Chris Hailey's stories | Guest authors | Contact the author



It was a few days after Dylan and I sucked each other in the old storage shed at the back of the park when Dad made me go with him to the lumber yard. It wasn’t until we got there that I understood why Dad wanted me to come with him: he was buying insulation board. While the rigid foam was far from heavy; it was awkward as hell to move.

Anyway, when we were driving home we went past the Wieners’ house. There was a ‘for sale’ sign in the front yard. For the first few seconds after seeing it I didn’t really find it troubling in any way. Then, as we pulled into our driveway I realized how that ‘for sale’ sign was going to affect me: it meant I wouldn’t be babysitting Cami and Tara again. Considering the game of ‘doctor’ they had played with me: that really SUCKED! I couldn’t even begin to imagine how many other sex-things the three of us would have gotten to do if I had only gotten to babysit them more; or at the very least again…

After a couple hours of regretting not trying to do more with Cami and Tara, the phone rang. It was Mrs. Watkins: she wanted me to watch Ben and Joe that evening. I agreed without hesitation: not only were they well-mannered kids, and I was all but certain we’d end up spending the bulk of our time doing various sex things…and then of course there’s getting paid…

***

Per Mrs. Watkins’ instructions I arrived at their house at 6:30. Barely five minutes after getting there Mr. and Mrs. Watkins left: and so, it was just me and the two boys.

Not more than a minute after their parents left, Joe asked, “Can we play outside?”

For good or for bad, I hadn’t been given any instructions one way or the other about letting the boys play outside; so after a bit of quick thinking I suggested what seemed like an acceptable solution to letting them be outside while making sure nothing could happen to them. “We can go out into the backyard if you want,” I offered.

“Okay,” both boys said at the same time. A millisecond later they were running to the back door.

“Wait for me,” I commented as I headed in the same direction.

Little more than a minute later all three of us were in outside in the Watkins’ back yard.

In light of our previous activities, I was more than a little surprised when the Watkins boys headed straight to the swing-set. Once at the swing-set Ben immediately sat on one of the swings and began swinging. Joe really surprised me by turning and asking, “You gonna swing?” while standing in front of a second swing.

I wasn’t sure why he was asking, but figuring ‘what the hell’ I replied, “Yeah,” and walked over to the swing-set. I quickly planted my butt on the third swing.

Before I could even begin to rock the swing back, Joe stepped in front of me, smiled, and said, “I got an idea…”

“Okay…” I responded; despite having no idea what he was thinking.

A small fraction of a second after that one word passed my lips; Joe placed his hands on the bottom of his t-shirt and pulled it up and over his head, before tossing it onto a sun-lounger which was about ten feet from the end of the swing-set. He then moved his hands to the waistband of his shorts and pulled them, along with his underpants, down in one smooth movement. He stepped out of the shorts and underpants and promptly tossed them onto the sun-lounger with his shirt. Wearing only a pair of sneakers and socks, he said, “You gotta do the same.”

Despite the fact that I wasn’t all that concerned about the kids I was babysitting discussing the things we did while I was babysitting them, the idea of stripping down in front of them, in the backyard behind the house they lived in with their parents, who had hired me to watch them, did concern me. I quickly glanced around to find that the fence and large trees around the perimeter of the Watkins’ backyard provided the outdoor space complete privacy. No longer fearing that a neighbor would be able to see that I was naked with the two younger boys; I stood and pulled my t-shirt over my head. Before I could drop it or toss it anywhere; Joe’s hands were on it and he was taking it from me. Joe tossed my shirt onto the sun-lounger with his clothes as I hooked my thumbs in the waistband of my shorts and underpants, before promptly pulling them down, once my shorts and underpants got to my knees I let go of them and they fell onto my feet before I stepped out of them. Joe proceeded to bend down and pick up my shorts and underpants then toss them onto the sun-lounger with the other clothes. Now, wearing nothing but a pair of sneakers, I sat my bare butt on the swing.

“Don’t start swinging yet,” Joe quickly said.

“Okay,” I replied; more than a little bit confused.

