Alvin paced around the bed a little. Jeanette... He couldn't push himself onto her. No, definitely not her. She'd never forgive him, Simon would castrate him, and Brittany would kill him if he did anything wrong. She continued to look at the door, letting out a sigh.
'I gotta do something, at least…' Alvin thought.
He approached her slowly, taking steady steps to not startle her. He crouched down, rested his paws on her shoulders, his lips puckered up to kiss her neck when she stopped him with a raised paw.  
"I… know what's on your mind, Alvin." She said sharply, still not turning to face him. "You're a guy, and I'm in heat. So… we may as well hurry and do it." She bit her lip, her tail curled across her front so she could hold it. "I'm thinking the same thing too…"
"Aw, jeez, Jean..." Alvin kissed her neck softly, moving his hands down to hold on to her sides. He had started to remove her shirt, but the way she tensed up was a clear sign. Even in heat, she wasn't all too excited just yet. So, he sighed, paws going back up to gently rub her shoulders. 
"Jeanette... If this is gonna work between us all, then we better make sure it's done right.  Right?" He whispered in her ear, continuing to massage her shoulders.
Jeanette's breath caught in her throat, a shiver running from the top of her head to the tip of her tail. It felt so nice… why did she have to feel guilty too?  “Y-You... Alvin, you're my first, but I wanted Simon to be the one who takes my..." She paused and looked back at him, her gaze distant behind her glasses. Alvin definitely saw a tear in her eye.  
"If... If it really has to be you... Promise me you won't change after this, at least. After my heat, I mean. Tell me... That you'd still love me somewhat even when I'm not all horny and desperate."
Her voice quivered. Sadness was there, just noticeable enough, to where Alvin could hear it. Alvin bit his lip, but instead of answering, he suddenly hoisted Jeanette in his arms. 
She squealed out loud, flailing a bit in his grip.  “Alviiin!  What’re you doing!?”  Jeanette kicked at the air to no avail; Alvin’s hold was too strong.  
With an idle hum and gently placing her over his shoulder Alvin just made his way to her bed, steadily crossing the floor and looking up to her middle bunk.  "Mmf, here, it's better we're in your bed, right?" He asked her as he crouched down, muscles tensed up. Jean may have been lithe, but he still had to put some effort into his jump all the way up to her bed. Jeanette let out a squeal as she clung to Alvin, closing her eyes tight.  Once they were there, he laid her out on her tummy, running his paws down her sides.
"Look, Jean… I'll be as good a mate to you as I possibly can. I swear it. And I'll do way better than that… somehow." Alvin said firmly. He moved his paws to her shoulders again, continuing to massage the tense muscles beneath her fur. "I know I made it all sound like I was only thinking about myself, but…”
He paused, bowing his head.  “Honestly, I could take care of myself.  Like, it wouldn’t be tough at all.  But I just hated seeing you girls hurting and acting weird, all because your bodies were changing up. I just hope this whole thing works out." He explained, working his paws down along her spine now.
She released a little sigh, relaxing under Alvin's paws. Was he just saying that? "Well I sure hope you're telling the truth." Was all she said, lifting her back closer to his touch. 
"I swore, didn't I?" Alvin asked. His paws moved down, grabbing the hem of her shirt, slowly raising the garment up and over Jeanette's head, laying it on her blanket and leaving her in just her purple skirt. 
His eyes traveled her back. Such lovely, dark fur... Bright, light brown lines running down as well. Soft to look at, and softer to touch, covering her lithe, slightly curvy form quite nicely. He went back to work, his paws now squeezing and kneading into Jeanette's butt. The feeling of which made Jeanette squeak again, her eyes going wide as she gripped at the blanket.
That was weird for sure. He was so… grabby. She bit down on her lip, looking back at Alvin. She liked it.
Alvin couldn't even care about her heated scent, no matter how much it forced his body to produce an erection. She was beautiful, smart and loving. But oh so timid...
