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Kaoru Oshima: Beyond Cross-Dressing Part Two

KAI-YOU - Original Japanese Date: June 28th, 2015
English Translation Published: January 25th, 2016

Kaoru Oshima is one of the most popular cross-dressers who ignited the dormant genre by starring in a slew of Japanese AV titles before retiring in June of 2015.

(Translator's note: This post is a continuation of a previous entry.)



KAI-YOU: Is it difficult being a cross-dresser?

Kaoru Oshima: Sometimes it's difficult to decide on which bathroom to use when I'm in public. I look female so if I sauntered into the male bathroom, I may end up surprising people who are in there. I've used both, but nowadays I actually do usually only use the male bathroom.

My first time using a female bathroom was kind of funny: I was entering the male bathroom when a surly old man who was washing his hands got angry at me. “Hey, women can't come in here!” he yelled in my direction. I replied back saying he was mistaken, but it was already awhile since I started cross-dressing and my voice was already in involuntary high-pitched mode. This made for a confusing situation.

I identify as a man so the few times I used a female bathroom were quite thrilling. I felt kinda guilty about it though. Now I prefer to take the most natural route when nature calls.

KY: Has there even been a time where cross-dressing turned out to be really beneficial?

KO: I found it easier overall to exist as a cross-dresser. Early on when I first started I was a bit perplexed with my sexuality. Was I gay? I'd peruse gay movies wondering about why men rarely had long hair or talked feminine. Later on I dabbled a bit with the newhalf industry, but even there I was met with some confusion. “Why aren't you taking any female hormones?” and “You'll be way more ladylike if you go through with castration” were some of the things full-fledged newhalfs asked of me. I didn't know why, but it was not something I wanted to do.

In the end, I decided I wasn't gay nor did I want to become a newhalf. Being a cross-dresser felt just right back then. Now? I'm not even sure if I can even identify as a cross-dresser any longer. I mean you can see pics of me on the net and when I'm shirt-less, I'm a man plain and simple. I never wear bras and frequently opt to wear regular boxers briefs instead of panties. It's hard to categorize myself as a cross-dresser because of this. If I wear female clothing nowadays, it's more by chance than anything else.


KY: Was there a time you felt very strongly about your natural-born gender?

KO: I definitely have a masculine mind. When I process thoughts, it's more about the facts than the emotions. I also find myself platonically bonding easier with men like when going out for drinks.


This image of Kaoru Oshima will cause a very confusing erection for many readers of My Dearest Desire.


KY: So did you have a time when you went from identifying more as a woman to more of a man?

KO: Romance can be an issue. I've dated women, but never any men. The hurdles to both are high for someone like me, but entering into a relationship with a man seems a lot more challenging. What's more, I'm attracted to 'weak' men. Guys who like to make themselves known are not my type. I like those who are somewhat pitiful, but still give it their all.


KY: Do you feel any maternal instinct?

KO: Maybe some, but I think what I feel is closer to that of an older brother looking out for his younger siblings.


KY: Have previous girlfriends had an easy time accepting you as their partner?

KO: I've only had one girlfriend since I began cross-dressing. She was something of a lesbian. Until me, she's never been with a man, but had an interest in those who cross-dressed. On some level she was not attracted to men so our relationship was kind of turbulent.



To be continued...

Interview by Koduck Kawaguchi


(Translator's note: encountering Kaoru Oshima in a male bathroom must be rather surprising. He seriously looks like and acts like a woman with very little to give his true gender away. Although there are many more cross-dressers on the scene now, Kaoru Oshima will always have a special place as being one of the genres pioneers.)

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Comments are disabled for this article.

  • thAkAm said:

    When did you realize there was a word for how you felt? or How old were you when you realized you were gay, and what triggered the realization?

    February 26th, 2016 - Reply


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