School was over for winter break for a few weeks. I just finished all my grueling midterms and was looking forward to my winter vacation. I had booked a seven-day vacation in the sunny Caribbean.
I had just arrived in Jamaica yesterday - a long-needed and welcome diversion from the frigid existence of a Delaware January. When I left my home yesterday it was 15 degrees with a stiff wind and prediction of a blizzard. While on the plane I changed into a tank top and shorts, and arrived into 87-degree tropical air, looking at the azure blue of the water as we disembarked. I arrived late in the afternoon - just as the sun was starting to set in the western sky. I quickly checked into the guesthouse I was staying at in Kingston. After dinner I walked out to the deck of the pool for cocktails. The pool was beautiful with a diving board and a slide at the far end. I asked the bartender if the pool was 'suits optional.' He responded with a slight smile and said 'Only late at night...' I made a mental note to return later that night. At this point I could never have expected this to turn into one of the most incredible vacations I had ever had.
After walking the beach along Port Royal and listening to the seductive sound of the waves, I returned to my room. I changed into my Speedo and grabbed a towel and stepped out on my patio and headed to the pool. Even in the late night hours the air was still incredibly warm and humid, and the water of the pool glistened under the moonlit sky. I carefully checked out the pool area. All the lights were out in the rooms overlooking the pool and I had the entire area to myself. I slipped off my Speedo and felt the warm air across my body. I immediately felt the first stir of excitement in my body and especially in my groin. I gave my cock a couple of long strokes as I walked on the pool deck toward the diving board. I put my foot into the water to check the temperature; it was cool, but still warm enough to be inviting. I walked onto the diving board and slowly bounced at the edge as I looked into the water. I felt my cock rise to full erection as I gently moved up and down on the board. Then I dove in. The initial coolness of the water sent a shock wave through my body as I swam underwater the length of the pool. I surfaced at the shallow end then did a surface dive and dolphin kicked to the other end. I climbed out of the pool, my cock now fully erect and walked over to the slide. As I was climbing the ladder of the slide, I thought I saw someone standing nearby. I looked closer as I reached the top of the slide and decided it was the shadows being cast by the gently waving palm trees. I positioned myself on the slide and then let myself glide down on my back and back into the water. The feeling was incredible. I spiraled down to the bottom of the pool, then slowly surfaced, sending out a stream of bubbles on the way up.
When I surfaced I immediately noticed that I was no longer alone. Standing by the pool was the bartender from earlier tonight. The pool was not lit up at this time, so I didn't think he could tell that I was naked, but a part of me wanted him to know that not only was I naked, I was dreaming this man would join me in the pool.
'How is the pool this evening, sir?' He said, with the same charming grin he had displayed earlier that evening. 'It's incredible.' I said, treading water from the deep end, then swimming to the side of the pool to converse further. He bent down close to me when I reached him. 'I see you took my invitation from earlier,' he said with a laugh. 'What do you mean?' I asked in return. He walked over to the table where I left my towel, unfolded it and held up my Speedo, and smiled at me. I shrugged and said 'Well I hope it's ok, I didn't see anyone around.' He crouched down next to me again, and said, 'It's ok, I swim naked myself out here often. At this time of the night there is usually no one here.' My cock began to stir as I was drinking in the beauty of this man. He was dark skinned from being in the sun, not a native islander, no doubt, blond hair, and strikingly handsome. Not thin, but well built, broad-shouldered, with a husky build. We talked briefly, I told him about my home and the fact that it was wonderful to be here swimming whereas at home I would be freezing my ass off and shoveling snow. He laughed at this and said 'My name is Greg, I have lived here on the island most of my life.' He went on to tell me that he had never seen snow in his life, but would like to some time. He then told me that he has worked here at the guesthouse for a couple of years now, doing things like serving drinks and seeing to the needs of the guests. During his free time he and a friend run a charter boat service where they took people out for snorkeling and tours around the island. I listened to his conversation - charmed by his demure manner and his lilting accent. I kept floating in the pool, feeling my hard cock bobbing up and down in the water. Greg stood up and looked out at the ocean beyond us then up at the sky. I thought he was preparing to leave when I saw him turn and remove his shirt. He turned back to face me and said, 'The water looks very good tonight, may I join you?' Before I could answer him, he undid the clasp of his belt and slowly removed his pants, revealing his incredible body and one of the biggest cocks I have ever seen which was topped by a triangle trimmed blonde pubes. I swam out to the middle of the pool and treaded water as Greg walked to the edge of the pool then executed a graceful dive into the water, barely making a splash as he entered. He swam underwater and emerged directly in front of me.