"Do you believe me now?" He asked, ears perked forward as his paws went up again. 
Jeanette sighed, her body trembling as she gave him a good look in the eyes, curling her tail around his wrists and yanking his paws back down to her ass.
"I believe you." She said as she offered him a little smile.
“Heh… good.  Now lemme have some fun.” Alvin said, squeezing down on Jeanette’s butt as soon as his paws were there again.  He ducked down, pressing his face against it with a satisfied sigh.  
Her scent was amazing~  That desperate sweet allure of her heat mingled nicely with a smell close to lavender.  Perfume, perhaps?  Whatever it was, he liked it, letting out a quiet huff as he indulged.  Tongue out fully, he licked along her crotch, causing Jeanette to yelp and dig her claws into the bed below.  
“Alv- Alvin!” She squealed, tensing up from the touch.  It didn't stop him, though, both paws kneading into her butt while his tongue pushed pass her pussy lips.  
Heat indeed… as if she wasn't warm enough on the outside!  Inside was hot, wet, and gripping around his tongue as it intruded. Alvin couldn't say anything about it, and Jeanette had started grinding on his muzzle immediately, leaving the munk muffled against her crotch.  
“Yessss… e-eat me uuup…” Jeanette whimpered out.  She couldn't believe the words left her mouth, yet here she was.  Face down in the blankets with her butt sticking up to Alvin’s face.  Her tail flagged straight up with a mind of its own, keeping both of her holes on display as Alvin’s tongue dug into her.  
Trembling from head to toe, she gripped into the blanket for support, letting out quiet whines all the while.  
Alvin grabbed at the base of her tail, giving it a soft pull while trailing his tongue along her heated walls.  Most of that smell was coming from the juice within, and he kept gathering up as much as he could before gulping it down.  His other paw moved down to his crotch, gripping around the base of his dick and stroking away.  
He’d already been hardening ever since the others left the room, but now he was growing out his sheath further with every passing second.  Her taste was almost addictive, really~ 
“Mmf… C’mon Jean, climb up.” Alvin panted in between his deep licks. He laid out on his back, patting his chest and beckoning to Jeanette.  
She whined from the lack of his touch, but was hesitant to get on.  “A-Are you sure?  I don’t wanna squish you.” 
“Trust me, no one can squish me any more than Theo has over the years.” Alvin replied with a roll of his eyes.  “If I can handle that, I’ll be just fine with you, honest.”
Jeanette bit her lip, but nodded anyways.  She found herself straddling over Alvin’s face, feeling her cheeks blushing hotly as she lowered herself down.  Once more, she had Alvin smothered into her crotch, making her look down to his groin.  Alvin's arms wrapped around her hips and he began licking away again, forcing another shaky moan out of her.  
“Nggghn… l… let me…” Jeanette gasped softly, laying on top of Alvin.  Her face was right at the base of his cock, now unable to look away from it.  
She hadn't taken note of it before, but Alvin's smell was so… male.  It was hard for her to place, but she was certain it’d drive her heated mind mad.  A sort of mix between a light musk and the forest-y outdoors.  Not to mention…
His penis.  Right in her face, a growing spire of smooth, needy flesh bearing a light reddish pink color that darkened towards the tip.  Normally she would be looking away in embarrassment!  But now… she could feel her mouth water.  “Can I…?”
Not that he could answer, of course.  “I’ll uh… do this for you.” She mustered up some courage and opened her mouth, accepting his tip as soon as it touched her tongue.   The taste wasn't far from the smell, and Jeanette put her paws down on Alvin’s hips as she started to suckle.  A weird sensation at first, but she soon found herself getting into a little rhythm with it.  At least Alvin seemed to like it.  
She could feel it.  Every grunt, growl, or moan that interrupted his licking.  Alvin’s tail was swishing about in front of her.  It was kinda cute, actually, and Jeanette smiled inwardly knowing she could make him feel good too.  
