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/r/japan crossdresser

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Nov 30th, 2015
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  1. Looking for some advice, culture insight etc. sorry for the newbie post.
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  3. I'm an American guy recently graduated from college. I'm in Japan to check it out and visit a Japanese female friend who was studying at my college in the US. She and her sister (who I met before when she visited my friend in the US) have an apartment here in Tokyo. I'm staying at their place for the month that I'm here. It's cool to see them here; they're cool girls and seem concerned about making sure I'm comfortable here in Japan.
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  5. Friday night we were hanging out in the apartment and drinking. We were chatting a lot. They were being really nice and complimented me and such and they got talking about my eyelashes because they're long (they said they wish they had eyelashes like mine). The sister joked about wanting to put mascara on me. I told her to get her mascara and do it (I was tipsy). So that wound up happening which they thought was fun. That led to them asking to do my makeup, which I allowed them to (and more drinking). They got out all their makeup and dolled me up and we were all laughing about it. That led to my friend grabbing a dress out of her room which she gave to me (they thought it was the greatest thing ever). I obliged and it was all in good fun. They told me I almost looked like a real girl.
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  7. As the night went on, they got talking to each other (in Japanese so I couldn't understand) and were getting all excited. My friend explained that they wanted to take me out the next day for shopping for some girls clothes and give me a makeover so I can dress up like a girl more. They asked me if I liked the idea. I was feeling happy and enjoying the vibe so I said, "sure".
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  9. Next morning, they were totally serious about taking me out. I was a little more clear headed than the night before but I just nodded and went along with them. We went out to a little shopping area not far from the apartment. They showed me the first shop they wanted to take me to. It was underwear. I was pretty nervous, but theybwere cool and unfazed. They grabbed the frilliest, pinkest, "girliest" set there. Said we needed to make sure it's the right size so we can get more later. Took it back to the apartment, washed and dried it, tried it on and it fit fine. We headed out to Shibuya to do more serious shopping. We went into lots of shops, they had me try on stuff (I'm a little surprised shopkeepers didn't care). Every single time they decided on a piece for me, they insisted on buying. I offered to pay but they were so insistent that they pay because I'm their guest and that this is their gift to me. They did let me buy them a few little accessories, but that was it. Much of the time we were shopping, the conversation was about how much they liked giving me the makeover and also checking if I'm ready to spend the next coming weeks wearing my new outfits. They were having so much fun, so I went along with it all. They were talking about how they're turning me into a Japanese girl and how all the clothes we're getting are real Japanese fashion etc. they were all about the idea of me being a girl. They heaped praise on how good I looked in different clothes (I heard lots of "kawaii") and complimented on how well I fit. We were all surprised at how well I fit into everything (I am tiny by Western standards and apparently the ideal size for a Japanese woman). They took me to a wig shop and bought me two wigs, too. By the end of our shopping, we had amassed a ton of clothing. I can't imagine how much they spent. But they seemed happy to do it and just told me it's Japanese style to take care of their guest.
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  11. We got back later in the evening. They broke out the drinks, did my makeup and had me put on the different outfits. They kept heaping compliments about how I'll be a good looking girl. They also thanked me a lot for letting them make me over and agreeing to dressing like a girl for the next month. They asked if it was ok to introduce me to their friend to help with my makeover the next day (today).
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  13. After waking up this morning, having them put on my makeup and putting on an outfit we headed out. We met the friend who was very shy(?) at first but polite. She did seem quite impressed with the makeover. We went out for the first time with me as a girl. I did notice some looks, but no one gave us trouble. The friend thought the makeover was really cool and wanted to snap lots of pics with me. She knows a lot about makeup so we went to some makeup shops and she picked out a variety of items for me. Again, they refused to let me pay for anything. Even the friend bought some items for me. When I tried to pay she just insisted and just told me to enjoy it and think of her when I use it and to be pretty. I was able to convince them to let me buy them some makeup, but not much.
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  15. We went back to the apartment put some hair clips and scrunchy in my hair did my makeup with the new stuff we bought, told me about some items, and picked out an outfit for me to wear. She seemed to be having a blast and said she loves giving makeovers. We went out again, had dinner and coffee and so on.
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  17. And that brings us up to now.
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  19. tl;dr: American male staying with female Japanese friend. She and others gave me a makeover into a girl. They bought me lots of clothes and makeup etc. They want me to be a "girl" for the next month while I stay with them.
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  21. Questions:
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  23. How normal/strange would my friend's (and the other girls) be considered? Is it normal to love makeovers this mich and do girls often give guys "female" makeovers?
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  25. Is it common/expected that they'd pay for all my clothes and makeup? It seemed like a lot. (Though I know they have money).
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  27. Is crossdressing accepted or tolerated fairly well in Japan? I know it's not a progressive place. But I didn't get distinctly bad vibes. And my friend and her sister seem to think it's quite cool, as do their friend.
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  29. Considering they lavished all these clothes and makeup and wigs and such on me, would it be expected that I follow through with wearing it all for the next month?
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  31. Will it be a big deal out in public if I do just dress as a woman?
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  33. Any other insights or thoughts relevant to culture? Anything I should be aware of relevant to this being in Japan? Of course, there's just the humans bring humans aspect. Just wondering if there's anything to think about beyond that.
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