The Sailing Sextet


This is a true story that spends a great deal of time talking about sailing. It will have a ton of sex thrown in but I would hate to have you disappointed in thinking that it was going to be an over and over slam-bam thank-you-mam kind of a sex story. I’ve tried to throw in the landlubbers’ description of nautical things whenever I thought it was needed.

We were having major modifications to our 42 foot Pearson sailboat at a yard up at the head of Buzzards Bay prior to our trip from Massachusetts to the Bahamas. Sam and I both had full confidence this yard would do excellent work. Besides, we knew the owner of the yard and he was doing the work for nothing more than the salaries he paid his workers. That saved a bunch. We also were having them check over the hull as well as the rigging holding up the mast. Having the work done up in Massachusetts was going to add almost 400 additional miles from our homeport outside of Annapolis, Maryland but we felt the safety of having this particular yard do the work more than justified the extra few days of sailing. What the hell, it was designed to be a pleasure trip rather than simply transporting a boat anyway.

It’s over an 1100-mile sail and in addition to having it inspected we wanted to have everything on the boat in tip- top shape as well as having a few nice additions installed such as a fresh water maker that would convert seawater into drinking water. In addition we were having the icebox converted into an honest- to-God refrigerator/freezer. Our sundowners would then have the clink of ice-cubes rattling around in the glass.

I’m Jan and Sam and I have done a ton of sailing together and we had been talking about this trip for what seemed forever. I had bought the boat the year before and we had done a lot of work on her freshening her up for the trip. Sam and I have been “an item” around our local yacht club for a few years and we do get along well and do a pretty fair job of handling a boat the size of the “Harmony”. Each of had taken a month leave of absence from our jobs figuring the downward leg would take at least eight days and then we wanted to spend a few days around the Islands before heading back on the 900 mile return trip to Annapolis.

We had rented a car for the trip up to the yard from Annapolis and would have the yard guys return it to Hertz for us. I had spent most of Wednesday shopping for the food list we had prepared so we were going to drive up on a Thursday and then spend Friday and Saturday loading the boat. In addition we wanted to go over some of the changes the yard had made with the workers before casting off on Sunday morning.

Our first night dinner in Mass. was going to be special. We were going to treat ourselves to a great lobster dinner at one of the local seafood restaurants we had enjoyed on other times we were in that area. The last time was a few months ago when we brought the boat up for the yard to get it ready for our trip. No touristy spot for us; we wanted to eat as the locals did and pay local prices rather than the exorbitant rates the tourist spots charged.

As we walked in the door to the restaurant we were greeted with a big,

“Hi, haven’t seen you guys in a while.”

It was Sally, the waitress we had on previous visits and she honestly seemed glad to see us. She’s a gal of 23, with a great shape, very thin but pretty. She quickly ushered us to a favored table by the window overlooking the harbor.

It was early and we were the only ones in the place so she sat down at our table with us asking,

“Well, tell me about it. Are you up here to make the big sail you talked about during your last visit?”

Sam jumped in with; “Yep and we shove off on Sunday morning.”

“Oh Gawd, I’m so jealous I could explode. You will remember I told you I had made a couple of trips like yours with my folks when I was younger and loved every mile we sailed. We only had a 33 footer and if I remember right you guys will be enjoying smoother and faster sailing on a larger boat.”

I answered, “Yeah, you’ve got a great memory. Our boat, Harmony, is a 42-foot Pearson and is pretty well equipped. We just had refrigeration and a fresh water maker installed so we will be able to have some cubes for our sundowners.”

“Oh man, you guys are sooooo lucky.” She cooed.

Dinner went great and we thoroughly enjoyed the lobsters.

Sometime during dinner I questioned Sam about the possibility of asking Sally if she would be interested in joining us. Sam and I have sailed many overnight trips and it gets awful lonely in the cockpit in the middle of the night when you are out there with no one to chat with. Besides, she sounded as if she had had a good bit of sailing experience and that could be a huge help. Sam responded that he would think it over.

We hit the sack fairly early and the sun was up in all of its glory when we were back out in the cockpit. Sam seemed all excited as if he had something on his mind he had to share.

