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“Mike! Come say hi to the babysitter!”
Mike pretends he can’t hear his mom and keeps playing his video game. He doesn’t know why he even needs a babysitter. He turned seven just last week, that should be old enough to stay home on his own!
“Mike!” his mom yells again. “If you don’t come right now, I’m taking away your computer privileges!”
Mike groans and types gtg into the chat before logging off. He hates that his mom knows enough about computers to lock him out of his account.
“Mike!”
“I’m coming!” he yells back. God, she can’t even wait two seconds! He storms downstairs, wondering what kind of person the new babysitter is. Hopefully she’s a teenager; they usually let Mike get away with more, unlike the old ladies.
His wishes are granted when he turns the corner and sees the girl at the door. She looks about sixteen, though it's hard to make out much of her features through her baggy hoody and sweats. She doesn’t look like the kind of person who likes yelling at kids, at least, but looks can be deceiving, so Mike approaches her warily.
Her bored expression morphs into a smile when she sees Mike. “Hi Mike, I’m Diana, your new babysitter.” She holds out her hand for fist bump, which Mike reluctantly accepts after a piercing glare from his mom.
“Hi,” he mumbles.
“You have our contact information if anything goes wrong,” his mom says to Diana. “Other than that, we’ll be back early tomorrow morning. Have a good night!”
Diana waves bye as Mike’s mom runs to the car, where his dad is already waiting with an impatient look on his face. As soon as they drive off, Diana closes the door and turns to Mike. “Can you keep a secret?” she asks.
“Yes!” Whenever a babysitter asks that, it usually means they’re going to let him do something his parents wouldn’t allow. “I keep loads of secrets!”
“Like what?”
“Like one time, my friend Peter showed me—” Mike cuts himself off. “Hey, you tried to trick me!”
Diana laughs. “Just checking. You passed the test!”
“See! I told you I’m good at keeping secrets!”
“Well, I’ll trust you with this one then.” Diana acts like she’s looking around to see if anyone’s watching before leaning down to whisper in Mike’s ear. “It’s more like a deal, really. If you promise to keep something a secret from your parents, I’ll let you have whatever you want for dinner tonight.”
Mike’s eyes go wide. “Even ice cream?”
Diana chuckles, and for some reason her breath on Mike’s ear sends a shiver down his spine. “Sure, even ice cream.”
“Okay, I promise, I promise!” Mike is practically bouncing with excitement. “What do I have to keep secret?”
“Well first,” Diana says, straightening up, “you have to keep the whole ice cream for dinner thing a secret.”
Mike nods. “What else?”
“I’m going to change into something more comfortable now, and you can’t tell your parents about that either.”
“Um, okay.” Mike doesn’t get it. Why would his parents care if she wears something more comfortable? Oh well, he doesn’t care as long as he gets ice cream!
“Good boy,” Diana says, ruffling Mike’s hair. Normally, he hates it when people do that, but he doesn’t mind it from Diana.
“What are you going to wear?”
“This,” Diana says as she reaches down to her sweats. Mike’s mouth drops as she starts shimmying out of them.
“What are you doing?!”
Diana laughs. “I told you, I’m getting into something more comfortable.” Her sweats are pooled around her feet now, and she steps daintily out of them. All that’s left on her lower half is a pair of pink lace panties that barely leave anything to the imagination. They cling to her slit, bringing Mike the closest to seeing a girl’s privates that he’s ever been. There’s a funny feeling in his tummy as he stares.
Diana isn’t done yet. Now she’s lifting her hoodie up and over her head. She has a short tank top on underneath, but it gets caught on the hoodie and comes up with it. “Oops!” she says as they both go over her chest, exposing her boobs to a shocked Mike. She takes her time untangling her tank top from the hoodie, and Mike stares at her boobs every second of it. They’re small and perky, and looking at them makes that weird feeling even more intense.
“Sorry about that,” Diana says, lowering her tank top. It doesn’t do much to cover up; it stops well above her belly, and Mike can still clearly see her nipples through the thin material. Diana laughs. “Hopefully my tits didn’t scar you.”
“No! I liked your, um… tits,” Mike says, trying out the new word. With a blush, he adds, “They’re really pretty.”
“Aww, thank you Mike.” Diana ruffles Mike’s hair again. “You’re a sweet kid.” She gets a look on her face like she just had an idea, and she leans down to whisper in his ear again. “By the way, if you want to take some of your clothes off as well, I’m cool with that. We might as well both be comfy, right?”
Mike giggles. “You mean I can wear just my underwear?”
“Yep!” Diana says, straightening up.
“I’ve never done that before. Is it really comfy?”
