Skylar\'s World

This is my first story and I hope that y'all like it! Please post reviews on what you like or don't like. It follows Skylar, a Pokemon Trainer, through the Pokemon World and shows what he's willing to do to be on top.

I just want to warn that there is a lot of sex in this story. It will contain everything imaginable. So if you don't want to see guy on guy sex, humans fucking pokemon, and pokemon fucking other pokemon, then this story is not for you. For especially gruesome parts of the story (a lot of blood, death, etc.) I will mark it with a * when it starts and ** when it ends. It will not interrupt the story much, you'll just miss how some people die (death will be uncommon). Anyways, I hope you enjoy it!

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Chapter 1: The Price For Being Late

This story follows the adventures of Skylar throughout the Pokemon world. Being only 10, he is ignorant to many things in the world, but some he is soon going to discover, even things most boys never want to experience first hand. This all begins in Pallet Town...

“Ahhh I’m late!!!!” Skylar yelped as he looked at his alarm clock. “Why hasn’t it gone off?!?!” He was red with irritation, when he realized he never cut the alarm off... “I HAVE to get there before Gary Oak and Ash Ketchum, or else they’ll take all the pokemon! They’re the only expected trainers in Pallet to get anywhere, but I’ll show them I can make it too!

He ran downstairs and out the door before his mother could even offer him any breakfast. She was worried about sending her little boy out into the real world. She hoped that the rumors weren’t true....more like prayed to god that they weren’t...

Skylar bolted to Oak’s laboratory and stopped at the entrance to catch his breath. The door was propped open and he looked inside to see Professor Oak and Ash Ketchum talking in the middle of the room.

“But I NEED a Pokemon!” yelled Ash

“If you woke up earlier, then you would have gotten one...” countered Oak calmly. Skylar looked down in shame at this, for he woke up even later than Ash.

“I’ll do absolutely ANYTHING to get a Pokemon!”

“Well...there is one Pokemon...”

“I’ll take it!!!” yelled Ash excitedly. Skylar wanted to run in and say he wanted it, but he just stood outside and watched.

“Well, this one is more special...and the pokeball is even special, having a lightning bolt on it...”

“Cool!”

“Yes, cool....however, you’ll have to do something extra for it, since it’s so special...”

“Like what?”

“Turn around and get undressed.. After which, bend over.” Ash didn’t get where this was going, but Skylar did. He noticed the bulge growing in Oak’s pants, whereas Ash was too busy getting undressed.

“Okay, now what?” Ash was excited, not knowing what was about to happen.

Oak unzipped his own pants and yanked them down to his ankles. He wasn’t fully erect, but as he eyed Ash’s tight hole, untouched by anyone else, his penis flung into life. He wasn’t completely evil, he wet it with his saliva as lubricant....but that wouldn’t make much difference with the pain; it’d just make it easier to slide in. Skylar noticed his large size, about 8 inches long and 2 inches wide.

Ash didn’t realize what was going on until Oak’s manhood was poking at his tight hole. Ash automatically went pale, whereas Skylar guiltily started getting an erection.. Oak didn’t waste any time, he thrust his penis into Ash’s ass and pounded like no other.

“AHHHHHH!!!” Ash was screaming in pain so loudly, Skylar started to feel horrible about being turned on by this, but he kept watching.

No one knew this about Professor Oak, that he liked little boys. No one except Gary Oak, his grandson. For he stood at the window on the wall opposite the doorway Skylar was standing in with a video camera, recording this whole scene. The window practically covered the whole wall, but Professor Oak and Ash were too preoccupied to notice. Even Gary had an erection. He wasn’t hiding it either, he was standing there jacking off at this spectacle, his personal squad of cheerleaders standing behind him, watching.

Skylar had the perfect seat in the house, being able to see everything. He could see Oak’s humongous cock as it plowed through Ash’s inexperience sphincter muscles, which have only let dinkleberries pass, let alone a large penis. Professor Oak obviously loved this, for he was moaning louder than Ash was screaming. Skylar gulped at every thrust, watching Ash’s ass be pounded, as well as hearing the loud smacks of skin, which sounded similar to small claps of thunder.

