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Once Upon A Dream World	By : CaptainParisStarr Category: Pokemon > Yaoi - Male/Male Views: 10944 -:- Recommendations : 0 -:- Currently Reading : 0
Disclaimer: I do not own the Pokemon franchise, any characters mentioned in this story, or make money, profit, or earn a living off the story.

Chapter List
- 1-1
- 2-2
- 3-3
- 4-4
- 5-5
- 6-6
- 7-7
- 8-8
- 9-9
- 10-10
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A/N- I forgot to add Trans as a tag and now they won't let me go back and add it in as my summary section is full. This fic is full of boys in dresses so if you don't like...
Who am I kidding, it's Pokemon, the show that had a character in drag in almost every episode (why did they stop that Team Rocket gag?), so it's all good!
Ash sighed, rolled over, and tried once more to fall asleep, but he just couldn't. He was too excited; starting a new journey, making new friends...
Meeting hot boys.
He pushed the last thought away once more. Ever since he had turned twelve, he had grown increasingly, and uncomfortably, aware of boys; but not girls. By the time he was fourteen, he had been forced to accept that he was gay and would never like a girl.
He still sometimes dreamed about the young man who first caught his eye; his one time traveling companion, and long term friend, Tracey Sketchit. Though he had never come out to Tracey, or given his friend any reason to suspect that Ash's feelings were romantic in nature, he still wondered from time to time what might have been had Tracey not liked girls the way he had.
Not that Tracey had ever figured out that Ash liked him that way; At least, if he had, he had never said anything about it...
Lost in his thoughts, Ash finally drifted off to sleep, but his dream was not at all what he expected.

“Welcome to the Striaton City Pokemon Gym. This is the Gym which allows you to feed your senses, and indulge in your desire for pleasure...”
The young man who was speaking had soft green hair, and pale green eyes; with a start Ash realized that it was Cilan. However, unlike the Cilan he knew, there was something very odd about this Cilan...
He was dressed in thigh-high black leather heeled boots, an emerald green dress with a hemline that fell just short of touching the tops of the boots, and was wearing makeup. Ash glanced around, and saw that Chili and Cress were dressed similarly; only in ruby red and sapphire blue, respectively.
Not that the dresses were the same; Cilan's was a basic sheath dress, Chili's was halter-style and plunged in the front, while flaring out in the skirt, and Cress' was strapless, short, and tight.
“T-this is a Pokemon Gym?” He finally managed to sputter out after several moments of staring at the brothers, open mouthed and wide eyed.
“Yes, this is a Pokemon Gym. Wanna try to challenge us? I assure you, this will be the hardest badge you'll ever have won, if you even manage to win it.” Chili smirked at him, one hand on his hip and the other pointed towards Ash.
“Yes, I challenge you! What are the... Hey, what's going... Help!” Ash began struggling as Chili snapped his fingers and two boys came forward from the crowd. Grabbing Ash, Trip began working his belt open while Paul tried to pull off his jacket. Trip was dressed in a sunshine yellow feathered frock that complimented his fair skin and pale hair, and was longer in the skirt than most of the other dresses, because of the feathers that hung from the underlay.
Paul, on the other hand, was looking surprisingly sexy in a tight short dress of dark purple velvet with a scoop neck and short sleeves, his skirt so short that he would flash everyone simply by sitting down.
“Don't you want us to prep you for the 'battle'?” Trip asked coquettishly, as he unzipped Ash's pants.
“What does Pokemon battling have to do with... with... oh....” Trip had pulled down Ash's pants just far enough to take Ash into his mouth to fluff him up.
“This Gym Badge is not won through battle. Oh no, you have to sex it out of the Gym Leaders.” Paul kissed Ash's neck between words, one hand slipping up underneath Ash's shirt to pinch at a nipple.
“S-sex it? You... You mean put out for it?” Ash panted out, half in embarrassment, half because Trip was making it hard for him to concentrate.
“Yup, you have to let them do you... In front of the rest of us. Or else it won't count for the badge.” Paul whispered, kissing Ash's ear now.
“Mmm...” Trip sounded like he was trying to agree, but was having a hard time speaking with Ash's cock in his throat and mouth.
