Spring Break Massage in Jamaica

When I look forward to what I would want my life to be like, I find myself looking back to one of my most adventurous vacation experiences. When I was in college, I got invited at the last minute to a spring break trip to Jamaica. I had a group of "party friends" that were, you know... a little more wild than the friends you would introduce to your everyday friends, or tell your family about when they ask how you are doing at college.

One of the girls that was supposed to go on the trip had to drop out with only a few days to spare, and so the other girls were desperately trying to find someone else to take the spot. I was in a weird place at the time, as I had just broken up with my boyfriend, and I was barely getting through a particularly stressful finals week. Under normal circumstances, I probably would have thought better of going with that particular group of girls, but in my vulnerable state of being pissed off about school, and of course being on the rebound, I said, screw it. Let's see what wild girls do on a Spring Break.

The trip down was a blur. When I finally got settled in the hotel, I just needed to decompress. My friends were already starting to drink and were planning a big bar crawl. I just couldn't quite get to where they were at after the week that I had just had. I drank a few drinks but still couldn't get totally in the spirit. I decided to take a walk on the beach to clear my head. I put on a tank top and some jean shorts and took the elevator down to explore the resort where we were staying.

When I made it down to the beach, I got bombarded by a bunch of people trying to sell me stuff. I was a little overwhelmed at first, but then one guy caught my eye. He was standing near what looked like a little grass hut, and I could see a massage table behind some curtains. Perfect, I thought, I could really use a good massage.

I walked closer to him and then purposefully made eye contact. He began to approach me. He introduced himself and offered to show me the massage area behind the curtain. He was a local Jamaican, with bright eyes and an amazing smile. From what I could tell with his shirt still on, he had a pretty good body. He took me back to the massage area and told me to "get undressed" which I wasn't sure exactly what that meant. He left the room, so I lifted off my tank and unhooked my bra, and then I pulled down my shorts. I was left wearing just my black lace thong. I wrapped myself in a towel and layed down on my stomach on the massage table.

At this point, I had just my shoulders exposed. He stood in front of me and started rubbing my shoulders and neck. His hands felt big and strong. He began to move the towel down so that he could massage more of my back. I instinctively lifted up so that the towel would slide lower. His hands ran down my spine and stopped just short of my thong. His hands then ran up my sides and gently grazed the sides of my breasts. He repeated that motion several times as I melted into the massage table. My drinks from earlier were kicking in, and for the first time, I felt like I was on vacation.

During one of the passes down my spine, I glanced forward and realized that his package was just inches from my face. From what I could tell, he looked big. It reminded me of a past encounter with a black guy who I could barely handle. The memories from that experience came rushing back. Suddenly, I was having scandalous thoughts surging through my brain about this new guy. The logical side of me knew that these were just rogue and inappropriate thoughts, but the naughty side of me wanted to stop the massage, take off this guy's pants, and guide his massive black cock into my mouth. I quietly continued with the massage, embarrassed that I let my mind wander to such a dirty and depraved place. I would never allow myself to give in to such a carnal, inappropriate urge.

He moved around the table so that he was approaching me from behind. He continued with the back massage for a short time, and then ventured down to my legs. His hands rubbed over my hips and then went hard down the backs of my thighs. I couldn't help but to lift off the table a bit as he stroked down my legs so assertively. He grabbed my calves and then laced his fingers around so that he was holding the fronts of my ankles. His touch felt confident. He began to rub circles around my ankles in a way that I never imagined could feel so good. He stroked his palms over the bottoms of my feet and pressed his thumbs into my arches. He eventually made it to my toes, pulling playfully on each one.

Suddenly his hands were heading back up my legs, with his fingertips pressing into my skin as he worked his way up my calves and thighs. He paused as he came closer to the edge of my butt cheeks, as if he was seeking permission or waiting for a sign that he could proceed. I obliged by reaching down and pulling gently on the towel, exposing more of myself to him. He continued the motion of removing the towel, so that I was in just my lace thong, and he left me there, uncovered and vulnerable, waiting for his next move.

