Late Night Encounter

Story by ShadowLightning on SoFurry

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#2 of Tutoring Sessions

Well, here it is! The exciting sequel to the previous story. I started working on this almost as soon as I finished the first, but due to lack of motivation (quarantine didn't help with it at all), I kept pushing it back further and further. Funny how I regained that motivation once I uploaded the first part on here.

Anyways, comments and constructive criticisms are always appreciated. Hope you enjoy~


It was 9pm, late into the night. A good number of people were still awake in the dormitory. Some were playing video games while others hung out with their friends. It was the weekend, after all, and they all felt they deserved to have a nice break. Kyle however stayed cooped up in his room as usual, studying the night away. It was lonely at times but it was how he managed to keep his grades up. Still, he sometimes wished he had friends to spend time with. He let out a sigh at the thought before turning his attention back to his books.

The room was quiet, with only the soft music coming from his phone breaking the silence. The light from his lamp kept his desk fairly lit, shining over his books and papers. While he kept his room as clean as he could, he had trouble organizing his school things. They piled up around his desk and bits of were strewn on the floor. His bed was on the opposite end of the room next to his bathroom door.

The fox hummed quietly along with the music as he read through his notes. His concentration was broken however as the song stopped abruptly. His phone vibrated and let out a notification sound. He tilted his head curiously as he reached over to check what it was.

Who could be messaging him at this time of the night, he wondered.

It was a message from a certain boar down the hall.

"heeeey, doing anything?"

He rolled his eyes and ignored the message, turning his phone back down as he went back to studying. After a few moments however, it vibrated again. He let out an annoyed groan and checked to see another message.

"i know you're awake ;3"

His eyes grew wide and quickly looked around the room, replying back. "HOW DID YOU KNOW?"

"I didn't. Was just bluffing XD"

Kyle blinked at his phone and sighed.

"can you come over? :3"

He huffed out and messaged back.

"Sorry, I can't. I'm studying."

"Aww boo. On a Friday night? xd"

"It's how I pass my classes. Unlike a certain someone."

"Maybe i just need more tutoring sessions with you :3"

His cheeks blushed slightly.

"Don't you have other friends to hang out with?"

"They're all out drinking. Also kinda saving money sooo xp"

He rolled his eyes.

"Come on, pleeeease? I'll be less rough on you if you want ;3"

He blushed even more as he considered his offer. He was just thinking how lonely he was earlier, and he felt he had already done enough studying for the night. He hesitated at first before eventually replying back.

"Alright, fine. But you come over here instead."

"Yaaaas! I'll be right over ;p"

It didn't take long for Randy to head down the hall and knock on Kyle's door. The fox gulped and took a deep breath, opening the door and was greeted by the boar looking down at him with a wide grin on his face.

"Hey there."

"H-Hey." He stepped aside and let him come in, closing the door behind him while he scratched the back of his head. "So, uh, w-what do you wanna-"

Before he could even finish, Randy quickly picked him up and carried him over to his bed, letting out a yelp as he was set down on his lap.

"W-Was that really necessary?!"

"Just to see your reaction? Definitely." The boar teased, softly kissing the fox on the nose.

Kyle's cheeks blushed brighter, wrapping his arms around the boar and nuzzling him softly. His face showed a clear expression of annoyance, though his body however was showing otherwise.

Randy chuckled at the look on his face, holding the fox close as his hands gently rubbed his back, nuzzling his face in return.

They sat like that for a while, hugging each other close. The fox murred softly, enjoying the gentle nuzzles from the boar, to which he responded with a low grumble of approval. His large hands then moved lower down his back, reaching for his plump rear and groping them, groaning at how they filled his hands.

"Mmmmm..."

The fox yelped at his touch, nuzzling against his head as his paws clung to the boar.

"Like that...?" The boar teased.

He nodded.

"Good." Randy nuzzled against Kyle's head more, getting him to tilt it slightly before leaning close to kiss him on the lips, making the canine whimper and yelp in his maw. The boar couldn't help chuckling more from his reactions, keeping the gentle kiss going for a while before slipping his long thick tongue into his muzzle. His hands fondling his fat ass more roughly, snaking its way into the fox's shorts to grope him more.