“Please...stop!” begged Ash, managing to choke it out between thrusts

“Don’t you want a pokemon?” asked Oak, talking calmly, as if he wasn’t ramming someone’s ass.

“Yes....but this...hurts...so much!”

“You said you would do absolutely anything for a pokemon?”

“Yes...but there’s...got to be....another way...”

“To be a Pokemon Master, you have to endure pains and struggles. If you can’t bear this, then you wont stand a chance at being a Pokemon trainer!”

It took Skylar a while to notice how large Ash himself was, measuring at about 6 inches long and an inch and a half wide. He couldn’t explain it, but Skylar began to crave for it. He figured he was just horney, for there’s no way he was attracted to guys... He always liked watching his parents having sex. His friends said that was gross, but he countered with “How else am I supposed to learn about the birds and the bees? First-hand experiences are always best.”

“Wow they’re really going at it...how much longer is Oak going to ram his tight ass? I kind of want a turn... No no no! I am NOT gay! I’m bisexual! That’s a good reasoning!” Skylar was muttering to himself. He wasn’t worried about being overheard, for their moaning and screaming drowned out every other sound.

Skylar wasn’t nearly as oblivious as Ash, for he had experience in this kind of thing....rape. His father always liked to “teach” his son how to get fucked. Occasionally, if he was a good boy, he even got to learn how to fuck. His father started this when he heard from his teacher that he liked to learn via firsthand experiences about this kind of stuff... At first Skylar hated it, because his father was rough and never used lubricant.

“This will prepare you perfectly for if someone rapes you. They won’t use lube, so now it’ll hurt less when it happens. You have a nice cute ass, so I KNOW it’s going to happen one day.” After a while Skylar began to enjoy it, even look forward to when he would be “his father’s bitch,” which is what people said about those who were the ones that bent over. He never really thought much of it, because it was against his will, and he figured he wanted it because of his desire to satisfy his father. But he realized that he wanted to satisfy more men than just his father.

The only difference is the size. His father was much smaller, being 4 inches long and about an inch wide. So it never really hurt, aside from the force behind it. Seeing two men having sex with large cocks really made his ass tingle.

There started to be a change in Ash. He was no longer screaming; he was moaning louder than Professor Oak himself. This made it impossible for Skylar to resist playing with himself, so he reached his hand into his pants and started jacking off. He looked to see if Gary was still watching, and indeed he was....with someone else. Apparently one of his cheering girls had joined him and watching, for Gary was now fucking her in front of the window. Her boobs were pressed against the glass and you could see she was enjoying herself. The other girls seemed a little jealous, but they resolved it by playing with each other. They were having their own personl orgy, fingering each other, eating each other out, and one even had a strap-on.

“How does it feel now?” Professor Oak suddenly asked.

“It feels....pretty good.” Ash moaned

“Yeah, the pain becomes so monotonous that the pleasure eventually overwhelms it.” Oak said.

“I like it...AHHHHH!!!” Ash suddenly moaned loudly, jerking everyone’s attention to him.

“My orgasms usually have that affect on people.”

“Please don’t stop!!!!” Ash yelled when Professor Oak pulled out.

“Well, it seems someone else wants in on the fun.”

Skylar was so caught up in the anal that he didn’t notice Professor Oak staring right at him. “Ummm...hey guys...” he muttered nervously.

“Come on in boy! Don’t you want a Pokemon?”

“But isn’t the extra one for Ash?”

“I have a few extra Pokemon. I figured Ash was more likely to take it in the ass if he thought there was only one left...”

“WHAT?!? You mean I just got raped for no reason? And he’s going to waltz in and get a Pokemon just like that???” Ash screamed at the Professor

“No...I figured you’d want to continue getting fucked. Unless you want to fuck him.”

“Hell yeah! If I had to take it in the ass, so does he!”

