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The Hundred Acre Wood was a marvelous place to grow up. But being stuffed with fluff can make growing up more awkward than one would think. When you have to be 'let out' to get bigger, sometimes changes can make a big difference. Luckily Roo had one of the most caring mothers in all of the Wood. She never fussed about helping her son and, despite not being the cleverest of all the residents there, she was ever in an abundance of love.

As it happened, yesterday was Roo's birthday, a day that he celebrated with all his friends. It marked the day when, like Pooh, and Piglet, and all of the others, he had finally grown up. Excitement ruled the party as he was given gifts and sung to and played games with, knowing that it was the last party he would have as a child. It had been a wonderful day and, like every birthday, that night his mother had let out his seams so that he could grow. She had kissed him goodnight and told him how much she loved him, and he drifted off into dreams of what wonder the future would hold.

But today he excitedly bounced along, tailing his best friend throughout his whole life, Tigger. Today was especially challenging because Roo was still getting used to his new size. Time was when he fit comfortably into his mother's pouch with room to spare. He had been as small as Piglet back then! But today he was nearly the same height as Tigger and that took some adjustment.

"Come on Roo! Hooohohohooo!" Tigger called, "Don't be a slowpoke. I found an excellent tree that I'll bet you could bounce right over with me!"

"Coming Tigger!" Roo shouted with a laugh, surprised at how deep his voice had gotten since the previous night, "Don't worry, I'm right on your tail!"

"Better hurry Buddy-boy, or else I'll have to bounce that tree all by myself! Maybe twice or thrice or even four times!"

"Hah, like I'd let you bounce that tree before me!" Roo boasted playfully, bounding after his friend with all the power behind him he could muster. Suddenly he was airborne, but flying faster and farther than he had meant to. Luckily his path was clear ahead of him, so instead of panic, he worked on sticking the landing. Thanks to his wide feet he landed gently enough, just ahead of his orange friend.

"Wooohoo! That was quite a bounce there Roo! But see if ya can out-bounce THIS!"

Soon a game of leap-frog was underway, sending Roo and Tigger hurtling through the air trying to playfully out-do each other. With his worries out of the way, the awkwardness became a non-issue and Roo soon caught on thanks to his love of bouncing. They bounded all around the wood for hours before they became even mildly tired. Every tree and tall rock was a challenge, something to be leapt over with little care or worry.

But eventually they did get tired, collapsing against a large tree. Both laughed and talked, mostly reminiscing, but soon the conversation turned toward the future. Being stuffed with fluff, Roo didn't generally have much depth to his words, but since his best friend was rubber and springs, it really didn't matter. They could still talk for quite some time about very little.

"Tigger? What do you think of girls?" Roo asked, suddenly shifting the subject.

Tigger was caught quite off-guard, the question coming seemingly from nowhere.

"Wh-what do you mean buddy boy? As far as I know, girls are just fine."

"I mean... what do you think about them? Like... do you want to be with them and stuff? Do you wish you had a girl tigger you could be with and be happy together?"

Tigger drooped, suddenly hit by a wave of regret. For quite a long time he had always considered Roo his best friend, the one person who didn't make him feel so all alone. The cruel fact being that Tigger was, quite literally, the only Tigger around. He would always say that it was the wonderful thing about Tiggers that he was so unique, and heavens knew Rabbit agreed, but sometimes when he was away from the others in the Hundred Acre Wood, he could get to feeling very lonely indeed. But in his heart of hearts, he had always wished fondly that perhaps Roo would grow up and want to be his 'other Tigger'. But now he was asking about 'girls' which told Tigger that such a dream would never come true.

"Listen, buddy boy," Tigger said a little sadly, though he bucked up specifically because he cared so deeply for Roo's happiness, "I really don't know about girls. And... well... you know that we Tiggers are... well... that I'm..."

"That you're the only one." Roo said with a reminiscent nod, "But... well I haven't known many girls in my life. Really it's been so few that I can count them on my fingers! I want... I wish I could know what a girl was like... and maybe find one that was just like me."

