Running Away To Conquer The World.

After leaving the Immigration Department, I applied for a job with the airlines. That job didn’t last very long either. One day, I was caught by the General Manager driving the company van to the supermarket to buy groceries—when I was supposed to be on duty. My immediate supervisor had actually sent me there to do her personal shopping. Naturally, she denied it, and I took the fall. Ironically, she and I are now close friends, but we’ve never talked about the elephant in the room.

Still, I was happy to have worked at the airlines. It felt like the perfect launchpad to travel the world and chase my big dreams. As a boy, I always dreamed of going to Los Angeles to see where the movies were made.

My grandmother—on my mother’s side—had one of the only televisions in the neighbourhood. It was black and white, but it was magic to me. Kids from all over the village who didn’t have a TV at home would crowd around her window to watch whatever was playing. I was lucky. I got to sit inside, comfortably in a chair.

“One day I gine tuh Uni Uni Universal Stu Stu Studios where dey mek de de de mo mo movies,” I’d say, in my thick Bajan dialect, with my severe stammer. I stuttered terribly, especially when I got excited or angry. It used to frustrate the hell out of me.

In my early twenties, I taught myself how to control it—through breathing techniques and mind tricks. I knew I had to overcome the stammer if I wanted to seduce the world and become financially successful. I couldn’t afford a speech therapist, so I spent hours in front of the mirror practicing until I learned how to speak without stuttering. As my vocabulary grew, I learned to swap out difficult words on the fly. Most people never noticed.

Still, my dream of going to Hollywood was the running joke of the village. The other kids laughed until their stomachs hurt. How could a broke little boy from a tiny village in Barbados ever end up in Hollywood? That was the big question. I was determined to find the answer.

A few days after losing the airline job, I was on a flight to New York for the first time. I was 20 years old and dead-set on leaving Barbados for good. I was going to stay with a woman I met while working at immigration. Well… woman might be a stretch. She was suspected of being a prostitute, denied entry, and scheduled to be deported back to Guyana.

I was the lucky officer assigned to monitor her while she waited for her return flight. She was stunning—killer body, seductive eyes. But when she walked into that arrival hall dressed like a sexed-up movie star, she may as well have had “PROSTITUTE” stamped across her forehead. If you’re travelling to a foreign country to work the streets, Rule #1 from the Whore’s Training Manual is: Dress like a respectable housewife or nerdy college student. Annette clearly missed that memo.

We hit it off surprisingly well. Once she knew deportation was definite, she admitted she was on her way to the same brothel where Martina worked. This wasn’t her first trip to Barbados either—she’d come before, under a different name and passport.

Before boarding, she leaned over and whispered, “Do you want to fuck me quickly before I go back?”

Let’s be clear: prostitutes are masters of charm, deception, and seduction. That offer was definitely not free. Even in custody, Annette stayed true to the hustle. I wanted to take her up on it, but I didn’t have enough money on me. I did get her phone number in Guyana, though—and a freebie. She made me so horny I couldn’t let her leave without a blowjob and a quickie. That happened in the toilet in the Immigration section of the airport. Real talk.

I walked her onto the plane when it was time to go.

We kept in touch by phone after she got home. To my surprise, a few months later, Annette made it to New York to live with relatives. She invited me to visit anytime—said she’d soon have her own apartment. That promise would later prove to be a comfort to a fool.

I arranged the trip and flew out. She told me exactly where to wait at JFK. But of course, she never showed. I spent 24 hours in the airport before catching the first flight back home. I slept on the floor, but it wasn’t too bad. At least it was warm inside, and I wasn’t the only one sleeping rough.

Two days later, I returned home tired and just as broke as when I left. The flight felt twice as long, weighed down by embarrassment. The thought of everyone knowing I got stranded at JFK was torture.

But I wasn’t ready to quit. I needed money fast, and the only way I knew how was to hustle pool games for cash. What I hadn’t said before was that my grandmother’s rum shop had a pool table, and I played every day after school and on weekends. By 12, I was so good I started hustling grown men. My Uncle Jim saw my talent early and became my pool P.I.M.P. He took me all over the island to bars and rum shops to hustle grown-ass men out of their money. I’d win hundreds in a few hours, but Uncle Jim only gave me fifty bucks each time. Still, I worshipped the man.

