Chapter 1: The Bet
It was cool winter morning in Pallet Town. Ash Ketchum had already competed in the Hoenn League taking second place and gaining much valuable experience in the process. Now he was preparing for his next quest should there be any.
"Pikachu use Thunder!"
"Ludicolo, dodge and use Hydro Pump!"
A tiny yellow mouse with pointy ears and a long yellow tail jumped up into the air and quickly shot a powerful bolt of lightning at a middle-sized greenish creature wearing a sombrero. The creature dodged the bolt and shot a powerful blast of water at Pikachu.
"Pikachu jump over it and use Iron Tail!" Ash commanded.
Pikachu barely avoided the pump of water jumping over it. Then, in mid-air his tail glowed a bright white color before crashing into Ludicolo knocking him back a few feet.
"Now finish him off with Quick Attack!" Ash yelled.
After landing on the ground Pikachu rushed towards Ludicolo in a burst of speed hitting it hard and crashing it into a nearby wall and fainting it.
"Ludicolo return." Brock said as he returned his creature.
"Good job Pikachu." Ash said as his long-time partner perched himself onto its masters shoulder.
"That was a good match Ash. Pikachu is defiantly strong." Brock said congratulating him.
"Thanks Brock. Your Ludicolo is a strong Pokemon. You just gotta train more and maybe you'll be like me one day." Ash said gloating in a mocking tone.
"Yeah, yeah. Just don't let your ego get bigger then your head." Brock said sighing at his friend's overconfidence.
"It's already too late for that Brock. I bet you ten dollars Ash won't be able to fit inside his front door." A female voice said from a few feet away.
They turned and saw a girl wearing a red shirt, red bandanna, and a white skirt.
"May? What the heck are you doing here?" Ash asked confused.
"Well, my dad came down here for a Gym Leader conference and I had to come with him for the weekend. We rented a house in Viridian so, here I am." May replied explaining her situation.
"That's awesome! Come on, I'll introduce you to my mom." Ash said dragging May inside his house.
"Those two. They'd make one heck of a couple." Brock said chuckling at them.
Inside the Ketchum residence Mrs. Ketchum was doing dishes in the sink and other motherly duties. She heard somebody come inside the front door and turned to see Ash walk in dragging May by her arm.
"Ash calm down. Hey, let go of me!" May yelled finally breaking free of Ash's iron grip.
"Mom this is May. She was one of the people that helped me on my journey through Hoenn." Ash said introducing her.
"Hello May. Ash has told me so much about you and how you want to be a Pokemon Coordinator. It's nice to meet you." Mrs. Ketchum stated.
"Yes, I'm trying to become the best Coordinator there is. I already have 3 ribbons." May said showing Mrs. Ketchum her ribbon case.
(Lets just say by some twist of fate and some odd alternate universe Ash is done with the Hoenn league and May has three ribbons, k?)
"Those are very nice ribbons and I'm sure you're a great Coordinator. So, are you two happy together?" Mrs. Ketchum asked implying they were an item.
Ash and May both blushed a dark red and Ash yelled at his mom.
"Mom! We're not together. May already has a boyfriend back in Hoenn." Ash said quickly making up excuses.
"I do? Wait, Ash I don't have a" May then noticed Ash giving her a look as if too go along with it.
"Oh yeah. I'm dating this guy I met in Hoenn. We've been together for years." May quickly stated in a convincing manner.
"Oh, well that's too bad. Ash needs somebody to be with him. He may train Pokemon well but he doesn't know the first thing about love." Mrs. Ketchum said disappointed.
"Mom! Cut that out." Ash yelled now feeling embarrassed and humiliated all at once.
"Ash I just remembered something, my dad wanted me to help out at his convention in town so I have to go. Bye!" May said quickly walking out the front door.
"May, wait! Don't!" But it was too late as May was already out the front door.
As the door closed Mrs. Ketchum continued her onslaught on Ash's personal life.
"What's wrong with that girl Ash? She seems nice enough." Mrs. Ketchum asked bugging Ash.
"I already told you May has a boyfriend in Hoenn mom. Why don't you just let it go?" Ash said trying to drop the subject.
"She was lying and I could hear it in her voice. Ash, why are you against dating a girl? First Misty and now May. Oh no, are you gay?" Mrs. Ketchum said shocked.
"What? Mom, I'm not gay! I just haven't had time for a girlfriend lately." Ash stated. Astonished that his own mother would even think that.
"Well, if you're not gay then I have a proposition for you. I bet that you can't get a girl to like you within two weeks. If you can then I will leave you alone for the rest of your life. If you can't then you have to let me set you up with a girl of my choice." Mrs. Ketchum explained.
"Set me up? Who were you going to set me up with?" Ash asked slightly curious.
"Well, there is always that nice Cindy girl down the street. She's available."
"Cindy? Mom there is a reason she is "Available". She is a 6 foot freak with braces and a gorilla face." Ash yelled.
"Well if you don't want to be paired with a gorilla then I suggest you start looking. Now if you'll excuse me I have some more dished to do." Mrs. Ketchum turned around and went back to doing dishes.
Ash gave her a look of despise and the one-fingered salute before walking out the front door in anger. What Ash didn't know was May had never left and was watching the whole conversation through a window. She saw Ash walk out his front door and watched him burn off some steam.
"Stupid mom. I too can get a girlfriend if I wanted one. I'm just busy training my team. Right Pikachu?" Ash said turning to his partner still perched on his shoulder.
Pikachu nodded with a reassuring sound that told Ash he would be alright.
"Yeah, I know I'll be ok. Now I just have to figure out who would want to pretend to be my girlfriend." Ash stated.
"Well, you can always ask me." A familiar voice said.
Ash turned around to see May standing behind him.
"May? What are you doing here? I thought you had to help your dad at a conference." Ash asked confused.
"I just made that up because I knew you were going to have a fight with your mom. Ash, I'm not sure why your mom is so obsessed with pairing you up with a girl but I'll pretend to be your girlfriend." May explained in a calm and caring matter.
"May, that's so nice of you. But, I cant. I couldn't put you through that, its not fair to you."
"Come on. Are you saying you would rather be stuck with some freak with braces that's 6 feet tall?" May asked smirking as she put her hands on her hips.
"Ha-ha, very funny. Well, I guess if you don't mind. Ok, lets meet in town tomorrow to rehearse. Mom may be annoying but she's also pretty sharp about knowing lies." Ash replied in a happy tone without even realizing it.
"Ok, see you tomorrow Ash." May said turning around and walking back to her home.
Ash just watched May walk away with a smile on his face. "Thank you May. Maybe one day I'll be able to tell you my true feelings."
Pikachu looked down at Ash and couldn't help but smirk. He had a crush on May something fierce and now was his chance to admit it.
"Come on Pikachu, let's go get some rest. We got a big day ahead."
Well, there you go. My first fic after months of not writing. I'm deeply sorry about not writing sooner but I had to get the inspiration back for another fic and now I got it. For those asking "Who the heck are you?" My pen-name used to be Pokemonmaster14 as you may recognize some of my old fics in my story list. Well, I'll get around to updating as soon as I can. Well Good or bad (But preferably good) review please.