"I... I know the feeling," Tigger sighed softly, but then picked up his voice, "You should ask your mother, Kanga. I'm sure she knows all about them."

"What would my mom know about girls?" Roo said with a laugh. A laugh that Tigger shared heartily, but for a bit of a different reason.

"You'd probably be surprised what moms know."

Kanga sighed as she hung a shirt upon the wash line. It was a tiny blue thing barely wider than her hands. The years had seen many a shirt come and go, but she had saved every single one. As she did every year, she washed and hung up all of Roo's old shirts in a row, not only to keep them clean but to also see just how her boy had grown. Now the line of shirts had reached a point where they were big enough for her to wear!

A happy smile hid her desire for days passed when she could hold her baby Roo in her arms or slip him into her pouch again. More than this, she wished she had someone else who she could care for like that. She wished she could have another 'little Roo'. Another shirt, another sigh, and another pang of longing for those times before Roo was born. Those carefree times that, incidentally, had ended right about the time the baby Roo showed up.

And as she finished hanging each shirt upon the line, she heard the sound of bouncing and laughing in the distance. For so long, Roo and Tigger had made it a point to go out on tour of the Hundred Acre Wood every so often, and especially on special occasions. She often fantasized how good a father that Tigger might have been, but unfortunately she also understood that such a thing could never happen. Beyond the obvious, Tigger was simply just too much the free spirit to settle down and teach as a father would. He was a much more acceptable playmate for her son, and deep down she wouldn't have it any other way.

"Did you have fun dear?" she asked as she greeted the boy's return, "Bounce over anything new?"

"Tallest trees in the Wood mom," Roo announced with a proud smile, "No problem."

"Oh I'm so glad you're safe and happy," she replied with a smile and a hug, "And thank you for taking him out Tigger dear."

"No problem Kanga ma'am. He's the best bouncer in the Wood these days!" Tigger exclaimed, turning to leave.

"Naaah," said Roo modestly, "I'm still not better than you!"

"A tie then! The two best bouncers in the Hundred Acre Woods!"

And with a hop, skip, and a bounce, Tigger made his way off into the Woods.

"Mom..." Roo began as his best friend vanished from sight, "I... I wanted to ask you about... um... girls."

It was a bit later that Roo and Kanga had made their way inside. Kanga had decided that this talk needed to be had over a cup of tea and a light snack, especially since her boy had been away all day exerting himself. With steaming mugs in front of them, she prepared herself for the encounter she knew would happen someday. She had simply not expected it to be today.

"All right Roo dear," she said at last, completely comfortable, "What do you want to know?"

"Well..." he started, uncertain of himself, "I wanna know what they're like... I feel like... I dunno, like I want to be with one... but I don't even really know any... I mean there's Kessie, but she only visits sometimes and..."

Kanga laughed lightly, "I used to be a girl too you know," she added gently, amused at her son's naivety. She couldn't help but widen her smile at the face of confusion that Roo now had. "Girls grow up to be moms, didn't you know?"

"N-no?" Roo replied, "How... how does that happen?"

"It's when a girl and a boy become a mom and dad," Kanga answered. She searched her mind for more answers... for explanations... but nothing came readily to her. She knew what he would ask next, but the way to tell him.

"How did my dad... make you a mom?" Roo wondered aloud.

"Well... he um..." Kanga fumbled, able to remember that wonderful night, but completely uncertain how to properly put it into words, "Well... would you like me to show you?"

Before he knew it, Kanga had lead Roo into her room. He looked around nervously, unsure where such a feeling had come from. He had known what his mother's room looked like for years, but this time it was... different. This time, he wasn't in here to play or to help her with chores. This time he was here to learn how to treat a girl.

Without any prompting, Kanga laid herself down upon her bed and beckoned Roo near.

