The New Babysitter

By Zyngaru
[email protected]

Copyright 2020 by Zyngaru, all rights reserved

The New Babysitter
by Zyngaru
Email: [email protected]
 
Summary. Fifteen year old Krystal is ready to turn over her babysitting job, watching twelve year old Jackson and eleven year old Jason, to her fifteen year old boyfriend Henry, but there's a small catch first. Henry for sure doesn't see this one coming.
 
 
The New Babysitter
 
Fifteen year old, Henry Jackson, just got his dream job. He’s been wanting to babysit for over a year, but mothers tend to not want a boy to babysit their kids, even when their kids are boys. This week he received a phone call from Mrs. Sanders, who has two boys, twelve year old, Jackson and eleven year old, Jason. Henry’s girlfriend has been babysitting these boys for years. Evidently the boys have been begging their mom to get them a boy babysitter. In their minds they’re too old to be watched by a girl babysitter. According to Mrs. Sanders, when she told Krystal about the boys wanting a boy babysitter, she suggested her boyfriend for the job. That’s how Henry got the call. He’s been so pumped-up all week with anticipation of watching these two boys. Of course in Henry’s mind, the boys being eleven and twelve, are actually old enough to watch themselves, so he’s thinking, that he’ll just be there to hang out and play with the boys.
 
Jackson and Jason love their babysitter. Krystal is the best. It’s just gotten to be embarrassing telling their friends that they still have a babysitter and having a girl babysitter is the worst. It makes for some embarrassing teasing. Having Henry as a babysitter won’t be so bad, because they can tell their friends, he’s just a friend that likes to come over and hang out with them. Krystal has told them all about Henry and the things he likes and dislikes. She has also told them that there’s something special she wants them to do the first time he babysits. Since they owe her for recommending Henry to their mother, they agree to do it. Of course it also sounds like a lot of fun. So both Jackson and Jason are excited with the anticipation of Henry’s first day babysitting them.
 
Krystal loves watching Jackson and Jason. Even as old as they are, they aren’t really shy around her. She gets to see them naked every time she watches them. Neither boy is in puberty yet, although Jackson does show small signs he might be on the cusp of it. He’s become clumsy and knocks things over and even trips over his own feet lately. She isn’t for sure, but there also might be the slightest bit of growth in his wiener. It’s now just a little longer and a little fatter than Jason’s wiener, where they were both exactly the same size just a month ago. She’s also noticed that Jackson turns red when he gets ready for his bath and she sees him naked. So, it’s probably Jackson who’s been pressuring his mother the most, into getting them a boy babysitter. Now Krystal is all for Henry taking over, as long as the boys keep their part of the bargain she made with them. She really likes Henry, but he’s way too shy and reserved. He won’t even go shirtless around her, let alone wear the Speedo she got him for his birthday. Hopefully the boys can loosen Henry up. She wants to see Henry’s skin.
 
Saturday morning, Henry, gets up, and gets dressed in his good jeans without any holes in them and decides to wear an Aquaman tee shirt to impress the boys. After eating, he makes the short two block walk to the Sanders home.
 
Jackson and Jason get up and put on basketball shorts and light tee shirts, because it’s a very hot day. After breakfast they get their laptop and sit in the family room Face Chatting with Krystal.
 
Krystal: “You guys ready for Henry?”
 
Jackson: “Heck ya.”
 
Jason: “We got it all planned out.”
 
Krystal: “I’m going to be able to see everything, right?”
 
Jackson: “Yep. The camera will be going, but you won’t be on the screen. So don’t say anything or he’ll know you’re there.”
 
Krystal: “I’ll keep quiet. Just make sure he puts on a good show. I have two of my friends here and they want to see some fun too.”
 
Jason: “But they’ll see us too!”
 
Krystal: “Now Jason. You’re not getting shy on me are you?”
 
Jason: “No. But I don’t know your friends.”
 
Amy: “Hi Jason. I’m Amy. You’re not scared if I see you are you?”
 
