Vinny sat up in her bed, her sleep interrupted a few hours later. Behind her door, she could hear faint noises.  Something clattering around... then it dawned on her. 

Someone was rummaging in the kitchen.

She climbed out of her bed, grabbing her powder blue robe, making sure it was tied tight before she tiptoed out of her room.

'Don't worry. Probably just a mouse… er… a very big one... Or one of those raccoons.' Vinny thought.  She steeled herself, putting on a brave face as she entered the kitchen.

To her surprise, it was only Theodore. He was dressed in a simple green onesie, zipped up about halfway with one of the buttons in the back undone, showing off a little bit of his white undies beneath. He even had a little "T" stitched on his chest.

Vinny let out a sigh of relief, going over to him. "Theodore, sweetie, what're you doing awake?" Wincing a little from her voice, Theodore turned around slowly, revealing a bowl of soup nestled in his hands.

"I woke up feeling hungry... D-Dave usually tells me not to eat after bedtime, but this was so good I couldn't help myself!" He admits, bowing his head a little. 

Chuckling, Vinny couldn't help but smile, giving him a soft kiss on the forehead. "Oh, sweetie... " She started, taking a step back. "I didn't see a thing." She told him with a sly wink.

Theodore smiled back at her, wiggling a little as he makes his way to the table. Vinny stopped him though, taking hold of his hand. 

"Let's... have a little meal of our own, shall we?" She guided him along to the living room, sitting down on the couch and patting the spot at her side. 

As Theodore began to eat, Vinny took a deep breath. He looked so happy just chewing away… Maybe the cooking she had done for them before rubbed off on him? She reached an arm over his shoulders, gently rubbing along his shoulder and side. "Hmm… Theodore, can I ask you something?"

He paused, lowering the bowl and letting out a little burp, wiping his mouth clean. "Yes, mama?" His ears twitched slightly as Vinny's paws moved down, brushing along his lower back. 

"You boys have gotten so big… I was wondering if your tails have started to grow yet. Your shirts are so big, they were covering it up earlier."

"Ohhhh… Yeah, mine did!" Theodore answered with a nod, picking at the soup for a few chunks of acorn, chewing them up eagerly. 

"Really now?" Vinny put her paw down to the couch.  "Do you mind if I saw it?" She asked. 

Almost immediately, Theodore had stood from his seat, setting the bowl to the side as he reached back to unbutton himself. 

'Huh... this may be easier than I thought,' Vinny thought. 'I didn't expect him to be so quick to do it.'

She watched as Theodore, after adjusting himself a little, started to tug at his underwear through the hole of his onesie, wriggling until he finally managed to pull them down.

Other than being able to see a little bit of his butt, Vinny smiled a little wider at the sight of a bushy tail. Or rather, the start of one. It was only about five or six inches or so, and had a noticeably darker stripe going from base to tip, just like he had on his face. As Theodore wagged it around proudly, she couldn't help blushing.

If that's what he's like in the back, what would the front be?

She forced that thought aside, beckoning him back over. Once he was close enough, she took hold of his zipper and started to bring it down. "Aw look… You've got a little mess on you." She chided softly. "Now how about you lose that, and I'll get it clean for you?"

Theodore blushed, crossing his hands over his crotch area. The onesie slipped down onto the floor. All he wore now was his underwear.

A light grin was on Vinny's face. Knowing he was shy just made things a little easier for her. "Oh, come here, sweetie." She says, patting her lap softly. "How's about you get cozy here, and mama will help you get ready for bed again?"

She started to slip out of her robe, having not worn anything to bed. Even in the fall, it could still get kinda hot inside. It was strange, though, that Theodore was able to wear a full onesie without a problem. 

Theodore hesitated, his eyes going wide at the sight of Vinny's gently curved form. Seeing her like that… it made him want to look away, but also to get as close as possible.

"O-Okay…" Theodore sat back down on the couch, resting his head on Vinny's lap, looking up to her face. Well… her breasts. Two nicely sized, lightly furred mounds right on her chest.  He could see two light pink nipples, and there was a familiar smell about his mother now. It was something warm and comforting.

