"Hello? Dave Seville speaking. Oh, Hi Vinny, what's up? Are the boys giving you trouble?"

Vinny sat on her bed, her feet swaying a little as she held the phone to her ear. "Uh… Hey, Dave. No, the boys are behaving just fine. I was just calling to ask you something… It's, well... it's really important." She spoke softly, looking to the door. She could feel a lump forming in her throat, trying her best to keep it down.  "You uh... you know the situation we had last time?"

On the other side of the line, Dave just cleared his throat. "Go ahead, I'm listening." He spoke.

"Okay… So, here's the deal…"

__________________________________________________

"Mom? I'm coming in now." Simon called out.  He knocked at Vinny's door a few times before simply walking in. The first thing he saw was… an empty bed. Raising an eyebrow, he peeked around the room. "Uh… Mom? Are you in here?" He almost jumped as he heard the door close behind him.

"Oh, don't you worry, Simon. Mommy's here." Vinny says, a slight hum in her voice. She approached him from behind, wrapping her arms around him. "Are you ready, sweetie? You seemed a little nervous earlier." She asked him.

Simon then turned around, blushing softly at the sight of his mother. She wore only her robe, the front open just enough to keep her cleavage exposed.  She had a flowery warm scent to her now. Simon breathed it in a little, gulping.  "I… I'm ready. More than I'll ever be." Simon says firmly, nodding his head. Gosh, was she pretty… "I just hope I do good enough." He says, only to squeak softly as he was brought into a firm kiss, Vinny gripping him by the shoulders to keep him in place.

Trembling all over, Simon soon melted from the kiss, his eyes closing a little as he copied his mother, locking lips with her and tilting his head to the side some. He let out a little sigh, giving her a gentle hug in response, his paws resting on her shoulders as her tongue poked into his mouth. It made him tense up, a heavy blush forming on his face as he pulled away, shaking his head. "G-Gah! Oh… S-Sorry, Mom, I just… I wasn't expecting that."

Vinny only smiled again, reaching for his paw as she led him to the bed. "Tsk, tsk.  My my, Simon. You know you'll need to get used to it if you're going to be with that Jeanette girl. I'm not sure, but I think she would enjoy a good kisser." She tells him, letting him sit down on the bed. Eyeing him up and down, she swished her tail a few times. "Now then. How's about we lose our clothes, hmm? I'm sure we won't be missing them."

"Eheh… right you are." Simon replies, biting down on his lip as he slipped out of his shirt, putting it down neatly before raising his legs, hesitating for a moment before he tugged his pants off. Vinny couldn't help blushing a little as he sat there in his undies, her tail sweeping over the floor as she looked over his body.

Obviously, he was the most lithely built of her three boys, though he still showed a little bit of natural curviness, courtesy of herself most likely. Lean muscles were noticeable as well, most visible whenever Simon moved. 'Someone must've been working out...' she thought.

Removing her robe, Vinny took the first step, putting her paws down on Simon's thighs while she planted a light kiss on his neck. Her light, supple hands took hold of her son's undies, slowly pulling them down from his waist, letting them slip over his thighs.

"Gosh… Well, you're really frisky, Mom." Although Simon had exposed himself in the nude on several occasions, tonight felt unusual, almost as if he was doing it for the first time.

"Of course, my dear. I'd like to get you prepared. You can think of this as… practice for your special girl." Vinny leaned in closer, pressing herself against Simon's naked figure. She planted a kiss on his nose.

"Thanks Mom… But I suppose for tonight, you can be my special girl." Simon returned the kiss, taking the advantage of slipping off Vinny's robes. When the garment was pulled apart, he marvelled at the sight of his mother. Even the whiff of lavender that was coming off Vinny's body… it made Simon's senses tingle. He closed his eyes as he buried his face into Vinny's chest, breathing in deeply. Curious, Simon stuck his tongue out and began to lick away.

Vinny blushed, letting out a soft moan at the feel of her son's tongue rasping against her chest. "Oh my… Haahh… A little experiment of yours, Simon?"

"Nuh-uh," Simon paused, a trickle of drool lingering from his lips. He moved up to lick Vinny's shoulders. "I believe that... It's part of our grooming rituals in the wild… I'm sure even advanced chipmunks like us do it from time to time... assuming we can." He spoke in between licks. 

Vinny could have asked Simon to stop, but she didn't want to. Secretly, she did like the idea of getting a tongue bath.  And from her son, which made it better. "Are you still feeling awkward?" Vinny asked, earning a smile from Simon. By now, her shoulders were slightly damp from her son's meticulous grooming.