Cassie: “Or me. I’m Cassie and you’re just the cutest boy ever.”
 
Jason: “Well. I guess not.”
 
Krystal: “What about you Jackson. You’re being awfully quiet.”
 
Jackson: “I don’t know. You didn’t say anything about other girls seeing us, it was only supposed to be you.”
 
Amy: “Jackson. I think you’re real cute and I won’t tell any one about what I see. Okay?”
 
Jackson: “Um! I guess.”
 
Jason: “The doorbell just rang. So Henry’s probably here, so you guys have to be quiet now.”
 
Mrs. Sanders answers the door and invites Henry inside and walks him back to the family room to meet her sons.
 
Mrs. Sanders: “Boys! This is Henry, your new babysitter. The one Krystal recommended.”
 
Jackson: “Hey.”
 
Mrs. Sanders: “Jackson Randolph Sanders! What kind of greeting was that? Put the laptop down and get up and introduce yourself to Henry like a proper gentleman.”
 
Of course Jackson knew better than to just say “Hey.” But he needed that little scolding in order to have an excuse to set his laptop down just right, so it can capture what will be taking place once his mom leaves. He gets up off the sofa and steps over to the end table and places his laptop just so, where it will capture the entire family room in it’s camera. Then he walks over to the redheaded boy standing beside his mother.
 
Jackson: “Hello Henry. I’m Jackson.”
 
He then extends his hand so they can shake hands.
 
Jason: “Hello. I’m Jason. We’re happy that you came to hang out with us.”
 
Jason also extends his hand to be shaken.
 
Mrs. Sanders: “Henry’s here for more than to just to hang out with you. He’s your babysitter, so you both need to be on your best behavior, or you know what you’ll be getting when I get home.”
 
Both boys say: “Yes. Ma’am.”
 
Mrs. Sanders: “Henry. They’re both good boys. You shouldn’t have any trouble with them. There’s food in the fridge if you all get hungry. If there aren’t any questions, then I’ll be off.”
 
Henry: “No Ma’am. Everything is pretty straight forward. Go and have a fun afternoon and don’t worry about Jackson or Jason. We’ll get along just fine, I’m sure.”
 
Henry walks Mrs. Sander to the door and watches her as she leaves. When he returns to the family room, both boys are sitting on the sofa staring at him.
 
Jason: “We’re so glad you came to hang out with us. We’re really tired of having a girl babysitter.”
 
Jackson: “Ya. Now maybe we can do boy stuff.”
 
Henry: “Ya. I guess by the time you get to your age, having a girl watching you and doing what she wants you to do is getting pretty old. So. What kind of guy stuff do you want to do?”
 
Jason: “Wrestling.”
 
Jackson: “Ya. Mom never lets us wrestle. Krystal wouldn’t let us wrestle either.”
 
Jason: “But guys like to wrestle. Not just sit around.”
 
Henry: “Why won’t your mom let you wrestle?”
 
Jackson: “She says we’ll get too rough and break things.”
 
Jason: “But we won’t.”
 
Henry: “Actually. This room is pretty big. If we just move some of the furniture over to the walls, there should be plenty of room for you two to wrestle without breaking anything.”
 
Jason: “Really! You’ll let us wrestle?”
 
Henry: “I don’t see why not. Wrestling and being a boy go together. So help me move this stuff out of the way and you boys can have your fun.”
 
All three boys move the furniture to the walls. Jackson makes sure nothing gets put in front of his laptop.
 
Henry: “That does it. Everything’s out of the way. Go for it guys. Have fun.”
 
Jason: “Aren’t you going to wrestle with us?”
 
Henry: “Oh! I don’t know. You two are close to the same size, but I’m much bigger and stronger than you, so it wouldn’t be fair.”
 
Jackson: “You could be against the two of us.”
 
Jason: “Ya. That would make it fair. Right?”
 
Henry: “Maybe. But I’m not sure your mom would want me to be wrestling around with you.”
 
