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My Jamaican Vacation

"My first time in Jamaica turned wild."

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Although I had never been to Jamaica before, I had heard stories about women, mostly white women, single or married, traveling to Jamaica to hook up with a young, dark Jamaican stud just for sex. I was one of those women, single, and needing something different and exciting.

I booked a week’s stay at an adults-only resort and packed my sexiest items for the trip, including my tiny bikinis that left little to the imagination.

I landed in Jamaica on a hot and humid day. The resort had sent a personal driver to pick me up at the airport. He was a tall black man holding a sign with my name on it. He was also quite handsome, dreadlocks and all, and he did not attempt to mask his eyes from looking me up and down. I felt excited about the attention.

His name was Alec, and after he loaded my stuff in the back of the Mercedes SUV to head to the resort, he said, “Miss Rhonda, why don’t you ride up front with me? You will be able to see the beautiful countryside better that way.”

I took him up on the suggestion. As we started down the road, Alec continued to look at me very seductively. I wore a summer dress that hemmed a few inches above my knees when standing, and even higher when sitting. Alec kept looking at my exposed thighs, and I felt excited about the attention this young and very attractive black man was giving me.

About 10 minutes into the 30-minute drive, Alec pointed out some beautiful points of interest by reaching across my body to the passenger window. When he was done pointing, he retracted his long arm from across my body and lightly ran his hand across the bare portion of my left thigh. I wondered if it was an accident or on purpose.

As the drive neared its end, Alec pointed out a few more points of interest. As he pulled back his arm, he rested his large hand on my left thigh just above my knee. Curious about his action, I did not remove his hand.

“I am not only a driver for the resort, but I am a certified masseur, and I would love to work on you, Jamaican-style,” Alec said, showing his gleaming white teeth with a smile.

My eyes locked on his smile as his words went through my head. When I lowered my eyes, I couldn’t help but notice that Alec had a very large bulge in his pants. Alec noticed me staring at his manhood, and he squeezed my leg. I felt very sexy about what was happening between us, and I had this thought about what a Jamaican-style massage was like. “I’ll think about it,” I responded.

Alec kept his hand on my thigh for the rest of the drive. When we arrived at the resort, Alec removed his hand from my leg, which made me feel a little disappointed.

The resort was beautiful, and so were the people. I was getting some serious looks from the men at the resort, both workers and vacationers, which made me feel good about myself. Once I got to my room, I unpacked, showered, and took a long, refreshing nap.

I awoke in time for dinner. I slipped into my white summer dress. This dress had a very high hem. I went braless and wore a dark green thong underneath. Since the dress was white and made of thin material, the shade of my thong and nipples showed through. As I walked to dinner, I got excited to notice I was getting more looks from all the men enjoying my attire.

The dinner was very good, with a couple of glasses of wine to wash it down. I was feeling great. After dinner, I went to an outdoor party and saw lots of people dancing and generally mingling. I had a couple of fruity cocktails, and I felt as free as a bird, dancing with myself as I put them down.

After ordering my third cocktail, I noticed a tall, dark man across the dance floor meeting my eyes. He was probably 6’3” or more, with a large physical build. At first, it was just a glance or two, but soon we were holding our gaze into each other’s eyes a bit more, with an occasional smile. Gazing back and forth excited me, and I began to feel butterflies fluttering in my abdomen.

I wasn’t bold enough to walk over to him, but soon I noticed him coming my way. He stopped in front of me and said, “Hi.”

“Hi,” I managed to say as I looked him over. At one point, I inadvertently found myself glancing at his groin in his tight white beach pants and the inexplicable bulge. As I broke my gaze from his package, I looked up to see him smiling at me.

We spoke a few words to each other, and when a slow song came on, he asked me to dance. When we got on the dance floor, he put his arms around me and introduced himself as Rafael. I told him my name was Rhonda. He was so gorgeous and perfect. Halfway through the song, we were in a tight slow dance embrace. I had my head on his huge chest, and he had his big arms around me, with his hands on my lower back and the top of my ass.

