to fully recover after his son and his friend left, and he then felt the wave of guilt and perversion wash over him. He mentally chided himself for getting so worked up over the young girl. "You pig," he grumbled, shaking his head. "It's only cause Julie looked that good at our prom," he said, thinking of his wife, silently glad she was too sick to chaperone tonight as well.
The older husky sighed and fished his camera out of his pocket and began to take plenty of discreet, flashless pictures of the dance floor, decorations, and students dancing.
As the night continued, he caught glimpses of the beautiful fox girl on the dance floor. There were plenty of other girls out there, dancing provocatively and shaking their butt at some of the boys, or thrusting out their chest, but Jessie was something else.
The way she moved was far more graceful and poised like a real woman's should be. She didn't falter once on those high heels and her dress never tripped her up or made her stumble. Those sapphire eyes found his a few times and she'd flash him a gorgeous smile that tightened his chest, and pants. He couldn't help but entertain himself with more racy thoughts, and wondered what she would think if she knew.
He had to remind himself just which kid he was here to take pictures of.
She danced with a few of the guys, of which Jonathan recognized a few of his son's friends that visited the house, and he felt a pang of jealousy that he couldn't join in. His wife was going to get a lot of attention tonight, head-cold be damned.
It was getting too much for him to bear and he looked around at the other parents and faculty members before ducking out of one of the side doors to excuse himself to one of the bathrooms. He knew where the main ones were, but with so many students going in and out, he knew there'd be no privacy.
A minute later and he was splashing cold water on his face in an empty men's room. "Damn," he said quietly, staring at his reflection in the mirror. He was breathing hard, for Pete's sake! He wasn't even one of the ones dancing! That girl had gotten him far too worked up, and he would have to get home to find an acceptable distraction from these thoughts.
His last chance to have a socially acceptable night ended when the door behind him opened and the vixen stepped through into the restroom. Jonathan saw her in the mirror and spun around, paws behind him, gripping the porcelain sink. "Jessie! What are you doing in here?"
She giggled softly and took a few steps forward, her heels clicking on the tilted floor. "Sorry, sir, I thought you'd wanted me to follow you," she said sweetly, gloved paws holding each other in front of her.
Jonathan tilted his head to one side, perplexed. "Wh-what? Why would I want you to follow me?" he asked, standing up straighter and pressing back against the sink.
Jessie frowned and took another step forward, pursing her lips and letting her paws fall to her sides. "Oh, well, you'd said how lovely I was in my gown, and... I couldn't help notice your noticing," she said, looking up at her with a gentle pout.
The husky's throat went dry and he gazed back at her, his heart pounding against his chest. "I-I think you've got me mistaken, I-"
"You don't find me lovely?" she asked, looking crestfallen. Long eyelashes batted at him sadly and she took another step forward so their chests were almost touching.
"I," the husky started to say, eyes flicking across her lithe body. "No, I do, I really really do, but-"
She silenced him once more by standing on her tip toes and pressing her luscious lips to his own, tongue darting out to tease him. At the same time those gloved paws slipped around his waist and hugged him close.
Jonathan felt himself tip past the breaking point as her muzzle meshed with his own. There would be no way he could walk away and ever forgive himself at this point. A soft whimper escaped into her muzzle and his strong paws pulled her tight against his chest.
The kiss seemed to go on for an eternity. The music from the auditorium could faintly be heard from this distance, but Jonathan was certain that the sound of his beating heart would drown it out. Her perfume was so subtle that her natural scent was easy to pick up, and it made the husky's nostrils flare with arousal. She had a very unique aroma to her that he couldn't quite place.
Her dress was backless and his paws ran down her bare fur, finding her slender frame to be layered in a subtle layer of muscle that most girls didn't have. "She's probably an athlete," he thought as the kiss continued, tongues coiling around each others.
It wasn't until her hips rolled forward against his that his eyes went wide as everything clicked. There was a firm protrusion behind that red silk that ground against his own and he realized that wonderful, heady scent he'd been taking in was her musk. His musk.
He broke the kiss with a confused, inhaling sound and looked down at her. Jessie laughed and reached one of those gloved paws back up to his face, cupping his cheek. "Oh, I thought you knew, since you said Robbie had mentioned me a few times," he said, batting his eyelashes at the bewildered husky.
Jonathan didn't know how to react to this situation at all, though his body didn't seem to put up much of a fight as those hips rolled against his again, grinding their trapped cocks together. "You. You're a guy," he stammered dumbly.
Jessie laughed and slipped both paws between them, squeezing the husky's thick shaft through his slacks. "Yes, and you are obviously one, too," he cooed, rubbing up and down that bulge.
The husky's cock throbbed in her paw and he grunted, hunching towards her. "I'm not that kind of guy," he whispered, though at this point he wasn't entirely certain he could make it out of there.
"What kind?" he asked, fingers popping open the button on his slacks while sliding the zipper down. "The kind of guy who leaves a poor, needy girl alone in the bathroom?" he whispered.