The more she worked it, the harder Alvin got, throbbing against her lips and tongue almost nonstop now.  “Hrrrgn… J-Jeanette~” Alvin’s moan was paired with something spraying against her tongue.  Slick, warm, and a little sticky, she hardly had the time to taste the stuff before she had drank it.  Thankfully, more of it would come out not too long after. Jeanette found herself getting used to the slimy texture soon enough, letting some of Alvin’s pre just rest on her tongue.  
Alvin’s toes curled, claws digging into the bed.  He had to fight back the urge to start humping into her mouth, not wanting to gag Jeanette.  He pulled back from her crotch, panting to catch his breath.  “Jeez!  N-Not bad for your first time~” he praised, giving her a few pats on the butt.  “We’re almost ready for the main event!”
Jeanette squeaked at that, lifting her head up from his shaft, hiding her face against his crotch.  “Ngh, wait, I dunno yet…” 
“You… don't know?” Alvin echoed with a tilt of his head. “Ooookay, well, we can keep going if you want.  You're doing pretty good with your mouth, there.”
“Thanks.  Uh, you can sit up this time, if you want.” She told him, wiggling her hips a little as she got ready to get up. However, Alvin grabbed her tail again, making her stay on top of him.  
“Now now.  Can’t have you almost making me pop without doing the same for you, Jean.” He chided softly, sidling back to the blankets below.  “Just grab something real tight!”
Another squeak escaped Jeanette as Alvin pulled her tail, keeping her butt stuck against his face.  His tongue burrowed into her pussy as far as he could manage, lapping around without giving her a chance to flee. She bowed her head and squealed at the assault, pleasure rocking her body nonstop as she dug her claws into Alvin's thighs, holding on for dear life.  His fingers brushed against her crotch, pushing up against the edges of her vagina a few times.  
“Try not to squeak too loud at this, okay?” That was all the warning Alvin gave her.   Before she knew it, one of his fingers was beneath her tail, slicked by her own juice.  Alvin pressed it right up against her butthole and started rubbing into it.  Jeanette silenced herself by stuffing his cock into her mouth again, only a muffled groan escaping her now.   
It was more weird than having his tongue exploring her once private parts.  Jeanette wanted to kick him, or bite him, or something like that.  But as soon as his finger slipped inside, it started feeling nice.  “M-Mffn…” Jeanette whimpered.  Her toes curled up again and she found herself pushing her butt back to his paw, shaking it slightly.  
Beneath her, Alvin pulled back from her crotch, panting while he kept his focus on loosening her back door, managing to get two fingers inside of her.  “I think someone likes it in the back~. Feel like squirting yet?” He asked.  Of course, Jeanette didn't answer, so he opted to keep going, working those fingers back and forth at a slow pace to let her adjust.  “I hope you know how close you are to a r-real mouthful~” he warned.  
“A-Aaah… Al… viiin…” Jeanette leaned up until his shaft was free again, panting desperately against the head.  “I… c-can’t take it anymore. I need it in me… Pleeeease!”  Her body was on fire.  But instead of the heat she was used to, it was a simple but intense desire that coursed through her being.  Every part of her wanted it.  Wanted him. 
And he grinned at that, patting Jeanette's butt with his free paw while his fingers burrowed in that little bit deeper.  “If you say so~. Just lemme get ready.” He said before drawing his fingers out of her, leaving both her holes to squeeze down around nothing.  “Shame… I kinda wanted to paint your face.”
With a little grunt, Alvin sat up and reached into his pocket, producing one of the condoms from his jacket and making quick work in unwrapping it.  Of course, it was red.  “Well, Simon clearly thought ahead…” he mumbled to himself.  “Wanna help put it on~?” He teased, causing Jeanette to huff and look away from him. 