“Okay, then I’ll fuck him in the mouth. By how much he’s staring at you, he might like the taste of your ass glued into my cock.”

Skylar walked in front of them and bent over, a little nervous. He looked up at Gary and noticed that he was now fucking his cheerleader in the ass. She wasn’t enjoying anal that much, but she probably didn’t want to upset him. The look on her face was one of pain, but Gary’s face was one of intense pleasure. Her large breasts spread out over the glass, turning Skylar on even more, making him impatient to get fucked.

“Mmm, he has a nice ass.” Professor Oak said as he rubbed Skylar’s ass all over.

“Yeah, and my dick is about to plow into it.” Ash said, surprisingly excited about having sex with
another guy.

“Mmm. I might have to do him after you. He’s going to deserve a decent Pokemon by the time were done with him.”

“Please, fuck me hard. I really want it. I want both of y’alls huge cocks in my tight ass.” Skylar begged, wanting to be fucked hard.

“Ohh, he really wants it. Better not keep him waiting.” Oak said as he assumed his position in front of Skylar. “Open up.” Skylar didn’t even have a chance to breathe before Oak forced his giant cock into his mouth, ripping his lips apart and going deep into his throat. Skylar was surprised at how far it went. He’s given blowjobs before, granted they were never voluntary, but it never even went into his throat. Aside from the slight discomfort due to the size, he kind of liked it.

“Now my turn.” Grinning, Ash pressed his dick against Skylar’s ass. “Man, it wont seem to go in.”

“You have to be patient. Without lube it’s more difficult to get it in.”

“Should I add lube?”

“I don’t have any, so just fuck him dry.” Oak said, seeming happy about it. “It feels better for the pitcher when no lube is used.”

“Then why did you add spit to yours before fucking me?”

“Because I’m bigger than you...and I don’t want to be too brutal in Gary’s porn movie.” Oak said with a smile. At that moment, Ash looked over at the window, his penis pressing against Skylar’s tight asshole. He automatically flushed bright red, but then started to cum a little when he saw one of Gary’s cheerleaders fucking him in the ass with a strap-on. Apparently the girl he fucked in the ass wanted some revenge, so she took a strap-on and began raping him. Skylar automatically felt a pang of sympathy for Gary, since the fake cock was rather large and the girl was showing absolutely no mercy.

Ash began to press into Skylar’s ass harder. The cum that spread over the head of his cock allowed it to slide in a little easier. It was then that he realized he misjudged Ash’s size. He must have not been fully erect. He was 7 inches long and slightly wider than before. Ash felt happy after seeing Gary’s smaller cock, 6 inches long and an inch and a half wide. The look of pain on his face added something to it as well.

“Ohhh. Mmm yes!!” Skylar began to murmur around Oaks dick.

It took a minute or two for Ash’s penis to fully penetrate Skylar’s ass, at which point Ash started ramming his ass as hard as he could possibly manage. Oak stopped thrusting, since Ash rammed him so hard that that alone allowed Skylar’s mouth to be fucked. Skylar was in heaven. It hurt, but knowing that he had Ash’s fully erect cock up his tight ass made it worth it. He made sure that he licked Oak’s penis all over the head and down the shaft. When his tongue made contact with the head, Oak let out a moan and started fucking his mouth again. It hurt in a good way when Oak and Ash rammed at the same time. It hurt getting it from both sides, but having a 7-inch cock up his ass and an 8-inch cock down his throat at the same time felt amazing.

Ash didn’t last long. Within a few minutes he had came, which caused Skylar to let out a loud moan. The feel of someone letting off their load in your ass just felt magical. Oak let off a load in his mouth at the same time. Ash didn’t stop though. He kept ramming, knowing that fucking a mouth was nothing compared to fucking this nice, tight ass. Every now and then he got too carried away and his dick slipped out, which was fine with both of them because the feel of his dick spreading those poorly experienced sphincter muscles. Skylar knew that Oak would be even better, having a wider and longer cock. He enjoyed having Ash making love to him, but he wanted to be fucked by a larger gun. After Ash let out about as much semen into Skylar’s ass as he could, he finally pulled out and he switched positions with Oak.