The dance ended, and another slow song started. We barely broke our embrace and started dancing again. If anyone saw us, they’d notice me looking into his dark eyes and laughing to some of the things he was saying. The thing I liked the most was how his hands moved lower and cupped my ass while we danced. I was completely absorbed with his sexuality and could feel a growing huge bulge pushing against my abdomen. I couldn’t believe how big and wonderful it felt. Before the dance even ended, my pussy went from moist to wet.

We chatted more at the bar, but the booze really got to me. I could barely keep my eyes open. I told Rafael that I enjoyed his company, but I had to go back to my room before I passed out. He understood, and we parted ways. I wished it hadn’t turned out that way. If I weren’t so drunk, I would have invited him to my room to spend the night with me.

The next morning, I woke up feeling froggy from the alcohol. It took me a while to get out of bed. I ordered an in-room breakfast. I needed food in my stomach, and I was starting to feel better after I ate. After eating my breakfast, I took a long, hot shower. The shower made me feel better still.

I was thinking of putting on my bikini to go out to sunbathe. But after drying off and brushing my hair, I noticed some water on the floor near the sink that wasn’t there before. I opened the doors under the sink and noticed a steady drip coming from one of the pipes. I called the front desk, and they said they would send a maintenance person to my room shortly.

For whatever reason, instead of putting on my bikini, I grabbed the luxurious terrycloth robe the resort provided, put it on, and waited for the maintenance person to arrive. The robe felt cuddly and was short, ending halfway down my rounded thighs.

It wasn’t very long before I heard a knock on my door. I pulled the sash of the robe tighter and went to answer the door. I opened the door and almost fainted when I saw Rafael standing there with a toolbox in one hand. He was wearing a maintenance uniform and looked incredible in it. I felt my legs get weak. I could barely speak, but managed, “My God, it’s you, my Mr. Fixit!”

Rafael saw my name on his work order, so he was not surprised to see me when I opened the door. Rafael, with a big smile on his face, said, “I am at your service.”

I smiled and stepped aside to let him enter. As he walked past me, he turned his head in my direction and did not try to hide his up-and-down view of me. He made me blush, and that fluttering sensation in my belly quickly came back.

After he entered my room, I shut the door and admired Rafael’s physique as he bent over to set the toolbox down. He turned and walked up to me. I felt anxious, wondering what he had on his mind.

“I hear you have a leak,” he said.

“Yes, in the bathroom,” I replied.

But instead of picking up his toolbox and making his way to the bathroom. He reached his arms around me and gave me a huge hug. Trembling, I reached up and put my arms around his neck. We looked into the depths of each other’s eyes as our lips slowly inched closer. My lips parted the moment his lips touched mine, and we kissed, using our tongues.

I felt Rafael reach down and put his hands on my ass over the robe and then whisper in my ear, “You look beautiful, Rhonda."

I felt my sex flood with excitement. “I’ll bet you say that to all the girls,” I said, not knowing what else to say. After I said it, I realized that it sounded stupid. But then, without saying another word, Rafael reached further down and put his hands under my robe and massaged my bare ass, one hand on each cheek. I stretched on my toes and mewled from his touch.

Again, without a word, Rafael lifted me, and the moment my feet left the floor, I instinctively wrapped my legs around his waist. I love strong men, and I admired the way he lifted me like a feather. We gazed into each other’s eyes before Rafael moved to kiss me again. And once again, I kissed him back, feeling overcome with sexual tension. We embraced and kissed passionately for what seemed like minutes.

While we were still embracing, Rafael walked over to the bed and laid me down with him on top of me. We kissed passionately for a few more minutes. Then Rafael let go of me and knelt up, still between my legs. I lay there with my legs spread with this amazing man between my thighs. This is what I went to Jamaica for, and I was now ready for anything he wanted to do to me.

Rafael took off his shirt, revealing a muscular and chiseled body. Then he untied my robe, and I allowed him to open it. He looked down at my exposed body and said, “You look amazing!”

He then came back down to kiss me again. His lips moved to my neck and down to my heaving breasts. He sucked, nibbled, and bit my nipples, causing several moans to escape my lips as I arched my breasts up to his mouth for more. I could feel his hard bulge pushing on my crotch, and I felt like I was in a dream.

