It was the winter of 2015. I was 23 and had just graduated from community college. I decided to reward myself with a week long trip to the Caribbean island of Barbados. I could write an entire book about all the incredible misadventures I had on the island, however, as I've been super busy lately, I have decided to share only the most exciting one.
*****
It was my fourth evening on the island. I was staying in the small resort town of St. Lawrence Gap. That night however, I had decided to attend the island's famous Oistins Fish Fry. It was about 8:00 at night by the time I arrived, and the party was in full swing. The atmosphere was lively, with local drummers and Bajan girls in mini skirts and tight undersized tops, twerking their large bums right in the faces of tourists having dinner. Some how, they managed to miss me. It was probably because I didn't give them a tip. But I needed money for the taxi ride back to my hotel, and I had already spent quite a bit on a large order of flying fish and beer, which had been taking forever to arrive. Finally, after 45 minutes I heard my name called. I picked up my meal and proceeded to find a place to sit. The place was so packed that strangers were being forced to share tables, a common practice on the island. I wondered around the party for at least three minutes, looking for an empty one. Suddenly, I heard a man's voice call out to me.
"My friend, come sit with me!"
I turned around to see a young, sharply dressed local guy sitting at a small table by himself.
"Thanks man," I told him. "I thought I would end up having to eat this on the beach."
"No problem my friend. This place gets really packed. Have a seat my friend."
"Thank you," I said.
"How are you doing my friend?" the young local asked me.
"I'm good," I replied.
"Welcome to Barbados," he said in a loud voice.
"Thank you," I replied, even though this was already my fourth night there.
"First time on our island?" he asked me.
"Yes first time," I told him.
"Ah, welcome, welcome."
"Thank you," I replied.
"Ah, flying fish and Banks beer, excellent choice mon! Where you from my friend?"
"USA," I told him.
"Oh USA. You like my island?" he asked me.
"Yes, it's beautiful," I told him.
"You like our girls?" he asked me.
"Oh yes!" I told him. "The black girls here are a lot hotter and sexier than the black girls we have in America."
"Oh yes my friend. Our women are the sexiest you'll eva find. You wanna meet one?" he casually asked.
"Excuse me?" I asked in a surprised tone.
"You wanna meet one of our girls? Because I have a friend. She would be very interested in meeting you. Just tell me which hotel you staying at, and we'll wait 'til all the tourists leave tomorrow morning, and I'll bring her up the gate."
"Are you serious?" I asked him.
"Yah mon. I'm dead serious. Just tell me the time and place."
I immediately knew he was talking about sex, but the whole thing seemed suspicious to me. No one simply offered a random stranger sex with their friend. And as I had come to learn over the past few days, nothing on the island was free. I figured this friend of his was a prostitute, so I thought I would just ask him straight up.
"How much will it cost me?" I inquired.
"Not a dime, mon!" he assured me. "Prostitution is illegal here. She's just a local girl looking to have some fun. What do you say brother? Tomorrow morning at 10:00. Just give me the name of your hotel and she'll be outside waiting for you."
"How old is she?" I inquired.
"She just turned 21, mon."
"Is she hot?" I asked the young stranger.
"Of course mon! I wouldn't offer her to you if she wasn't."
What the hell, this was my graduation trip and I was there to cut loose. Besides, I was a bachelor and had never been with a black woman before. The thought alone made my cock tingle.
"Alright brother, I'll do it." I told the young stranger.
"Excellent mon. I promise you will not be disappointed. I just need the name of your hotel."
"The Bajan Vibe, in St. Lawrence Gap. I'm not staying anywhere shabby," I told the stranger.
"Alright mon! I'll see you tomorrow morning. Enjoy your meal."
With that, the stranger walked off and left me to my meal.
*****
It was about 11:00 by the time I made it back to my hotel. The entire cab ride over, I had a raging hard on as I imagined the hot Bajan babe that would be grinding her pussy against my morning wood. The mystery of not knowing what she looked like, added to the excitement even more. As much as I wanted to save myself for tomorrow, I hadn't jacked off in a few days, and the last thing I wanted to do was humiliate myself by blowing my load early. As soon as I entered my room, I ran into the bathroom, stood over the toilet, dropped my shorts and began to stroke. I maneuvered my foreskin back and forth as fast I could, imagining that my hand was Rihanna's pussy. After only 30 seconds, I blew a large load of cum, which ended up coving parts of the wall, floor and toilet seat. I was now ready for tomorrow.
*****
The next morning, I took a shower and put on my nicest shirt before heading outside to meet my date. My cock was already semi-hard, as I stood outside the rusty gate of my quaint hotel. 10:00 came, and there was no sign of either the girl nor the young man. However, I wasn't worried as I had learned over the past few days that nothing on the island was ever on time. The anticipation was killing me though. I stood and waited constantly gazing at my watch. Ten minutes turned to twenty, then thirty, then forty. This was too long even for island time. By this point I was wondering if I had been stood up. I was thinking about just bailing on the whole thing and doing some more sight seeing. Then suddenly at 10:45, a black car pulled up to my hotel. The door opened and a tall, slim black woman emerged, carrying a large leather handbag.
I had some time to examine her as she slowly approached me. Her skin was the color of dark chocolate, and her wavy hair was as black charcoal, and ended just above her lower back. I couldn't see her eyes as they were covered by a pair of large sunglass. Her nose however was long with wide nostrils, one of which was pierced with a large silver bud. Her lips were full and coated in bright red lip stick. Off her ears, hung two large hooped earrings. Her large breasts were barely covered by a tiny black top, and I could see her nipples poking out, indicating that she wasn't wearing a bra. The tips of her long fingers were covered with turquoise acrylics, which were elaborately decorared with colorful beads. One of her fingers had a large turquoise ring on it. Her exposed navel had a long sliver chain hanging it from it, which stood out perfectly against her dark skin. Her hips and thighs were broad and were encircled by a large glittering belt, which had an elaborate silver buckle. Her legs, which were covered by a pair or ripped dark blue jeans, were as long as a giraffe's. I was 5'11'', and this girl must've been at least my height if not taller. I followed her blue jeans down to her feet. This was the only part of her body that was a bit of a turn off. Her purple toenails were covered in colorful elaborate beads, but looked like they hadn't been cut in months. I was really hoping they were fake, just like her fingernails. Her feet looked like a pair of pedicured dragon's feet wearing silver heels.
Good grief, who the hell did that guy sent me? This girl was way out of my league.
My stomach filled with butterflies and my cock grew another inch, as she walked towards me, sensually swaying her hips and thighs. As she stopped in front of me, she removed her sunglasses, finally revealing her large brown eyes, long thin eye brows, and long dark eyelashes.
"Good mornin', you spoke to my friend Kofi, yes? At Oistins yesterday?" the woman asked me in a strong Bajan accent.
"Kofi? Um, yes, I guess it was him. He never told me his name."
"Oh. Well I'm Braidynn. It's a pleasure to meet you darlin'."
"I'm Ryan. It's a pleasure to meet you too Braidynn," I told her as I lifted her hand up to my lips and gave her a European kiss.
"Um...is Kofi not with you?" I asked in a puzzled tone. "He said he'd be here."
"He had some business to attend to," she told me. "Oh hey cutie, you mind paying my fair for me? I left in such a hurry I forgot to grab my wallet."
"Oh. Yes sure, of course," I told the attractive young gal. "How much is it?"
"20 Barbados Dollars sweetheart."
"Okay, no problem at all."
I reached into my wallet and paid the driver.
"Thank you. Have a good time," he told me, as if he knew what was about to go down.