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Babysitting Bobby

Posted by: Author: Age: 16.5(then) Posted on: 0 comments
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Bobby was very immature in most ways but oh so mature in others!!


Bobby was a boy who lived in my neighborhood for as long as I can remember. It was just him and his mom. No sisters, no brothers, no father-just one very overprotective mother. She would not let Bobby do much of anything. Consequently, Bobby didn't really have any friends his own age and was often picked on by the other kids. One day some kids were harassing Bobby and I stepped in to help him out. From that moment on he became my shadow. At first having him around annoyed me no end but I soon grew to accept it. Despite our age difference, I was 15 and he was 12, a friendship was formed that lasts to this day. Bobby's mother grew to look upon me as the older brother her son never had.

Now let's fast forward a year and a half. Not much has changed for Bobby, unfortunately. I on the other hand, have finally gotten my driver's license and had a lot of mutual jack off sessions with my best friend (future story). One night around 7pm the phone rings and I hear my mom talking to Bobby's mom. My mom then puts me on the phone. Bobby's mom explains that she had an unexpected emergency and needed to go away for the weekend. She asked me to babysit Bobby while she was gone and said she would pay me a lot for doing it. I said I would and looked forward to spending time with him since we had not hung out much recently. She then asked me to play it like a sleepover, since Bobby had never had a friend spend the night before. She said she would have him call me and invite me for a sleepover. We hung up and not even five minutes later Bobby is calling me. I could hear the excitement in his voice as he stammered out the invitation for a sleepover. I told him I could hardly wait and would see him the next night.

I rang the doorbell and the door opened immediately-like he was there just waiting for me. He grabbed my backpack from me and went running down the hall. While he was doing that his mom slipped me some cash and phone contacts where she could be reached. I quickly stuffed it all into my pocket. Bobby came running back into the room, grabbed my hand and led me off to play some video games he had. A few minutes later his mom comes into the room and tells Bobby she has to leave for the weekend. He goes crazy until she explains that he could still have his sleepover with me-she just wouldn't be there. Bobby looks at me and smiles then kisses his mom goodbye.

We ordered in a pizza and watched a couple of movies. It was getting kind of late so I told Bobby we should go to bed. He agreed. He led me down the hall to his bedroom where we would be sleeping. All I really noticed when we went in was one queen bed and some pajamas neatly folded over the back of a chair. I chuckled to myself over the site of the pajamas-no kid I knew over the age of 10 wore pajamas-But this was Bobby after all!!

I pulled off my shirt and Bobby did the same. Next I unbuttoned my jeans. Bobby asked 'Do you sleep in your underwear?'.

'Yes' I said matter of factly. Truth be told, ever since those sleepovers with my best friend I had slept nude but I wasn't going to do that with Bobby right next to me in the bed.

Bobby smiles proudly and announces 'ME TOO!'.

I knew he wasn't telling the truth. After all I had seen the pajamas!! But I said nothing and pulled off my jeans. Bobby did the same. I then went to pull back the quilt and get into bed when Bobby screams with an absolute look of horror on his face 'NOT THAT SIDE!!!'.

I was taken aback. I did not know what to say. All I could manage was 'Oh, is that the side you sleep on?'.

Bobby starts to stutter and ramble about how he peed his bed and didn't tell his mom because he was afraid she would cancel the sleepover and how he didn't want me laying in it all night and that he had peed his bed a lot recently which had not happened since he was about 5...

I pull back the quilt to have a look. All it took was one look and I could tell that it wasn't pee stains on his sheets but CUM stains!!!! I asked him if he wanted me to change them but he said no maybe in the morning. So we got into bed. For the first time in my life I really really looked at Bobby. He was no longer the little boy I remembered. I could not take my eyes off this boy. His longish brown hair framing his face, his skinny little body, his nice smooth chest, and of course the bulge in his tighty whities all looked too perfect to me.

'How long you been peeing your bed?'. I quizzed.

