Gay Sail Holiday

My first time on an organised solo, gay sail holiday; I joined a large 65ft charter yacht berthed in a marina in Plymouth, for a two week holiday sailing to France and back via the Isles of Scilly. It was the first time that I had done this type of holiday, but I did have some offshore sailing experience.

On arrival in Plymouth I met the skipper of the yacht; he looked the Captain Birds Eye character, complete with white beard. He introduced me to his full time crew. A Sailing Master who looked like the old man of the sea, with a heavy Cornish accent, that he was very proud off, a Mate and a Cook, from his round shape must have enjoyed the food he prepared. We were to refer to them as Skipper, Master, Mate and Cook, a sailing tradition; so they claimed.

I was then introduced to my sailing companion's that had already arrived on board. I was also introduced to Jim, whom I had never met before, but was to share a small cabin with for the next two weeks. We were both about the same age and build, I was from the North he was a local from Devon. Jim showed me the cabin and where to store my gear; the cabin was small but comfortable. Given the confined space within the cabin, it was clear Jim and I were going to get to know each other, well, during the next two weeks. I had the top bunk, Jim the bottom bunk.

After lunch the Skipper outlined where we would be going, what we would all be doing on board during the next two weeks and gave us a safety briefing. There were sixteen guests, on board, all male, most were couples or knew each other as friends before this holiday. Essentially we were paired off to crew the yacht. Two on sails, two helming, two as deck hands, under the supervision of the Skipper, the Sailing Master or the Mate at any one time. Two were assigned as galley slaves under the supervision of the Cook. We would all take turns on each of these duties. We spent the afternoon getting to know how the yacht worked and where things were stowed. By late afternoon we seemed to get the grasp of what was expected of us.

We spent the evening getting to know each other over an excellent meal prepared by the Cook and his two slaves, with drinks to follow. We all seemed to get along well with each other, although this would be put to the test over the next few weeks. As we were to leave early next morning to catch the tide out the river Tamar; we all turned in early.

Due to the confines of the cabin Jim and I had a challenge to get ready for bed; we kept bumping and rubbing each other as we maneuvered to get undressed. In many ways it was fun and a bit erotic.

We were both finally down to short close fitting bikini type underwear. Do we stop there or go for the full display. I was starting to feel, well a bit over aroused and would show if we undressed further. I think Jim was thinking this too. As we were about to climb into our bunks we were hit with the wash from something either travelling too fast or large or both leaving the marina.

We both collided and ended up face to face, bodily pressing on each other, intimately; I could feel Jim was aroused, as was I by this time. Also; I could see it in Jim's eyes, like me, he was enjoying the moment. Jim then ran his finger down my arm, slowly and seductively, while nibbling my ear lobe, I mimicked his gesture. Both our hands reach each other's underwear in unison, slipping our fingers inside exploring each other's arousal. We both then slid each other's underwear off in unison. Both being fully aroused by this time rubbed each other intimately, we felt a response building.

As we embraced each other we both decided to go to the next stage, it wasn't long before we had positioned ourselves on Jim's bunk. The close confines of the bunks bulkheads, gave us good positioning. Jim engaged with me, slowly penetrating to start with, and then he started to ungulate slowly. As he started to cum his rhythm increased until he unloaded. We changed position and I started to engage with Jim, after what seemed a long time I unloaded too.

We disengaged and started spooning each other. The bunks were not that wide to share all night. Not sure what to do next. We went to our respective bunks but with our underwear on this time. Next morning we got dressed one at a time. Although I did feel Jim's wandering fingers from time to time, as he did mine.

Our holiday started proper the next day, as it was a very hot summer day we were all got dressed down to swimwear, tops and trainers.