“Hey, your call.” Alvin hummed, setting the condom right on his tip before rolling the thing down until it reached to the base.  How did Simon know just the right size...?  He’d have to ask later if his brother had been peeking.  It felt weird around him for sure.  There was a slick substance inside the condom that made it feel warm and… somewhat tingly.  Around the middle of it, the condom was ribbed.  Alvin stroked over them a few times, gasping as he found himself digging his claws into the blanket from the sensation.  
Jeanette's mouth work was good, but surely that didn't make him so sensitive, did it?
“Hooooh man, this is gonna be interesting.” He said as soon as the blissful spike wore off.  “Alright, Jean, how do you want me?”
“Uhh…” Jeanette trailed off, finally turning her attention back to Alvin.  This was really happening.  “I… didn't think this far ahead.” She looked down to his crotch, watching the way his covered shaft bobbed each time it throbbed and flexed.  
Alvin sighed, then got on his knees.  His paws were up to Jeanette’s cheeks, lightly cupping them as he brought her face to his until their noses bumped together.  “I’ll pick first.  You can tell me if you need to change up, okay?” He offered.  
To that, Jeanette timidly nodded her head.  “Just please be gentle, okay?  I’m… i’m scared…” she admitted.  
“Of course.” Alvin planted a soft kiss right on her nose.  “Just lay on your back and spread your legs.  We'll both have fun.  And I get to watch your face while you moan~”
Jeanette huffed, her arms crossing over her chest.  “Well, that just means I can watch you all the same.” She countered before laying herself out.  She did have to fight back her nervousness in order to part her legs, though, once more revealed completely to Alvin.  She reached down and tugged off her skirt, setting it aside right as Alvin climbed on top of her.  
She couldn't help locking eyes with him again, though.  Those rich amber eyes… she couldn't look away.  The way he looked all over her face and body, so full of raw desire.  Jeanette gulped as Alvin lifted off his jacket to throw aside, putting himself on full display for her as he leaned in, his paws resting aside her head. 
“Alright Jeanette… want me to do it quick?” He offered. “I heard it can hurt the first time, but that's all human stuff and-” he went quiet as Jeanette reached a paw up, cupping his cheek.  
“Quick, please.” was all she said, offering a little smile too.  “If it does hurt too much, you’ll know.”
Jeanette squeaked quietly as Alvin angled himself to her, the head of his dick poking around her crotch.  He had to readjust a few times, but soon enough his tip had shoved inside of her.  And, as requested, Alvin grabbed Jeanette by the shoulders before making a full thrust forward.  
“A-AAAHH!” Despite being held down, Jesnette managed to lurch up, her arms wrapping tightly around Alvin as pain spiked through her core.  
'O-Okay, definitely should have gone slower instead.' Alvin thought, unable to voice his agony.
Jeanette's claws were digging deep in his back, dragging downwards as he pushed his way in. Her scream was quickly muffled by Alvin kissing her mouth, cradling her body tight despite the pain, powering through to comfort her.  Though, admittedly, he nearly screamed as well.  
He hadn't noticed if he went through a barrier or not, but Jeanette sure reacted like he did.  He waited for her cry to die down, swallowing back his own. "Gah, c-calm down, Jean, it's okay!" Alvin said, breaking the kiss and cupping her cheek in his paw, making her look him in the eyes.
Jeanette’s eyes quickly squeezed shut, though, and her tight grip on Alvin's body only got firmer. Her breathing was heavy and shaky, filled with whimpers as she somehow managed to squeeze him even tighter, keeping him in place as she trembled against him.  Tears streamed from her eyes as she fought through the stinging sensation burning in her loins.  
“Was it too much?” Alvin asked through gritted teeth.  As much as her claws hurt, he still brought a paw up to wipe her eyes.  Alvin could still feel every clench of Jean's walls. And with that, a resounding but light pleasure that helped him through the pain.  