Diana nods. “Oh yeah. The only thing comfier is going completely naked.”
Mike’s eyes widen. “You’ve done that?!”
“Totally. I’m home alone a lot, and I pretty much never wear anything then.”
Mike can’t help himself from imagining what that must look like. He pictures Diana lounging around at home, lying on the couch without anything on. It’s easy to envision, since he’s already seen her tits and can basically see her girl parts through her panties.
“So?” Diana asks. “Are you going to take off your clothes?”
Mike blushes, hoping that she didn’t somehow know what he’d just been fantasizing about. He can’t bring himself to meet her eyes, and instead he finds himself staring at her nipples poking through her shirt.
“Mike?”
“Sorry!” His eyes snap back up to hers in an instant. “What was the question?”
Diana laughs. “That’s okay. I was asking if you want to take your clothes off too. We can both hang out in our underwear.”
“Yeah! That sounds awesome!”
“Perfect!” Diana reaches her arms out to him. “Lift your arms up. I’ll help you.”
The thought of her helping him get undressed has butterflies flapping around in Mike’s stomach, but he follows her command. She grabs his shirt from the bottom and starts lifting it up. Her knuckles brush his skin the whole way up, and it sends a pleasant shiver down his spine.
As she drops his shirt on the ground next to her, Diana says, “Now, time for your pants.” Before Mike can react, she’s unbuttoning his pants. She pulls them down, and he lifts his feet one at a time to help her get them off.
“All done!” Diana says, clapping her hands together. Her gaze slides across his body from head to toe, then comes back up to linger on his crotch. “I love your underwear, by the way. Spider-man’s my favorite superhero.”
Mike blushes. He forgot he was wearing his Spider-man underwear. He feels a bit childish in them in front of Diana’s lace panties, but he guesses it’s okay since she likes them. He likes the way he feels when she’s looking at them.
Now that they’re both in their underwear, he wonders what they’re going to do next. “Is it time for ice cream now?”
“It sure is!” Diana says. “Just show me where you keep it, and we can get started.”
Mike leads her to the kitchen, enjoying the feel of fresh air on his bare skin as he walks through the house. Diana was right; it’s really nice just wearing underwear. He thinks back to what she said earlier, and wonders if he’ll ever get the chance to see what it feels like being completely naked too.
Mike tries not to start thinking about Diana naked again as he opens the freezer. “We have chocolate, mint, and vanilla.”
“Ooh, mint’s my favorite!” Diana says as she reaches over him to grab it. She leans into him as she does, pressing her body up against him. Her touch makes his heart skip a beat. “What flavor do you want?” she asks.
Mike doesn’t answer for a moment, not wanting her to move away yet. His skin feels hot everywhere she’s touching it. He’s so glad he’s not wearing a shirt. “Um, chocolate,” he finally says when he thinks he’s been quiet too long.
Diana grabs the chocolate ice cream and busies herself serving them both. Mike misses her touch as soon as it’s gone. He sits at the table and watches Diana work. He notices for the first time that her panties are short on the back, leaving part of each butt cheek hanging out. Normally, he’d probably laugh seeing so much of someone’s butt, but right now he thinks it looks nice.
When Diana’s done, she sets the bowl of ice cream down in front of Mike and takes a seat across from him. “Looks yummy!” she declares. “Wanna race to see who finishes first?”
Mike grins at her. “I’m gonna win!” he says as he starts digging in.
“Hey! I didn’t say you could start!” Diana rushes to catch up to him, taking huge spoonfuls of ice cream at a time.
She underestimates Mike, who is a master ice-cream-eater. When he’s done, he looks up to her still working on her last bites. “I win!”
Diana giggles at him and points at his mouth. “Looks like some of it didn’t make it to your stomach.”
Mike laughs and licks his lips. When he gets as much as he can, he grabs a napkin to wipe the rest off. Diana is finished with her serving as well by the time he’s done.
“Oh.” Mike points to Diana’s tank top. “You missed some too.”
Diana looks down at the glob of green ice cream on her shirt. “Shit!” She glances sheepishly at Mike. “Um, I mean, shoot.”
Mike giggles. “It’s okay. I won’t tell anyone.”
“You’re such a good secret-keeper.” Diana turns her attention back to her top, wiping off as much ice cream as she can. There’s still a noticeable green stain left. “Well, that looks gross,” she says. “Do you mind if I take this off? You’ve already seen my tits, after all,” she adds with a wink.
“Yeah, it’s okay,” Mike says, trying to hide how much the thought of seeing them again is making his heart race.
Diana smiles at him. “You’re the best.” With that, she stands up and lifts her tank top off.
