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Satoshi has certainly been prone to cross-dressing, as he has done it no less than three times now. He's usually had a good reason to do it though and I don't think he really likes making a habit out of it. He kind of tends to get forced into these situations. This page is dedicated to all the times he has cross-dressed.
Satoko
The most famous of Satoshi's cross-dressing antics, his Satoko guise. Upon arriving in Tamamushi City, he made it quite clear that he was not impressed with the girls' perfume and his bratty attitude caused him to get kicked out of the perfume shop. Not only was he kicked out of the shop, he was also banned from the gym itself. To get his badge, Satoshi had to end up working with Roketto-dan who also wished to enter the gym to carry out their latest devious scheme, so they pretended to be a family and Satoshi donned the Satoko disguise. He was able to enter the gym and meet Erika. Takeshi and Kasumi didn't realise that this shy little girl was actually their friend, but Pikachu did. Pikachu tried to hug Satoshi, who tried to reject his affections. Pikachu was unimpressed and blasted him with an electric shock, ruining the disguise and exposing him to everybody. At least Erika let him have his battle after all.
Julié This time, Satoshi didn't create an entirely new persona for himself. Instead, he was actually dressing up as a real person. Satoshi and company had just met two people named Romeo and Julié, who were having some trouble with their Volbeat and Illumise performance. The actual problem was Romeo, who had feelings for Julié and couldn't bring himself to confess, so Haruka came up with an idea to help him. She then asked Satoshi to do a favour for her, which he accepted. Little did he know at the time that this actually meant dressing up as Julié so that Romeo could practice confessing his feelings for her. Takeshi tried to help out at one point and then things got a little strange there. He apparently forgot it was Satoshi, and not Julié...
Maid
Satoshi, Takeshi and Hikari had come to the Maid Café, a place run by three sisters. While Takeshi went off to help the youngest sister who was having trouble with her own Miltank, Satoshi and Hikari stayed behind to help out the other two. It turned out they didn't have any outfits available for men, so Satoshi had to settle for wearing an actual maid outfit instead.
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