Soon, I was feared on the local circuit. Only a few players in the entire country would even bet money against me.

I found some more suckers and, within days, had enough for another ticket back to New York. This time, I made it past the airport and as far as Brooklyn.

It was November 1982. Freezing. I didn’t own a winter jacket—I’d never left the Caribbean before. I stepped out of JFK and immediately cursed myself. “I must be fucking mad to leave Barbados to come to this cold-ass country.”

I barely had enough money to rent a cheap room for a few days. My survival instincts kicked in. I knew I had two options: charm a woman for food and a warm bed or find a pool hall to hustle. Everything I learned in Barbados was about to be put to the test—and I failed miserably.

Three days later, I was broke and homeless again. Back at JFK, waiting for the first flight home. By now, people probably thought I worked for American Airlines.

The pool sharks in Brooklyn were killers. Way better than I expected. And the only woman I hooked up with was a big, loud Puerto Rican chick from the pool hall who fucked the life out of me on my last night. I never even got to see her front door.

So back to Barbados I went.

This time, I knew I needed a proper plan. I decided to hustle daily until I had enough to support myself in the U.S. for at least a month. I also collected names and numbers of relatives from New York to California, just in case.

Around that time, I reconnected with Kate, a sweet girl I met back in secondary school. Her mother adored me. Her father wanted to kill me. To him, I was a heartthrob troublemaker out to steal his daughter’s virginity—and he wasn’t entirely wrong. I loved Kate, though. She was one of the very few women I truly fell for.

We got close again. She’d just finished school and was already working. I was at her house all the time, sometimes even sleeping over without her dad knowing. Her mom knew but kept our secret. She just made me promise not to get Kate pregnant.

One day, Kate said her relatives in Boston invited her to college—and she wanted me to come with her. I told her they’d never agree. She suggested we get engaged to show everyone we were serious. So we did. Quietly. At St. James Methodist Church in Bridgetown. The preacher even blessed the ring.

We told her parents. Her mom was overjoyed. Her dad looked like he was planning my funeral.

The day of departure came. Kate arrived at the airport with an entourage of 50 relatives and friends. I came alone in a taxi. The contrast between our lives stung deeply.

After an emotional goodbye, we boarded. By now, I knew most of the AA crew by name. Shame I wasn’t getting frequent flyer miles.

We landed in New York. Kate’s family was waiting like a SWAT team. They hustled her into a car and sped off, leaving me standing there with my suitcases. That was the last time I saw Kate—for years.

Now alone again, I called an aunt in Brooklyn. She had a tiny apartment, so I slept on a mattress on the floor. But it was warm and better than JFK’s floor.

After a few days, I moved to the Bronx to stay with another aunt. Her son Derrick was my age, and this time I had my own bed. I finally unpacked. For the first time in three months.

Life in the Bronx was fun. Derrick took me everywhere. I made lots of friends. We hit clubs and bars weekly. Sexy girls were everywhere—but for some reason, I wasn’t getting the same attention I did in Barbados.

Truth is, I didn’t really like most of the girls I met in New York. Many already had kids and were looking for a man to support them. Others just wanted a baby daddy or money for drugs. The classy ones—especially the Black American girls—weren’t falling for my Caribbean charm. They’d been burned too many times.

Then came the night that changed everything.

I was out clubbing with my boys. Tipsy on scotch and ginger. The music was hot, the women hotter. Then I saw her. The most beautiful girl in the room, dancing alone. Her body was a sculpture—perfect curves, hypnotic moves.

She looked at me with lust in her eyes. That “this pussy is yours tonight” look. She gave me a nod. I finished the rest of my drink in one gulp and I slowly danced my way over to her, never skipping a single beat or losing eye contact. I also had great dance moves back then. I was also “good fuck”. The way she was looking at me there was no need for words. I went up closer and pressed my body against hers while maintaining her rhythm. Although she could see I had an erection, I wanted her to feel it. I put my head close to hers and I could feel her breathing on my face. Then we held each other and started grinding slowly to the music. There is nothing more romantic and seductive than two people grooving to slow jams.

