It was the spring of 2004 and I had decided to visit Cuba for my vacation. As a single gay man I often travel alone and I am very interested in experiencing other cultures. I booked a flight with Aeroflot via Paris and ten nights in the Hotel Las Palmieras and off I went. Normally on my journeys I make contact online with some gay men before I travel so that I have some company during my stay, this time however I had some difficulty finding anyone who appealed to my particular tastes.

Undaunted I set off for Cuba, determined to take my chances and see what would come my way. I arrived to the sweltering heat of noon and booked into my Hotel. I explored the resort to find a fabulous Pool and Spa and a golden beach less than a minutes walk from the Hotel. Within the hour, I lay stretched out by the pool, working on my tan. Pretty soon I could feel myself beginning to burn and I looked around for someone to help oil my back. This is one of the problems of travelling alone, but it can start up some interesting conversations.

Lying on the sun bed to my right was an elderly lady with a pronounced New York accent and to my left was an older gentleman of about 70 who was quite good looking but a bit on the slim side for my taste. I decided that a slim man beats a loud woman so I asked him if he would mind applying some sunscreen. He agreed and we struck up a conversation. Chuck was from outside Dallas and was travelling alone as his wife had passed away the previous year. He was in Havana for two weeks already and had another two to go.

I asked him what the nightlife was like and what one did for pleasure after the Sun went down. Chuck said that what he really enjoyed was to play Bridge and that there was a good Bridge Club in the Hotel. He asked me if I played and would I like to join them that evening. I told him that while I knew the basic rules of the game, I really wasn’t a player and that I would only ruin someone the game. He invited me to join them in the Lounge after dinner and I could watch and learn or join in as I chose. I thanked him as said I would see what way the evening went.

After a lazy afternoon basking in the golden sunshine, I retired to my room for a shower and dressed for dinner. After a most splendid meal I decided to try the lounge and see what the clientele was like and if there might be some interesting prospects. As I entered the lounge, Chuck spotted me and waved for me to join him and his friends He introduced me to his friends and they were a nice bunch, mostly older couples, the stereotype Bridge player. After a drink and some small talk they paired off for a game and I retired to the bar to listen to the Piano player who was really quite good and cute to boot.

After about a half hour someone tapped on my shoulder and introduced himself as John, a friend of Chuck’s and asked if I would be willing to make up a four. I explained that I was a novice and if they didn’t mind the mistakes I was willing to give it a go. I went back to the Lounge and was introduced to the rest of the quadrille. One was Lily, John’s wife and the other was a friend of theirs called Tyler. Tyler was about 65 years old and stood about 5’8” tall and weighed in at about 220lbs. His face was well tanned and sported a salt and pepper goatee and he had a smile that would light up a room. He told me that he was in real estate and was from Huston. Tyler and I were to be partners against John and Lily, and that pleased no end as I got to sit across from him and could study him without being too obvious.

As the game progressed I noticed that Tyler was sporting a very impressive bulge in his crotch, promising a meaty treat if I could get near it, which distracted me quite a bit, with the result that I made quite a few elementary mistakes, which cost us the rubber. I apologised to Tyler and the others for ruining their game and thanked them for keeping me entertained. I offered to buy them a drink but John and Lily declined, saying that they had an early start in the morning. Tyler joined me in the Bar and we had a great chat, during which I discovered that Tyler’s wife had died three years previously and was travelling alone. Tyler asked me why I was travelling alone and I told him that I was gay. I asked him if I had shocked him but he said that it didn’t matter to him. We had a few more drinks and soon the Bar was closing and I asked Tyler if he would like to go downtown to see the nightlife. Tyler declined and advised me not to leave the resort alone at night, as Havana was a very dangerous town. I decided to take his advice and said goodnight when Tyler suggested a nightcap in his room as he wasn’t ready to retire and he didn’t want to drink alone, to which I readily agreed.

We took the elevator to the tenth floor and entered his room. It was huge, a Suite in fact, with a sitting room boasting a private bar. Tyler poured me another drink and we sat on the sofa and discussed the game and the basic mistakes I had made. I apologised again and deciding to try my luck told him that I couldn’t concentrate fully on the game because I was distracted, from looking at him. I told him that I really fancied him and that I wanted to kiss him all over. I placed my hand on his knee and began to stroke his thigh and from the growing bulge in his pants I knew he was enjoying it. I leaned over and kissed him gently on the lips and then on the ears and the back of his neck. He moaned with pleasure and I could see that his cock was bursting for release from the confines of his trousers. I unbuttoned his shirt to reveal a barrel chest coated in fine silver hair and two fully erect nipples. A deep vein of hair ran down between and continued over his basketball belly and disappeared into the waistband of his pants. I gently took one of his nipples into my mouth and began to suck and nibble on it. Tyler moaned and arched his back and I slowly lowered his zipper to release his magnificent cock. Tyler stopped me at this point and explained that he had never been with a man before and that, with the exception of messing around with other boys as a kid, he had never even thought about it.

