Christmas on the Ho Stroll

The streets were pretty empty of cars and foot traffic Christmas day though the emptiest day of the year was Superbowl Sunday. Nevertheless, hi there’s always business. Over the several years I was out there on Christmas day a single guy would pick me up bc he didn’t want to be alone on the holiday. Truth be told, neither did I. I never would have imagined anyone would look to a hookror true companionship but that tells you how little I knew about human interactions.

I met someone who was really into me, the same year I finished my stretch in prison. My belongings had been stolen by one if the many working girls or addicts that created a stream of traffic to an associate’s apartment. I split my time between five a low income apartments occupied by guys who traded their space for dope. My new client obligingly took me to Walmart because I needed foundation and other make up. I always needed foundation bc of my problem skin. This person understood my desperation to acquire make up without me having to go into embarrassing detail. I was grateful for the help. He gave me the makeup money and I made sure to spend all the money then return half the items so I could show a receipt proving where the cash went. I correctly guessed he would not compare the items I actually had to the documentation.

I returned to the car he showed me pictures of my legs taken with his phone. My legs were well toned from years of running track and running the streets. The Hawaii weather allowed me to show them to their best advantage. Short skirts and heels we’re a tad too dressy for Hinolulus relaxed style of dress but it wasn’t like I was trying to fit in to society. Prior too my breast augmentation my legs were my most attention grabbing feature. On the way back to his place he offered to let me stay indefinitely, and use his car to take my road test. I looked at the other pictures on his phone while he skillfully backed his car into the tiny parking space that came with his small $1200 a month studio. (Right outside of downtown he was grateful to find something for that price.) I was the only woman on his phone. The rest of the pictures were mahus, chicks with d****s. When I made my customary grand entrance without clothes I looked for the admiration I expected but saw only disappointment. He was no longer interested in sex or letting me stay for a bit. Then he withdrew his invitation to stay for the day. It was only after he dropped me off that I understood.

He had thought I was a guy. He wanted big black c**k and there was none. I consoled myself with the knowledge that I had money for dope from the Walmart make up money. I reminded myself of a standard phrase I often heard: the prettiest mahus are prettier than woman. That’s when I became determined to get money out of the 3 or 4 guys who picked me up every week and let me out after I had the wrong answer to “are you a boy or a girl?” But this Christmas, I was getting high and for right now, nothing else to worry about.


Published by Brainiac Meets Honolulu's Hooker Streets

In the early 2000's addiction took Caroleena, a recent ivy league college grad & private school teacher out of her Manhattan classroom & put her on the Honolulu hooker streets she once studied for a college project. Life as an addicted street level sex worker was in the same geographic location, but a world away, from her studies for an elite institution. Caroleena again finds herself at the far limit if her social class, not as a magna cum Laude grad but shackled to the next woman in a Hawaii prison. Caroleena's perennial oariah status yields a wealth of info that can only be understood when viewed from the seemingly contradictory perspectives that created the Expert Escort.

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