An Unusual Ending to a Holiday

This was my first time on a solo holiday; I joined a large 65ft charter yacht that was berthed in a marina in Plymouth, for a two week holiday sailing to France and back via the Isles of Scilly. This holiday had an unusual ending; I think.

On arrival in Plymouth I met the skipper of the yacht; he looked the typical 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 who was of the old school of sailing and became very excitable at times 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, I think; maybe not.

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, rather well, during the next two weeks. I had the top bunk, Jim the bottom bunk; no pun intended; honest.

After lunch the Skipper outlined where we would be going and what we would all be doing on board during the next two weeks, he also gave us the regulatory safety briefing. There were sixteen guests, on board, all male; most 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 all 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 at the same time; we kept bumping and rubbing each other as we maneuvered to get undressed. In many ways it was fun and a bit erotic too. Jim liked that me too.

We were both finally striped 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 fully 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 starting to nibble my ear lobe, I mimicked his gesture. Both our hands reach each other's underwear in unison, slipping our fingers inside exploring each other. We both then slid each other's underwear off in unison. Both being aroused by this time rubbed each other intimately; we felt a mutual 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, it was nice and comfortable. 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, nice long time, I unloaded too.

We disengaged and started to relax by spooning each other on the narrow bunk. 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; a nice start to the day.

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.

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. I liked it; Jim too. 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 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, I discreetly suggested this to Jim; he smiled back.

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 Devonport Naval Dockyard. We had a lot in common; both knew of projects and people working on them in connection with our ship building and refit work.

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 engineering 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 arranging the meets; for a chat and a once over to see if he was suitable; he was. He was then 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 Plymouth Hoe, where Francis Drake played his famous bowls game as the Spanish Amada approached. He was to meet with an American businessman; he was very nice, well presented and polite with a soft southern accent.

He enquired what Jim was studying and why was he was doing Escort work. Jim felt guilty and told him; no point in not. They had a nice meal together; an unexpected but welcome extra, particularly if you are a student struggling financially.

Afterwards he was invited up to his hotel suite 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 suite while he made his calls.

When the calls were finished he came through from the bedroom. Sat down next to Jim and asked him directly; if he was gay?

Jim said no, never did anything like that; why? He said he would be very appreciative if he was and he could show him what to do. He put some money on the on the couch beside Jim. Looking at the money; Jim said ok.

The American started to slowly unbuttoned Jim's shirt and removed it; he then removed his own shirt. Slowly they started to strip until they stood naked facing each other, they had both been getting aroused together as they stripped. They then went into the suite's bedroom together.

To start with they both lay on the bed together; he then started to caress Jim intimately. Jim's arousal was starting to develop and he could feel quickly his wetness starting to form; a nice pleasant experience.

Then; he could feel cum forming within him and slowly inch forward, his adrenalin started to take over as he became more excited, his breathing, quickened and started to become erratic; his first client was enjoying it; he was too. Although he knew what to expect next; it happened quicker than he thought it would and, was uncontrolled, as cum squirted all over his chest in two large bursts.

Now that he knew Jim was fully committed to having sex with him the client started to show Jim what he wanted to do next. He positioned Jim on his back, lifted his knees up, and opened his legs then positioning two pillows under his hips for steading and support. He then put oil on Jim and then himself, leaned forward and pressed on Jim as he tried to enter.

It was difficult and awkward at first as this was Jim's first time being entered in this way; then he could feel him slowly press through and enter him until he was fully in; this was the first time Jim had had his prostrate touched in this way. Jim was now starting to fully enjoy the shared experience, the client then started to ungulate back and forth at a gentle pace, and occasionally he could feel him re-touching his prostrate. This added to the thrill and he could feel pre cum start to run out onto him.

The client's rhythm was steady; not rushed but relaxed. Slowly the rhythm faltered and slowly became erratic, his breathing deepened; as did Jim's. They were both starting to ungulate in harmony as they built up to a climax, the client suddenly held back as he unloaded inside Jim; Jim could feel the enjoyment as it built up inside him. The client slowly withdrew and he could feel it drain out. It was his first time but enjoyed it.

They both then lay together relaxing, the client said thanks I hope you enjoyed that as much as I did. Jim said 'yes I did'. Jim was then invited to do the same to him, which he did with a bit of coaching and encouragement. Jim prolonged the experience for the both of them as long as he could; then unloaded. The client said 'yes' that was good, they both then lay back enjoying the moment and recovering.