Mike’s eyes immediately go to her tits. He can’t explain why he likes looking at them so much. It makes him feel nice and warm, especially in his stomach and crotch.
Actually, it’s starting to get a little uncomfortable down there. He can feel his wiener getting bigger, straining against his underwear. He doesn’t know why it does that, but he hopes it goes back to normal soon.
“I guess you like what you see,” Diana says with a laugh. She’s looking right at his crotch, where his wiener’s lifted up a small tent.
Mike’s embarrassed to have her looking at it and covers it with his hands.
“Hey, it’s okay,” Diana says. “It’s normal for boobs to make a boy’s cock hard.”
“It is?” Mike asks as the word cock echoes in his mind. He likes the sound of it. It seems more grown-up than wiener.
“Sure it is,” Diana says. “I’d almost be offended if you didn’t have a boner right now.”
“Do you know why it does that?”
“I do. We can talk about it more in a bit, but do you want to take off your underwear first? That must be really uncomfortable.”
Mike’s eyes go wide. “You mean get naked in front of you?”
“Yeah, I don’t mind,” Diana says like it’s no big deal. “Like I said, it’s super comfy doing that normally, and probably even more since you’ll get to free your boner.”
“I don’t know,” Mike says, not meeting her eyes. “My parents say I shouldn’t show my wie—I mean, my cock to anyone.”
Diana nods. “That’s good advice in general, but you don’t have to worry about that with me. We’re friends, right?”
“Yeah! You let me eat ice cream for dinner!”
“See? We can trust each other.”
Mike still isn’t too sure about it. Talking about it has made his cock even bigger, so he’d really like to let it out, but he’s embarrassed to in front of Diana.
“How about this?” Diana says. “I’ll get naked first, to show you it’s okay.”
Mike’s brain just about short-circuits. He’d been fantasizing about it earlier, but now she’s offering to let him see for real? “Um, okay. I don’t mind.”
Diana smiles at him. “Good boy. C’mon, let’s do this in your bedroom.”
“Why?”
“Because there’s a lot I want to teach you, and it’ll be easier on a bed.”
Mike wonders what it is she wants to teach him as he leads her upstairs to his room. It must be about boners, but he can’t figure out why a bed would make learning about it easier.
“Here it is,” he says as they both step into his room. He goes and sits on the bed, glad he doesn’t have to walk anymore. There’s no way Diana gets how uncomfortable it is walking with a boner in your underwear. He’d almost wanted to just get it over with and take them off, but he managed to make it.
“Nice room,” Diana says as she looks around. For the first time ever, Mike is happy that his mom had made him clean his room before Diana got there.
When she’s done with that, Diana comes and stands in front of Mike. “Time to get naked!” she announces, and without further ado, she hooks her thumbs in her panties and pulls them down.
Mike can’t take his eyes off from the sight in front of him. So that’s what a girl’s parts look like. He’d had a good idea already from seeing it through her panties, but it was so much cooler getting to see it naked in front of him. Instead of a cock, Diana just has a slit between her legs with some flaps of skin poking out of it. It’s super weird looking, but somehow nice too. Mike’s cock had been starting to go back to its normal size, but now it’s nice and big again.
“So?” Diana asks. “Are you going to take yours off too?”
“Okay!” It must be fine since she’s naked too, Mike thinks. He stands up and pulls his underwear down as well, having to really stretch the elastic to get it over his boner.
“Wow, you’re so hard!” Diana says as she kneels down to get a closer look. “You’re about two inches, I think.”
A pleasant shiver runs through Mike’s body from the feel of Diana’s breath on his cock. It jumps up, almost like it has a mind of its own. Diana giggles at the sight.
It’s so weird having someone else look at it, especially a girl. Weird in a good way though. Mike doesn’t want the feeling in his tummy to ever go away.
Diana reaches forward and pokes the head of his cock. “Boop!” She giggles again as it jumps at her touch.
“Why does it get big like that?” Mike asks.
“That’s because you’re looking at a naked girl.” Diana straightens up and smiles at him. “Cocks get big and hard like that so they can go inside a girl’s pussy,” she says, gesturing between her legs.
So, a girl’s parts are called a pussy? Wait, more importantly, there’s something else that Mike’s having trouble understanding. “You mean it goes in your pee hole?”
Diana laughs, but not a mean one. “Not quite. Here, I’ll show you.” With that, Diana sits on the edge of Mike’s bed and spreads her legs. She reaches forward and holds her pussy lips open so that Mike can see. “The pee hole’s up here,” she says, pointing with her other hand. “That’s too small for anything to fit in though. This is the hole a cock goes in.” She demonstrates by slowly sliding her finger in it up to the knuckle.
