"Sooooo~? How is it? Do you like it? What do you think?" Eleanor asked, one question immediately after the other. The pudgy Chipette was down on all fours in front of Simon, stripped down to her bare fur. Her tail was lifted up nice and high, swishing side to side as she shamelessly showed off both of her holes to him. Mainly, her puffy slit, freely dripping her sweetly fragrant juices onto the grass below. A gleeful grin could be found on her face, along with an aroused blush, no less!  
“I’m gonna say that lil’ pink poking up is a sign you love what you see~” Eleanor teased, reaching her paws back and spreading her butt more.  “I don't mind ya staring, but you’ll show off a little for me too, right?”
The two of them had gone outside to the backyard, lost among the tall grass, their only light being the moon above and the porch light behind them. As soon as Simon made it clear that he meant well, Eleanor relaxed enough to undress. And that she did. Simon found himself tugging at his jacket's collar all while he watched her strip.
“I know i’ve been yapping your ear off since we got out here, but… If this is gonna work out, we better get the weird part out of the way fast.” She had insisted. “I just want it allll out so I don’t say something too silly later.  And, full honesty, I’ve never been able to last super long, so you’ll probably be quick with me.”
“Come now, Eleanor, there’s no need to rush anything.” He had told her.  
Simon shook his head now with an amused smile on his face. He sat down on a few blades of grass, watching Eleanor's little display. 'Even when she's all heated... She's silly.' he thought. 'Just how much of this is her heat talking, anyway?'
No matter how strange it seemed, he couldn't fight the fact that this new… openness was natural. Besides, how often would this opportunity come up afterwards?  They were better off accepting it as is.  
"We’ll just go until you feel better.  And, by the way, you look amazing, Eleanor." he hummed, scooting himself closer to her, gently putting a hesitant paw on her rump. "Absolutely stunning even, if I do say so myself..."
Her response was a soft little chirp, pushing her butt closer to his touch. "Awww, thank you~!  Since when were you such a flatterer?” Eleanor teased, poking her tongue out at Simon.  “Soooo… if you’re not gonna lose the jacket now, do you mind touching a girl down there, at least?" She asked, shaking her hips lightly, causing her butt to grind against his palm. "It'd be a pretty big help.  Doesn't matter which hole you pick, either~”
"Heh... Alright then, Eleanor. How about this?" Simon moved his paw from her butt, running his finger against her dripping pussy, gathering up the juice that leaked out while he moved his finger around in slow circles, gaining a sudden happy moan from Eleanor. 
She shook her rump eagerly, scooting herself back again until her butt was squished against his crotch. "Gah... C'mon, Si... You can be a little rougher, ya know~" She says, panting lightly as she looked back at him, her tail bristling slightly. "I know I'm small, but I won't break. Trust me."
Simon nodded, adding another finger into her while he grabbed her tail with his other paw, tugging it upwards while his fingers stirred within her slit resulting in another blissful moan from her. "It's… This is very odd. I never imagined we'd actually be doing this, you know." He spoke, squeezing the base of her tail.
Eleanor only moaned again, her ears flat against her head as she dug her claws into the ground, tearing the grass a little while she fought the urge to squirm again. Her own paw was one thing, but someone else's was all the more exciting! "Yeah, m-me neitherrrrr…” Pulling at the grass again, Eleanor raised up her hips as high as she could while staying on all fours.  “I’m soooo… G-Glad we are, though!" She managed to say, closing her eyes tightly. "Gosh, Simon, you're good at this!"
Her tail started to wrap firmly around his wrist, holding it in place. They had barely started, and she already felt like she was losing her mind!
'If this is what you want...' Simon thought, pushing his fingers further into her, making her squeal yet again. 'Then I'll do my best!' And then, Simon pulled his paw away from her.  
Eleanor pouted and rolled over on her back.  “Heyyyy…”
“Well, you wanted me to undress, right?” Simon responded, taking his glasses off for now as he lifted his jacket off, taking his sweet time as it passed up his belly. 
“Ooooh boy~” Eleanor cooed.  She knew his jacket didn't hide away anything important, but getting him to join her nudity was a comforting plus.  “I definitely see what Jeanette likes!”
To that, Simon let out a quick, quiet scoff as he rolled his eyes.  “Really now?” he asked, pausing as his chest was revealed.  
“Oh yeah, for sure~” Eleanor’s tail wagged as she took a step forward.  Her nose buried into the fur on Simon’s chest, taking in a few sniffs as she wrapped her arms around his hips.  “Don’t let me stop you, though!”
