March Madness at Sea

Standard disclaimers, all participants are 18+ yr. old. This was totally created in my own twisted mind.

March Madness at Sea

It was a cold winter in New England and I was recovering from minor foot surgery. A previous employer requested I do a job for him. I was a yacht captain, retired to being a local relief captain and a deliveries captain. I live modestly, I had a handsome salary for many years and my two ex-wives had spent it.

The offer was to fly to Trinidad with a skeleton crew and sail his newest acquisition to Massachusetts. Normally this would be a gravy run, spring in the Caribbean and up the East Coast. The problem was 1) nobody wanted to work for this guy, he was a royal pain in the ass and 2) Port Of Spain, Trinidad was a back water port to start a voyage from. I ran through my usual list of contacts without the slightest nibble of interest. I then got a surprising message from a controversial local captain, she wanted to meet with me for coffee at a local café. Oh, what the hell; this might be interesting.

Captain Pat was a character; she ran a charter primarily for alt groups with her mate Lydia. They lived together as a couple. Pat came up through the yachting businesses; she got blacklisted from the business because she was involved in a violent incident with the captain of the boat she was working on. Eventually she ended up buying a boat of her own and starting her own business.

Over coffee, she told me she was getting desperate for money, the previous season had been less than stellar, the bills and loans still had to be paid. She said that she could find a full crew, for the right price. I told her that I had a budget for six people including myself and there were three iron fast rules, 1) No alcohol was to be consumed from the start until we finished, 2)No recreational drugs and 3)No tobacco, including those vape things. She said that she would mate for me, Lydia would second mate and a friend Andrea would take the cook/crew position and she could easily find two deckhands, if I would have them. I've never had a problem with Pat or her lifestyle, I told her to provide me with resumes and certifications and if the owner approves we could do it.

I was surprised that Pat's certifications equaled, even surpassed mine, she had two world circumnavigations under her belt as well as six years sailing coastal New England. Lydia and Andrea both were surprisingly well qualified and licensed. The two deckhands, April and Dawn, were both experienced schooner sailors and exceeded minimum requirements.

After hard fought negotiations, I demanded taking the near shore route, which is a thousand miles longer than the direct route, fifteen days travel verses ten days travel; I justified this by having a new crew on an unfamiliar boat. I also demanded a full month's salary for myself, a first and second mate, a cook and two deckhands, health, liability and compensation insurance, all paid in advance. He didn't like the terms, my position was that they were non-negotiable, alas, he didn't any other options, he had to agree. The owner approved the crew with reservations, he told me that I would be responsible for any damage or troubles they caused.

I asked Pat if she if she would take a non-traditional position similar to that of staff captain on a cruise ship and that would elevate Lydia to first mate. It took more money out of my pocket, but it gave me more separation from the crew and transferred more responsibility to Pat. She was delighted with the offer.

It was March first when we departed Logan International Airport for Trinidad. It took two days to get there and we settled into hotel rooms, before taking delivery of the yacht.

Elsa's Dream was a 130 foot, 40 year old, traditional gaff-rigged, steel-hulled schooner, that had just come out of the yard after a complete overhaul and was freshly paint inside and out. Overall she looked in fine condition. She was well stocked with consumables and food staples, all we needed to buy were perishables and snacks.

I moved into the small captain's cabin, in the after part of the deckhouse, across from the navigation station and by the ladder (stairs) to the ship's wheel. Pat and Lydia shared a crew cabin with upper and lower bunks, up forward, Andrea moved into the crew cabin across from Pat and Lydia, the other two crew moved into the forward crew cabin.

Pat and I inspected the boat from stem to stern, keel to the top of the masts and found only a few minor discrepancies, which were easily straightened out. The engine and generators and everything else in the engine room was either new or recently overhauled, there were 2 full sets of sails, one set bent to the masts and rigging the other neatly rolled and stored in the forward sail locker, the winches had been rebuilt, the stainless steel standing rigging was all new as well as the running rigging (ropes) and ground tackle ( anchors and chains). We donned scuba gear and inspected the under side of the hull, the rudder, ships propeller and the sacrificial zincs; then went aloft to inspect the masts, rigging, blocks and other fittings. It couldn't have been much better if she was brand new.

