“Okay, so, don’t laugh or anything alright? I just really… wanted to give something like this a shot.” Brittany said as she led Simon outside. “Well, it won’t be my first time doing this kind of thing outside, at least. Eleanor said she wanted to “let herself be loud, just in case.” or something like that.” Simon responded almost absently as he followed Brittany. Admittedly, his mind was both here and elsewhere at the same time. What would she be like? Simon couldn't help but keep an eye on her as she lead the way to her chosen spot; the pool in the yard. Once they were out there, Brittany had gone to retrieve the life preserver, and was now dragging it into the water. Of course, they were still in the nude, so Simon carried his condom in paw. As much as he wouldn’t outwardly admit it, Simon was quickly finding their new situation to be very exciting and interesting. Well, anyway, maybe Brittany was... Excited? She seemed to be. It was hard to tell with that slightly furrowed brow of hers. Clearly something more than just their nearing intimacy was on her mind. Simon moved up to her, clearing his throat and tapping her shoulder. "In the pool, Brittany? I didn't take you as one to let her hair get wet." he commented, trying to break the tension. Contrary to his plan, Brittany didn't react as expected. Instead, she sighed, then turned to look at him. Her tail drooped low, and her paws crossed over her belly, and that brow still furrowed. "Simon..." “Er… bad time for a joke?” His ears laid flat against his head. “Just adding a little levity, is all.” “No, it’s not that it’s just…” She took a step towards him, a paw lightly clasped at her elbow. Simon couldn't help but blush beneath his fur from the closeness, but he stayed in place. "Yes, Brittany? What is it?" Simon’s tail bristled up as Brittany suddenly wrapped her arms around him, resting her head on his chest as she let out a little sigh. Her actions were very... Jeanette like. “Seriously, you’re starting to worry me-“ "Si... You know we're gonna be taking a big step next time we switch... And you're a reeeeeally smart guy.” Brittany nuzzled into his chest a little, then looked up to his face. “I… can’t believe I’m asking this, but… Do you... happen to… Know a little something about Alvin? About how he is in bed, I mean." The silence was suddenly thick, hanging over the two munks as Simon just stared back at Brittany. Did… did he hear her correctly? “You know, like, the sorta stuff that revs his engine? Gets his motor running? C’mon Simon, I’m talking about what’ll turn him on! I know it’s a shock to hear, but Alvin and I haven’t done anything like this before!” Definitely… not the question he expected. “Wha- i- no i just-“ Simon blinked a few times from the shock, but cleared his throat. "Er... Brittany? Why exactly would I know anything like that?" He asked. Brirtany pouted, but then she moved over to Simon’s side. She started to trace a claw through his chest fur, moving it in slow circles. Simon gulped quietly as her other paw trailed along his belly. “Well, he diiid tell you all about his little fantasies and such..." She spoke. "That’s how all of this got started, after all. I just thought you could… probably tell me what I could do for him. Of course, I can make it worth your while~" Her paw moved quickly, now firmly in between his legs, right on his sheath. "Yipe!" Simon's eyes went wide as he clamped a paw over his mouth, his blush getting stronger. "Hmmph... Fine, Brittany." He says, putting his paws on her shoulders. "But… only if you can tell me something about Jeanette and Eleanor. Seeing as they always hid themselves away with you around this time, I'm certain you know your fair share of secrets as well” Brittany pouted again, but she nodded her head anyway. “Mmm… I shoulda known you wouldn't be that easy. But you got yourself a deal." She said, working her paw along his sheath slowly. "Jeez, you're a big boy… Thank goodness. Can’t wait to feel it~” “Is it really- What’s that supposed to mean?” Simon asked. Brittany didn’t answer that one though as she gestured over to the floating life preserver. “Hop in and I'll tell you what you want." Simon tested the water first, shivering a bit as his toe met the cool water before he sunk in slowly. He bit the edge of the condom’s wrapper, paddling his way into the floating ring and propping up against the inner edge. Brittany, however, just jumped on in, landing on all fours across from him, causing the whole thing to nearly flip over. Once they were balanced again, she lowered herself in the water until just her upper half was out. "So... Let's see..." She tapped her claws on the ring. "Ellie definitely has a thing for scents. Especially coming off of you guys. But mostly Theodore, obviously. I heard her mumbling something about stealing one of Theo's jackets last year. Wouldn’t be shocked if she had some stashed in her bed, really. Don’t tell her i’ve been on her bed, but kinda smells like one of you guys over there.” 