I have a very odd fetish/question

[werebearsnow]

I'm a shy, quiet, awkward skinny Asian.

First question: Is there any place in Tokyo that would dress me up as a girl (I'm a bit of a pretty boy, but not gay). No sexual favours included is fine. I've also never crossdressed before.

Second question: Same as the first one, but some play is involved. Preferably with a young girl taking the lead. I'm also a virgin, so if she wants to anal me, I hope she knows what she's doing. No bondage. I just like girls who are aggressive (like pushing me down and grinding the PSY on my face.

Sorry if this seriously creeps some people out. But I've had this fantasy for a long time and was wondering if Tokyo could cater to it.

Please also state prices, thanks.

Edit: Forgot to mention I speak little to no Japanese.

 

[italianguy]

I'm a shy, quiet, awkward skinny Asian.

First question: Is there any place in Tokyo that would dress me up as a girl (I'm a bit of a pretty boy, but not gay). No sexual favours included is fine. I've also never crossdressed before.

Second question: Same as the first one, but some play is involved. Preferably with a young girl taking the lead. I'm also a virgin, so if she wants to anal me, I hope she knows what she's doing. No bondage. I just like girls who are aggressive (like pushing me down and grinding the PSY on my face.

Sorry if this seriously creeps some people out. But I've had this fantasy for a long time and was wondering if Tokyo could cater to it.

Please also state prices, thanks.

personally i have never done stuff like this so i dont know a lot about this service in tokyo. but i stumbled across this website:http://japanese-fetish-femdom.com/concept.php

its located in yokohama
they offer anal, facesitting, etc. im pretty sure there are some young ones among them. i dont know about crossdressing tho. mybe they'll do it if you request it when booking

EDIT: just saw they offer this service also near shinagawa

 

[Hofmeyer]

I'm no expert, but I think the BDSM term is "sissification" where you are dolled up. Usually it includes verbal domination about how you make a pretty girl but if you're not looking to go that far that could be negotiated I suppose. I think it's one of the standard options at BDSM venues so I expect you could request it.

 

[vck_js]

Is there any place in Tokyo that would dress me up as a girl (I'm a bit of a pretty boy, but not gay). No sexual favours included is fine.

http://raar.me/
This private salon in Shinjuku does wonderful make-up. Megu, the girl running it, is a former top hostess who now organizes crossdressing events, she is very skilled and a lot of Tokyo crossdressers use her service when they go to an event or play outside dressed as a woman.
Make-up+hair set is 6500y, I think you have to provide your own clothes/wig (if you have short hair).

https://www.operatheprincesshouse.com/price/
This place is in Shinjuku Marui (the men one), it's more like a studio where you'll have your make-up done and be dressed to have your picture taken as a souvenir, so outfit and wig will be provided. Even though it's advertised as "for everyone", the owner Milktea is a crossdresser and actually almost all customers are too.
For a "normal girl" look, it's around 10000y. A bit less expensive if you go for the catgirl look, a bit more expensive if you go for the princess look.

Both are reservation only.

For play, most SM services have a crossdressing course where the girl will first do your make-up/dress you up (you don't have to provide anything - unless you want to use your own stuff) and then abuse you. Of course make-up will not be as good as when done by professional MUA, but if you plan to have the girl sit on your face it will be ruined quite fast so who cares...

 

[TAG Manager]

http://raar.me/
This private salon in Shinjuku does wonderful make-up. Megu, the girl running it, is a former top hostess who now organizes crossdressing events, she is very skilled and a lot of Tokyo crossdressers use her service when they go to an event or play outside dressed as a woman.
Make-up+hair set is 6500y, I think you have to provide your own clothes/wig (if you have short hair).

https://www.operatheprincesshouse.com/price/
This place is in Shinjuku Marui (the men one), it's more like a studio where you'll have your make-up done and be dressed to have your picture taken as a souvenir, so outfit and wig will be provided. Even though it's advertised as "for everyone", the owner Milktea is a crossdresser and actually almost all customers are too.
For a "normal girl" look, it's around 10000y. A bit less expensive if you go for the catgirl look, a bit more expensive if you go for the princess look.

Both are reservation only.

For play, most SM services have a crossdressing course where the girl will first do your make-up/dress you up (you don't have to provide anything - unless you want to use your own stuff) and then abuse you. Of course make-up will not be as good as when done by professional MUA, but if you plan to have the girl sit on your face it will be ruined quite fast so who cares...

Great information, thanks for sharing!

 

[scorpioni6ths]

Second question: Same as the first one, but some play is involved. Preferably with a young girl taking the lead. I'm also a virgin, so if she wants to anal me, I hope she knows what she's doing. No bondage. I just like girls who are aggressive (like pushing me down and grinding the PSY on my face.

most S&M service (that I've experienced are soft) ... and you are not technically allowed to touch or pleasure the girl. you can ask permission from your mistress though.

I've only used the service below ...

personally i have never done stuff like this so i dont know a lot about this service in tokyo. but i stumbled across this website:http://japanese-fetish-femdom.com/concept.php

they're almost everywhere ... the person that answers the phone can speak English ... but the girl you get/choose might only be Japanese speaking. you'll still have fun even if the girl doesn't speak English since they carry a laminated card showing the options, also the person on the phone can relay all your requests to the girl beforehand.

the top tier girls (ones with S, AAA, AA, A beside their names) might be able to speak English ... but they have added fees.

enjoy!

 

[Anon12345]

personally i have never done stuff like this so i dont know a lot about this service in tokyo. but i stumbled across this website:http://japanese-fetish-femdom.com/concept.php

they offer anal, facesitting, etc. im pretty sure there are some young ones among them. i dont know about crossdressing tho. mybe they'll do it if you request it when booking

Going through the profiles on the site, on the アイテム画像 (item images) tab some of them have clothing marked as お客様着用アイテム (items for the customer to wear - http://www.bbquest.net/gravure/g3143.php), 女装 (crossdressing) or 男性用 (for male use - http://www.bbquest.net/gravure/g3231.php), so at least some of them offer it.
If you have time, you could go through them with CTRL-F and see which ones specialize in it.
Rikaichan (addon for Chrome/Firefox) can come in handy if trying to decipher things.

I think I remember few of them having some makeup equipment as well, but no names come to mind at the moment.

 

[werebearsnow]

Wow, thanks for all the help! I'll look into these options.