First Time for Everything

Story by StrangeBreed on SoFurry

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Roland belongs to RolandTheRabbit

Kay belongs to dilbertdog

Some other characters may resemble StrangeBreed and LobaDeLaLuna

Art by zooshi


All characters depicted in this work are purely fictional and over the age of consent. Any situation is meant as parody and does not represent any child, living or otherwise.

...

There was a great deal of hustle and bustle as a whole caravan of cubs seemed to flood their friend's house on Halloween, all carrying their own bundles and bags of candy. They all started to dance to various tunes and carry on about their conversations, giggles and cheers all filling the warm that was quickly turning quite hearty. One of the most social cubs seemed to be a young rabbit boy who was dressed as Colonel Mustang from Full Metal Alchemist. His fur was an almost pink shade with many blue details, his hair the same shade of deep navy.

He was quite the flirt, the young rabbit quickly talking to every girl he could find. He had talked himself up to just about every young cutie he could find before stumbling across a particular fur that really made his face lit up, another deep grin slowly curving over his lips. "Well hi there, happy Halloween!" he said brightly as he looked over the pretty German shepherd girl, her long brown hair the same gorgeous colour as her fur. She was dressed as Aqua from Kingdom Hearts, which only made her look cuter to Roland.

"H-hey, happy Halloween" she responded softly, looking down at the rabbit's offered paw.

"Roland" he said as she reached back out, bending down to tap the back of her paw with a kiss.

The shepherd let out a giggle at the silly kiss, nodding back as she offered her own name, "Kay."

"Kay," the rabbit repeated, eyes fluttering back at her, "...pleasure."

Kay's cheeks suddenly flushed red as she fell victim to the flirtatious rabbit's charm, struggling to come up with a good response. She had just opened her muzzle before a voice called out "Spin the bottle!" Kay breathed a sigh of relief as the party's host had saved her from the awkward conversation, though she did keep an eye on the cute boy as they departed from one another.

Every cub made a circle in the center of the room, the sheep in charge of the party setting a bottle down in the middle of the gathered group. "Alright, who doesn't know the rules?" the sheep asked, raising her eyes and smiling, "Everyone knows them? Cool, I'll go first then. Let's do this thing!"

Kay looked up as she saw that Roland had ended up across from her, the rabbit winking at her, which left her a shy mess once more. She watched as the bottle spun round and round before landing on a pretty young maned wolf, the pup trying to hide herself behind her long black hair as the sheep bounded towards her. "Wait..." a boy called out with sudden concern, "Does that mean boys have to kiss boys too?"

"Mhmm," the sheep said as she brushed her blonde pigtails back, diving her paws softly through the maned wolf's long hair to part it, "Who knows, you might like it!"

The young fox uttered out an audible "Fuck that!" before storming off somewhere else, the sheep ignoring him as she locked her muzzle tightly against the maned wolf's. Kay stirred in her spot uncomfortably as she watched their muzzles moved against one another, able to hear from the movements and the moaning just how passionate the kiss was. Kay felt something stirring deep within her, a slow building heat that stirred in her loins like wildfire.

All the boys in the room seemed glued on the sight of the two girls kissing, each breathing a sigh almost as heavy as the maned wolf herself when the kiss broke. The sheep looked into the other girl's eyes as her face flushed a deep red, lapping a string of saliva that connected her lips before whispering into her ear, "Mmm, you can sleep in my room tonight sweetie..." The maned wolf could barely utter a squeak before the sheep had stood up, looking around the circle, "Alright who's next?"

"I'll go!" Roland said with exuberant confidence, Kay cowering as she felt a mix of feelings. She was so anxious as she watched the rabbit get up to his feet, wanting so badly to run away from the game, while deep down needing the bottle to land on her. She watched as the handsome rabbit bent down, reaching out to grip the bottle carefully. He twisted his paw as he gave it one swift twirl, sending the bottle spinning over and over. It continued to make its slow rounds, each swing leaving Kay's heart beating wildly.

The shepherd watched as it eventually stopped itself, slowly aiming straight for her. She gulped nervously as she looked up towards the rabbit, the sheep next to him wearing a sly grin as she called out to the crowd, "Alright Roland, looks like you got Kay!"