I remained marginally confused when Joe turned so he was facing the same direction as me; when he proceeded to sit on my lap things started making a lot more sense. He wiggled around on my lap for several seconds: the warmth and softness of his bare butt cheeks combined with the friction of it moving around on my bare lap caused my dick to begin to harden.

“Lean back a little,” Joe suggested. As I leaned back he lifted his butt up off my lap a little and moved backwards: further up my body. Once my half-hard dick was below his crotch, he sat his butt down on my lower belly and spread his legs a few inches apart. He then proceeded to reach down between his thighs and took hold of my dick, which continued to harden in his hand. He lifted the head of my dick up until my shaft was in a vertical position before moving his legs back together: my almost fully hard dick was now held snugly between his thighs. He then slid his butt down my belly about an inch: stopping when his hairless nine-year-old balls were firmly pressed against the top of my dick.

It wasn’t until Joe leaned back, pressing his shoulders into my chest, that I was able to look over Joe’s shoulder and down the front of his naked body to see that his dick was fully hard and standing up straight, and that the tip of my dick was peaking up above his hairless balls from between his thighs.

“Can I get on too?” Ben asked.

Despite not being sure if he was asking me or his older brother, I replied, “Yea sure.”

As Ben was hopping off the other swing Joe commented, “You gotta do like I did.”

Ben quickly removed his shirt and shorts, and tossed them on the sun lounger with the other clothes. Wearing only socks and sneakers he climbed onto Joe’s lap. After a bit of wiggling, Ben was in the same position relative to Joe that Joe was in relative to me.

For a couple seconds we sat there silently and motionless on the swing.

“Now we swing,” Joe definitively said.

It took a few tries for the three of us to get into the same rhythm of leaning back then forward to get the swing moving and to keep it moving. Once we did though it was amazing: the movement of the swing combined with the leaning forwards and backwards of our bodies effectively generated a slow up-and-down movement of Joe’s thighs and balls on the shaft of my dick. The fact that Ben was sitting on his lap, created a bit of pressure on the tip of my dick on each ‘up’ movement.

We swung like that for about ten minutes before the up-and-down movement and pressure on the tip of my dick combined with the skin-on-skin sensation of Joe’s shoulders, back, butt, and thighs pressing against my chest, belly, lap, and legs pushed me to and then past the point of no return. I felt my butt cheeks tighten. In light of the movements necessary to continue swinging; I couldn’t force my hips forward and up to get more of my dick between Joe’s thighs, so I continued leaning backwards and forwards. My balls pulled up and I could feel the cum surging up the little tube on the underside of my dick. After a short fraction of a second the first spurt of hot, thick, sticky, creamy-white, sperm-laden cum shot out of the little hole at the tip of my thirteen-year-old dick.

“Wa-ouh…” Ben half gasped as that first spurt of my cum splattered against the back of his seven-year-old legs.

“Ah…woa…” Joe added almost immediately after his younger brother spoke.

Closing my eyes, I let the wave of pleasure surge through my body as the second spurt of hot, thick, sticky cum shot out of the little hole at the tip of my dick.

“It’s going on my balls,” Joe giggled as the third spurt blasted out of my dick.

“Neat…” Ben quipped.

Then, just as the fourth spurt of cum came rocketing out of the little hole at the tip of my dick, I felt Joe’s butt-cheeks tighten. “Oh…” he half groaned as his body tensed up.

Two more spurts of hot, thick, sticky, creamy-white, sperm-laden cum shot out of the little hole at the tip of my thirteen-year-old dick before Ben said, “Wow…” Glancing to the side slightly I noticed that his grip on the chain holding the swing had tightened significantly.

A seventh spurt of cum joined the first six. There was now so much cum on the back of Ben’s legs, the top of Joe’s balls, and insides of his thighs, that it was beginning to back up on the head of my dick.

After seven big spurts I would have expected my orgasm to die-down; but thanks to the continued swinging movements, the warm soft hairless skin which was wrapped around my dick, and the warm gooey wetness of the cum I’d already shot pooling around the head of my dick it didn’t. An eighth big spurt followed. Then a ninth spurt oozed out of the little hole at the tip of my dick…

Even though cum was no longer shooting out of my dick, my dick didn’t begin to soften at all. For the first time in my life, my dick remained fully hard after I had an orgasm. Beyond the fact that my dick was still hard, having the bare skin of Joe’s shoulders, back, butt, and thighs pressed against the bare skin of my chest, belly, lap, and legs felt quite good. So, I maintained the back-and-forth movements to keep us swinging.

