She chose her fighter, Cammy, a female with agility and good kicks. He went with his old favourite, Akuma, a big angry demon. He hadn't played it for a while, but he could simply spam the fireball if all else failed.
Round one, and two things dawned on him, to his agony. One, he was still too tired to concentrate and two, she had played this before. She started pulling all the moves out, and his lack of practice or expertise was causing him to suffer. She wasn't just playing, she was skilled. What he didn't know was, her and Natalie often played this when she visited as Natalie did like games. She may not have been a natural gamer, but Natalie indulged, and they were friends. Amy was by now very good at this game. His sexist assumption about gamer girls was costing him.
He was frantic, and he ended up button bashing, but to no avail. Round one went to her, and he had only inflicted damage to half of her bar.
He looked at her with astonishment in between rounds. She gave him a sympathetic shrug and a smile. He was familiar with the game, he had no real excuse, but he felt like he was being conned right now somehow.
He settled down and concentrated really hard, but this gave her greater resolve. Round two. He knew now, she wouldn't surprise him again. He started his offence, fluid, but completely predictable, not reacting to her play at all. He couldn't get near. As things were dawning on him, he got more desperate, and she got more chances to inflict heavy damage. She finished it with a super special. Round Two. Perfect. His inner being seemed to explode.
"See honey? Like I said yesterday. I'm more grown up than you. I will always win. But that's okay. Mama will take care of you."
He was welling up again. Did he really take this bet? It seemed like an easy out. Now his mother would always think he was in to this. He could never complain or voice his concerns. Or it was six extra months.
He started to gently weep. Amy lent back and grabbed Rapunzel, handing it to him, before enveloping him in her arms, where he cried. She shushed him, once again, so comforting. He needed it now, it hurt.
She grabbed his hand and led him to her room, naked except for his Rapunzel trunks and naval and ear piercings.
She sat him at the vanity with his doll as she went to get an outfit. But it wasn't from her closet. It was from one of the bags yesterday. She opened a multi pack of knickers.
"Look what we got yesterday? you can't share mine all the time!"
They were all frilled, with bows just like yesterday, in feminine pastel colours. She also had a lot of unique cartoon print ones featuring princesses, ponies and the like. There was enough for his 9 weeks. He wouldn't be out of these soon. She stuffed them all in his underwear drawer.
She had bought him a lot of socks too, many varieties went in. His heart was racing. This was bad!
She pulled out pastel yellow set of knickers and some yellow ankle socks with large lace frills on them and led him back to her room. She went back into another bag and pulled out a yellow skirt and a white petticoat, with a matching yellow crop top, and a pair of white mary jane shoes. Did he have anything to hold on to? At least the outfit wasn't pink today?
She pulled down his trunks without notice, which shocked him.
Then she held up the knickers, and he stepped into them. Again, they stretched over everything but were close enough to be comfortable. He was by no means well endowed but these were clearly more childish knickers, for comfort not style, and they were so so soft. He hated it. He hated how comfortable they were.
Next his yellow skirt, then white petticoat, which would make his skirts very noticeable. While he was waiting for her to get the top, he swished his hips. They swirled around in a large radius.