Babysitter Pinkie

>It's a cool summer night when you roll up to Anon's house on your scooter.
>You always look forward to these visits, since you get to spend time with one of your favorite boys in the whole wide world! You had all sorts of fun activities planned out in your head, like playing games, eating homemade cupcakes, and, OOOH OOH, you could watch some movies!
>Those are always fun.
>You knock three times and wait, barely able to contain your excitement.
>The door slowly opens, and you can see a young face peering out from the crack.
>Grinning widely, you wave rapidly, letting confetti drop from your clothes."
>"Hi Anon! I'm Pinkie Pie! And tonight I'm going to be your b--"
>The door closes with a slam.
>"Oh."
>You let your arm drop.
>You hear some scuffling inside and a man's voice loudly says something.
>"Anon, don't be rude to our guest We don't shut doors in people's faces, no matter how much we don't like them."
>The door opens again. Revealing Anon's father, dressed up in a nice suit.
>"I'm sorry about that Pinkie. Anon's a shy boy who doesn't easily take to other people. It's nothing personal."
>You immediately perk up again.
>"Oh, that's ok Mr. Nonymous. Anon and I are going to have a wonderful night here together, don't you worry about a thing!"
>He smiles.
>"I know you will, Pinkie. I can always count on you."
>He turns down to Anon, who is hiding between his legs.
"You be a good boy for Pinkie. I'll be in late at work again, so make sure you get him in bed at the correct time."
>"Sure thing Mr. Nonymous. I won't let you down."
>With that he moves past you on over to his car.
>You step into the house after Anon, who had gone running into the living room, and was now partially hidden behind a large couch pillow, peering out at you.
>You sit down on the couch next to him, smile never wavering.
>"I hope we can have lots of fun while I'm here, Nonny. I hope I can call you that. Nonny. I have all kinds of super fantabulous activities planned for you before I have to get you into bed. Do you like to play any games?"
>He hesitates a moment, before nodding.
>"Well that's just super! Why don't you pick out a game and we can play them together?"
>"Mario Kart? I LOVE that game! Go ahead and pop it in!"
>I know something I'd like to pop him in
>Whoa, Pinkie, where'd that thought come from? Let's keep it G rated, please?
>Grinning, Anon rushes over and pushes the disk into the system and picks up a Wiimote.
>You do the same, making sure to zip the strap to your wrist. Safety first!
>After the title screen comes up he chooses VS. and you both pick your racers. He selects Princess Peach and you choose Mario. After a few moment's time, the race begins.
>You twist and contort your body, trying to stay ahead of the pack.
>Anon seems to know this game rather well, strategically using items and going down partially hidden alternate paths.
>It isn't long before the race ends, with Anon in 1st and you in 5th. He looks immensely happy at this, bobbing up and down.
>You, meanwhile wipe your sweaty brow with the back of your hand.
>"Wow, Nonny, You're really good a this. I guess you play this game a lot, huh?"
>He excitedly nods, smiling all the while.
>"Well all that playing has made me hungry. Why don't we go to the kitchen and see if we can't rustle up something to eat?"
>He nods and jumps off the couch, running into the kitchen.
>Getting up yourself, you follow, a little bit slower.
>Any other babysitter would just bake some pre-breaded chicken nuggets but you were one to go above and beyond the call of duty.
>You pull some pork chops out of the freezer, putting them in the microwave and setting them to defrost. Then, you walk over to the counter top and set up a little breading station, pulling out some flour, cooking oil, a container of rice, salt, pepper, garlic powder, a large pot, and a skillet.
>You pour about two cups of rice into the pot, along with 2 1.2 cups of water, then set the pot on the stove on high to boil.
>You then measure out a couple cups of flour and dump them on a plate, and the cooking oil into the skillet.
>Hearing the microwave go off, you walk over and open the door, drawing the now soft chops out and carry them over to the counter.
>Turning the skillet on, you let it sit a while so the oil can get hot.
>You season the chops, flour them, then drop them into the hot oil with a sizzle.
>After doing this you turn to Anon, who is staring t you with a look of amazement.
>You wink.
>"Betcha didn't think you'd get a babysitter who knew how to cook, huh?"
>He shakes his head.
>"Don't you worry about a thing, ol' Pinkie's gonna take care of ya."
>You finish up by pouring off the excess grease and mixing up your gravy in the skillet.
>The right flour to water to oil ratio is important.
>Don't want it to be too thick or too watery!
>Satisfied at the consistency, you turn the burners off, strain the rice, and fix your and Anon's plates.
>You gaze at Anon intently, gauging his reaction.
>He cuts off a small piece, and slowly chews it with a thoughtful look on his face.
>That look quickly morphs into one of wonderment, and he starts scarfing down his food with abandonment. taking breaks every so often to gulp down some water.
>Seeing this, you beam.