He Anadolu Yakası Escort started the day off with, “Jan, I thought it over last night and I think it would be a super idea if Sally would join us. I do know the loneliness than comes over each of us when the other is sacking out below and we are out in the cockpit talking to the stars. If you still think it is a good idea why don’t you go over to the restaurant and leave a message with whoever is working this morning to have Sally call you on your cell phone.”

We were both in the yard office settling up our bill when my cell rang. It was Sally and I asked if she would come down to the boat right away for we had something to talk to her about.

She was sitting in the cockpit waiting for us before we even made it back to the boat after paying our bill. She looked nervous as hell.

“Jan, you ask her. I think it would be better coming from one woman to another.” Sam whispered as we were walking down the dock.

Jan barely got the invitation out before Sally was screaming with joy.

“Yes, yes, yes. I know you won’t be sorry.”

Sam followed on with, “There is one question and that regards your passport. I hope you have one and this is a weekday so if you have it in your safe deposit box you can get it out before closing time.”

She came back with, “That won’t be a problem. It is in my dresser drawer in my apartment. But there could be another problem. I don’t have any money to throw into the travel kitty. I could probably scrape together a couple hundred bucks but that would have to go for my share of the food and booze but I would hope to have a couple of bucks left over for restaurant meals in the Bahamas.”

“Sally, you are going to be our guest. We asked you to join us so you won’t be expected to throw in one cent for travel expenses. Any money you have can be spent however you would like to. OK?”

The tears were rolling down her cheeks as she murmured “Thank you so much.”

It was Sam’s turn again as he told her that there could be something that could turn her off but it would be up to her.

“Sally, as soon as our boat is away from any other boats I strip naked and sail that way until it either gets too chilly or we come close to civilization on either land or other nearby boats. Jan sometimes joins me going sans clothes. We also sleep in the nude so you will probably see us going naked from our bunk to the head during the night. We wouldn’t embarrass you by doing anything of a sexual nature in front of you. So, there it is, the choice is yours.”

“Are you kidding me? Who knows, I might even join the Harmony nudist camp if that wouldn’t bother you guys”

We all roared.

Sunday morning couldn’t have been better. We had about 15 knots of wind out of the northeast and the yard owner and the guys who had worked on the boat were all at the dock to see us off. They presented us with a box and told us it was to opened on our first dinner at sea. It was a touching few moments and even Sam had watery eyes.

We were going to clear Buzzards Bay and enter the Atlantic in early afternoon and things were going superb. The boat is quipped with an auto-helm that enables us to set a course, press a button and the boat will then steer itself on that course until we change it. There was a lot of other boat traffic just west of Martha’s Vineyard but that would clear up as the afternoon wore on. Those boats would be heading back into Long Island Sound or to the harbors along those coasts.

We were making an easy 6.5 knots with the Northeast wind and were going to have Montauk Point at the eastern end of Long Island off our starboard beam (side) around four in the afternoon. From there it would be almost due south to the Bahamas. Other than the shoals around Cape Hatteras we would hug the coast as we got further south to avoid the effects of the Gulf Stream. It is an ocean current that hums along northward at over five mph and can almost stop a slow moving boat in its tracks if it tries to go against the Stream. A great sail coming up!!

Sally fit right in. Her previous experience on her Dad’s boat showed she knew what she was doing and was obviously comfortable around all of the mysteries of a sailboat on the open ocean. Besides that, she bent over a couple of times in front of Sam and I could see his eyes bug out as her tiny ass was staring him in the face. There was little doubt in my mind that he would introduce that tiny ass to his cock before this voyage was over.

Sam was up on the foredeck and yelled something about dinner.

“What are you asking Sam, we can’t hear you very well back here?” Sally asked.

He came back to the cockpit and said, “Well, we never did agree on who was going to do the cooking.”

Sally jumped up saying, “You don’t want me to do any cooking at all. I stink at it but I am a damn good waitress as you guys know from the restaurant.”

