Jack was annoyed.
He didn't need a pup sitter! He wasn't, as far as he was concerned, a pup any more! He was a teenager now! 13! He liked girls and action movies, and listened to rock music! Not the cubish cartoons and whatever his parents put on!

So he was sulking in his room when his parents called up his pup-sitter was here.
They were going to spend the weekend away for some "together time"
So they had hired some crusty old lady who wouldn't let him play his games because they were "so violent, so nasty and upsetting" or watch movies and stay up late even though it was a school holiday.
His parents let him be alone when they went out for a day! Why couldn't he do two or three days! He could look after himself for two nights! He knew the number of the pizza place, he knew what to do in case of a fire and not to open the door to strangers.
So he'd have to spend what by right should have been fantastic free time with some gross old lady who would treat him like a cub again.
It wasn't fair!

There was a soft knock on the door.

"What?" He snipped at the interloper, he was busy sulking in his room, looking at one of his books about a video game.
The consoles were still in the living room because that's where the TV was, his parents had offered him a TV in his room but it would have been tiny and come with lots of strings attached. He liked the big TV.

"Hey, Jack? I'm your sitter for the next few days" the voice though the door didn't sound like a crusty old woman. It sounded young.
Great. He'd gotten one of those weird highschool girls who were ugly and wanted to talk all the time to their friends and baby him. They were just younger versions of the old ladies but worse somehow, he could play console but they were super strict on bedtime and chores because they wanted approval so they could get more money.
The old ladies just had nothing else to do as they waited for the angels to finally collect them.

"May I come in?"

"Whatever"

And in stepped an angel.

She wasn't some high schooler, or maybe a senior, she looked like a college student, and her loose hoodie had a college logo on.
She was in a tight set of "mom" jeans which showed off her toned curves and a loose "baby doll" shirt which showed just a bit of her flat tummy but dangled over her ample boobs.

He was immediately suspicious.
He had heard from some of their other cubs, pups, boys, guys! Guys at school who had had sitters from colleges.
Most were lax on food, but either they would ignore you and just be busy with school work, so you could get away with anything, as long as you weren't loud, which meant generally no or little games.
Or worse they'd invite their boyfriend or something over and spend the whole time "hanging out" in the living room, which again ment no games and often early bedtimes because they wanted to make out or whatever.

"Hay buddy, I saw you have the new PlayCube 4 AND xStationX with Call Of Battlefield Honour 17... I'm kinda jealous if honest... Mind if I play? Do you have a guest account I can use?"

"Sure, whatever." This was definitely a trick.
The labrador/collie cross could tell. She wanted to be his "friend" and "hang out".
Yeah.
Right.

After a few minutes he heard the rattle of gunfire and crump of explosions from downstairs.
Great she was probably messing up his save now so he'd come down and play games so she could ignore him until bedtime.
He did want to play games but not because she wanted him to.
But he had to protect his save game.

Sulking downstairs he found her cross legged on the couch blowing away hoards of Northern Alien Soviet Terrorist Yaks.
He watched from between the bannisters.
She was good.
Beginners' luck, must be.
She was probably on super-n00b-storytime-easy mode.

The level complete screen came up and the crashing of swords, guns, shields, helmets and skulls which represented the difficulty came up.
The whole logo of the game, representing über-madman-extreme-hardcore-eliete difficulty was shown.

"Yes!" She fist pumped to herself. Fine maybe she had a boyfriend who played this with her and he was going to come over and hog the console.
He huffed to himself as the next mission cutscene played.

"Jack? Hey! Sorry I couldn't work out which was the guest account so I signed in with my own. Hope that's ok?" She closed out the game bringing up the console's home screen and her avatar.
He boggled as he saw her achievement score.
Her avatar was a model of her, no special adornments or anything.

He padded down the rest of the stairs, eyes locked on the screen in awe.

"That can't be your account!" He blurted out.
It wasn't fair! She was a girl! She was at college! She was pretty! She couldn't have a score like that!

"Oh? Why not?" She simply cocked her head.

"Because, because, because you're a girl! And pretty and, and at college and it's not fair!" He burst out. Some distant part of him was disappointed with himself for being so cubish and having a tantrum like this.

"Wow. Okay. Well, I guess what I was told was wrong, that you were a nice and mature young man. Guess these must be your dad's then." She motioned at the shelf of games, consoles and movies.
"Guess your parents would want me to actually do the whole bedtime and stuff thing too. Shame, you have some good games and movies here. Would have been fun to play split screen or whatever."

"What? No! Those are mine!" He raced over and stood defensively in front of the entertainment unit.

"Yeah. Because your folks seem like the kind of people who would give such an immature little cub this..."

"Hay! I'm a big boy! I'm 13! I'm not some little cub!"

"Then prove it."

"How?!"

She shrugged.