He repeated the motion of running his hands from the backs of my calves, up my hamstrings, and over the sides of my hips and butt, until he was wrapping his hands around my waist and then pulling down again. I was of course rather voluptuous, and I could tell that he was appreciating the difference in size between my thin waist and ample hips. I found myself getting more and more wet with each pass of his hands. I tried to hide my increasing desire, but I found it harder and harder to play it cool. My rather dramatic figure had made me a target for attention from black guys in the past, but for some reason this time, I couldn't blow it off and gain the upper hand. He had me squirming and begging for more.

I found myself wishing that he would gently tug down on my thong until it was sliding past my hips, past my knees, and then falling off around my feet. I wanted his fingers to wander to my most delicate parts, so that he could feel how wet I was for him. I tried to gather my thoughts. Was there something going on between us, or was I just being tortured with crazy thoughts? I wondered if he had ever done anything like this before. If we did take it to the next level, would we get caught?

How was it possible that logical, reserved, good girl me was actually considering letting some random Jamaican guy fuck me during a massage? That would be something my wild girlfriends would do, and then brag about after. Granted when I came down here I said I wanted to party with the party girls and see how the other half lived, but currently those girls were all still in the hotel room having a comparably tame start to their vacation, while I was ready to give myself to some dude on the beach who I didn't even remember his name.

I somehow managed to center myself by thinking about the ridiculous irony of my wild friends being good girls back in the room while I was down on the beach. I was determined to enjoy the rest of the massage like the normal, classy, arguably boring white girl that I was. Then he repositioned himself so that he was behind me, practically on the table with me, pressing hard into my backside so that he could rub my upper back and shoulders again. I swore I could feel every inch of his manhood pressed against my butt cheeks. My plan to play it cool went up in smoke, just as I had tried to catch my breath and regain my composure.

The feeling of him pressing his massive cock against me was more than I could handle. I couldn't help but lift my hips off the table as I imagined him sliding every inch of his dick into my dripping wet pussy. I let out a little moan just thinking about it, as he continued with the back massage. My heart was racing. I was overcome with thoughts of everything that I would let him do to me. My pussy throbbed as I imagined him allowing me to get to my knees so that I could present myself to him. He would pull me to the edge of the table and pluck my thong out of my ass. One of his hands would hold me around the waist while the other hand would guide his long member slowly into my tight vagina. Although I had never had anal sex before, I decided I would let him fuck me anywhere, if it meant that he could satisfy the desire that was now burning uncontrollably in me.

I didn't care if this guy was notorious for doing this kind of thing with unsuspecting white girls every day of the week. I didn't care if my friends found out that I was down here on the beach letting this guy fuck me in the ass and pussy. I didn't care if the whole world knew that I was a huge slut that let herself get fucked by a total stranger. Clearly, I was no longer going to be able to reason my way out of this situation. His bold move to get up on the table and press himself hard into me had sent me down a one-way path. I knew then that I couldn't settle for anything less than getting fucked right there on the table.

He made one more pass with his hands over my shoulders and down the center of my back, pausing for a moment with his thumbs on my spine and his fingers laced around my ribs. He gave a slight squeeze around my narrow torso and then got up off of the massage table. I tried to focus, as he was starting to say something. He wanted to know if there were any other areas that I wanted him to rub. I couldn't just ask him for what I really wanted, but I had to keep it going somehow. I quickly flipped over, exposing my neglected front side. I playfully pretended to cover my bare breasts as if I was shy, as he reached for the long lost towel. I asked if he could finish the massage by rubbing my chest and stomach.

He smiled and went to the top of the table so that he was working from above my head. His strong hands started at my shoulders, but now with a focus on my collarbones. With so much previous attention to my back, it felt quite different and vulnerable to have the massage come around to my front. I found myself breathless, as I could tell he was testing the waters, slowly pulling on the towel and gauging my comfort level with exposing my breasts again. This was my chance, I thought. Show him that he can see every inch of you.

