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


Adult Services Provider Tells How She Put Ads Online and the Results

I will continue the story I began in the previous post. In 2013, i was at a low point in my financial life and due to incarceration circumstances I did not know how pervasive the internet had become in life. A client I met while working the streets of downtown Honolulu referred me to a nation wide site for “hobbyists/mongers” and “providers.” I could invent a user name (what I called my stage name), post non-identifying yet sexy pictures, an email address and guys would get in touch. He assured me that if I continued to exercise and maintain my “all-star” body I’d be beating ’em off with a stick. I was sure to be as successful as I was in the late 1990’s and early 2000’s when, according to my wristwatch, one or more drivers bearing cash pulled over for me in less than a minute after I hit the street. The online sex market had largely replaced the open air sex market on the street.

Later I found out that the same person who praised my figure and guided me along the way was working with several different user names. One of them was my advocate, but one of them hated me. The persona who hated me did not have complimentary things to say about my body at all, and did all he could to sabotage me by saying I was unattractive, unskilled, late, boring, crazy, you name it. The one guy who always made sure my contact information was current online did not have a positive voice about me that was anywhere near as adamant as the voice of hatred.

Why would someone play games like this? I figured it out when I recognized phrases he had said to me in our sessions written under the hateful screen name and the nice screen name. He demanded to know why I thought it was him, but he did not demand the same honesty of himself. When I posted a blog about what he did, he created a new screen name that had never appeared before and wrote about me in the “Rip Off section of the adult web site, as if being with me was such a bad experience it was akin to a rip off. Someone wrote and thanked him for his feedback and assured him that I would not see that person either. Now that I think of it maybe everyone who had opinions, maybe all the heated debates about providers, maybe all the interest–was just one or two people with nothing to do but create an imaginary world that was all about discussing providers

Or–maybe there were just that many people who had things to say about me. Sure this guy invented a few names but maybe everyone else was really out there. Mercilessly evaluating every step and misstep I took. I learned from reviews that if a guy says “that’s ok” he often doesn’t mean it and the thing that he reassured me about would be the very thing he blasted me for. Oh well. Comes with the territory.

I could say at least they are talking about me. However, I do not believe that all publicity is good publicity when it comes to internet customer reviews. Anyone have a different experience? As for my question about why someone would be an internet friend and also an internet troll–I never got an answer and I doubt someone like him can ever admit to lying. I don’t think I will ever know they reason why.

So the owner of the New England Patriots Might Have Wanted to Hire a Hooker… what’s the problem?

What’s wrong with a wealthy man seeking some p****?


My beloved, late friend was a retired army medic who did two or three tours in Vietnam. I originally met him in a professional way, you now what mean, but the relationship evolved into something more, as all relationships do with extended contact. In this case the something more was real friendship. He was very accepting of me, I see that now, and of people in general. He didn’t judge people and their idiosyncrasies. Here is an example. He often spoke of Bill Clinton and Monica Lewinsky:

The whole world laughed at our country for making s big deal out of that. If the president of the greatest country in the world can’t get no p**** in the Oval Office , there’s no hope for the rest of us.

My friend’s view was that men are dogs and there’s nothing that can be done to change nature. I’m sure he would have the same opinion of the latest so-called scandal involving the owner of this year’s Superbowl winner. Why in the world would anyone put prostitution on the same list as murder as we see in above cartoon? So the man wanted p****? After all, if he couldn’t get it there isn’t much hope for the rest of them, as my friend would have said.



Secret Keeper/Secret Teller
I tell hidden personal truths while maintaining perfect confidentiality so you may see secrets you share!

Clients confided in the Ivy League educated hooker–me. Why? I was smart enough to understand anything they shared. Equally important, my status as social outcast meant even if I told their secrets few would listen to me. Of those who listen, few of that small number would believe me.  Almost no one would care what a woman of ill repute had to say. I understood their secrets and kept those precious gifts safe since I couldn’t tell on them even if I wanted to!  Of course, I did not want to unlock the vault and violate trust.  I said nothing and remembered what I heard.  learned that many men lived in shame BC of the erroneous belief that they were different than others. They did not know that their confessions had been echoed by others. I had a friend who lived his whole life never fully accepting himself BC he thought he was uniquely weird. He was wrong. His alienation was unnecessary pain. If he knew what I knew his life could have been happier. The only way I can form a community out of shared secrets, mostly sexual, but not entirely, is to tell the secrets while maintaining perfect confidentiality. My blog tells of my experiences with the emotions and musings of people in the sex industry now, and in my past (up to 15 years ago). The purpose of every post is to comfort to at least one person with the assurance that someone else felt/thought the same way. The feelings and thoughts are true, the people and events combine interviews, personal experience, and fiction. You cannot meet Caroleena bc she does not exist beyond this site. But she speaks truth. Sometimes your truth. You are not alone with your secrets. Come, let me show you.