Babysitting Boys 2
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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Susan, 61

I was way too young when I started babysitting, barely twelve-years-old. We lived in a rural area and girls were expected to contribute. The family I babysat for had three children in the pre-school to first grade range, two girls and one boy.

Harry the youngster always fussed about taking his bath with his sisters, so I started with them first, then took care of Harry alone. Although I was at the onset of puberty, I had not seen a penis yet in my life. Living on a farm, having no brothers and a father who always shut the bathroom door, there had never been a single occasion to catch a glimpse of the mysterious male appendage.

Bathing Harry finally allowed me to get a good look at a boy's privates, albeit the miniature version. The tyke's attention was focused on his toys in the water. I could wash his genitals as much as I wanted. The smooth little bag of testicles and tiny shrunken tube of pink flesh fascinated me.

One evening, I washed Harry's behind longer than usual. His penis stiffened and got bigger. Then, it deflated after a minute. I soaped up my fingers and washed his butt crack again, rubbing his hole, curious to see his wee-wee get hard. When I stopped, the little thing softened. Since Harry was playing with toys and could not care less about what I was doing, I rubbed his anus again and again, almost obsessed by his erections.

From then on, I did it every time I babysat, sometimes, for ten minutes straight. When Harry got out of the tub, he was without a doubt, the little boy with the cleanest bottom in the world.


Ronald, 37

Jeremy was my cousin of sorts. His mother had recently married my cousin which made him some sort of relation to me. I couldn't figure it out without the help of a family tree. Not that I really cared. At thirteen, five bucks an hour for keeping an eye on him wasn't a bad deal, especially since I would have been ordered to do it without being paid. Jeremy was nine-years-old, so I figured he was past the state of sticking random things in his mouth. Easy money for me.

After his parents left we turned on the video game console. This was back when the PS2 was on its way out with the vibrating controllers. We started playing a game together, I don't remember which one. Lots of explosions. I was sitting on the couch which was at a 90-degree angle to the TV while he was sitting on the floor legs crossed, the controller in his lap. After a particularly long explosion, I noticed Jeremy repositioned himself, going from sitting up to stretched on his belly. I didn't think anything much of it.

He was propped up on his elbows and it was only when he started to move back and forth that I really noticed. I asked him what he was doing, and he gave me that deer-in-the-headlights look. Even though I was thirteen I didn't make the connection. About a minute later, he repositioned himself again this time moving back a little more and wrapping his legs around the coffee table's leg. The table legs were the fancy types that look like little spheres on top of each other. His arms on top of the table, still holding the controller, he started to raise himself up and then back down. "If you keep doing that you're going to loosen the leg!" I remarked.

Jeremy shot me a rather annoyed look. Irritated, he stood up and laid down on the couch next to me, his head almost touching my knee. We went back to playing and this time I noticed he was grinding his hips against the cushions, well, right in the gap between two of them. I understood now what was going on.

Pausing the game, I looked down at him and asked point-blank if his pee-pee was hard. The way his face went pale, you would have thought I had accused him of murder. To make a long story short, his mother had basically scolded him into feeling embarrassed about it. Now to be fair, my parents had never told me anything about it, but I knew. Well, at least as much as anyone at that age. So, I swore him to secrecy and told him how he could make it go down.

I guess he appreciated the straightforward talk because he didn't have any problem raising his shirt up and pulling his pants down. I will admit he was cute. His stomach was a little brown from the summer that had just ended. I don't know if his penis was particularly big or small for his age, but it was uncut which was a novelty for me. Leaning in for a closer look caused him to laugh and point out that I was getting hard too. So, with my toe already in the water I decided to jump in.

My pants came down and of course, he wanted to know about the hair. The two of us jerked off together. I washed up we went back to playing the game. It became a thing for us for a while. I was his favorite babysitter. I wouldn't say we were particularly close at that time, more like partners in crime.

It wasn't until two years later when I was surfing around on some chat website looking for someone to jerk off with, that I was randomly connected to a group of four boys having a sleepover. It took me a second to recognize my cousin and I think it took him a few more seconds to recognize me. He was a bit in the background not the one in charge, but they all wanted to do dares. That was fun. That's another story though.


Robert, 56

I was raised during a period when spanking was common and not considered child abuse. My dad spanked me from the toddler years all the way to twelve-years-old. It happened usually on my bed. He pinned me with his hand on my back, face down on the mattress. Then he bared my butt and walloped my buns with all his strength.

His `corrections' were always rigorous, the type that made you squirm, beg for mercy and promise never to do again the bad thing you had done. The type that made your ass glow scarlet and cry in your pillow. Since I was a disobedient and clumsy boy, it happened quite often.

Being an unruly kid assuredly also made the job of my babysitter a nightmare. She handled it very well. Looking back, it amazes me that she could keep her calm and find the right words to control me. She was definitely a smart teenage girl with a good heart.

When I turned ten-years-old, my nastiness went up another level. One evening, after I had been particularly rude to her, she lost it and said:

"That's it! Robert, I'm going tell your parents that you were very bad tonight."

"Please no," I cried out, suddenly scared. "My dad's gonna spank me!"

"Well, I have to. You must learn to behave."

"Oh no, please, please," I insisted on the verge of sobbing.

Seeing the genuine fright in my eyes, she proposed something that came as a great relief. She offered to spank me. Twenty strokes to punish me for the awful way I had treated her. I accepted immediately, knowing she would not beat my butt with as much force as my father.