The flirtatious rabbit wiggled his eyebrows as he made his way towards her, speaking in a very suave tone, "Exactly who I was hoping for!" Kay almost sunk away as the rabbit approached her, wanting to kiss him so bad, but so nervous to as well, especially with all the other cubs hounding around them. Roland reached out slowly and grabbed her paw, holding it softly as he looked her in the eyes, "First time?"

Kay gulped and shrugged, letting out some nervous laughter, "No... but I don't do this often."

Roland laughed as well, his smile soft and caring, "It's alright, I won't push you too fast." Kay took one more deep breath to steady herself, nodding to him firmly. "Ok, here we go!" he said in response to the confirming nod, leaning in slowly towards her muzzle. She felt her heart suddenly flutter as their lips connected, the kiss soft and gentle at first before Roland spread her lips apart with his. His tongue slid in gently and collided against hers, making slow contact before intertwining around the other smooth muscle.

Her eyes were wide open at first, but slowly began to close as the kiss became more sensual, both tongues sliding against each other rhythmically and smoothly. She felt the tingles in her heart grow wilder each passing second, her breath heavy against Roland's as she shook in the shared embrace. His paws gently brushed her arms as the pair kissed, both letting out content murmurs until their embrace finally broke. Kay looked up into Roland's eyes, stunned as all she could utter was a weak, "H-holy shit..."

The sheep in charge of the group continued moving the game forward, nodding to the pair with a big smile as she called out to all the other cubs, "Way to show them how it's done! Alright, who's next?"

...

The party continued on throughout the night and everyone seemed to be having their own marry fun. There was apple bobbing, video games and much candy binging, but Kay found herself uninterested in such things. She spent her entire night focusing on Roland, her eyes crawling over his form every time he would pass her. She would always give a goofy grin back to him whenever he noticed her, her legs shaking every time he would wave, wink or nod at her.

The night was halfway through when Roland finally approached Kay one on one again, stepping up to her as the group seemed to put a slow dance song on. He wiggled his eyes at her as he offered both of his paws, asking her in a very casual way, "May I have this dance?"

The shepherd blushed once more, but couldn't refuse, grasping the rabbit's offered paws gently as she got up to her feet, "Y-yes of course!"

Roland held her close as they moved towards the centre of the room, swaying to and fro to the rhythm of the music. "You're a good dancer" he complimented the canine on her skills midway through the song, her blushing a lot less frequent as her confidence seemed to be growing.

"Thanks," she said, trying to act a little cocky for the rabbit, "You're not too bad yourself." Roland said nothing at first, but his grin remained strong and sly. He waited one short moment before kissing her once more, his tongue sliding over hers as they enjoyed another casual make out session. Kay was a lot more into it this time and even pushed her tongue back against his, the two gripping each other tightly as they began to lightly grind. She kept kissing and grinding until something made her eyes light up, her paw reaching down to make sure she was really feeling what she thought she was feeling. "Oh..." she squeaked softly, Roland responding to her like a gentleman.

"Oh...th-that can happen, sorry, I don't mean to..."

"No," Kay said as she kept rubbing, her palm brushing over the bulge in the rabbit's pants, "It's ok... I like you, and I uh... I kinda wanna..."

"You... you do?" the rabbit was carefully calculated, the pair continuing to beat around the bush.

"Yeah, I mean... it's supposed to be special, you know? The first time, but Halloween is a special night right?"

Roland studied the canine carefully, enticed to oblige his pretty counterpart, but also wanting to make sure she really was ready, "Yeah it is, are you sure you're sure?"

Kay nodded, squeezing the bulge tighter, "Yeah I think so, but where?"

Roland wracked his brain as he so desperately wanted to make things work. He thought about asking the host of the party, but she was nowhere to be found. He finally grabbed her paw and gave it a tug, coaxing her to follow him towards the stairs, "Follow me, we'll find a place!" Kay simply nodded in return, following the rabbit wherever they had to go.