"Stop shouting at me perhaps? You're having a tantrum from where I'm sitting. I'm not above giving you a smacked bottom if you insist on being naughty."

He jaw fell open

"You can't do that! You, I'd ... I'd tell my parents!"

"Saved you the trouble little man" she held her phone out showing a text conversation.

/We don't tend to smack him. Only once or twice when he was really little. Thanks for asking, I know your won't want to, but you can if he's being a real shit/

"Also, not staring at my tits would be nice... I get a lot of boys do, but, you want to be all grown up, stop looking at my tits like a pup needing a feed."

"bwu?!" He couldn't form an articulate sound. What on earth was going on?! Ok maybe he had been staring at her boobs but... They were right there and so... Big and... Big ... Good looking... Boobies.

"How about this. You beat me, best of three, on any of those games, I'll believe you. I'll believe you're what your parents say you are and what you claim to be and we move on." She stood up, chest bouncing slightly, hips swaying in those tight trousers. He could just about see the outline of her panties through those jeans!

"Ok...wait, what if I lose? I won't but..." He narrowed his eyes at this. He couldn't work out what her deal was. What was she doing? What game was she playing?
He'd never heard of a sitter doing this before.

"If you're so certain you'll win and this isn't my account then you have nothing to worry about." She held out her hand, they shook.

He studied the collection closely before settling on Rising Dead IV. It was only a couple of months old, it was his dad's but he still played it, and was good at it. He'd completed it on Hard and was working though on Ultimate.
If she was bluffing she'd be put off the first time he used his chainsaw machine gun to slice her into chunks amid a horde of undead in a theme park.

"Rising Dead IV, Hard Mode, 1v1 deathmatch." He announced, holding the game box up.

"Sure. I'm ok to use this controller still?" She held it out as he slipped the disk in.

"Sure. Whatever." He dropped onto the couch next to her. He didn't notice the series of notifications in the news feed telling him of DLC and unlocks as he set up the match. He forgot that this was her account. Not his.

"Best of three remember."

"Yeah, just don't be surprised by this game. It can be kinda bloody. It's a zombie game."

"Ok. Round one."

It took a few minutes for them to kit up and find each other on the large map.
Or, more accurately, for her to find him.
The kill screen expanded, to cover the full size of the large TV.
In graphic slow-mo it showed a view down the scope of her pipe rifle, him neatly in the cross hair, then the bullet travelling from the barrel, out over the concourse of the theme park, and into his character's skull, down and through the chest cavity. Organs exploded and bones shattered.

"That's one zero to me."

"Lucky shot! Get close to me, anyone can camp with the pipe rifle!"

They started the next round.
After a short engagement in melee the kill screen came up.
Again in graphic slow mo it ran.
Her character, using a sledgehammer, knocked his down before swinging it execution style, an x-ray view showing the solid head slam onto his characters, skull detonating and brain turning to liquid.

"That's two zero. It was best of three. Sorry bud, you lose. Believe me now?"

"I... No! One more! On..." He frantically scanned the shelf "Horizon Speed Racing 4!"
He held the box up

"Okay. But, I've still won. Best of three. If you want to just keep playing games we can do that, no competition or whatever" She was utterly calm.
Completely placid.
She was infuriating.
Why did she have to be so nice!
Why couldn't she be like any of the others!

He was getting mad at that he was getting mad. It wasn't fair! Why did she have to be nice and hot!
He was all ready for her to be the normal crusty old lady or bitchy highschooler but...
She was fun, and nice.

"Gaah!" He dropped the controller and stomped to his room again to enjoy a nice sulk. Fucking stupid nice lady being all good at games.

"I'll let you know when I order dinner!" She called after him, returning to the slaughter of the game in solo mode.

He sat and read his comics as he started to calm down.
She was right, he was being cubish.
But... He still felt ... It wasn't fair.

She was better at him than games.

More time passed.

A soft knock at the door.

"Jack? Buddy? You ok?"

She slowly opened the door.

"Hay, sorry we got off on the wrong foot earlier. I wasn't exactly expecting you to be... Well, such a brat earlier. Your folks said you're a great guy and love your games and consoles. So, yeah, sorry. It's my first time doing this whole cub sitting thing. I'm Sidony, most people call me Sid. So, yeah. Sorry about that. I don't want to be a hard ass on you."

"It's ok." He turned so he was sitting with his legs off the bed, tail curled around him. "I shouldn't've been so mean to you. I was... I dunno, I didn't want a sitter as they're always awful or weird. So... I was mad about ... That and stuff..."

He shrugged, self-consciously. He was upset at how he had behaved.
He'd tried to tell her he was a big kid, but had behaved like a stupid little cub.
She sat down next to him on the bed and wrapped an arm around him, cradling his head against her wonderfully soft breasts.
He couldn't help but muzzle onto them.