After warming my tits with tingling sensations, he kissed his way down my belly to my pussy. He looked up to see me biting my lower lip and nodding yes to him. He kissed my pussy the way he kissed my mouth, first with his lips, then with his tongue probing its way into my pussy. My pussy went from moist to wet and from wet to dripping with excitement and pleasure. Within a minute of having his face buried in my pussy I had an amazing orgasm. Rafael trailed his lips back up my body to my face, and we kissed passionately again, his lips made sweeter by my juices.

Rafael then urged me up onto my knees. He removed my robe. We kissed again, and my hands roamed over the dark skin of his hard body while we kissed. Then I reached down to his bulge. I was amazed at how hard and big it felt. I reached my other hand down and undid his pants and pushed them down. We continued to kiss, and I reached down to grab the biggest penis I had ever felt. It was so thick I could not wrap my fingers completely around it, and it felt very long. Even with both hands, I could not cover its entire length.

“Would you like to feel this inside you?” asked Rafael as he watched me explore his ebony manhood with my hands.

“Yes…you need to fuck me right now,” I eagerly replied.

Rafael laid me down again. He got between my legs and pressed himself against me and ground on me while kissing me. Just the feel of his cock rubbing against my pussy nearly took my breath away. I looked down between my legs as my hips had a mind of their own, and I began to swivel my hips and push towards him, trying to get him inside me. I did not feel intimidated by his girth…not at all…I was excited by it!

Rafael didn’t disappoint and pushed slowly into me. I could not believe how big he was. I had never felt my pussy stretch like that before. I felt pain, and I felt pleasure. I was feeling so full, and my hips kept pushing to take more of him into me. He was only halfway inside me when I had another orgasm. Rafael stopped long enough to let me enjoy the surging waves of pleasure as my pussy convulsed around his cock.

His hands reached behind my knees and pushed my legs back further as we continued our erotic dance to get him entirely inside me. It took some work on his part, angling himself just right until he rested on top of me, completely buried in me. It was an amazing feeling to have a man so deep inside me. I felt his huge cockhead up against my cervix, which felt like the most pleasurable lightning bolt going through my body. I felt so full and couldn’t believe he was all the way inside me. But I was young, and sex was still rather new to me.

I ran my hands all over his body, taking in his masculine physique. I liked his masculine scent. I liked the salty taste of his sweat when I brushed my lips against his skin. His scent and taste were an aphrodisiac I wanted more of. He slowly began to move in and out of me, and in less than a dozen smooth slides of his cock, I erupted in a huge, magnificent orgasm, an orgasm that made me claw his back and scream aloud.

He lifted himself off of me, leaving only the head of his cock inside me, and I just looked up at him in disbelief. His dark skin glistened with sweat, outlining his thick muscles. He looked so sexy! We stared at each other, and then I opened my legs wider and said, “Take me again!”

Rafael didn’t hesitate and began pounding into me. I was literally drowning in euphoria. I felt that wonderful sensation in my gut again. I could feel every inch, every movement, and feel his cockhead banging my cervix and his balls banging my ass each time he went in balls-deep. I knew I was about to experience something amazing, and the anticipation was almost too much to handle.

I got into rhythm with him, and soon I was meeting his thrusts with my own perfect timing. “What is happening?” I thought. He grabbed my ankles and spread my legs as far as possible and pushed every last bit of his huge cock into me.

I began to scream, “Oh my god, oh my god, fuck me! Fuck me harder!”

And he did, sledgehammering my cunt. I had my last orgasm, and my juices were running down my ass and spotting the bedsheets.

He had fucked me for 20 minutes and was about to come. “Where do you want it?” he asked.

“I want it inside me,” I answered between moans.

He came hard, and I did as well when I felt his hot seed flood my cunt. I had no thoughts other than Rafael and giving myself completely to him. He finished and stayed on top of me. We kissed briefly, and he went limp and removed himself. I felt so empty without him inside me. We cuddled for a minute before I fell asleep.

After waking from my nap and realizing Rafael was not beside me, I began to think it was the most erotic dream I ever had. This was until I got up and felt his seed running down my thighs. I went into the bathroom to clean up. There on the sink was a note that read: “The sink has been fixed. Please let us know if you need any further service.”

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A large grin came over my face from knowing what kind of service he was talking about. I took a long, hot shower. Then I put on my bikini and went to soak up some sun on the beach for a couple of hours.