Leaving the marina the Skipper took charge, before long Jim and I were on the sails as we both had done some sailing before. Took a while before we were both working together, initially we were almost literally getting tangled up with each other as we set the sails. Again as we bumped and rubbed against each other, we were both starting to enjoy the experience, again. Not as erotic as last night but comfortable with each other's close presence; as we set the sails and cleared away the sheets and lines. The Master was a perfectionist regarding the tiding of his sails and lines. All ship shape and Bristol fashion he kept quoting in his Cornish accent. He was one of those really likable guys, even if he was telling you for the third time to do it again.

There was a lot of body contact between us throughout our watch, which we both didn't seem to mind. But I think liked. By the end of our four hour stint we had got to know each other and became comfortable working together. We went down below to the large table to have lunch, was a bit crowded. Jim was sitting closely next to me; our legs were touching and rubbing as we sailed. Adding to what we had already experienced. I started to think maybe tonight we might just sleep naked.

After lunch, being off watch, we went topside and stripped off and enjoyed the sun together. We shared our backgrounds together; I worked in an office of a defence contractor, Jim in the Naval Dockyard. Later that evening we had a second four hour watch together, it was dark by now and we were alone. The others were having their evening meal below.

Jim shared with me that he was not gay when starting college. In his second year he ran into financial trouble, looked as though he would have to give up his studies and start working full time. He didn't want to do this as he was doing very well in his degree studies.

He didn't know what to do, when one of the students approached him saying he knew someone who was looking for male Escorts for visiting business men. He was assured all it was, was to be with them for companionship; nothing more.

He agreed and met with the person who was organising the meets, for a once over. He was told how much he would get, which was very inviting and would get him out of his financial hole. Anything undertaken on top was up to him and he could keep half for himself. But he was not obliged to undertake anything extra. It was up to him.

His first meet was at a big hotel on the Hoe with an American. He was very nice, well presented and polite. Enquiring as to what Jim was studying and why was he was doing Escort work. Jim felt guilty and told him. They had a nice meal, an unexpected extra. Was invited up to his suit for a drink, while he phoned his office in the States, they were on flip side time to the UK. Or, he could wait in the bar until he finished his call. Jim liked him and agreed to go and wait in his room while he made his call.

When the call was finished he came through from the bedroom. He directly asked Jim if he was gay, Jim said no, never did anything like that; why. He would be appreciative if he was and would show him what to do. He put some money on the table and sat on the couch beside Jim. Looking at the money; Jim said ok. They slowly stripped each other off, stood naked facing each other getting aroused together; and went into the bedroom together.

He showed Jim what he wanted and led him through his various preferences. He was very gentle with him showing how it should be done. Then Jim was invited to do the same to him, which he did. They then showered together, which was an experience too. Jim returned to his small one bed room but with enough money to pay his rent for the next few weeks.

He met up with the organiser, no names were ever exchanged, and who was very pleased with Jim as his client had called up, praising Jim. And, he would like to meet him for the next three nights. Jim became his regular Escort when he was over from the States which was once or twice a month. The organiser arranged other special meets for Jim. That's how he funded his degree and found out that he was gay because he liked it too.

I explained that I was not gay, except when I went to college, I met Ian and all that changed and I liked it too. Ian was now a policeman in New Zealand, other than odd letters we were not in contact with each other. I also told him my story of my college days when I explored my sexuality with Ian. I also said that I wondered how I would have reacted had I been offered Escort work. This was to be a defining confession for me.

As he was telling me his life story he placed his finger on my bare leg and rubbed it slowly up my leg, I was starting to get aroused by this, not annoyed, and he started to stroke me gently. I was enjoying it. It was not long before I was stroking him too, he seemed to be enjoying it too.

Our watch finished and we went below. In the cabin we sat next to each other on Jim's bunk waiting to see who would start. Jim pulled off his shorts, I did the same, and we both sat together each aroused. Then we joined in his bunk, we embraced and explored each other intimately. We reached the point where we knew we would have to take it to the next stage again or ease off. That was no longer an option as we both wanted intimacy.

