May Maple was at a bit of a crossroads in her life. Ever since she first started her journey Ash Ketchum had been a source of companionship and inspiration for the young coordinator. When she first met him she had not even received her first pokemon but together they traveled through the entirety of Hoenn and now through Kanto. Over the course of this time period their group had faced more dangers than any of them expected. They faced off against the hooligans that were Team Rocket, an insane butler and his quest to revive Groudon, an alien pokemon, Team Aqua and Magma, and a tree that tried to kill them. Whether through skill or sheer luck, all four of them managed to survive all of these experiences. They were currently at Terracotta Town, where a unofficial contest was going to be held the next day. They were in the pokemon center relaxing in their rooms. May signed up for the contest as soon as the group arrived. After all, if she was going to compete on the Johto circuit then she would need all of the practice she could get. She was shocked when Ash decided to enter himself into the contest as well. He had never really showed that much interest in contests besides helping her prepare.
"I wonder how he is going to do" May thought, as she went down to the dinning hall to grab. Ash was already there eating alone. "Where are Brock and Max?" she asked the trainer, sitting down next to him with her own plate of food.
"Max wants Brock to give him some tips on caring for pokemon" Ash explained.
May nodded and began eating as her thoughts returned to her mind. She remembered how annoying and bratty Max had been when She first started her journey. However, she realized that how much of a positive affect both Ash and Brock had on her little brother, causing him to mature into a budding trainee.
"So why did you decide to enter the contest?" she asked the boy next to her.
"I know you're leaving soon so I thought that it would be great for the two of us to compete against one another. You know, give you a challenge like Drew does." Ash laughed.
"Of course, we both will do our best." May nodded at his response, as her thoughts continued to plague her.
The green-haired coordinator had plagued her ever since she had started her contest career. At first he was a dick but eventually the two of them became friends even if they had to compete against one another. He had flirted with her several times and even mentioned that he was going to Johto to attempt their contest circuit. May had some feelings for Drew but those seemed to be more towards the brotherly kind. Ash on the other hand was completely different. He was strong, yet kind, fiery, yet loving. All of these traits came together to form the person that was Ash Ketchum. May knew she had some hidden feelings for him but she didn't know how to get them off of her chest.
"Ash you know there is…" she was interrupted as Max and Brock sat down with their own trays.
"What were you saying May?" Ash asked,
"never mind" came the simple response. With dinner finished, the four of them broke apart a spent the rest of the evening relaxing and preparing for the future. May made sure she had purchased boat tickets back to Hoenn for both Max and herself before drifting off to sleep.
The Next Day
May performed at her normal level during the preliminary round of the contest, using her Eevee to propel her team into the next round. What really surprised her was Ash's performance. He and Glalie had outperformed some names that May recognized from other contests. He went first in the next round and defeated his opponent, getting him to the final round. May took a deep breath, knowing that she would have to face him if she won her match. She breezed through her match, setting the stage for the finals against Ash. The two of them were back in the locker room chatting.
"I guess this is it. I better tell him my feelings." May thought, as Ash approached her.
"May are you feeling ok" he asked the coordinator.
"I'm fine Ash but I have to tell you something important to tell you." she replied, taking a deep breath.
"I'm listening." came the retort from the Pallet Town native.
"When I first started my journey over a year and a half ago saying I was green was an understatement. But traveling with you has been inspiring not only for me but for Max as well." She explained.
"You've had a similar affect on me" Ash revealed, shocking the coordinator. "The way you use moves in contests have given me new ideas for battles." he continued.
"Ash I don't think we are on the same page." May sweat-dropped.
"What do you mean?" he asked, confused at what she was getting at.
"I'm trying to say that I love you idiot" she yelled out before realizing her mistake and clamped her hands over her mouth.
"Oh, I see." he said softly approaching her once more and moving May's hands off of her mouth.
"Ash I'm sorry I just…" She was interrupted as her friend placed a soft kiss upon her lips.
"It's ok, I think I've fallen for you as well." he whispered. "Would you be my girlfriend?" he asked,
"Of course," came the response as the two of them engaged in another small kiss. After they broke apart it was almost time to head out for the finals. "What are we going to do about us? I mean I am leaving for Hoenn before heading to Johto." May brought up to her new boyfriend.
"We'll talk about it later, let's just enjoy our battle" came Ash's response. The two of them stepped out onto the contest floor and released their Pokemon, with Ash sending out Sceptile while May called upon Blaziken. Although there battle lasted for only a short amount of time, for the two trainers it was eternity. When May first started as a trainer Ash had told her that when two high level trainers battle time would slow down for these trainers. She was currently experiencing that now.
"Its just like he said" she thought as their pokemon clashed. With a last gasp Ash ordered his Sceptile to leaf blade and she countered with her Blaziken to use blaze kick. A giant explosion occurred as the timer sounded indicating the battle was over. Both trainers looked up to see that they were tied in points thus resulting in a draw.
