'Why Theodore... Really, what was I thinking?  I coulda taken Simon first, but nooooo.  Why did I pick Theodore!?' Brittany thought. She had gone back into the living room with the chubby chipmunk, now sitting in the recliner chair with him. She was naked, while he was still in his usual green jacket.  Not that it hid much. 
His fur was standing on end, making him look like a little ball of fluff wrapped in his jacket, eyes wide and nervous as he stared back at her.  'He's hard as hell, and somehow he's still acting timid...' she thought. He didn't have… much of a package downstairs, but hey, he looked big enough to make sure the job was done. And that was enough for Brittany. 
Now, if only he didn't look like he was ready to piss himself any time she moved.
Brittany sighed. “You know, Theo, I don't blame you.” She started.  “It’s our first time, you… probably haven't seen us naked before, unless you peeped, and you definitely wanted Eleanor and not me.”
'If this is gonna work... I'm gonna have to calm him down.' She thought, nodding in confirmation while getting up to her feet. Theodore was trembling visibly as she approached him, crouching down at his side. "Hey, Theo?”  She reached and put a paw down on his wide stomach and started rubbing it.  
Theodore looked like he’d scream, but Brittany moved quickly and covered his mouth with her paw. "Hey, hey, no, none of that." She said gently, but sternly, moving her paw beneath his jacket now, gently scratching through his tummy fur. 
When he nodded his head, Brittany continued. "We're… friends at least, aren't we Teddy?" She asked, hoping the nickname would make him relax.
"Well, uh… Y-Yes… We are.” He answered softly, his cheeks blushing as he laid his head back against the recliner's arm, ears laying flat. "Oh gosh, I'm s-so sorry I'm acting like this, I'm not used to this kind of stuff…"
“You and me both, little guy. Er, kinda.” Brittany smiled, nudging his jacket up his body a little, leaving his entire belly and chest exposed soon enough. "Buuut, we're gonna be more than friends now. And that means you don't have to be so scared."
What an innocent little ball of fur... It was bad enough Brittany's crotch was on fire, but seeing the way his penis pulsed and throbbed and leaked was making it worse. Every last part of her was demanding that she just… jump him.  Pin him down, cram him in raw, and ride him nonstop until he was squealing and filling her as much as he could!
Brittany squirmed at the thought, reaching a paw down to rub along her pussy. No… She couldn't pounce on him. If she did, she'd probably traumatize the poor thing.
"Tell me... What's something you like to do to relax? Other than eat, of course." The mention of "eating" definitely made her loins quiver.
Theodore looked off to the side, biting down on his lip. "Well... I-I feel calm when we're performing. Or at least it's just not scary." He says softly, his fur starting to lie flat again.
"Hey, that's a start!  Here, let's get that off you." Brittany said as she grabbed the hem of his jacket once more. Theodore raised his arms over his head, letting Brittany remove his jacket completely, then tossing it to the side. "Hmm... I have an idea." Brittany spoke, helping him back up to his feet. "How's about... You do a little performance, just for me? Do whatever you'd like as long as you're comfortable with it." She encouraged.
Admittedly, the thought of the chunky munk showing off what he had was a lot more enticing than usual.  ‘Anything to get him going, Britt.  Just go with it.’
Theodore nodded his head, his tail swishing side to side as he thought. Then, he gasped, eyes wide again as an idea hit him. "So, uh, I think stuff like this is usually hot, right?" He asked as he went to the arm of their shared seat.  He bent over it a little, his tail curling upwards as he did so. 
Brittany's cheeks darkened, her gaze focused intently on his rear. What else could be expected from someone who ate a lot? His butt was nice and plump, jiggling about whenever he moved around. This wouldn't have turned her on, normally… but here she was, almost licking her lips, the heat of desire getting stronger between her legs. As much as she wanted to just finger herself, she found herself nearing him, grabbing his butt with both paws and squeezing it firmly.
Any other day, she would have never even considered looking at him there. Now, though… the way he just squished in her paws made Brittany shiver.  Theodore let out a little moan as she felt him up, and Brittany leaned in to kiss his cheek. 
"Theodore…. Shake it for me~” She whispered in his ear. Theodore tensed up, but nodded his head, his body trembling as he pushed his butt closer to her paws. 'Heh... Here comes the show.' Brittany squeezed his butt once more, then scooted back to give him room, a paw still between her legs as she watched him. Theo started simple, gently swaying his hips from side to side. He peeked back at Brittany, his usual sweet smile forming on his face again as he got into the motion.