Simon continued until the garment was off completely, set aside in the grass.  Eleanor kept her face close to his chest, letting out a soft giggle as their eyes met. “You smell soooooo good~”
He went to put his glasses back on, but soon found his paws held down as Eleanor took them from him.  Through his blurry gaze, he was hardly able to make out Eleanor’s shape.  But she leaned in and kissed him on the nose.  “I always thought you were kinda cute, glasses or not…” she snorted softly, looking away for a moment.  “Jeanette used to get soooo mad when I talked about you!  She really likes you, too, ya know.”
Simon gulped, glancing off to the side.  “Now Eleanor, no need to get me any more flustered than I already am.” He huffed.  Eleanor responded by kissing his chest, moving her paws down to his hips.  
“Fine, fine… but I think we should get a little more familiar with one another now.” She insisted, her paws reached around fully to grab Simon’s butt.  As soon as she squeezed, he let out a loud yelp that echoed in the quiet night.  
“E-Eleanor!”
She just winked at him, looking up while she continued to grope and caress Simon’s ass, squishing his cheeks together idly.  “Lotta time to watch you work this thing when we were super fans~”
Simon huffed.  “S-Says a lot when you mail yourself to a different country to meet someone…” he grumbled, then went to copy Eleanor.  He took hold of her butt and gave a good, deliberate squeeze.  Unlike his own, though, Eleanor was far bigger and much more squishy to the touch, and she ended up letting out a loud moan while his paws kneaded in.  
“Gooosh… such a tease~” Eleanor said, her voice quickly becoming as shaky as her knees.  His touch was incredible~. It was definitely thanks to her being all horny and bothered, but those paws of his felt like heaven when she was being fondled.  So, she pushed her ass back towards Simon’s paws, purposely keeping herself as close as she could.  “L-Little higher, please~”
“You like that, huh…?  I think I can give you what you want.” Simon said.  “But you’ll have to do something for me, too, alright?”
Eleanor tapped her chin a few times in thought.  “I wanna see what you’re planning, so… sure~!  What do I gotta do?”
‘Okay Simon, no backing out now.’ Simon cleared his throat, gently patting Eleanor’s butt a few more times.  “Down on all fours, please.  And part your legs a little.”
And without hesitation, Eleanor did just that, crouching down once more as her tail curled up again, putting herself on display for Simon.  “I’m starting to think you like us bent ove- Oooohh m-man!” Eleanor was interrupted by Simon mounting her from behind, one paw on her ass while the other grabbed one of her pigtails. But, instead of him just cramming himself inside her raw, he was grinding in between her thighs.  
At first it was weird, but the head of his rod had started grinding on her needy folds, drawing out loud, pleasant squeals of pleasure from Eleanor all the while.  “Hooohkay, oh gosh, that's nice… v-very nice~”
Simon tugged on her hair a few times, letting out a low growl by her ear while his other paw gripped into her soft ass again.  “Squeeze your legs together for me, Ellie.” He groaned.  
“Nngahhn, I s-see what you want~” she replied, giving her hips a shake against his crotch before she had her thighs clamped around Simon’s growing cock, using her tail to wrap up his hips and hold him close.  “Just don't lose your head~” 
With a soft huff, Simon’s paw left Eleanor’s head, instead moving to her chest.  He rummaged a little, but very soon found one of Eleanor's teats, pinching the little nub before rubbing it in tune with his thrusts.  The pleasure was undeniable; for both himself and Eleanor.  The moans she let out easily dwarfed his own!  And even when he tried to hold her still, Eleanor managed to squirm and wiggle as she pleased, which often caused her to grind back to Simon.  
“Jeez, y-you’re big, Si~!” Eleanor groaned, tilting her head back to Simon’s chest.  Even squished between her thick thighs, the head of Simon’s dick managed to poke through every now and then.  “What, you gonna split me open or something?”
“Hrrnf, I h-hope you're aware you wouldn’t have ever said something like that before tonight.” Simon mumbled.  And yet, he ended up having to stifle another loud moan after that. Eleanor had moved her paw down to grab his cock, making him stay in place.  
A few strands of pre spurted out of him, landing either in the grass or in Eleanor’s soft paw. “Wouldn't have to if Alvin hadn't opened the floodgates… but now everyone's getting to know each other a lot better, so I don't wanna hide anything~” Eleanor cooed at him, continuing to stroke along his sensitive head.  “Now, how about you keep playing up here for me?”
Simon would have protested, but a few well timed squeezes of Eleanor’s thighs had him nodding nonstop.  She was doing something for him, he may as well do the same.  As much as climax threatened to come soon, Simon powered through it.  