"A girl likes to be touched... but only when she wants to be." She started, motioning for Roo to lay his hands upon her. Surprisingly, Roo did willingly, quickly turning the simple touching into a more playful rubbing.

"Yes, that's it my dear," she said happily, "like a massage. But... there are more places to a girl than her shoulders and back."

With no resistance, she took hold of Roo's hands and guided them to a more sensitive place.

"A girl's pouch is very good to touch, but only if she's ready for it," she explained, "Inside there are other places that feel really good too"

"But, isn't that where little ones stay?" Roo asked confused, "I mean, I spent years in there."

"And I loved having you there. You don't think mommies would keep their babies there if it felt bad, do you?"

"Well, I guess not," Roo said happily as he slipped both hands into his mother's pouch and explored the warm, close space he found there. It was very inviting to him, something extremely attractive about the place.

"Those... oooh... those bumps on the back, near my tummy?" Kanga gasped at the attention her neglected pouch was now receiving, "Yes, oh YES Roo! Right there... play there for a while."

Happy that he was making his mom feel good and learning about girls in the bargain, Roo was excited to play inside his mother's pouch. Still, doing so stirred many a confusing feeling within him. Without noticing, something more had changed in him. He began to feel... charged... and more than just happy to be doing what he was doing.

On the other hand, his mother could see just what was happening, but she decided to leave things alone for now. Her son would learn only as fast as he wanted to learn, and not as fast as she wanted to teach. Of course, soon her son grew bold. For no reason at all, Roo leaned down and kissed his mother on the tummy.

"What was that for?" Kanga giggled delightedly.

"I... I think I want to try something... Can I?" Roo asked hesitantly.

"Well, alright, I suppose," Kanga affirming, wondering what it might be that her son had thought of.

She let out a cry of surprise as Roo bent down and unceremoniously slipped his head inside his mother's pouch! He stayed in only a few moments, relishing the familiar and yet different sensation of being in that pouch again. All the while Kanga writhed in delight, both at the feeling of someone touching her again, but also as her pouch being stretched out by something the size of a baby again. Feeling the motion as well as a little claustrophobic, Roo pulled his head from his mother's pouch.

"Was that alright ma?" Roo asked, a tad worried.

"Ooh yes dear, but... well... with a lot of girls, that might be too much all at once. You have to go slow with girls or you'll end up making them uncomfortable."

Suitably chastised, but no less excited, Roo struck a bashful pose. It was then that he noticed the certain special something sticking out from his waist.

"M... mom?" he said looking down at it, "What... what's happening to me?"

Kanga sat up and almost burst out laughing at her son's predicament. A modestly long tube of bright pink peeked up from its normal hiding place, a sure sign of her boys arousal at the things his mother was letting him do to her.

"Don't worry dear," she said reassuringly, "That's perfectly normal. It's... it's just something that happens to boys when they want to have more fun with girls."

"Well... what do I do with it?" he said with just a little worry.

"Sit up here beside me and I'll show you a few things," Kanga said smoothly, "Though not every girl will let you do all of this to her. I think it's important that you know so that if you meet a girl you can do the right things."

Roo sat upon the bed next to his mother, stiff and nervous for what she might do to this mysterious new piece he had grown. Surprise beyond explaining came over him as his mother leaned down and slurped up his stiff-part all at once! The shock sent his back rigid as he tried to understand just what was happening, but quickly he realize that this thing his mother was doing to him felt very good indeed! Her mouth was warm and moist, slipping over him like a glove. A staggered breath escaped from deep inside him as Kanga moved up and down, seemingly massaging him with her mouth.

For Kanga's part, she relished the taste and feel of her son's plump member in her mouth. Not just because she was happy to be the one to introduce him into this sort of thing, but that she had a good stiff one in her mouth at all. It had been such a long time since she have worked to please a male, and if there was one thing she had always felt good about, it was being able to make others happy. She bobbed her head as fluidly as her neck could manage, sliding her tongue over him and humming her favorite tune as she did.