I told him to relax and enjoy it and slowly peeled the foreskin to reveal a dark purple mushroom cock head. I gently took it in my mouth and slowly began to suck his knob, running my tongue round it and licking underneath the cap. Tyler moaned with pleasure and when I suggested retiring to the bedroom, he said nothing but quietly followed me. I slowly unbuckled his belt and dropped his pants and underwear to reveal a thick 5-inch cock surrounded by a halo of silver pubic hair. Underneath hung a pair of the most impressive balls I have ever seen. A stud Bull would have been proud of them. I eased him onto the bed and removed his shoes and clothes and quickly stripped. I knelt between Tyler’s legs and began to lick his inner thighs. Shudders of pleasure racked Tyler’s body and he gasped with newfound pleasure. Slowly I moved upwards towards those magnificent orbs. I licked and kissed them one by one and took each in turn into my mouth. Tyler was gasping and squirming with pleasure and his cock was oozing copious amounts of precum, which I hungrily lapped up. I ran my tongue around his cock head all the while lapping up his precum and watching as his cock twitched and pulsed with his every heartbeat. I slowly encircled his cock with my lips and plunged his cock deep into my throat. Tyler bucked and groaned with joy and his whole body shook with spasms as his cock gushed copious streams of cum deep into my throat, which I eagerly swallowed.

Tyler apologised for coming so quickly and explained that he had not had sex except for a jerk off in the last ten years. He told me that his wife had been seriously ill with multiple sclerosis for the last few years of her life and that he had not been with another woman during their marriage or since. I hugged him close and we just lay there holding each other until we drifted off to sleep.

Next morning I awoke still in the arms of this wonderful man. I could feel his rock hard cock nestling against my lower back so I gently adjusted until it nestled between my ass cheeks. Tyler was still asleep but his cock was not. It slowly slipped between my ass cheeks and soon had my furry glen slick with its precum. His cock throbbed in harmony with his heartbeat, like someone tapping on my asshole. I relaxed my sphincter and soon I could feel his cock head forcing its way into my inner sanctum. Soon it was buried deep within me and Tyler began to stroke in and out. From the change in his breathing I could tell that Tyler was now awake as he ploughed my ass with abandon, striking my prostrate with every thrust, sending wave after wave of pleasure surging through my body. He began to gasp and moan and I tensed my muscles as he shot his load deep inside me, filling up every corner. I held him inside me for as long as I could and when he eventually slipped out I turned and kissed him deeply.

Tyler bent down and tentatively licked my swollen cock and I assured him that he didn’t have to if he didn’t feel right about it. Tyler said he wanted to and took my knob in his mouth and began to suck. He tried to deep throat me as I had done for him the previous night but he began to gag so I told him to take it slowly. He continued to suck and lick me, all the while caressing my balls. Pretty soon I began to get the familiar feeling in my sack warning of an impending orgasm. I warned Tyler that I was about to come but he gamely kept on and took my load in his mouth as I gasped with pleasure. We retired to the bathroom and shared a shower. I soaped his back and ass, slowly caressing every inch of his beautiful body and then turned him round and repeated the treatment to his massive chest and shoulders, slowly moving down to his belly and finally his cock, which was rock hard again. I rinsed him off and knelt to take his cock in my mouth again. I sucked him slowly and he placed his hands on the back of my head as he slowly fucked my mouth. I caressed his massive balls and felt them tighten as I was treated to his second generous load of the morning. I stood and kissed him, letting him taste himself and he kissed me back, our tongues caressing and probing. He knelt and took me in his mouth and gently stroked me while he sucked. After a few minutes he withdrew and asked me if I wanted to fuck him. I told him that I would very much like to fuck him but since he was a virgin it would take time and patience to prepare his ass, so he took me in his mouth once more. By this stage he was getting used to my cock and he gradually began to take more and more of me into his mouth until his nose was buried in my pubic bush. I gently began to face fuck him and soon I was gasping and heaving as I shot my load deep in his throat. We rinsed off and dressed and had breakfast together.

Tyler invited me to go deep-sea fishing with him and his friends later that morning and I gladly accepted. In fact we spent the next two weeks together, during which he taught me all he knew about bridge while I taught him how to make love to a man. Eventually my Holiday came to an end and we said our sad goodbyes and I arrived back in Shannon tired but happy where I went to the Aer Lingus desk and enquired about flights to Houston Texas. After all my next vacation was only three months away.