A Sailing Story Ch. 01

They all said goodbye as Lisa and Jane went below. Guy was finishing up in the galley and put on his sailing top ready to go.

"You did real well for me. I want to meet you on Wednesday next to discus food supplies and once again thanks," I patted him on the back and away he went.

"Ok Jane, this is the way it is, you're not pulling your weight and although you're a great fuck, you're not going on the trip." I rasped.

Janes' mouth dropped and I thought Lisa was going to pass out.

"You bastard! You rotten bastard," Jane yelled.

"So sue me why don't you!" I hit back " now get off the boat and don't let me see you down here again and by the way the marina police will be looking out for you if you do try"

"Fuck you!" she shouted back over her shoulder as she jumped onto the pontoon.

"Not very ladylike was she eh?" giggled Lisa " but was she as good a fuck as you made out?"

"Well no she wasn't, but I wanted to let her down gently, " I said and laughed out loud.

"You are a bastard aren't you?" said Lisa.

I shrugged my shoulders and said "fancy another glass?"

Lisa flopped down on the thick leather seat and waited for me to pour her a large whisky.

"Do you fancy making an evening of it?" she asked.

"Lisa that would be very nice," I said and settled back on the seat.

"Ok lets go into the main cabin and get to it, you hunky bastard," and she hurried into the main cabin aft flinging off her top as she went.

We fucked for the world, most of the evening, and drank so much whisky and wine our heads were swimming. What a woman and she showed me new tricks with her tits, but more of that later. We fell asleep on the bed and didn't wake up until around 9.30 the next morning.

"You OK?" I said as I opened my eyes and turned towards her.

"You bet I am," she said "are you?"

"Yep, this is going to be one hell of a trip, I can feel it."

"You can feel it at this time on a morning," she said and chuckled.

"I can feel it if you'll let me," I said laughing and tickling her belly.

Boy those tits looked even better in the morning sunlight.

A week passed slowly and on the Wednesday I opened up the deck hatch and put out the pontoon steps. I had hardly set foot back into the steering flat when I was startled by a cheery "hi there".

It was Guy in a brand new set of sea clothing.

"Hi, the early bird and all that," I said.

"Well you said get here on Wednesday and here I am," he answered.

We went below to the main saloon and sat next to each other on the bench seat on the port side.

I laid out previous trips supplies and then he set out some work he had done during the past few days.

I was impressed. He had done his homework well, not only that but he was a good $300 a week cheaper than my estimates.

"How come I asked?" I asked.

"It's a question of when where and how and of course bargaining," he said.

I noticed he was coming closer along the seat as he showed me the documents. My hand rested on his shoulder as he explained the figures to me.

He turned to me and made as though he was going to kiss me. I pulled back quickly.

"I'm sorry," he said " I thought you were, you know."

"That's Ok don't worry, isn't that Paul Smith your wearing?" I queried.

"Yes it is," he answered "you like it?"

"I do, it's very nice," I responded and he quickly leant into me and kissed me on the cheek.

I looked slightly startled but didn't pull away, he took that as a slightly more encouraging sign and did it again.

I don't know what happened then but I kissed him back and yes, before I knew it, he had his hand on my cock and was stroking it through my cropped shorts.

His hand disappeared up the loose leg of my shorts and in a second he had a full handful of my cock. I have to say it felt good. Not since second year high school had a guy had his hand on my cock, but schoolboy wanking developed into an art form at my high school and I was in the thick of it.

He twisted and milked my cock until I could stand the constraints of my shorts no longer and slipped them off onto the floor.

He took a new hold on my cock and with what can only be described as precision, jerked me off until I shot my load straight up in the air.

He quickly slipped off his pants and there was a beauty of a cock, glistening with precum on the end and waiting to be thrashed.

I obliged by taking it in my right hand whilst rubbing his sack with my left hand and rubbing his cock end with my first finger. He loved it and in no time at all he blew his load all down my fist and arm.

"Thanks for that I hoped you would," he said.

"You did?" I responded.

"Maybe we can do more as we sail away across the seas?" he asked.

"Maybe we can," I said.

Thursday saw the stores brought on board and packed away in the storeroom and galley.

The boat filled with fresh drinking water and the diesel tank topped up ready for the off.

Friday arrived and the first on the scene was Sheila, a rough tough looking girl about 26 or 28, with fair shortish hair, a good figure but not spectacular.

"When you get stowed below get out your passport and let me check it out," I told her.

"Which cabin and which bunk?" she asked.

"As long as you don't try to get the main cabin the answer is any and any OK?" I shouted "first here first choice."

"Cool," she responded.

In minutes she was back on deck in the steering flat with her passport.

"Mmmm English born and not too far from where I was born," I said to her.

"Really?" she queried.

"That looks OK, I keep them in the ships safe until we dock, saves all the hassle with customs etc," I told her.

The rest quickly followed on and I did the same with all of them. I realised that I had left mine in the locker in the marina and hurriedly left the boat to get it. Wow that would have been a good one for the skipper to be without a passport in a foreign port.