'You are right,' he said as he surfaced, 'the water is very nice tonight.' We faced each other for what seemed an eternity, just looking into each other's eyes and smiling. I then felt a hand graze my thigh, then slowly moving up between my legs and finally cupping my ball sac in his hand, while his other hand guided mine towards his fast-stiffening cock. Without speaking I took his manhood in my hand and began a gentle massage. Greg returned the gesture to me, and slowly our lips came together in a kiss, then parted and our tongues danced together as we slipped below the surface of the water. An electric feeling shot through my entire body. I stiffened in anticipation of having a massive orgasm. We continued to deep kiss while locked in an underwater embrace. We both stroked each other's cocks until I felt Greg's body tighten. We broke our embrace and sent streams of white globs of cum up to the surface as we both shot loads of our juice simultaneously. With the last of air available to us we kissed again and slowly ascended to the surface.
When we broke the surface we again kissed, and Greg said. 'Welcome to the Jamaica. I hope your stay is long and wonderful.'
'With you as my host,' I responded, 'It couldn't be anything else.'
We climbed out of the pool and dried off. 'It is late, you must rest.' Greg said to me. 'It's all right, I am on vacation.' I said with a smile.
Greg smiled again. 'You need sleep. Tomorrow I will arrange a charter excursion with my friend for you. He will take you out to the other side of the island and show you around.' Then he winked at me and said, 'And will share with you an adventure in a beautiful cove.'
I looked with anticipation and tried to imagine what this adventure would be.
'You sleep now, I will arrange everything in the morning and will call on you at 8AM.'
He then offered me a parting kiss and said 'Remember, I will call on you at 8AM.'
I was dumbstruck. I just made love to this man in the pool. I was moved by his beauty and aroused by his prowess. I watched as he walked away into the night, and thought to myself that I may finally have discovered my ultimate paradise.
The ringing of the room phone woke me out of a sound sleep.
'Hello,' I mumbled groggily.
The voice on the other end was unusually cheerful. 'Good Morning my friend! This is Greg, I am waking you as I promised.' He said with a hearty laugh. 'Remember after our encounter last night? I promised you an adventure today,' he said again with a hearty laugh.
Suddenly the experience of last night came back to me. Our making love in the pool in the middle of the night. An incredible feeling of arousal cascaded over me again.
'Yes I remember it well, in fact I am still tingling from the memory of it.' Greg laughed. 'Indeed it was wonderful for me as well. Are you ready for the adventure I promised you?'
My cock began to stir with anticipation. 'Yes,' I said. 'I need to shower and dress and can meet you in the front room in about 20 minutes.' Greg laughed again. 'That will be fine my friend. Bring some sunscreen and a couple of towels and I will drive you to the dock where you will meet my friend Tony. He will be taking you out on his boat for a tour of the rest of the island.'
'It sounds great. Like I said I should be ready and in the front room in about 20 minutes.'
'I will bring the jeep around and will meet you, you will have a wonderful time my friend.' With that he hung up.
I quickly showered and dressed for the day. I put on my skimpiest Speedo, a pair of khaki shorts, a sport shirt and a pair of sneaks. Grabbing a small shoulder bag, I packed it with a couple of large beach towels and a bottle of sunscreen. I walked out to the front room wondering what may lay ahead of me for the day.
Greg greeted me in the front room. He was incredibly beautiful as I remembered, even more so in the light of day. His dark skin was offset by the pale yellow shirt and white slacks he was wearing. 'Well my friend, I see you are ready for your excursion. Come now, get in the jeep and I will drive you to the dock.'
