The single and most formidable barrier to enjoying nightlife in the Japanese capital is language. This is why a lot of the venues cater only to Japanese men and foreigners who are fluent in Japanese. Heads up for some Japanese 101: in Japanese, ‘gaijin’ means ‘foreigner’. If you read that a place welcomes gaijin and you’re a foreigner, it might be worth a visit.
This is important because bars and clubs are some of the most common places to meet ladyboys in Tokyo. Gaijin are welcome in most of these, and trans people here are very friendly and open-minded in general.
The city’s LGBT nightlife district is called Ni-chome. Some of the bars and nightclubs here are popular with ladyboys. Places like Gaspanic, Black Horse, and Motown are frequented by trans people as well. Of course, there’s no guarantee that you’ll meet anyone here. At any rate, you need to give it time. The longer you hang around, the better your chances of a meaningful encounter.
To improve your odds, drop by the Kingyo Roppongi. This ladyboy cabaret show has performances every night of the week. There is also a pub and a restaurant. The venue is popular with film directors, fashion designers, and other artsy types. Of course, there are always plenty of ladyboys here, both on and off stage. Performances are beautiful and powerful. You’ll be impressed.
There is a ladyboy bar called the Mirage Club in Tokyo, where you pay to meet and talk to a ladyboy. If you like each other, you can arrange a date. Then there are the theme parties, with BDSM and cosplay being recurrent themes. A lot of trans people go to these parties. The traditional Folsom Black Leather BDSM party is particularly interesting.
The organization Rainbow Events sets up and shares information about events involving the LGBT community. These include seminars, club parties, cooking classes, travel tours, sports meetings, and more. Check out their Facebook page for the latest events in Tokyo. All the events Rainbow organizes are popular with the local LGBT community, and attendance is free for all.
If all else fails, you can always turn to the internet. Actually, it’s something you might want to start with.