Stood at the fence looking through the wire mesh was Jane, she stared at me with those intense big dark eyes.

"Are you sure I can't go?" she asked.

"I am Jane, don't take it personally, you were just not up to it by comparison and I'm not carrying passengers, all the crew have to work in unison and you couldn't. You were a great fuck though and I appreciated that," I said.

"Ok," she said mournfully "fuck me when you get back eh?"

I didn't speak but kissed her through the wire and waved as I turned towards the boat.

We sailed out of the marina on Friday 20th at 0900 EST. a bright flawless morning with sunny skies and a fresh westerly breeze.

We weren't in a rush to get there, so our course would be Bermuda first, then the Azores then Gibraltar and then take fresh instructions as to where we end up in the Med.

Myself, Lisa, Dave, Sheila and Guy were the crew and I had worked out a watch pattern so that there were always two people on duty during daylight hours and one person during darkness with a first call backup. The electronic gadgets on the boat had a watch keeper system so that the single handed night turn had to strike a button every 15 minutes to stop an alarm going off. This ensured he or she was awake and paying attention, lets see how it goes during the trip.

The day was passing without incident and Lisa came to chat to me.

"Fancy a quickie?" she said.

"That's the best offer I've had so far today," I said.

We slipped into the main cabin and I slowly stripped her and she stripped me. God those tits were to die for.

"Let's do doggy," she said.

"Ok let's do doggy," I replied.

She turned and knelt up, holding the bunk top rail to steady herself. Her pussy was leaking and I hadn't really realised she was such a hot lady.

My cock was hard in no time and I fed him into her warm waiting hole. It slid in so easily with all her pussy juice helping. Just an inch or two to start and then I gradually launched it in to her. Soon we were banging away at ten to the dozen. Stroking her clit with her other hand as I ran my fingernails up and down her spine, she yelped with pleasure and started shouting 'fuck me fuck me' far too loudly. I covered her mouth with my right hand and rubbed her clit with my left as I pounded in and out of her.

She exploded almost at the same time as me and as I slowly pulled my wilting cock out a great load of cum slowly dripped out of her pussy.

"Nice, very nice," I said.

"You're still doing it good," she said panting and drawing breath.

We went back up on deck and sat on the aft seats.

Sheila came to me and sat on my left.

"You know we all enjoyed that one," she whispered and laughed in my ear.

"Were we that noisy?" I said.

"Well I don't think the people in Oregon could hear you, but we never missed a beat," she said "If its any consolation Dave has gone to the heads to jerk off and I'm so wet I thought I had peed myself."

"Wow, well thank you for sharing that with me," I said and laughed out loud, Lisa wasn't sure what to do but there was no going back so we just toughed it out.

Sheila went onto the fore deck and it was obvious what she was doing in her pants, rubbing away frantically then a gasp and she laid back down full length on the deck.

Dave came out of the heads looking kind of sheepish and went forward to where Sheila was laid on the deck. They chatted for a while and then they were sat much closer together.

I got lost in the sailing but obviously Lisa was keeping an eye on things and she nudged me in the ribs and nodded forward. It looked like Sheila had her hand down Dave's pants and was at the least, giving his cock a stroke. Dave strained back and very soon he gasped and lay back on the deck. Sheila lay next to him and they were talking and laughing.

Lucky Dave I thought.

I gave Sheila a new look over as she lay on the deck. Not huge tits but full and firm, she was heavy set with muscular shoulders and back and long long legs. Trouble was they had always been covered up by trousers, so at the next port of call, Bermuda, we would have to have a dress up evening to show off the ladies charms.

Guy seemed to be the only one not talking about fucking and that made me wonder why, perhaps he was gay, perhaps he was bi with strong leaning to gay – who knows. Within minutes however, he appeared at the companionway with a raging hard on shouting "First sitting for lunch!"

"Did you see what I saw Lisa?" I queried.

Lisa hardly stopped for breath and was gone into the saloon before I could say anything. I saw her using her skilful hands to grope the front of Guys pants which were really tenting.

The others were still getting to grips with getting off the deck and were lazily making their way towards the saloon. Meantime Lisa was fast bringing Guy to a climax, but he pushed her hand off as he saw me looking.

Dave and Sheila went below as Lisa popped her head out of the hatch.

"He's going to save it for you to do!" she said winking and laughing as she returned to the table.

When second sitting was about to be served there was only Guy and I at the table of course and he looked at me with puppy dog eyes waiting for me to stroke him.

I hadn't actually sat down when he pulled me towards the cabin he occupied. He placed one finger across his lips, telling me to be quiet.

His pants and boxers were off in a second and in a single movement he pushed me backwards so I was sitting on the edge of the bed. I was almost level with his cock and he took a pace forward until his solid rock hard cock was about an inch from my mouth.

What could I do but let it slip all wet and hot between my lips and I sucked and licked it for all I was worth. He came in a matter of minutes a huge creamy load of sticky come.

"Don't go down on me we have to get our meal and make this look simple, not complicated," I said.

He pulled up his boxers and pants and made his way back into the saloon.