“Wow!”
“It’s cool, huh?” Diana takes her finger back out and looks at Mike. “Do you wanna try?”
“Really?!”
“Sure, go ahead.”
She seems like she means it, but Mike still isn’t so sure about this. “Doesn’t it hurt?”
“Nope! It feels really good, actually.” She thinks for a moment before adding, “Well, it can be uncomfortable if it’s dry down there, but you took care of that with your cute little cock.”
“What? What did I do?”
“It’s like how seeing me naked gave you a boner,” Diana explains. “Seeing you naked got me wet. It does that to make it easier for a cock—or a finger—to go in.” She thrusts her finger in and out one more time to demonstrate. Mike notices this time that it’s glistening wet. “So, are you gonna try it or what?”
“Okay!” Mike walks up to the bed and gets level with Diana’s pussy. He looks at her one more time, and at her encouraging nod, he slowly sticks his finger out and puts it in her hole. It’s definitely wet inside, but also surprisingly warm.
Diana moans, and the inside of her pussy clenches Mike’s finger. He’s worried he hurt her, but Diana assuages his fears. “That feels so good, Mike.”
Somehow, it’s making Mike feel good too. His cock is harder than it’s ever been before, and his whole crotch is tingling with barely-contained pleasure. He hopes it feels even half as good for Diana.
“Now start moving it in and out, nice and slow,” Diana tells him between hard breaths.
Mike does as he was told and is rewarded by more moans from Diana.
“Mmm, just like that. You’re really good at this Mike.”
Mike feels himself blush from her praise. “Thanks. This is so cool!”
“Yeah, it is.” Diana smiles at him. “Are you ready to try with your cock instead of your finger?”
“Yes!” Mike removes his finger with an audible squelch.
Diana lies on her back. “Here, get on top of me. It’ll make it easier.”
Mike climbs up on her, his skin feeling like it’s on fire everywhere it touches hers. He positions himself with his stiff cock aimed at her entrance.
“Whenever you’re ready,” Diana says. “Trust me, you’re really gonna like this part.”
Mike nods and then slowly thrusts his hips forward. Diana has to reach down to guide his cock, but pretty soon, the head is swallowed up inside her. Mike gasps at the sensations, a million pinpricks of pleasure all concentrated on the head of his cock. Diana’s even more wet than she’d been before, and he slides his shaft in easily. He doesn’t stop until his balls are touching her.
“Mmm.” Mike’s surprised to hear a small moan come out of his own mouth. Diana’s pussy is gripping his cock tight, and the sensation is echoing all throughout his body.
“Good boy,” Diana says. “Now, just do like you did before. In and out.”
Mike does, and it seems to double the pleasure with each thrust of his cock. There’s a pressure building up inside him, one that feels oddly familiar.
Uh oh. “I think I’m gonna pee!”
Mike’s about to pull out so he doesn’t pee inside Diana when she stops him with a shout. “Don’t! Just keep going. It’s okay.”
Mike isn’t going to argue. He’s thrusting faster now, breathing hard from the exertion. His cock feels amazing, and there’s a tingling in his balls as the skin there pulls tight. The pressure’s about to burst. He doesn’t know what’s going to happen when it does, only that he needs it now.
When it happens, it’s like the whole world disappears and is replaced by blinding pleasure. All he’s aware of anymore is him, Diana, and the absolute ecstasy between his legs. His cock is throbbing, jumping around inside Diana’s pussy.
Just when he thinks it can’t get any better, Diana’s pussy starts throbbing too, tightening its grip on him before releasing ever so slightly only to tighten again. Her moans are practically screams now. The two of them keep going like that, riding the waves of each other’s pleasure, until finally the feeling subsides, and they lie there spent.
Mike doesn’t ever want to leave this position. He’s lying on top of Diana, his cock still inside her, and it seems like all the energy he had just a moment ago has left his body.
“What just happened?” he asks.
“You came. I did too.” Diana smiles down at Mike. “Pretty good, making me do that without even touching my clit.” She sighs contentedly. “There’s nothing better than feeling a little cock dry come inside me.”
Mike doesn’t fully understand, but he’s okay with that. Diana’s going to have a lot more time to teach him if he has anything to say about it. “You’re the best babysitter ever. I’m gonna tell my mom to hire you every time.”
Diana hugs Mike to her and gives him a pinch on the butt. “Sounds like a plan. You and me are going to have lots of fun together.”
With that, Mike closes his eyes and loses himself in the feeling of warmth Diana’s touch brings. Still inside her, he drifts off, glad that he got such an amazing babysitter.