Jason: “Please! We wanted a boy sitter so we could do fun stuff. We won’t tell mom. Please!”
 
Henry: “Okay. How can I turn down your puppy dog eyes. But be warned. I’m on the wrestling team at school. So it won’t be easy to take me down.”
 
Of course both Jason and Jackson take self defense classes, karate and judo, but they don’t see any reason to let Henry know they can handle themselves. Let it be a surprise.
 
Henry: “Okay then. Shoes off though. We don’t want a shoe kicking someone in the face and then have to explain the black eye.”
 
When all three boys have their shoes off, they go at it. Jason and Jackson hold back. They let Henry push them around and almost pen one of them before the other one pushes him over. All three boys are having fun, because it’s true their mom doesn’t let them wrestle at home. That’s why she pays for the classes they attend.
 
Henry: “You two are pretty good. I almost got each of you until the other one pulled me off. Of course I’m holding back so I don’t hurt you. But that doesn’t change the fact you’re good.”
 
Jason: “We can do better.”
 
Jackson: “So you don’t have to hold back just because we’re younger than you.”
 
Henry laughs: “So you think you can take me, is that it?”
 
Jackson: “I know we can.”
 
Henry: “You want to put something on it?”
 
Jason: “You mean like a bet?”
 
Jackson: “We don’t have any money and mom would blister our butts good if she found out we were gambling.”
 
Henry: “It doesn’t have to be money. It can be anything. You name it.”
 
Jason: “Anything?”
 
Henry: “Sure. You name it and that’s what we’ll wrestle for.”
 
Jason: “Awesome. Strip Wrestling. First one stripped naked is the looser.”
 
Henry’s mouth drops open. Is Jason serious?
 
Henry: “I don’t know about that Jason.”
 
Jackson: “You said anything. Did you mean it or were you lying to us?”
 
Henry: “Of course I meant it. But don’t you think wrestling to get someone naked is sort of weird?”
 
Jason: “Nope. That’s it. Strip Wrestling. Here we come for your clothes.”
 
Jason jumps on Henry knocking him over, Henry lands on his back. He immediately spins over to try and get on top of Jason, but Jackson jumps on top of Henry and now they’re a boy sandwich with Henry in the middle. Henry sees the error of his ways and tries to pull himself out of this position only to find himself being clung on to by four hands and four legs. It takes awhile but eventually Jackson has Henry by his arms and Jason has him by his feet. As much as Henry struggles to get free, they have him pinned. The good thing for Henry is that the boys can’t start pulling his clothes off because their hands are busy just trying to hold him down. He’s not sure how these boys got this upper hand on him, because they sure weren’t this good when he first started wrestling them, but he knows he needs to get back in control of the situation.
 
Henry starts to push off with his feet, when he feels something cold go around his ankles and soon his feet are immovable. He’s not sure what Jason just did, but he can’t get his feet separated to get leverage to throw the boys off of him. The boys roll Henry over onto his belly and Jackson pulls Henry’s arms out over his head. He’s stretched out. Henry feels Jason moving up his legs. Soon Jason is sitting on his butt. Then he feels his tee shirt being pulled up. Jason is working on removing his shirt. That means Jason is no longer holding his legs, so he tries to push off with his feet yet again, but his feet are still being held together somehow.
 
He feels his shirt slowly being pulled up towards his neck and head. As long as he lies flat on the floor on his belly, Jason has a difficult time pulling Henry’s shirt up, but as soon as he wiggles around to try and get free, his shirt is released from between Henry’s body and the floor. Jason take advantage of this and pulls Henry’s tee shirt up more. It takes a little time, but finally Jason has Henry’s shirt up over his head, so Henry can’t see anything. Henry struggles hard to keep his shirt from clearing his head but loses the battle and now his shirt is only dangling on his arms, bunched up at his wrists. Jason sits right on Henry’s head while grabbing one of Henry’s wrists below the shirt, so Jackson can pull it free. Then the boys do the same thing with the other arm.
 
Henry can’t believe these boys have him shirtless.
 
