Chapter 1

Timmy lay awake in his bed, anxious about meeting his new babysitter for the first time tomorrow. "I hope he's fun. I guess it's pretty cool mom got me a boy babysitter, maybe he'll actually want to play video games with me," The little boy thought to himself. Timmy was beginning to drift off to sleep, but first, he had to do his now nightly ritual. It was only a few months ago that the little boy discovered that humping his stuffed teddy bear while wearing his silky soft sleep shorts felt really, REALLY good! Timmy positioned the bear beneath his private parts and began humping, the 7-year old's adorable little bubble butt pistoning up and down beneath his blankie. The motion allowed the intensely sensitive underside of his little pee-pee head to slide against the inside of his soft, satin sleep shorts. To add to the pleasurable sensations, the humping motion caused the tight sleep shorts to ride up in between his butt cheeks, tugging on his little testicles along the way. Though Timmy didn't understand what exactly he was doing, he knew the sensations were unbelievable. The little boy never was able to make it all the way to the grand finale though, he always drifted off to sleep long before, lulled by the intensely pleasurable sensations.

"Timmy, Can you come here please?" shouted the little boy's mother from the front of the house. Jake looked on as the figure of the small 7-year-old boy began to appear. From a distance, Jake could see he was shirtless, sopping wet, and wearing a pair of swim trunks, he had just come from swimming. When little Timmy was fully in front of him, standing by his mother's side, Jake could barely contain himself over the sight before him. Timmy stood about 4 feet [122 cm] tall and had a bowl-shaped haircut of golden blonde hair draped atop the most angelic face you could imagine. He had bright blue glistening eyes, an adorable button nose, and chubby cheeks that were slightly glowing red from embarrassment. It was just a face you wanted to hold and pinch so bad. He was quite thin for a boy his age, with just the slightest little baby-fat belly protruding over the waist of his swim trunks. The trunks themselves were little kid SpongeBob Square Pants themed, and were fairly tight fitting, even on this little boy's frame. His precious, hairless legs and feet appeared as though they would be as soft and smooth as velvet. Jake did all he could to keep from drooling over the sight of the beautiful little cherub before him.

"Jake, did you get all that?" asked Timmy's mother.

"Huh, What?" Jake was quickly pulled out of his trance by the sound of Timmy's mother's voice.

"I want him in bed by 10 O'clock, bathed and cleaned, and no sugar before bed. Ok?"

"Yes, absolutely. That will not be a problem," replied Jake.

"Ok Timmy, you can go back to the pool now." said the boy's mother. As Timmy turned around to head back to the pool, Jake couldn't help but notice the boy did have somewhat of a little bubble butt, likely the cause of the tight appearance of his swimsuit. His tight little SpongeBob trunks were riding up the toddler's little butt, giving him quite the wedgie! The trunks quite clearly outlined each of the young boy's supple, squishy little butt cheeks, and the adorable crevice separating them. Thinking of all the things he could do with this boy alone for the whole weekend, it was all Jake could do to keep from busting a nut right then and there!

"Ok, so while Timmy is playing in the pool, you can go ahead and get started on your guys' dinner, everything is prepped in the fridge. Are you sure you're gonna be ok?" asked the mother.

"Don't worry about a thing. I got this." Jake remained in the drive way, standing and waving goodbye to Timmy's mother as she entered her car and drove away. With Timmy in the back playing in the pool, Jake went inside to get dinner started.

From the kitchen window, Jake could see little Timmy frolic and play. He was practicing doing cannonballs, running in and out of the water many times. As Timmy was climbing the ladder out of the pool one time as Jake was watching, the weight of the water began to pull Timmy's trunks down, revealing just the very top of the boy's little butt crack. Jake salivated over the thought of getting to touch that supple flesh, but did his best to concentrate on finishing dinner, so he could hurry up and bring Timmy inside.

"Timmy, Suppers ready." shouted Jake out the patio door towards the pool. He saw Timmy climb the ladder out of the pool and dry off with a towel as best he could. As Timmy approached the patio door, Jake could tell he was still very nervous and embarrassed by the ordeal. Jake kneeled down and put his hand on the lad's shoulder to talk to him directly.

"Hey buddy, you don't have to be nervous around me. I'm a really fun and cool guy! We're gonna have the best weekend ever, I promise." Jake reached down and gave the tot's exposed belly button a little tickle, eliciting a bright smile and cheerful giggle from the little boy.

"Ok." squealed Timmy.

Jake tussled the boy's hair and led him inside. Timmy went into the bathroom to dry off and change while Jake set the table for dinner. Once eating, Jake tried his best to engage the young boy in some small talk.

