The Wallace Cup was over… The day came to an end and a bright orange sun descended into the sea on the horizon. With a loud bellow from its horn, the ship signaled its departure. May was going back to Johto… And he was going with her…

It still baffled Ash how quickly everything happened. Not an hour ago he was so full of competing in the Sinnoh league to battle every gym leader he could find. But then it happened. Just before she left, May came up to him, pulling slightly on the orange shirt of her new outfit. The words she said then would be burned into his memory forever.

“Ash? I wanted to talk to you, b-b-before I left…” she spoke, looking straight down at the ground. She was blushing furiously and avoided all eye contact. For some reason, to Ash she looked more beautiful than ever.

Wait, beautiful?

Before Ash could contemplate further, he felt May grabbing his hand as she pulled him close. Before he realized what was going on, May had pressed her lips to his. Almost automatically he closed his eyes and breathed in deep through his nose. She smelled wonderful, familiar… He was pretty sure he recognized the smell of May’s patented Pink Surprise Pokeblocks. They had never before smelled so divine. Their kiss was short, too short for Ash’s liking. Before he had a chance to open his mouth and let her tongue in, May had already retreated.

She stood before him, embarrassed out of her mind and blushing bright red. With feet so heavy he could hardly feel them; Ash inched toward her and took her face in his hands. He brushed away a tear and looked straight into her brilliant brown eyes.

Wait, brown?

“Y-you… Love me?” he stuttered. He could hardly hear his own words, but he knew he had spoken them.

“Ash…” she mumbled as she looked him in the eye. Slowly but surely she nodded her head.

That nod was all she could bring up, and it was all Ash needed. This time, he was the one who started the kiss, started it, deepened it and held on to May like he had never held on to someone before.

And now here they stood, on a ship to Johto, leaving behind everything Ash had fought for in the Sinnoh region. He couldn’t even remember Dawn’s tear-streaked face, nor did he have any recollection of Brock’s solemn silence as he waved goodbye.

None of it mattered, because he was following the love of his live to Johto. He would follow her everywhere.

When dusk fell, May led him to their room. As she walked, her hips caught Ash’s eyes as they swayed from left to right and Ash couldn’t help but marvel at how much May had grown and how well developed she was. They entered their cabin; he vaguely noticed he couldn’t properly read the door’s number. The room was small and distinctively orange. In the middle of the room stood a big two-person bed with faded orange sheets. To the side of the bed two orange curtains blocked the outside view. Directly opposite of the bed was an orange door which, Ash reasoned, led to a small bathroom.

May closed the door behind them, making sure it was properly locked. She slowly unbuttoned her shirt as she made her way to the bathroom. She turned to Ash.

“Why don’t you make yourself at home? I’ll just slip into something more comfortable.” – her voice was laced with desire, her cheeks flushed red. She threw off her shirt just before the door closed behind her, granting Ash a short peek of her creamy skin and the back of her blue, obviously well-filled, bra.

Damn, was she always this big? That’s gotta be atleast a size D!

Ash remained where he stood and let his gaze go over the room. On second thought, the orange was over-doing it a little bit. The room was really, really hot. He looked at the clock above the bed but he couldn’t read any of the numbers, all of them were blurry and devoid of any meaning.

Must be the nerves…

“You can turn around now…” came May’s husky voice only a few seconds later. When Ash turned to face her, he could feel his jaw hanging as his eyes widened, taking in the view. May had changed back into the outfit she wore at the Wallace Cup. An emerald-encrusted circlet kept a crème-colored veil hanging on her head, flowing out behind her back. Her legs were covered in some sort of dress in the same crème color. But Ash’s attention was grabbed immediately not by the dress, nor by the circlet, but by her chest piece, orange with golden accents shaped like hearts, and very – very rolled up, letting out May’s breasts for the world to see. Ash had never seen something as beautiful as these mounds, crème colored, bigger than the size of his palm and adorned by two rock-hard pink buds.

“Heh, I take it you like my new outfit?” she giggled, eyeing Ash with a lust she had never felt before. 

“It-… It’s beautiful May!” Ash confirmed, “but… what’s up with the-…?” he felt too embarrassed to say the words, but he couldn’t keep his eyes away.

May smiled, “it’s my own special touch, especially for you Ash and I’m glad to see you like it” she giggled and let her eyes wander downward.

Catching her hint, Ash looked down himself, getting the shock of his life. He wasn’t wearing any pants! He was naked from the waist down and his dick was standing at attention at an impressive 18 centimeters.

What in the name of-?!

“May! Oh my god, I’m so sorry!” he shouted as he desperately tried to cover himself up with his hands. Something that was made considerably harder because, for some reason, his arms felt numb and lifeless and refused to move. May didn’t seem the mind though as she walked up to Ash, smiling seductively.

“I- I- I swear! I still had them on when you opened the door!” Ash panicked, but May silenced him, once again locking their lips in a long kiss. This time, she did open her mouth, granting access to his tongue, leading to the most amazing French kiss of their lives. Ash could feel his member jerking up, slightly brushing May’s thigh. When both trainers disconnected a thin line of saliva still connected them as they gasped for breath.