We went to the next stage. Jim went first, positioned me to receive him and started to enter, uncomfortable to start with, but eased as we both relaxed. We were both a bit over excited this time and over quicker than it should have been. We reversed positions, bit less tense this time. Afterwards we lay together for a while then went to our respective bunks. Both of us slept naked that night. We were both awakened by the Skipper banging on the door telling us time to get up as we had the watch in 30 minutes. Both of us pulled on our shorts and went for a shower and tidied our bunks and cabin. Our first full day at sea and what a day.

We worked well together, the day passed quickly, we had joint mess duties that day, and fortunately we had a full time cook so nobody got food poisoning during our watch. We both looked forward for the night, as we had a mid-watch; the night was split in two. This meant we were twice as tired in the morning.

We arrived in France about ten in the morning so had almost a full day ashore that was fun too. We went to a nude beach along with some of the other guests. As it turned out most of the guests were gay or at least flexible. With time.

We had a fun two weeks in particular at the private beach parties. There was some swapping but limited to two couples, but we all had a fun holiday and were well tanned, all over, when we returned to Plymouth.

As I had a third weeks leave Jim invited me to stay with him for the week in his apartment and he could show me the area. I agreed. Not long after we arrived at his apartment his phone rang. He said ok I will come back to you on this shortly. He then asked me, you know how you said you always wondered what it would be like to do Escort work. Yes? Well would you like to make up a foursome tonight; it was his organiser on the phone. Don't know why but I agreed.

We went to the hotel on the Hoe, where Jim had his first client night. We were directed by reception to go straight up to their executive suit on the top floor. We entered, never saw a hotel room this big before, complete with bar.

There were four guys there; Jim said we were told there would only be two of you tonight. They apologised for the late unexpected change of plan but we would be compensated for it. There were two rooms in this suit if that helped. Jim agreed; I just followed his lead. We were led into one of the rooms, which were also adjoining. It was explained what they wanted which included dressing in a short nightie and we would have one room each.

We went to our respective rooms, got changed, not tried that before but must admit I liked dressing up. The first two came into my room with only towels on, sat on the bed beside me and started to fondle me. Hands were everywhere fondling and stroking me, they were so gentle, and it was nice and very arousing. Not what I expected. I felt some oil being applied and someone start to enter me, at the same time I felt the start of an oral massage. After a short while I was starting to cum, but holding it back, like Jim said to prolong the experience. My prostrate was starting to react as well. Never had both at once before. I couldn't hold back any more neither could they.

After a short recovery respite, they wanted to reverse roles. They started as before, clearly they had worked in unison before. Wasn't long before we all climaxed again. This time I was to give the oral massage, just as well as I don't think I could have cum for a third time. His partner gave him an anal massage. Another role reversal and we started again. By this time we were all getting exhausted.

We all put on our towels or straighten our short nighties and returned to the main room. For refreshments and relaxation. After about a half hour or so the wanted to start over; but swapping around this time. I returned to my bedroom being joined by the remaining two. This time they ripped off the nightie and frilly pants I was wearing, not violent, just in a fun way. We then repeated what happened before; they were a bit quicker this time in cuming, I think long term exhaustion was setting in. When we finished we all lay in the bed together, this time they were both massaging the inside of my leg. I could feel cum building but couldn't seem to hold it back. They liked that; I suppose I did too.

We all retired back into the main room, this time Jim and I were the only two standing there naked. They wanted us to give them a show while they watched, I didn't know what they wanted but Jim did, I followed his lead. We both gave each other anal then oral as they watched on with drinks in their hands. I should have felt humiliated at this but I didn't. I lost track of how many times I came that night or how many times I was entered.

They let us have a shower together; again they watched as we washed and cleaned each other, dried each other off and got dressed together. Jim was handed a thick envelope as we said our farewells. We headed back to Jim's flat, went to bed to sleep this time. The next morning Jim gave me half of what was in the envelope, it paid for the rest of our week touring Cornwall. What an experience never expected that when I went on a gay sailing holiday.

Jim and I still keep in touch and have done the odd twosome Escort together.