Kyle shivered against his touch, his arms still wrapped around the boar as they made out, his tongue reluctantly sliding around his invading organ, drawing a delighted growl from Randy. His paws gently rubbed his back while the other held onto his head.

The boar squeezed his chubby cheeks hard as he kissed him deeply. His one hand then slipping out to grip the back of his shirt, slowly pulling it off the fox, never once stopping his deep kisses. The canine in return did the same, helping Randy in peeling his clothes off of him. They undressed each other while keeping their bodies close, grinding their soft bellies and chests together while their lips and tongues stayed interlocked. It didn't take long for both of them to be completely naked, the boar's eleven inch member throbbing hard as it pressed against the fox's smaller five inch cock..

"So..." Randy reached down and gently stroked both of their members together, making Kyle moan out. "What'd ya wanna do?"

"H-Huh...?"

"I dunno, just thought maybe you'd wanna decide this time." He licked his cheeks and grinned playfully. "Other than wanting me to be less rough, was there anything else?"

Kyle blinked at him, almost surprised for a moment. He didn't expect Randy to even ask him what he'd wanted, though it did warm his heart slightly to know that he cared enough. He thought for a bit, not really having anything else in mind besides letting the boar ravage him like he did last time.

"W-Well..." He looked down, his face blushing slightly, feeling a bit embarrassed that he was making a request.

"Yes...?"

"C-Can I be... spooned by you...?"

Randy chuckled and nodded. "You're just adorable, aren't you?"

Kyle blushed more and looked away.

"Lying down, or while sitting up?" He leaned in and licked his reddened cheeks.

"S-Sitting up..."

"Okay then." The boar repositioned him, helping him turn around while still sitting on his lap. He slipped his hard dick between the canine's plump cheeks, groaning at the feeling. His arms wrapped around him, pulling him back against his torso, his hands gently rubbing over the fox's chubby chest, drawing moans and whimpers out of him. "Like this...?"

He nodded back at him while he let out soft murrs.

"Good." Randy licked the back of his neck as his hands gripped onto his moobs, squeezing and groping them gently.

Kyle shivered from his teasing touches and licks, placing his own paws on top of the boar's and letting him play with his chubby chest. His fingers squished them before tweaking his thick nipples, pinching and drawing more pleasured moans and gasps from the fox. He wriggled back against the boar, grinding his cheeks against his massive throbbing cock.

"A-Aaahhh..."

"How's it feel?" Randy whispered sultry words to the fox, licking his neck more before giving it playful nibbles.

"G-Good..." Kyle let out a shuddery moan.

"Yeah...?" The boar squeezed his moobs harder and pinched his nipples between his skilled fingers.

The sensations made the fox squeal in delight, nodding back and pressing his hips against him, grinding the boar's hard member on his fat rear.

He chuckled and moved a paw to stroke Kyle's cheek, turning his head back slightly to meet his gaze. "God, you make such adorable sounds. Come here..." He leaned in closer and locked him into a deep kiss, sliding his thick tongue back into his maw.

Kyle moaned and whimpered, sliding his own tongue out and quickly began to swirl around Randy's. His paw kept stroking his cheek, keeping his head tilted as they kissed, while his other paw continued to grope his thick chest, cupping and grabbing onto them roughly. He then slowly moved it lower to rub his soft round belly, fondling it gently as well before sliding further down to grip the canine's hard cock, making the fox yelp and jump slightly.

Randy chuckled, pulling away from the kiss to whisper more teasing words. "Someone's all pent up..." He winked at him, lightly stroking his member, a bit of pre already oozing out from his tip.

Kyle blushed and playfully pressed his plump rump back on the boar's cock, drawing a groan from him. "Seems like I'm not the only one."

He grinned widely at him and licked his cheek. "Hard not to when I've got a sexy little fox sitting on my lap." He squeezed his moobs harder and made him yelp out in delight while his hips rolled against his fat rear. His hard cock slid between his fat cheeks, leaking copious amounts of pre and getting him wet and slick.

"A-Aaaahhh...!" He moaned out hotly, pressing back to meet the boar's movements and grinded his thick member on his rump.

