Gary Oak signed in annoyance as he wanted in the woods. here he was, the mother fucking best trainer the world had ever seen (at least in his own mind) and he was waiting after midnight for a meet up just outside of viridian city.
Normally he wouldn't of been caught dead outside this late at night, not with the league coming up and having put himself on a strict regiment of exercise, training and sleep, but he'd received a note from a secret admirer who had promised to make it worth his while if he met them at this time, in the woods.
and now whoever the fuck it was suppose to be was running late.
"I swear to god, if I wasn't so blue balled.." He muttered to himself, keeping his light up watch again and giving it anther five minutes TOPS before he took off.
"M-maybe I can help with that.." Came a voice.
Gary turned to face the voice, already recognizing it as belonging to ash ketchum, his wanna be rival. The dork was in the shadows so Gary couldn't make him out, but he still gave a grunt of annoyance.
"Ok dork, whatever. I don't really swing that way but glad to have it confirmed you've been hanging off of..of.." Gary said but then ash stepped into the moonlight.
He heard what ash was wearing before he saw it, and couldn't believe his ears at first but then as Ash was illuminated in the pale moonlight his eyes confirmed it.
Ash was dressed in massive diapers, to the point the boy was waddling like a baby learning to walk and was bare foot (which explained WHY it had taken him a bit longer then expected to make it to the meet up.)
The diapered were pikachu yellow for the most part, with orangeish red tapes and as to be expected little chibi pikachu's running around  and playing for the designs on the padding.
aside from the diapers, the only other thing that Ash had worn out to the woods was a massive pikachu print yellow bonnet, with a ribbon under it tied in a cute bow.
Looking at the way ash was dressed, one would of expected for Gary to burst out laughing and start mocking the other trainer, but the thing of it all was Gary had a deep down fetish for diaper wearing beta boys.
and Ash was checking off all his wants and more.
"S-So what do you think? A-Am I cute?" Ash coo'ed, wiggling his hips and crinkling loudly, and the tip of his right index finger on his bottom lip.
"I..I Uh..I.." Gary said, blushing and in the moon light Ash could make it out and smiled.
"hehehe I knew it!" Ash giggled and clapped his hands and switched to a seductive smile, then kissed his right palm and blew a kiss over to Gary and winked. "Mwah~"
Much like a pokemon being hit with attract, the effect was instant and super effective as Gary got little hearts in his eyes. Still this was ASH, his rival and childhood friend and not one of those random twinks he'd meet on the road and have some fun with. 
shaking his head Gary tried to find the willpower to resist.
"Hehehe I can see your trying to fight it, but it's no use daddy~" Ash said and waddled over, a huge predators grin on his face. "I've got you locked in my sights and your NOT getting free! We both know despite your earlier claim your barn door at least swings both ways, though from what Daisy told me it really prefers cute widdle guys like meeee~" 
Gary gulped and squirmed, frozen in place as Ash came in close and then put his arms on Gary's shoulders and around his neck, then licked his cheek.
'I should of NEVER told Daisy about this!' Gary whimpered mentally, while at the same time also thinking. 'But hot damn, If she's the one who filled in ash I owe her a huge thank you gift.'
"A-Ash..I..Look.." Gary said, willing himself to come under control and taking a firm hold on ash's arms. 
"yes daddy?" ash asked.
"I..I need to know if you actually like..um..dressing up like this or if your just doing it because you like me." Gary said.
As cute as ash was, he wasn't gonna make anyone dress up JUST for him, he had standards after all.
"pfft, silly daddy. I'm a total diaper wearing beta dork. Sooo even if you don't wanna play with the baby, I'll still be rocking huggies." Ash giggled and then darted in, smooching Gary's cheek. "That said..Richie is too vanilla for this, Brock is too big brother and won't play fun games, and Snap just wants to take pictures. I never even thought you'd of been into this till Daisy caught me in my diapies and spilled the beans on you. I've always like liked you~" 
"..W-Well I mean..I've always kinda liked you too, but your always so stubborn and stuff..I never even thought you'd of um.."
"turned out to be a bigggg baby just waiting for the perfect daddy to keep me small and helpless forever?" ash giggled and kissed Gary's other cheek.
"Yeah..that. heh.. You know if we do this..I'm gonna wanna keep you with me.. we can still travel around and challenge gyms but you'll always be in diapers and always be daddies little boy right?" Gary said, pulling ash into a hug now and kissing his forehead.
"Ehehehe threaten ME with a good time." Ash coo'ed and winked.
and so the battle was over so to speak. a wild baby had appeared in the woods and to this day it's hard to argue exactly who captured who.
Gary would be a loving and dotting daddy to his widdle ashy but wasn't scared to lay down the law when needed, but on the other hand Ash had Gary wrapped around his little finger. 

The end