I couldn’t let that go and had to chime in with Bostancı Escort “Sally, it will have to be either you or me cooking. That clunker, pointing at Sam, couldn’t boil water. What do you say that I’ll do dinners and you take care of lunches and breakfasts?”

“Fine, I can certainly make toast sandwiches and fry eggs.” She said laughingly.

It was now right at supper time and we were just south of Long Island and we were soon going to be encountering major commercial ship traffic out of New York harbor. I would rather have us enjoying dinner rather than being constantly occupied with being on the lookout for commercial traffic. We were equipped with a great radar system but I have always felt that I would rather have my eyes and mind judging how close or far another ship was going to come to us rather than trust some goof ball on the bridge of some foreign flagged tanker.

“OK, I’ll make the dinner and Sally you can dig out a bottle of Merlot. We are in for Italian tonight.”

Sally yelled out, “Hold it, the guys at the boatyard gave you that box and asked that you not open it until the first dinner on the boat. Remember?”

Sam responded with, “You’re right sweet thing. Let’s see what it is.”

His “sweet thing” response gave somewhat of an indication what was in front of them.

He ripped the wrapping off and lo and behold found two bottles of a very nice Merlot and a great bottle of champagne. What a great boat yard! It was going to be Merlot that night for we certainly didn’t have enough time to get the bubbly chilled.

It was only four PM and we were still making six and a half knots. The wind had stayed the same all day and Sam had just stripped down naked as we cleared all of the commercial tanker traffic outside of New York harbor. Sally apparently got a good look at him naked and came up behind me as I was getting the pasta ready and whispered,

“How can you do it?”

I turned and asked, “What do you mean?”

She nodded her head in Sam’s direction and said with a huge laugh, “You have a great looking guy and I just saw what could probably rise to be able to serve as another mast for this boat. I’ve only had sex with one guy and that was only three times and I couldn’t begin to even think of anything that large getting pushed up inside of me when it got hard. Whew!”

“Oh yes, it took me a while to be able to handle it.” I answered with a laugh.

Sally set up the cockpit table and got it ready with silverware, napkins and glasses just about the time I was ready with the dinner … linguine, my special tomato sauce, and fresh bread and butter. Along with the Merlot we were ready for a feast.

The dinner in the cockpit (there’s an appropriate name) was fantastic. There were a few other boats within sight, a couple of which were heading in the same direction as we were but they were a few miles off our port beam. (left side) The wind kept up the way it was all day and the sun was setting over the coast of New Jersey for the first day of our sail.

It was getting somewhat cool for Sam so he ducked below and pulled on a sweatshirt along with a pair of jeans.

I have noticed over the years when the sun goes down over the water, whether it be a lake, bay or the ocean, it gets cool very quickly. It didn’t get dark until after nine PM and we sat in the cockpit enjoying the stars and great conversation. We have a rule that no alcohol will be consumed after six PM when we are underway. It was agreed that Sally would make a fabulous breakfast that would be ready out in the cockpit at eight- thirty.

By then we were running under navigation lights that call for a white stern light as well as a red and green running light. Sam had made a significant change in that he had a white strobe light installed up on the mast- head; the kind you see on school busses or other emergency vehicles. The normal red and green running lights are impossible see at anything other than close distances but he left them installed just to be somewhat legal. Large ships, unless they are looking for those kinds of lights, have a tough time spotting them. Other boats would now see us at night but we would have to be careful to have the batteries charged for those lights during our daylight hours when they wouldn’t be used. To save our batteries he had had the strobe modified so that it didn’t flash as often as it would in its normal usage. We also had several solar panels installed on the bimini top to gather sunlight for battery charging so as long as we had sun, the batteries were being charged.

Our conversation ran the full gamut of sex and sailing. Sleeping facilities on the boat were similar to that on other boats of this size. There was a set of joint berths up in the bow, called the V-berths that Sam and I would be using. We decided that Sally would be best in what is referred to as a quarter berth that is a berth that goes under the cockpit seats with the head end extending out into the cabin.