After lunch I went back on deck to the steering flat, where Lisa was.

"Good lunch?" she said.

"It was, he's good isn't he?" I said.

"At cooking or cock sucking?" she said.

"Both," I responded.

Lisa went below and was talking to Guy for about 20 minutes or so.

"OK he's going to join us in our cabin tonight for some adult fun, that's if you don't mind?" she said.

"Sounds good to me," I said.

Evening came and the three of us went to the main cabin after a great dinner and some vino. Dave and Sheila were on duty for the night turn and we had the below decks to ourselves. Lisa started to strip to her underwear and so did I, Guy was a little slow off the mark and Lisa started to help him.

She had both of us down to just boxers when she slowly tugged mine off completely and then turned to Guy.

"Can Phillip take mine off Lisa?" he said.

"Sure why not," she said.

I tugged his boxers down to his knees and they fell the rest of the way and he stepped out of them. His cock jutted straight out from his body, the benefit of youth I thought. Mine was hard and sloped slightly downwards from my body. Lisa took off her bra and pants and came towards us both dropping down on her knees and taking hold of both cocks at the same time.

She sucked us both with a new frenzy, but Guy was more interested in tweaking my nipples and playing with my chest hair. Lisa sucked, oblivious to what was happening further up our bodies.

This was a huge turn on for me and I had to stop Lisa sucking my cock any more and begged her for a rest. I suggested that I give her pussy a good licking and she lay down on her back on the bunk. I started to lap at her pussy but without any pre warning, Guy slid under me and started to lick and suck my cock. I have to give him credit, he was a million times better at it than Lisa. He was so good that just a few seconds of this brought me to the edge. We were all very close to coming when without warning the single man alarm went off and I flew out of the cabin and out onto the steering flat. Just as I climbed the steps up, the alarm was switched off.

As I came level with the wheel, Sheila was stripped below the waist and so was Dave and he had a raging hard on. It was obvious where it had been a few seconds earlier as her pussy was wet and glistening in the failing light of dusk.

"What the hell, you two!" I shouted.

"Sorry," said Dave.

"Nice cock!" said Sheila.

It was only then that I realised I was naked and yes, I did have a raging hard on as well.

"Don't let it happen again," I said "you'll give me heart failure."

"If we don't Lisa will," Sheila said.

"Don't be so bloody cheeky," I said and went back to the main cabin.

Lisa was hard at work sucking the rocks off Guy and he seemed to be enjoying it, at least more than he was before.

I stood behind him and held his cock straight so Lisa good get a good suck at it. This turned him on big time, and he pressed back against by now cold body. He took my cock in his hand and stretched it, pulling the foreskin back and forth over my mushroom head.

Lisa was sucking and rolling her tongue over his cock and he was bucking and writhing in her mouth. His left hand took my left hand behind him and he rubbed my hand over his ass cheeks and then into his crack. I knew where he wanted me to go and my fingers started to open his cheeks so I could get a finger into his ass.

"Oh yes, Oh yes," he said as he felt my finger slide into his ass.

Lisa was still sucking and licking like a mad thing at his rock hard cock. His hips started to buck and writhe as we both dealt with him. In a couple of short strokes he shot his creamy come all over her tits face and stomach. His ass had clamped up on my finger like a vice and my mind had, just for a second, wondered to 'what would have happened if that had been my cock' scenario.

His now wilting cock slipped out of Lisa's slippery mouth and hung there leaking a string of come from his slit. Lisa rubbed her face and tits on a towel and turned her attention to my cock. In seconds she had it in her mouth slobbering her spit all over the end and sucking just about as hard as it was possible to suck. Guy slipped his arm round my waist and slapped my ass, his other hand circled my cock at the root as Lisa dealt with the shaft and tip.

He stretched my cock back as far as it would go and gave Lisa just the mushroom head to play with. He stuck his middle finger into his mouth and drenched it in spit then plunged it straight into my ass hole. He thrust it in and out and produced an incredible itch in the roof of my mouth as he slid his finger in and out of my hole.

In a matter of minutes I had come and dribbled my load over the two of them.

We heard moans and groans from up on deck and realised that Sheila and Dave had also reached their climax.

Sheila came down the companionway to visit the heads, with no clothes on.

"Nice one Sheila," Lisa said.

Sheila was in too much of a hurry but came out in a minute or two, still naked but smiling.

"Can I join you?" she asked.

"You sure can," I said.

She sat on the edge of the bench, opened her legs real wide and took my cock and fed it into her pussy.

I fucked her so hard I thought my brains would fall out. She loved it as she gasped and bucked and twisted on the seat as I slid in and out of her. Lisa and Guy were still playing but watching us from the other end of the bench. Lisa slid along the seat and started to rub Sheila's pussy lips with her hand. Sheila came in a matter of seconds. Her back arching up until she was banana shaped on the seat. She twitched and shuddered as she came and sprayed pussy juice all over me and Lisa.

This was hot.

This was sexy.

This was no more than a quarter through the journey.

Would I make it to the Med.?

Would I eventually fuck all of them?

And I was the captain in charge!