'Probably would've been helpful a while ago...' Simon thought with a roll of his eyes, taking the mental note. Brittany continued. "And Jean... Hmm. I guess you could just be kinda rough with her. Ya know, tail pulling and such. Y’know what they say about the quiet types. Honestly, I didn’t get much out of her. But I did hear her talking about how she looks when the heat hits.” She shrugged her shoulders. “Maybe she’s got a secret thing for watching herself?” Simon’s eyes narrowed at the thought, skeptical. "You… aren't lying about that, right?" Maybe the part about Eleanor was right. But Jeanette, of all chipmunks, wanting it rough? Admittedly he had his doubts, but… he also doubted they’d go this far in the first place. "Hey! What do I get from lying?” Brittany huffed, crossing her arms over her chest. “I dunno what you think we got up to, Simon, but it’s not like we were chatty about our turn ons.” Brittany kicked water at him playfully. “You got your answers! Now you spill those beans." Simon gave a sly smile, returning a splash of his own. "Alright, alright… His feet are sensitive and he likes having them massaged. And his… butt. According to him, he… fingers himself regularly." He replied, huffing as he looked away. Listening to Alvin spill everything on his mind earlier was… an experience. Sighing, he then turned his full attention back onto her. "Now then… how about you spill the beans about yourself?" Brittany gulped, watching him closely as he swam closer to her. In no time, Simon was on the same side of the floaty as her. He moved a paw down to her butt, and when she squeaked his other went between her legs. “S-Sheesh, you already have a good start!” She squirmed in his hold, unable to stop herself from moaning as she tilted her head back. His fingers had hardly started brushing over her pussy, yet she already felt light as a feather. “Nnngh… d-don't make me wait…" Simon had started to kiss her chest, and now he was moving up towards her neck. "Easy, Brittany… just let me work…" He set the condom aside on the ring, his full attention now on her. As Simon’s digits explored further, Brittany dug her claws into the floaty with a stifled moan, tilting her head back while Simon’s lips traced around her jaw with more kisses. “Jeez, someone knows his way around a- hnngh!” Brittany was interrupted by a gasp, letting go of the ring long enough to cover her mouth with a paw. She could feel them both; two digits digging in together before separating to come back out, just for him to push them in again and repeat the process. He started out slow, but as soon as Brittany was moaning out loud he picked up the speed, the water making light splashes in tune with his paw’s movements. “Heh… well, it looks like Theodore was more than enough to get you spread out.” Simon pointed out, mainly to tease the Chipette. “Gnnh… g-give the guy credit, he’s very eager when he gets going…” Brittany let out a grunt as she rolled over, resting her chin on the floaty. He’d barely started… why was she so out of breath? Then, he added a third finger, Brittany gasped, her eyes going wide as she ended up biting deep in the floaty. It wasn’t enough to quiet her, but she still tried to squeeze her legs together. Regardless, Simon kept working those digits in and out of her, stroking along her inner walls whenever they squeezed down around him. “Not too bad, huh?” Simon taunted. Brittany groaned and looked back at him, raising her tail up high and swishing it side to side. “Okay, okay! Maybe we don’t need the foreplay part.” She didn’t want to admit it, but he had her on edge already. “What makes you say that?” Simon asked, though he still didn’t stop. The more she squirmed around, the more he worked his fingers deeper in her tunnel. She was lifted out of the water enough for him to see her whole body, and he’d be a liar to say he didn’t stare at the chipette longer than he’d admit to. She looked fantastic even with her fur slicked down from the water~ Brittany had a definite natural beauty to her as is, but his own growing arousal dictated that he takes in the sights. With her tail up the way it was, both of her entrances were put on display. Part of him wanted to pin her… Simon gulped and drew his fingers back, giving her a moment to calm down. He glanced away for a second, just to find himself looking back just as fast. With all her wet, dripping fur laying flat against her body, it showed off more of the feminine curves she had. Though Simon definitely focused on her holes. Her anus, puckered and untouched, twitched slightly as Brittany bent over the ring, grabbing her tail and holding it aside. Below, her pussy beckoned more. That alluring scent demanded him to jump out the water and have his way with her. “Hey!” Brittany’s voice snapped him out of it, making Simon shake his head before looking up. “Stare any more and you’re gonna cum in the water! Now wrap up and gimme what you got while you’re still hard.” She picked up the condom and lightly tossed it to him, lowering herself off the floaty until her legs were submerged again, while keeping both her holes above surface. Simon caught it, feeling his face heat up at her words. “Hrrm, well, as you wish.” Simon said while unwrapping it, paws going underwater to roll it on. He moved behind her once it was on, resting his paws next to Brittany’s as he brought himself closer to her. “Scoot back a little?” Brittany just