Now it was getting close to dinner time, so I went back to my room to get ready for the evening and see what the resort had to offer. I wore another cute sundress. This one was white, nearly see-through when the light hit it right. I chose to wear a pink thong under it. I wore sandals on my feet to complete my attire.

I had a great dinner. After filling my stomach with delicious food, I went to the lounge to relax and find someone to dance with. I kept scanning the lounge for any signs of Rafael. To my disappointment, he was not there. But I did notice Alec, my driver, walking around talking to the patrons. I got anxious as Alec got closer to me. When he noticed me, he smiled and walked straight towards me.

“Hi Rhonda, I hope you are enjoying your vacation,” Alec said while looking me up and down. He reached for me and gave me a long and powerful hug. “I am greeting patrons to see if anyone is interested in a massage.” Then he added, “Would you like a once-in-a-lifetime massage?”

“Maybe. What openings do you have?” I asked.

“How about 11:00 AM tomorrow?”

“Okay. Where do I go to get this once-in-a-lifetime massage?” I asked.

“I’ll come to you. I have your room number,” he said.

“It sounds good to me,” I replied.

Alec smiled and looked at me with lust in his eyes. “I’ll see you at 11:00 AM, Love,” he said and leaned in to hug me. As he hugged me, he patted me on the ass with his right hand. When he released me, he said with a wink, “It will be a massage you’ll never forget.” Then he walked off with a strut in his step.

I had another drink before heading back to my room. That night I could barely sleep with thoughts of Alec touching me. I also thought about the pounding Rafael gave me. I began to touch myself throughout the thoughts I was having. I couldn’t get over how good Rafael was to me and how I took all of him. I thought about the way I so freely gave myself to him. The way my hips and my pussy took control of my body. Stuck in my mind was Rafael towering over me as I looked down between my wide-spread thighs, watching his huge black cock rhythmically pound away at my pussy.

Before I realized it, I had my fingers buried in my pussy and moaning as an orgasm ripped through me. I pulled my fingers from my pussy and licked them clean. Now, feeling relaxed, I drifted off to sleep.

I woke up the next morning at 9:00 AM. I made some coffee with the small coffee pot in the room. As I sat at the table enjoying my coffee, I wondered what was in store for me today.

I was surprised to hear a knock at my door. I opened the door and saw a nice lady standing there holding a gift bag. The lady said, “Hi, this is a compliment from Alec.”

I reached out and took the bag, saying, “Thank you.” Then I shut the door. Of course, I was curious about what was inside. I opened the bag and saw a note from Alec. It read: “I am looking forward to our experience today. Here is something for you to wear so you don’t get oil all over your own clothes.”

I reached into the bag and pulled out a thin white silk robe and a pair of basically see-through violet thong panties. The thong was very thin and revealing. My abdomen began to stir again.

I went to shower and get ready, while asking myself questions. Should I wear a bra? Would I wear this outfit to answer the door? Is he bringing a massage table?

I finished showering and slipped on the thong panties. I also put on a pair of high heels. I felt exposed, but very sexy. I put on the robe that just barely covered the bottom of my ass. I felt even sexier when I looked myself over in front of the mirror, and I was becoming aroused.

I had about 20 minutes before the massage. I paced around the room, counting the minutes. A few minutes before 11:00 AM, I became very excited. I could see my hard nipples through the robe, and I was certainly feeling moist. “Relax, it’s just a massage,” I tried to tell myself.

Then came a knock at the door. My heart jumped, and my heels clicked across the hardwood floor as I hurried to the door. I stopped at the door, but hesitated to open it when I heard two men talking and laughing on the other side. Maybe it was Alec. Maybe it was someone at the wrong door.

I heard another knock and someone say, “Rhonda, this is Alec. Are you ready for us?”

Did he say “Us?” I was confused. I didn’t know what to think or say.

Then another knock, a little louder this time. With my heart in my throat, I reached for the door and opened it. I was speechless, for there in front of me were Alec and Rafael. Both men wore big smiles as they took in my figure in the skimpy outfit.

“Hi Rhonda, are you ready?” Alec asked.

“I…um…what are you doing here?” I asked, looking at Rafael.

“I am Alec’s apprentice. Giving massages is far better than being a maintenance man, well, except for yesterday,” he said with a smile.