Vinny gently cradled his head, smiling softly at him as she guided his head towards her chest. "Now, I know it's not quite … normal at this age, but I know for sure that you always got sleepy when I did this for you when you were a little pup." She says, one of her nipples rubbing against his lips.

Blushing, Theodore opened his mouth instinctively, gulping softly as he fit the little bud in his mouth, sucking on it softly.  The action just felt... right to him.  Within seconds, Theodore's eyes were closed, and he was nursing away at Vinny's nipple. 

"O-Oh dear… You got into that quickly, didn't you?" Vinny trembled visibly as she bit down on her lip. It had been far too long since she felt a sensation like that… She moved a paw down to gently caress Theodore's belly, humming softly as she let him continue to suckle.

Vinny closed her eyes, biting back the urge to moan. How long had it been since she had nursed him? She'd never let out a moan before, but now here he was, treating her teat like some sweet candy. Something about it was so… right… She shuddered again, continuing to rub around Theodore's belly, even lightly squeezing it in her hold. "Oh… Oh Theodore…" Vinny tilted her head back, finally letting out a little moan.

She moved her paw downwards, a heavy blush settling on her face as she felt something… stiff. Peeking down, her eyes widened at the sight of a bulge forming, on Theodore's crotch, a little dark stain present at its very tip. 

Theodore squeaked out loud, releasing her nipple and immediately pushed at her paw, shaking his head. "M-Mama, don't touch that!"

"Oh Theo…" Vinny gave him a little kiss on the forehead. "Just let mommy take care of that for you." she insists. "It must be so cramped having to keep it all in your undies, right?" Theodore just bit his lip and nodded. "W-Well, uh... yeah, but Dave said I shouldn't let anyone see it yet…"

Vinny offered a little smile, gently brushing back his hair with a paw. "Sweetie, I already know what it looks like." She tells him while slipping her other paw into his underwear, gently taking hold of his length. When he tensed up, Vinny gave him another kiss, this time on his lips. "Don't worry… We won't tell Dave." She whispered in his ear. "So, let's just... have some fun together, okay?"

Whimpering, Theodore nodded his head, shivering as he gave a weak thrust into her hold, his tail quivering beneath him as he latched onto her nipple again, licking away at it and even nipping it, trying to distract himself from the new pleasure rushing through his body now.

The same could be said for Vinny, whose toes curled up in delight as she summoned the courage to pull Theo's underwear down. Looking at her youngest son, she couldn't help but blush, seeing him all naked and chubby in the warm light. And the sight of his shaft and balls… Well, he wasn't little. In fact, his length was just about the size of his tail.

"M-mama…" Theo squeaked, embarrassed at being in the nude. But Vinny gave her son a hug, as best as she could, letting their warm exposed bodies rub against each other. His tongue was warm and soft on her nipples. 

"Gnnh! O-Okay… You keep that up and I might leak…" she moaned.

"What do you mean by leak…?" Theodore asked timidly. He didn't need an answer. As soon as he went back to suckling, he was met with that familiar taste. Warm, smooth, a little sweet and creamy; milk had dripped onto his tongue. The taste was so soothing, it made him relax almost instantly, nearly going limp as he let Vinny hold his head up.

"Oh gosh, sweetie!" Vinny squeaked. She hadn't been lactating for years… or so she thought. "P-Please, don't stop…" She pleaded, her paw working along his length faster as she parted her legs, releasing his head in order to reach down between her legs, running a finger along her slit.

Theodore moaned around her breast, steadily drinking down her milk, some of which dribbled from the corners of his mouth as he humped towards her paw. "Mmmnh! I-I like that…" he managed to say.

Motivated by his moaning, Vinny picked up speed just a little, focusing around the tip of his length to spread the precum around. "That's good, Theodore… Just let that good feeling go through you." She cooed softly, lowering her head to kiss his forehead as he fed from her.

"Mama... I-I think something's trying to come out!"  Theo squeaked out, gulping another mouthful of milk.  He started to sit up straight, but Vinny nudged him back down.  

"Shh, It's okay, sweetie. Just let mommy know when it's ready." Vinny encouraged, giving him a light bounce on her lap as she adjusted her grip on his throbbing cock, lightly cupping his balls in the process. "Have you ever done this yourself? All this rubbing?" She asks.