"Mmmm..." Randy groaned and leaned in to whisper more teasing words to the fox's ear. "What do you wanna do next, hm?"

He panted softly, tilting his head back to look at him. "S-Suck... your cock... p-please...?"

"How polite." He let out a low grumble, pulling his arms away and letting the fox reposition himself. "Get to it then."

Kyle moved next to the boar, laying down beside him on the bed as he leaned closer to his member. He licked his lips at the sight of his fat cock throb and twitch, already slick with his pre. He wasted no time and began stroking it with his paw, bringing the thick tip to his lips to suck on it eagerly while swirling his tongue over it.

"Mmmm, that's it..." Randy gently patted his head, letting out more grumbles of approval as his cock spurted more pre into his maw.

He gulped it down and slid his thick shaft into his muzzle, bobbing his head and taking in an inch each time. All the while he swirled his tongue and slobbered his member with his drool.

"My, you're certainly more eager this time, hm?" The boar teased. He continued patting his head with one hand while the other went down to rub his back, stopping once he reached his plump rear and giving each fat cheek a soft slap.

The gentle smacks made the fox moan around his hard cock while he continued to suck him, drinking more of his thick pre.

"Mmhmm, my good little fox buddy. You love that cock, huh?" Randy teased more. His large hand groping Kyle's plump rear, squeezing it tightly as he slipped a finger between his cheeks and prodded his tight hole.

"A-Aaah!"

"I take it that's a yes?" He pushed the thick digit against his pucker, feeling it soon give way as it slid right into him.

The fox nodded as he continued to bob his head and lick his tongue over his hard throbbing member.

"You're much looser now too. Have you been playing down here since last time, I wonder." He continued to tease Kyle, thrusting his thick finger in and out of his hole, soon adding a second as he wiggled them both and stretched his insides wide around them.

He shook his head, moaning and panting more around his thick shaft.

Randy chuckled. His fingers grew more rough as he stuffed his hole harder and faster. "I guess you're just naturally loose then, huh? Or is that just a fox thing?"

Kyle didn't even respond. His mind was too busy focusing on sucking the boar's thick dick. His muffled groans and whimpers sent vibrations through his cock, eliciting more grumbles of approval from him as he stretched out his hole.

"Mmmm... I think that's enough." He gently pushed the fox's head away. His rock hard member throbbed and twitched, covered in both pre and drool. He tilted his head up with his hand so he could look directly at him. His bright eyes filled with lust glimmering down at him. "How does my little fox buddy want to get fucked?"

Kyle stared back at him, his own eyes gazing up to meet Randy's. The dark room was only illuminated by the lamp on the desk on the other side. He pulled away and slowly got on all fours on his bed. His fat rear wiggled at the boar as he reached back with a paw to spread his plump cheeks, showing his used hole.

Randy chuckled as he watched him get into position, kneeling behind the canine and lining his thick cock head to his pucker. "Damn Kyle, you really are eager tonight, huh?" He teased, prodding his hole with his member.

The fox nodded and panted out in reply.

The boar grinned down widely and pushed into him, though only stopping at the tip. "God, I love this ass." He gripped tightly to his plump rear, still just prodding him.

"I-I... l-love your cock..."

"Hm? What was that?" He teased, stopping his hips so only the tip was inside. "Could you speak up? I don't think I got that."

"U-Um... I-I..."

"Yes...?"

Kyle gripped tightly to the sheets as he spoke, his voice soft and shaky. "I-I love your cock..."

"You love what...?"

"I love your cock!" He repeated with a louder voice.

"Good." Randy smirked down at him, gripping his wide hips as he pushed more of his meaty cock past his tight hole. His insides squeezed hard around his dick, making him groan out. Each thick inch sank deeper until he was all the way in.

"A-Aaah!" Kyle moaned as he felt his insides give way to the boar's massive cock, gripping the sheets tighter while he panted and moaned out hotly.

"Mmmmph, taking this much better this time around." He chuckled. His hands rubbed his hips, going down to fondle his plump ass while he remained still, waiting for his insides to adjust to his size before he started thrusting.

"M-Much better..." He giggled, taking in deep breaths and relaxing himself as much as he could.