I put my lips against hers and we kissed. At first it was light pecking of the lips and then it became passionate. Our tongues were in and out of each other’s mouth so many times, I was not sure which one was mine. I had never been so turned on in my life.

The club was packed yet we were alone in our own passionate world. She really knew how to turn me on. I never had an erection like that in my life, before or after that night. My cock was so hard that at that moment I could cut diamonds or glass with it. It was also uncomfortable as my jeans were very tight. There were no stretchy Armani jeans in those days.

Ingrid from childhood rape experience would have been proud of my erection. It was definitely a lot bigger that night.

All that time we said absolutely nothing to each other. I did not even know her name and I did not care. I was definitely going to fuck this woman -  back at her place, in the back seat of her car, in the bushes or in a dark corner of some lonely alley.

As I was about to pop the “Your place or mine?” question, my cousin grabbed me from behind and pulled me away from her. He shouted with an uncontrollable grin on his face, “Stop Charlie! That is a man you are kissing” 

At first I could not understand why my cousin was trying to stop me from getting laid finally by the hottest chick in New York. His warning did not register at first.

It turned out that the sexiest woman I ever met was a transvestite. She, he or it was well known to everyone in the club, except me. My cousin and friends were watching me make my moves and were literally on the floor in stitches, laughing at me.

When I realised what my cousin was telling me I was so angry and confused at the same time. “How could this be? How could a MAN turn me on like this? Am I gay and don’t know it? I thought to myself. 

“Should I punch out this fucking man or take him home and finished what I started? I wondered.

I was so embarrassed. I left the club a very angry and confused soul. For the first time in my life I had doubts about my own sexuality. Although my cousin told me that many other straight men were fooled by the same person, this experience affected me for years. I made my cousin swear not to tell anyone about that encounter.

For the next 20 years I did not have the courage to share my first and last homosexual experience with anyone.

Soon after I left the Bronx, I had overstayed my visa. I was now officially an illegal alien. But so was almost everyone else I met. When engaging in conversations, no one gave their correct address or real surname. This topic was taboo. To ask a West Indian or Puerto Rican for their real name was a sure way to end a perfectly healthy conversation.

One day I was walking with a Jamaican buddy whose nickname was Trigger. All of a sudden, we were attacked by four Puerto Rican guys. They had knives and baseball bats. I was all set to run when Trigger grabbed me firmly by the arm and said in a strong Jamaican accent, “Hey Rasta! Hear wha uh sey. We nuh run from nuh white boy! Me ga show dem why dem call me Trigger. Ya ear?” Trigger sounded like he never left Kingston.

Without hesitation, he pulled out a gun and started shooting indiscriminately at the unsuspecting Puerto Ricans. There was absolutely no fear in Trigger’s eyes. The poor boys ran for dear life and by some stroke of luck managed to escape without being shot. How on earth did Trigger manage not to shoot any innocent bystanders was a fucking miracle. He was so angry that he did not see the blood of the Puerto Ricans, I was afraid he would shoot me instead. For the rest of the day, he kept repeating, “Me nah like to waste good bullets. Scene!”

I later learned that the incident was gang related. Trigger and the other guys who attacked us were members of rival gangs in the Bronx. What was even scarier, I was now expected to join Trigger’s gang. It was the kind of invitation you did not refuse if you wanted to stay alive. 

As far as the Puerto Rican gang was concerned, I was a member of Trigger’s crew anyway so I had two choices. Join the gang or leave New York. 

So I left.

A few days later, I was on a Greyhound to Miami. Over the next three months, I journeyed to San Francisco, Monterey, Palo Alto, and finally—Los Angeles.

Yes, I did go to Universal Studios. And yes, I still have the ticket.

Fifteen years later, when I visited Barbados, I showed that ticket to the same guys who used to laugh at me when I said I’d make it to Hollywood.

Guess who had the last laugh.