Topic: BabysittingBabysitting

Where I live is a three-story apartment building with about six units per floor. We, my parents and I, live on the third floor and two doors down is Mrs. Brown and her ten-year-old son Brad. There is no Mr. Brown around for some reason or another. In any case, one day after talking with my parents Mrs. Brown asked me to babysit her son. Apparently she was going to have her first date in years next Friday. Since I my parents are really strict about me being out past 7:30 on any night, I thought what the heck I might as well make a couple of bucks. Besides, it is really hard to turn down a hot babe like Mrs. Brown. I sometimes masturbate fantasizing about her.

Well Friday comes and I go down the hall to start my first babysitting job. In fact being only 18 years old this is actually my first job period. Mrs. Brown gives me her cell phone number, shows me where everything is and gives me a list of instructions.

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   In particular Brad is to have a bath before bedtime.

Brad's bedtime is eight o'clock so about eight thirty I start to get after him to have his bath. Twenty minutes later he is in the tub. After watching TV for half an hour I decide Brad has been in the tub long enough. On the way I looked in Mrs. Brown's bedroom and imagined her laying on her bed in a see-through nightie. I wondered if she actually has such a thing. Then I saw her dresser bureau and thought why not find out. Brad is going to be busy for a while yet so I started to search in the drawers. Beginning at the bottom and working my way up I didn't find any nighties but in the wide top drawer were all her bras and panties.

Not wanting to disturb anything I reached out and lightly touched then softly stroked a bra with a trembling hand. It was a plain white nylon one smooth to the touch. Almost instantly I had a hard on When I moved on to touching Mrs. Brown's panties I began to rub myself through my jeans. I picked it up and stroked the panties over my face.


   I loved the silky smooth feel of it. They had a laundry clean smell which disappointed me since I wanted a whiff of Mrs. Brown's scent. Placing the panties back I realized I had better get Brad out of the tub and to bed. Besides, I could come back when he goes to sleep and not worry about him finding me whacking off to his mother's underwear.

The bathroom door was closed but not completely shut so I pushed it open slight just to peep in on Brad before calling him. To my surprise he was already out of the tub but that is not why I was surprised. Perhaps a better word would be to say I was shocked. Brad was standing naked, facing sideways to the huge wall mirror over the vanity. He was looking at himself while he slowly rubbed his hands down his chest, over the belly, down around to his bum then up to his chest again. What really jolted me was that he obviously was staring at his own hard on Each time his hands came down to his hips they would get closer and closer to his cock. He was teasing himself. For a ten-year-old kid he seemed rather experienced at getting himself aroused.

Finally he began to lightly touch, stroke and fondle his cock with his finger tips. The other hand gently stroked one cheek of his bum.

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   He stroked his ass, gradually doing it harder and harder until finally he grabbed himself hard. When he repeated this pattern I could see red finger marks on his pale white ass. I could see in the mirror that now Brad's eyes were closed and he was holding but not stroking his dick.

It was at this point that I realized to my utter horror that I have a raging hard on I couldn't believe myself. Watching a ten-year-old kid masturbate had me so hard that my balls began to mildly ache. Kept saying to myself "I'm not gay! This has never happened before. Not gay! I don't believe this. NOT!" Yet there was no denying that I was nearly ready to cream myself. While I was feeling the confusion and guilt of the my arousal Brad did something that pushed me over the edge of self control.

He began to run his middle finger up and down the crack of his ass. He would wiggle the finger making it go deeper into his crack. Then his hand stopped moving but his finger was still moving rhythmically. I couldn't see most of the finger but I just knew that he was fingering his asshole. That is a totally awesome, strange thing to do to yourself.

Suddenly Brad stops and turns to see me in the mirror.

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   Must have made some sound to get his attention. I was certainly trembling with sexual excitement. He steps back a few feet as I come into the bathroom saying, "It's cool man. " He is obviously scared, and afraid he is in some kind of trouble. Trying to reassure him that nothing is wrong and to calm him I tell him, "I like to jerk off too. Often. Every guy in the world masturbates. So don't worry you are not in any sort of trouble. You're cool. " While I am saying all this I stripped off my T-shirt, shorts and underwear. "See I got a hard on too. I was actually planning on whacking off myself, after you went to bed. "

Now we are both staring at each other's cock. Despite his anxiety with the situation Brad still had a hard on His dick was standing straight up, I mean vertically. His balls were two little marbles at the base of his shaft.

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   There was not a hint of pubic hair on his pale white crotch. Brad's eyes are wide open and totally focused on my cock. "Have you ever seen another guys cock hard before?" I ask him. He nods yes. I don't really pay any attention to his respond because I’m completely confused about my own feelings. After all here I am naked with a hard on in front of a ten year old boy. This is a whole new situation than I have ever experienced before.

On the one hand, I want in the worst way to bang my cock against his tiny body. But then on the other it is absolutely the wrong thing to do for all kinds of reasons. For one thing I am not gay and have never done anything sexual with a guy ever. Two, he is only a little kid with not a clue as to what is really going on here. Being the older one, in fact the babysitter, I should know and do the right thing. But the self control of a 18-year-old boy is not enough to overcome being aroused twice in five minutes. Once with Mrs. Brown's underwear then again while watching Brad feel himself up and masturbate.