"Maybe… A little," he said honestly. "But I'll get over it."

"That's my boy."

With a slightly confident nod, Simon continued the licking, this time focusing around Vinny's throat and chest area, bringing his paws up curiously to grasp her breasts. His eyes widened, however, when he felt an odd, warm, creamy substance there. "Uh… Mom? Are you… lactating?"

"I know, I know, it's strange." Vinny sighs, trying to keep herself close to his paws. "But… please, continue touching them. It feels wonderful." She says, gently rubbing his shoulder.

'But how...?' Giving her a confused look at first, Simon looked down to her chest, giving her soft, ample tits a few gentle grope, his tail swaying side to side as he did so. The more he did, the more her milk leaked out. Overcome with curiosity, Simon sampled the familiar substance off his fingers, shuddering from the somewhat sweet flavor that spread over his tongue.

He closed his eyes, sighing softly as he holds his head back. It brought back such wonderful memories, no matter how small. Snuggling up with his mom on the bed… His first real book he could read on his own… The sound of his mother's soft, melodious voice as she sang him and his brothers to sleep…

"Uh, Simon? I think you like my milk more than both of your brothers combined." Vinny says, snapping him out of his trance. When Simon opened his eyes, he blushed brightly at the sight of Vinny, her cheek pressed softly against his newly hardened shaft. She was tugging on the foreskin a little, her tail wagging with amusement. "Not even Theodore got this stiff so fast from just a drink."

"A-Ah! Oh, gosh!" Simon squeaked, hands going up to hide his face as his blush flared anew. 

"Oh, sweetie, it's too late for hiding." Vinny cooed softly, reaching her other paw up to cup his cheek. "Just relax for me. Please?"

With a little whine, Simon nodded his head, moving his paws back to the bed, spreading his legs apart to give her more access to his crotch. Vinny wasted no time, grabbing his shaft in the middle and giving it a few gentle tugs, ignoring Simon's little groans of protest as she slowly managed to get his cockhead completely free from his foreskin, listening to his relieved sigh with satisfaction. "Much better now, right?" She asks, tail swishing.

"Aah… Y-Yes, it is.  I've done it before." Simon answers, adjusting his glasses a little as he moves his paw down, lightly patting her head. "Please, can you… you know."

Smirking, Vinny shakes her head, giving his cock head a gentle squeeze. "Ah ah ah, Simon. You have to be completely clear with what you want. Or else I could end up doing something different. So… What is it you want?" She emphasized herself by giving his tip a soft lick, relishing in his resulting moan.

"M-Mom, please!" Simon begs, his claws digging into the blankets, a rough shudder working up his spine as his shaft throbbed in response. He closed his eyes tight, biting down on his lip as he tried thrusting towards her mouth. "I can't s-say that… Not to you..." he mumbles when she refused another lick.

"Tsk tsk, Simon. How are you going to be a good partner if you can't even voice your wants?" Vinny comments, pinching his foreskin lightly and tugging it up a little. "I'm afraid I can't do anymore until you say it." She tells him. Then, she reached up her free paw, gently pushing him down on his back. "This'll be your last chance, sweetie. Or we can just call the night off."

Simon whined softly, looking away as he hid his mouth behind his paw. "I-It's inappropriate… to say such things in front of your parent." He responds, to which Vinny just shakes her head. "You definitely got your father's smarts. And stubbornness." She sighed, lightly scratching through his soft fur. "But I honestly can't see how we'll you'd do for your special girl if you can't even tell her what you'd like."

"M-Mom I want you to…!" Simon grit his teeth for a moment. "I… I want you to…" he fell silent again, blushing brightly.

Pouting, Vinny grabbed hold of his balls, giving them a firm squeeze. "G-Gah! I want you to suck my cock until I c-cum!  I want to feel your tongue on my dick as you lick up all my semen!!" Simon yelped out. "I wanna be able to enjoy this with you like Alvin and Theodore did! And I don't want to be so n-nervous around you!" He moans, tearing into the blanket below. Simon, realizing what he'd done, immediately covered his mouth again. "I… I mean…"

Vinny's cheeks were noticeably dark with a blush. However, she still smiled at him.  "Shhh. I know exactly what you mean." Vinny says, trailing her paw down to his belly. 

"You… y-you do?" Simon gave her a wary gaze, slowly moving his paw from his mouth. Vinny laughed softly. 

"Why, you just told me." She answered. Before he could comment, Vinny opened up her mouth, taking him in up to the middle of his cock, continuing to play around with his balls, carefully tugging on them to add to his bliss. His moans were loud and precious, a gentle welcome assault to her ears as she let him sit up, holding herself steady.