Theodore groaned, pulling off of her nipple and panting heavily, his toes curling against the couch cushions. A strong warmth was forming in him, building up at his base, making him squirm about. "I-I did, but it never got like this. Not all hard and leaky... Ahnn!  A-And warm!"

Vinny nods slowly, carefully moving his head back to her breasts. "Don't squeal too loud from this, sweetie." She tells him. Right as he was about to ask, he moaned out at the top of his voice, his back arching off the couch as Vinny grasped him firmly at the base, jacking him off rapidly.

Quickly, Vinny put her nipple back into his mouth, eyes wide as she continued to stroke him off. Alvin or Simon could have heard him…

Her thoughts were broken when Theodore let out the loudest moan he could muster from being muffled, followed by a few heavy, sticky splatters landing right on her cheek and chest. Her cheeks burned with a blush as she stroked him through his very first orgasm.

Theodore kicked his feet a little, his little claws digging into the couch cushions as he whined and moaned. His mother's milk just tasted so good… It made him feel nice, and now that build up was being released all over her. "Gaaaah… M-Mama, that feels… oh wow…" He mumbled, almost fully sprawled out now.

"Shhh... I-I know, sweetie." Vinny says as she starts to lick her paw clean. Thankfully, he had some sweetness to his salty flavor. "So, that was really the first time you ever…" She paused to look down at him. "Er, first time you ever squirted that stuff?"

"Yes… And I didn't even know I could make milk!" Theodore answered, playing with some of his own sticky white spunk, watching as it clung and stretched between his fingers.  

Vinny couldn't help but laugh. "Well, it's a very special kind of milk.  Something only a boy can make." She tells him, giving him a kiss on the forehead. "And you'll be making more once you meet your special someone." She encourages, climbing off of the couch, going to retrieve her robe. 

"W-Wait!" Theodore said, letting out a squeak as he rolls off the couch, landing on his tummy. Pushing himself to his feet, he took a few shaky steps towards her, wrapping his arms around her hips. "What if… What if I already met a girl?" He asks. "How am I gonna make more milk then?"

Blushing, Vinny stooped to give Theo a pat on the head. "Oh, well, I-I'm sure you'll find some way. But for now, how's about we go back to bed? We have a lot to do tomorrow." She says, giving him a light push.

Making him shoot was one thing. But could she push herself to go further?

As if to answer her thoughts, Theodore wrinkled his nose, squeezing her a little tighter. "P-Please show me how, mama! Just once? I promise I won't forget it!"  He gave her his best puppy eyes, his little tail tucking down against his rear. Vinny looked away nervously, but sighed. After all of that, she couldn't just leave him. Especially since he might not know what to do next time.

"Okay… Okay. Mommy will show you." She agreed, crouching down a little to kiss his nose. "But only this once, okay? It's something you should only do with someone you trust."

"But… I trust you a lot." Theodore replied with a tilt of his head. "Does that mean we can do it more than once, then?" 

The question nearly made Vinny sputter. "I-I… We'll see, honey. It's not exactly something that happens a lot." She answered.  "Let's just get to it, okay? We'll talk more tomorrow." She insists, taking hold of his paw and leading him out the room.

__________________________________________________

"Uh… Are you sure about this?" Theodore looked up at his mother.

Vinny had moved them to the dining room, sitting herself down on the table in front of him, her robe draped lightly over her and her legs spread enough to reveal her soft pink core. Right by her side, she had a small bowl of soup at the ready. Dipping a paw into the creamy brown liquid, Vinny began to smear the warm soup onto her fur, mainly around her belly and thighs.

Theo could only watch in amazement, his mouth already drooling with excitement.  "What're you doing...?"

"Mmm... Well, sweetie, it's just to make you a little more comfortable." She says. "So, all you have to do now is use your mouth until your… thingy is stiff again."

"Okay, mama." Theodore's fuzzy cheeks were a bright red, but he went straight to work. Sitting down in a chair, he scooted up into his mother's sweet-smelling fur, burrowing his nose in while he started to lick the soup up from her. His tongue made quick work of cleaning up Vinny's stomach while he nibbled lightly at the acorn chunks scattered around her fur.