Both of his paws were at Eleanor’s chest now, each having a nipple to mess about with and tease.  If she wasn't wet before… Simon was suddenly glad they were outside.  Anything inside would certainly be stained now by both of their fluids!  Maybe her heated scent was getting to him more than he’d admit… but Simon quickly found the chubby Chipette taking up his thoughts.  
Things he thought he’d only do with Jeanette… now was all Eleanor.  Simon had to crouch down in order to rest his head atop hers, but he made himself pick up speed.  More and more his cock pushed through Eleanor’s thighs, feeling her pussy rubbing over the top of it each time.  Something deep in his core just wanted to be in her then and there, not even bothering with the condom.  
“S-Simon, ooohhkay, e-ease up or I’m gonna… g-gonnaaa-” Eleanor’s desperate moan brought him back to the moment.  Her warning was late, though, as she suddenly doubled over, holding his paws firmly to her chest as she let out quite the whining moan.  
Seconds later, the warmth and wetness on his cock increased greatly, with Eleanor rocking her hips against him nonstop as she came.  She squirted on him a few times, but didn't let him go at all, barely managing to whimper out his name through her sudden orgasm.  
“Ah!  Eleanor, I’m sorry, I didn't mean to!” Simon stated with a grunt, now having to hold Eleanor up as her legs buckled under her, leaving the Chipette to slump limply against him.  However, she was all smiles regardless, breathing heavy and ragged.  Her tail began to wag as she peeked up at him after a minute. 
“Don’t be… t-that was so… hooo… so good~” Eleanor moaned, leaning back until her head rested on Simon’s shoulder. “Guess that means your turn next, huh?”
“Well, uh, actually…” Simon trailed off, looking down to Eleanor's face.  Even without his glasses on, he could see the satisfaction that filled her expression. She reached a trembling paw to cup his cheek, rubbing it softly.  “Know what?  Yeah, it is my turn.” He said firmly.  
To that, Eleanor let out a relieved sigh. “Oh thank goodness, there's n-no way this heat was gonna leave me alone without something going in~”. She paused, curling her tail around Simon’s body again.  “That… and it wouldn't be fair if I was the only one to cum.”
“Heh… guess that would kinda suck.” Simon admitted as he looked up to the sky.  It was so awkward saying this sort of stuff out loud…
After a minute or two passed, the two chipmunks separated.  Simon got his glasses back on and Eleanor laid herself out in the grass, her turn now to face the starry sky above as she waited slightly patiently.  Fetching the condom from his jacket, Simon wasted no time in getting the protection on.  
To think he was this hard for Eleanor… he watched his shaft go from pink to blue as the condom rolled on fully, giving a few needy throbs once it was properly contained. He’d had plenty of time over the years to prepare something like this… and yet the lube that coated the inside still got him to be more sensitive than before.  He’d curse his own design some other time, though. 
Eleanor watched him with intrigue, her toes idly curling as she held her legs up as best as she could.  “Jeez, Simon, I thought I was kidding about you splitting me!  But you’re just as big as you feel~”
“A good thing, I would hope.  Are, uh… you ready?” Simon asked, internally kicking himself.  ‘Obviously!  Come on, don’t lose your cool now!’
Eleanor just nodded, beckoning him closer with her tail before rolling over onto her belly. She propped herself on her arms, then lifted up her butt as much as she could manage.  As Simon approached, she couldn't help but feel her heart flutter.  She’d fantasized about Theodore so much, but here was Simon climbing on top of her! “While you’re up there, feel free to be grabby~” 
She just hoped her chubby boy was having fun too…
“Alright… here goes!” Simon gripped Eleanor by her waist, his feet perching atop her wide butt as he crouched over her, his hips bucking down until his tip finally poked the outer lips of her pussy.  And before he could wimp out, Simon just took the plunge then and there, not stopping until his hips smacked against Eleanor’s ass and made it jiggle.  
"Aaahh~! Simon, ohh f-fuck!" Eleanor squealed before being muffled by Simon's paw.  The taller munk quickly started railing her. 
Breaking through her barrier didn't hurt as much, hell, she hardly noticed him stop for that quick moment if he did.  Having her heat being banged out of her by the second felt a lot better than she had hoped, drowning out any pain she may have felt.
Simon grunted, gritting his teeth firmly as he took hold of Eleanor's tail, pulling on it a little too keep her butt lifted. He made sure each thrust went in as deep as possible, hitting at her tender walls.  “You… hnnngh… f-feel amazing…!”
