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.