John's Story

Dionne was true to her word and booked a 2 day trip the following week, persuading her husband without much difficulty that she should sail with me alone. We enjoyed the sailing and fucked in every position possible on every part of the boat and I even broke my rule about leaving the boat to fuck her from behind whilst she hung onto the ladder that enabled you to get back on board from the sea (I justified this by assuring myself that we were holding onto the boat throughout). When we got back to base Dionne handed me another envelope, packed with even more cash than before, telling me that she and her husband were returning to The States in 2 days time so she would not be able to see me again. Whilst I was disappointed as I had enjoyed the sex and the cash bonuses, I was also a bit relieved.

There followed a few uneventful day trips with normal tips from grateful clients, I was totting up my bonuses, realising that I had enough to live for at least my first year at university but for some reason was feeling a bit depressed.

"Permission to come aboard?" I heard as a familiar smiling face appeared at the hatch.

"Simon!" I cried, "I wasn't expecting to see you."

"Last minute decision," he said, "Dad suggested that I come out and see how you are doing, we are getting a lot of really positive feedback about you!"

"That's nice to hear," I said.

"In particular, an American lady, Dionne Kerry was extremely fulsome in her praise for you."

"Oh, that is kind of her."

"Anyway, we have loads to catch up on, let me stow my bag and we can have a few beers."

"Do you want to head out for a bit?" I asked.

"Why not, it will be good to enjoy the sea."

I prepared the boat whilst Simon sorted out his stuff. We set sail and headed for my favourite bay as I knew that it had good anchorage and was nice and quiet.

We dropped anchor and both changed into swimming gear, me in swim shorts, Simon in Speedos.

"We can both swim as there are no clients and the boat is well anchored," he said so we both dived over the side to enjoy the water.

When we got back on board Simon grabbed a couple of beer bottles and we settled into the cockpit, soaking up the sun.

"There is something I need to tell you," said Simon, "and I am just going to come out with it. I'm gay."

I snorted, "no shit Sherlock!"

"You know?"

"I have always assumed it, I don't know why."

"Fuck, I have been so worried about telling you in case you were disgusted and didn't want to be my friend anymore."

"Simon, you are my best friend, you could never disgust me. If you are gay that is not a problem to me."

"Thank you, you don't know what that means to me," he said giving me a hug.

We sat drinking our beer and after a while Simon said to me "you seem a bit down mate, what's the problem."

I hesitated to say anything, so he added "I have shared my secret with you, so come on, tell me what is wrong."

So I told him what I had done with Dionne, leaving nothing out.

"No wonder her feedback was so good" he laughed, "so what is the problem?"

"I feel that I acted like a prostitute," I said, "she is only the second person that I have had sex with."

"The first being my Mum presumably?" He said.

My jaw nearly hit the deck, "How did you find out?" I asked him.

"Semen puddle on the lounger that time I came home to find you sunbathing with Mum."

"Oh shit, I am so sorry."

"What for, Mum clearly enjoyed it and I assume that you did as well?"

"Well yes, but I shouldn't have done it."

"It doesn't matter to me John, honestly."

There was a long pause, "So why are you feeling down, you have earned a lot of money and had loads of sex," he said

"I suppose it is because all of my sexual activity has been with older women, I still can't face asking out someone of my own age, and, as I said, I feel kind of dirty."

"So, if you could have a sexual relationship with somebody of our age, you would feel better?"

"Yes, I think that I would," I said.

Again, there was a long pause and then Simon leant towards me and kissed me softly on the lips.

"Whoa!" I said, "Where did that come from?"

"Just thought that I would plant an idea in your mind" he said.

I was stunned, I had always assumed that Simon was gay but never thought that he would find me attractive or that I might even consider him in a sexual way. The trouble was, my cock was staring to stir, leaving me feeling confused.

"I need another swim," I said and quickly dived into the water before he could see my growing bulge.

I swam about for a couple of minutes before returning to the boat. As I climbed the ladder, Simon was at the top and as I came level with his crotch he said. "I am sorry if I made you uncomfortable."

As I stepped into the cockpit I said, "It's fine, you just took me by surprise."