I remember every details of those three minutes. I was wearing plaid pjs pants and she quickly had them down around my ankles as I climbed on her lap. Then, she extended her arm and stole a slipper off my feet. The kind with a rigid rubber sole. Swoosh, she started hitting my butt. Smack on one buttock, smack on the other, then -smack- -smack-, twice on the same spot.

At ten-years-old, I had a bony ass. It was more painful than I had anticipated. Staying still in her lap, grimacing, I yelped every time the sting shot up my spine. But another sensation also spread in my body, that of sexual excitement. I found it utterly arousing to be spanked by a girl, especially because she was spanking me with my own slipper.

After the twentieth stroke on my little butt, I was flustered and near getting an orgasm. I leaped back on my feet and pulled up my pj pants as fast as I could. Not fast enough for her not to notice my stiffy. "Urgh, you're such a little pervert, Robert." she said.

She was right.


Jeffery, 30

When I was twelve-years-old, my parents got a new teenage babysitter for me, the last one. She was called Tina and she was incompetent.

As soon as my parents left, Tina let in the house her boyfriend of the moment, making me promise not to tell. They went to the basement and made out on the couch all evening, as if I didn't exist. I was a solitary boy with glasses who enjoyed reading, but I still expected a babysitter to give me a bit of attention. To spite her, I stayed in the basement with them and tried to disrupt whatever they were doing.

Around nine p.m. Tina always turned to me and said something like "Maybe you should go to your room, get ready for bed now, uh Jeffery?"

I knew exactly what was going on, because I'd heard it before and would every time. I left the room, counted to 100 and returned to sit on the first carpeted step of the stairs that went down to the basement. Usually, Tina's boyfriend of the moment was already naked from the waist down with a hard-on. What happened next was educational.

Tina was sixteen and she dated only jocks that were a bit older. They were all horny and muscular. It stunned me to see how big their cocks were. One Latino dude surely had a ten-incher. Tina grabbed their cocks and went down on it, moaning and obviously enjoying it. Then, they got aggressive verbally saying things like "Yeah, suck my cock, slut."

Tina was a pretty girl with long blond hair and a petite frame. She couldn't impede their lust. They used to grab her by the hair and shove their huge erections down her throat, looking down at her like she was a piece of garbage. She gagged, tried to get away, but they pulled on her hair and crammed their cocks again down her throat yelling, "Don't back away bitch, it's all for you, suck it, yeah, be a good girl, that's it, take it all."

Looking at this live pornography at the top of the stairs, I pulled my shorts and undies down, and masturbated. Both knew very well I was there, spying. Sometimes, I'd see them glance my way, then ignore me, unconcerned about doing it in front of a geeky twelve-year-old boy.

After a while, Tina fished out a condom from her purse and unrolled it on their cocks. It took these horny jocks about three seconds to take off Tina's panties and tee-shirt, exposing her tits. They grabbed both her legs and leaned into her. Right away, they started fucking her energetically.

Sitting on the top stair, I tugged on my boner, carefully making sure I didn't cum too fast. My eyes were glued on the teen couple as they fucked and groaned with more unbridled lust. I liked that my slutty babysitter was vocal. She squealed and yelled, "Ohhh yess! Fuck me! Ooooooh yes, YES YES!"

Tina surely had many orgasms because I could hear her whimper and become woozy from time to time. When I could not hold back anymore, my hand flew on my boner until a nice cum shook me from head to toes.

I don't believe being exposed to this much raw sexual intercourse at a young age affected me. Then again, I sure love getting fucked by a young stud and being called a slut.


Andrew, 29

I always had praises for Kevin when my parents asked me about my babysitter. I was nine-years-old, a skinny and outgoing kid with blond hair and restless little legs. Having a boy for a babysitter certainly was ideal for me. Kevin was fourteen and very much masculine like me. He attended the cadets and was fascinated by army stuff. I never saw him without his pair of camouflage pants.

The games we played included a lot of pretend violence and imaginary blood. We chased each other in the house with plastic guns and performed slow motion fist fights. Kevin also often `tortured' me. He tied me up on a chair and applied methods to make me talk, which were of course, pinching and tickling. I truly enjoyed the company of the wild teenager. Kevin was a rather handsome boy despite the pimples. He had dark hair, an athletic body and a coy smile.

After a while, Kevin introduced a new game I enjoyed a lot. He would tell me I was his prisoner and he would push me into a cell (the closet in my bedroom). There, he would tie my wrists together then around the pole holding my clothes. "I have to do a full body search." he'd announced while patting me all over. Giggling, I could already feel my little penis stiffen from his touching. The next minute, he would lower my shorts then my undies, continuing to seek on my exposed body something hidden that did not exist.

By then, I had a rigid boner, being half-naked and restrained in my closet. This was the naughtiest thing in my nine-year-old mind. Especially, because Kevin would start to masturbate me. The pleasure I felt at that moment was exhilarating. The next level came when he stuck his wet index finger in my butt hole and fingered me. It didn't take long before I yelped and got a dry cum.

I liked this game a lot and we played it many times. Then one day, he put something else in my butt hole. The pain had me screeching and turning my head around. His camouflage pants were down. I saw his big penis between my little buns. "Ugghh, Kevin! It hurts!" I cried out.

"Wait a bit, it will feel good," he said, pulling on my tiny prick fast and steady to make me forget I had his hard dick thrusting in my behind. For a couple of minutes, I winced, getting fucked and jerked at the same time. When he came, holding me tight and pumping his load inside me, I had the biggest orgasm yet and cried out of joy.

From that point on, Kevin continued to be my babysitter for about ten months. And I was a very happy little boy. 

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