Oh said the cars were described as "painful" because it was either "painfully embarrassing to be seen in one" or "painful on the wallet" because of the cost of decorating them.
A professionally decorated car with your favourite anime character can set you back upwards of $1500.
"It is not just about sticking a few anime characters on the car, but it is about turning the vehicle into a skilful work of art," Oh said.
"It is actually considered the ultimate form of otaku expression."
Oh said the availability of colour stickers and lower cost of decoration have helped spread itasha craze.
"In the past, people had to paint their cars and that can be very expensive and time consuming," he said.
With exteriors covered with stickers or illustrations of female anime characters, the cars are out to grab attention.
Jacky Qin's has plastered his black 2007 Toyota Blade with his anime idol "Haruna".
"I do it because I like her character, she is gentle and warm, and I like showing her off," the 22-year-old student said.
Qin, an anime and manga fan of six years, spent about $1500 engaging a graphic artist to put the design together.
He was thrilled that there was finally a venue to show off his vehicle and an event for like-minded itasha fans to meet.
Another owner, 19-year-old Nich Xu, has had her 2001 Toyota Alteza covered with Vocaloid characters.
Xu said she considered the car as an extension of herself.
On her Facebook page, Xu writes in reference to her car: "I don't have a girlfriend and I don't need girlfriends because I've a fiancé."
Itasha cars are believed to have started in the late 1990s, but have lately experienced a resurgence.
The meet tomorrow will also include an itasha design demonstration, and giving owners a chance to chat and show off their decorating talents.