nodded and moved her hips back to him, claws digging into the floaty as she did. ‘Okay, okay, you know he’s big. A lot bigger than Theodore. Deep breath, and-‘ “Fuuuu-uuck!!” Brittany interrupted her own thoughts as Simon lined up with her pussy and took the plunge. He only got in halfway, but he was already deeper than Theodore reached. It felt amazing, but he was also stretching parts that even his fingers couldn’t reach earlier. “S-Sorry, you said-“ “I know w-what I said! Nngh, just keep moving before I go crazy!” Brittany cried out, doing her best to not tense up as she slowly adjusted to his size. It did help when Simon started humping her, though, huffing hard through her nose while she lowered her tail, wrapping it around Simon’s waist. “Nngh.. speed up?” Simon asked as he put a paw on Brittany’s butt. Trying to stay afloat like this was tough… but he had to tough through it. He grit his teeth, eyes closed tight as he tried to pick up the pace for her. “W-Wait, I didn’t- Aaaghh~!!” Brittany gripped the floaty tighter, her ears laying flat against her head as she took the pounding. Her tail tightened on him, and sne nearly lost her holding. She’d give Theo full credit for doing his best, but… “You’re almost a-at the base, just a little more~” Simon groaned into her ear. It was encouraging, even more so when his paw moved from her butt to her chest. “Aah… you’re actually taking it m-more than Eleanor could~” He had to get both his paws on the ring soon after, though, bringing his body even closer to Brittany’s as they both clung to the side. Just a little further… Simon rested his head on Brittany’s shoulder, panting away while he pushed through the water, letting out a low groan as he nearly hilted in Brittany. Encouragement aside, Brittany was left trembling all over. The cool water on top of her heat steadily being railed out of her… it left her winded, laying her head on the floaty. She could feel her peak getting closer and closer, but something was keeping her on edge. Brittany sunk her front teeth into the life preserver, panting heavily through her nose as Simon continued to rut her from behind. Even in the water, somehow he was pounding her harder than Theo had. And damn was her head in a spin from it. Every time he pushed forward, all of that dick reached deeper than she thought she could take. She barely had the time to say anything about it! Not to mention all the splashing water would cover her voice. "S-Saaahmuhn..." She moaned out, slurring his name as she wiggled her hips weakly. Simon's paws were right next to her own, so she grabbed on to them for support. She felt his paws flex, his claws digging into the ring. “Yesss, Brittany?” He huffed through his own stifled moans. She’d have replied if he hadn’t nearly hilted then, his hips lightly pressed against her ass. The sensation of fullness had her arching her back and trying to push into Simon more. “Haah… you haven’t told me what you like yet…” Simon panted before he sped up a little more, now just barely putting out from her before he thrusts in again. He lowered his head, gently nipping a path from the crook of Brittany’s neck up to the base of her ear. “Come now, Brittany. Too stubborn to tell your own secrets~?" Simon whispered, his heavy breathing against her inner ear making her tremble yet again. "I... Oh, gosh, just s-slow down a bit and I can t-talk!" Brittany finally squeaked out, tightening her hold on his paws as Simon just continued to ravage her. She moaned out loud, her feet kicking uselessly in the water. Her eyes shut tight, she lifted her hips a little, trying to get him in deeper, if possible. "I like... A-Aah... I like to..." Simon grinned, pausing to wriggle his hips with her’s a little, making his shaft bump against the soft sides of her walls, specifically trying to get the ribs of the condom to grind up within her tunnel. "Yes, Brittany~?" He couldn't help but be amused by her. "Slow down... I like it... gentle… gentle too…" She mumbled out, drooling on the life preserver, a heavy blush settling beneath her fur. "Rough sex is hot and all, but… Jeez, man, you’re huge! And going gentler makes it last longer." At her words, Simon blushed at first, but started to calm himself, looking down into Brittany's soaked auburn fur. “Both you and Eleanor have said that about my size… is it really that big?” “For our size? Yes! It’s good, but you got me all tingly right now.” Simon raised his head to glance around. They had floated towards the middle of the pool from his rough thrusting alone. "That, uh, sounds like you've done so before…" Brittany’s response was a huff. “Let’s just say some things aren’t good toys.” While the two caught their breath, Simon leaned away so Brittany could roll over, now looking her in the eyes. “Ready to try again?” He asked after a minute. Brittany sighed softly, looking off to the side first before puckering her lips, waiting. Simon planted a kiss on her lips, wrapping an arm around her as he pushed back inside of her pussy, waiting until he had gotten in most of it again. Then he started giving heavy, slower thrusts into her. He couldn't help but shudder. At this pace, it was much easier to feel her inner walls as