Jason: “Look Jackson. Henry’s got hairs under his arms and they’re red.”
 
How embarrassing. He’s shirtless. This is the first time in a very long time anyone has seen him shirtless. Henry hates when people see his pale skin. It’s not like he don’t try to get a tan, but being a redhead, he doesn’t tan. He just burns. He’s feeling like the kid in the movie Powder. These boys are seeing parts of him, that he doesn’t let anyone see, not even his girlfriend.
 
As Henry evaluates his situation, it quickly changes. Jason has a hold of one wrist and Jackson the other and they both pull back until his arms and hands are crossed on his back. He then feels that same cold something around his wrists and soon his wrists are as immovable as his feet.
 
Now that Henry’s secured, the boys roll him over onto his back. He immediately sits up and stares at his feet which have been secured with a zip tie. No wonder he can’t get his feet free. Then it dawns on Henry, that his wrists must be zip tied too. He’s tied up with no way to get free. He’s at these boy’s mercy. How did this happen?
 
Jackson: “Boy! That was work. Let’s take a break Jason, before we finish stripping Henry.”
Henry: “There’s no need for that Jackson. I give up. You two win.”
 
Jason: “No Way! You can’t give up. Men don’t give up. Men fight to the end.”
 
Jackson: “He’s right, you know. We haven’t won until you’re stark naked.”
 
Henry: “No! I give up. Cut me loose. Right now.”
 
Jason: “You know Jackson. I think our new babysitter needs some motivation to fight harder. What do you think?”
 
Jackson: “You might be right Jason. What do you think Krystal?”
 
Henry quickly looks around to see if his girlfriend is hiding in the room someplace.
 
Krystal: “Ya. I think Jason’s right. He needs more motivation. Amy and Cassie, do you agree.”
 
Jackson: “Well. Let’s see if this motivates Henry to fight harder to keep his clothes on.”
 
Jackson walks over to his laptop and clicks the keys so that Krystal, Amy and Cassie are fully visible on the screen staring down at Henry.
 
Henry: “You’ve been watching all of this?”
 
Krystal: “Of course. This was all my idea.”
 
Henry: “Why!”
 
Krystal: “Because you’re so up tight about me seeing even your chest or back bare. Now I’m going to get to see every inch of you bare as a newborn baby. But don’t worry, sweetie. It’s for your own good. Boys aren’t supposed to be so modest. Are they Jason?”
 
Jason: “Nope. See!”
 
Jason immediately strips off his clothes and stands stark naked for everyone to stare at. Henry can’t believe his eyes. This boy is standing naked in front of his girlfriend and her friends.
 
Cassie: “Remember when I told you that you were cute, Jason. Now you’re the cutest thing ever.”
 
Jason: “Thanks!”
 
Jason dances around the room naked, with his skinny, little, cut, one and a half inch pecker sticking straight out in front of him.
 
Henry gets a bright idea, while watching Jason dance naked.
 
Henry: “Jason. You’re the first one naked so you lose. The wrestling match is over.”
 
Krystal: “Nope. You don’t get out of this that easy. Jason wasn’t stripped naked. He took his own clothes off, so you didn’t win and he didn’t lose.”
 
Henry: “Okay then. There’s still Jackson. Cut me lose and let’s see who wins between just me and Jackson.”
 
Krystal: “I don’t know. Jason isn’t officially out of the wrestling match. He’s just naked, so you can’t strip him, so he can’t lose.”
 
Henry: “Okay, but Jackson can still lose if I strip him naked.”
 
Krystal: “What do you say to that, Jackson?”
 
Now Jackson has been worried about this part of Krystal’s plan from the very start. He isn’t like Jason anymore. He gets embarrassed being naked now. But he did agree to the plan when Krystal laid it out for them, even knowing that this was going to happen. Jackson can feel his face turning red already.
 
Jackson: “Not if I take my clothes off too, then I can’t lose either.”
 