Tilting her head back, Vinny moaned out, not bothering to keep herself quiet now as she curled her toes, scooting her body a little closer to Theodore. "Aah… You're doing good so far, sweetie. C-can you clean down there? N-near my legs?" She reached down to ruffle up his hair affectionately.

Nodding his head, Theodore shifted his paws to grab his mother's rear and lifted her up a bit. His tongue moved across Vinny's navel, licking away all the soup he could find, all the while caressing her butt absently and moving his head down towards her crotch.

He paused then, just staring at his mother's beckoning wet slit, watching the soft pink folds of flesh shudder and seethe ever so slightly.  His tail wagged on his own, and all he could do was look up at her face again. 

"A-Ah…. come now, Theodore… don't stop now…" Vinny pants, bucking her hips towards him. "Please, sweetie…"

"Does this... feel nice for you, mama?" Theodore asked curiously.  

Vinny bit her lip, trembling as she made herself sit up a little.  She'd be lying if she said she wasn't.  And she couldn't lie to such a sweet face. 

"Theodore... yes, yes it does.  Could you keep going?  For me?"

Her begging was answered soon enough. Theodore smiled, dipping his head back down between Vinny's legs.  Then, he forced his tongue inside of her, already lapping up and down her inner folds rapidly as he gripped her thighs firmly, pulling her even closer to him. "M-Mmnmph!" There was a cute grunt from Theo as he savored the strange new taste, all while his tongue kept jabbing away at her inner walls.

Vinny arched up, quickly clamping her paw over her mouth, moaning into it and grasping a fistful of tablecloth. Gosh, was he good at this. She hadn't had anyone's tongue work that well since...

'Ohhhh God... just like his father...'' Vinny thought, panting hard through her nose as she gripped at Theodore's hair, tugging on it softly as she wrapped her legs around his shoulders, trying to pull him in further.

"M-Mmnh! Mama, my thingy's all hard again!" Theodore squeaked out between licks, somehow managing to pull back from her sweet honeypot. 

Whining softly, Vinny nodded her head. "Aah… Alright, sweetie… Stand up and p-put it in me." Vinny instructs. "When you do this with your girl, she's going to have a little barrier you'll have to go through. It may hurt, so make sure you comfort her plenty until she says so."

When Theodore stood up in the chair, she gave him a little encouraging smile, then glanced down. There it was… his length pulsed softly at her entrance, prodding at her outer folds lightly.

"Uh... put it in?  Are you sure?" He asked, his paws resting on top of her belly as he leaned forward. "I don't wanna hurt you, mama."

Vinny took a deep breath, gazing into his face again. Such confused innocence he had… and yet, there was a hint of that primal desire in his eyes. She nodded her head. "I'll be okay, sweetie.  Mommy's already done this before, remember?  Go ahead. It'll be fun for both of us."

Reassured, Theodore nodded obediently and lowered his head to her chest. He wrapped his arms around her firmly, hesitating for a moment before giving a quick thrust that buried his tip inside of her slit. Slowly, inch by inch, the little chipmunk eased his dick into Vinny, rubbing up on her walls and resulting in a series of moans from both mother and son.

Vinny arched her back once more, holding on to her pudgy son tightly as she wrapped her legs around his hips. 

All the years had made her almost forget just what mating felt like, and now she felt both regret and satisfaction at once. Her youngest boy… Making her moan like this. Holding him closer, she let his head rest on her breasts once more.

"Oohh… T-Theodooore…" she gave him a few light nips on the ear. "You can start moving now."

With a nod of his head, Theodore steadied himself in the chair, feet planted firmly on it as he placed his paws at either of Vinny's sides, looking up at her with a mix of pleasure and confusion in his eyes. Slowly, he began to thrust, going at a steady, gentle pace. It didn't take long for him to bow his head again, hiding his face between her breasts as he moaned, shivering noticeably.

"Ahh… Now now, Theodore…" Vinny cupped his cheek lightly, raising his head until their eyes met. "You don't want to look away. Especially on the first time." She tells him, lightly scratching behind his ear to encourage him.