"Alvin... Just... hnnn… don’t.  J-Just don’t move it." Jeanette grunted out through the stinging.  Minutes passed by, her grip on his body slowly weakening as she ended up laying against the blankets again.  Soon, the pain was gone, only leaving behind a weird sense of… fullness. But it was much better than the burning sensation of her heat. “Gosh, that hurt, but… y-you can start now.” She told him, finally opening her eyes again. 
Alvin winced slightly, but nodded his head. "Tell me if it's too much from now on, alright?" He asked, starting to kiss along her neck as he moved his paws down to her hips, keeping her lower half lifted off the bed as he dug his toe claws into the blanket for a steady hold, giving slow, deep thrusts into her newly taken tunnel.
Jeanette simply laid there for the first few humps, looking up at Alvin. The way his eyes slid closed slowly, the light rippling of his muscles... The way he started to moan in her ear... Jean leaned her head up, then kissed him on the neck a few times, giving her hips a slight wiggle as she ran her paws down his back. "I'm sorry if I caused a scar." She said, only to moan out as Alvin slipped in further. 
She quieted herself, hiding her face against his neck again. Her heat had faded away fast and pleasure was quick to take its place.
"I-It's okay, you really needed to let it out." was Alvin's response, flashing her a quick smile as he squeezed her hips firmly, his thrusting starting to get a little rougher as his tip prodded away at her inner walls, spreading her out that little bit more every time. He could feel a blush on his cheeks as Jeanette's tail wrapped around his, giving it a soft tug. 
Their eyes met, and Alvin was lost in her purple gaze. Whatever fear or worry that was there before... All gone. Just clear purple pools that he could stay in forever.  Alvin rested his forehead against hers, their bodies rocking back and forth, keeping to a gentle, slow tempo. It wasn't the wild fuck he imagined, but... It was still enjoyable. Feeling every last nook and cranny of Jeanette's sensitive walls as they clung to him, pulled him in more, and then released, just to squeeze on down again, adding more of her warm juices to his already soaked shaft.
Her soft moans in the air, mixed in with Alvin's harsher grunts of bliss, producing the melody of their arousal, tails coiling tighter with each other. Jeanette hooked her arms around Alvin's neck, her back arching delicately while she wrapped her legs around his waist as well, giving him full control of their movements as her toe claws lightly gripped his rear.
"H-Harder…” she panted out. “Alvin, I-I want it harder now..." She pleaded. Alvin obliged, lightly pressing his claws into Jeanette's hips. His humping got harsher, swinging Jeanette's hips back and forth, their crotches now meeting with a dull, wet 'slap' sound each time as her juices started to flow out.
That's when Jean got louder.
Something about the mess, feeling it all stirring within her inner being.  Her tender, formerly untouched core now being pleasantly ravaged, even the ribs of the condom made her body quiver. The light grinding Alvin did every time he burrowed into her just worked them in more.  And the way his tip kept pushing again and again on her deeper folds had her head spinning.  
This… this is what they’d been skipping on for so many years.
She gasped, only able to take it for a few thrusts more. “Ahnnn…!  Alvin, oh gosh, Alviiiiin…” She started squirming, releasing her grip on his body. Orgasm was creeping in again and she didn't want the ride to stop.  Even with every inch demanding that peak of satisfaction, she couldn't.   Not yet. 
"O-Oh, Alvin... Can we try, uh, s-something else?" She panted, moving her paws down to Alvin’s hips to try and hold him in place.  Alvin let out a groan, making a few more humps into Jeanette before he had to slow himself to a stop.  
“Hrrngh, what’s wrong?” He asked, peeking an eye open to see her. “C’mon Jean, I was r-right at the edge again…”
“I’m sorry, sorry, I-I was just, well… you know.” She admitted with a soft huff, looking away from him.  “You almost made me… squirt…” she admitted, the word getting her to blush as she covered her face with her paws.  “And this feels so nice…”
Alvin couldn't help smirking, but he obliged her and pulled out, bringing his paws up to hold hers.  “Glad I can get you close then~. But you do what you gotta.”
