Up until now, I have always been a heterosexual male. Recently, though I have been rethinking my sexuality. The last few relationships with girls have been less than exciting and have ended badly. I am not saying that I am giving up entirely on girls, but I am curious about how I would feel about having sex with another man.
So, to explore my newfound curiosity I decided to go on a vacation to an Island resort in Jamaica by myself. However, before going on this vacation, I needed to spend a few extra hours in the gym to whip my body in shape. After all if I was going to attract any attention, I needed to be as fit and trim as I could possible be.
After a month of extra hard workouts, I decided to book my trip. My travel agent was a nice guy, so when I told him that I wanted to go to a secluded beach resort in Jamaica, he said that he had the perfect place. Once the trip was all set, I went shopping for a new bathing suit since all of mine were sort of old and outdated.
I went to this little shop downtown and started looking around at all of the suits. There were hundreds of those surfer-type suits that hang down to your knees and are covered with every color in the rainbow. I didn’t think that style was going to get the reaction that I was looking for, so I ventured into another section that carried men’s thong bathing suits. I was just about to buy a black one, when I spotted a suit rack with what looked like a bunch of strings hanging from it. I thought “what the hell!” if I was going to go down that road, I might as well go all the way. I picked out a bright pink string bikini that was comprised of a piece of cloth no larger than my hand and some strings attached that tied together to hold it in place.
I was almost ready for my trip. On occasion when I have been on a beach before, I had noticed some guys with small rings hanging from their nipples. It really intrigued me and since I have always had naturally larger than normal nipples, I thought that some day I might want to have my nipples pierced. Well, today was that day. I was just in a mood to do a whole bunch of things differently than I have ever done before. Right near the little shop where I just bought my new “bathing suit” was another little shop advertising tattoos and piercing on its front window. So I walked right into the shop.
There was a rough-looking guy at the front desk with tattoos all over his arms and neck that asked if he could help me. I told him that I was considering having my nipples pierced. He said that he had an opening right now if I was interested. I said absolutely and escorted me into a back room. After picking out some jewelry to adorn my nipples, he asked me to remove my shirt and sit back in what looked like a dentist’s chair.
I know that I was in the mood to try new things, but when the moment had arrived I was a little nervous. He marked the sides of both of my nipples with a black marker after cleaning the area to be pierced with an alcohol swab. He then reached over to his tray and grabbed a long needle. He placed the tip of the needle over one of the black markings on my right nipple and told me to brace myself. With one quick motion he pushed the needle right through my nipple. Boy, that hurt like a bitch. Then without wasting anytime, he picked up the 10 gauge nipple ring that I had chosen and inserted it into the hole in my nipple while pulling the needle all the way through.
Once the ring was in my nipple, the intense pain changed to a throbbing sensation. I looked down at my now red and swollen nipple that now had a silver ring hanging from it. Then with very little time to recover, my piecer repeated the same procedure on my left nipple. When he was all finished, he told me to put my shirt on and gave me instructions on after care of my new piercing in order to avoid infection. I paid him and headed home.
Once home I showered and stood in front of my mirror to check out my new additions. I liked the way that they looked, but the hair on my chest seemed to hide them somewhat. A lot of the guys at the gym where I work out shave their body hair either for competitions or to make checking the progress of their muscle building easier to see. So, I decided to add one more new item to my list of trying new things. I went back into the shower and lathered up my whole body and began to shave off all of my body hair. It took a long time, but when I was done except for the hair on my head and eyebrows, I was hairless.
Now when I had finished and looked into my mirror, my nipple rings stood out as well as my now completely nude dick and balls. I took my new bikini out of the bag and tried it on. The small patch of pink fabric barely covered my package and the strings holding it in place went up the crack of my butt and tied on the sides just above my hips. Now when I looked into the mirror, I think that I had finally achieved the look that I was looking for. Between my workouts leaning out my body, the removal of my body hair, my nipple piercing and my new bright pink string bikini, I was now ready to head out on my vacation at the beach.
Two days later my scheduled flight for my vacation at the Jamaican beach resort took off on time. I had packed very little, since I anticipated being on the beach for most of my vacation. I only needed a few light clothes for dinners at night and naturally my toiletries. When my plane arrived at the airport, a shuttle bus from the resort was waiting for me. I was taken to a remote part of the island to a very rustic group of buildings called “Jamaican Get-a-Way”. The drive helped me with my bag and directed me to the main building to check in. Once I had checked in, another native Jamaican led me to a separate bungalow, which was to be my home for the next week. He told me when dinner was at the main house and which direction to the beach. I gave him a tip and off he went.