Jackson, takes a deep breath and strips off his clothes leaving him stark naked like his brother. The two boys are almost twins standing there naked, except that Jackson’s penis is about a quarter inch longer and just a smidgen fatter than Jason’s penis. Yep, he’s starting puberty.
 
Amy: “Oh. My. Jackson. Remember what I told you earlier? You’re just the cutest thing ever. I could eat you up!”
 
Jackson’s face goes as red as Henry’s hair. Then to his utter embarrassment his dick begins to swell and before he can turn away from the laptop, he has a three inch boner.
 
Jason: “Awesome Jackson. I can’t wait for mine to get that big.”
 
This only embarrasses Jackson even more, because he knows that his dick isn’t big at all. It just looks big to Jason because his boner is only two inches long.
 
This is the main reason Jackson begged and pleaded with his mother to change babysitters from a girl babysitter to a boy babysitter. Krystal always found ways to get him naked and his dick always decided to show off for her. Now that his bodies changing, it’s just too embarrassing for girls to see him like this. He’s hoping that this will be the last time he has to be naked for Krystal. He realizes he’ll probably have to be naked for Henry, because babysitters like to get their charges naked, but at least Henry is a guy.
Krystal: “Okay boys. Break time’s over. Get back to winning your wrestling game.”
 
Jackson and Jason move back over to Henry and go straight for his belt to get it unfastened.
 
Henry: “Please. Don’t do this. I’m begging you. I’ll let you do whatever you want. Just don’t do this. Not in front of Krystal and her friends.”
 
Jackson: “We have to. It’s the only way we get you for a babysitter.”
 
Henry: “No it isn’t. I’m already your babysitter. You don’t have to have Krystal anymore.”
 
Jackson: “No you don’t get it. Mom doesn’t trust boys to babysit. She thinks you’re all perverts and the only reason you want to watch us is so you can get us naked and play with our wieners. Mom only trusts girls, because girls will never do something like that. But she’s so wrong. The reason girls babysit boys is so they can play with us naked. Krystal’s played with our wieners from the very first time she started babysitting us.”
 
Jason: “Ya. That’s why we agreed to her plan. That’s why we’re naked right now. It’s also why, in a few minutes, you’re going to be naked too. We have to strip you. Then Krystal will let you be our babysitter. Otherwise she won’t. She’ll go to mom and tell her you made us get naked and mom will be all mad and we’ll never see you again. We’ll get Krystal back as our babysitter.”
 
This is a lot for Henry to take in. He always thought Krystal was the sweetest girl he’s ever known. He’s known her since first grade and he never knew she did this to boys. Then he feels a tugging around his waist and his belt comes free.
 
Jason: “Now lie back so we can get your jeans unfastened.”
 
But instead of lying back, Henry bends forward so the boys can’t get to his zipper. That doesn’t work though, because they push him down and then Jason sits on his chest. Jackson goes for the snap holding Henry’s jeans fastened and then lowers the zipper.
 
Jackson: “Okay they’re unfastened.”
 
Jackson begins tugging at Henry’s jeans and slowly they slide down revealing his blue and gold boxers. Because Henry is struggling, his boxers slide a little ways down too, so now the top of his crack is showing.
 
Henry: “Please Jackson. Don’t do this. I’m begging you.”
 
Krystal: “Don’t listen to him Jackson. Pull his jeans down and then his undies.”
 
Jackson does as Krystal instructs him. He’s always did what Krystal has told him, ever since she first started babysitting him when he was nine years old. It takes some work, but Jackson gets Henry’s jeans down to his ankles. Of course he can’t take them off yet, because of the zip tie, but that can happen later. First he needs to get Henry’s boxers down revealing Henry’s dick.
 
Jason: “Let me pull his boxers down.”
 
Jackson: “Okay. Let’s switch places.”
 
Once they’ve switch places, Jason wastes no time tugging at Henry’s boxers. Surprisingly they easily slide down his legs.
 
Jason: “WOW! He’s got red hairs down here too!”
 
Sure enough, Henry’s pubes are the same color as the hair on his head and under his arms.
 