Sighing, Jeanette tilted her head into his touch, her bushy tail thumping against her bed a few times before she nodded.  “Alright, alright.” She said, then laid down on her side, cheeks blushing once more as she lifted up her leg, beckoning him with her tail. "S-Sorry I keep changing my mind, but… Like this, please.  I promise it’s the last time.”
"Heh. Whatever works for you." He replied, his tail swishing as he moved after her, grasping her ankle and holding it up for her, wasting no time in pushing his way back inside of her beckoning slit.  “If you ask me, it just lets me see you from more angles~” 
Stirring his shaft around a bit before starting to thrust again, Alvin burrowed in deep each time, pounding in straight to the very hilt and getting a loud moan from Jeanette every time his hips smacked against hers.  Watching her drag her claws in the blanket, he rubbed along her raised foot between his humps. 
“Your toes are kinda cute when they aren't tearing into me~" Alvin commented, giving her a soft kiss on the pad of her paw as her toes curled lightly on his nose.
“S-Sorryyyy…” Jeanette whined softly, flexing her toes again as she arches her back once more. Her body was on fire with bliss, urging her closer and closer to her climax.  She couldn't even explain it.  The shocks of pleasure, the labored bliss on Alvin’s face, and the way her own body demanded for that intense rush; it all made her head spin.  And they had just started again but…
“Alvin, I think I'm getting close a-again… oh god I can f-feel it comiiiing!" She whined, biting down on her lip. She couldn't help it, but the more she was plowed, the more her mind wandered; playing out different scenarios to fuel her horny mind. 
What a sight she must be.  A sweaty, whimpering mess, her hair and glasses completely askew, being made to watch herself as she was taken from behind and ravaged so blissfully… If it was possible, she could have sworn she'd gotten wetter from that.  She’d have crossed her legs if it weren't for Alvin pistoning away.  He was no Simon, but at least it felt he was being very attentive with her.  
"G-Gah... Jeanette, you're squeezing a lot now." Alvin's voice broke her thoughtful trance, making her look up at him. Something deep within her wanted to tear off the condom and have him really fill her up... But she had to save that for later.
"Do it, Alvin!" She begged, biting down on the blankets as she hid her face in them. However, Alvin released her foot, laying down on top of her completely and rolled her over, bringing her into a kiss.  He grunted, or moreso growled, into her mouth as he gave her a few more rough thrusts before burying himself inside of her completely, moaning as he reached his climax. “Jrhnnt!”
She didn't feel much at first, but after a few spurts and throbs, there was a new warmth growing inside of her without a doubt. The condom was swelling up within, and the sensation sent shivers along her spine.  Alvin must’ve been pumping out so much…
Jeanette whined, holding Alvin tightly as she wiggled her hips, her own orgasm taking hold soon after, causing her to release her own warm, sticky juices all over him, most of it splattering against their crotch fur.
Once their afterglows hit, both chipmunks were left panting against each other's necks. Alvin recovered faster, slowly dragging himself out of her, removing the full condom and just letting it fall on Jean's bed, not caring if it made a mess or not. He just pulled Jeanette closer, getting her into another hug. He started kissing up her neck. 
He didn't need to ask if she enjoyed herself. The blush on her face and her exhausted breathing was more than enough.  However….
"...rrhf. Hey Jean?"
"Yes?"
"Your paws are, like, all on the scratches."
"O-Oh! Sorry…" Jeanette adjusted her arms, holding on to Alvin's sides more now.
“Heh, it’s okay… you say sorry a lot, y’know?” Alvin teased, receiving a weak punch on the arm from Jeanette as he laughed, nuzzling his nose against hers. 
They'd be switching soon, so he opted to just cradle Jeanette, happy to spend the rest of their time together as close as he could.  ‘Maybe this wasn't such a bad idea after all…’ he thought.