“Ohhh, your ass looks even tighter than Ash’s.” Oak said with delight.

“Trust me, it is.” Ash said, out of breath.

Oak slid his monster cock into Skylar’s ass before Ash could start fucking his mouth. Skylar let out a huge moan, making Ash jump a little. He regained his bearings and quickly crammed his dick down Skylar’s throat, turning his moan into a muffled gurgle. The only sound was that of smacking skin and wet mouth-fucking.

“Oh my god.” Moaned Professor Oak “You’re so tight! It seems impossible for your muscles to be able to spread enough to let me in! Ohhhh...Mmmm...Yesss!!!” Oak just kept moaning one-word sentences in extreme pleasure. It only got louder when he erupted in Skylar’s ass. Skylar didn’t expect it to be this incredible. It just exploded in the tight confines of his rectum, racing into him. The pressure behind it hit his prostrate and made him wild. Eventually both of them pulled out, worn out.

“So I guess I get my Pokemon now.” Skylar said with clear disappointment.

“Not quite yet.” Oak grinned menacingly. He looked out the window to see his grandson being gang-raped by his cheerleaders. Apparently they had two strap-on dildos of great sizes. “So how much did this hurt you?”

“Not too bad, the sense of being fucked made it nice, and the pain was a sexual pain. Therefore just adding to the pleasure.”

“Good. Ash, pick him up and slide him down onto your cock.”

Ash did so without hesitation. Skylar’s ass was still leaking with semen, causing the insertion to be easy and sounding with a loud “squish” sound. Skylar didn’t hesitate to throw his arms around Ash’s neck and start making out with him. First it was just lip-to-lip, since he expected Ash to shove him away. Instead, he kissed back with force, cause both of them to be much hornier than before. Skylar got an erection again, which poked into Ash’s belly button.

Skylar began to press his tongue between Ash’s lips, meeting little resistance. Before long their tongues were moving all over each other passionately, wrestling each other to the bottom of each others mouths. However, it was disrupted by Professor Oak as he revealed his plan. He was behind Skylar and was inserting his dick into his ass as well.

“WAIT!!!” Skylar screamed as yet another cock forced it’s way into his tight ass. “I can’t take both cocks at once! That’s spreading my ass by four inches!”

“Well, then the more painful it is should make it pleasurable, as you said before.”

Before Skylar could counter, Professor Oak had successfully inserted half his cock into his ass. Pain erupted in his ass and tears flowed down his face. Ash started to kiss him in order to provide some comfort. It didn’t help much, but he attacked Ash’s mouth with his own. When Oak had full inserted his cock, the pain subsided slightly, mainly because it was replaced by the intense pleasure of having two cocks rubbing up against his prostrate. He screamed. This was driving him wild. He clutched to Ash’s hair and made out with him with extreme force. Both men were fucking him as one gigantic beast. Skylar was having orgasms without even touching his penis, shooting semen all over Ash’s belly and chest, some even made it into his mouth somehow. Skylar thought this was the peak, that it couldn’t get better. But then Oak and Ash both orgasmed together, shooting over a cup of semen into his prostrate, causing him to scream extremely loud. Ash and Oak both pulled out, covered in sweat. Semen was dripping from Skylar’s ass, sore as hell. Skylar fell to his knees and started sucking Ash’s dick and made sure he licked every bit of semen off his dick.

All three looked out the window as they struggled for breath. Gary was lying on the ground and one of the girls was going down on him. Everyone in the room got dressed.

“Well, I think you two definitely deserve these Pokemon. Skylar, you deserve an extra special one for your performance.” Oak went back into his storage room and came out with a Poke ball that was solid black. “Now this one is a pretty rare Pokemon and maybe provide fun for you.” Oak sent the Pokemon from it’s ball to reveal what was inside... Skylar and Ash looked in awe. Even Gary, looked away from his current large-breasted lover to see what it was....