The two tall Jamaican men walked into the room as I stood there with my hand still on the doorknob. Once inside, Rafael turned and shut the door. I wasn’t sure if Rafael was legit in what he was saying, or if this was some odd scheme to team up on me. Rafael then grabbed my trembling hand and said, “Relax, it will be okay.”

I said I had to go to the bathroom. I went in and shut the door behind me. “What the hell have I gotten myself into?” I thought. Did Rafael tell Alec about what happened between us yesterday? What if he did? With that thought, I calmed down and stepped out of the bathroom.

I immediately began to take in both men. They were dark, handsome, and rugged. I took a deep breath and sauntered towards them.

“Where’s the massage table?” I asked.

“We don’t lug them around anymore because most of our clients prefer to be serviced on the bed,” Alec replied.

“Serviced on the bed.” Those words were ringing in my ears.

Both men had gym bags and opened them. They both pulled out a pair of white spandex shorts that looked too small for them to wear. Alec noticed the puzzled look on my face, and he said, “We typically change clothes so we don’t get oil on our street clothes. Do you mind?”

“Fine with me,” I replied.

Alec went into the bathroom and shut the door. Rafael, standing about 10 feet away from me, slowly pulled his shirt off, proudly revealing his chiseled chest. Then, staring at me, Rafael pulled down his shorts, revealing his long, thick cock. My eyes locked on his manhood. Still fresh in my mind, knowing how it felt, I wanted it again, and Rafael knew it by the lustful look on my face. He teased me by slowly putting on the white shorts and tucking his monster cock inside them.

I could clearly see the giant mold of his cock through his shorts as I continued to stare. I let out a soft moan when Rafael reached down and squeezed his cock.

I was taken from my trance by hearing Alec stepping out of the bathroom. He wore only his tight white shorts. His huge chest, washboard stomach, and small waist were exposed. Both men were barefoot and wore only their shorts. I blushed to see them both smiling at me.

“Shall we?” Alec said, standing next to the bed.

Rafael took my hand and led me to Alec. I faced Alec as Rafael stood behind me. Alec was also tall in comparison to me. I was about chest-high to him. I just stared up at him, waiting for what came next.

Alec, standing silently and staring into my eyes, reached down and pulled the dainty lacy string holding my robe closed. I felt it fall open, exposing my heaving chest. I then felt Rafael step in close behind me and reach up near my neck and grab hold of each side of the robe. I shivered as Rafael slowly pulled the robe off my shoulders and took it from me.

Rafael moved my long, silky black hair aside, exposing my neck. He leaned in and gently kissed my neck. I closed my eyes and leaned back, melting into Rafael. I could feel his bulge on the small of my back. As Rafael nibbled my neck, I opened my eyes to see Alec still staring down at me. I seductively tilted my head up and slightly to the side, inviting him to kiss me. Alec leaned down and kissed me passionately on the lips. I knew then that there would be no massage. I knew because this wasn’t what I wanted. What I really wanted was sex in the worst way.

Feeling lust burning inside me, I reached forward aggressively and grabbed Alec’s package. I moaned into Alec’s mouth as I couldn’t believe how big it felt. “Could it be bigger than Rafael?” I thought.

Rafael reached around and pawed at my breasts. Alec reached down to my now-soaked panties. With both hands on me, he grabbed the sides of my panties and effortlessly ripped them, causing me to flinch a little.

My panties were now only held in place by the moisture between my sexy thighs. I reached down and pulled the panties away. I then reached back and grabbed Rafael’s bulge. I now had in my hands the two largest cocks I had ever felt. Filled with lust and excitement, I broke away from both men, kicked off my heels, and crawled onto the bed. Lying there, I slowly opened my thighs and said in a trembling voice, “Service me!”

The two men tortured me by rubbing their hands all over my body and gently nibbling everywhere. Rafael took my right foot between his hands and began nibbling and sucking my toes. Alec took my left foot between his hands and began nibbling and sucking my toes. It seemed like they were having a contest between them to see who could do it better. In the meantime, they were driving me insane!

Then, as if in a slow race, they both began kissing their way up my legs. At the same time, I spread my legs even more for them. They both arrived at my pussy essentially at the same time. They took turns kissing my clit, which drove me nearly over the edge. Then they shifted me so that I lay on my right side.