Now the real fun could start.  “Remember~. Just move and groove however you’re comfy!”
Theodore looked back at her with a newly confident nod, getting down on all fours as he continued to work his stuff.  
"Hehe, go Theo, go!"
It didn't take very long for Theo to get into the swing of things. Almost instantly, he went from a terrified puffball to an eager little performer.  He held onto the recliner's arm for support, humming a little tune to himself as his hips swayed to his rhythm, that pudgy rump of his bouncing almost hypnotically.
Brittany licked her lips as she watched his little show, laying back against the chair's other arm, fingers buried deep in her needy slit. It wasn't what she was expecting, but she wasn't passing on anything he could offer. If that meant a show of his fat ass quaking around like nobody’s business, then it'd be enough. Besides… he really did look nice.
Her arousal grew when Theo's tail swept off to the side, revealing his little pink entrance. He looked back at her again, a blush nearly visible on his chubby cheeks as he pokes his tongue out. "You want it?" He asks, reaching back to give his ass a firm smack. 
"Heh. You have no idea." was her reply. 
‘Come on Brittany…!  Just do it already!’ She thought, pushing her fingers in more with a shaky whine.  ‘You want it, you know you do, so get in there!’
Biting her lip, Brittany forced herself to move her paw, grunting as she rolled onto her belly, crawling towards Theo, desire filling her stare. So many ways to make him squeal… "Lemme… try something.  Gah, can’t believe I'm doing this, but..."
Her soaked paw went between his legs, grabbing his shaft firmly at the base. "M-My thing! Brittany, what're you-"
"Ah ah ah.” She gave his rear a good slap with her other paw, causing it to jiggle and making Theo yelp. “Don’t you even THINK about stopping, mister~” Theodore squeaked in surprise, his hind claws digging into the cushion below as he looked down at Brittany.
“Y-You didn't have to spank me…” 
“Didn’t you just spank yourself~?” Brittany countered, grinning up at him as she gave the spot a soothing little touch before letting his butt go.   
Theo whined, reaching back to rub the stinging spot on his rear. 'Why did it feel so… good when she did that?'. Sure, when he hit it himself he didn't notice much, but when she did it…? He shrugged a bit, then started to shake his butt again, biting his lip. The movement caused him to work his tender shaft against Brittany's paw, and it made his body quiver in bliss.
He only got louder as her thumb started to rub up against his tip; the most sensitive spot for him. "B-Brittany, not there, pleeeease!" Theodore whined, claws starting to dig deep in the material of the chair. He had no choice but to continue, panting heavily as he wiggled his hips, driving his tip against her soft thumb more.  The more he did, the more he ended up just humping into her grip.  
"It's alright… bet it feels good, doesn't it? Let me have a front row seat." Brittany cooed, her other paw moving up to caress Theodore's plush thigh. She gave it a squeeze for good measure, gently running her claws through his fur.
Theodore whimpered, his eyes shut tight with pleasure surging wildly through him. “Okay, o-okay, you can!” He squeaked out.  With that, Brittany lowered her head and started brushing her tongue against his fuzzy balls, her eyes fixated on his big butt yet again.
She relished in the shaky moans he let out, letting the little guy set his own pace as he continued thrusting into her paw.   She kept it steady, catching any pre that leaked out and smearing it over his shaft as he kept moving.  
“Mmmn, thatta boy Theo… keep it up~!” Brittany encouraged, this time licking up from his balls to his taint.  She felt the muscles there tense for a moment, paired with his breath hitching in his throat as he tensed up.  
“I-It feels weird theeeere…” he moaned out, resting his head on the recliner’s arm.  
“But you like it, right~?” Brittany cooed.  She gave the tip of his shaft a squeeze, then slid her paw down to the base, lightly cupping his balls so she could fondle them both, switching between grooming the left and right with her tongue.  
Theodore’s response was to nod his head and whine, pushing his rump closer to her as he tried lifting his hips higher.  “Y-Yes, yes, I doooo!”
"Hehe… Wonder what'll happen if I do this~" she hummed, licking between those needy nuts before she turned her attention to the base of his tail.  Did she dare…?   Yes.  She hesitated for a moment, but finally made herself do it.  Brittany buried her muzzle between Theodore’s cheeks, immediately beginning to lick all over his asshole’s rim.  That got him to gasp out loud and push his ass right up on her face even more.  Brittany’s groan was muffled, but she found herself unable to stop.  