May took charge again. “Don’t worry Ash! In fact, I’m quite flattered by it…” she whispered, before she slowly started to kneel before him, taking his erection into her soft hands. Ash couldn’t hold back a hiss of surprise as she traced his length with her index finger.

“You left a lot behind for me, you earned this… Just hold still and enjoy...”

Ash couldn’t believe his ears, and when May gave his rod her first experimental stroke, the sudden rush of ecstasy knocked him off his feet, forcing him into a sitting position on the bed. May slowly rubbed her right hand up and down his rod, taking in his considerable size from all sides.

Before, Ash had never been interested in the size of his penis, but lately during his travels he had developed an interest in girls and he was amused to find out his member was actually considered above average. Although the width wasn’t anything to brag about, the 18 centimeters length definitely was something he took pride in. He enjoyed it immensely to watch May marvel at the size and shape of his erection.

Before Ash could properly enjoy his girlfriend’s reaction though, she decided to speed things up a bit. She was now rubbing his length with two hands at the same time, one taking care of the top half, the other squeezing the base. She altered her rubbing with an occasional knead, earning an approving moan from Ash as he threw his head back in ecstasy. May grinned devilishly as she watched the suffering she was putting Ash through. He was desperately trying not to cum and she was determined to give him a good time before letting him burst. She stopped her treatment, instead letting his dick slip between her sizable breasts. Kneading her breasts together, May started to bop up and down along his dick.

“May! M-M-May!” Ash stuttered, his voice hoarse with passion, “that feels so good! You’re amazing!” Beads of sweat were pearling on his brow and he squeezed his eyes in concentration, biting his bottom lip every so often. When he opened his eyes a little he was met with a beautiful sight. May was looking straight at him with bright sparkling eyes, sweat on her face and her hair was flying beside her in constant fluid motion.

As May looked Ash in the eye, she winked with a grin and looked back down. She could see quite a bit of pre-cum amassing on the tip of Ash’s member. She gently slowed her bobbing down to a stop and took hold of the tip of his dick. She slowly but surely drew back the last bit of his foreskin, exposing his glistening tip. May looked at her new goal with determination in her eyes. She licked her lips and then slowly started to lick the length of Ash’s member, starting at his balls and slowly working her way up. The feeling of her hot, wet tongue on his member was almost enough to make Ash blow. He slammed his eyes shut and bit down on his knuckles, letting a loud moan escape his throat.

When she reached the top of his dick May took one last look at Ash’s face, smiling at the way his flushed face looked back at her. Then, without warning, she opened her mouth and engulfed his member, sliding a good portion of it straight down her throat. Gagging slightly, she retreated a few centimeters before she started to slowly move her head up and down, letting her tongue circle around his tip. It was all Ash could take.

“May! I’m-… I’m CUMMING!” he shouted. With an almost animalistic roar he jumped up and took a hold of May’s head, forcing his dick down her throat as he could feel himself pumping wave after wave of sperm down her throat. Ash’s world collapsed as he gave in to the amazing feeling that enveloped him. No longer could he hear May gagging on his seed. No longer could he feel the drowsy heat of the ship’s cabin. No longer could he feel the soft bed beneath him. He felt nothing, only darkness and the amazing feeling his loving girlfriend had given him.

Pi?

Pika-pi?

Pi-ka-CHU!

With a jolt of electricity Ash jumped up and opened his eyes. Gone was the cabin, gone was May in her seductive 1001-nights dress. In their stead was a dark, unwelcoming cave, lit only by a slowly dying fire in the corner. As Ash looked down, he realized that at least May’s blowjob had remained, or, well… its result anyway. He could still feel his member softening, leaving a large sticky stain on his pajama pants.

“Holy shit… A dream! It was just… a dream…” he gasped, but it had all seemed so real! Then again… His meeting with May at the Wallace Cup was 6 years ago! How could he have forgotten travelling the rest of Sinnoh, his adventures in Unova… his self-imposed isolation after the Unova League…

It had been five years since Ash competed in the Unova League. After the League tournament had ended he was back in Pallet Town, depressed and defeated, lacking a proper goal. It was then that he decided to take his training to the next level. He had gathered a team of his most trusted Pokemon, a heart-breaking event, since it meant leaving behind a lot of his dear Pokemon-friends, if only for a while. With his team, a tent and only the most basic of supplies, he had traveled to Mt. Silver where he had spent the better part of 5 years in isolation, training his Pokemon against both the harsh elements of nature, as well as the exceptionally strong native creatures in the area. Soon after arriving, Ash made himself a home in an abandoned cave, halfway up the mountain. In the years that followed he would make his way down to the nearby Pokemon center to restock on supplies, treat any major injuries and switch out any Pokemon who had trained enough for the moment.

His new lifestyle had paid off in the end. One by one his Pokemon reached new levels of power, speed and strategy, some of them even evolving at long last.

But… This new life did have its downside, Ash mused as he cleaned his pajamas in a stream outside his cave. He hadn’t physically met any of his friends in 5 years. The only means of communication between them was his Pokegear, through which they would send him the occasional plead to return to civilization. Time and again he rebuked their pleas, saying that he needed to do this, that there was no other way.