It must have been a full ten minutes after my orgasm had ended when Ben asked, “Why are we still swinging?”

“It’s kinda fun…” I offered.

“Feels good too,” Joe added.

“Okay…” Ben said.

We continued swinging for another ten minutes in silence. It was then that we had to stop, “I gotta pee,” Joe informed us.

“That means we are getting off the swing,” I declared as I planted my feet in the dirt below the swing: bringing us to an immediate stop.

Ben hopped off Joe, then Joe hopped off me.

Just as I managed to stand up, Joe turned to the side and began to pee: the stream of yellow liquid spraying out of the little hole at the tip of his dick, arcing down and hitting the ground right next to the frame of the swing set.

Once Joe had finished peeing, I pointed towards his crotch region which was still coated in a layer of white goo and said, “You should clean it up before it dries.”

I’d barely finished speaking, before Ben stepped in front of his brother, squatted down, and began licking Joe’s cum coated balls.

Stepping over to the two brothers, I commented, “That’s good Ben, get it all clean.” Without taking my eyes off of my two charges, I took another couple steps to the sun-lounger which was covered in our clothes and sat down.

I watched with what I can only really describe as ‘about three-quarters interest’ as Ben licked all the cum off his brother’s balls and thighs. Once his brother’s balls and thighs were cum-free, Ben opened his lips wide and in a single motion, sucked Joe’s mostly hard dick into his mouth. I remained there, sitting on the sun-lounger and mostly watching Ben suck his big brother’s hard dick for quite some time.

Odd as it may seem, that sight was almost becoming boring; then Joe let out a low groan. I could almost feel my eyes double in size as I watched in a state of semi-stunned disbelief as Joe’s ten year old body snapped to a rigid attention. Were it not for the face that I was sitting at a nearly 90-degree angle relative to the Watkins brothers, I would not have gotten to see Joe’s butt-cheeks tighten and his hairless balls draw up at the same instant. Almost more amazing; as that was happening, Ben’s cheeks went from being decidedly convex, to almost impossibly concave at the same time his brother went rigid. For a brief second I wondered why Ben’s cheeks had changed like that, before realizing that he had started sucking much harder.

About thirty seconds after Joe’s body went rigid he gasped the word “whoa” before nearly falling over.

“That must have been something,” I heard my own voice say despite not realizing that I was speaking.

“Yea…” Joe began to stammer / pant as he leaned against the swing set, “…it…was…ho…man…”

Turning towards me Ben asked, “Want me to do that to you?” in a tone which oddly seemed to be completely lacking in emotion.

“Yea, sure,” I replied.

In little more than half a second, Ben was in front of me and my mostly hard dick was inside his mouth. For the first couple seconds my dick was in Ben’s seven-year-old mouth he was gently sucking: it felt pretty good but far from great. Then he surprised me by swirling his tongue around my dick: hat felt better…significantly better, but still not truly great.

He continued doing that for quite some time. Perhaps my perception of time was altered somewhat by the tongue swirling sucking he was giving my dick, because it seemed like he was doing that for a full half-hour. Going by the clock mounted on the wall near the barbecue, it only lasted for about ten minutes. Not exactly a short amount of time, but certainly less than half-an-hour.

Suddenly I felt my butt cheeks tighten. A small fraction of a second later I felt my balls begin to pull-up. In the exact instant my balls began to pull-up Ben began sucking so hard on my dick that, had I not been on right on the verge of an orgasm I probably would have feared he was going to suck the insides out of my dick. Less than a millisecond later I could feel the cum surging up the little tube on the underside of my dick. Almost at the same time, the first spurt of hot, thick, sticky, creamy-white, sperm-laden cum shot out of the little hole at the tip of my thirteen-year-old dick.

