There are all kinds of men in the world, but I have arbitrarily decided that the kind of man that wants to try wearing women’s clothes at least once in his life are in the majority. I’m not talking about becoming a cross-dresser for life, but most guys would like to see what it’s like to go around in a dress at least for a little bit, right?

I am one of those men! In my 33 years on this earth, I have long thought that just once, I would like to proudly declare my desire to dress like a woman, and at long last, I seized my opportunity this Halloween to girl it up, and as a result I learned 16 things that men would never know unless they walked a mile in a woman’s shoes.

1. Being told you are pretty or cute is cause for extreme happiness

Everyone likes to be complimented on their appearance, regardless of gender. Although you might make a modest show of refusing the compliment, on the inside, you feel like jumping for joy.

So, guys, if you know it is going to make a gal feel this way, why not shower her with compliments? I’m going to make an effort to do so in the future. It’s such a simple thing and it will give the lady such unadulterated happiness!





2. Being called a tranny, gross, or called out as a man is really upsetting

While being complimented is quite nice, on the flip side, being called ugly or a tranny or a dirty old man is upsetting. I laughed it off, but inside, I felt like crying.

Another big shock was hearing passersby comment on our group of three dragsters, loud enough for us to hear. That was hurtful. If you have to say something, fine, but couldn’t you at least lower your voice?





3. Dealing with leg and armpit hair is more problematic than I imagined

I decided to go with some cute fishnet stocking, but the sight of my leg hair sticking out from the holes in the fabric hedgehog-like really upset my fashion sense, so I decided to give shaving my legs and armpits a shot and discovered what a complex operation it is.

I slathered on shaving cream and went at the hair with a disposable razor, rinsing it off in a bucket of water between strokes. This went on and on, until I’d gotten every last strand of hair, a process that took almost 2 hours! I can’t believe women have to do this every time their hair grows in…

4. There is a compulsive need to check a mirror to see if your hair and makeup look OK

Of course, I had makeup and a wig on, but I was constantly wondering whether the makeup had gotten smudged or the hair was out of place. I would try to catch a glimpse while on the escalator or on the screen of my iPhone as I turned it off.

Has my makeup come off? Is my lipstick all right? Is my hair getting tangled…? Whether you are wiping away a bit of sweat, blowing your nose, getting something to eat, or taking a drink, you have to think about all these things. I finally understood why women are always sneaking glances at their compact.

5. High heels are seriously hard to walk in

If you want to be sexy, high heels are the way to go, but when I put on a pair and tried walking down the street, I very nearly ended up on my face! Even places that looked perfectly flat were actually more like crumbling cobblestones. It was like some fiendish punishment designed to torture!

After a little bit of practice, I was able to move about, but my feet were nearly at the limit of their capacity for pain. My toes were all scrunched up in the toe of the shoe and running would have been a complete impossibility. I couldn’t even keep up with an average walking speed. So, gentlemen, if you are escorting a lady, be sure to moderate your pace.



6. “Nice sandals” are amazing

OK, so the heels were just too painful, so later I went to a women’s shoe store to look for something else. Something that was feminine but would still allow me to walk at a fairly brisk pace. And what I found was a nice pair of nice sandals.

This is actually what they are called in Japan: “nice sandals”, or sometimes “office sandals.” They are actually meant to be worn inside, but you can also wear them out if you are so inclined. They were great! Even if I wasn’t dressing as a woman, I would want to wear these.





7. Going out during the day to take the train was embarrassing

You know how if you are at a graveyard and the sun starts to set, the atmosphere totally changes and you get that feeling that you really shouldn’t be here right now? Yeah, going out in drag during the day kind of feels like that.

On the streets of Tokyo, people might think “Here comes a weird tranny” and give you a sideways look, but they will largely ignore you. On the train, though, there is a real lack of entertainment, so you can expect to get stared at and receive some double-takes. I tried to stand by the wall as much as possible and look inconspicuous, but it was fairly embarrassing.



8. Nighttime feels much safer, as do gay districts like Shinjuku Nichome

Whether you are gay or in drag (or both), you are bound to let out a sigh of relief entering the bounds of a place like Nichome. It suddenly feels much safer and friendlier. In fact, without really even thinking about it, you naturally make eye contact with passing comrades in drag to say hello.

