Web Service to Match Transvestite Men with Women Launched Demand for Girlish Men Who Understand Gender Differences is on the Rise

In front of me is Musasabi-san, a man in his twenties striking a deliberately cute pose. He usually works as a male office worker, but he is a cross-dressing enthusiast. While there has been remarkable media exposure of cross-dressers like Mitz Mangrove and Matsuko Deluxe, it is still not mainstream.

Matching web application “Cross-dressing and Girls’ Night Out Jojo” (hereinafter referred to as “Jojo”) connects people who love cross-dressing with partners who understand their hobby. There are many matching services for finding lovers or marriage partners, but what kind of users are using “Jojo”? We spoke with Musasabi-san, who is also a user of the web application, and Megumi Okamoto, the representative director of the operating company, Vent Huge Co., Ltd., and the operating representative, Hajime Hiiragi.

“Making a girlfriend who understands cross-dressing would of course be nice, but my main goal is to make friends with whom I can exchange cosmetic information and talk about fashion,” he said.

“I think being able to interact while being acknowledged for cross-dressing is something that wouldn’t have been possible before. It’s nice that there’s no temperature difference or prejudice against cross-dressing,” said Musasabi-san.

For cross-dressers, the greatest benefit is being able to openly share their hobby and have relationships. For Musasabi-san, cross-dressing is just a hobby, and his romantic interest is women. How do women who want to meet cross-dressers interact within the web application?

“When I’m at work, it’s hard to check messages (openly), so I check about three or four times a day, usually in the morning and after work. I exchange messages with someone I’m interested in several times a week, and I’ve even asked about how to wash wigs used for cross-dressing. Sometimes our messaging conversation goes on until late at night. Actually, there’s someone I’ve promised to meet up with soon,” said Musasabi-san.

 

The catalyst that led him to become deeply involved in understanding the hobby of cross-dressing was quite intriguing.

“A friend I share a room with was doing photography work with LGBTQ individuals, but initially, I had a negative attitude towards LGBTQ people. When my friend saw me like that, he said, ‘If you keep saying such things, life won’t be interesting,’ which became a turning point for me,” said Musasabi-san.

Later, out of curiosity, Musasabi-san visited “Studio RAAR,” a cross-dressing studio in Shinjuku, Tokyo, operated by the business company of “Jojo.” There, under professional guidance, he experienced cross-dressing for the first time. “Originally, I had small eyes, which was a complex for me,” said Musasabi-san, but he enjoyed the thrill of transforming himself through makeup and fashion. That’s how he got hooked on cross-dressing.

“When I first went out to Shinjuku Ni-chōme cross-dressed, I received a lot of compliments. I don’t often have such opportunities living as a man, but I realized that receiving compliments is emotionally fulfilling. That’s when the feeling of wanting to become even cuter began to grow,” said Musasabi-san.

While Musasabi-san usually goes without foundation, he now finds joy in watching videos and researching cosmetics information.

“Doing makeup when cross-dressing is enjoyable. When I first cross-dressed, I was amazed at how much my face could change. I was surprised by the latest makeup techniques,” said Musasabi-san.

However, the memory of last year’s “Miss Tsukuba Contest” at Tsukuba University Affiliated Komaba Junior High School and High School, which sparked controversy on the internet due to cross-dressing from a feminist perspective, is still fresh. According to Okamoto, there is a common attitude among cross-dressers.

“In the past, there were men who couldn’t cross-dress in their hometown, so they would come from other prefectures to (studios in Tokyo) just to cross-dress. In that sense, I think the awareness of cross-dressing in society has changed a lot in recent years. Men who have cross-dressed have respect for women.

By cross-dressing, they also realize how much time makeup takes and how uncomfortable it is to wear heels or skirts, which fosters respect and understanding towards women. From such first-hand experiences, they might understand not only the enjoyment but also the difficulty of being a woman. Additionally, nowadays, women tend to prefer gentle, sensitive, and aesthetically conscious men over overly masculine or rough individuals. Jojo might be good for female users as they can meet such men,” said Okamoto.

Indeed, Musasabi-san sometimes unintentionally received sexual attention from men precisely because his cross-dressing seemed so natural.

“Normally, it wouldn’t bother me, but wearing a skirt made me feel a gaze I had never experienced before. It’s hard to put into words, but I felt discomfort and unease. I realized that women experience discomfort due to such gazes from men just by going out, and I felt I needed to be careful myself,” said Musasabi-san.

Is it possible that the diversification of male consciousness and the changing image of men desired by women led to the birth of “Jojo”? Hiiragi, the operating representative, speaks about the characteristics of the service.

“Originally, we were holding matchmaking parties for cross-dressing men and women, which evolved into a web app service. By making it a web app, I think the chances of meeting each other increased. The user ratio is six cross-dressing men to four women.

As with regular matchmaking apps, it’s easier for women to find matches. You can choose your purpose within the app, and some people use it to find lovers while others are looking for marriage partners. Also, among female users, there are those who have a hobby of cross-dressing, so they seem to understand each other’s struggles and hobbies,” said Hiiragi.

Through ‘Jojo,’ Musasabi-san met women who understood his cross-dressing hobby. What about his real-life experiences?

“I’ve told the people I share a room with about cross-dressing. At first, they were surprised, but when I talked about cross-dressing, I started to hear voices around me saying, ‘I want to try it too.’ Recently, women’s clothing has become more accessible. I buy shoes online in foreign sizes. With the spread of self-checkouts, buying clothes has become easier. I usually buy women’s clothes at places like GU,” said Musasabi-san.

Just as Musasabi-san, a man, enjoys cross-dressing, there are also women who enjoy cross-dressing nowadays. It seems that among the users of “Jojo,” there are even women seeking cross-dressing men. Perhaps both cross-dressing and men’s fashion are now enjoyed like changing clothes. Musasabi-san expresses that he feels “spiritually saved” by Jojo. In an era touted as diverse, new waves are also sweeping through matchmaking services.