Considering how outrageously hard Ben was sucking on my dick, it was no surprise that the spurt of cum shot down his throat. What was surprising was his reaction to it: he stopped sucking and let out a decidedly stifled cough. Roughly a quarter of a second later he was once again sucking extremely hard on my dick.

The second spurt of cum shot out of the little hole at the tip of my dick and down Ben’s seven-year-old throat. Again he stopped sucking and let out a stifled cough, then a fraction of a second later was back to sucking.

That exact same process repeated for each of the six spurts of cum which came blasting out of my thirteen-year-old dick.

It wasn’t until my dick began softening that Ben stopped sucking. He parted his lips and stepped back: my rapidly softening dick fell from his mouth and smacked against my balls with a wet plop. As he stood he coughed several more times; but unlike when he had coughed while my dick was in his mouth, these weren’t quiet stifled coughs. No, these were real hard coughs.

“You okay?” I asked; seriously concerned that something was wrong with one of my charges.

Holding up his index finger, Ben coughed a couple more times. He then proceeded to spit out a large thick loogie before saying, “I inhaled some of it,” then taking deep breath.

“Sure you’re alright?” I asked, still decidedly concerned.

Ben spit again before saying, “Yea, I’m good.”

Joe seemed decidedly pensive for a couple second before saying, “The stuff that shoots out means you can’t suck so hard on Kyle.”

“Oh…” Ben sounded a bit disappointed, before asking, “Well, did you like it?”

“It was great,” I honestly replied, “Your brother is right; don’t suck so hard on guys who shoot cum: you don’t want to inhale or choke on it.”

“Oh…okay…” Ben still sounded disappointed.

Joe turned squarely to me, “So Kyle, Ben and me discovered something else fun we can do. Wanna see it?” he asked, changing the subject.

“What’s that?” I heard my voice asking as curiosity was getting the better of me.

“Watch,” he said with a hint of pride in his voice before moving in front of his brother and squatting down.

Ben half giggled before saying, “Get ready,” as he took hold of his own semi-soft seven-year-old dick.

Joe proceeded to open his mouth wide. Before I was even able to wonder what the two brothers were about to do; Ben began peeing…right INTO his brother’s open mouth!

I almost didn’t believe my eyes: I was watching Ben peeing INTO his big brother’s ten-year-old mouth…and Joe was SWALLOWING it! So shocked by what I was watching when I opened my mouth to say something, I was unable to even make a sound let alone form words.

Perhaps ten seconds after Ben began peeing, he stopped.

Joe closed his mouth, swallowed again, smiled, and stood. “It’s like swallowing your cum,” he commented as he caressed his bare belly.

“But better, ‘cause there’s more of it and we can make it,” Ben added in an excited voice.

“How many times have you done that?” I found myself asking.

The two brothers looked at each other and shrugged. Joe then said, “A bunch…”

“Two or three times a day,” Ben interrupted.

“For how long?” I asked as I silently wondered if drinking was safe.

“A couple days after you first babysat us,” Joe informed me.

Still wondering if it was safe to drink urine, I heard my own voice saying the words, “How did…”

“We were sucking each other, like you showed us how to do, and I just kinda started peeing,” Ben said with a giggle.

“I knew it wasn’t cum, but didn’t taste bad, and I didn’t want Ben to stop sucking me, so I swallowed it,” Joe continued the story.

“Fun as it was, I was a little scared after,” Ben said.

“Scared?” I asked.

“He thought it might make me sick,” Joe explained, “But it didn’t. I just felt full afterwards.” He took a breath before continuing, “At first were just did it at night after going to bed, now we do it every day.”

“Lots easier than going to the bathroom after going to bed,” Ben commented.

“And in the morning too,” Joe added.

“And way more fun,” Ben beamed.

Since it didn’t seem to be making them sick, I simply replied, “Oh, okay.”

“Being full is nice too,” Joe added as he continued to caresses his bare belly.

“So, what should we do now?” I asked in hopes of ending the urine drinking conversation.

There was a brief moment of silence before Joe said, “I think ‘Tomato City’ is on BMTV. Can we watch that?”

Judging by Ben’s facial expression, it seemed like he wasn’t all that interested in watching a truly horrible 60s monster movie. “Not a fan of really bad monster movies?” I asked.