While on the train I was fidgety and uncomfortable, I felt right at home in Nichome. It’s really a friendly place for everyone.





9. You just feel kinder

I’m beginning to think the answer to world peace is to just have everyone dress as women. Somehow, when you put on a dress, you just feel a bit kinder. It’s like your pupils dilate and any aggressive urges just pass.

Even just trying for more feminine movements and tone of voice makes you immediately feel like your male sense of self disappearing and you are becoming someone else. You might call it a drag “trip” in the drug sense, because it kind of affects your body in the same way.

10. It’s more than just the clothes

You might think that getting feminine airs is as easy as putting on a dress and a wig, but it turns out there’s a lot more to it.

Even something as simple as the word “I” is different from males to females in Japanese, so I had to constantly think about how to refer to myself. Or sometimes, I would sit down in what I thought was a ladylike way, only to find my knees popping open. Or my walk would get very bowlegged if I wasn’t paying attention. There’s just so much to think about! Femininity is hard.

11. Going out without makeup is unthinkable!

This is something else I never really understood before. Why are women always so loathe to be seen without their makeup? Now I know it’s because the makeup is a disguise. In the instant that my makeup failed me, the 33-year-old man dressed in drag would be revealed, and I definitely didn’t want that.

And it’s not just a makeup-free face women are afraid to show. They don’t want to be seen really chowing down on something either, for example. In short, they don’t want to show anything less than a completely put together, prepared face to the world, and I totally get that now.

12. Japanese photo booths are awesome, but possibly soul crushing

Taking pictures in general is fun, but Japanese photo booths are in a whole new category of enjoyment. You can make your eyes bigger, your skin whiter, even erase wrinkles! And of course, add all kinds of cute embellishments. We found one of these dream machines in Nichome and decided to give it a try.

But even on the highest setting for retouching, you could still catch a whiff of tranny about me! I thought it would be the most adorable photo of me ever taken, but I was shocked and disappointed to see an old man dressed in drag.

13. Deciding which public toilet to use requires some courage

Dressed like a woman, but actually a man. So which restroom to use? Of course, as a man, I didn’t feel like I could use the women’s toilet, but I didn’t feel really comfortable just strolling into the men’s either.

It would probably shock the other patrons, and besides that, being in a feminine state of mind, I didn’t really want to use the men’s room! In the end, I decided to use a unisex bathroom at the convenience store. Thank god for those!

14. Much like Cinderella, midnight brings a transformation: facial hair

Somewhere I heard that a man’s facial hair grows at 10 a.m., so I was sure to get a clean shave after that. But by the time evening rolled around, I was already sporting a aptly named 5 o’clock shadow. Seeing it the mirror was something of a shock and the first thing I thought was perhaps it was time to call it a night.

Reflecting on that experience, the second time I dressed as a woman, I plucked out my beard using tweezers. It took more than 2 hours to get all of those pesky hairs, but then I could be sure I was hair-free for a least a couple of days, with no Cinderella beard to bring an early end to festivities.

15. When someone says they thought you were a woman, it sends shivers of pleasure up your spine

Being told you are pretty or cute is nice, but the queen of compliments is being told you are a convincing woman. Even more than if a woman says it, if a man says it, you are likely to be so pleased you respond with, “Really? You can touch my breasts if you want!”

I want to look even more feminine, even more beautiful. I want to think of myself not as a man in drag, but as a beautiful woman. What if I spent more on cosmetics? Gradually, you begin to think about these things more.

16. After dress up time is over, you feel empty

Dressing as a woman was unexpectedly intoxicating, but I couldn’t stay like that forever. Going back to my usual self was kind of sad, though. I took off the makeup, removed the wig, traded my dress for my usual men’s clothes, and thought, “Well, that’s that.”

It was rather dreary to look in the mirror and find the usual boring face reflected back at me. I almost wanted to cry. So if on the street one night you should happen to meet a man in drag, so long as he isn’t doing anything bad, please just let him be.

See also: A Simple Approach to Understanding Women: a Japanese Guide



[ Read in Japanese ]