Babysitting

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 14 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. 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 hardon 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 hardon 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. 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 

hardon 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. 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 hardon 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 th

e situation Brad still had a hardon His dick was standing straight up, I mean vertically. His balls were two little marbles at the base of his shaft. 

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 hardon 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 tin

y 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 14-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.

 

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. 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. 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. 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. 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.” 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 this?”

 

“No.”

 

“Why 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. 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. 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. 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. 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.