The disturbing thing was, all of the guest facilities were out of bounds for the six of us, except for the central passageway. The doorways into the cabins were each sealed with clear plastic, we could see in but not enter. The seating in the salon was similarly sealed off as was the dining area, security tapes were on all of the drawers and cabinet doors. An extremely odd situation, but so was the owner.

The boat had already been inspected and accepted prior to our arrival and everything had already been paid for. I had operating funds available for docking fees, fuel and food, as well as a petty cash account, credit cards, for emergency use only and money to pay the crew for the next four weeks. This was a delivery not a pleasure cruise which meant keep the expenses low, try to avoid the more expensive ports and make delivery as soon as reasonably possible.

After Andrea made some last minute purchases, we motored around to the north shore of the island and anchored for the night, as part of the shakedown cruise; then sailed to Canaan, Tobago the following day. The main sail was set, then the fore sail, staysail, jib and flying jib; the main and fore topsails we left furled for the duration of the voyage. We were all experienced schooner sailors and we had no problems. Upon arrival the following day, we anchored and prepared for our departure to Granada the following day.

Andrea had settled into the galley, the food wasn't gourmet, but one hell of a lot better than I could have managed; no MRE's on this trip. I made one stipulation on Andrea, the crew could go vegetarian, as they preferred, so long as I got one meat entree per day. She put out three regular meals plus mid-morning and mid-afternoon snacks as well as evening and mid watch snacks, when sailing.

Pat and I broke out our sextants and chronometers before noon to brush up on our celestial navigation skills. I gave the crew shore leave on the condition that they abstain from alcohol and be back aboard at 2000 hrs. (8:00 p.m.), they took the RIB (rigid inflatable boat) to the town. Andrea returned at 1700 hrs (5:00 p.m.), Pat and Lydia were a couple and April and Dawn paired up, leaving Andrea as the odd person out, she returned in the RIB. Andrea and I had a quiet dinner and got to know each other better. Pat radioed me when her group was ready to return, Andrea retrieved them with the RIB.

I respected the women's privacy, almost all communications to the crew went through Pat and Lydia, except at meal times, when we sat at an open table. I did daily boat inspections when the crew quarters were vacated.

I figured that it would take about twelve hours to sail to St George's, if wind and weather were with us. We departed Canaan at six in the morning, Lydia's team took the first short two hour watch, Pat's team took the four hour watch from eight am to noon, then it was Andréa's turn from noon to four pm, then Pat's turn to arrival. Later on during the longer runs, we would do three four hour watches from eight am to eight pm and two six hour watches from eight pm to eight am; it's a hard schedule, but we weren't going to have many consecutive days at sea in the beginning, later there would be some longer legs to the voyage.

I planned on sailing during the day and motoring at night, the boat steers itself on auto pilot, you only have to adjust the sails if the wind changes or you change course and you always have to be alert for avoiding other boats, ships and unplanned events. Being short handed I didn't want to have sail evolutions in the dark. The plan was to make about two hundred nautical miles per day that means a speed of just over eight knots, twenty-four hours a day.

At 1830 hrs. (6:30 p.m.), Pat alerted me that we were approaching St George's. I went on deck to oversee our arrival and docking. We cleared customs and immigration, standard procedures for all of the islands. I was only planning to lay over for the one night. Over dinner we hashed out what went right and not so right so far.

After dinner Pat, Lydia, April, and Dawn retired to their cabins leaving Andrea alone, I asked her if this separation from the rest of the crew bothered her. She replied that it didn't, she could walk on either side of the street. I wasn't sure what that meant, so I asked her to explain. She gave me a smile and said that she was definitely bi. Why was she telling me this, was it an innocent statement or was she interested.

The next morning the crew went ashore for a couple of hours, then we set off for Basse-Terra, Guadeloupe at noon, Lydia had the first watch until four. Basse-Terra is about a two hundred mile run from St Georges, so about a one day voyage. Midway through the afternoon watch, I did a safety tour of the boat, when I got to the forward part of the main deck I was mildly shocked. Pat, her deckhand April and Andrea were nude sunbathing, to hide my surprise I casually advised them not to get sunburned and moved on. We hadn't discussed nudity on board, only that they were to be properly dressed when on watch; shoes, shorts, shirt and hat. I'll talk to Pat later about guidelines for when they're off-duty; I'm not a prude, but there are limits to propriety.