Jonathan's body shuddered as a slim paw pulled his boxers and slacks down around his thighs. Pre spurt out against his gloved paw and he rubbed the silk cloth against his dripping tip while the other cradled his length. "J-Jessie, you're... you're not..."
"I'm not going to leave you all pent up and uncomfortable," he said reassuringly, kissing Jonathan's cheek and slipping down to his knees before the man could argue further.
The husky gasped as he saw the boy sink to the floor in his evening gown. Jonathan's angry, pulsing shaft sprayed a line of pre against the top of Jessie's muzzle and then the teenage boy parted his painted lips to take that thick shaft halfway down with a greedy moan. A silk paw cupped his hanging balls and gave a firm squeeze while those lush lips slid down over his flesh, tongue teasing over the veined surface.
Jonathan had to reach back and grip the basin again as the crossdressing student bobbed back and forth along his cock, teasing more and more pre from his twitching shaft. Their eyes made contact as Jessie gazed upwards and the husky's face heated up in a way he hadn't been accustomed to since his first time with a woman.
All too soon that beautiful muzzle pulled off his length and the fox stood back up. "Please, sir? Indulge a willing, young vixen?" Jessie asked, turning around and hiking his dress to the side by the slit up one leg.
Jonathan's eyes traveled down to the black, lace panties beneath the red dress and his cock drooled out on the tiled floor. He knew he wasn't going to forgive himself if he'd left earlier, but now he wasn't entirely certain if he stayed. Another heartbeat later, followed by the sound of something wet hitting linoleum, and he'd made his mind.
He gripped "her" hips and pulled her back around so she was braced against the sink, and she gasped out in surprise, giggling after. "Ooh, sir..." she whispered, carefully reaching back to tug her panties down to allow him access.
Jonathan held her dress to the side with one paw while his other guided his tapered cock to her entrance. His wife had let him do this on a few occasions, and he briefly wished he'd had more lube for the occasion, but was pleasantly surprised when the first thrust forward sunk his cock in to the growing knot with little effort.
She was hot and tight, and Jonathan was surprised he didn't blow right there. Jessie made a soft mewling noise and pushed back against the older male, shuddering from the sudden intrusion. "Ooh, sir, you're so thick," she whispered.
The husky felt his blood boiling as she spoke and he let out a guttural growl as he tugged back and humped forward again. A moan echoed off the walls from both their mouths. Soon enough the gentle slapping sound of the husky's heavy balls smacking the pert, fox rear filled the restroom.
Jessie was gripping the edges of the sink with both gloved paws, humping back against the older husky's thrusts and he badly wanted to ask the man to help stroke him off while they mated, but didn't want to break the man's fantasy. His eyes watered as he focused on that thick cock pistoning through his entrance and he felt his knot growing inside his taut sheath, too big to be freed from the holder at this point.
Jonathan couldn't take his eyes off the "vixen" in front of him. He could see her expression in the mirror, the pure ecstasy as each thrust forward made her gasp and whine. His own knot had swollen to the size of a baseball and it pounded against the teen's hole, trying to gain entrance. His wife hadn't ever let him tie with her when doing anal, and he wasn't entirely certain that Jessie would let him either.
The fox's face was a mask of pleasure and he his fur was on end as the older male took him. "Please... please tie me. Oh god, I need it," he whispered, looking up at the man through their reflection.
Those sapphire eyes locked on his own, Jonathan felt his heart skip a beat and his thrusts faltered briefly. She wanted him. She wanted all of him. He gripped the base of her tail in one paw, hip in the other, and tugged back hard. An audible pop forced his engorged knot into her and both saw the look of bliss on each other's face as they came together.
Jessie had the foresight to hike his dress up in the front before the fun started, and thick ropes of pearly cum splattered noisily against the bathroom floor, coating the wall and the underside of the sink. Jonathan's load pumped deep into the fox's passage and he hugged her up against his chest as he came, their chests heaving with exertion. Cum dripped from around his knot in thick strands, leaving a warm puddle between Jessie's red pumps.
Jonathan looked away before Jessie did and he felt a wash of emotions pass over him. He'd just had sex with his son's friend. His male friend. At the school Prom. He'd get in trouble with every last person if anyone ever found out and he knew he should be disgusted with himself, but he could only feel a deep satisfaction in the pit of his stomach.
Jessie groaned happily and closed his eyes, reaching back with a slightly damp paw to pat the husky's cheek. "Ooh, sir... that was amazing. Robbie asked if I wanted to spend the night tonight, do you... think that'd be okay?" he asked, squeezing his muscles down on the husky's knot.
Jonathan grunted and his hips lurched forward into her, more cum dripping out onto the floor beneath them. "That... that sounds lovely," he said, kissing the back of her neck as the cheeks and the inside of his ears turned pink. "Boy or girl," he thought, "he really kills that dress..."