The Babysitter

Note: this is not a cuckold story but it's built like one. If you like stories about dominant sexual women who tease sex without giving it, this is the story for you. Otherwise, don't bother commenting or reading.

*****

Hey there, how are you? Your name is Brandon, right? I'm Jackie, it's nice to finally meet you.

I think we had biology together a couple years ago, right? God I hated that class. Mr. Terrence was such a perv. I swear, he was always trying to look down my shirt. There was one time after school when I was wearing this mesh top, probably two sizes too small. My tits were practically bursting out of that shirt, and Mr. Terrence was clearing gawking at them when he was supposed to be tutoring me. So I said, you know what Mr. Terrence? Just take a good look already so we can get on with the lesson! And I popped out my left tit and then my right, shook them around a little in his face and he practically fainted! I bet the perv went home and jerked off to it at his house, the weirdo.

Gosh I'm sorry for going on such a tangent, that's so typical of me. I can be such a scatterbrain sometimes. I swear it's a miracle I even graduated with the rest of our class. It always felt like everyone was so smart there! Ashton and all his friends got those scholarships to Harvard! So many people are going abroad to great schools in Europe and Asia. It's like you and I are the only ones left in this dumpy North Carolina town, isn't it?

Look at me , I did it again! Scatter brain Jackie! Let me actually get to the point for once!

I was really distressed when I heard about your breakdown. It's really sad to hear about something bad happening to a former classmate, even if you didn't know him well. I wrote a long Facebook post in solidarity when you were in the hospital, talking about my own experiences with my cousin who had a mental breakdown a few years ago. It's really sad when a person gets to the point where they can't function in their life because of mental issues. Your parents sent me a message after they saw the post, thanking me for my support. I told them I would do anything to help them in their time of need, so here I am now!

What I'm trying to say is that your parents know you need a lot of attention and care, and that's why they've hired me. When they're out of the house and busy, I'll come over and keep you company and cook you food and make sure you're in bed when you're supposed to have your rest. I guess you can think of me as your babysitter if that's alright with you! I think we can have a good time if you keep an open mind, right?

I know this must be a lot for you to take in. Your parents told me that you feel that you've gotten better and don't need to be taken care of anymore. But trust me, after what you went through, you need to listen to us. Rest and care is what you need right now.

You're probably not too happy about this. It's fine, I get that. Just a few months ago, we were classmates and you were studying in the same library I was skipping class to hang out in! Now here I am, in your house, and your parents are paying me to tell you what to do? I know it's weird. But if you go along with it, it will be much better for all of us. When I say it's time for you to go to bed, you have to listen to me. I know what's right to get you healthy. I may not have a nursing degree, but I baby sat all throughout high school with kids of all ages. And I know you're not a kid but with your condition, well, it might be best if you have someone who can deal with kids like me. I may have gotten D grades but everyone deserves a second chance, even a dust brain like me!

Brandon, why don't you go eat the macaroni and cheese I made in the kitchen? You must be hungry. After that, we can talk about getting you ready for bed.

Brandon, is it alright if I ask you a personal question while you eat? I was talking to Ashton about this new job with your parents, and he mentioned that you had a crush on me for a little while back in high school. Is that true?

Oh I didn't mean to make you embarrassed! Trust me, I'm used to guys having crushes on me. At my last babysitting job, one of the boys did. He was ten, it was really cute actually. It was less cute when I learned his dad felt the same way! He was driving me home one night and pulled over to show me his cock. I admit it was one of the bigger cocks I have seen but it was hairy and I didn't know what to do. He kept touching my breasts and trying to undo my pants. I wasn't sure I wanted it to go on, even though I was starting to feel a tingle in my back and legs. He wanted to strip me nude and mount me over the backseat of his car. I suggested I give him a handjob instead, which he didn't seem to like until I got my two saliva coated palms wrapped around his shaft. When you develop tits like mine at age twelve, you learn quick how to give a perfect handie! I had him gushing like a waterfall in a couple of minutes. From then on, it wasn't a problem for me to jerk him off after my shift on the ride home.

Whoops! Look me, blabbing on like an idiot when you've finished eating ages ago! Let me get this cleaned up and then I'll get you into a bath.

Brandon, why are you looking at me like that? Of course I'm going to have to supervise your bath. After all that's happened, you can't be in there alone. It's my job to take care of you, so stop fighting me on this. Let's get you out of those clothes already. There we go, now follow me upstairs. Step right into the water, here you go.

As I said, don't be so embarrassed. I've seen a naked man before, Brandon. There's nothing wrong with a little cock and balls. Ack, I mean, I'm sorry, I didn't mean to call you little, or, well, you're not big really either but it wasn't nice of me to—oh my god I'll shut up now!

