The Sleepover
“Are you sure you don't mind watching him, Dave?” The question, asked for the thousandth time that week, was, as it always was before, answered with a smile and a laugh as Dave Seville nodded. The man asking peeked around his friend at his son, the banana coloured corgi currently passing through the kitchen as Simon showed him around the house.
“I already told you I don't mind, Adam.” He patted the older man on the back as he sighed, relieved. “Teddy's already proven that he's an angel―besides, it'll be good for him to spend some time with the boys. Help him open up a bit.”
Adam nodded, a soft smile on his face as he thought about that―Teddy used to be such an outgoing, adventurous boy... at least until they'd moved. Maybe being around the chipmunks would help bring him back out of his shell, especially with how Alvin tended to be. “I'll be back late Monday night, but if I can manage to get home sooner...”
“Don't worry so much. He's going to be fine, I promise. I think you're more nervous than he is at this point.” Dave laughed and Adam followed in suite. Dave was right, as usual. “Boys, come say goodbye.”
Teddy ran back into the kitchen and tightly wrapped his arms around his Papa's leg. Adam lifted the puppy into his arms, hugging him close and planting a kiss on his forehead. “You be extra good for Dave, alright?” Teddy nodded, ears folded back as he stared up with wide eyes. Of course he'd be extra good. “It's just a couple of days. You're going to have a lot of fun and I'll be back before you know it.”
Simon and Theodore were next to the kitchen, though Alvin trailed in close behind, a grin on his face. “We'll take good care of you, kiddo. It's gonna be a blast.” Teddy looked to Alvin, and knowing the chipmunks particular reputation at school, bit his lip nervously, looking to the other two for help.
“Eheh...” Simon slapped Alvin on the back, giving him a look that clearly said 'behave'. “Don't worry. We won't let Alvin get too crazy.” The corgi nodded and reluctantly let go of Adam, allowing himself to be placed back on the floor. Theodore immediately took the corgi's hand, and the pup stood close to him. “Have a good trip, Mr. Winters.”
“Don't work too hard! And make sure you get lots to eat and lots of rest, okay?” Theodore added in with a smile. “Teddy's gonna be okay. I promise.” He gave Teddy's hand a reassuring squeeze as the four boys stared up at Dave and Adam.
“Thank you, Theodore, Simon.” Adam smiled once more. “Behave, Alvin.” Taking a deep breath, he shook his head and gave them all once final look over. “I love you, kiddo. I'll be back soon.”
They watched in silence as Adam retreated from the kitchen, slipping on his coat before glancing back, just in time to see Teddy whisper, “I love you too, Papa.”
It was hard, leaving his little one behind, but he didn't have a choice, not this time, and Dave was the only person in the area, aside from Mrs. Miller, that he felt he could trust with Teddy, but considering the circumstances... he felt his pup would be a little more comfortable spending the weekend with the boys over the girls.
One more deep breath was taken as he climbed into his car. The plane was leaving in an hour and he wanted to get there as quickly as possible. The sooner this job was done after all, the sooner he could get back home.

ooOoo

Teddy had this look on his face... his eyes were still slightly widened, the slightest hint of moisture visible, a soft pout on his face. He looked like he was going to cry, which to Dave, would have been completely understandable. From what he'd been told, the pup hadn't spent a single night away from his Papa since they'd moved into town a few months prior and being shy as he was, he wasn't exactly... friends with his own boys.
Dave though, had bonded immediately with Adam, and though it was originally only because he was, like Dave, the father to a... special child, they'd turned out to have much in common, becoming fast friends. Dave even, upon learning of Teddy's newfound shyness, was the first to suggest getting the kids together.
It had seemed to be working, albeit slowly. Having Teddy over to spend the night with them so soon though... it was likely to be overwhelming. But, he didn't cry, not one bit. Instead, the little yellow dog took a long, deep breath, before turning to Simon, his hand still wrapped in Theodore's. “Tour?”