With them holding my left leg in the air, Alec was by my pussy and Rafael by my backside. Simultaneously, they began to kiss and lick my pussy and ass. The sensations were incredible to have one man licking my pussy and another man reaming my asshole. Needless to say, I erupted into a massive orgasm.

Now it was my turn to do something I had yet to do since I landed in Jamaica. I told them to lie down next to each other and take their shorts off. While they were removing their shorts, I darted into the bathroom to get a scrunchie to hold my hair back. I came back to the foot of the bed and seductively crawled up between them, stopping with my face between their cocks. I grabbed both cocks at the same time. Alec was actually bigger than Rafael!

I had a strong desire to pleasure both men with my mouth. I methodically began licking and sucking them one at a time. While giving them oral pleasure, I often looked up to watch their expressions. I was happy to see them smiling down at me.

After a while, my jaws were getting sore, and I knew I wouldn’t last much longer. So, I leaned up, resting on my knees. Then I lay on my back and opened my thighs. “Who wants to be first?” I asked with confidence.

Alec got up and climbed between my thighs. I felt the thrill of taking his big black cock when he slid his cockhead up and down my drenched slit. I felt the pressure stretching my introitus when he started to push into me. Slowly and without stopping, Alec buried his cock inside me. I grunted to take it all, but my grunt turned into pleasurable moans when he began fucking me.

As I was thrashing my head back and forth from Alec’s deep thrusts, I saw Rafael stroking his massive cock. I reached for him and guided his cock into my hungry mouth. All it took was having one cock in my pussy and the other cock in my mouth to bring me to a massive orgasm. I had never done two cocks at the same time before. It was a mind-blowing experience.

Right after my orgasm waned, the guys switched on me. I sucked Alec as Rafael banged me hard for what seemed like an eternity. I matched each thrust with one of my own. The three of us had worked up a sweat. I started coming again, and I felt like I was in an endless orgasm with Rafael fucking me the way he did. Each thrust sent a thrill through my body. Then, after a few more furious minutes of hard fucking, Rafael erupted deep inside me.

As Rafael and I came back to earth, I focused on Alec. I sucked and stroked him like a pro. When I got him super-hard, I told him I needed him to fuck me.

Alec smiled and told me to get on all fours. I quickly got up and got on my hands and knees. Alec moved behind me while Rafael was in front of me. Rafael’s limp and glistening cock was inches from my face. I grabbed his cock and began sucking on it, tasting the blend of my pussy juices and his cum. Then I felt the pressure of Alec’s cock penetrating me from behind.

I felt dirty and slutty and so alive with passion, having two men working me at both ends. I arched my back, pushing my ass in the air while I was getting skewered. I was experiencing the hottest, nastiest, most erotic sex of my life, and I saw the glory in it.

Deeper and deeper, Alec drilled his way into me. I began to suck Rafael with more vigor now and moaned the entire time. Soon, I felt Alec hit my cervix, and I came as hard as ever. Alec continued to fuck me, and between his hard thrusting cock and my orgasm, I found it difficult to focus on Rafael.

Rafael moved off the bed and let Alec do his thing. Alec stopped and rolled me over onto my back. I reached down for his cock and slipped it back into my hot, juicy cunt. He sank in and fell forward on top of me. I spread my legs wide, pointing my toes, and grabbed Alec’s ass with both hands.

“Fuck me, Alec! Fuck me! I want it all!” I screamed like a raging whore.

He began to fuck me harder and deeper than I had ever felt before. I screamed his name a dozen times and begged him not to stop. I was having a poly-orgasmic climax, something that I had never experience before. Alec, feeling the spasms inside my pussy, could not hold back any longer and flooded my pussy with his seed.

I felt so empty when Alec withdrew. I rolled over, exhausted, drained of all my energy, and dozed off. I woke up feeling hands all over my body. My nap was cut short after both men recovered and wanted more of me. We did it again, and it was even better than the first time. After that day, Alec and Rafael took turns to see me every day for the rest of my Jamaican vacation. I didn’t have to look anywhere else for a good time. I already had more than I could handle.

End of story.

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Written by Rhonda35
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