Roo was in heaven! Everything felt amazing! So amazing, in fact, that he soon felt like he was losing control. He took hold of his mother's head as all he could do was squint his eyes shut and try to hold on to something. Suddenly, it felt like he had enough. Something happened with his new thing, something like squeezing... no... pulsing. Not very long after he felt this completely wonderful feeling did his mom pull her face away.

She was all smiles, satisfied that her boy had a pleasing experience. She knew she wanted more but so too did she know that he would need time to recover.

"Now, I'm going to show you how to make a girl feel good like that." She told him, "I'm sure you want any girl you play with to feel as good as you just did right?"

"Ohh... oh yeah mom," Roo confirmed, almost dreamily.

"Well then, crawl down between my legs and let me show you something."

Roo did as he was told as Kanga laid back down, and as he looked between her legs like he was told. There he saw Kanga's bright pink slit, the same color as his now flaccid pink-thing. As Kanga pulled her legs further apart, the slit seemed to open. Curiously, Roo reached out and pulled the two sides of the slit apart to reveal a hole that he never imagined would be there on his mother.

"Do all girls have one like this?" he asked, mystified.

"Why yes, Roo, that's the part that makes us girls," Kanga explained with a light giggle in her voice, "and boys have... like what you have."

"Wow... even Pooh and Tigger and Piglet?" Roo wondered aloud.

"Now to make a girl happy in this place," Kanga explained, moving him away from such topics, "All you need to do is either lick there until she's done... or..."

"Or what momma?" Roo asked innocently.

"Or you can put something in to there." She finished.

"Like... my fingers?" Roo inquired.

"If you want, but..."

"Like... my pink-thing?"

"Yes my dear. When it gets full like that again, you could put it in there... They were made for it after all."

"They were?"

He said with wonder before prodding the hole with his fingers. Kanga gave a gasp of delight and, when Roo looked up to see if anything had gone wrong, encouraged him to play further, telling him that everything was alright. Now full of curiosity, Roo crawled right up to his mother's fabric vagina. He prodded and poked, enjoying the warmth and feel of her slippery hole around his fingers. He licked, tentatively at first, and then more when he found that it made his mother cry out with happy sounds. He tried to see how many fingers he could get into the hole... three at his best... and experimented to see if she could tell whether she liked his tongue or his fingers on the outside.

Finally he felt that his thing had recovered, feeling stiff and full again just like it had when all this started. In an instant he leaped up, proudly showing off his reinvigorated stiffy to his blissful-faced mother.

"Look momma, look!" he cried, "it's ready again! Can I? Can I put it in you now?"

Kanga smiled at her son's enthusiasm. She could practically feel herself dripping hungrily for that sleek, pink member to be within her.

"Yes my dear, now you can put it in me." She confirmed.

Wasting no time, and filled with excitement and energy, Roo slipped back down and prepared to insert himself into a girl, his mother, for the first time. A lot of fumbling had him poking all around, not fully able to get inside his mom. Gently she encouraged him and leant a hand to help guide him, and soon enough she sighed, smiling, as his tool sank within the slick and wonderful walls. For a moment he was content to just hold himself inside, a vague sense of triumph filling him as he realized what he had been missing for so long.

Experimentally, he pulled himself back a bit before pushing in again.

"That's it Roo, back and forth, and go as fast as you like."

"And... it feels good for the girl too?" he asked, increasing his pace as much as he dared.

"OOooooOOooooh Yes my dear," Kanga confirmed, "Do that all you like!"

And so Roo pushed on, slipping his new pink thing in and out. Somehow, he liked this a whole lot more than the moth thing, but he figured that his mom needed to show him how to do it right before he went on to the better things. Despite having felt the 'great feeling' once already, he found that working back and forth as fast as he could made it happen again. This time, he felt, it was an ever better one than the first and his young heart felt eager for more.

As he sat next to his mother while she cleaned him and her, he wondered for the future. He wondered what new experiences he would learn and if he could get really good at making girls feel good.