Afterwards they showered together, which was an erotic 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 the next day, for confidentiality no names were ever exchanged, who was very pleased with Jim, as his client had called up praising Jim for his companionship the previous night. And; he would like to meet him for the next three nights, could he arrange it. Jim accepted.

Jim had his first regular Escort assignment, when he was over from the States which was once or twice a month. The organiser arranged other special meets for Jim too. That's how he funded his degree and found out that he was gay; because he liked to be.

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 and some friends.

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 and down my leg, I was starting to get aroused by this, not annoyed, and he then started to stroke me gently. I was really 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 sexual excitement.

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 by this time and it was 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 and each night afterwards.

We were both awakened the next morning 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 to 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 two days later about ten in the morning, so we had almost a full day ashore that was fun too. We went to a naturalist beach along with some of the other guests. As it turned out most of the guests on board were gay or at least, inclined to explore options. With time.

We had a fun two weeks in particular at the private beach parties. There was some swapping taking place but was limited to a few couples, we all had a fun holiday and were well tanned, all over with no tan lines; 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; I was quite excited about the prospect and had Jim to show me the ropes; so to speak.

We went to the same hotel on the Hoe, where Jim had his first client night. We were directed by reception to go straight up to their executive suite on the top floor. We entered; never saw a hotel room this big before; it was complete with bedrooms, lounge area, a very private veranda and 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; if we were still interested. There were two rooms in this suite 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 us dressing up in a short nightie; and each of us would have two clients together and would have one room each.

We went to our respective rooms, got changed, not tried that before but must admit I liked dressing up, no makeup or wigs just clothes; which were rather sexy. The first two came into my room with only their towels on, sat on the bed beside me and started to fondle me together. Hands were everywhere fondling and stroking me, they were so gentle, and it was nice and very arousing and a wee bit messy too. Not what I expected; I didn't really know what to expect.

As I stood up I felt some oil being applied and someone start to enter me, at the same time I felt the start of an oral massage; never experienced both at the same time before; it was exhausting but fun. After a short while I could feel my cum starting to build, I tried to hold it back, like Jim said to prolong the experience. My prostrate was starting to react as well. I couldn't hold back any more neither could they; we all seemed to explode cum together.

After a short recovery respite break, they wanted to reverse roles. They started as before, clearly they had worked in unison before. Wasn't long before we all climaxed again. The next time I was to give the oral massage, just as well as I don't think I could have cum for a third let alone a fourth 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 they wanted to start over; but swapping around this time. I returned to my bedroom being joined by the remaining two clients. This time they ripped off the nightie and frilly pants that I was now to wear, not violent; just in a fun way; it was fun too.

We then repeated what happened before; they were a bit quicker this time in cuming, I think long term exhaustion was setting in; it was with me. When we finished we all lay in the bed together, this time they were both massaging the inside of my leg. I could feel my cum building again but couldn't seem to hold it back no matter how hard I tried. They liked that; I suppose I did too.

We all retired back into the lounge area, this time Jim and I were the only two standing there naked; they all had their towels back on. They wanted us to give them a show while they watched us, 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 think they took some photographs of us on their phones. I should have felt humiliated at this but I didn't. I lost track of how many times I had cum that night or how many times I was entered.

They let us have a shower together; again they watched and photographed us 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 together but to sleep this time.

The next morning Jim gave me half of what was in the envelope, it paid for about half of our sailing holiday. What an experience never expected that when I went on a sailing holiday.

Later on in the morning the Organiser phoned Jim to say the clients were very pleased with us and said next time they were over could we entertain them again. What can you say we enjoyed it too. The rest of our week we toured Cornwall as planned.

On the Thursday afternoon Jim's phone rang; it was the organiser. Would we both be available to meet a client and his friends on his yacht in Penzance marina for an afternoon visit; Jim asked me I said yes; why not. He then explained what they were looking for; sounded like what happened on the Hoe a few days ago. It was about an hour's drive from where we were.

We found their yacht, it was very big; much bigger that the 65 foot yacht that we had come off. No crew they were crewing it themselves and were about to head over to France tomorrow. But, they wanted some discreet same sex fun with strangers tonight. They wanted it on a one to one basis and had organised two cabins with double beds where we were to entertain them.