"Congratulations you two." the announcer called out, "Unfortunately we don't have another ribbon to give out".
"Don't worry, I've got an idea." said Ash "Sceptile leaf blade". Ash threw the ribbon high into the air where the gecko pokemon slashed it in half vertically causing a piece of the ribbon to fall into each of the trainers' hands. May smiled and the crowd cheered as the duo took a bow and the contest ended.
A Few Hours Later
It was late a night and May was in her room on the computer looking at the website containing the tickets for her boat ride to Hoenn tomorrow. After doing some research May discovered that Sinnoh contained an even more impressive contest circuit than Johto and nearly equal to Hoenn's. She was debating whether or not to lend Max one of her pokemon to get home alone while she headed with Ash to this new region. It was at this moment she received a knock on the door.
"Who is it?" she asked, going over to said door.
"It's Ash, I wanted to talk with you about something." her new boyfriend revealed. Smiling, the coordinator opened the door and let the trainer inside of her room before closing the door behind him. "So as you already know, I am going to be heading to the Sinnoh region to enter their league. I was wondering if you be willing to join me and try to make this relationship work." he asked his girlfriend.
"What do you think I'm doing now." she responded motioning over to her screen containing her research on the region's contest circuit. "I have decided to come with you so we can be together" she revealed, going to the boat website and purchasing a ticket with Ash.
The Pallet Town native rejoiced at this news a planted a kiss on his girlfriend's lips in celebration. When he tried to do it again May placed a finger on his mouth and hushed him. "We will have enough time for things like that later. For now I have to tell Max that he will be going back to Hoenn alone.
The Next Morning
Before they went to bed, May had told her brother about her decision to stay with Ash instead of traveling alone and heading back with him. Although Max was a bit upset and having to go back alone but felt more comfortable about it after May gave him Blaziken to protect him. Max assured May that he would send the fire type back to her once he got back to the Petalburg Gym. With that the four of them split up, with Max going on the boat to Hoenn and Brock back to Pewter City. The new couple was currently in the Pokemon center discussing what Pokemon Ash should take with him to Sinnoh.
"I was thinking of just bringing Pikachu and starting over again like I did in Hoenn. What do you think May?" he asked his girlfriend.
The coordinator took a few moments to ponder before answering, "I know Pikachu is powerful enough to take on a legendary Pokémon, but I feel that you still need to bring those who haven't evolved to gain more experience, as well as a flying type just in case Team Rocket decides to stalk us again." she advised.
"Did I ever tell you that I love how smart you are." Ash laughed, before giving her a peck on the cheek.
"No, but thank you for sowing me that you care." she answered back, as the duo contacted Professor Oak. After much deliberation, Ash decided to bring with him a team of Pikachu, Cyndaquil, Totodile, and Swellow. "Great, now we just wait until tomorrow for the boat" May explained, as the duo went off to shop and prepare for their new journey. Once they did this, the two love birds decided to have a nice quite dinner at the pier and retired for the night despite their desire to go farther.
The Next Morning
The duo met each other at the dining hall before heading off to the dock and boarding the boat. The journey to Sinnoh would take six days so they would have plenty of time to kill. During the first afternoon, a lottery was held among the passengers to decide who would get a room upgrade to the penthouse suite of the boat. Somehow Ash ended up wining the raffle which also contained an all-you-can eat coupon for the entire week. May was ecstatic at this and the duo ended up moving to the room.
"It's beautiful." exclaimed May throwing her bag down on the King-sized bed and going over towards the window. The view from the room was astounding as it was the floor right underneath the deck.
"You're right it really is amazing" said Ash, walking into the room and taking a seat on the bed. He took a look around to see what else the room had to offer. There was a large fireplace and a full sized bathroom. There was also a phone where they could call for room service at any point during the trip and have food brought to them. "So what are we going to do about the sleeping arrangements" he asked. Being the gentleman that he was, Ash was willing to sleep on the couch so May could have the bed.
"We can always share the bed." May whispered, blushing furiously.
Ash did a double take, not sure if he heard his girlfriend correctly. "We can worry about it after dinner, let's go eat." he offered instead.
May nodded and the two of them unpacked and called for room service. After they ate their fill May decided to take a shower while Ash headed to the service counter to get pokemon food for their upcoming trip. When he returned May was already sleeping, tucked into the bed.
"She does look beautiful when she sleeps" Ash thought, going into the bathroom for a shower of his own.
He brought his pajamas with him and took a very long and relaxing shower. After a while he finally got out of the shower and dried off his body. Getting changed, he stepped back into the bedroom and his mouth dropped. May was sprawled out on the bed in a very scandalous position in nothing but her panties.
