A/N: Simply finding a good word to fit a theme around is difficult enough, so I think this will be a pretty tough challenge for me. I've only got ideas for 2 or 3 of the chapters so far, so feel free to suggest an idea and/or pairing; I'll try my hardest to fit it in! This chapter will be advanceshipping, but remember that this story will be a MIX of shippings and (mostly) unrelated stories. So if you simply don't like advanceshipping; skip this chapter and wait until one you like :)

Anxiety

It was 2:00 a.m. yet May still found herself awake on this calm and clear night. The Grand Festival was beginning this upcoming afternoon and she knew that falling asleep was going to be next to impossible. She was so nervous yet she so excited; this was the biggest event in her life! Just moving on past the preliminary round on such a stage would be a huge accomplishment for her.

She got up out of bed and walked out onto the balcony of their hotel room. Seeing the beautiful city skyline was soothing for her as she tried to push the upcoming contest out of her mind for the moment. She soaked in the view for several minutes before she found herself getting rather tired. She decided it would best to try and get some rest and crawled back into bed. Miraculously, she closed her eyes and sleep immediately overtook her.

The next 10 hours had gone by in a blur for May. The contest was going to begin in a mere three hours and nerves were starting to set in for the young coordinator. The quartet was trying to decide what to get for lunch, but May didn't have an appetite. Her stomach was plenty full; full of butterflies that is.

Conversation had been going on in the background, but May hadn't paid it any attention before she decided to speak up. "You guys can pick a place yourselves. I don't feel like eating right now." The other three people in the room shared blank and understanding stares with each other because they knew how she must have been feeling.

"I think I'll stay back too," Ash said as he decided to be the first to speak up, "It wouldn't be right to leave May all alone right now." Brock nodded in agreement before nudging Max to the door so they could go and find a good place to eat. "We'll meet you guys at the contest hall." The breeder said before exiting the room.

As Ash looked sympathetically over to his younger friend, he remembered how he felt before his first match in the Indigo League. It was a very nerve-wrecking and stressful time. Because of his experience with the feeling, he knew what May needed; something to take her mind off of the contest.

"C'mon May, just stop thinking about it. We all know you'll be great so there is no need for you to get stressed out about it." He said in an attempt to help ease her mind. "I wish it were that easy." She responded glumly.

Ash walked over and sat down next to her on the bed. "I think I've got an idea of what we can do to help you out." He said with a look that May had never seen from him. Slightly confused, she looked up at him and asked "What's that?"

In a swift motion, Ash put his arm around her back and leaned in to bring their lips together. May's eyes shot open as she was completely caught off guard by Ash's unexpected move. He knew that this would not at all have been what she was expecting and he was unsure of how she would react. However, he did know that it would change what she was focused on.

May pulled back and gave Ash a stunned look while saying "What are you doing?" "Just go with it," he said, "Trust me." May was still extremely unsure about what to do, but this time when Ash pressed his lips against hers, she kissed back. She slowly found herself melting into the kiss as she pushed everything else to the back of her mind.

As the kissing got more passionate, May became more confident in the idea. She opened up her mouth and let Ash do some exploring. For someone who hadn't ever even had a girlfriend, Ash was a natural. He was extremely smooth and now had May under his spell.

He broke the kiss for a fraction of a second to get May's shirt over her head and off of her. May then returned the favor to the aspiring Pokémon master. Their fiery kiss continued as May reached her hand down and started to try and undo Ash's belt. She didn't take much time and she quickly tugged Ash's pants to the ground.

While she was doing this, Ash had gripped his hand on May's butt. He gave it a couple of squeezes before pulling her shorts off so they could join his. The two of them finally broke apart and locked eyes. A smile took over May's face as she reached for his boxers and ripped them off. Her mouth opened in surprise as she got a look at Ash's now freed erection. It certainly was bigger than she what she was expecting.

Ash smirked at the impressed girl in front of him. Not wanting to waste any time, he did the honors of lightly pushing May's mouth up against his beast. She took in a few inches of him and wrapped her tongue all around it. She started bobbing her head up and down, taking a little more every time she went down on him. Ash gave off repeated groans in admiration as the amateur sucked him off.

Ash now took a good look at May's rack. She had been blessed with hitting puberty early as her D cup breasts were poking their way out of the royal blue bra. He thought the bra had to be a push-up, but as he removed it to start to play around, they stayed up. Ash was amazed that breasts that size could manage could also be so firm!

As he started to fondle her huge boobs, May continued giving him fantastic treatment. She was now taking in a good 6 or 7 inches of him, and it was about all she could manage. She started gagging on his member as it went part of the way down her throat. She cupped his balls as she continued to work her tongue up and down on his shaft.

"Oh fuck, May" Ash let out. He gave both of her breasts a hard squeeze as she tried to hold on from cumming in her mouth. Knowing that would be an extremely difficult task, he brought May's head up. He groped her tits for one last time before letting go.