Simon, catching her drift, nodded his head as he holds on to the back of her head, grunting lightly as he started humping in and out of her mouth, his back arching as he began to leak out his sticky precum. His cock throbbed and beat harder than ever before as it started to stand fully erect. Mingled with the wet, loving caresses of his mother's tongue lapping all over his cock, smothered with a mixture of her drool and his own lube.

Vinny was now down on all fours, sucking away as she looked up at her moaning son. She almost smiled, wagging her tail slowly as she savored Simon's moans.  

"Hahhh… You're so good, Mom… So goood…" Simon whispered, his legs close to buckling. He was still able to reach down and pat Vinny on the head, a quick gesture for a job well done. She hummed softly from the pats, sending gentle vibrations into his shaft.

Enjoying his words of praise, Vinny held his hips firmly, just enough for him to continue moving as she bobbed her head along with his steady motion, her drool trickling down his cock and onto his balls, still being cradled ever so carefully in her warm paw. Simon fought to keep his eyes open, hooking his claws into the blanket as he kept an eye on his mother. "Hnnh… A-A little harder, mom. Please." He spoke.

"Mmhm!" Vinny playfully flashed him a thumbs up with her free paw, then grasped at his chest fur with it as she slowed down, now sucking away at his stiff length with gusto, her tongue dancing up and down and around a vein. She pushed herself forward, groaning as she managed to reach his base, her nose buried in his crotch fur.

Simon… had a much cleaner scent than her other boys. They were nowhere near terrible, no, but Simon had an interesting mix of musk and… cherry blossoms? Must've been the soap he'd brought along. Nonetheless, she went to nuzzling into his soft fur, taking in more of his scent as she grabs hold of his tail right at the base, squeezing it and tugging a little. Simon resulting moans rang out in the room, his paw grasping at her head. "G-Gah! It's about to come out!" He warns.

Hearing this, Vinny quickly pulled away from him. A trickle of his precum lingered from her lips. Simon blinked, groaning as his nearing climax began to fade away. "A-are we done?" He asks, looking her in the eyes. "I thought you were going to let me finish…"

Vinny shook her head, flashing him a smile. "Oh I am. Don't you worry about that, Simon." His heart skipped a beat as he watched Vinny sit up on her knees, slowly crawling up to straddle his thighs. "I just really wanted your first time with someone to be very, very special. Now, how do you want me to do this? Usually, it's the guy who's on top, but since you're new at this…"

"Uh… I suppose you can call the shots, Mom," said Simon. He looked down at their crotches, just barely separated now. He bit down on his lip, shuddering as Vinny moved down, his tip pressing into the soft spongy folds of her entrance. 

"Alright, Simon. Wrap your arms around me, okay?" Vinny instructed, arms going around his shoulders for support. "I'll start out slow for you."

With a nod of his head, Simon had grasped her by the ass, arms locked around her hips. "I'm ready…" He said, unable to look away. There she was… A little more wet than he expected, yet intoxicatingly inciting. Something deep inside him told him to make the move first; make her gasp and squeak and moan. He shook his head, remaining in place as she began to lower herself down, her warm, well used walls fitting around him snugly.

"O-Ohhh gosh!" Simon moaned, almost squeaking himself as Vinny took him into her folds completely, their crotches meeting in a mix of his pre and her slick juices. "Mom, it's so hot inside you..." Simon groaned out, his hold on her rear getting tighter as pleasure surged through his whole body. Having her breasts right there in his face only added to his arousal, and Simon took the chance while he could.

Without warning, he had latched himself onto one of her nipples, immediately going to sucking on the little nub. "Mnh! C-Cheeky boy…" Vinny huffed, starting to bounce herself along his length slowly. 

It didn't take long for her milk to start flowing, and it didn't seem to bother Simon. He only moaned louder, gulping down her milk while he played about with her butt cheeks. "I-It has a nice taste to it." He commented, curling his toes against the blanket as he guided her along his dick, wiping his mouth before moving to her other teat to give it the same treatment.

"Gosh, Simon, you must be hungry." Vinny mumbles, holding the back of his head to keep him at her chest while she continued bouncing, tilting her head back as she moans again. "Oh! Cheeky and sneaky…" she huffs softly. Simon had lifted her tail in order to prod at her exposed back entrance, sending shivers up along her spine.

"Nngh… S-Sorry, mom, but I want you to feel this good as well." Simon pants, letting go of her nipple in order to nuzzle in between her breasts. "I couldn't help myself. Plus I t-think I'm getting close again." he added, looking down at their crotches once more. His cock was buried underneath Vinny's straddling hips, the moans coming from her increasing in volume as she bounced harder into her son, picking up the pace. That tingling warmth was unmistakable, rushing through Simon's body as he squirmed a little, trying to work himself into his mother's bouncing.