I pulled on the towel and let it drop into the sand. I raised my arms above my head so that my breasts would perk up for him. He cautiously ran his hands from my collarbones, down the sides of my boobs, and on to my stomach. I couldn't help but to raise my knee up in excitement. I squirmed on the table as I thought about what might happen next. I smiled as his hands moved lower, but then he paused as he got to the top of my thong. I could feel my heart beating fast. "Lower", I whispered. His fingertips gently lifted the delicate lace edge of my thong. He continued with the massage of my chest and stomach, again holding back when his hands returned to the top of my thong. I couldn't handle the suspense of wondering what it would be like when he finally touched me down there. I gave out a little moan, imagining the bliss of that first taste. It was enough of a signal for him to go even lower with his fingers, as he touched well under the fabric of my thong. I lifted up my hips and fought every urge not to throw my arms around his neck and somehow climb on top of him. He made one last pass over my chest and sides and then barely paused at all as his fingers found their way under my thong and to my most private of parts. This was it. This was the moment I had been waiting for.

My head was swirling and my heart was beating out of my chest. I felt dizzy in this uncharted territory, with intense feelings of desire and shame juxtaposed inside of me, wondering if he could see the battle that was occurring between my mind and my body. Not helping the situation was the fact that my body was literally dying to be touched by the time he finally made his move, so it was absolutely electric as he began to play with me. I was dripping white hot and his touches were only making me hotter and wetter. It wasn't going to be long before he had me coming, even just from a mere graze of his fingers on my pussy.

I arched back as I felt the sensation intensify. I looked down and watched his long, dark fingers disappear inside of me. He slowly pulled them out and lifted up until his fingertips found my clit. He delicately stroked higher and then back down, repeating that perfect motion until I couldn't even breathe. My mind was still spinning over the fact that here I was, giving up my dainty white pussy to this man who was bringing me to orgasm with just a few soft touches. My whole body began to tremble. I couldn't believe what was about to happen, but then there I was, trying to stifle the sounds as I came right there on the table.

I tried to gather myself. Did that really just happen? How loud was I? Did anyone else know what was going on over here? Then I realized that at that point, I really didn't care. We were firmly down the path of being wild. He owned me. After all, I was willing to completely give myself up to him after having known him for less than an hour. Why overthink it now?

I slowly flipped over and crawled to the end of the table where he was standing. I got up on my knees and leaned in to kiss him for the first time. He smiled as my lips met his. He then grabbed my hips and sat me down on the edge of the table so that I could wrap my legs around his waist. We kissed even deeper as I pulled him in closer with my calves. Our tongues played back and forth before he wandered down to kiss behind my ear and down my neck. My hands found his belt buckle, which slid open easily.

I could feel him smiling through the kisses against my neck as he helped me unbutton his shorts. I reached down into his boxer briefs and pulled it out.

... Jesus.

It was bigger than I had expected. I had a split second of doubt, wondering if I could even fit it in my mouth, wondering if I would have to resort to just licking it. I didn't realize that my jaw had literally dropped when I saw it for the first time, and so he was now kissing my chin and jaw as my lips remained parted.

I decided to play with it a bit first, just to try to wrap my head around how I was going to handle all of this. I was feeling quite vulnerable in this scenario now, a seemingly innocent white girl, now in too deep with a black man who had brought more to the party than I ever expected. But he was responding to my touches in a way that let me know that he was just as hungry for this encounter as I was. His reactions were giving me the confidence to do more to him.

By this point I was already moving down to the sand, suddenly feeling drawn to my knees. This move of mine centered his manhood right in front of my face. My mouth slowly fell open. Being down so low, off of the table, felt very submissive. My feelings of vulnerability intensified for a moment as I wrapped my senses around this new elevation. My mind was clear as I gripped his length with my two hands. I cautiously began licking and teasing him with my tongue. I held it in my hands and licked up from the base all the way to the top. I paused at the bottom edge of the head and then gently placed my lips over the top to size it up.

I finally put it in my mouth. He liked that very much, so I decided to try a little more. I cupped it with the edges of my mouth and slowly lowered my lips down his shaft. I struggled to fit half of him into my mouth. His hands were resting on my shoulders, but as my motion became more rhythmic and intense he started rubbing gently but firmly on my neck, and then eventually my hair. I could tell from the pressure that he didn't want to make me gag, but at the same time he wanted his entire dick down my throat.