Later, during the next watch, Lydia and Dawn went up forward to sun bathe. Well, it's not like I've never seen tits, asses or furry patches before, it was just unexpected. My talk with Pat went well, nudity only on the forward deck when at sea or if we had swim call and don't get sunscreen on the teak decks. I was invited to join them; I thoughtfully declined.

We arrived in Basse-Terra in late afternoon, Pat, Lydia, April, and Dawn went ashore for the evening. Andrea and I had a light dinner, after checking the dock lines, water and power lines, I went to my cabin to rest.

A little while later Andrea knocked on my door. Andrea came in and said that she wanted some company and would I mind spending some time with her. I was sitting on the edge of my bed dressed only in a pair of shorts, I had no objections to spending time with Andrea. She pulled off her tee shirt, sat down next to me, kissed me hard on the lips and dragged me to the mattress. This was completely unexpected, I hadn't had sex for months, so I responded in kind. Over the years, I've had several female crew members make advances on me, I had always turned them down, not this time, I realized that I needed this as much as Andrea.

Andrea isn't half my age, twenty-eight as I remembered from her resume. She's average height, five foot four or five, solidly built, a hundred and forty or fifty pounds or so, a pleasant face, severely short red hair, a few tattoos, a nose ring and multiple ear rings. This was definitely not my type, but she had a outgoing personality and we both had needs.

I'm in my mid seventies, five foot nine inches, wiry, with longish white hair and beard. I was always clean shaven and had a crew cut throughout my professional career, I have a more relaxed attitude now.

She quickly slipped her shorts off then peeled mine off. I was stiff by now and she wasted no time mounting me, we had frantic sex and it didn't take long for either of us to cum, then we lay back and talked. We were still talking when the rest of the crew returned and proceeded to the forward ladder to the crews quarters. Andrea and I quieted to a whisper, secrets are hard to keep on a boat, thin walls and everyone being in close proximity. Later Andrea stealthfully left for her cabin after a much more reserved and silent second round.

Basse-Terre is the administrative capital of Guadeloupe and has some of the best French culture in the Caribbean. Andrea and I did a grocery run in the morning, fresh French bread and croissants, milk, eggs, cheese, fresh fish, fruit and vegetables. Pat was in charge of preparations to get the boat underway. Next stop Philipsburg, Sint Maarten, another one day run. We departed at noon, it was Pat's turn for first watch.

Later that evening, after Pat assumed the first night watch and things had quieted down, Andrea silently padded to my cabin, I barely heard her knock on the door. As I opened the door, she quickly slipped in and kissed me. My aft window looked out onto the steering station, I pulled the curtain closed. Sometime around midnight she returned to her cabin. At mornings breakfast, Andrea and I were the talk of the table, there was no sense denying Andréa's nighttime rendezvous. We quietly bit the bullet and endured the good natured ribbing.

We had an early afternoon arrival, Philipsburg is a tourist port, so we anchored in the harbor. Pat, Lydia, April and Dawn took a water taxi into town. I stayed on board, Andrea decided to keep me company. Pat and Lydia came back early to give Andrea and me a chance to stretch our legs and have dinner ashore. When we returned, April and Dawn had also returned, Andrea went to her cabin, showered, then sashayed bare-assed naked, with her shorts and shirt flung over her shoulder, through the boat to my cabin, ignoring the cat calls and insinuations from her fellow crew mates, she stayed the night.

In the morning we prepared to go to Puerto Del Rey, Puerto Rico, a large yachting center on the east coast of Puerto Rico. This was to be our last one day run, from there it was a three day run to the Turks and Caicos Islands, then a long two days to Nassau, Bahamas.

We departed at noon, as usual, Lydia had first watch. When I finally went below in the late afternoon, I found that Andrea had moved into my cabin. I was disappointed that she hadn't asked permission, this was Andrea, she acted and let the chips fall as they may. At the 2000 hrs. (8:00 p.m.) change of watch we did an all hands sail evolution to lower the sails and furl them securely for the night, as squalls were passing through the area.

