Hello There,
There is certainly no shortage of crossdressing themed fan art online, but perhaps one of the most frequently featured characters is none other than Pokémon's own Ash Ketchum! Ash was the Pokémon franchise's main character in the anime television series for almost two decades. With his go to catch phrase of "gotta catch 'em all" you'd think he'd be talking about Pokémon, not women's clothing! This post is the start of a new series I will be working on covering crossdressing fan art based around classic cartoons and media. So zip up those dresses and strap on some Poké balls because Ash Ketchum is gonna be doing some crossdressing, or should I say "Ashley Ketchum".
Let's start out by establishing that there is actually precedent for Ash crossdressing in the original anime. Over his twenty year span as Pokémon's protagonist Ash did actually crossdress several times for one reason or another. Be it to avoid the clutches of the evil team rocket, or to compete in a girls only Pokémon league, almost every new Pokémon generation saw Ash dressing as a girl for one reason or another.
Although often used for comedic effect, for those of us who were struggling with gender identity at a young age, it still left a lasting impression on us. Ash's crossdressing hijinks seemed to have had a lasting impression on many people it seems because there is a massive library of fan art depicting him crossdressed. He has even been dubbed "Ashley" by his fans, who see him as one of the most commonly associated cartoon characters with crossdressing. I know I certainly developed quite the love for "Ashley Ketchum" when I was young, because I was at a similar age, loved Pokémon, and could identify with a young boy trying crossdressing for the first time. So it's no surprise that many others have the same fondness for Ashley as I do.
Interestingly perhaps the most commonly featured dress in Ashley Ketchum fan art is one he never wore. While exploring the Sinnoh region he traveled with fellow Pokémon trainer Dawn. Dawn competed in Pokémon contests which were essentially shows designed to show off a Pokémon's beauty rather than using them to fight in trainer battles. When participating in contests, competitors would wear elegant outfits to compliment their Pokémon. Dawn would typically wear a pink dress with a white collar accented by little pink bows. This is the dress that Ash is probably most commonly depicted wearing interestingly enough. Perhaps it is the popularity of this dress that drives artists to depict Ash as wearing it, or perhaps it speaks to how popular Dawn was as a character. Maybe it's just an amazing dress. What ever the reason Ash has been depicted as being no stranger to wearing Dawn's iconic contest dress!
In addition to Ash frequently wearing Dawn's dress, Dawn is frequently depicted as being the one to either encourage Ash's crossdressing, or help him along in the process. Again this is probably due to Dawn's popularity as a character, or perhaps its just because in the end most young crossdressers just long for a friend to dress with. But Dawn's role in the "Ashley" crossdressing saga is well represented.
In addition to Dawn, Ash has had several female companions who have accompanied him across his journeys through the different Pokémon regions. To fan artists, it sure seems like there is no shortage of Poké-girls willing to indulge Ash in his crossdressing. His own mother Delia Ketchum even gets in on the crossdressing fun sometimes!
It's not just Ash's female companions that want to get in on the fun however, many of Ash's fellow male Pokémon trainers have shown an "interest" in his Ashley persona. Granted unlike the Poké-girls, these boys seem to enjoy Ashley more for her appearance than the act of getting her all dressed up. Ash must make quite the convincing girl, because all the boys seem to swoon over Ashley!
Ash certainly seems to have a lot of fun with his Ashley persona, and what could be more fun than dressing as Disney Princesses (ya'll know I'm a big fan LOL). Ashely just couldn't help herself and had to partake in some princess fun as well!
Interestingly enough a modern trend of Ashley fan art is to pair her with the Jessie from the villainous Team Rocket! Jessie has gone so far with Ash's crossdressing that she is even beginning to call him her daughter!
In addition to dressing up as Jessie's daughter, Ash has gone so far as to dress as his "mom" Jessie. Although Ash often seems to use dressing as his mother as an excuse to dress sexily, maybe some Oedipus Complex going on here?
Well there you have it friends, I've covered almost all the aspects Ash Ketchum's crossdressing fan art, or should I say Ashley Ketchum? He certainly seems to enjoy indulging in the joys of femininity, doesn't he! Given that throughout his tenure as Pokémon's anime protagonist he would periodically crossdress every few years, meant that generations of young viewers got to connect with a male character who wore women's clothes. For many, Ash may have been their first exposure to crossdressing, and with such a massive backlog of fan art online, the influence Ashley Ketchum has on many young crossdressers can not be overstated.
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