They quickly travelled up the stairs, looking around at the four rooms they had options to. The first they checked was the bathroom, not ideal but possibly could be used as a last resort. The second door led to an immediate eyeful, both Kay and Roland wide eyed as they peered in. From the amount of pink in the room, it clearly belonged to the sheep girl who was hosting the party. Her white fur was all on display as she was crouched over on her bed, her soft pink folds up in the air as she remained naked, leaning into the naked maned wolf. The other girl was laying back on the sheep's bed, moaning and howling as the sheep kept lapping at her soaked folds.

The sheep turned to look at the two intruders, nowhere near concerned at what they were seeing. She seemed more irritated than anything, pinching the nipples of the maned wolf to keep her excited as she spoke, "Can I help you?"

"Umm sorry, we uh, were..." Roland struggled to find the right words, the sheep guessing before he had to stumble on any further sentences.

"Trying to screw? Go use the spare room, it's on the left."

"Th-thanks" was all Roland could say, surprised at how casual the sheep was.

"Uh-huh..." the sheep trailed off without much concern, her lips going right back down on the maned wolf.

"That was... wow!" Kay said with a big laugh, the rabbit chuckling with her as well as they found the room they were looking for.

"You're telling me! Alright, this looks like the place..." The room had been furnished for the sake of the holiday, fake skeleton and all. A jack-o-lantern was resting on the bedside table and they were candles all about the room. A spider web bed sheet and fake spiders and bats on the curtains and walls. "The Baileys really go all out!" Roland thought aloud as he surveyed the room, going quiet all of a sudden as he felt the shepherd's paw return to his crotch.

She gulped nervously as she worked up the courage for her next question, looking at him gently as she spoke, "M-may I see it?"

Roland nodded as the canine dropped her butt down on the bed, standing in front of her as he fiddled with the zipper, "Y-yeah..."

Kay waited what felt like eternity, her eyes lighting up as the big cock flopped out. It was already semi-hard from the rabbit's anticipation, a single drop of precum dripping from the slit as she touched it with her paw. "Oh wow!" she gasped as she stroked it slowly, looking up as if to ask, and receiving a nod in kind from Roland.

She reached for it slowly, her tongue moving in smooth circles over the cockhead, collecting the salty droplet off the slit as she went. She carefully grasped the shaft firmly before fitting the first few inches into her muzzle, trying to be as careful as possible as she copied the technique she had seen in so many videos online. "Ahh, yeah! Just like that!" the rabbit moaned out as he felt the damp warmth surround his length, inch by inch the cock slowly being buried into the beautiful canine's throat.

She kept her lips wrapped around the shaft as she began to bob her head up and down, only having to stop occasionally as the rabbit winced. "Sorry!" she called out before swallowing it back down, knowing she had given teeth a few times.

"It's ok," the rabbit said with a smile, petting her hair as she bobbed her head up and down, "You're new at this." He lay his head back as she kept sucking him off, letting out a long, satisfied groan before speaking again, "It's hard to tell though, you're really good at this!"

Kay looked up at him cutely, giving one more long slurp over his shaft, "I-I am?"

Roland nodded once more, letting out a long exhale as she began bobbing her head up and down even faster, "Fuck yeah, mmm, stop, stop, stop!"

There was a look of concern on the shepherd's face as she came up from sucking him off, cocking her head to the side as she asked curiously, "Did I do something wrong?"

Roland chuckled almost harder than before, shaking his head as he spoke back, "No, no trust me, you're great it! Just a little too good, I don't wanna finish until..."

Kay's eyes lit up, "Oh yes of course!" She reached for her own pants as Roland kicked his off, shoes on the floor as well as he was left wearing just the top half of his costume. "I-I hope it's ok" the canine whispered shyly, slowly revealing the lower half of her body to the rabbit.

His eyes lit up as he studied her beautiful body, paw touching her soft folds until she shivered, "Mmm, it's lovely!" He looked in her eyes and kissed her one more time, nodding to the bed she sat on, "Lay down for me beautiful!"

Kay gulped a little anxiously, but nodded nonetheless and lay down as suggested, "A-alright."