'Couple of weeks now.'

'You sure it's pee?' I quiz further.

Bobby gets this goofy look on his face and asks 'What do you mean?'.

'Well,' I start, 'when a boy gets to be a certain age he changes. And part of those changes include, um, well, your body starts making other things besides pee that need to come out some times.'

Now Bobby's eyes are glued to mine and he asks 'Like what?'.

I could not believe he had no idea what I was talking about. Guess his mother had not gotten around to telling him about the birds and the bees. OK he's got to find out sometime. 'It's called sperm or cum. It is what makes a girl have a baby. You make it in your body and it shoots out your dick. Sometimes, if you make a lot it shoots out by itself.'

'You think that's what it is?'.

'Let's see. Does your dick get hard a lot?'

Bobby's face starts turning red 'Yes all the time.'He mumbles.

'Is hair starting to grow in down there?'

Bobby's face turns even redder and even quieter Bobby mumbles 'Yes'.

'Do you jack off?'

'Wwwwhat's that?' he questions.

'That's where you make the cum squirt out of your dick so it doesn't squirt out while you are sleeping!' I excitedly tell him.

'Can you show me how to do it?'

I glance down and notice that he is hard as a rock as am I but he hadn't noticed that yet. 'Ya, just pull off your underwear!' I eagerly tell him.

'But then you'll see my dick!' Bobby stammers.

'So, I got one too!'

'You gonna take off your underwear too?'

'You want me to?'

'Yes' Bobby whispers quietly.

With that we both pull off our tighty whities. I was shocked at how big and hairy he was for 13!! Now his bush wasn't fully grown in yet but was well on it's way!! And his dick? Not that thick but longer than the other boy I had been with-who was 15!!!! Seeing him like this made me harder than I already was! 'Dude, seeing your dick-I can guarantee you you haven't been peeing your bed! You been cummin' while your sleeping!! Ready to learn how to jack off?' I ask.

'YES' Bobby exclaims!

I take my hard dick in hand and start stroking. Bobby does the same but complains it hurts. I get out of bed and go to the bathroom and find what I was looking for-vasoline!! Bobby is just starring at me as I walk across the room with my boner freely bouncing in the air. I get into the bed, put some vasoline on my hand and gently start stroking his raging hardon!! He lays back and puts his hands behind his head-exposing the whisps of pit hair starting to grow in. I really hadn't planned on this happening, couldn't believe it was happening, but was enjoying ever minute of it!! I start playing with his hairless ballsack while continuing to stroke that nice thin five incher of his!! Soon I settle into a nice rhythm and he starts to fuck my hand while I stroke him. All too soon he is breathing real hard and screaming for me to stop because he has to pee real bad. ' JUST GO WITH IT DUDE-LET IT HAPPEN!!! I excitedly tell him.

Bobby is out of control. I had never seen anything like it. Cum was squirting everywhere!! He hit me in the face, himself in the face, and the rest splattered all over the sheets!! I continued to stroke him until he could take it no more. Without hesitation, Bobby grabs the vaseline and starts to return the favor,

He starts stroking me just the way I had taught him-commenting the whole time how good my hairy six incher and low hanging ballsack felt in his hand. His little hands made my dick feel soooooo good. I was way too excited from what I had just done to him and from what he was doing to me that I just could not last that long. Well before I wanted to, I started having one of the most intense orgasms of my life. Like Bobby, I was shooting wad after wad of cum and it was flying everywhere!!

Once he finished me, he rolled over and started hugging me. Soon we were both hard again. we ground our bodies together while hugging. Soon we were both coming again. The feeling of our dicks rubbing together with all the vaseline and cum between us was one of the best feelings ever!! We eventually got out of bed and went and took a shower together. The rest of the night we cuddled in each others arms.

The rest of the weekend was spent together, naked, jerking each other off time and time again. I made sure we changed those sheets before his mom got home-we did not want her seeing any of our 'pee' stains on the sheets!!!




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