He suddenly realised that her hand was on his thigh, stroking gently, as if reassuring.

"It's ok pup. We all have hard days..."

Being a young teenage dog his hormones and body sometimes did things to his body he was still getting used to and was very much embarrassed by.
She giggled softly.

"It seems you're having a hard one now... Don't worry, maybe you are just a little puppy, why else would you get all upset? Clearly you needed feeding..." she moved slightly and pulled her t-shirt up.
She didn't have a bra on underneath.
He stared at the gorgeous boobs before him.
So big, firm yet supple.
Those nipples!
He'd never seen boobs before.
Well, he had, but not since he'd started paying attention to them in this way.
He licked his lips, tail flicking behind him.

"Aww, I think maybe puppy was hungry huh? Well that's ok. Lets take care of that" she was using a soft, almost babying voice, he wanted to complain but she had his head gently cradled against one of those wonderfully succulent nipples.
He knew what to do.
He opened his mouth and took the firm nub of the elder canine's nipple in.
He hardly paid attention to the husky girls fur patterns, how the white of her chest and stomach flowed over her body.
Just that wonderful nipple, and after a couple of seconds, the tasty bitch milk she produced.
He shifted to get more comfortable.

"Ooop, here we go, let's get you comfortable little guy" she scooted back onto his bed, shoving one of his pillows behind her back against the wall, the other to the side.
Gently she guided him over her knees, tugging his shirt off to cradle his head against her breast.

"Mmm, good boooy, drink up, enjoy my nice big milky breasts. They'd so heavy and full. Now, let me help you out with your little problem."
She undid the fly on his shorts and pulled them down, revealing his light blue Y fronts.
Normally he'd have been embarrassed for wearing such cubish underwear, but he didn't. His entire world was teat in his muzzle and the hand trailing over his hard cock.

"Hehe. Y fronts, and you said you're a big boy... Let's get these out the way, we don't want to make a mess do we?" She deftly pulled the front of his underwear down, letting his little puppy cock stand free.

He gasped softly into her breast as the first person to touch him slowly closed her paw around his shaft.

"Mmm, good boy, keep drinking, we can change breasts in a moment. Such a good little puppy, so small and adorable." She adjusted herself and his head, he looked down to see her hand.
Her pinky finger rested against his crotch. His cock didn't even stick out the top of it, even with his little knot out of his sheath.

"Not even a single strand of pubic fur. Just a cute little puppy patch... Such an adorable little thing..." she cooed, he watched as she slid her hand up and down his shaft.

He'd masturbated once or twice, but sex and such was still something new to him. He had only just had biology about reproduction a couple of weeks ago.

"Mmm, good boy, keep drinking" she bounced one of her wonderful boobs before him.
Obediently he latched back on.
His mind was empty, just delicious bitch milk in his muzzle, slowly filling his tummy, and a hand stroking his little cock.
His tail wagged slightly.

Above him the older canine was cooing and encouraging on her little puppy.
Such a good little pup.
Drinking all of mamas milk as she played with him.

Soon her breast started to run dry.
But it was ok.
The other still had plenty.
With a quick reposition he was sucking on the older canine's other breast.

"Mmm, can my little puppy make squirty for mommy or are you still dry?" She was still using her cub voice, but it was so hot to hear right now.

"I...I can make squirty, I can make squirty for mommy..." He panted

With a big grin she looked down at him and met his eyes.
He got lost in her beautiful blue eyes.

"Then do it puppy. Squirt for mommy. Nice big boy sqirties for mommy. If you do you'll get a special reward... Come on puppy. Squirt for me. Squirt for mommy!" She encouraged.
Her paw moving faster and faster.
His tail beat against the bed.

"Gonna... Squirt for... Mooommmmmyyyy!" He squealed as his second ever orgasm, and first by someone else crashed over him.
His tiny coin purse ball sack drew up, underdeveloped balls trying to provide what they couldn't.
A thin dribble of clear boy cum drooled pathetically out of his little pointed puppy cock.
He sagged, panting hard.

"Did... Did I do good mommy? Make squirty?"'

"Mmm, you did very good puppy, but you didn't make squirty for me. I don't think you can, such small puppy balls you have...maybe you're just too young of a cub...but it's ok. Mommy is proud of you. You'll still get a reward, just not this one..."
He felt full and drowsy.
Happy in a post feed and orgasm bliss.

Looking up into her eyes it seemed as if they shone, or glowed slightly... A slight prickle seemed to cross his fur...

"Mmm, gooooood boooooy. Such a good little puppy. Sleep well puppy, nice and full tummy of mommy's milk. So happy and sleepy. All tired from being a good boy for mommy." She picked him up with remarkable ease. She slid his shorts and pants off the rest of the way.
Replacing them with his PJs.

He fell asleep to her gentle coos and praise.