they gripped his covered length. Thank goodness he made the condoms somewhat thin; being able to feel her clench up or spasm made it all the better. "N-No… but videos are… y-you know..." Brittany mumbled. She pulled back from the kiss, panting weakly as she rested her head against the ring's inside. "This is, ahh! B-Better... gosh this is so much different than Theodore." She groaned, gently scratching behind one of Simon's ears as she hooked her legs around his hips. Simon grinned a little at the compliment. He knew Theo had the smallest length… or at least assumed so. “Oh come now, I’m sure Theo what he could. He got you to your climax after all, didn’t he?” “Hmph! You were supposed to say “Thank you, Brittany, that’s an awesome compliment”, not make me blush even more!” "Ehehe… Why thank you, Brittany." He says, giving her a light kiss on the nose, wriggling his hips a little more. The friction felt rather amazing~ "I feel like I could cum just from this, to be honest." After such a wild start, it wasn't much surprise that the slower, more focused thrusting was getting him all riled up again. Brittany wrinkled her nose a bit. She wasn't exactly close, at least not as much as before. "Well... Let's hold off on that for a while, hmm?" She planted a sweet kiss on his chest, rubbing her nose into his soft, dark fur as she moved her hips as well, guiding him towards her tender area, proceeding to hump herself against his shaft and letting out an ecstatic moan. "R-Right there, just… mhhn, grind me there, pleeease… that's the spot~” Simon nodded and soon matched her pace, resting his forehead on hers as their gazes met once more, light and dark blue eyes locked together, focused on each other's impending peaks. Brittany's claws gently dug into his back, her body pressed firmly against his as her eyes shut tight. “Mnnh, so, this is better for you…? I’ll have to remember for next time.” “Awwwh. Already thinking of our next go together~? Aa-aaahn… let’s finish this one first~” “Heh. You’re right, we should.” With that, Simon grabbed Brittany’s butt again, his other paw gripping the ring even tighter as he pulled out of her enough to turn her around. “Uh, si? What are you- o-ooohhhkay… keep doing that~!” Simon had Brittany pinned on their floating ring now, keeping her chest pressed against it. He sped up just a little, but still focused on hitting that little spot as much as he could for her. She couldn’t help biting the floaty against, teeth pressing deep into plastic as she held on tight. “Oh g-gosh Simon…!” She closed her eyes, breathing heavily in anticipation. There it was… and it was creeping closer~ “Hnngh… a-ah, aah…” Simon also started to tense up as his own peak drew near. He grit his teeth snd pressed forward. With the rest of his energy, Simon made his last few thrusts back at his earlier rapid pace as he moaned out loud. "Brittany, I'm-!" His head tossed back as he began to fill up that condom, toes curling in the water as his load made it swell up inside of Brittany. And Brittany, reacting to the warmth growing against her sweet spot, followed suit, hiding her face in Simon's chest to muffle herself as she hit her climax after him, her walls giving one last squeeze around his shaft as her own juices began to gush out into the water around them. Their panting, satisfied, bodies soon came to an abrupt halt. Their floating ring bumped against the opposite edge of the pool. Simon, smiling at their little voyage, gave Brittany a kiss on the lips. His mind was racing, and maybe the afterglow had some influence in him. But, a thought came to him and he smiled a little at Brittany. "Thank you for riding the S. S. Simon. Feel free to come back any time~" He joked, unable to stop himself from snorting as he rubbed noses with Brittany, who laughed softly and tried pushing him away. "Simon, that's almost as bad as Alvin's little "Get Munked" thing."she says, letting him help her out of the pool. While she shook herself dry, Simon discarded the condom, simply tossing it aside on the ground. He held out a paw to her. "Chances are the others aren't done yet. How about we just talk?" He offers. Brittany smiled, taking his paw. "I thought you'd never ask." "So… videos you've seen, huh? What about?" Simon asked. Brittany was immediately blushing, pushing at his chest. "H-Hey! A girl can only watch so many nature documentaries! Do you have any idea how few chipmunk specific ones there are?" She crossed her arms with a huff. “Maybe next time i’ll set up a cam or something so we can have more!” Chuckling, Simon shook his head. "Well, no, I suppose there isn't much. But why make it when you won't need it for a while? And, all things considered, there’s always a risk of it getting out and- "Simon, you’re starting to spiral. How about we just spoon before you psych yourself out~?” “Oh… heh, right.” Simon made himself go quiet, instead hugging Brittany from behind… before he lifted her off the ground, making the chipette squeal out loud. “H-Hey! I thought we were gonna spoon!” “We are~! Just not out here!” Simon responded with a laugh, carrying Brittany back towards the house. Even as she squirmed around, he just held her tight until they were inside.