"So, what do you like to do for fun, Timmy?"

"Well, I like to hang out with my friends a lot. We play video games together and go swimming together sometimes."

"That's cool, do you have a lot of sleepovers together here?" asked Jake, his mind immediately racing to kinky, dirty thoughts.

"Yeah, sometimes, my friends really like staying here."

"That's so cool. So you like videogames?"

"Mhm."

"Ok, well I know your mommy said you have to be in bed by 10 o'clock, but, just to prove to you how much of a cool guy I am, what if you and I played some video games together for a little while after your bath?"

"Oh really!? That would be so awesome." Timmy shouted excitedly, his hands pressing down on his chair to emphasize his happiness. The two boys smiled at each other, Jake relieved to see Timmy very happy and smiling, no longer nervous in the slightest.

After supper, Timmy went to watch some TV in the living room while Jake cleaned up the kitchen and drew his bath for him. Jake got a nice, warm bubble bath ready, and set out a towel and all of Timmy's clothing for him. On the floor near the tub, Jake noticed Timmy's swim trunks laying in a wet, messy pile. Jake bent over to pick them up by the mesh netting interior. The thought of the fabric in his hands being wedged deep within Timmy's butt crack, possibly even in contact with the toddler's butthole, gave Jake an immediate throbbing erection. Jake pressed the swim trunks into his face, inhaling deeply, and even licked where he thought the boy's butthole might have been. Sadly, nothing aside from the taste and smell of chlorine could be distinguished. Unable to resist, Jake pulled his own shorts down and wrapped the mesh netting around his throbbing cock. He began stroking himself and was soon dripping precum onto the fabric. Jake stopped however, realizing he should wait for an opportunity to play with Timmy together. Looking over the little tyke's clothing Jake had set out for him certainly was not helping the situation though. The little boy's clothing consisted of a silky soft T-shirt with an adorable little puppy splayed across the front, tiny SpongeBob cartoon briefs with a little pee-pee hole in front, and SpongeBob's smiling face plastered across the butt, a pair of silky, dazzle blue gym shorts, and tiny SpongeBob branded cotton socks. "Wow, Timmy certainly likes SpongeBob." thought Jake to himself. Jake so longed for the opportunity to scrub and bathe this little boy, but his mother informed him that Timmy is a very independent little boy, and will insist on bathing by his lonesome. Jake did not want to break any trust he had with Timmy at this point by even suggesting otherwise.

"Timmy, Your bath's ready." shouted Jake out towards the living room. Jake watched little Timmy enter the bathroom and shut the door behind him. Jake decided to go to the game console in the living room and see what games Timmy had to offer. He only had E-rated cartoon games, SpongeBob and the like. "Such an innocent little boy." He thought to himself. Jake loaded up a SpongeBob game and started playing, hoping to learn a little bit while Timmy was still bathing. After about 30 minutes of playing the game, Jake heard his name being called from the bathroom. Jake approached the bathroom door and could hear Timmy was slightly crying.

"Jake, can you please come in here?" Jake's heart raced with the hope that he was about to see little Timmy standing there, butt naked and sopping wet! He opened the door, but instead saw Timmy sitting on the toilet fully clothed, except for his shorts and undies around his ankles. Looking at his face, Jake could see the boy was tearing up.

"I…I don't know how to wipe my butt." sniffled the little boy. Jake's heart dropped to the floor.

"Aw, that's ok. There is nothing to worry about, don't cry." Jake kneeled down to the boy and embraced him in a warm hug. He looked down towards the boy's lap, hoping to see a little acorn, but it was sadly covered by the flesh of his thighs. "I will gladly wipe your butt for you." Jake picked Timmy up from the toilet and sat down on it himself. He then bent the boy over his knee, poopy butt and all staring straight up at him. The sight and smell of the toddler's poopy-stained butt was in no way a turn off at all. The little boy's butt was snow-white in appearance, and without a hair follicle in sight. Jake shuddered as he placed his hand upon the boy's bare butt cheek for the first time. It was porcelain-smooth to the touch, and Jake could not resist from giving the vulnerable little boy's butt cheek a gentle pinch. Jake grabbed a wet wipe and began wiping between Timmy's butt cheeks as the boy remained silent. When the surface of Timmy's butt appeared poop-free, Jake began spreading his butt cheeks apart for a thorough clean. As he spread the boy's cheeks, staring back up at him was a perfect, flawless beautiful little rosebud of a butthole. At this point, Jake's erection was titanium hard, and spewing more precum into his own undies.

