Massaging the Babysitter

Posted by: Author: Age: 19 Posted on: 0 comments
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All names have been changed in this story.


As I was growing up the house I lived in was the hang out spot for my brother and his friends.

I had a huge crush on one of my brother's best friends who was probably around 16 at the time of the event this story is mostly about took place. Not only did Chad have cute blue eyes but he was always nice to me, much nicer than any other friends my brother had.

That Saturday my brother was going to be gone all day visiting our dad and my mother had plans that afternoon. I needed a babysitter and I suggested Chad could do the job. I had recently turned 10 at the time and my Mother assured Chad that I would not be a problem and that his main job was to 'make sure the house didn't burn down' my Mom used to say that often.

That evening started out with Chad and I watching a video and then pillow fighting and I was having a great time. Chad was always cracking his knuckles, back, neck and even his toes. I asked him why he liked to do that so much and he took my hand and pulled on each of my fingers until they made a cracking sound. I liked the way it felt when he cracked my knuckles and I returned the favor by cracking his knuckles, eventually I was standing on his back cracking that as well.

I suggested Chad and I pretend I was a 'massage person' and so I made 'tickets' for massages with a deck of 3X5 cards, each card said either shoulders, back or neck. Eventually I started making silly tickets for example; a nose massage, an eyeball massage, etc. One of the goofier tickets I made was for a belly button massage. Chad would pick a 3x5 card from my hand at random, eventually he picked the belly button massage ticket.

Chad took off his shirt and laid down on the couch he had an 'outie', and we both laughed as I massaged it. Then Chad got ready to ask me a question but then said 'nevermind' and I told him I wanted to know what he was going to ask. 'Do you want to massage my weeny?' he said with a nervous laugh.

At first I giggled and said 'that's gross.' Yet soon after I asked if he really wanted me to massage his penis, in a very round about way he basically said 'yes'. Now at this time as far as I knew a penis had one purpose, to pee and that's it. Chad unbuckled his pants and exposed his penis, scrotum and bushy brown pubic hair. In retrospect I clearly remember that chad was not circumcised.

I was in complete awe, I had never been this close to a boy's private area let alone one that was big and hairy.

Chad told me just to pump up and down, so I grabbed hold of his stiffening penis and started the massage. It is important to know I was not connecting this with anything sexual but I was certainly amazed at what I was seeing and curious. I asked Chad if he had a bone in his penis and he said it was stiff because it needed to be relaxed.

As I pumped I could tell he was enjoying it and I really felt I was doing a great thing. It seemed I could do no wrong because if I went slow Chad would moan with obvious pleasure and if I went fast he would exclaim 'Oh yeh' repeatedly. I will never forget the look on Chad's face as I 'massaged' him, it seemed as if he could feel what I was doing throughout his whole body.

With each stroke Chad shook all over and his eyes would roll back and he continued to moan and say 'oh yeh' and then his breathing got heavier and the moaning got much louder. Chad insisted I was almost done and to keep going. When I saw a long string of semen shoot out of his penis I thought it was pee but quickly realized it was something else. Chad now insisted even stronger 'It's ok, don't stop, keep going' and I did watching in complete amazement as this thick whitish liquid squirted from his penis to his stomach and eventually oozed onto my hand.

When it stopped I held my hand up high, gazing at the gooey liquid in utter curiosity asking what it was and offering my own observations 'looks and feels sort of like snot' by this time Chad had jumped off the couch, grabbed his shirt and was wiping his stomach. Chad made me wash my hand and began apologizing profusely, he put his shirt in the washing machine, and continued apologizing. In between apologies he was begging me not to tell and I'd reassure him that I would never tell.

Chad explained the things that would be bad for him if I told and we 'pinky swore' I'm guessing nearly a dozen times before my Mom got home. Every time Chad saw me after that day he would take me aside to see if his secret was safe and I always assured him it was.

AND... A few months later Chad baby sat but refused to play massage with me even though I said it could be hand massages only if he wanted. Chad baby sat occasionally until I was old enough not to have a sitter but nothing else ever happened like that again.

A few weeks after my encounter with Chad, I tried to give my 9 year old neighbor a 'Weeny Massage' but he did not respond the way Chad did and it quickly got boring. He said it hurt too much and his wiener was a small compared to Chad's. So even until this day the encounter Chad and I had is the only one I have had like that and remains my most erotic memory.

I still see Chad sometimes and as far as the two of us are concerned nothing ever happened.



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