Ugh, I'm sorry. I'm such a ditz, that was really not nice of me to say. Here, let me take another look. Please stop squirming and let me hold it. I was going to have to wash it anyway Brandon so at least let me look at what I'm doing!

See, it's not as small as I thought. Actually, now that you're getting hard I can see that I was totally wrong about your size. You're definitely average, or at least only a little bit under average. That's definitely not little, don't you worry!

Let me get under there to wash your balls. There we go. Wow, you're really twitching. Have you gotten laid at all since you've been in the hospital? ... Brandon, did you get laid at all before you were in the hospital? ... Oh my god, Brandon, tell me it's not true, you're not a VIRGIN, that can't be possible. You're serious? So these hands, right now, are the first time you've ever gotten a woman to touch you?

Oh no, don't feel bad about that. It's alright. Actually it's great. You should be celebrating. Today's the last day you have to say that! In this bath, you've got two of the best hands out there touching you right now!

Brandon, you're twitching so much, do you want me to keep going? I can help you Brandon, it's alright. Just let me do my work. You know, for a young man like you, cumming regularly is definitely important to your health. Let me help you in this bath, right now. Just a few more strokes and I'll have you shoot a dirty load right into this bath water. Just a few more strokes, here, let me touch your balls... oh did you like that? We're almost there, don't you feel it? Just give in to it, let my hands take over. I'm taking good care of you, feel that? Did you like that Brandon? Feel your balls start tightening and shoot a fat load for me, right now, please!

How was that? Your very first handjob, did you like it? Don't get too used it, though. It'll be tough to find a girl as good with her hands as me. It's actually a special talent of mine. Jackie Jack Off! That's what Ashton used to call me. Did he ever tell you that? I guess it was a big secret back then. I used to jerk him off all the time back in high school. It's how I got so good. I mean, Ashton's a special guy. His brain is wired totally differently than anyone else. It's what makes him so smart, but it also makes his hormones totally weird. The guy's dick is like a genetic mutation. I never measured or anything but there is no way it's under a foot. And he gets hard every couple of hours if he doesn't unload. I once drained his balls one afternoon only to get a text three hours later that he was clutching himself in pain he was so hard and full of cum again. And every load is like forcing a gallon of pudding through a pen cap. I don't normally like to swallow, but with Ashton if I didn't guzzle down as much as I could it would have practically flooded the room. The guy is a freak, but hey, I'm not complaining. When I could actually get him to stick it in me instead of using my hands, I swear he could hit something inside of me that made his jizz come out my eyes! Like, it felt that way, I meant.

You know what, after I get you dressed and tucked into bed, I think I'm going to take a bath. After all that talk of Ashton, I think I could use some time to turn these hands on myself. Here, step out and use this towel while I drain and refill the tub. There are pajamas for you right there. Let me take you to your bedroom now. I hope you don't mind if I start to undress now? I mean, ugh, I know it's wrong but I want to get into that tub already. Who am I kidding, of course you don't mind. You probably want me naked more than I want me naked!

Are you a tit man, Brandon? Oh please, forgive me, I forgot you said you were a virgin. So you don't even know yet! When the time comes for you to actually get your dick inside a woman, you'll learn quick whether you're a tit or an ass man.

Get into the bed, let me tuck you in. There there, nice and tight. I hope it wasn't too weird having me as a babysitter tonight. And you don't have to worry about me going anywhere. Your parents are paying me a really good amount to be here and I don't need to look for another job or anything. So as long as you need help, I can be come over and watch you. And hey, maybe during a school vacation when Ashton is in town, he can come over and hang with us. You two used to be close, right? And I know I would appreciate it a lot.

Brandon, I said it's bed time. Why are you following me out of your room? I just tucked you in. I told you I'm on fire and I wanted to get to the bath. What are you trying to say?

... oh I see. You're more of a perv than I thought. Do you want to watch me play with myself Brandon? Well, the answer is absolutely not. Maybe with my gabbing about cock and my attempt to take care of you in the bath you got the wrong idea. I'm not here to make you cum, Brandon. I'm here to make you healthy. So you get right back into that bed and you go to sleep. That's more like it, Brandon. Now close your eyes. Here, I tucked you in again. You better not move a muscle. Brandon, I think we had a lot of fun tonight. And if you want to keep having fun like this, you're going to have to follow the rules. Now when I'm over there in your bathroom tub, screwing my brains out to the thought of your friend's freaky dick, where are you going to be? Here, in the bed, that's right. And if I happen to make some noises from the bathroom, noises of thriving ecstatic pleasure, I'm not going to be able to control how you respond to that. So if you want to touch yourself too, listening, that up to you. As long as you don't even think of leaving. Now if you'll excuse me, my thighs are starting to drip onto your carpet and my bath is getting cold. Goodnight Brandon.