Passing is Hard, Failing is Easy

Just some random random snippets from my real life experience. Looking at all this, I am surprised to see how mundane most of this is.

* A friend, a wig mistress and makeup artist, offered to give me a makeover. How could I say no? My wife and I went to her boutique and she spent a good few hours with us teaching me tips and tricks. Then, we caught some cocktails and finally my wife took me out to dinner.

* It was my first date night, as a woman, presenting as a woman. I felt like I was walking on air. At the end of the evening, we were walking back to the car and we were stopped at a cross walk for a red light in Waikiki. A middle-aged Australian tourist was standing next to us waiting for the same light. He quickly scanned me and gave me a polite knowing giggle, I smiled and nodded back. The light changed. We crossed. Fuck! I had been clocked.

* A week later, again on Waikiki, I am walking with my wife and her childhood friend, visiting from the Mainland. I am wearing a sundress and, well, the whole deal, wig, purse, makeup, shoes. I am smoking a cigarette. “Excuse me sir, can I have a light?”

I look at the man standing next to me, fish into my purse, hand him my lighter while correcting him with the word, “Ma’m”.

“Ma’m.” he quickly echoes, lights his smoke and politely goes on his way. I smirk to myself, not because I am feeling content but rather because I took the opportunity to make that a teaching/learning moment.

* That same evening, my wife, her friend and I were on the lanai (a local, Hawaiian term for, “Porch” or, “Veranda”) at an open mic night, while watching the Moon slowly pass through the shadow of the Earth until it turned blood red. I struck up a conversation with the tourists sitting across from us, who lacked our view of the moon, and would remind them every time I felt they should take a look. They followed my advice and took every opportunity to look. No funny looks were exchanged. Pleasant goodbyes were shared.

* A friend took me shopping at a thrift store. They had unisex dressing rooms. I had to try on a bunch of dresses, to find a costume for a play. I would pop out of the room every time I liked a look to get more feedback. It was fun until…

I got a few too many disgusted looks from other customers. Finally, I had to go, I was getting a weird vibe. Fortunately, we found me a dress. Shopping is both frightening and fun.

* Went to Victoria’s Secret in drab (dressed as a boy). Shopped for a half hour. Nobody batted an eye. Fortunately I knew my sizes. No need to use a dressing room.

* Sang karaoke with my wife and friends. We had a blast. Still, it was odd picking songs. I have a pretty low singing voice. Thankfully, it was a LGBT friendly place.

* Rehearsed a monologue on the streets if Chinatown at night. I was so focused on my work, I didn’t care what anybody thought. Nobody gave me a second look.

* A friend of my wife’s came to Hawaii on vacation. I was not dressed in drab when we met he friend. I was probably more uncomfortable than he was. He did not seem to mind at all, in fact.





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