Jason: “Look Jackson. Henry’s pecker is bigger than yours.”
 
Both boys and the three girls stare at Henry’s limp three and a half inch, uncut dick, lying on it’s hairy bed of red pubes.
 
For Henry, this is the worst day of his life. He’s naked in front of other people. He’s naked in front of his girlfriend. She’s staring at his most private parts.
 
Jason: “Why’s his pecker look so funny.”
 
Krystal: “It’s because he’s uncircumsized, instead of cut like you and Jackson.”
 
Jason: “Uncircumsized?”
 
Krystal: “Yes. That’s when doctors cut that loose skin off the end of your wiener, when you’re a baby.”
 
Jason: “You mean this skin?”
 
And before Henry knows what’s happening, he feels little hands touching his dick and pulling at his foreskin.
 
Krystal: “Jason. Go ahead and slide that lose skin back and you’ll see that Henry’s wiener looks just like yours.”
 
Jason: “Like this?”
 
Jason pulls Henry’s foreskin back to reveal his pecker head.
 
Jason: “Oh! WOW!”
 
Jackson is staring at everything Jason is doing, because he’s never seen an uncut dick before either. Henry is just trying to keep calm, as his dick is being played with by an eleven year old. He’s losing his battle.
 
Jason: “Look! Henry’s pecker is growing. I think he’s getting a boner.”
 
Henry: “Please Jason. Stop. I don’t want the girls seeing me with a boner. Please stop.”
 
Krystal: “Jason honey. Don’t listen to him. Go right ahead and play with Henry’s wiener all you want to.”
 
Jason: “Really. You mean it?”
 
Now Krystal has been watching Jason since he was eight years old and Jason is used to obeying Krystal without question. So with her giving him permission to play with Henry’s pecker, he, of course, is going to play with it. As Henry’s dick swells, his foreskin draws back and gets tight and soon Henry’s pecker is boned up and his pecker head is in full view.
 
Jason: “Look Jackson. Now Henry’s pecker looks like ours. But it’s way bigger.”
 
Henry is sporting a five inch, fat erection and Jason is having fun pulling it back and letting go and watching it slap against Henry’s body.
 
Jason: “This is so much fun.”
 
Henry, on the other hand, can’t get past how this is making him feel inside. He can feel his sperm rising up. He’s never had someone play with his dick before and the feelings he’s experiencing is beyond his control to stop them. It isn’t long before Henry’s dick is twitching.
 
Jason: “WOW! Did you see that. Henry’s pecker just jumped right out of my hand. Did I make it do that?”
 
Krystal: “You sure did, Jason. Play with it some more and see what other games it’ll do for you.”
 
Jason grabs Henry’s twitching dick and rubs it and pulls on it and of course it twitches even more. As it does, Henry is raising his butt up off the floor trying hard to hold everything inside. Jackson is going for a ride as Henry tries to hold back what is about to happen. Jason is just having the time of his life. He’s played with Jackson’s pecker lots of times, but it never did things like Henry’s is doing. Henry can’t hold back any longer. Knowing what is about to happen and all the people that are going to see it, is beyond humiliating and there’s nothing he can do to stop it. With a mighty push, out comes his first squirt of sperms.
 
Jason: “OH! He’s peeing!”
 
Jason lets go and watches as Henry spasms and squirts load after load of his boy juice out over his belly. Jackson jumps off of Henry just in time to keep from getting squirted. Henry is lying on the floor naked from the knees up, squirting sperm all over himself, knowing that everyone is watching him. Eventually he stops squirting. Henry has his eyes tightly closed. He doesn’t want to see the faces of everyone that just watched him orgasm.
 
Jason: “WOW! That was fun. Can I do it again?”
 
Krystal: “Yes dear. A little later. But for now, while Henry is too ashamed to do anything about it, go ahead and finish stripping him.”
 
The boys cut the zip tie around Henry’s ankles and pull his jeans and boxers off leaving the poor boy totally naked.
 