Truth be told, he hadn’t spent the whole 5 years considering Pokemon training and strategies… He had also considered other important things in life. He had, for example, finally realized what it meant to have feelings for a girl, following a wet dream he had 2 years ago. Before then, Ash had always focused solely on becoming a Pokemon master, thinking nothing of what would happen if he would ever actually reach his goal. This last wet dream was by far the most vivid one though, and it made him realize that it was time for a change.

As Ash entered his cave again, Pikachu was still waiting for him, arms crossed and an angry stare on his face.

“I know I asked you to wake me up in the morning, buddy” Ash said to him as he put on a new pair of pants and hung the cleaned one out to dry.

“But, really… Was that necessary?” he looked down at his Pokegear, noticing the time, “it’s still in the middle of the night! Besides, it was a pretty good dream too..”.

To this, Pikachu replied with a firm ‘chu!’ as he jumped up and slapped Ash’s Pokegear with his tail.

"Oh! You mean I received a new message?” said Ash as he caught on to his companion’s meaning.

Sure enough, as Ash scrolled through the device’s menu, he found that he had indeed received a new message. Two of them even, he realized as he flicked open the device.

Subject: Special Invitation! The Battle of the Champions awaits!

Date: July 15th, 2017, 23:45

Subject: Ash, read this or I’ll come and MAKE you read it! It’s important! x May

Date: July 16th, 2017, 0:23

Curious, Ash tapped the screen and opened the first mail. He had considered opening May’s message first, but… First come, first served, and he doubted he had a clear enough mind about May yet after his startlingly life-like dream.

Vulcan Island, July 15th, 2017

Dear Mr. Ketchum,

It is with great delight that I hereby wish to extend you a formal invitation to compete in the Battle of the Champions tournament, this coming August.

The Battle of the Champions is a new tournament, officially sanctioned by the Pokemon League, where qualified trainers battle it out for a special chance to take on the reigning Pokemon Champion, Cynthia. As you well know, defeating Cynthia in a full 6 versus 6 battle earns the victor the title of Pokemon Champion and Pokemon Master.

You were chosen for this invitation because you have consistently placed high in previous Pokemon Leagues across the world. You have also aided the safeguarding of Pokemon around the world in other areas as well, which has also greatly pleased our judges.

Should you accept this invitation, please reply to this message immediately and we will officially sign you up. If you so choose, you will be expected on the top of Mt. Rapture on Vulcan Island on the 3rd of August. Starting a week prior to the tournament, various ferries and airliners will open up, allowing free passage for competitors and greatly reduced prices for their friends and family. Should you desire to travel to the island yourself, please find the enclosed download with the exact coordinates for your Pokegear map.

On behalf of the Pokemon League Association,

Charles Goodshow, Chairman

Before Ash could fully comprehend the invitation, his eye caught the last bit of the message. Attached was another attachment besides the coordinates. Curiously, he opened it, revealing a calling card from Cynthia herself. On it was written in bright red text: “I’ll be waiting for you Ash… Don’t let me down!”

A challenge, from the champion herself!

He didn’t take much more to make up his mind. He quickly replied to the e-mail, signing himself up for the chance of a lifetime. It was then that he regarded the untouched message from May. Swallowing, he opened it:

Hey Ash!

I just caught the most amazing commercial on the television! They’re going to hold a huge championship in only a few weeks! I’m sure you know about it by now. Hell, maybe you’re even competing yourself! If you’re still half the boy I knew 5 years ago, I’m sure you will…

But anyway, whether you’re competing or not, YOU ARE COMING. No buts, no ifs. You’ve been holed up in that mountain far too long now! It’ll be great to see you again, as well as everyone else! I’ve already invited all the other guys from our old traveling group. It would be great to get together again after so long, so don’t you dare chicken out of this Mr. I’m-going-to-train-until-I-am-a-Pokemon-Master-or-I-die! You WILL be on the ferry to Vulcan Island on July 31st, or I will personally come and get you, in pieces if I have to!

Xxx

May Maple,

Editor/Photographer – Pokemon Fashion Magazine

Seaside Avenue 42

Slateport City

Hoenn

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Grinning, Ash closed the message and looked at his Pokemon partner, Pikachu had long since fallen asleep. “So that’s why you wanted to wake me up eh? You want to see everyone again, too?” Looking back at his Pokegear, he swiftly sent a response, confirming his arrival. In a swift back-and-forth of e-mails Ash and May arranged to meet at the foot of the forest surrounding Mt. Rapture, where they would make the last trek together.

Putting his Pokegear away, Ash laid his back down on his pillow and looked at the ceiling of his cave.

“Well, Pikachu…” he mumbled, “looks like it’s time for a change. A new goal… A a new beginning...” And with a feeling of euphoria Ash closed his eyes and let sleep overtake him. Maybe, just maybe, he would succeed this time. Somewhere in the back of his mind, another voice added to his.

Maybe, this time I’ll have the courage to go up to May and confess.

No…

No more maybes… No more ifs… This was a chance he was not going to waste!