She let out a rough yip as the rabbit suddenly hooked his arms around her legs, spreading her out more so he could get an even closer look at her wet pussy. He slowly inched closer with his muzzle, giving a nice big inhale of her scent before sliding his tongue over its sweet surface. Kay already began to moan quite loudly, shaking as the tongue wiggled all over the most sensitive spots on her young body. "Mmm, you taste so good!" Roland mumbled out as he sampled her feminine nectar, loving the sounds that were coming from her.

Kay had her fingers tangled tightly in the rabbit's hair, grinding her pussy against his lips as she felt more pleasure than she ever had before. "This feels so, s-so-oh god!" She let out a loud shriek as the rabbit began suckling at her clitoris, the shepherd's legs shaking wildly as she coated the rabbit's muzzle in the juices of her arousal.

"Mmm!" Roland moaned out, still slurping away at the sweet pussy as it got wetter with each passing second. He would let his tongue slide over the surface of her entrance before moving to the sides of her soft petals, letting his tongue linger over them before going for the clit once more. He kept up the pattern with a steady rhythm, soon leaving the puppy a whimpering, near exhausted mess.

"Stop!" the canine suddenly howled out, the rabbit looking up with concern.

"Did I do something wrong?" the rabbit asked, noticing the sly grin on the pup.

"No..." she began to repeat the exact same wording from earlier, "I just don't wanna finish until..."

A wicked grin curved onto the rabbit's muzzle and he hopped up onto his feet, helping the shepherd up and moving her into a new position, "Alright let's do this!"

"How do you want me?" Kay asked.

"How about doggy style? No better way for a dog to lose her virginity!"

Kay laughed but agreed, "Alright, sounds good." She got carefully into position and closed her eyes, wincing a bit as she felt the tip of the rabbit's cock poke at her pussy.

"Don't worry, we'll do this slowly" the rabbit assured her, simply teasing around at her slick entrance to start.

Kay waited the long anxious wait until the rabbit finally dropped forward, a pop audible as stings filled the lower half of her body. Kay squealed out as her entire body shuddered, her breath all heavy and gasped out as the cock slid in and out of her a few times, "Ok, that hurt!"

"I'm sorry" the rabbit said earnestly, but was happy to see the canine was still aiding in his slow thrusts.

"It hurt," the canine elaborated, "But not as bad as I thought it would!" She waited until the stings edged off, the sliding of the rabbit's shaft slowly starting to turn very pleasurable. "Ooo that feels nice!" she said with a sigh, not able to see the vicious grin on Roland's face from her angle.

The rabbit slapped her tailcheeks playfully before pulling his cock back a bit, "You ain't felt nothing yet!" Kay's eyes raised curiously at his words before she felt him suddenly drive his length back in, the rabbit soon thrusting hard into her. He began pounding her raw, the previously untouched parts of her body igniting with a fire of pleasure.

"H-holy shit!" she squealed out, yipping and barking as the rabbit's cock hit the deepest parts of her. He thrust over and over with no signs of slowing down, the shepherd letting out a long shudder as tingles filled her entire body. "This feels so good!" she cried out in ecstasy, her tail wagging wildly as her pussy remained completely receptive to the heavy thrusts of the rabbit's shaft.

"You're telling me!" the rabbit moaned out, the damp warmth of the canine's pussy constantly hugging his throbbing length. She had bled a small bit with the breaking of her hymen, which served to only make the screw even wetter, something that despite strange in nature, felt very good.

He kept pushing in and sliding out, the pussy soon clutching tighter as the shepherd dealt with a few fast and strong climaxes. She was leaving his cock soaked and sticky, the sound of her voice showing how weak she was getting, "I-I'm sorry Roland, I don't know how much more I can take."

The rabbit shook his head as he kept thrusting, hitting her depths with each pound as he groaned out, "Don't worry, I'll only be a, a-nother, s-s-yeah!" He let out a loud moan as he fired a thick load of seed into the canine, his balls tightening until every last shot had fired out.

At once the pair dropped down overtop of each other onto the bed, holding each other softly as the rabbit began lapping the canine's cheek. Kay giggled as she felt the soft tongue rub against her face, whispering to the rabbit in her gentle state of afterglow, "H-happy Halloween!"

Roland smiled as he clutched her tightly, replying with the exact same sentiment, "Happy Halloween!"