"Y-Yes mama.  I'm sorry, it just feels so good!" Theo panted, trying to keep his gaze on her face as he lowered his head again, this time just taking a nipple into his mouth and suckling at it.

Their moans mingled as they rang out, softly echoing against the walls. Vinny's tail wrapped around Theo's waist, lightly tugging him closer to her while her walls clamped around him softly, milking his shaft. She tilted her head back, moving a paw down to rub against her clit, biting down on her lip. "Oh, j-jeez, Theo…!" Vinny moaned, closing her eyes tight. "You're making mommy feel so good!"

"Y-yay!" He squeaked out proudly. "I feel good too!" Theodore's little tail wagged side to side as he steadily got rougher with his thrusts, precum spurting against Vinny's walls each time his shaft pulsed. He focused on her nipple again, holding it firmly in his mouth as he suckled away on it, eager for her milk. Lucky for him, he didn't have to wait for long. Fresh milk was flowing into his mouth in no time, which he eagerly gulped down.

Vinny's toes curled against his rear, her claws digging softly into his butt as she tried to pull him even closer, letting her walls clench down around him, urging more and more of his precum out. Gosh, did he squeal. Vinny had to grip his head and hold him down to her breasts just to keep him from getting too loud. "T-Try to stay a little quiet, sweetie. We don't want to wake your brothers, do we?"

Whining, Theodore's gaze met hers once more, an all too familiar look of desperation in his eyes. "I-I'm sorry, but it feels like it's gonna burst again!" He pants, milk drooling out of his mouth as he just kept pounding away, driving his length against her inner walls harder. "It's gonna come out! I c-can't stop it!"

"J-Just let it out then sweetie!" Vinny encourages, biting down on her lip nervously. "I… I'm close too. So we'll feel v-very good together!" She leaned her head back again, panting heavily.

Here she was… A sweating, moaning, milking mess… All caused by her youngest. His hips smacking roughly against hers, the wet slaps of impact as their mix of fluid bathed his length… 'My baby boy… About to make me cum..' She couldn't help but chuckle inwardly. It sounded so wrong, but felt so right in the moment. 

Theodore suddenly pulled back, letting out a loud moan as he pushed his way into her one last time, his toes curling and his claws tearing at the tablecloth as he reached that blissful peak once more. Vinny winced visibly from the force, only to moan out as well as the feeling of fresh, hot cum splattering on her walls seared through her, driving her into her own orgasm.

How long had it been since she last felt a male filling her? Or even just her pleasing herself? She couldn't quite remember. Her mind was gone for now, completely lost in ecstasy. Theodore had made all of that fade away, giving her newer memories.

"Uhh... M-Mama did you... did you just pee?" Theodore asked, snapping her out of her stupor. Vinny blinked a few times, looking down at him. Sweat was matting down some of his fur, and that blush of his had stayed stubbornly. She smiled, raising a shaky paw to cup his cheek. "Oh, sweetie… It's much better than pee." She said, slowly sitting upright and hugging him, keeping his shaft buried inside of her. "You made mama cum. And that's what you'll want to do for your special girl." She told him.

"Oh… So I'm not making milk then…" He looked up to her, making their noses bump together. "I'm gonna make sure Eleanor feels just as good as I do!" He promises, that little tail wagging away once more.

Laughing softly, Vinny placed a light kiss on his nose. "Hehe, alright sweetie. Now… Grab your clothes and head back to bed. It's late. Goodnight." She instructed , scooting back slowly until his length was free, causing their mix of cum to flow out. When Theodore's attention went to the forming stain on the cloth, Vinny waved her paw dismissively. "Don't you worry about that. I'll clean it up."

And with that, he was off, taking slightly wobbly steps as he gathered his onesie, heading back towards his room. "Goodnight mama! And thanks for letting me have more soup!" he called.

Now alone, Vinny sighed softly, looking down at her slit, thankful that her baby making days were behind her. "So pent up… Ah well…" She took in a deep breath, laying out on the table. Once the tingling afterglow was gone, she'd clean up.

'That's just one down, Vinny.  Two to go.'