After a short while, the boar held onto his hips again. "Here I go. Don't worry, I'll go less rough as promised." His hips slowly pulled away from the fox, sliding his meaty cock out of him.

"O-Oooohhh..." Kyle let out a shaky moan as he felt the thick member move out of him until only half was in, before pushing it back into him.

It didn't take long for him to find a nice gentle rhythm. The canine's insides clung tightly to his hard cock, making the boar groan out in pleasure. His thrusts were slow and deliberate, dragging his large dick in and out of him, making him feel each meaty inch as it massaged his insides and grinded against his sweet spot.

"R-Randy... A-Aaaahhh..." The fox let out a mix of pleased moans and whimpers. His own hard cock leaked pre underneath him, staining his sheets.

Randy grunted in delight from hearing his name be called, looking down to admire the fox's body. His nice plump curves, his wide hips and love handles, the way his fat rear bounced and jiggled each time he thrusted into him. His one hand moved to rub his chubby sides as he leaned down over him to reach for his plump chest, eliciting a surprised gasp from him.

"You make the best sounds, you know?" He whispered into his ears, cupping his moob while still thrusting into him.

Kyle responded with more needy moans and pants. His voice grew louder as he felt the boar start to speed up and put more strength into his hips, slamming his fat cock into his hole.

"Yeeeaahh, just like that..." Randy started to play with his ears, licking them a couple of times before nibbling on one gently. His hand gripped tighter to his hip while the other squeezed his tit, his fingers tweaking his chubby nipple.

"A-Aaaahh, o-oooh God!" The fox yelped out in delight, his tongue rolling out of his maw. The sounds he were making grew even louder and more high pitched, mixing in with the lewd slapping of his fat rear smacking against the boar's hips.

Randy's thick member spurted pre deep inside Kyle, making his insides slick and wet as he continued to thrust his meaty dick in and out of him. His strong hips went into overdrive, soon pulling his member all the way out before slamming it back in. Their lustful grunts and moans mixed together and filled the room.

"Fuck... gonna cum..." He felt his load quickly build up as more pre leaked out of his thrusting dick.

"Y-Yes, p-please! Cum in me!" The canine yelped out happily, moving his hips in time with the boar's savage thrusts, his whole body bouncing and jiggling against him.

With a loud groan, his member spurted out thick loads of cream deep inside the fox. His hips still continued to slam his cock into him, each time shooting more and more of his cum in him as he filled him up.

Kyle panted and moaned in delight as Randy breeded him, his thick seed flooding his insides. His mind went hazy as it filled with lust, resting his head down on his bed.

The boar smiled down at the tuckered out fox, his hips slowing down to a stop as his orgasm died down. His hands rubbed over his back, lightly massaging his chubby sides. "How do you feel?"

Kyle nodded and gave him a thumbs up, unable to even lift his head and utter a response.

Randy chuckled. "Nice." He laid down next to him, repositioning themselves so they could lay down on their sides, his hole still stuffed with the boar's still hard cock. He wrapped his arms around the canine and pulled him into his loving embrace.

The fox panted and moaned, leaning closer to him as they snuggled. His paws gently rubbed over his strong arms, smiling at how gentle he held him.

The boar let out a low grumble as he held the canine close to him, nuzzling against his head and smelling his fur. His hands cupped his thick moobs and gently fondled them, squishing them against each other.

"A-Aaahh..." He let out a shuddery moan.

"Hehehe... you like having your tits played with, huh?" Randy squeezed his moobs harder.

Kyle replied with a loud yelp, nodding back at him.

He chuckled teasingly, his hands grasping his chubby chest as his fingers tweaked and pinched his thick nipples.

Playing with his body like that, combined with the adorable sounds the fox were making, aroused Randy once more. He grinded his hips against Kyle's plump rear and slowly started sliding his meaty cock in and out of his cum-filled hole.

"H-Huh...?" He gasped out, turning to the boar who had a wide perverted smile on his face.

"What?" He thrusted into him, squeezing his tits more. "You know I need to go more than once like last time, right?"

The fox's face turned red, nodding slowly as he remembered.

Randy chuckled. "Besides..." He removed one hand from his chest and brought it down to his hard canine cock, wrapping around it and stroking it. "Seems like you didn't get to cum yet."