My lips went up and down, not able to take on the entire length, but able to give what I thought was a pretty good effort, good enough anyway to express my gratitude for the way he had gotten me so well on the massage table a few minutes before. I soon realized that he was making louder noises and moving his hips in a way that made it seem like he might explode. I felt like an absolute slut, trying to take as much of him in my mouth as I could each time, over and over, knowing that he couldn't handle it anymore.

He was getting close, and I could tell that he wanted to take me right then and there. He picked me up and placed me firmly on the massage table. I leaned back, but I fought to remain partially sitting up. He climbed on top of me and placed his massive dick on top of my pussy. It's length reached beyond my belly button. My eyes grew massive seeing just how deep I was about to take him. He then placed it at the entrance of my pussy and began to slowly insert it inside of me. He was very thick. It was difficult to take, even with how wet I was. I watched it disappear into me, inch by inch. It was a stunning visual to see his black length bury into my white pussy.

With the sharp contrast of our different skin colors being exaggerated by the shade of the hut, not to mention the scandalous beach location itself, we made for quite a dramatic scene behind those curtains. He was still teasing me with his dick, or testing me, I couldn't tell, as he only partially entered me on the first push. He pulled almost all the way back out and then went in again. It felt even tighter and harder to handle than the first time. I let out an involuntary breathless sigh as his full length went deep inside of me.

Despite his massive size, I couldn't believe how good he felt. He had only been back and forth inside of me twice and I was already feeling like I could be over the top again. Realizing that I could somewhat handle him, I tried to spread my legs open even wider and raise my hips up higher, to take on as much of him as he could possibly give. I leaned all the way back and wrapped my legs around him, letting him pound into me over and over and over again. He had me completely out of control and outside of my own head as I took his piston-like thrusts. I came again, hard, as he buried me into the table. My voice could not be stifled this second time, as I couldn't help but scream with each thrust of his cock beating into my swollen pussy.

Regathering myself somehow and actively trying to squelch any feelings of self-consciousness or shock over what had just happened, I realized something. I was the kind of girl who liked to be on top. I tried to sit up and catch my breath. I knew I needed to be straddling him. This situation was already out of control, so why not get it the way that I wanted?

He seemed to understand what I wanted, maybe by the look in my eyes or maybe by the way I began to shift my upper body and lean in closer to him. I climbed up to my feet, grabbed his cock, and sat down right on his dick, slowly taking his length again. He felt so good, but I was becoming so tender and overstimulated. This more intense angle of being on top was not going to be easy to sustain. I knew I maybe only had about 10 seconds in this position before he would have me coming again. He leaned back, pressing his cock against my already sensitive clit. I knew that he knew exactly what he was doing, shifting like that, as I saw a smile slowly creep across his lips. I barely smiled back as I stared into his mocking eyes and came down on him very slowly, testing the waters of what it would feel like to be on top and have him against my clit. He filled me up and stimulated me in a way that I couldn't even describe. It felt like he was touching my organs. It was way more than I could handle, but I managed to last for a few more moments before melting down again in another huge display.

He looked at me with a hard look in his eye and his smile disappeared. While he managed not to look mean or scary, it was definitely very intense for me to see. He was signaling to me very clearly that it was his turn now. He took me and flipped me around so that he had me from behind. I remembered when he had first pressed his dick against the center of my butt cheeks during the massage. I chuckled a little bit to myself, thinking of where we were now. I was on all fours, grinding against him in a way that was trying to tell him that he could take me any way he wanted me. He placed his dick up high at first, maybe seeing if I would flinch away from anal. He placed it right at the entrance of my anus. I knew I could barely handle him fucking my pussy, but I knew I couldn't even consider letting him fuck me in the ass. My mind still wandered there as I wondered what that would be like with someone of his size. I didn't flinch. He seemed surprised, but he didn't pursue it. Perhaps he was testing to see how much of a slut I was. He got his answer...