Ash laid back on his back and guided May into getting into a cowgirl position on top of him. Once she gave him the nod of approval, he entered inside of her slowly. She bit down on her tongue as she tried to keep from screaming out in pain. She sucked it up quickly though, and gave Ash the green light again.

He entered in about halfway, before retracting most of the way out, and slowly moving back in. He loved the outstanding feeling that he got as her tight pussy walls clamped down onto his hard penis. Ash let her dictate the pace, and she slowly let it increase as she became more comfortable.

"Oh yeah! Oh Yes! Yes! Ohhh yeahh!" May moaned out in pleasure as pace kept its gradual increase. Once the two of them had a little bit of a rhythm going, Ash reached back up and started to play with May's magnificent melons. He still had no clue how a girl her age could have boobs so big, but he loved it.

"Damn they're perfect" Ash grumbled out in fascination as he continued to squeeze away on his new found treasures. May smiled as Ash admired her chest. She knew that they were her best features and that they would be marveled at by many. She enjoyed having Ash fondle them, but it was nothing compared to what she was feeling thanks to his manhood.

"AHHH! Ahh! Ahh! Ahhh! AHHH! MHM! MHM! Oh god!" she let in pure pleasure as Ash started entering her fully and stretched her out to the max in the process.'He was so big!' she thought to herself as she soaked in every blissful second.

May's joy was taken to a whole new level as she finally released and had her first ever orgasm. "AHHHHH!" she let out a short and passionate scream to accompany to the powerful climax. Ash paused for a minute as he allowed for the beautiful brunette to collect herself.

Once she had returned back to Earth, Ash got off of the bed and pulled May off as well. He laid her back across a brown desk and had her hips at the edge. He crossed her legs while also setting them over his shoulders. He stayed standing and started to enter her once again.

This new position gave Ash more control and also allowed for deeper penetration. He wasted no time in taking advantage of either of those perks. He thrusted in deeper and with more vigor than before. "AHH! AHHHHH! AHH! OH! OHHHH! OHH YESSS!" May immediately started to squeal in pleasure.

As Ash continued pumping in and out of May, he really admired the wonderful view in front of him. May was a petite girl with a cute face and a nice smile. She had no pimples and had next to no fat. Her stomach was flat, but as already mentioned, her breasts were huge. He loved watching them bounce up and down as he rocked in and out of her.

Wanting to watch them bounce even more, Ash started raising the frequency of his entries. "OHHH! MHMMM! MHM! AHHHH! OHHHH MY GODD YESS!" May screamed out as the raven haired boy- wait no; man, kept pleasuring her.

"OH GOD ASH! OH YES! GIVE ME MORE! I NEED IT! HARDER! DEEPER!" she begged out. Now that he was given permission, Ash held nothing back. He entered in as far as he could before pulling out, and then sharply entered back in.

"OH MY FUCKING GOD! OHHHH! OHHHHH! AHHH!" May let out deafening screams while Ash penetrated to spots that she didn't think was possible. He was hitting her g-spot with every thrust, and she just couldn't get enough of it

Even though he wasn't as verbal about it, Ash was also in a state of ecstasy. Her pussy was so tight; even he was surprised that he could fit his whole member inside of her. Her walls clamped down on him so well, "Oh hell yeah" he muttered out.

"AHHHH! AHH! OHHHH MY GODD! OHHH YESSS! AHHHHHHHHH!" May let out an ear-splitting scream as she hit her second climax of the day. As her juices stormed out, May almost lost all sense of reality. She felt so empty yet so complete; it all just felt freaking fantastic.

Her inner walls clamped down even tighter with the expulsion of juices, causing Ash to very nearly lose control of his own cum. He managed to hold in all in though, and pulled himself out of the worn out girl. Knowing that she couldn't take another round, Ash turned his focus back to May's perfect pair of breasts.

He positioned his rod in-between them, and let May proceed to pleasure him. Feeling his cock get smothered by her cleavage was a major turn-on for him. It was sort of like a fantasy that he thought would never actually come true.

He could feel his release coming soon as he continued to play around with her tits. He rubbed his member against them while giving his final squeezes to them as well. He finally let out a deep groan as he shot his semen all over May's face and chest.

The two of them continued panting after the workout that they had just endured. May glanced over at the clock and her eyes widened as she realized that her report time was in a mere 30 minutes. She hurriedly threw clothes back on her and grabbed her poke balls before rushing towards the door.

Before she left, she looked back over at Ash and said "You were right." as a big smile took over her face. She then flew out the door and presumably toward the contest hall.

A smile also found its way onto Ash's face as he smugly thought, She acts like that's a surprise.

A/N: So I decided to try writing advance this time, next chapter will either be contest or poke. I have an idea for the story, but I'll wait to write it until I see which one you guys want me to write. If more people ask for contest, than so it shall be or vice versa. Please leave other shippings you'd like to see as well, I'm hoping to have a good variety throughout the story (keep in mind the rules I have on my profile though).

Thanks for reading!