Babysitting Boys
by Dick Drewl

This is a collection of testimonies based on true events but largely embellished with fiction. Names were changed to preserve confidentiality. This file contains explicit text of a sexual nature with minors. If it is illegal in your country, or you find this sort of work offensive, do not download it or read it.

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Jason, 34

When I reached fourteen, my parents decided I was old enough to take care of my two little brothers. I felt proud and mature. Then I realized it came with a responsibility as my dad shouted going out the door, "Make sure they don't burn the house down!"

It wasn't an exaggeration. My brothers were rambunctious seven-year-old twins. They were not identical but almost. Both were thin and had crew cuts, scrapes and bruises on their legs. They romped around the house in white briefs, screaming, climbing on furniture and breaking things. They were the type of kids you admonish constantly and scream at, "No! Don't do that!"

I quickly lost control of the hyperactive little monsters. Thankfully, I came up with a game to occupy them for a while and consume their energy. It was a game of dares exploiting the natural rivalry between them. I wrote challenges on a little piece of paper and put it in a Ziploc bag. It contained challenges like:

`Stay on one foot for as long as you can'
`Draw numbers on each other's back that you have to guess'
`Wrestle each other until you pin the other's shoulders to the floor'

The twins liked this game, especially when there was physical contact. They giggled and got stiffies tenting the front of their tighty whities. Seeing this, I introduced racier challenges to entertain myself too. Things like:

`Spank each other's bare butt 5 times'
`Kiss each other on the mouth'
`Lick syrup out of your brother's belly button'

I also put in the bag `Put your brother's penis in your mouth and suck it 30 seconds'. Added a few of those so that it came out at least once! Sometimes, one brother would say "I'm not doing THAT!" Immediately, the other would raise his arm and announce excitedly "Ooh, I'll do it!" then the other would snap back, "Then I'll do it too!"

It was a quite a show every time I babysat. My brothers did absolutely everything I wrote on those little pieces of paper. Oh yes, everything.

Michelle, 50

Like a lot of teenage girls I did some babysitting in the neighbourhood to earn extra pocket money. It was something I enjoyed because I knew I wanted to have children.

The kids were nice to me since I was motherly with them but not that strict. A nine-year-old boy named Jimmy liked me for another reason. I was already busty back then and he couldn't stop staring at my boobs. He also hugged me a lot and got handsy. I didn't know how to deal with this and just ignored his obvious attraction to me.

One evening, I noticed Jimmy had been in the tub for more than fifteen minutes. So, I went to check on him and opened the bathroom door (never locked cuz' you don't want a kid drowning on your watch!) I should have expected it but didn't. The little boy was masturbating. He was going at it, well, passionately! He must have been about to climax because his naked little body was all tensed up and his feet curved inward.

It took a few seconds before Jimmy realized I was there. The look of shock on his freckled face was memorable, eyes big as saucers, mouth wide open. Quickly, he covered his privates with both hands. To be honest, I was more embarrassed than him. I blushed and started blabbering, "I'm I'm sorry! Didn't think, erh, you were-"

Then I shut the door, somehow convinced he had been thinking about me while he was doing it.

After that, I saw more than my fair share of teenage boys and men jerk off. They were never as cute as Jimmy.

Christopher, 41

At nineteen, I used to babysit my cousins occasionally. I didn't mind doing it because they were low maintenance boys. Matthew was twelve and his little brother Jonathan, eight. We played video games and board games. We got along well. They obeyed the rules and went to bed as scheduled without making a fuss.

The bedroom they shared was upstairs. I escorted them. They put on their pajamas naked in front of each other and me. Even though Matthew was twelve, he was still prepubescent and hairless, so I figured he didn't care yet about modesty. When they slipped under the covers, I went back down to watch TV, happy my job done was done, except for random security rounds.

About the fifth time I babysat my cousins, when I went to check if they were asleep, the bedroom door was close, which was unusual. I approached and heard some moving around. Then, a mattress started creaking. I listened closely.

- Unngh, it hurts! Jonathan whined.
- Shhh, he's gonna hear us! Matthew whispered. Open your hole...
- I can't!
- Wait, I'll spit on it.
- Unngh, unnggh!
- See, I told you it would go in, Matthew rejoiced, keep holding your buttocks!

For the next minute, I heard almost nothing, some heavy breathing and the springs of the mattress squeaking a bit. My heart was racing. You didn't have to be a genius to figure out what they were doing, and for sure, it was the first time. I didn't know what to do. The idea of bursting in on them and having to explain what I had seen to their parents made me cringe. It didn't sound like Jonathan was resisting. So, I let my hard-on take the decision and continued to eavesdrop.

Their fuck noises got a bit louder after a while. I started to hear Jonathan's little butt get smacked when his brother thrust into him.

- Unngh, Matthew, unnggh! He moaned, trying his best to keep his shrill voice down.
- Do you like it? Matthew asked.
- Yes, kinda.
- Okay, I'm gonna do it faster, now. Orhh yes, orrhh!
- Ungh! Ungh! Ungh!

With my hand down my pants stroking my hard cock, I stayed behind the closed door the whole time, listening to my pre-teen cousin take his little brother's cherry. It lasted about ten minutes. My cousins were assuredly the two kids I'd least expect to have sex together. They were both polite, blond golden boys that got good grades. The goody-goody image I'd built of them vanished. There was definitely some unbridled butt banging going on behind that door.

Jonathan squealed and Matthew let out a sign of joy. Then, everything went silent. I'd already cum and had to spend the rest of the evening watching TV in slimy wet underwear.