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The next thing I know instinct is taking over. I don’t want to but I step toward Brad and reach out to take hold of the sides of his chest. He puts his hands on my chest but I ignore it. Stepping still closer I spread my feet apart and bend me knees to lower myself so I can touch his cock with mine. He tries to push me away but I’m too strong for him.

Shoving my hips forward does me no good because he arches his back to move his hips away from me. I encircle him in my arms but still I can’t make satisfying contact. Leaning my weight forward, I shove Brad up against the wall. Now I can press on him but he won’t stay still. Clearly not liking this he starts to whimper but I can’t stop myself. My body is literally in control while I'm thinking “No. Shouldn't do this. Can't do it. ” We are basically wrestling on our feet with Brad twisting and wiggling all over the place. In an effort to stop his convoluting hips I slip my hands down to his hips.

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   He is so small that my finger tips are at the crack of his ass and the heel of my hands are on his hips.

Suddenly Brad is motionless not resisting me at all. Even his whimpering has stopped. Puzzled by this I’m none-the-less glad to be able to rub my cock on his for more than a second. Then Brad startles me by tentatively putting his arms around me. This makes me pause. What is going on with him? He stopped fighting me as soon as I took a hold of his ass. Now it dawns on me how he fondled his bum more than his cock when I watched him earlier. The kid has a weird buttocks fetish of some kind.

“If that’s what turns you on. ” I thought, “That’s fine by me. ” So I began to stroke his ass with both hands, up and down, in circles and tracing his crack with my finger tips. I found myself rather enjoying the sensation of his perfectly smooth skin. When I began fondling his bum Brad remained absolutely still but now his hips began to undulate slowly, tentatively at first. In less than a minute he was humping me like a dog.

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   The next thing I know Brad’s thrusting has turned into a full body spasm. This scared me until I came to the shocking realization that he was having an orgasm. I never thought a ten-year-old boy could cum so hard or at all for that matter.

As soon as I understood he was having an orgasm I started to cum too. I could feel his little dick rubbing on the side of my cock. We were both so hard our cocks couldn’t move sideways. Pulling on his ass hard I could not press him against me any more. In seconds I felt a warm, wet sensation spreading on my tummy and cock. My cum was lubricating us, making him feel slippery smooth. I came so hard, for so long I could feel spunk running down the inside of my leg.

Gradually my frantic thrusting subsided enough that I became aware of the world again. Brad had finished his orgasm but each time I squeezed his bum he would do another quick spasm. This would cause me to have a short shuddering spasm as well. Finally, we were both completely spent, breathing heavy and drenched in sweat. We let go of each other and stepped back.

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   I reached down and fondled his little pecker, rubbing and spreading my cum all over his balls and cock until he shrank to almost nothing in size.

While I’m doing this I say, “That was sooo cool! I really liked that. I hope your Mom asks me to babysit you again. ”

“Me too!” he says.

Sure enough a month later Mrs. Brown has me babysitting Brad again. Over the next few months she began dating regularly three or four times a month. During this time Brad and I got more into having sex with each other. Oddly enough, despite the considerable pleasure I got with Brad I had no desire to seek sex with other boys. In fact, I still had a major crush on Mrs. Brown and liked girls in general.

So the next time was a repeat of the first time. I played with Mrs. B's underwear while waiting for Brad to finish his bath. When I peeked in on him this time he was doing the same thing to himself.

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   He knew I was there but pretended to not notice. I stepped into the bathroom and began to undress slowly while he continued to caress himself. The rest was the same as the first time except Brad did not resist me.

Each time I babysat Brad we did something a little differently. One night I began undressing in Mrs. B's bedroom before fondling her underwear. Then there was the first time we didn't do it cock to cock. I was staring at Brad's bum, really enjoying watching rub his ass, leaving red marks it. There is something about his pale white skin and the round firmness of his bum that I found rather arousing. As I approached him he began to turn around but I grabbed his hips and stopped him. Stepping up to him I spread my feet apart and bent my knees to lower myself. Then I touched his ass with my stiff cock. Softly stroking my cock all over his ass I got so aroused I actually felt light headed. Reaching around I took hold of Brad's little dick and began to whack him off as I pressed my dick against his ass. He started cumming almost right away.


   His jerking spasms thrust his ass against my cock and in no time I was shooting spunk on his back.

This was our favourite thing for awhile. Brad would spread his cheeks and I would finger his asshole with the tip of my cock. Then I humped him with my cock between his cheeks. I never did have anal sex with him but I did finger fuck his hole when we had frontal sex. Brad loved anal stimulation. So much so that he sometimes bent over and asked me to finger fuck his hole but not touch him in any other way. In the beginning it would hurt him but he would not let that stop me. In a weird way he actually liked the pain. It was not long before I learnt to make circles with my finger as I pushed it in. In this was I could get my finger all the way into him. Eventually we used my cum or baby oil as a lubricant.