"Hey Timmy, has your mommy ever put a thermometer up your butt?"

"Yeah. Why?" replied Timmy innocently.

"Well, I just wanna make sure you're completely clean back here. Is it ok if I put my finger up your butt for a little bit? I promise I will be gentle."

"I…I guess that's ok." said Timmy, still slightly sniffling.

"Ok, Timmy, you're gonna feel a little pressure, but everything will be ok." Jake inserted his bare finger directly into Timmy's butthole. The tightness and warmth of the orifice now engulfing his finger was overwhelming. Jake gently scratched his fingernail along the inner lining of Timmy's butthole and dug out any leftover poop he could, reveling in every second of it. Satisfied the butt was sparkly clean, he removed his finger from Timmy's butthole, and traced it down slowly along his butt crack, following the curvature of the boy's round, squishy bubble butt cheeks. Before long, Jake's finger was travelling along Timmy's smooth, hairless taint. Progress was halted as Jake's finger bumped into the two most adorable, teeny tiny, hairless little testicles he could ever imagine could even exist. Jake wanted more than anything to keep going, to reach under and grasp Timmy's little willy and stroke him to his first ever mind-blowing orgasm. Figuring he had violated the little boy enough for now however, he decided to instead pull up the boy's undies and shorts without probing further. Seeing the boy's butt glisten under the dazzle blue gym shorts was enough to cause Jake to begin rubbing the boy's butt in slow circular movements while he was still bent over Jake's knee. Jake savored the feeling of the palm of his hand gliding over the thin, slippery surface of Timmy's gym shorts. Jake loved the sensation of his hand rising up to the top Timmy's right butt cheek, sliding down into his distinct crack, and rising up again onto the left butt cheek. Jake moved the palm of his hand down towards the bottom, squishier part of Timmy's butt and gave a little squeeze. He then gave two quick little spanks across Timmy's butt. The second spank allowed Jake to feel the butt cheeks jiggling as a result of the first spank. That feeling brought Jake dangerously close to creaming in his undies. Jake finally let Timmy get up

"Ok, your butt's all clean, and everybody's happy." said Jake, wiping the last of the tears from Timmy's face. "How bout we go play some videogames now, huh?" To this, Timmy smiled brightly, and forgot all about the ordeal he just went through.

"Ok, I have to go pee now though." chirped Timmy.

"Hey, I have an idea! I know a fun pee game we could play." said Jake in response.

"How can you play while peeing?" asked Timmy, a confused look on his face.

"We both pee into the toilet at the same time, facing across from each other, and try to get our two pee streams to run into each other."

"Oooh, that sounds fun!" squealed Timmy. With happy, smiley approval from Timmy, Jake proceeded to pull his own undies and shorts down in front of the boy, exposing his pulsating 6" [15 cm] erection. "WOOOOOW! That's HUGE!!" exclaimed the boy. "Why is it so stiff like that?"

"It just means I have to pee really, really bad." replied Jake simply, not wanting to confuse the boy too much yet.

"And it's so hairy!"

"Yeah, yours will be hairy like this someday too, when you're older." explained Jake. Walking up to the toilet, Timmy directed his soft little 1" [2.3 cm] willy into the toilet bowl and started peeing. Jake started to pee as well and aimed towards Timmy's stream. Timmy giggled adorably as the two streams hit each other, making a splashy mess. When the two boys were finished peeing, they each pulled up their undies and shorts and walked into the living room.

"Here, come sit up by me." said Jake, patting the couch cushion next to him. As the freshly cleaned little boy climbed up close to him, Jake reveled in the aroma of the clean boy and his sweet strawberry shampoo. He wanted to cuddle him more than anything in the world. As the game progressed, and Timmy was clearly kicking his butt, Jake tried to distract the boy with a surprise tickle attack. Timmy burst into a fit of laughter as Jake alternated between tickling his armpits and belly button. Gasping for mercy, Jake decided to finally give the boy a chance to breathe and recover.

"Hey Jake." breathed the boy, trying to regain his composure from the tickle attack, "can I ask you something?"

"Of course, Timmy, anything at all." he replied.

"I know it's really late, but I was wondering, would you let me stay up and watch a scary movie with you? It's something I've always wanted to do." Jake's eyes ignited at the thought.

"Absolutely Timmy." Jake went to the television's rental screen and looked for a good horror movie. When he found one, he invited Timmy to snuggle up close to him under the blanket. Timmy laid his head across Jake's lap, as Jake gently caressed his hair and face. Feeling adventurous, Jake decided to slip his hand down toward Timmy's tushy and slip just his fingertip under the boy's shorts and undies and nestle it right between the very top of the boy's butt crack. He began scratching his finger gently back and forth between the boy's plump cheeks.