This was another first in accommodations for me. Usually when I went on a vacation, it was a plush resort with all of the amenities. This bungalow was by itself in location concealed by the island foliage with a small table & chairs and a very large 4-poster bed. There was an outhouse next to the bungalow and an outside shower. The accommodations were a little bit of a surprise to me, but also kind of exciting. I guess that my travel agent knew that I was looking for a new experience.
Since it was just about mid-day, I decided to take a quick shower and head off to the beach. I took off my clothes, grabbed a towel and walked out to the shower. There was no hot and cold water, but since we were in the heat of the summer the water was warm enough. It was a really refreshing shower and even more so since I was completely naked showering outside. As I said, my bungalow was secluded and I was sure that no one could see me showering, but I had the strangest feeling that someone was watching.
When I finished drying off from my shower, I put on my new string bikini, put some baggy shorts on over it, grabbed a large beach towel with my tanning oil and headed for the beach. After a short walk, I arrived at the beach on what was an absolutely beautiful bay on the ocean. There weren’t too many people there as yet, so I found a fairly private spot and laid my towel down on the sand.
As I was straightening my towel and getting ready to sit down, a Jamaican native came up behind me. “Can I get you anything to drink sir? We are famous for our rum drinks!”
I was startled at first, but agreed to drink any rum drink that he chose. He surprised me, because I didn’t think that kind of service came with this resort and I didn’t see where he came from. I returned to preparing my towel for my tanning afternoon. Once it was ready, I sat down and removed my tanning oil from my beach bag. I removed my shorts and shirt. Now for the first time my new nipple piercing and hairless body were on display in public along with my very tiny pink string bikini. I applied my tanning oil to my chest, stomach, arms and legs.
When I had finished, I just sat there for a few minutes looking around the beach. I guess that I hadn’t noticed it before, but there were very few women. The beach crowd was mostly men in either thong bathing suits or string bikinis like mine. Oh, well, I wanted a change of pace and this certainly fit the bill.
After lying in the hot sun for a while, my Jamaican friend returned with my drink. He actually returned with 2 drinks. He explained that it was always “happy hour” in this Jamaican resort. When I asked him how much, he just said that it was part of the package deal that they offered. I took a sip of one of the drinks and it was delicious. He told me to make sure that I didn’t waste a drop and I assured him that would not be a problem. He then left and I returned to my tanning.
I must have dosed off for a few minutes, because when I awoke another very large Jamaican native was standing over me. He was built like a body builder and was wearing only a very tight fitting thong bikini. His dark flesh glistened in the sunlight with beads of sweat running down over his muscular body.
“You need to be careful about getting sunburned in this hot Jamaican sun, sir! Roll over on your stomach, and I will apply more tanning oil on you.” He was such an imposing figure and said it so forcefully that I just did as I was told. By now I had already finished both of my Jamaican rum drinks and was feeling no pain. I was a little embarrassed about the almost complete exposure of my body in my tiny bikini, but I guess that the alcohol in the drinks removed some of my inhibitions. When I had made myself comfortable, this very large Jamaican grabbed my tanning oil and straddled me. He poured some oil onto my back and shoulders and began to rub it in.
“You are very tense and have many knots in the muscles in your back and shoulders. I will take care of that for you sir.”
His large, strong hands began to massage my upper back and shoulders. I have had massages before, but it has always been from a female massage therapist. This was the first time that a man had touched me like this. As he worked on my upper back he rested his butt on my almost completely bare behind. His rocking back and forth was getting me excited. When he was finished with my upper back and shoulders he got up on his knees and moved down to “apply tanning oil” to my feet and legs.
My big Jamaican “therapist” worked the oil into my calves then lifting my legs from my knee to massage my feet. It was truly one of the most erotic feelings that I have ever had. When he was finished with my calves and feet, he moved up to do my hamstring muscles on my upper legs. He moved my legs apart with his strong hands to give him better access to my inner thighs.
“You have a nice new “bathing suit” sir, but I am afraid that this dark tanning oil will ruin its beautiful bright pink color.”