Ah, right. Simon had been showing him around the house properly before Adam had left. “Of course! Although, all that's left is our room and the bathrooms... but let's get it out of the way so you can get settled in.”
The corgi followed closely behind Simon, his hand still wrapped in Theodore's. “Alvin.” The red-dressed chipmunked looked up at Dave as his brothers left the room, curiosity written in his features. “Please, please promise me you won't do anything to scare him. It's going to be hard enough for him to be away from his father without you causing trouble...”
“Trouble? Me? C'mon, Dave, you can trust me.” Alvin grinned wider, but Dave just stared him down. “Okay, okay. I'll be nice.” The chipmunk rolled his eyes, shuffling out of the room as he grumbled about 'stupid babies' under his breath. Just this once, Dave let it go, not wanting to get the rowdiest of his boys riled up this close to bedtime.

ooOoo

Once the tour was over, the touring trio retreated to the bedroom, Simon sitting at the edge of his bed while Theodore sat beside Teddy on the floor. “I know you brought a sleeping bag, but if you want... you can share my bed. There's enough room and that way you don't have to sleep alone.” Theodore gave the corgi a smile which was shyly returned, though the pup's tail was wagging with excitement.
“Are you sure? I mean... I'd like that, but I don't want to be a bother..”
“I'm definitely sure! I always sleep with my Teddy anyway, so I'm sure that sleeping with a real Teddy will be even better!” Teddy giggled and nodded―he hated sleeping by himself anyway, always sharing a bed with his Papa.
“Aww, what if I wanted to sleep with Teddy?” Alvin spoke up as he entered the room, an obviously fake pout on his lips. “He'd keep me extra warm.” The smile that followed his words had Simon's cheeks glowing and he threw a pillow at Alvin, who easily dodged, sticking his tongue out at his brother.
“We can all sleep together!” Theodore piped up with a grin, oblivious to Alvin's intentions. “We can take all the blankets and pillows and get the extra ones from the closet. It'll be like a campout, just in our room!”
The corgi was grinning as well now, wiggling as he tail continued to wag. “Can we do that? Please, Simon?” The older chipmunk sighed softly, smiling. 
“I'll go ask Dave to get the blankets down.”  The pup silently cheered and shuffled to his overnight bag, a cute little dinosaur print backpack, and started digging around. Usually he slept in a pullup and a pair of feetie pajamas, but he was being a big kid now, so a pair of Dino-RAWR briefs and a teeshirt were his nightclothes of choice.
With a smile on his face, he stripped out of his shirt and pants, not caring at all that he was being stared at... at least until Alvin spoke up. “Wow.” Teddy's ears flicked as he glanced over at him. “Pretty cute~” Teddy smiled awkwardly, but went about getting dressed... turning away from Alvin and Theodore.
His old underwear (Power Ranger themed), were slid down and off and as he bent over to pick them up-- “There's a heart on your butt!” Alvin, again, though this time Teddy yelped quietly, trying to cover the fur pattern with his paws.  “Aww, c'mon, lemme see. It's cute.”
Hesitant, though now really wanting to be dressed, he removed his paws, tail flicking as not one, but two chipmunks got full view of his bottom―which did in fact have a cream upside down heart shape on it. “That is so cute. It's a perfect heart shape!” Theodore added in, giggling, and Teddy's face burned red as he quickly tugged up his new underwear.
Thankfully, Dave chose that moment to enter the room with Simon, carrying an armful of blankets and pillows. He laid them out for them as well, making a large, fluffy pallet for the boys to sleep on. Alvin plopped down first of course, after stripping out of his shirt and head, spreading out with a content sigh. “Alright you guys―Goodnight and sweet dreams. I'll see you all in the morning.”
“Goodnight, Dave!” Was the collective response as he left. The room was quiet for  a few minutes after that while Theodore and Simon got ready for bed―Simon being the only one in actual pajamas, while Theodore chose a teeshirt and briefs like Teddy.