"Hee hee." giggled the boy in response, "that tickles, I like it!" Jake smiled with immense delight as he continued picking the toddler's butt and caressing his face while they watched the movie. For the really scary scenes of the movie, Timmy had to completely bury his face in Jake's crotch, which Jake found absolutely adorable and erotic. As the movie was reaching its end, Jake asked Timmy how he was doing.

"Hey buddy, you feeling sleepy yet?"

"No, not really." whispered Timmy quietly. A very depraved thought came to Jake's head.

"Hey, I know what could be fun. You wanna do something that the REAL big boys do?"

"What's that?" asked Timmy, very curious.

"Well, have you ever heard of porn?" asked Jake.

"Porn? What's that?"

"Well, have you ever gotten like a really, really good feeling, right…here?" Jake moved his hand directly over Timmy's genitals and gave his soft, squishy pee-pee a little squeeze."

"Actually, yeah. Every night I've been rubbing my pee-pee up against my teddy bear, and it feels so good!" exclaimed Timmy.

"Really? Would you want to try having that same feeling together? Me and you?"

"Ok, that sounds fun." answered Timmy excitedly. Jake loaded up some porn on his phone and started streaming it to the television. Immediately, Timmy's eyes went wide with disbelief.

"Why are they naked?"

"Well it makes those special feelings feel even more intense. Hey, I have an idea, what if me and you got naked?"

"Ok. I guess we could do that" replied Timmy, slightly hesitantly, but still trusting of Jake.

Having Timmy stand up in front of him, Jake Kneeled down to meet Timmy at eye level. Looking directly into Timmy's eyes, Jake could barely stand how adorable this little boy was. Jake gently placed the backside of his hand onto the boy's cheek, slowly caressing it. He worked his hands further down Timmy's body, laying them to rest on the boy's hips. He slipped his fingers into the waistband of Timmy's shorts and started tugging downwards. He pulled them down to the boy's ankles, leaving his tiny package bulging in the front of his tighty-whities. Jake used his forefinger and thumb to delicately fish the boy's little pee-pee out from the Y-front of his undies. He rolled the head between his fingers and gave a little tickle to the immensely sensitive underside of the toddler's little helmet.

"Ooooooooooooooh." cooed Timmy, in deep satisfaction, "that REALLY tickles, but in a very different way." Jake rubbed his finger directly over Timmy's pee hole, and then brought the finger to his own mouth. It tasted lightly of fresh little-boy pee, which was pure heaven for Jake. Timmy giggled at the sight of this.

"Hee hee, you like to taste my pee?" said Timmy, teasingly. Jake smiled and pulled the boy close to him. Jake placed his right hand on Timmy's still undies-clad butt.

"Uh-oh, looks like someone's gonna have a wedgie attack!" Jake grasped the fabric of Timmy's undies and pulled it tight up into his butt crack, exposing each of the boy's little butt cheeks. With his right hand still yanking, and his left hand now pinching each butt cheek back and forth, Timmy started giggling hysterically.

"Hee hee, stop it! My undies feel so weird up my butt like that." laughed the little boy.

"Ok, ok, I'll stop." Jake pulled Timmy's undies off, leaving him naked except for his shirt and socks. Jake proceeded to pull down his own shorts and undies and sat on the couch. Timmy jumped up on his lap, his bare butt cheeks pressing down directly onto Jake's throbbing erection. The pair began to watch the porno, and Timmy was immediately enthralled by what he saw.

"Hey, that man's rubbing on that girl the same way I do to my teddy."

"Yeah, it's called humping, Timmy, and it feels super good." Jake started thrusting up into Timmy's butt himself.

"Does that feel good for you?" asked Timmy, curious of Jake's movement.

"Oh yeah, super good. Your butt's so soft, Timmy."

They continued watching the porno, but Jake knew he had to raise the stakes. He went in for a savage, merciless tickle attack of Timmy. The little boy went into an absolutely hysterical fit of uncontrollable laughter as Jake's agile fingers darted between the boy's armpits, belly button, inner thighs, butt crack, and testicles. The attack caused Timmy to fidget wildly, and his silky-smooth butt cheeks to unbearably stimulate Jake's throbbing boyhood. As the pre-cum from Jake's cock began to lubricate Timmy's butt cheeks, and he began humping more aggressively, his cockhead became enveloped in the boy's butt cheeks, pressing right up against his butthole.