After saying that, he grabbed both of the ends on either side of my string bikini and untied them. I was again startled by this move, but then decided that the tiny strings weren’t covering much anyway. With the strings on my bikini now untied, he put one of his large hands on my stomach and lifted me just enough to remove my bikini completely.
“You won’t be needing this right now sir, so I will keep it safe and clean for you.”
Now I was completely naked on a public beach in a remote location on a tropical Jamaican island beach. My very large Jamaican “friend” then poured more tanning oil directly on my butt and started massaging my cheeks. He once again moved my legs further apart allowing him better access to my upper inner thighs and between my butt cheeks. His strong hands were working over all of the muscles in my lower back, upper thighs and my ass. I have to admit that it felt just great.
He stopped for a minute and stood up, I assumed to stretch for a minute before continuing with his massage. When he kneeled back down, I felt something banging against my legs while he massage my butt. What I didn’t know was that he had removed his thong and it was his very large dick that was banging against my legs. We were both completely naked. It must have been quite a contrast with my almost completely white body being worked over by this very dark skinned large Jamaican.
“You have a very fit body sir and a wonderful ass. My hands are having a great time making you relax all of the muscles in your body on your vacation.”
He again poured more of the tanning oil on my butt letting it ooze down between the crack of my ass over my pink butt hole and down onto my balls. He was now moving his hands between the cheeks of my ass with his fingers grazing over my virgin hole. Then without any warning, he inserted one of his long fingers into my hole. My body jerked, but he held me down with his other hand placed firmly in the small of my back.
“What are you doing?” I said.
“Relax sir, this is all part of the service that we provide at this Jamaican resort. We know what you want and we are here to please.”
I don’t know whether it was that he was so large and strong or whether it was the affects of the Jamaican rum that I had consumed, but I was unable to resist anything that he wanted to do to me. We now had an audience of other men on the beach watching the action. He continued to invade my most private hole with his finger moving it in and out. He then inserted a second finger into my hole.
“I have to prepare you for a proper fucking sir. I can see that you are a virgin and I want to make sure that you are ready to receive my Jamaican friend.”
As he was working both of his fingers into my hole, he now placed his other hand under my stomach and pulled me up into a kneeling position. I must have liked the way I was being treated, because my own dick was now as hard as it has ever been. He moved his hand up to my nipples and started to pull and twist my nipple rings. My nipples were hard and sticking out from my chest. I knew that having my nipples pierced was a good idea.
“You are now ready to become my little bitch, sir.”
After saying that he removed his fingers from my hole, applied some of my tanning oil to his monstrous dick and pushed it between by butt cheeks up against my virgin hole. He grabbed me firmly by my hips with one of his strong hands and with the other hand guided the large mushroom head of his dick into my butt hole. It was spreading my anal ring until it almost felt like it was going to tear. Then it suddenly popped right into my hole and my anal muscles contracted around it holding it in.
I had never before even had an anal examination let alone have something as large as this up my butt. He then grabbed my firmly by my hips with both of his big hands and started to slowly work his large tool deeper into my hole. He pushed forward as far as he could go and then pull it out of me until just the large head of his dick was still in me. The pain was something that I have never felt before, but it was exciting at the same time. He kept moving in and out of me until I felt the course pelvic hairs up against the cheeks of my ass. He finally had been able to insert the entire length of his considerable large fuck stick into me.
Our audience of men watching me get penetrated by this very large Jamaican was now encouraging him to fuck me hard. He responded to the cheering section by pounding his dick in and out of my once virgin asshole. When he shoved forward he would ram his pelvis into my butt cheeks making a large slapping sound. I was being treated like a farm animal and I loved it. Between the heat of the Jamaican day and the fucking that I was getting, my body was covered in sweat and oil. His meat was sliding in and out of me at an ever-increasing pace.
Then when I thought that I couldn’t feel any more full with his large dick all the way up my ass, it seemed like it was growing larger inside of me. He then rammed it all the way into me one more time and held me tight against him as his body tensed. His balls then started to pump his cum deep into me. I could feel the warm cum deep in my bowels, and I just loved it. When he had finished pumping me full with his cum, he withdrew his now semi-hard monster from my now used and abused butt hole. Some of his cum started to ooze from me, officially making me a bottom in the gay community.
“I hope that you enjoyed your massage sir. I know that I did. We have you for a week and your fun has just begun.”
Our viewing audience had disbursed and my Jamaican therapist had left, but I knew that this would be a vacation to remember. I couldn’t wait to see what new experience would be next.