"Ash come here." she said seductively, motioning forward with her finger.
"What are you doing?" he gulped, coming forward and standing next to his girlfriend.
"What do you think dear, I'm ready for you to make me a women." she laughed, causing him to blush a deep scarlet color. "Come on I know you want to, Misty told me that you two never fucked so we're both virgins." she revealed.
Ash sighed taking a deep breath he spoke up "May I don't want to get you pregna…" he was interrupted as May handed him a large pack of condoms. "Well I guess we can get naughty." Ash laughed, ripping off his shirt and pouncing his girlfriend.
May giggled as the two began to make out, Ash kissing along her neck and jawline before engulfing her mouth. His tongue poked at her oral opening, begging to bet let into its caverns. May allowed her boyfriend's tongue in and the two of them battled for dominance, their fleshy appendages intertwining with each other. This continued on for several minutes until the duo needed to breath and broke apart.
"Let's get these off you" Ash whispered huskily, tugging at his girlfriend's bra. May undid her bra and threw it into the corner of the room, while her boyfriend did the same with her panties. Ash let out a gasp as he took in the sight of his girlfriends naked body. "Your beautiful" he whispered as May snaked her way down to Ash's pants and removed them to reveal his semi-hard member.
"And you're just as handsome." she laughed, licking her lips as she gripped her boyfriend's member and began stroking it.
Ash let out a loud moan as his cock stiffened and reached its full 8-inch mast. May placed her lips on the tip of her lover's cock and gave it a kiss before putting her mouth over the entire head. The coordinator began to shove Ash's phallus deeper into her throat and sucked as hard as she could. Ash held on to the point where May almost was out of breath when Ash finally came. With a loud grunt he released his semen into his girlfriend's mouth and down her throat. May retreated with a loud pop and Ash's member came out of her mouth. Ash continued to shoot a string of white, drenching his girlfriend's face and breasts in his cum.
Ash leaned in a gave May a kiss, tasting his essence, "Delicious." he laughed and engaged in another kiss.
"Fuck me Ash, make me a women. I want to prove to you that I am no longer that scared little girl I once was." she pleaded.
Her answer came in Ash ripping opening the condom package and pulling the contraceptive device out. He carefully slid the latex material over his dick and pulled it all of the way up to his pubis with a loud snap. May shivered as her boyfriend straddled her dripping opening and slowly inserted himself into her vagina.
Ash inched forward until he hit a small barrier, "If I've learned anything from the books I've read, this might hurt." he warned the women under him.
May nodded and then screamed in pain as Ash rammed forward, busting right through her hymen. Ash felt his girlfriend's blood trickle down his member and onto the bed sheets and adopted a look of concern on his face. After a minute May's breath calmed and she gave her lover the signal that she was ok. With that the trainer began to start a rhythm of thrusts into his lover's core. May let out a loud moan as her walls struggled to fit her boyfriend's girth in its confines.
"Your so tight, I love it." Ash grunted, putting more force into his thrusts.
"And your so biiiiig." May screamed as she came onto her lover's member.
The male trainer continued to pound away at his lover's pussy as she recovered from the effects of her orgasm. Over the next hour May would continue to experience the highs of love and marvel at Ash's stamina. Eventually however, the trainer would finally reach his breaking point. "May I'm close" he whispered, driving deep into her walls and hitting his lady's cervix with ever thrust. In one final desperate attempt to milk her lover, May's walls clamped down with more force then they had before.
"Here I come" Ash roared, a came in force, filling up his condom to its fullest. To prevent semen from spilling over, he pulled out of his lover and deposited the rest of his liquid into the trashcan next to the bed. With that May collapsed on the bed, as Ash removed his condom and threw it away.
"That was wonderful" May whispered, feeling Ash curling up next to her under the covers of the bed.
"I hope we continue to do this for a long time." responded Ash as he put his still erect penis between his girlfriend's ass-cheeks. With that the two lovers drifted off into dreamland, knowing that they would be spending many more nights together in the future.
Eight Years Later
Ash was currently sitting on a park bench enjoying the sun. He couldn't believe it had only been eight years since he and May had arrived in Sinnoh. The two of them took the region by storm resulting in May winning her first grand festival and Ash finally winning a Pokemon league. He even got offered a spot in the elite four, which he accepted. The two of them decided to settle down in Sinnoh and a year later May became pregnant with their first child. Their daughter Catherine was coming back with May after getting ice cream and walked up to him.
"Daddy are we going to visit grandma and papa soon?" she asked cutely.
"Of course dear, next month in fact." he answered, kissing her forehead.
"Yeah we have to tell them about your new baby brother or sister." May laughed, rubbing her belly. Ash threw his head back and chuckled, His family would be growing and who knew that Pikachu destroying someone's bike after being captured by Team Rocket would lead to him having such a great life.