We climbed in the jeep and talked some more on the trip to the dock. Greg told me of his struggles with being gay and living on the Island. 'This lifestyle is very much looked down upon by the natives here. I have to be very careful about encounters like the one we had last night.' He said in a low voice. 'I have shared that experience, the sexual encounters, with many guys who have come here, but must be careful. My older brother caught me once and beat me severely. He told my mother and she stopped speaking with me until I promised to go to church and pray that my soul would be healed. Hell, it is healed. God doesn't make mistakes as I see it. But that's not how fundamentalists see it.' I listened and felt very sad for him. The U.S. certainly sounded much more liberated than this tiny island; that is depending on where you lived. 'I hope that I didn't contribute to making a bad situation worse for you.' I said. Greg laughed and said, 'Don't worry, I am much more careful about this now. I just have to be sure that no one is around to see what I enjoy doing.' He said with a laugh.
We arrived at the dock at the far end of the beach. I jumped out and looked around. Several small boats were lined up. Some obviously private craft while others displayed signs advertising day trips and scuba/snorkeling excursions. Greg told me that Tony was at the far end of the dock, and would be expecting me. 'Enjoy your ride, my friend. I'll look forward to your telling me all about it tonight at the pool.' He laughed and drove off. I walked to the end of the dock and saw the sign advertising the excursions, but was taken aback by the man next to the sign. He was wearing a red tank top and the smallest white Speedo I have ever seen which showed off his immense manhood in a most revealing fashion. He was about 6 feet tall with darkly tanned skin and beautiful brown eyes. He had short-cropped hair and a completely hairless body from what I could see around the tank top. Long and muscular legs extended from his ripped, muscular torso, and his butt cheeks were as firm and round as ripe melons. In all - a stunning example of man. He turned and greeted me with a smile that made me weak in the knees.
'Tony?' I asked. 'Yes sir, I am Tony. 'Yes sir,' he said, 'My boat is ready to show you paradise.' Then his lips separated into a huge, white grin, which proved to have an incredible charm and allure.
I introduced myself to him. Then he asked me 'What is your pleasure today, sir?' I told him that Greg had recommended him to me and he laughed softly. 'Greg is a great friend. He told me about you and last night.'
Then he winked at me and smiled again. 'Well I am sure we will have a great time.' I said with a smile. 'I am hoping you can take around to some of the good snorkeling sites and a place to do some swimming and diving from the boat.'
Tony smiled back at me. 'I am most certain I can show you a good time.' With that he prepared to leave the dock as I climbed aboard the boat. The boat was a small cruiser. About 15 feet long. It had an area in the middle for the controls and the wheel. A sun deck was at the front of the boat and an area of benches at the rear. Tony pointed out a large cooler filled with a few bottles of the local beer and fruit for snacking. Tony started the engine and we slowly began to
pull away from the dock and into the bay.
When we were some distance from the dock I took off my shorts and tank top stripping down to my white Speedo. Tony caught me undressing and smiled. 'That's it, make yourself comfortable!' With that he removed the tank top he was wearing and I saw his massive, hairless chest. He took to the controls and I lay back on the deck enjoying the motion of the boat and the sounds of the waves.
After about 20 minutes we came to a stop in an area of the bay where there were other boats docked nearby. Tony let out the anchor and went to the stern where he lowered the swimming ladder and grate for diving. 'This spot is excellent for snorkeling.' He said with a smile. 'There are pods of bottle-nosed dolphins here that are quite tame and gentle so we can swim with them.' I admit I was a little nervous at first because I had seen purposes off the shore of Fenwick Island when I stayed there on vacations and they were large animals, but Tony assured me they were quite harmless.
I put on my fins and mask, adjusted my snorkel and walked to the edge of the boat. I turned and saw that Tony was putting on fins and he said, 'I will join you if you don't mind.' I immediately felt my cock stir in my tight Speedo. 'I would like that very much.' I said. 'You will be an excellent guide for me.'
We tumbled into the water simultaneously, surfaced, adjusted our masks and snorkels and dove under the surface. The water was incredibly clear, and I got very aroused watching Tony who was leading the way, glide through the water in long and graceful kicks of his flippers. He obviously was quite at home here. We swam up to a pod of dolphins near us, and I was surprised at how docile they were in spite of size. We swam with them and surfaced for air occasionally and at one point Tony moved a youngster close to me and motioned for me to pet it. He laughed heartily causing bubbles to escape from his mouthpiece when I petted it gingerly from arm's length.
After a short while the pod swam away towards another boat where the passengers were feeding them by throwing fish bait into the water. We surface and Tony stated that that was not a good idea because sometimes when they feed the dolphins that way it has been known to attract sharks into the area.
