When Pocket Monsters Best Wishes! originally started, Pokémon seemed to be breaking a lot of traditions they usually did. The first hint at this was in episode two when Satoshi (Ash Ketchum) officially met Iris – Iris hadn’t been riding a bike, so it didn’t end up getting fried by Pikachu at some point. One of the other traditions too for Pokémon was to have Ash be forced into a crossdressing situation at some point during the series, which started way back in season one in episode 26, “Pokémon Scent-sation”. I thought Pokémon was going to break that tradition (and later thought only Dent (Cilan) was going to be the only one to crossdress when he ended up cosplaying as Kamitsure (Elisa) during one of the episodes).

I was pleasantly surprised and extremely happy to find that in Pocket Monsters Best Wishes! Season 2, Ash was forced to crossdress again!


I was double happy that Dent joined him. I wasn’t too happy that there were a few people up in arms about the episode, but that’s a different story.

At first I wasn’t super sure how I felt about Ash’s newest disguise. His original crossdressing disguise has always been a favourite of mine. I was extremely happy though that actually bothered to give him a WIG this time (Diamond & Pearl’s maid outfit would have been my favourite if he had worn a wig). However, after staring at it for a while – I had it as my cellphone lock screen at some point and my profile picture on Facebook (so did my friends) because ASH’S BLUSH WAS JUST TOO DANG CUTE – it quickly became my favourite crossdressing disguise of his.

This prompted my first fan art of it a few weeks later.

Scanned Image 122940000

It was actually inspired by a doodle I did earlier to practice drawing it. Along with some Kotetsu (Cameron) practice and other things.


I don’t think Satoshi/Ash would EVER, EVER, EVER react this way to crossdressing. He doesn’t seem to be the kind of guy to ever get in touch with his [hyper]feminine side. He has nothing against it – it’s just not him. However, it’s one of those things an onlooker might look on with delusion because DANG he looks adorable.

Like really adorable.


After I sketched the image, I knew right away what kind of background it was going to have, what kind of effects, and that it was going to have text on it! It was going to have a dreamylike background, with some rather obvious “sparkling” diamonds around the Satomi (Ashley in the English version, I believe) disguise. I was going to overlay it a few times to make it appear to almost glow, to give it a dreamy-like effect. The text in the speech bubble had to be girly. I was hoping to use the one that Tokyopop used for the Tokyo Mew Mew logo.


I was (and am) pretty dang happy with this picture! I think the background came out well and very suited to the image. The text wasn’t quite what I wanted for feeling, but still works.

I’m really hoping people get that this is more of a joke or a comment on what I think of the disguise. I don’t use “kawaii” as an adjective unless I’m actually speaking in Japanese. Geez, I hate when people do that.

I have a few more of Satomi too that I think are potentially better than this one. I’ll get there though when I get there.