'Tight... Should be expected, I guess.' Simon thought, moving his paw from her tail as he sat up some, grabbing her ass and squeezing her cheeks together every time he rutted back inside. Eleanor just got louder with the attention, her paws going up to her chest as she played with her teats, giving them a good pinch and tug. 
"Come now, Ellie... We don't wanna wake up the whole neighborhood, do we?" Simon asked playfully, lowering his head against her neck.
"Nnngh!  I don't care!" Eleanor responded, bucking her hips back in order to move Simon's length around within her. "I-It feels good… I feel good and I love it~!" Drool trickled from her mouth and down her chin, her body jiggling from the force of Simon's thrusting, toes curled tight against the grass as she tried to squeeze her walls around him as best as she could.  
Designing the condoms to maximize pleasure, he claimed... Definitely an A+ idea. It felt amazing! That ribbed texture in the middle… Ellie definitely loved it.  That just kept grinding along her walls no matter how deep or hard Simon went.  Of course she couldn't help but be loud!  
“Ghhhn… Eleanor, you’re milking it…” Simon groaned.  The only reply he got, though, was more of Eleanor’s needy moans.  He had to cover up her mouth again to muffle what would have been yet another loud one. Simon gave her a soft bite on the neck, pushing two fingers into her mouth as a distraction. 
Eleanor immediately went to licking and nibbling around his claws, now breathing heavily through her nose.  'I haven't felt this good before! I need more... more~!' the thought ran through her head non stop as she bounced her rear against Simon's crotch, putting a paw to his to keep it in place, drooling on his claws while her walls clenched around him once more. Her ears flattened as she relished his moans. 
Never did she imagine such sounds coming from him, and yet here they were. Going at each other like rabbits, and she was trying to make enough noise for everyone in the neighborhood to know exactly what they were doing.
"E-Eleanor...!" Simon grunted, suddenly biting down on the edge of her ear. All of her squeezing was driving him closer to the edge. Sure, the condom would hold fast, but she was clenching enough to nearly pull the thing off of him! Simon's paw returned to her tail, giving it a good yank before he pressed his thumb firmly on her tailhole. 
“Hrmh!  H-Hey!” Eleanor squeaked, her blush suddenly getting stronger from the sensation, her whole body tensing up before she collapsed in the grass, paws clamped firmly over both Simon's paw and her mouth as she moaned loudly into them.
“Too much~?” Simon asked with a cheeky grin.  “Let's see how much more you can-”
Before he could finish, Simon could feel the harsh splashes of hot juices against his shaft again, knowing exactly what it meant. He started to kiss up and down Eleanor's neck, trying to make her second climax as great as possible.
Thrusting on her walls, kissing her neck, and even pushing his thumb inside her ass, whatever it took to fully sate her heat's demands.
After a full minute or two, Eleanor's moaning was reduced to a weak little squeaking, her body twitching slightly as she slowly came down from her orgasmic high. “Nggh… s-sorry, but, s-stop…” Eleanor panted, gripping tightly at the grass. 
Simon pulled out of her, quickly tugging the condom from his shaft and squeezing its base tightly. The whole ordeal had him as hard as he could possibly be, but any more stimulation down there would probably make Eleanor faint.
"Fine!  O-Open your mouth!" He ordered, toes curling into the grass as he began stroking himself off in front of Eleanor, tilting his head back as he moans out loud, precum leaking heavily from his tip. Eleanor, after catching her breath, nodded obediently, her mouth hanging open with her tongue rolled out cutely, waiting eagerly for him to reach his peak.  
She licked along the underside a few times, gathering his pre on her tongue before she closed her mouth around his tip and began suckling.  
Luckily, she didn't have to wait much longer for Simon.  
After a few seconds of treatment, Simon had lurched forward a bit, pushing in more of his length into Eleanor's mouth, a loud moan escaping his lips as he started to unload himself right inside her mouth, his balls noticeably moving closer to his body as he fed the exhausted Chipette his cum.  He even grabbed her hair and pulled until her face was buried against his crotch, making sure not a single drop was wasted.
Eleanor's first reaction was to push him away. What a weird taste! Bitter, salty, and sweet all at the same time. She nearly gagged, but... the taste quickly grew on her. After his first few spurts, the bitterness had faded away, leaving behind a better taste on her tongue, which she savored a few more seconds before she happily gulped it down.
"Gah... W-Wow... That was wild..." Simon panted as he shivered. His tip was getting rather sensitive, so he moved back from Eleanor's mouth, collapsing in the grass at her side.