Kyle blushed even more and yelped out, his member leaking pre on the boar's hand, stroking him off in time with his thrusts.

He grinned and put more strength into his hips, sliding his meaty dick in and out of his wet sloppy hole. Cum leaked out each time he pulled away before thrusting back into him. His hand squeezed his fleshy tit and pinched his nipple.

"A-Aaaahhh, R-Randy, I-"

Randy tilted his head to the side and kissed him deeply, cutting him off as he slid his thick tongue into him and wriggled it inside his maw.

Kyle's moans and whimpers were muffled as the boar slammed his thick cock into him. His chubby body bounced and jiggled from each hard thrust while his hands squeezed his chest and jerked off his member.

His hips grew more in speed and intensity, jackhammering his cock into Kyle like he did earlier. His hole made lewd squelch noises each time, churning the cum in him as it leaked out onto the bed.

Randy pulled away from the kiss and licked up Kyle's neck, making him shiver and moan out loudly. His tongue slid lower as he leaned his head down to the fox's chest, slithering it against his nipples before pulling one into his maw, biting and suckling on it.

"O-Ooooh!" Kyle yelped out in delight.

The boar chuckled from his reaction, sucking on his thick nipple. He moved his one hand to grip his thigh, raising it up so he could thrust his dick into him easier. With the change of angle, the tip of his member slammed into his sweet spot over and over, grinding onto it with each hard thrust.

He panted, moaned, and made all kinds of pleasure-filled sounds. His one hand gripped tightly to the sheets while the other held onto Randy's head, his toes curling up as he felt his meaty cock ram into him in time with his hand stroking his own hard member, and combined with his warm mouth sucking on his tit, his orgasm built up quickly.

"I... I'm gonna...!"

Randy smiled widely. Knowing exactly what he meant, he doubled down on fucking the hell out of him. His hips smacked loudly against his fat rear and ravaged his hot wet hole. His tongue swirled around his thick nipple before biting on it. His hand squeezed harder around the canine's member. All of them he did in perfect sync, feeling his second orgasm quickly build up as well.

"Gaaaaaah!"

Kyle let out a loud lustful cry as his cock started spurting out thick ropes of his cream, splattering all over the boar's hand, the bed, and on his torso. Randy didn't slow down however, continuing to thrust away and milk the fox's prostate and ride out his orgasm.

"Here comes another...!"

The boar quickly followed after, pumping him full of his second flood of cum. His hips grinded and slammed his meaty cock into his used hole as it shot his load deep into him. Each thrust shot more of his creamy load, swelling the fox's already chubby belly.

" A-Ahhh..."

The fox panted and moaned softly, resting his head down on the pillow. With one final thrust and a tired yet pleased grunt, the boar did the same.

"Mmmmm... Fuck, baby..."

His hips stayed hilted against his plump ass, wrapping his arms around the fox again and pulling him close for a hug while nuzzling the back of his neck. His hands gently rubbed over his body, giving his chest a few playful gropes before moving down to feel his cum-filled belly.

Kyle shivered as he felt it slosh in his tummy, moaning softly and reaching down to do the same. "So... full..."

Randy nodded, kissing his neck as he kept rubbing him. "Mmhmm."

He blushed a bit and let out a soft sigh, nuzzling against the boar as his eyes slowly closed.

They basked in their afterglow, cuddled up next to each other, the boar holding him in his arms while his hands idly rubbed over his chubby chest and belly.

Kyle nearly dozed off but was awakened from Randy rolling his hips and thrusting his hard cock in him.

"Again...?" He turned to him and was again met by the boar's pervy smile, nodding at him.

"The night is still young, babe."

Kyle gulped and smiled sheepishly at him. He wasn't surprised nor did he even try to protest. He did invite him, after all, and knew exactly what he was getting into.

The two fucked into the wee hours of the night. Their lustful grunts and lewd moans filled the room along with the raunchy noises of their flesh slapping against each other.

Kyle couldn't complain. He had longed for a night that wasn't just him pressing his nose against the books. It wasn't quite what he had in mind, but he'd be lying if he said he wasn't enjoying himself, and he was sure as hell Randy loving it just as much, if not more.