Now we were alone near the boat and Tony motioned for me to swim back to it boat with him. I readjusted my snorkel and mask and dove beneath the surface. Tony swam next to me and we slowly swam back towards the boat. At one point we stopped and began to tread water. Tony reached out and took my hands as we briefly floated together in asubmarine hold. I felt his left fin brush up the inside of my legs and up to my groin. I returned the gesture to him and began to feel my hard cock pushing up against my tight Speedo. I looked under the water and saw the bulge in his white Speedo beginning to enlarge. We surfaced for air and swam to the boat. Tony climbed out first and helped me
onto the deck. We took off our fins and masks and climbed back onto the boat. With a smile, Tony turned to me and said; 'Now I will show you paradise.'
He started the engine and we sailed off further out into the bay, near a small outcopping that was completely devoid of other boats. This looked to be a deep, clear lagoon with incredible many hued coral formations on the bottom which contrasted with the white sand of the beach. Again Tony brought the boat to a slow stop, and lowered the anchor. 'This is a perfect spot for free diving.' He said with a smile. 'Nearly 20 feet deep here and some beautiful fish and coral to see.' It was breathtaking I told him. 'Let's take a swim.' Tony said and with that he stepped out on to the deck. In one slow movement he had taken down his white Speedo and stood before me naked. He turned to me with a smile and dove into the water. I watched from the deck as his nude body glided under the surface in long, graceful movements. With his arms and legs spread he moved effortlessly through the water. I rubbed my cock through the lining of my Speedo as I watched him swim. He surfaced for air near the boat and then playfully squirted a mouthful of water at me. Then he laughed and dove under again. I quickly removed my Speedo and dove in from the rail of the boat. I saw him
underwater and swam directly toward him. My erect cock was hard pointing at the bottom as I swam towards him.
He swam to me and we immediately engaged in an underwater embrace. My lips meeting his, our mouths parting, and our tongues dancing together as we shared one breath between us. We surfaced briefly for air, and then I dove back down and took the tip of his manhood into my mouth. I slowly began to tease the head with my tongue and the sensation of the warm salt water. Tony ducked down under the surface and ran his hands over my head as I continued to swallow his rigid sex. I eventually managed to get the 9-inch shaft down my throat and began to move up and down on it while I floated beneath the surface. I felt the urge to breathe, but Tony continued to hold me there and I continued my cock worship. Just as I felt the last breath escaping from my lungs, Tony took hold of me under my armpits and pulled me to the surface. I breathed in deeply, feeling the dizziness I was experiencing slowly beginning to subside.
'Are you all right, my friend?' Tony asked. 'Was I all right? I was in heaven, I thought. 'I am fine, just stayed down there a little longer than I should have.' Tony laughed and said 'Well, let me make it better for you.' With that he took a deep breath and dove under the surface. He cupped my buttocks in his hands and took my throbbing shaft into his mouth. I breathed deeply and then sank under the surface to watch him do this underwater homage. The sensation was incredible and my orgasm was gathering inside me. Just before I felt the burst coming, he released my cock from his mouth and we both surfaced again.
We took in air and I pulled my body next to his to feel our rigid cocks together as we again kissed. Tony then gestured for me to follow him and together we surface dived to about 10 feet below the surface. As multi-colored fish surrounded us he took my hands and pulled me next to him. We swam together in sort of an underwater ballet, then we kissed deeply and Tony began to massage my cock as I massaged his. Again I felt the need for air, but I couldn't stop this moment from being reality. We both stroked and kissed and Tony shared his breath with me. I felt his body
tighten, and mine tightened as well. In one movement we both threw our heads back and sent a stream of bubbles ahead of us as we shot our loads into the water. Several white ropes of our cum surrounded us, as we began our ascent to the surface.
As we surfaced I was very light-headed from the intensity of our lovemaking and the lack of oxygen. Tony helped me onto the boat and laid me down on the deck. He got a can of spring water from the cooler and said 'You rest my friend and drink this. We will anchor here for a while and then take another swim before we go back, if you are feeling up to it.' He then smiled and said. 'You are a wonderful lover under the waves.'
I put my head back and closed my eyes. Thinking to myself the stories I would be sharing with Greg that night at the pool. What a vacation this was going to be, I thought. Then I closed my eyes and let sleep take over.