Before Erenköy Escort turning in Sam made sure our course was still proper and that the sails were set for the winds we were experiencing. He even rolled up the genoa (foresail) a few turns to shorten it for the heavier winds that were forecast during the night. Sally volunteered to take the first watch that was going to be from ten PM until two AM when Sam would change with her until 6 AM. I would come on then and let Sally sleep until around eight AM when she would be getting breakfast ready. So Sally was out in the cockpit when Sam and I retired for the night. We weren’t away from the dock a full day and we were changing the reason we had invited Sally. Our original idea was to have two people out in the cockpit during the night for company and we had just changed that!! Well, we could always change it back if we wanted.

He and I were no sooner in our bunks when I felt his hand work its way over and under my sweatshirt and began to massage my breasts. Mmmm, he knows I love that and I reached over and took his cock in my hand and began sliding it up and down the shaft. He let out a loud moan that I felt sure Sally heard. The next thing I felt was him sliding down in the bunk and pulling my shorts down as he got to the foot of the bunk. He soon had his face buried between my legs with his tongue doing its magic on my clit. He soon had me so hot I was biting my hand to keep the noise of my moaning from reaching out to the cockpit. He did that for a couple of minutes and then pulled up and rammed his rock hard cock in me in one smooth thrust. I couldn’t hold back. My shriek could have been heard miles away never mind just to the cockpit. He pumped me for what seemed like forever but it wasn’t long before we were both exploding. Whew, I do love his dick.

The changeover between Sally and Sam apparently went pretty smoothly with no mention of her hearing our moans and groans.

The wind and weather stayed the same during Sam’s watch with the exception that the wind switched around a bit so that is was now coming more to the east. We would soon be on a broad reach point of sailing and as long as it stayed at the same speed we would be in terrific shape. We were now clocking right at seven knots. WOW. Sailing couldn’t be more enjoyable than it was right then … the wind was at a perfect speed and out of the ideal direction.

It didn’t take Sam long before he went below and stripped for the day. The temperature was forecast to be in the upper eighties and there wasn’t a cloud in the sky. He came part way out of the companionway hatch with a tube of sun-tan lotion in his hand and asked Sally to smear some on his back. I knew exactly what he had in mind and he didn’t disappoint me.

He turned his back to her and passed the lotion over his shoulder to her. When he felt her finished with his back and her hand was low on his back he quickly turned to face her while her hand was still down in the area of his cock.

“Don’t stop now Sally, You are doing great.” He said with a huge smirk plastered on his face.

He wasn’t hard but he would be in a minute if she dared to touch his cock. “Oh, I think you can handle the rest very well yourself Sam. That is if you aren’t too sore from last night” she answered

She and I laughed for a good while as Sam climbed out of the hatch and went forward up to the foredeck; I guess to pout.

Sally and I sat in the cockpit during the rest of my time on watch just chatting when I said that it was getting warm enough that I was going to get rid of my clothes and join Sam in nudity. Sally asked if it would present a problem if she too joined Sam sans clothes.

“Join the crowd Sally. I’ll get some lotion on your back if you’ll do the same for me.” I answered. It wasn’t five minutes later there were three nudies handling a great forty- two-foot sailboat on the way to the Bahamas.

I hadn’t seen Sally nude before so I guess it was natural for me to look at her body in detail and compare it to my own. She was slim but had perfect proportions. Her breasts were a nice handful and looked very firm. She had shaved most of hr pubic hair probably for wearing a bikini but she had left a strip just trimmed close but not shaved. All in all a very nice shape.

She stretched out on the port cockpit seat and as she lay there we continued to chat. The radar screen was showing a few boats off to our left but there were a pretty good ways off. There were a couple of small boats off to our right side but they too were a good ways off. We had our section of the ocean all to ourselves.

When we are alone on the boat and Sam needed to take a leak he simply stood at the stern with one hand holding on to the backstay for support and let it fly over the stern. I guess since we had a guest aboard he thought it prudent to go below and use the head. He wasn’t down there very long before Sally asked me if I cared for a drink. I agreed to a Coke and she got up and went below to grab a couple.

She had one in each hand as she started back up the companionway steps when Sam appeared right behind her. The next thing I saw was his hands reached around her and cupping her breasts saying, “Wow what great handles.”