I suddenly realised that what I wanted was stood in front of me, my best friend. I hesitated and then leant in to kiss him softly on the mouth. He looked into my eyes, barely believing what was happening; he took hold of my head and kissed me deeply, probing my mouth with his tongue.

"Oh God that is good, you have no idea how long I have wanted to do that with you." Simon said.

I kissed him again and felt his hand brushing my cock through my shorts, "that feels nice" I said as I returned the favour and felt the outline of his penis and then pulling down his Speedos to reveal quite a small cock, only about 5" long but with a very pronounced glans at the end. Simon undid the string at the front of my shorts and plunged his hand inside and grasped my 8" erection. "Fuck that is enormous" he said as my shorts descended to the deck. We both kicked off our garments and stood gently stroking each others cocks whilst our mouths locked together again.

"Make me cum," he said so I started really wanking his cock, delighting in the feel of his hardness in my hand. "Oh shit!" he said as a couple of ropes of semen shot out of him and splattered over my torso and hand. I lifted the cum covered hand to my mouth and tasted it.

"Your turn," he said and knelt in front of me to start wanking me, his hand pumping up and down my length, swirling the pre-cum that I was leaking to lubricate his actions.

"I'm cumming" I said and released a huge amount of semen that splattered over his face, I pulled him up and licked it all of him. "I want to suck your cock," I told him "and I want to swallow your cum." He was hard again already so I knelt in front of him and took his entire cock into my mouth, marvelling at the feel of it in my mouth, the bulbous head feeling like a lollipop as it moved in and out of me, leaking salty pre-cum which I swallowed hungrily. Because his cock was relatively small I could take his entire length in my mouth with my nose buried in his pubic hair, inhaling his scent. I cradled his balls and then slipped a finger into his crack, seeking his anus to stimulate him further. As I penetrated his bum he grunted and unloaded a huge orgasm which I managed to keep in my mouth and swallowed it all down.

"Why don't we go into the cabin?" suggested Simon.

"Good idea" I said and we headed below decks.

"It's a good job the skippers bunk is a double on the boat" said Simon.

"Very lucky" I agreed as we collapsed onto it, holding each other in an embrace.

"Would you do something for me? Asked Simon.

"Of course, what do you want," I asked.

"I am a virgin," he said, "will you please fuck me?"

"I would love to take your virginity," I said, "Provided that you do the same to my bum as I am an anal virgin"

"I would be honoured to take your bum cherry" he said as he laid face down on the double bunk, legs apart.

"Have we got anything to use as a lubricant?" asked Simon.

"Olive oil should do the trick," chuckling, "it's extra virgin!"

"I think that you will need to use quite a bit to get that monster of yours up my arse."

I went over to the small galley and found the oil, as I returned to the bunk he raised his bum a bit and I leant in to have a closer look. I was so intoxicated and stuck my tongue out to tease his anus, receiving a loud groan of appreciation for my efforts. I poured some of the oil down his crack and massaged it into his anus, whilst coating my hard cock with even more oil. I knelt between his legs and pressed the head of my cock against his bum and pushed gently but steadily, his sphincter relaxing and gradually allowing me access.

"Oh fuck that is big!" He shouted, "take it easy."

I pulled back a bit to allow him to get used to my cock, applied some more oil and pushed back until he had my entire 8" in his back-side, my pubic hair brushing against his bum cheeks.

"OK?" I asked.

"Oh yes, yes, yes," he said, "now fuck me slowly."

I started to thrust in and out of him feeling even harder if that was possible.

"OK, fuck me harder," he said so I started to pick up the pace until I was pounding away at his bum. I felt the familiar feeling starting to build in my balls.

"I'm cumming, do you want me to pull out?" I asked

"No. I want to feel you shoot your load in me," he replied

"Oh fucking hell!" I shouted as my orgasm hit and I shot about 3 or 4 ropes of cum into his bowels.

My cock started to soften and slipped out of him, leaving a trail of semen on him.

"That was the biggest orgasm that I have ever had," I said

"It felt like it," he said, "I think that I will be leaking cum for days!"

We both laughed and cuddled up with one another. I then completely surprised myself by saying, "I love you Simon."

"I have always loved you," he replied, "from the moment that we met, I knew that you were the one."

We were both knackered after so much passion and in no time, we were both asleep in each others arms.

