(I didn’t really know what the male avatar’s name was so since the female was May, I just settled for Max.)
Within the Hoenn region exists the town of Littleroot, which May had found herself moving into. She unpacked and set into place all of her things before excitedly making her way to the neighbor’s house.
“I should greet them myself.” She thought.
She opened to the front door to a 30-something looking year old woman. She rushed to the door quickly.
“Hi! You must be our new neighbor! Nice to meet you. I believe my son is the same age as you. Why don’t you go upstairs and meet him?”
May walked up the stairs, at first hesitantly. Not for long however as she walk up the stairs and around the corner to find a boy that (surprisingly enough) was the same age. He seemed to be preparing to leave for something, which was evident by the fact that he only had on underwear and was still getting changed. In fact, he was so distracted, he hadn’t noticed May until he was almost done packing his things.
“Pokémon fully restored…
Items all packed and…
Hey! Who are you?” The kid said questioningly.
“My name is May. I just moved in to Littleroot.”
“Oh! You’re the new kid! Hi, my name is Max. I don’t really have time to talk because I’m running a little late. Me and my dad are gonna research some wild Pokémon. Anyways, see ya!”
And so May had her first interaction with Max. “Weird that the first time I meet him, I’m staring at him in his underwear.” She thought, not that she would ever tell him that.
…
Some time later, after May had helped Professor Birch fight off a Poochyena, she went to meet Max again, this time on route 103. After shuffling through the tall grass in the area, she met him again. She approached Max, he once again was distracted by something. He was squatting down observing something in the grass, and he hadn’t noticed the black waistband sticking out of his pants.
“Okay, so it’s this one and that one that live on route 103… Oh hey! It’s you again! Since we’re here, how about a Pokémon battle?” Max said enthusiastically.
May had a better idea. “How about we make a bet? The loser has to do whatever the winner says. Deal?”
Max agreed.
…
“Huh, you’re not too shabby.”
Max had been defeated by May, and was now forced into fulfilling her request. May had thought back to when she met Max, and had a devious idea.
“Ok then. I got it. Turn around, and bend over.”
“That’s all?” Max thought. “Easy enough.”
As May prepped herself she had one more thing to say. “Also, you’re not allowed to move.”
Without another second passing, May reached into Max’s black pants and found an equally black pair of underwear, primed for pulling.
Max had now realized what was happening, but wasn’t opposing it. He had secretly always wondered what a wedgie felt like, especially from a girl.
May pulled with one hard yank.
“Ow! Definitely painful… but… in a weirdly good way…” Max thought, not that he would say that to her.
May got a good look at the underwear. Mostly black, with an image of a Treecko in the middle. As she kept pulling, the underwear went deeper and deeper into Max’s butt. Eventually, the leg holes peered over the pants, and May grabbed that and started pulling.
When the underwear stretched to around neck height, she let go.
“Finally, it’s over,” Max thought as he started to tuck the underwear back in. Before he could even touch the underwear, May said,
“Hey! Who told you I was done?”
Max went back to his original position. May walked around him to his front side. She reached into his pants once more. Now while sneering at him. She yanked the underwear up again.
“OW!” Max blurted. Although he knew this wasn’t the end either.
May kept pulling, each time digging deeper into his crotch. After around 5 tugs, she was satisfied. Max finally tucked in the massively stretched underwear.
“Did you really HAVE to pull that hard? That hurt you know.” Max complained.
May simply smirked and said, “Next time we battle, we’ll do another bet. That sound good?”