Simon listened at the door for a few moments before shutting it, the lock clicking in place, the lights flicked off. They all lied back, Simon to the left, followed by Theodore then Teddy, and finally Alvin. 
Knowing it was time to put their plan into action, Alvin smiled, an unseen grin as he scooted closer to Teddy, wrapping an arm around the pup's belly and giving him a squeeze as he snuggled as close as possible, pressing his crotch against the corgi's bottom. Happy for the warmth and attention, Teddy's tail began to wag.
“Hey, Teddy, I have a question for you.” Alvin spoke low, hand softly rubbing the roundness of the corgi's belly. “You're a dog, right?” He nodded, tail wagging faster, his butt wiggling happily. “So... do you have 'parts' like a dog?” 
“Alvin!” Simon hissed out, having hoped his brother would approach the subject with a little more tact. “That is an inappropriate question―leave him alone.” 
“I'm just curious.” Alvin shrugged, continuing his rubbing, his hand making it's way lower and lower. “So, do you? I mean, have like.. a sheath and stuff? Like a normal dog?” Teddy nodded, mumbling out an 'mhm' as his cock began to twitch in said sheath, Alvin's hand trailing over the waistband of his briefs. “Can I see?”
It was the moment of truth―Theodore's eyes wide as he watched, staring at Alvin's hand. Simon bit his lip, hoping, curious, but still worried. What if Teddy got scared or freaked out? What if he told Dave? They'd all be in so much trouble, he'd never be allowed back over-- 
“Y-Yeah..” Oh. Well then. The corgi rolled onto his back and tugged his briefs down slowly, just enough to expose his sheath and balls. “See?” The fur in that area was a rich, chocolate brown colour, contrasting against his cream and pale yellow, and Alvin smiled wide. “I know it looks kinda... weird... but my penis is in there...” 
Taking this as a sign that the plan was definitely a-go, Theodore joined in, sitting up as he shook his head, softly patting the pup's sheath. “It's not weird at all. Everyone's is different, you know. Look.” The chipmunk tugged down his own briefs, revealing a set of cream coloured balls and a short, but thick cock, hidden inside it's foreskin. He wrapped a hand around it, tugging the skin back to reveal a light pink head. “Mine hides too.” Teddy nodded, resisting the urge to lick his lips as he stared.
“So, your penis is inside of there?” Teddy nodded at Alvin's question. “Can you make it come out?” 
Though he opened his mouth to respond, Simon beat him to it, clearing his throat as he scooted forward. “If I may--” He reached forward with a shaky hand. “With dogs.. their penis comes out more when they get... excited..” One hand took hold of the sheath, and he gulped as he felt the hidden cock throb inside. “I imagine it's a little different for you, but...” Simon's other hand cupped his balls, softly rubbing and squeezing them as he began to work the sheath.
Teddy didn't resist his actions, and he began stroking harder, the tip of the corgi's red cock peeking out. “T-That feels...” He panted, watching Simon, his ears drooping back.
“Good? It's a good feeling, don't worry.” The pup nodded, biting down on his lip. “Theodore―wanna.. help me out a little?” The chubby chipmunk nodded happily and took hold of Teddy's cheeks, pulling him into a soft kiss. It was a technique that always worked on Alvin and Simon and though it was different with Teddy, the corgi whimpered, and he knew he'd made the right move. Theodore's tongue made it's way into the corgi's inexperienced mouth, and his padded hands gripped Theodore's shirt as he tried to mimic the chipmunk's movements.
As his arousal grew, his cock slipped further from it's sheath and he squirmed, “S-Simon--”
“You're fine, Teddy. Just trust us.” Alvin gave him a smile as he pulled him away from Theodore and into a kiss of his own, rougher, needier. He sucked on Teddy's tongue, moaning as he slid his hands under the pup's shirt, which Theodore helped him to take off before sliding down, taking over Simon's position as the older chipmunk stepped back.