>"Yeah, that's my own special recipe, it's a real hit at home. I just wanted to make sure you're well fed and satisfied."
>He pauses for a moment, nods, then continues eating.
>It isn't long until he's finished, plate licked completely clean.
>*Sniff* there's a boy right after your own heart.
>You clap your hands and loudly exclaim, "Well, now that that's done, let's get you into a bath and changed into your PJs."
>He looks disappointed at this until you add,
"If I get you washed up then we can watch some movies together."
>At this he perks up and jumps out of his seat, running up to his room to get his pajamas.
>You meet Anon in the bathroom. He happily hands over his jammies, which you fold up and lay on a clothes hamper.
>Pulling out the plug you run the water for a bit, putting your hand under the spout to test that the water is warm enough to bathe in.
>Once the water is warm enough you shut off the spout and turn to face Anon.
>"Well, Anon, I trust you know how to operate the tub by yourself. I'll just go ahead and wait outside until you're finished."
>As you try to leave Anon grasps your hand, looking up at you with pleading eyes.
>"Aheheh", you chuckle nervously, "I have to go, silly. I can't just be in here while you're naked."
>You try to loosen your hand from his grip, even lightly tanking it but he refuses to let go.
>You're at a dilemma. On the one hand Anon clearly wanted you to stay, and in a different circumstance you'd be happy to oblige but, you've heard of other babysitters being fired or even arrested for lesser offenses, and you didn't want to take any unnecessary risks while you've got a good thing going.
>You'd hate for Anon to be sad though, and you have a reputation for providing an exemplary service.
>One...
>One time couldn't hurt, could it?
>You try your best to resist the adorable assault of his cuteness but it isn't long until you finally relent.
>You only hope this won't end badly for you
>"Oooook," you say reluctantly, "I'll stay, but I'll have to turn around while you undress and get in the tub, got it?"
>At this he nods, and begins pulling off his shirt.
>You turn and stare at the door, not looking until you hear the splash of him stepping into the tub.
>Once you turn around again you can see Anon sitting in the half filled water, looking at you expectantly.
>Gulping down your fear, you walk over and kneel to easier reach his small body.
>On the edge of the tub you can see several plastic bottles and a loofah, with labels for shampoo, conditioner, and body wash on them.
You reach for the body wash first, squeezing a small amount onto the loofah and submerging it into the water.
>"Lean down a bit, I want to scrub your back first."
>He obediently complies, grasping the lip of the tub and arching his back to give you plenty of surface area to work with.
>You softly rub all over his back, under his armpits, around his neck. and even behind his ears. After this, you instruct him to get on his knees and face down so you reach his butt and the backs of his calves. With all this done you dread what comes next. Now you're going to have clean the front of his body and shampoo his hair. You feel a few beads of sweat forming on your brow, and you don't think that's coming entirely from the heat n the room.
>You've faced down multiple demons and selfish baddies empowered by magic in the past, so why now are you scared of something so small and trivial?
>You doubt Anon would tell if anything untoward happened anyway, the boy adored you.
>Steeling yourself, you tell Anon to rise and turn to face you, so you can clean his chest and abdomen.
>Lifting himself he slowly gets up, letting the water run off his nude body.
>At the crux of his legs you can see it, his little member.
>Initially soft due to the warmth of water the penis goes partially erect in the cool air.
>When you were younger you never really had a chance to see the male anatomy, growing up in a house with three other girls.
>You wonder what your father would say if he saw you now.
>Not wanting to keep Anon waiting out in the cold, you mechanically bend your arm upwards, sudsing the chest and abdomen before moving on to his legs, avoiding the crotch region entirely.
>Finally, after much hesitation, you grip the penis and hold it up, allowing you to reach under his balls and wash in between his thighs.
>His eyes are closed in pleasure while you do this, making you feel slightly dirty.
>With the worst part of it over you breathe a sigh of relief. Now all you have to do is shampoo his hair, You feel like the BOI is going to come any minute and kick down the door, hauling you off for questioning.
>You squeeze the shampoo and conditioner onto the loofah (better to have it done in one go) and thoroughly lather his hair, then push him down in the water to rinse it.
>You repeat this several times, then drain the tub/
>Anon stands up, and you towel him off, then get him fitted into his PJs.
>O-ohkay Nonny, let's go downstairs and watch a movie, shall we?"
>Oblivious to your pain he rushes off excitedly, leaving you to trail behind slowly, thoughtfully.
>When you're sure he's out of sight you stop, squeezing a breast and let the other hand wander down into your panties. You're wet. Why are you wet? You're not some kind of pedo, are you? Fantasies dance in your head as you stand in the hallway, slowly schlicking yourself.
>Maybe... maybe you could try something with Anon, and he's uncomfortable with it you back off and never think of it again?
>Yeah, that would be the moral, ethical thing to do, and if it leads to something more that would just be the frosting to the cake of a successful night of babysitting.