Krystal: “Wow! Henry. You look amazing naked. This would have never happened if you would have just let me see you. If you had worn the Speedo that I got you for your birthday. I just wanted to see my boyfriend’s skin.”
 
Henry slowly opens his eyes to see he is totally naked lying on the floor, with Jackson and Jason both staring down at him. All three girls are watching him from the computer. He’s naked. He’s on display. He’s humiliated and embarrassed. He’s got his spunk all over his belly and in his pubes.
 
Henry: “Can someone cut the zip off my wrists now?”
 
Krystal: “Sure Henry. But you have to stay naked and do whatever I tell you. Otherwise, this little fun time might get out to all the kids at school.”
 
Henry: “What! You taped this?”
 
Krystal: “Of course. I want to replay this day over and over again.”
 
Henry: “Okay. Just cut my hands free. I’ll do whatever you say.”
 
Jackson cuts Henry’s hands free and now he’s just lying on the floor spread eagle with his dick and balls and everything else completely visible for everyone to see.
 
Jason: “Henry? You’re not mad at us are you?”
 
Henry: “No Jason. I’m not mad at you.”
 
Jackson: “You look mad.”
 
Henry: “I’m not. Really, I’m not. I just feel very strange is all. I don’t like it when people see me naked. And this has been overwhelming for me.”
To Henry’s surprise, Jason comes over and lies down beside him and kisses Henry on the cheek.
 
Jason: “Don’t be sad. You can play with my dickie if you want.”
 
Henry: “It wouldn’t be right.”
 
Jason: “Why not. I played with yours.”
 
Henry: “I’m your babysitter.”
 
Jason: “Krystal was my babysitter and she played with my pecker all the time.”
 
Henry: “Oh! Really!”
 
Jason: “Ya. And I liked it a lot. It always made me feel funny inside. Like I was going to pee, but I never did. Not like you did.”
 
Henry: “That’s not pee, Jason. It’s sperm. It’s what boys use to make babies.”
 
Jason: “It is! WOW! I can’t make my dickie squirt out anything. Jackson can’t either.”
 
Henry: “You both will soon enough. Jackson first because he’s older, but then shortly after him, you’ll do it too.”
 
Jason: “Cool. I can’t wait until I can shoot stuff out my boner like you. That was awesome.”
 
Jason takes Henry’s hand and moves it down to his penis and makes Henry rub it.
 
Jason: “I like that. Rub it on your own. Please.”
 
How can Henry resist a cute naked boy who has just placed his hand right on his dick. Henry begins rubbing Jason’s tiny dick and sure enough it gets hard and Jason squirms around as Henry plays with it. Now Jason always stopped playing with his dick when it made him feel funny inside, but Henry isn’t stopping and before long, Jason has his first dry orgasm and he’s both amazed and scared.
 
Henry: “How did that feel?”
 
Jason: “Awesome, but I think you broke something inside me!”
 
Henry: “No. Nothings broke. You just had an orgasm, like I had, just you can’t squirt yet. As awesome as your dry one felt, it’ll be a thousand times better when you have a wet one.”
 
Jackson: “Was it that good?”
 
Jason: “Heck ya. You should let Henry do you.”
 
Jackson lies down and places Henry’s other hand right on his penis.
 
Jackson: “Will you show me?”
 
Henry without thinking about it, begins playing with Jackson’s slightly larger dick and sure enough he bones up and shortly he’s squirming on the floor as he has his first ever dry orgasm.
 
Jackson: “WOW! That was awesome.”
 
All three guys lie on the floor thinking their own thoughts as the girls watch everything from the computer. They don’t say a word. They just watch as the guys get to know each other. Never in their wildest dreams did they think they would get to witness this. Yes. Krystal wanted to see Henry naked, but to get to see him play with the boys sexually. No way did she ever think he would do that. Yes. She loved doing it to the boys, but she never thought boys did it with each other. Now she knows they do and they enjoy it.
 
Henry sits up, grabs his discarded boxers and wipes himself clean.
 