“Wait, aaah!  Oh, ohhhh… nnnhaahn…~” Theodore’s protests were quick to melt away into more of those precious moans.  
After the first couple swipes, her tongue was inside of him, swirling around in circles.  Right as she was getting used to the taste, though, what happened next surprised the both of them. Theodore, after letting out a weak whine, chomped down on the recliner arm to muffle a loud scream. Seconds later, his hips bucked down, cum starting to shoot out of his tip.  The first couple spurts landed in her paw, but the rest simply splattered messily on the cushion, forming a puddle between his legs. With a blush on her face, Brittany kept her paw moving as he came, stroking his shaft downwards.
“B-Brittanyyyy…!!  Oh gosh, it’s so h-hot!”
She could feel every pulse, every throb, every twitch of his dick as his sticky cum squirted on the couch. And, suddenly, Brittany pushed her nose back to his balls, drawing in a deep sniff and quivering all over.
‘Ooohhhhh that’s goood…’
Theo's eyes rolled back a little as he dropped to his knees, his cheek squished to the cushion as he collapsed, panting heavily as he tried to recover. "Hnn… Brittany, wh… what did you do…"
Brittany, still savoring his scent, blinked a few times. Then she looked down to all the jizz he let out before she looked at him again. "Wow... You really… really haven't been touched before, have you?” She asked. “Shouldn’t be shocked I guess…”
“N-No… I’m sorry…” Theodore said as his ears drooped down.  
Sighing, Brittany sat up and gave him a little pat on the head.  “It’s alright, Theo.  I just meant you probably didn’t have a reason to.  And really, it’s not like that there’s a lot of other chipmunks around here for someone else to do it!”  She paused for a bit.  “But.. I just at least thought you woulda… you know.”  She paused, making a jerking motion with her paw.  “On your own?”
Theodore looked timidly at his feet.  “I mean, it’s gotten hard and all that before…” he admitted.  “But nothing like that!  It got all sticky when I rubbed it on soft things, and it felt nice, but I never shot that stuff out!”
Hearing that put a proud little smirk on Brittany’s face as she started licking her paw clean. His taste was notably salty, of course, but she swallowed it anyway. At least he had a hint of sweetness in there. “So… I got your first load ever, eh?  Not bad~”
Theodore was smiling again, his bushy tail beginning to wag side to side. “I did good?  Does it… taste alright?” He asked eagerly.  
“Ohhhh yeah big guy.   Very good!”  Brittany praised.  And yet… her heat still needed to be sated.  “But we’re not done just yet.  We still got the big finish, after all!”
"Well, if that means I can keep feeling like that, then okay!" Theodore said, his tail swishing a little faster. Already after an eruption like that, his length stood stiff as a board.
Another grin came to Brittany's face. 'Don't worry. You'll feel that a lot more.' she thought. She rolled to her side, grabbing his jacket and rummaging through the front pocket, producing one of the rolled up condoms. “Alright, c’mere.”
Laying on her back, Brittany grabbed Theodore's butt, pulling it closer until their crotches met. A way for him to have his fun while she got to watch his cakes more.
Theodore looked back at her again, wiggling his hips a bit. "Hey, hold still." She said sharply, tugging his tail. He nodded obediently, squeaking, and staying as still as he could manage.
It wasn't exactly hard to get the thing on. Brittany held on to his cock, aiming it down at the protection. She pinched the tip of the condom, placing it on him and rolling it down to the base.  Theodore was doing his best to hold still, but he still moaned from the touches.  
"I-It feels weird." Theodore complained as soon as it was on, trying to peek down between his legs at it.  “And wet and… tingly?”
"Well, that's gonna stop you from making me pregnant." Brittany responded simply, taking hold of his length and lining it up with her slit. If just stroking him off made him blow fast, there's no way he'd survive long in her.  But all she needed was him to drive her over the edge.  
"Okay... Now, there's gonna be a little barrier you'll have to go through, so just make it quick." Brittany says, biting down on her lip. She took in a few deep breaths to prepare herself, trying to relax. "Just… you know, just let me know when you're gonn- GAH, DAMMIT THEODORE!" She screamed, clamping a paw over her mouth. 
Theodore didn't waste time.  As soon as she wasn't holding him back, he simply dropped his hips down until they smacked against hers, breaking through her hymen easily, his own moan nearly drowning out her scream.
