Ivy League X-Streetwalker in Honolulu

Transgender–Me? Part I

Inquiring Minds Want to Know


When I was young, I don’t remember knowing the word transgender. Now the word is a part of public life. Transgender is a word that has become a part of my personal life, and I couldn’t be more surprised.

I Have Always Been Female and I never had to say so on the mainland United States

A former associate named Ross said he knows somebody who knew Caroleena in California when she was a man,” a gossip said to his girlfriend– right in front of me–just yesterday, March 30, 2019. He watched for my reaction. I did not give him a reaction. Disappointed, he went back to muttering to himself and ignoring his girlfriend while she regaled me with a list of complaints about him. I listened to her with half an ear but my mind was preoccupied by speculation about this man’s motive for repeating this gossip about me in front of me. In Hawaii, if you ask someone if she is really a man it’s possible that you are voicing a legit question, not trying to offend. It is not unusual for men to become mahus and in the drug addict “community” I would say one out of five women is really a man. When I worked the streets downtown I was asked at least one hundred times by potential dates if I was a girl or a boy as soon as I get it into the vehicle that had pulled over for me. I was confident I had the right answer, but many times the driver’s expression changed from expectant to disappointed. “Nevermind, that’s ok I’ll pull over so you can get out. Oh! Here’s $20 for your time,” the kinder drivers would say before we had gone two blocks. I was glad to get the money for nothing but rejection was embarrassing even if no one was watching me climb out of the car before the driver took the usual, ”mauka” (towards the mountains) turn that signalled the new, temporary couple was heading for a rendezvous spot in the vehicle or at his residence.

Two, No Three, Reasons for the question

The Honolulu street level sex worker scene is known for being heavily “staffed” with the unconventionally gendered, so to speak. But there were reasons I, personally was singled out and asked if I had been s lifelong female. I had devoted myself to exercise. This practice has left me with the physique commonly seen in workout videos. Ok, I am flattering myself. I wish I looked like I might’ve starred in a Beachbody video. Not quite. I am not all that, but it’s unheard of for a female addict to have great muscle tone.. Hawaii is not an exercise Mecca. Obesity is normal and pretty much ok. Island locals have regularly mocked me for being unfeminine and ocd. But educated east coast women like me would find me quite normal.

I’m not just fit. There are those who would say, I’m pretty. A double whammy.“The mahus look better than the women downtown,” I heard many times. Years of using drugs can take its toll physically and spiritually. Women “out there” give up on being pretty. I’ve seen it–women’s complete reliance on proferring what’s between the legs to earn money for the next high. Make up, styled hair. Who cared? Women on the street were watching their looks fade, especially the ice smokers with their rotting teeth. Mahus were just coming into their looks. They cared about their looks, and I cared about mine, especially my teeth. In my youth, and even in my more mature years “out there,” men considered me pretty. If I did not get one compliment every day, I felt distressed, bc I hadn’t gotten my second fix. I exercised st public parks and used public bathrooms for doing drugs AND brushing my teeth.“You’re not like the other women down here. You take care of yourself. That’s why I wasn’t sure about you” one client had said as an apology for asking if I was a “real” woman. I basked in what I perceived as praise. I never expected that the traits I valued were the same characteristics that made people question me. Those are two reasons people are asked. I believe I know about a third reason.

I never expected that the traits I valued were the same characteristics that made people question me. Those are two reasons people are asked. I believe I know about a third reason.


Men asked then, and continue to ask this day, if I am a man or a woman not just because they think I might really be a man. They HOPE I am a man. They are voicing a desire not a doubt.

If only out had d*** to go with that pretty face. You’d be perfect.”

–wistful words of a disappointed man before asking me to exit his vehicle

I will share my theories. Stay tuned for more in Part II of “Transgender–Me?” Find out more about what men hoped for and the complex reasons why they wished I was really a man.

Love, Caroleena, May 2, 2019

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