“Oh, I think he might be ready for the real thing...” Chili was standing in front of Ash, though he had not heard him move. Up close, Ash could see that his dress was not solid red, as he had thought, but was shot through with gold thread making it shimmer like flame.
“You can stop fluffing him now.” Cilan helped Trip to his feet, then gently stroked Ash from root to tip. “This is a nice piece of equipment.”
“Uh... thank you I think?” Ash dropped his eyes, embarrassed by Cilan's compliment, and saw that there were leaves embroidered along the skirt of Cilan's dress in a paler green than the dress itself.
“So, who goes first this time?” Cress finally piped up, stepping closer, and Ash once more felt his jaw drop. Like his brothers, Cress' dress was not a single color, but rather ripped through all the shades of blue as he moved, the colors changing and rearranging themselves like the rippling of water on the top of a pond. How the effect was done, Ash had no idea, only that the results were amazing. Only the fact that Cress was not exuding the same kind of confidence that his brothers were distracted from his dress, and made Ash look at him instead.
Cress was cute, and the fact that his dress was the most eye catching, along with being the tightest and shortest of all three brothers, only added to that fact. Ash was about to open his mouth to ask if Cress could go first when Chili spoke up again.
“I'm first, I'm so hard I'm gonna pop if I don't. Cilan, would you mind prepping his ass for me?”
“Prep my... Oh...” Once more Ash found himself relaxing and allowing the touch as Cilan gently started fingering him with the help of a bottle of lube from a nearby table. Chili, meanwhile, grabbed a pair of handcuffs from the table and threaded them through a metal loop in the floor.
“On your knees, Challenger, hands together in front of you like you are praying to feel my cock fill your ass!”
Ash complied, and felt the cold metal of the handcuffs snapping around his wrists. Continuing his work, Cilan began properly finger-fucking Ash's ass.
Crying out wordlessly in pleasure, Ash failed to notice as Chili moved into position behind him until Cilan's fingers were removed from Ash's ass. Then...
“Chili! Oh... Oh fuck...” Ash whimpered in mixed pain and pleasure as Chili suddenly thrust into Ash's tight opening.
“Oh you like that don't you you little man-whore.” Chili panted as he set a fast pace that left Ash breathless and writhing.
“Open up.” Opening his mouth automatically, he pushed himself up as far as he could with his hands bound, and Cilan thrust into the wet orifice. Though the angle was awkward and he could not fuck Ash's mouth as deeply as he wished to, he still laughed softly as Ash skillfully sucked at him.
Then he felt something smooth yet hard rub over his hip and side, and realized that Cress was rutting against him, unable or unwilling to ask his brothers to move so he could get a better position.
As Ash felt himself starting to get close, Cress snapped a cock ring around his base, the brief flare of pain pushing him back from the edge, even as he felt Chili pull out and warmth splash over his ass.
“My turn now.” Cilan unlocked the handcuffs, freeing Ash's hands. “Roll over.” Once Ash was on his back, the cuffs were secured once more around his wrists, but Ash didn't mind.
Cress sat down on Ash's chest and took advantage of the new position to fuck Ash's mouth, his skirt riding up almost to his waist. Then Ash felt his legs get pushed up and apart, and a second cock was entered into his ass.
“Cress...” Turning to look at his brother, the blue haired youth nodded, and shifted his weight lower. Leaning forward, Cress lined up his ass, and Cilan helped line up Ash, then he was inside Cress!
Being double timed like that was beyond anything Ash could have imagined as Cress rode him in time with Cilan's thrusts.
Had he not still been wearing the cock ring he would have spurted into Cress within a minute, but as it was the pleasure lasted so long Ash lost track of the time, until pleasure warred with frustration and the urge to cum became overwhelming. Only then did Cilan release into his ass, before reaching around and jacking Cress until he also came. Then both boys seemed to dissolve into thin air, and Ash was left alone for a moment.
“Wow, good show, here's your badge.” The referee came over and unlocked the cuffs and cock ring. Ash barely glanced at the ref as he set to work jacking himself off, not realizing that the ref had been Brock until he had already cum and the dream was fading to black.
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Once Upon A Dream World