I awoke the next morning in an empty bunk, Simon was in the galley making a cup of tea.

"That's a nice view to wake up to," I said

"I am glad that you approve," he said bending over to get milk from the fridge and giving me a delightful view of his anus, balls and cock.

He got back into the bunk and started fondling my cock to full erection. I kissed him and said "I am not going to fuck you this morning."

"Why not?" he asked, obviously perplexed.

"Because I am going to make love to you instead, " I told him as I climbed on top of him. He pulled his knees back tilting his pelvis so that I would be able to penetrate him whilst facing each other. I applied the oil again and slid into him. I held him, my cock fully embedded in him and we kissed passionately as I started to thrust in and out of him, his erection pressing into my stomach. "Don't you cum," I said to him, "you need to do this to me afterwards."

"I am looking forward to it," he said.

I soon felt the familiar feeling of an orgasm building and in no time I spurted a rope of cum into him. I rolled off and washed my cock clean as I did not want to mark the sheets.

"I want to be fucked," I told him, "What's best, front or back?"

"On your front will be easiest for the first time, I think," he said so I rolled onto my stomach, parted my bum cheeks and lifted my bum slightly. I felt him kneel between my legs and then felt his tongue teasing my anus.

"It's a good job you bought a big bottle of oil," he said, "we are going to need to re-stock!"

I felt the warm oil trickle down my bum crack as Simon inserted first 1 then 2 fingers into my bum, finger fucking me to get used to the invasion. He withdrew them and then I felt the wonderful sensation of his oily cock pressing against my sphincter. "Just relax," he said. I did so and he pressed on opening me up and then once the head was in, the rest of his cock, being much narrower slid in easily. I could feel his pubes against my cheeks and he started to thrust into me.

"Oh fuck, that feels amazing," I told him as he built up his pace.

He carried on fucking me for several minutes, I felt his cock start to swell further and then knew that he was close. "Cum in me, fill me up," I told him.

He grunted and I felt his cock twitch and his hot semen shooting into me. This was too much and my own cock exploded as I had a first orgasm with nobody touching my cock, splattering the sheets, thinking, shit is there anything left in there?

Once we got out of bed, we got the boat ready for our return trip, Simon needed to get back to the UK and I had a few more weeks of work to go before returning myself. As we sailed back I said to him "I am not sure about going to Uni now, I want to be with you."

"Well Dad has always said that he has a job for you working with us on running the business whenever you want it," he replied.

"Not a conversation with my Dad that I would look forward to," I told him, "he is set on me going."

"Well, it's your life at the end of the day and do you need a degree?"

"Not if I come and work with you. Let me think about it."

"No pressure, you have a few weeks before the end of the season."

"Thanks, I really appreciate that," I said, giving him a kiss.

"Stop that or you will be fucking me whilst under sail!" He laughed.

"Tempting idea," I replied but concentrated on handling the boat instead of Simon.

At the end of September, I returned to the UK and went straight to Southampton to see Simon and his Dad, I told them that I would love to come and work for them if the offer was still open. They were both delighted and it was agreed that I would start straight away, well as soon as I had been home to tell my parents about my decision.

Simon said, "No need to look for somewhere to live, I have just got a flat near the marina, plenty of room for 2!"

"Wow, that will be great," I replied.

So I moved into Simon's flat and naturally into his bedroom, although we did set up "My room" for appearances sake if anybody came to visit as we were not ready to be "out" yet. We had sex in every conceivable part of the flat, including the balcony one drunken night, I think that we got away with it apart from a knowing look from one of the other residents, an older single man but he was happy not to spread rumours.

Epilogue.

Eventually, Simon's Dad decided that it was time for him to retire and handed over control to Simon. Sadly, he died a couple of years later from a heart attack and Simon inherited ownership of the company outright. He immediately made me an equal partner and we set about building the company up into an even more successful one. We eventually moved from our flat to a lovely home on the Hamble River where we still live.

We have now decided to take a backward step ourselves and have started to hand over ownership to our wonderful and loyal staff so I am writing this as we sail Solstice II around the world. We are currently drifting along in light winds with a clear blue sky heading towards Auckland in New Zealand, having just made love on deck, Simon holding on to the mast whilst I fucked him from behind, it's a good job there are no other ships about!!