Why is May the only traveling companion with any sort of noticeable...load, so to speak, in the first few generations? Here's a picture between all of them Seriously, between those 4, they gave May, a 10-year old, the largest size. And now, in generation six, where it seems like a little more liberty was taken, if not just because of the clothing changes in the game, Serena also has a noticeable pair. I might be over-thinking this, but....why? Heck, even when May was brought back for those few episodes in Sinnoh, the size was toned down to "flat", like the rest of them are. Do the sizes of females in Pokemon just change depending on where you are? Because these guys are all around 10-14 right?
Just from looking at the screencaps here, the obvious reason is that the anime for Gen 4 and 5 had a more "flat" animation style. You can tell that Dawn and Iris have breasts too if you look closely, but the animation isn't shaded as well, so it's harder to actually see them. As for the Misty, I assume she was designed to look as young as Ash, while the others were supposed to look mature compared to him. Even Dawn, who was very inexperienced compared to Ash, ended up being having a more mature personality than him.
My guess is that maybe the ones who animate May and shiz are clueless to the whole "everyone-in-pokemon-is-10yrsold" fad and see her as older due to her appearance and decided to give her some milkbags. thats just me.
Ok, so May is going to have us like when she's 15 in the show, while the others just cause us to be like
Considering it took Ash nearly 15 years to age two years, I don't think we'll have that problem. Also just because someone started to develop at an earlier age doesn't mean they're gonna have huge gazongas. Hell, I was flat as a pancake until I was 16 and I think I've developed quite nicely.
Or to give older people something to exaggerate on and make lots of pictures with may and giant puppies that just make you forget she's 10...... I don't have a secret motive, nope, not at all