Puerto Del Rey gave us the opportunity to wash our bedding and clothes at the Marina's laundromat, we took on fuel and water, changed filters, did a major cleaning of the galley, aired out the boat and washed down the deck and deck houses with fresh water and I called the Caicos marina to reserve dockage. I spent the evening in the marina's Captains' Lounge talking with the other captains.

There was a fat obnoxious captain there displaying a magnificent scar across his abdomen and telling a yarn about a violent mate that had stabbed him with his own knife. I recognized the lout and let him tell his tale. When he finished I said that I heard that he had tried to assault his mate when he was drunk and he stumbled and fell on his own knife. He questioned my source of information. I told him it was my mate, Pat, on Elsa's Dream, his previous mate. I told him that Pat was as competent, reliable and honest as any mate I have ever had. Andrea was anxiously awaiting my return and we retired for the night.

Andrea and Lydia did a last minute grocery run in the morning. I told Pat about my meeting up with her previous captain. We took extra care stowing gear as we were going to have a couple of days in the open ocean. We had a leisurely noon meal and finally got underway at 1330 hrs. (1:30 P.M.). Pat had the watch, she called out, "Hey, fat ass," and gave the finger to her previous captain as we passed his boat.

The next couple of days were basically sails up in the morning and down in the evening, oversee the watches, eat, clean up, sleep and keep Andrea happy. We were making good time, the wind and current were with us, so good that if we continued at this pace, we would arrive in the middle of the night. We were in the Caicos Bank, a shallow area west of the islands, I decided to anchor for the night and approach Providenciales Island, our destination, the following day.

We were all looking forward to a night without the constant drone of the engine and generator. With light winds and the anchor embedded firmly in the sand, Pat requested swim call. I had mixed feelings about this, the swimming part was good, but having five naked women around me, I wasn't sure. I agreed and went below and put on my trunks. Once on deck the women were disapproving, "We're all adults," Andrea scolded as Pat crept up behind me and yanked my trunks down to my ankles; this was gross insubordination, and I was enjoying it. As I rose to the occasion the crew saluted Captain Dick.

It turned out to be an uplifting experience swimming with five playful water nymphs and the abundant physical contact. I was anxious to have some contact with Andrea, but she kept pushing the other girls at me. (I've avoided calling my crew women, girls, out of respect, now we were playing, it seems more appropriate.) As I fended off the attackers in front of me, others groped me from behind, rubbing their tits and bodies into me. I returned to the boat exhausted. As I lay on the deck the girls continued to assault me with kisses, fondling me and one even went down on me, all I saw was a dark head, four out of the five were dark, Andrea the exception. Finally they withdrew and permitted Andrea to do what she did best and with a full audience. This was turning out to be the most unconventional trip I'd ever been on. That night Andrea apologized for the girls getting out of hand, but she wouldn't identify who went down on me; that night she continued being playful.

We kept an anchor watch that night and set sail at first light. We arrived at the marina in the late morning. Pat, Lydia and Andrea went ashore for some R&R and to pick up provisions, Andrea said April and Dawn would take care of things on board. After lunch, I was lounging on some cushions on deck, reminiscing the previous day. Dawn suggest I roll over on my stomach so she could massage my back and shoulders, after yesterday's experience, I felt comfortable with the offer. Minutes later two more hands joined the party, April suggested that we take it below away from prying eyes. They half carried me to my cabin, striped me then themselves, what could I do, I was outnumbered. Actually I prefer being a lover, not a fighter.

When Andrea got back, first thing she asked was if April and Dawn took good care of me. I admitted they had, very well, very well indeed. She confided that April had a few previous experiences with men and Dawn was a virgin, where men were concerned.

We stayed an extra night as we prepared for the next leg of our journey. Navigating through the Bahamas can be dangerous, coral heads, shallow water, I needed at least 12 ft. minimum of water to stay afloat, as well as drug smugglers. I plotted and outlined our courses along with GPS coordinates to get us to Nassau, I wanted to be briefed on our position every two hours on this leg of the trip, the chart plotter in my cabin would be helpful. I gave Andrea the option of returning to her cabin, she declined.