"Jake, seriously! Stop, I'm gonna pee!" cried Timmy. Jake had no intentions of stopping anything. His merciless barrage of tickles continued, even faster than before. Timmy was laughing like a maniac, and squirming violently.

"Oh my god, Jake, I'm peeing!" he was not kidding, Jake's intense tickling had caused a stream of warm, yellow pee to begin flowing from the tip of Timmy's cockhead. Jake reached his hand out and wrapped it around the boy's penis, holding it as he peed. The pee quickly saturated the couch, and the warm liquid felt comforting as it spread out beneath Jake's own butt cheeks. As Jake became imminently close to orgasm, all tickling ceased immediately, and Jake instead wrapped his arms tightly around Timmy's body in a vice-like grip. He buried his face deep into Timmy's shoulder and began thrusting up into his butt savagely.

"UUUUUUUUUUUUUGGGGGGGGGHHHHHHHHHH!" Jake groaned gutturally as he emptied a huge load of his thick, sticky cum between the boy's butt cheeks. Timmy could immediately feel the wetness permeate his most private of areas.

"What just happened? Did you just pee too? In my butt!?" Timmy reached back with his hand and stuck his fingers up his butt. He collected a sample of the gooey mess on his fingertips. "Ewwwwwww!" Exclaimed the boy, "it's all sticky." he giggled. He brought the gooey sticky mess up to his nostrils, "and stinky! What is it? Did you pee?"

"No, I didn't pee. It's just my happy juice."

"Happy juice?"

"Well yeah, that soft, squishy little butt of yours made me really happy!"

The little boy giggled at such a silly proposition.

"How did my BUTT make you happy!?" squealed Timmy, his voice adorably cracking on the word butt.

"Well, you know the feeling you say you get when you rub up against your teddy, and when I tickled your willy?" asked Jake.

"Yeah."

"Well, if you keep stimulating it like that, and keep going and don't stop, you will have a really, super duper intense happy feeling through your whole body. And when you're older like me, that feeling will make you squirt out happy juice."

"Really!?"

"Yeah, and when your soft little tushy buns were squirming all over me, it made me have that happy feeling! Do you want to try and see if we can get you to have it too?"

"YES! Absolutely, please." begged Timmy. With his left hand, Jake Reached under Timmy's butt and towards the underside of his shaft. As Jake gently stroked his index finger up and down Along Timmy's willie, it began to harden for the first time ever from a 1" [2.3 cm] squishy little button into a proper cock.

"Ooooh, oh wow! Yeah, that feels really good. It kinda feels like I have to pee though too." Jake loved how adorable the little boy's innocence was,

"It's ok if you pee. Even if you pee on the floor, I'll clean it up. Just relax and let yourself go." he instructed. Jake reached his right hand around Timmy's belly and wrapped his hand around Timmy's cock and began stroking. He moved his left hand back to tickle the boy's balls and slowly circle the rim of his butthole with his thumb. Jake continued pumping Timmy's cock intently, hard enough for the little boy's testicles to jiggle and bounce as Jake tickled and cupped them. "Ooooh, does that feel good baby?" Whispered Jake quietly into Timmy's ear. Nothing escaped the boy's mouth aside from intermittent cooing and grunting. After a little while of this, Timmy finally began to vocalize.

"Oh Jake, I really think I'm gonna pee." Jake lowered his head down to kiss the boy on the cheek and whisper in his ear softly.

"It's ok baby, go ahead and pee." Jake started stroking much faster and increased the intensity of tickling his balls.

"OOOOHHH I'm gonna pee, IM GONNA PEE!!!" screamed Timmy. At that instant, Jake jammed his thumb far up Timmy's butthole to stimulate his prostate as he continued pumping at breakneck speed.

"I'M PEEEEEEEEEIIIIIIIIIIIIIINNNNNNNGGG! UUUUUGGGGGGGGGGGHHHHHHHHHH!" Timmy grunted hard as his penis convulsed in Jake's hand, his sphincter muscles closed tightly around Jake's thumb, and his entire body quaked with the pleasure of his very first orgasm. Even though it was a dry orgasm, Jake knew Timmy would never be the same again. When Timmy finally caught his breath, he began to speak.

"Wow! That was incredible. I didn't make a sticky mess like you though, or even pee." said Timmy, slightly saddened.

"Yeah, you're still too young for that, you just had a dry orgasm. It will happen soon though." Jake assured him. Jake gave Timmy another kiss on the cheek and wrapped his arms tightly around him. The two boys cuddled lovingly while lying on the couch, and eventually fell asleep in each other's arm, both butt naked and covered in Jake's cum.

To Be Continued