But, Vinny brought herself to a halt. She simply say in his lap, panting as she looked him in the eyes. "M-Mom, what the- why'd you stop?!" He groaned, bucking his hips up a little. 

"Now now, Simon. What did I tell you?" Vinny asks, cupping his cheek softly. "Your girl would really enjoy a nice kisser. So, please…" she closed her eyes, leaning down enough until their lips were pressed together.

Simon's eyes widened from the contact and he squirmed, almost pulling away until Vinny had grasped the back of his head, keeping him locked in. Mumbling a little, he soon ended up slumping his shoulders, melting into their kiss again. This time when Vinny's tongue met his, he caught hers carefully with his teeth, grasping her body firmly as he managed to lay back with her still on top, wrapping his legs around her waist as he started pounding up into her.

He could taste the sweetness lingering in his mother's soft mouth as their tongues wrapped together, mingled with each other's saliva and warm breaths. Vinny, clearly taken by surprise, gasped lightly before simply letting him keep going, a few moans slipping out as he had his way with her.

This time, Simon had her locked into their kiss, refusing to let her go as his tongue wrestled against hers instinctively, pushing against it and rubbing around. He was nearly lost in a haze of pleasure, lapping along her tongue as he curled his toes, lightly tugging on Vinny's tail. He ended up breaking the kiss soon after, tilting his head back. "M-Mom, I'm gonna cum!" He moaned out, gently hooking his claws into Vinny's rump.

"O-oh yes, Simon… Let it all out, please... I want your seed inside me!"

Simon huffed, letting out a little growl in her ear as he made his last few desperate thrusts. He hid his face between Vinny's breasts again, muffling what would have otherwise been a rather loud moan as he released himself inside of her. 

"O-Oh… oh dear…" Vinny closed her eyes, letting Simon's sticky, wet warmth flow into her, spreading throughout her body as she slowly rolled off of him, now laying at his side.  "Simon, that was... a lot better than I expected~"

Simon rolled his eyes, ignoring her little tease.  "Thanks, Mom… I suppose that you also felt amazing." Simon countered once his afterglow faded away. He sat up in the bed, sighing softly. "I… guess I'll be heading back to my room now." As he prepared to go, however, Vinny grabbed hold of his paw.

"Ah ah ah, young munk." She says. "It's good that you climaxed, but you've got to make sure your partner does too, remember?"

Simon blushed as he watched her run her paws all over her own tummy and rubbing it.  

"I'm s-sorry, mom, but I don't think I can get it hard again after all of that… You really got me going." Simon says softly as he looks down. 

Smiling at him, Vinny moves his paw down. "Lucky for me, you don't always have to be stiff in order to please a girl." She says. "Feel around.  You're a very smart boy, you know what you should be finding, right Simon?"

Nodding his head, Simon gulped as he felt through Vinny's slit.  "Y-Your clitoris, you mean."

Vinny's little gasps and soft moans were a sort of radar for him, leading him closer to that spot. His paw trailed over Vinny's legs, tracing upwards from her thighs to her slit. From the feeling alone, he could tell she was slightly gaping, and quite the mess. 

Not only had he just unloaded in her, but all the time she spent with Alvin and Theodore was evident.  

It didn't take him too long after to find that bud, his thumb brushing over it once. The way Vinny nearly squealed after that almost made Simon yank his paw away. She clamped her thighs around his paw, though, keeping it there.

"Oh, goodness, yes keep touching it!" Vinny moaned, grasping her breasts as she wriggled in place a little, grinding herself against his paw. Simon's cheeks burned bright with his blush, the way their mix of fluids was coating his paw just felt so strange, and yet so... right. He pushed two of his fingers inside her, wiggling them about while he continued rubbing his thumb on her clit.  "Wow mom… you're really wet now." 

Vinny tensed up, closing her eyes tightly as she suddenly reached her own peak, her hold on Simon getting even tighter as her warm juices gushed out against his soft paw, dousing his fingers in the sticky stuff.  She fell back onto the bed, panting away as she placed both paws on her belly.

Simon, after cleaning his paw, laid down at her side, gently resting his head on her chest. "Thanks, Mom… Tonight was fun." He tells her. "I just... part of me wishes that it didn't have to end…"

Vinny reached a paw up, cupping his cheek as best as she could. "Shhh… just… just get some sleep, sweetie… I'll see you in the morning."