He shrugged before saying, “Can I sit on your lap while we watch it?”

Remembering the previous time he sat on my lap while we watched a bad monster movie, I said, “Sure.” I took a breath and added, “Joe, since you picked what we’ll do, you have to bring the clothes inside.”

Without saying a word, Joe scooped up all of our clothes and carried them into the house. He unceremoniously dumped the clothes on the end of the sofa and plopped his bare butt down next to them.

Turning on the TV we discovered that ‘Tomato City’ was not only already on, but about two-thirds over. “You’re both taking your baths when it is over,” I informed them as I sat on the sofa next to Joe.

“Yea, okay…” Joe replied immediately engrossed in the terrible movie.

As Ben sat his bare butt on my equally bare lap he replied, “Sure.”

In light of what happened the last time Ben sat on my lap while watching a movie: I expected he’d wiggle around a bunch; my dick would get hard and would end up either in his butt-crack or between his thighs. But that isn’t what happened this time. No, this time the seven year old boy shifted his body around for all of two second immediately after sitting on my lap, and snuggled his back and shoulders into my chest before sitting almost perfectly still.

The three of us sat there, wearing nothing but socks and sneakers, silently and almost completely still for a full ten minutes before I sensed something. “I gotta pee,” I quietly commented.

Several motionless seconds passed before I spoke again, “I gotta pee.” I gently shook Ben, “You gotta get off my lap so I can pee,” added.

“Oh…” the seven year old boy responded, before sliding his bare butt off my lap. Unexpectedly, he didn’t step away from the sofa; no, he simply turned around and began to bend over.

“I gotta pee Ben,” I eritereated.

With a little nod, he said “In my mouth,” before moving his mouth over the head of my half-hard dick and closing his lips around the bottom of its head.

“Uhm…” I half paused, “you sure?”

His lips still wrapped around the head of my dick, he gave a little nod.

For a couple seconds I debated what I should do. Ultimately, the practicality of simply peeing in his mouth won-out. Looking into his eyes for any signs of distress, I relaxed my bladder: urine began flowing down the little tube on the underside of my dick. I continued to watch closely for signs of distress as the first of my piss sprayed into his mouth. Seeing no change in his facial expression, I continued peeing: the stream of my piss pouring directly into his seven-year-old mouth. Despite having watched his brother do the same thing less than an hour earlier, I was still stunned by how nonchalantly he repeatedly allowed his mouth to be filled with my piss before swallowing and letting it fill again.

Perhaps twenty second after I began peeing into Ben’s mouth, my stream of piss stopped. He gave one last swallow and lifted his head: the head of my half-hard dick dropping from his lips. Without saying a word, he turned sat his bare butt back on my lap and snuggled his back and shoulders into my chest.

A few seconds after snuggling into my chest, Ben said, “That was yummy,” and began to caress his own bare belly in the exact same way his older brother had less than an hour earlier.

Finding the movements of his hands just slightly distracting / annoying, I wrapped my arms around his bare belly. Not only was I holding his still, I was also pulling him more tightly against my chest. Can’t say that I know why; but something about how I was holding him as he sat on my lap felt so pure and innocent, maybe it was the fact that my forearms ware wrapped across his belly which held both my cum and my urine within it, that I honestly think I would have been happy staying like that forever…

Little more than twenty minutes later the movie had ended; and while the end credits were rolling both boys took their respective clothing with them as they headed upstairs for their baths. Realizing what time it was, I put my clothes back on before sitting down for the next movie ‘Attack of the Ants’.

Not more than five seconds after the opening credits had ended, the front door opened: Mr. and Mrs. Watkins were home. They paid me, and I left.

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Raeanna12/08/2021I read the Boy Babysitter series in one sitting. Please, please, please more! The variety of experiences was an absolute pleasure. Can we have more with little girls? I had so much fun as a 7ish y/o playing with my girlfriends. I wish we would have had a boy to join us.
Anonymous10/14/2021I really enjoyed the story - any fantasies with little cocks, pee, cum, etc are always fun. I just wish I had someone else to stroke with while I read it. Good work!