"Join the club, we've got jackets." Eleanor responded, laughing softly as she wiggled closer to him, their noses squished together softly in their intense afterglows. “Uh, sorry you couldn't… ya know, finish inside or anything.  If it means anything, you taste great!”
No need to rush... Their paws met, fingers lacing delicately with each other's, locking them firmly. They were lost to the outside world, only thinking to keep a watchful eye on their new partner.
Though Eleanor soon broke the growing silence.  The heavy Chipette squirmed a bit, looking to Simon’s face.  “So, uh… I know we just finished and all but… think you could keep messing with my butt while we wait?  Please?" She asked softly, smiling sheepishly up at Simon. Before he had said anything, she was bringing his paws down to her rear, her tail wagging eagerly when he took over.
‘This is gonna be the best night ever~’ Eleanor thought, biting her lip to suppress a moan as Simon’s paws hefted up her cheeks.  “Y-You like the weight, right?” She asked with a wagging tail.  
“Heh… you’re perfect as you are, Eleanor.” Simon told her mid-massage, resting his head atop hers.  “Though judging by how fast your scent came back… Do you need one more for the road?”
Eleanor whined a little. “Ehehe… Can’t hide anything from you, huh?” She asked while pressing her face against his chest.  But Simon didn't chide her, instead choosing to kiss the top of her head.  “Just tell me what you’d like.  I’m sure it won’t take too long.” He insisted.  
Eleanor was quiet for a minute.  “Uh… your t-tongue…” she mumbled, just barely able to be heard.  “Not for a long time!  Just, ya know, I-I just wanna know what it feels like!  You don't gotta if you don't want to!”
Simon bit his lip.  “I'm… well, that’s quite the ask, Eleanor.” He stated, glancing off to the side.  “But, I suppose it could help you so… find yourself somewhere comfortable and I’ll give it a shot.”
“Gosh, Simon, you’re so giving!” Eleanor whined softly, but she was quick to take his offer.  
He didn't expect her to climb on him and sit down on his face, though!  Simon hardly had the time to catch his breath before Eleanor had settled herself down, keeping her butt close to his mouth as she laid back.  
Groaning around his sudden mouthful, Simon’s paws went up to Eleanor's crotch.  She was still hot to the touch, even after spraying twice… he steeled his nerves, stuck out his tongue, and began to lick around.  
Immediately, Eleanor squeaked out loud, her eyes going wide as her tail stiffened.  “O-Oh!  Okay, wow!  That’s weird!  R-Really, really, goodly weird!” She exclaimed as her tail wrapped around Simon’s head, holding the taller munk against her ass as his tongue swiped over her asshole. 
She found herself grasping at the grass once more, unable to stop herself from arching up and squirming.  Regardless of how she moved, Simon didn't relent.  His first few licks were hesitant, but now each one was purposely drawn out. Simon hefted her up a little so he could breathe, arms struggling some to support her weight. “You… definitely taste better… than expected…” he huffed out.  
Eleanor huffed at that, rolling over a little.  “Well you’re not the only one who keeps clean…” she paused, her nose twitching about as she was led by it towards Simon’s crotch.  “Gosh… anybody ever tell you how good these smell?” She asked.  
Simon didn't know what she was talking about until he felt her nose pressing against his balls, taking in deep sniffs while breathing warmly from her mouth.  
He tensed up for a moment, stifling his moans and grabbing Eleanor’s waist.  “Feel free to indulge…” he told her, stroking along her hips before he started to lick at her asshole again, holding her tail off to the side as he sunk his whole tongue in.  

Shivering from head to toe, Eleanor opened up wide, eager to fit Simon’s balls in her mouth.  His dick was going soft, but she still got to rub her cheek against it while Simon ate her out.   Another peak was coming already, and she found herself whimpering and shaking herself against his face.  
And Simon took the hint fast, bringing both paws around to Eleanor's crotch.  One buried his fingers in her pussy again, but the other was gently stroking close to the top, finding her little bud after a minute or two.  
As soon as her clit was being played with, Eleanor let out a muffled squeal into Simon’s crotch.  Her hips bucked forward several times before she finally came again, toes and paws spread before curling up once more in raw bliss.  And Simon was down below, catching her spray right on his chest while her tail curled down and wrapped behind his head.  
He gave her a few minutes to recover, savoring the sounds of her quiet, idle little moans as she twitched above him.  Slowly, he drew his tongue back out of her, gently petting her butt.  “Well, Ellie… you were amazing~!  Once you get your footing again, we'll head back to the others.”

“Mmf… y-yesh pwease…” Eleanor groaned out.  If this was gonna be their lives now, she was more than eager to see what the others had to offer.