Henry: “Well guys. What do you want to do now?”
 
Jason: “Wrestle. But now we grab each others dickies and make them orgasm.”
 
All three boys laugh and grab for each others dicks as they squirm around on the floor. They totally forget that the girls are watching them. By now it just doesn’t matter. They’ve already seen everything. Eventually, Jackson gets free of the other two and turns his laptop off and then jumps right back into the wrestling match. His own dick is boned up and feels absolutely awesome. This is why he wanted a boy babysitter. He can have a boner and no one makes a big deal out of it. They’re all boys. It’s so different when you get a boner and it’s a girl playing with it. Jackson likes having Henry play with his boner and make him have an orgasm. He knows Jason likes it too. The boys don’t even stop to eat. They continue playing with each other right up until they hear the boy’s mom pull into the driveway. Then they quickly jump up, get dressed and push the furniture back in place, before she makes it into the house.
 
Henry: “Oh. Hi. Mrs. Sanders. You’re back so soon?”
 
Mrs. Sanders: “It’s been almost five hours.”
 
Jackson: “That long. It feels like you just left a few minutes ago.”
 
Mrs. Sanders: “I guess time flies when you’re having fun. You all sure look like you’ve been having fun. You look wore out.”
 
Jason: “We’ve been playing in the backyard. Tag and keep away and all kinds of boy games. It’s been awesome.”
 
Jackson: “Ya mom. It’s been really awesome having Henry for a babysitter. He likes playing boy games with us, instead of the girl games Krystal always played.”
 
Mrs. Sanders: “Well Henry. It looks like you’re a hit with my boys. I have to admit, I was a little leery having a teenaged boy watching my little boys, but they seem to really have taken to you. If you would like to baby sit them full time. Then the job is yours.”
 
Henry looks at the boys and the grins on their faces tells it all. He has to watch them.
 
Henry: “Sure. I’d love to watch them.”
 
Mrs. Sanders: “I’ll need you to come here after school and watch them until I get home from work every day. If I leave them here by themselves the house would be tore up.”
 
Henry: “I can do that. Everyday after school. When do you get home, so I can let my mom know when I’ll be getting home?”
 
Mrs. Sanders: “Around 5:30. So you’ll be watching them for about two and a half hours each day. That won’t be too much for you, will it? I know teenaged boys have a life of their own.”
 
Henry: “No. Mrs. Sanders. That won’t be too much. I pretty much don’t do much right after school anyway. I use that time to wind down from school. So, if it’s okay with you, I’ll work that pent up energy out of them every afternoon. Just like we did today.”
 
Both Jason and Jackson grin really big. Henry just said, “Like we did today.” Which is boy speak for, we are going to play naked every afternoon, from now on.
 
Mrs. Sanders: “That would be wonderful. Because sometimes the boys are a real handful at night. So by all means wear them out good.”
 
Henry: “Oh I will. You can count on that. I know exactly how to get boys calmed down.”
 
Mrs. Sanders: “Are you two okay with that?”
 
Jackson and Jason: “Yes ma’am.”
 
Mrs. Sanders: “Then it’s settled. Henry is you new babysitter.”
 
Henry: “Thank you Mrs. Sanders. I better be getting home. I don’t want mom worrying about me.”
 
Of course Mrs. Sanders loves hearing how Henry is concerned about his mom worrying, which is exactly why he said it.
Mrs. Sanders walks Henry to the door and hands him money for watching the boys. She tells him that from now on, she’ll be paying him each Friday evening when she gets home from work, for his after school babysitting. If she goes out over the weekend, she’ll pay him separately for those babysitting jobs.
 
Over the next couple years, the boys have a wonderful time playing naked every afternoon together. Henry is playing with Jackson’s boner when he has his first wet orgasm, just like he is there for Jason’s first one. Both boys are overwhelmed by how much better a wet orgasm feels over a dry one. Mrs. Sanders is happy with Henry watching her boys, because like Henry promised, the boys are calm and collected every night when she gets home from work.