Norman, 62

During my college years, I lived in an apartment building. There was a young mother next door, a stewardess. When she had to stay overseas, she dropped her six-year-old son off at my place, thanking me a million times.

I liked the kid a lot. Simon was an adorable redhead with a gap-toothed grin. The boy was playful, funny and a bit mischievous. After his bath, he climbed into bed wearing colorful pajama pants and suggested, "I wanna play the dead game!"

It was a game that I also enjoyed as a kid. The rules are simple. While one child is pretending to be dead the other subjects him or her to all sorts of mild physical torture. If the `dead' kid flinches, giggles or anything, he or she loses the game.

Simon took this game seriously, keeping his eyes shut and his body limp. He stayed inert as a corpse while I tickled his armpits, rubbed his nipples and suckled his toes. He didn't emit a peep when I took off his pajama pants.

It was an interesting situation because the game allowed me to touch his small naked body as much as I pleased. While I massaged his shoulders, I kissed him all over his freckled face then went down to his belly. I kissed his dick and gobbled up his testicles. At that point, Simon's chest heaved and his little penis stood up, betraying his sexual excitement. He shut his eyes tight and bit his lower lip, ensuring he would not make a sound that would stop the game.

I grabbed his ankles and swung his short legs over his head to bend him in two. Simon almost lost it there knowing what I would do. I kissed his buns and slid my tongue between his pale globes. His butt hole contracted each time I swiped my tongue over it. Simon had to supress his squeals very hard when I began teasing the pink bud, darting the tip of my tongue at it. Then I slobbered all over it. It was the thing that turned me on the most, licking a little boy's anus. I always rimmed his cute pucker until it was relaxed and slightly open.

By then Simon's tiny circumcised dick was very stiff. It didn't take long for him to climax when I put it in my mouth. I sucked the little piece of vibrant flesh for about a minute before he got off. Simon shuddered and let out a yelp, followed by giggles. The game was over, for that evening.

Josh, 24

Because of my inability to find a summer job, my mom enrolled me in the babysitting club. I was sixteen-years-old and thought it was the lamest thing, even though it paid well. The prospect of wasting my evenings with snotty kids instead of chasing girls bummed me out. But I went with it.

The club was made up of a bunch of nerdy teenage girls except for one other guy. They assigned us two dudes all the boys because as they put it, "Boys are gross and never listen." It suited me fine. I knew that boys were a lot easier to entertain.

Much to my surprise, I got a lot more gigs than I ever anticipated. Our neighbourhood was in the upper part of middle class which meant they could afford a babysitter easily. For two years, I spent two or three evenings in another family's home every week.

The younger kids were turbulent and hard to handle. The older ones were more into video games. And soon I found out, they were also into talking about sex, mostly porno things they had seen on the internet. At eleven and twelve, some of them were at the early beginnings of puberty and were obsessed by sex. I got a lot of questions on penis size, sexual orientation and masturbation. They also asked me bluntly, "Do you have big dick? Show me, like just five seconds..."

It didn't shock me. I practiced a lot of sports as a teenager and always wore those horrible blue track suit pants that give you a bulge at the front. They were just curious about it. Being a dumb teenager who had sent many dick pics to girls from school, I didn't even think for a second that there was anything inappropriate with waving my hairy pecker in front of children. I pulled my sports pants and undies down, letting them have a good look.

Now I won't go into the details of two years of interactions, but with time as we got to know each other better, things turned from talk to action. I jerked off with at least eight little boys who wanted to see me squirt. Out of those eight, I also had mutual oral sex on a regular basis with four of them. One twelve-year-old boy was very good at it and swallowed my load every time. He had done it with his older cousins.

I think the other dude in the club also fooled around with the kids. Whenever I bumped into him we talked about babysitting. It was the only thing we had in common. One time, he disclosed something that was as good as admitting it. "My favorite is Tyler, he's well behaved and very very friendly." He said and winked.

Two boys asked me to try anal sex. This confounded me because none of my girlfriends ever wanted to do that. One boy definitely didn't like it. The other enjoyed it. His name was Connor and he was eleven-years-old. Looking at him, you would think he was just another innocent boy. The kid was skinny with a soft narrow face, short blond hair parted to the side. He smiled grandly, smelled of bubble gum and never said a dirty word. But when we fooled around naked, he always raised his behind at me and said "My butt is horny." It didn't make sense, but the message was clear. 

I used to babysit Connor about twice a month and had anal sex with him every time. At first, there was a lot of wincing and squealing when I pushed my dickhead into his small butt hole. But when it passed the sphincter, Connor let out a long sigh and loosened up. At sixteen, my cock was already full grown, seven inches long when hard and thick. It amazed me that he could take it in the ass so well.

I purchased chocolate laxative and a big tube of lube to make things easier for him. The more we did it, the more Connor got into it. I fucked him doggy style, on his bed. This is how Connor liked it. He moaned the whole time, "Annngh, yesss, annngh, annngh!"

I started gently, holding his slim waist, pulling back when he let out a yelp of pain. After a while, Connor pushed his bottom back on my hard-on while I thrust into him. We both groaned and moaned, especially when my cock went balls deep into his hole. From then on, there was a whole lot of shaking going on. Connor was small for eleven and I was a horny teenager, so I couldn't help but do it fast and steady, wanting so much to cum inside him. To this day, I still can't believe that a little boy let me fuck his butt so hard.

After I left the babysitting club, I went back to dating girls. But once in a while, I see a good-looking guy and think that maybe we could have fun together.  

If you have a babysitting story you wish to share, true or fantasy, send it to ddrewl  (@_at) protonmail.com. Will do a second instalment if I get a bunch. Flames are ignored.