'Just get him back later, Brittany.' she thought, breathing heavily through her nose, deciding to focus on his rear instead. Then, she grinned.  ‘Or… now~’.  She gave his butt a hard slap. 
“Hgnnn!” Theodore grit his teeth as he endured the spank, just to stand on his tiptoes as he rutted into Brittany’s squeezing walls. The pleasure made him yelp, then moan, giving a surprisingly rough thrust downwards, his tip brushing along her walls all the way.
He needed no further instruction, instincts seeming to kick in as he started to hump her eagerly, making both of their bodies bounce against the cushion below. Brittany could only watch as he had his way with her deflowered pussy, a lustful haze in her eyes while she eyed his ass and his balls, almost like she was in a bit of a trance.  The growing wet ‘plaps’ of their sex was filling the air, almost always met with a moan from either chipmunk.  
‘Okay… maybe get him back later.’ She thought, her gaze staying intently on Theodore’s rear.  
No words were really needed, their moans being all the signs needed for their obvious bliss. But soon enough, Brittany just couldn't help herself. "Thatta boy, Theo… aahn, y-you like how it feels in me, don't you~?" She cooed, mainly teasing him while spanking his rear every now and then just to get a few extra jiggles from him. 
Theodore winced each time she did, but it really only got him to speed up or get louder. He never seemed to mind. When the stinging pain faded, there were just pleasurable tingles that spread over him.  “I r-really like it…!” He closed his eyes tight, already feeling himself sweating from all the motion. 
Who knew something this fun could be so tiring?
"Y-You're- Aah! You're really good at this!" Brittany managed to gasp out, holding on to Theo's tail for dear life. The little hornball was making her head spin! “Oh fuck, T-Teddy!  Fuck me, don’t stop~!”
She really was here… Theodore kept getting balls deep in her.  For once, her heat was fading without her waiting weeks on end!  It was unreal how good he had her feeling. She’d almost thought Alvin and Simon would be too big-
“Nngh, oh jeez, this is…!”  Theodore’s claws dragged down the recliner arm as he tensed up for a few seconds.  “Oh n-no!  That feeling... It's… it's coming b-back!" 
As much as he wanted his peak, something at the back of his mind was telling him to slow down. So… he did.  
“Hey, hey!  What the heck, Theo?!”
Panting away, Theodore made one more hump before bringing himself to rest.  “Sorry but, aahhhhn… I didn't want it to end!”
“Dude, bad timing!” Brittany whined as she flopped on her back.  “Sheesh!  I was right there…”  She lifted her head with an annoyed huff, flicking her tail side to side.  “This won’t be our only time doing this, alright?  This time, don’t slow down, don’t stop, nothing like that, okay?”
Theodore nodded slowly, raising his hips up once more.  “Do you… want me to keep it up like this?”
“Heh… yeah.  Gotta keep an eye on that big butt so you won’t stop.” Brittany grabbed his tail again, tugging it so she could start rubbing all over his butt again.  “Be a good boy and rail me until you can’t move.”
With another blush coming to his cheeks, Theo did as he was told.  “Ahn, h-here goes!” He warned her.  As soon as he was inside of her again, Theodore bit into the arm once more, all claws gripping the recliner tight as he humped away. 
And Brittany, holding his tail so he’d stay buried deep, took little time to start moaning again.  “B-Better!  Now keep that up!” She instructed.  Honestly she was shocked that he hadn’t gotten too tired yet… 
“Mmf… hnn…!”  Theodore’s claws dug through the cushion and exposed the stuffing inside.  As good as it felt, it was definitely tough keeping up with what she needed.  He tried getting rougher for her, managing to raise his hips higher even with Brittany yanking his tail back down.  
And he still had to wrap his head around her actually liking him this much!  She’d hardly even spoken to him before… it made his heart flutter~
Letting out a soft groan, Theodore suddenly turned himself around, free of Brittany’s hold and, instead, putting his paws on top of her chest.  Before she could even say anything about it, he had her pinned down as best as he could, his head tilted back as he moaned freely.  
“C-Can’t stooop…!” He groaned, claws hooked into her fur.  He couldn’t even feel himself throbbing much anymore.  It was more like he was as hard as can be, with his shaft barely able to twitch even. 