>He is already waiting on the couch when you come into the room, reclining on one of the couch pillows.
>He smiles when he sees you, patting the seat next to him to entice you to sit.
>God, he's just so precious and cute, your heart melts every time you look at him, which makes you feel all the worse when you start feeling aroused.
>You stand there for a short moment, before saying, "Um, why don't you pull out the movie you want to watch?"
>Nodding, he gets up and walks over to a media cabinet.
>Opening it, he runs his hand over the various titles before reaching in and pulling out a DVD, which he then walks over to show you.
>Examining it, you say ,"Hmm, that's a pretty scary movie. Are you sure you want to watch this with me?"
>Nodding in the affirmative, he puts the DVD into the player and presses play.
>He grabs your hand and guides you over to the couch, where you sit with Anon cuddled up close to you.
>You both watch the movie, Anon occasionally
pressing his face into your bosom when a particularly scary part comes up. You tenderly hug him and stroke his head, keeping his fears at bay with your soft body, like a giant human teddy bear.
>When the movie concludes he's clinging to you tightly, face pressed into your breasts as he straddles your body.
>You bite your lip, holding him close to you.
>You hope he can't feel the swampy damp wetness between your legs, or the diamond hardness of your nipples.
>Anon is still hanging on to you as you carry him to his bedroom.
>As you attempt to pry him off of you lay him down in the bed, he clings to you tighter. refusing to relinquish his hold on you.
>You sigh.
>Laying it on thick a little aren't you buddy.
>"Alright ,Anon, look, I can't end the night until I get you into the bed and asleep. It's one of my main Pinkie Rules. What is it going to take for you to let me go and into bed?"
>"Please don't go."
>You look down at him in shock. Those are the first words he's spoken tonight.
>"Please don't leave me. My Daddy always has to stay at work late. I'm scared of being all alone."
>Your heart melts. You can't just leave him here by himself, that would be selfish and cruel.
>You hug him tight to your chest, eyes tearing up a little.
>"I... ok... I'll stay with you for a little while, until you fall asleep, ok? You don't have to worry about a thing. Mama Pinkie will take care of you."
>You pause as that bad part of your mind oozes to the surface, coloring your personality. Anon is at his most vulnerable here. Now might be the time to strike! You resist mightily, but it ends up being no contest as your brain shuts off and your vagina takes over.
>"H-hey Anon..."
>He looks at you questionably.
>"I've got this game we can play, to help you relax. It will feel real good, you'll love it."
>He doesn't hesitate before nodding, of course he want to play a game.
>Smiling a little smile, you gently push him down onto the bed until his head is resting on a pillow.
>You tug at his pajama bottoms, saying "For this game you're going to have to pull down your pants. Don't worry about getting cold, I'm here to make sure you stay nice and toasty."
>Pulling down his pants reveals a pair of white underwear, and the prize that lies beneath. You gently stroke at his covered penis, looking to get it hard enough to effectively work with.
>Anon is completely unaware of how wrong this is, of the risk you're taking.
>"Alright, now I'm pulling off your underwear. I might need you to lift your butt a littl-- theeere you go. That's perfect."
>Peeling off his underwear you can see his little member, pinned underneath the fabric, before it springs free, fully erect.
>Your mouth is drooling a bit, as you take in the majesty of the boy's little cock.
>You gingerly stroke it, up and down, feeling the warm flesh flex underneath your fingers.
>Leaning down you tease the tip with your tongue, licking it like it's a lollipop.
>Then, you gently suck the tip a few times, before engulfing it in your mouth.
>Anon is giving off boyish moans and writhing upon the bed, clawing his fingers into the bed sheets.
>You almost want to see his face, to look him in the eyes as he lets loose.
>You don't want to give him up just yet however, so you continue to gently suck and bob on his boyhood.
>Releasing his member with a POP, you reach back, lifting your skirt to pull down your own panties.
>You are more wet and turned on than you've ever been, and you're going to see this thing through to its conclusion.
>"Now comes the part for the second part of the game, where you get to make Pinkie feel good."
>You get up on the bed and squat over his crotch, slowly lowering your waist until your entrance is just touching the tip.
>You gyrate your hips, letting the penis strum at your lips, before lowering your self and letting him enter you with a happy sigh.
>You fall forward into a sort of crouch, up towards his face, and softly penetrate his lips with your tongue, swirling it around
to achieve maximum pleasure.
>All the while you pump up and down, undulating against his body.
>You know he won't last long.
>You exactly where you want him to spill his seed.
>You speed up, building him up closer and closer to a climax before you tank your tongue out of his mouth and whisper in his ear, "Cum for me"
>His body arches as he sprays his juvenile semen inside you, panting heavily with eyes glazed over.
>You kiss him on the forehead and whisper, "Thank you.", before collapsing onto him, hugging him in your afterglow.