This “ass” thing Brad struck me as rather weird. So one day I asked him about it, “You seem to get off with your ass more than your dick. What's that all about? When or how did it start?”

He looked down at the floor and after a moment or two said in a soft voice, “It started when I was seven and stopped a couple of years later when my Father left us.

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  ” This did not make a whole lot of sense to me. He saw the confused look on my face and explained further. It turns out his Father liked to feel his ass and would sometimes press his cock somewhere on his body as he did it. He even liked to have a pee while Brad was naked in the bathtub. Brad said he could see his Father getting an erection as he looked him over. Apparently this was the only way Brad ever got his Dad's full attention. It made him feel creepy and some how dirty but it was the price he reluctantly paid for his Dad's affection.

About six months before he disappeared his Father began to do just what Brad and I did the very first time. That is he would grab Brad by the ass and grind his hard cock on Brad's tiny dick until he came. He never had any intention of this being a pleasant experience for Brad too. It was just about him getting his rocks off. Brad's Father would do this once or twice a week, always with their clothes on. Sometimes his Father pulled him on top of him when they were in pyjamas watching TV, in the pool or in the garage. Where and when ever it happened his Father always held and stroked his buttocks as he pumped his cock on him.

Seems to me Brad was being raped rather frequently with impunity.


   So I asked, “Did you ever tell your Mom about not?”, I asked.

“Because she knew all about it. She saw my Dad and I doing it. Often. ”

“Oh. ” was all I could think to say. Brad's story seem to explain a lot of things but it raised a few other questions for me but I did not want to pursue them.

Anyway, our sexual activity continue to evolve over time. One night Brad catch me in his Mom's underwear drawer. That's when I got him to put on a pair of his Mom's panties. He did not want to a first but I persuaded him it would be fun. Then I got him to lay on the floor and got on top of him. The fact that we were in Mrs. B's bedroom really turned me on. As odd as this may sound, what gave me a massive orgasm was the thought that I was fucking Mrs.

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   Brown's panties.

Next time I got Brad to wear his Mom's bra as well. It was a padded one so it felt like he actually had breasts. This time we got on Mrs. B's bed. Before mounting Brad I ran my hand all over his body. Slowly stroking his soft skin, feeling his “cunt” and “breasts”. I even licked his “breasts”. By the time I got on top of him I was completely into the fantasy of fucking his Mother. I swear I lost consciousness of a while.

By the third time we did this Brad was beginning to enjoy wearing his Mom's underwear. It certainly was a major turn on for me. I kissed Brad (Mrs. B) this time. Odd as it seems this was our first kiss but it certainly wasn't the last one.

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   At some point I started to put my cock between Brad's legs and had him squeeze them together so I could pretend to fuck his Mother's “cunt”. Of course I never told Brad I was fantasizing having sex with his Mom.

Two years later it is my sixteenth birthday, Brad is almost twelve. In all that time we never once sucked each other's cock. We humped, banged, whacked each other, fingered, fondled and groped but never did blow jobs. Since it was my birthday I thought it would be a nice present for me and I figured it was about time we did it anyway. Brad absolutely refused to put my cock in his mouth yet alone suck it. Nothing I said or did could get him to consent.

So I asked him for the second half of my birthday present, to suck him off. He was starting to produce some spunk and I wanted to find out what it tasted like. Again he refused. He gave no reason, just something that didn't turn him on. In fact, he said it was a dirty, disgusting idea. Well by now I am a little peeved and randy as hell. So I pushed him onto his bed, sat on his chest and leaned on his legs with my forearms.

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   He was trying hard to buck me off but my weight and strength kept him pinned down.

His cock was limp and tiny when I started to lick it. Usually any kind of fondling would get him hard in a matter of seconds but not this time. So took hold of his dick and balls with my lips and without sucking, pulled on them. While doing this I flicked his pecker back and forth with my tongue. Still no response so I finally started sucking him, dick and balls at the same time. I rather liked the feel of his small, soft cock on my tongue. As I pushed bean sized testicles around he began to stiffen up. Slowly it grew further and further into my mouth until it started to enter my throat. I had a small gag reflex but controlled it. Breathing like that was not easy so I pulled back a bit and let his balls drop out of my mouth. After this it was a straight ahead suck with my tongue licking and pushing on a hard penis.

Then I got my birthday surprise. Brad began to lick my balls. A few seconds of this and I was shooting cum all over his chest and belly.

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   I held his cock in one long hard suck. Essentially I stopped breathing as the orgasm took over. Next thing I'm conscious of is Brad thrusting his cock into my throat. It was spitting cum directly down my throat. I swallowed it but never tasted it that time. No matter, it was great to at last feel a hard cock in my mouth as Brad's body spasmed out of control.

When I finally rolled off of Brad I got another birthday surprise. Actually, it was more like the shock of a lifetime. Mrs. Brown was standing beside the bed and what' more . . . . Well that's a whole other story by itself to be told another time. I will tell you however that neither of our lives were ever the same after that.

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