“Mmn, then don’t.” Brittany encouraged as she hugged Theodore’s head to her chest.  He was pretty cute, no doubt… but, despite his words, he was definitely starting to slow down.  Maybe he was close?  Just in case…
“Oh jeez, it’s gonna come out, Britt!  I’m gonna- w-whoa!”
Theodore let out a loud squeak as Brittany suddenly rolled over with him.  Now, she was the one doing all the moving, hips bouncing up and down while she put her hands on his belly again.  “C’mon big guy!  Fill it up!” She ordered, grunting every time her hips slapped down onto his.  
His only response was to try and keep up with her, thrusting his hips up whenever she gave the chance.  His claws had sunk into the seat again, and Theodore closed his eyes tight.  And, it wasn't much later before he was crying out again, giving one last thrust. 
“Hnnghhh, t-that’s it~!” Brittany pushed herself down again, holding Theodore inside of her right as she tensed up, going over the edge first and letting out a loud moan as she climaxed on him, making their crotches a sticky mess while Theodore pumped his seed into the condom within her.
Finally…!  Brittany’s vision went a little hazy as she hit cloud nine, riding out her orgasm and continuing to hump herself on Theo’s spasming shaft, savoring the growing warmth that the filling condom was giving her.  “Yes, yesss, fuck yes, gimme it all dammit~!” She cried out.  She could almost feel tears down her cheeks from how good the release felt.   
Brittany was left panting, her afterglow hitting like a ton of bricks. As much as she wanted to stay there, she ended up falling over on her side, releasing Theodore’s shaft with a wet, audible ‘plop’ as she slumped down in the chair.  She rested her head against the cushion, her body trembling slightly as she scooted herself closer to Theodore, holding his head to her chest once more.  "Gah, jeez Theo... That was amazing for a first time!" She says, looking down at him.
"Well... It just felt a whole lot better than your paw." Theodore replied, paws covering his cheeks. “Are we… gonna stay like this now…?”
“Hmmm…” Brittany tapped her chin a few times.  Then, she grinned at the chubby munk.  “Well, I bet you want a snack right now.  And I just had an idea~”
The thought of any snack was all he needed to hear, nearly bolting up then and there. “I’ll take it!” He insisted as Brittany held herself steady on top of him.  “Whatever you got!  Happily!”
“Easy there boy!  Don’t wanna waste it.” Brittany snorted in amusement, patting Theodore on the head.  Then, carefully, she started to stand up on quaking legs, biting her lip as she had to find her balance.  Soon as she did, she turned her attention to his crotch. 
Sure enough, he had filled up the condom.  Even more than she expected. She grabbed his dick once more, careful as she pulled the condom off, making sure none of his cum could escape.  “Now, Theo… eat that.”
“…The whole thing?!”
“What?  No, silly!  Just, ya know, drink the stuff out of it!”  Brittany huffed.  “I was gonna do it myself, but I figured you’d want something yourself.”
Theodore looked at it skeptically, wrinkled his nose at first, but then he nodded. “Maybe if… we share it?”
“Pfff, you’re weird.” Brittany commented with a little smile.  “Ellie’s gonna have plenty of fun with you.”
Admittedly, she didn’t think this through.  She expected the pudgy munk to want it all for himself… but she’d come this far.  She sighed a little, but held the condom up to her mouth.  Before she could talk herself out of it, she stuck her tongue inside of it and tilted her head back, letting the warm cum cascade down her tongue for a second or two before she hurriedly handed the other half to Theodore.  
The salty, sorta sweet taste lingered even after she gulped it down, watching as Theo did the same.  He, however, visibly winced for a few seconds.  
“Hrk- I… think I’d rather get an actual snack.” He admitted, wiping his lips on his arm.  “Gosh, you liked that?  I wish it was sweeter!”
“Somehow, I’m not shocked.” Brittany rolled her eyes, but moved to help Theodore up to his feet.  “Well, we still have to regroup, don't we?" She asked.  “We’ll get something better after we meet up with the others, I’m sure.”
While Theodore rolled onto his feet, Brittany found herself reaching back for his paw.  
"Hey, uh… sorry about smacking your butt so much. I just… really got into it." She said sheepishly, looking down at Theodore.  “Heat makes me think of a lot of stuff as hot and-“
The pudgy munk just smiled up at her, rubbing his nose on her arm.  Brittany went quiet, but he gave her a light kiss. "Aww, it's okay! I… kinda liked it, once it got all tingly." he admitted, hopping off the chair with her. “Hehe, I’ll definitely remember my time with you though~”