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Pokegal4life said:
Ash Ketchum from Pokémon. He has done this 4 times in the anime. The first time was in the episode "Pokémon Scent-Sation" when he cross-dressed as a young girl and went by the name "Ashley" to gain entrance into the Celadon Gym. He couldn't gain entrance to the Gym as himself because he insulted the perfume the Gym Leader had made. With the help of Team Rocket, he disguised himself as a young girl and requested a Gym Battle. The downside was that Pikachu recognized Ash even though he was disguised as a girl, and when Ash made Pikachu mad, he shocked him making his disguise fall off. He still got to battle Erika though, and he won the Rainbow Badge after saving Erika's Gloom from a fire. The second time he crossdressed was in the episode "Love at First Flight". This time he disguised himself like a female character that appeared in the episode named Juliet. The reason he did this was to help a male character named Romeo practice making a love confession to Juliet. The third time he crossdressed was in the episode "Tanks for the Memories" when he wore a maid outfit to help out Spring and Summer during rush hour at the Mountain Hut Maid Café because Brock was trying to help the other waitress, Autumn, bond with her Miltank, Ilta. Pikachu, Piplup, and Turtwig also wore the outfits and all four guys felt uncomfortable, whereas Dawn, Buneary, Ambipom, and Pachirisu loved wearing the outfits, (PROOF THAT DAWN'S PACHIRISU'S A GIRL!) The fourth and final time was in the episode "Beauties Battling for Pride and Prestige" where he crossdressed because Moria and her friends were insulting his, Iris', and Cilan's Pokémon, (mostly Emolga). The reason he crossdressed was because Iris wanted to get revenge on Moria and her friends for their awful comments, but men weren't allowed inside the building where the women rehearse. After battling all three of the women and getting her revenge Iris felt much better. Pikachu and Pansage also disguised themselves as girls. Pansage wore a red bow on the tuft on his head, and Pikachu taped a heart to his tail, (as you will see in the picture which also has Ash in his girl clothes and Ash's Snivy). He used the name "Ashley" once again, and Cilan used the name "Cilanor".
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