Licking his lips, he took hold of the sheath with one hand, dragging his tongue along the underneath, and over the tip. Teddy shivered hard, groaning into the kiss, thrusting into Theodore's waiting mouth, cock now fully exposed, pearls of pre-cum slickening the length. The knot though, caught Alvin's attention and he broke the kiss. “Oh, I gotta try that. Theodore--” Said chipmunk backed off as Alvin nodded. “Do you trust us, Teddy?” The corgi just nodded, wanting more. “We're gonna play a little game, okay? Just do what I say.” Another nod.
Alvin tugged his underwear down, tossing it off to the side before flipping over onto his hands and knees, spreading his legs to expose his hole. “I want you to use your tongue―get me nice and wet.” When Teddy hesitated, looking to Theodore, the chubby chipmunk smiled, gently leading Teddy's head closer to Alvin's ass. 
“Just lick, okay? Lots and lots, right there.” Theodore pressed a finger to Alvin's hole, only just dipping in, and immediately, Teddy started lapping at the area, pressing hard with his tongue. “Just like that―inside too. Make sure he's really wet. I'll do it to you too, so you know how it feels.”
Simon stayed to the side, one hand dipped into his boxers, wrapped around his cock. He bit down on his lip as he stroked himself, watching his brothers and their guest. In a sense, it felt wrong, it was wrong... Teddy was innocent, especially compared to them, but he was falling so easily into the roles they wanted, his muzzle buried deep in Alvin's ass, tongue eating him out as Theodore did the same to him. The corgi's tail was wagging constantly and his cock was exposed completely, bouncing with the movement, slick pre dribbling from the tip.
Alvin hadn't stopped moaning since he started, his hands gripping the blanket below him, cock throbbing as he tensed, already coming close. Theodore was nearly the same, always most excited to be using his mouth for something, whether it be rimming, a blowjob, or even just licking and sucking on his brother's necks, ears, nipples. 
Simon began stroking himself faster, trying to bite back his moans, but Alvin glanced over, staring at him knowingly as he moaned louder. “O-Okay, Teddy..” The chipmunk panted out, “I want you t-to put your hands on my hips. “Which was done quickly, his little claws pressing against the flesh. “Now put the e-end of your cock―penis where your t-tongue was..” Teddy carefully did so, pushing just the very tip inside of Alvin. “S-slowly push i-inside..”
Again, he did as asked... at least at first. When Theodore's tongue buried itself inside of his ass, he jolted, and shoved as far into Alvin as his cock would go, his knot pressing against the tight hole, and Alvin had to bite down to stop from yelling out. As Theodore's tongue worked inside of him, Teddy thrusted back on it, thrusting into Alvin as he did so.
“You like that, huh?” Theodore asked as he pulled back, and Teddy nodded, whimpering at the emptiness. “I bet you'll love this..” He wrapped his arms around Teddy and in one quick movement, thrusted his cock all the way in. No whimper or cry of pain, just a loud, growly moan as he pushed back on it. “Try and keep up, okay?” Theodore started thrusting with earnest, and Teddy copied him as best he could, body shaking. The sensations were almost overwhelming.
“S-Si--” Alvin stuttered out, “C-Come on-- let me taste y-you..” Simon scrambled over quickly, tugging his bottoms down just enough to expose his cock, which Alvin greedily took into his mouth and began sucking down. Allowing Alvin to suck off the third of the chipmunks, Teddy pulled him into a kiss, and Simon complied, watching from the corner of his eye as Theodore bit and nipped at the pup's neck and shoulders.
Theodore grunted as his thrusting picked up and he bit down hard. Teddy growled, matching his pace and as they brought Alvin to the edge, he sucked harder―Simon was the first to come, and he gasped into the kiss―Teddy not letting him go--as he thrusted hard into his brother's mouth. Alvin swallowed down every drop.
Teddy tensed up as he got close, and he growled again, thrusting harder―once, twice, and with a pop and a strangled yelp from Alvin, the knot slid into the chipmunk's ass. As it swelled and cum began to shoot into Alvin, Teddy tugged and thrusted much harder and faster than before. This caused Theodore to cum as well, inside of him with a groan as he tightened his hold on Teddy. Alvin followed in suit, his own cum spraying onto the blanket below as he clenched around the knot.
Theodore pulled out and sat back, panting heavily as he watched Teddy and Alvin―Simon, now released from the corgi's grip, sat back as well. “O-Okay―that..t-that was.. awesome..” Alvin pulled forward a bit, then stopped. “I―are you―are you stuck?”
Letting out a heavy,contented breath, Teddy nodded, getting into a slightly more comfortable position. “Didn't you know that dogs tie?” The corgi asked with a smile, tail wagging. “It uh.. I can't pull out until my knot goes down..”
Theodore tilted his head, scooting around to see. “So you're stuck like that? For how long?” 
With a shrug, the corgi patted Alvin's bottom. “Only a few minutes. If I was bigger, it could take up to halfa hour.” Alvin tensed up at that, then sighed, thankful that it wouldn't be that long. “Is so that when a boy and a girl mate, all the stickies get stuck inside so the girl will have puppies.”
All three chipmunk's stared (attempted to) at him, brows furrowed in confusion. “Wait, so, you know.. about this kind of stuff? About...” Simon trailed off, and Teddy nodded.
“Yeah! I used to play grown up games all the time at my old school. But I got told lots of that cause I'm so small, I look really young so people liked it when I pretended not to know.” Theodore giggled and Teddy smiled, tail wagging.
“Aww, and here I t-thought we were corrupting y-you.” Alvin stuttered out, shuddering as Teddy's knot throbbed inside of him. “R-Ruin my f-fUUuuuuN--!” He groaned out as Teddy tugged back. “D-Don't do that--”
“Relax, I just wanna see if I can get I out..” Teddy mumbled back, wiggling as he continued to tug. Alvin was moaning and whimpering underneath him, but after a few moments, with a sloppy 'pop', the knot came out, and the thin puppy cum dripped out after it. Teddy didn't waste any time in lapping up all the cum that he could find, even dipping his tongue back into Alvin's hole to slurp up what he could.
After which, he cleaned off Alvin's cock and the cum that pooled beneath him, before letting him collapse into a tired heap on the pallet, breathing heavily. Teddy crawled over to Theodore next, cleaning him off as well, and though Simon was hesitant, he allowed the corgi to lick him clean too. The top blanket would need a serious washing, but now it wasn't quite as bad as it could have been.
Tired, happy, his belly and butt full of cum, Teddy tugged his briefs back on and flopped back against the pillows, sighing. Simon was quickly redressed, and Theodore tugged his own briefs back up before helping Alvin, who didn't want to move. “Did you guys plan this?”
Simon sighed, smiling embarrassed as he rubbed the back of his head. “Yeah... it was Theodore's idea though.”
Said chipmunk nodded, lying next to Teddy. “You're just so cute. I knew you'd be a lot of fun to play with... did you have fun?”
“Mmhmm.” Teddy grinned with a smile, watching as Simon and Alvin took their places on the pallet (Alvin a bit more slowly), before closing his eyes. “We definitely gots to hang out more often.”
Alvin's snoring was the next thing they heard, which earned laughs from the remaining three boys. “As always.” Simon mumbled, shaking his head in amusement. Goodnight Theodore, Teddy.”
“Goodnight, Simon.” The chubby chipmunk and pup spoke at the same time, letting out little giggles as they got comfortable. The room was quiet, and it didn't take long for Simon's breathing to even out, signaling that he too was asleep.
“Hey Teddy.” Theodore whispered and the tired corgi opened his eyes once more, just in time to see Theodore press one final kiss to his lips. “Goodnight.”
Teddy smiled softly and cuddled up to the chipmunk, “Goodnight, Theodore.”