Occasionally I place a classified ad hoping for paying charter guests. My normal motivation is that I want to buy something totally frivolous and unnecessary, usually some sort of electronic gadget – a UHD TV comes to mind. So far I’ve been pretty lucky; none of the half-dozen charters that I’ve hosted have been people that I would have wanted to drop off in mid-sea. Having arrogant, demanding guests that expect me to wait on them would probably be good to teach me some much-needed humility, but so far I’ve been lucky.
Recently I received an email query from a couple about a week’s charter. I was surprised, as I hadn’t placed an ad. It got me thinking about that UHD TV, though. The letter was signed 'Mandy and Bob Rogers'. They specified that they wanted to be somewhere where there would not be big winds or rough seas. That’s a bit of a tall order in the Aegean in the summer. The northerly Meltemi winds blow hard for periods from two to six days - usually several six day contiguous periods. Going downwind, south, is usually no problem, most people think it’s euphoric, but upwind is pure torture in anything smaller than the QE2. Well, I don’t like it, anyway.
I had planned to meet a friend on the island of Samos around their cruise date, so I suggested a cruise south from Samos to Kos and gave them my standard song and dance about the islands along the way. I’ve done this many times before and I like that island string a lot - Patmos, Arki and several others. Previous guests have always enjoyed that itinerary as well. I referred them to my web site where they would find more information about destinations, contact information and my bio.
A few days later I got a call from a woman who said her name was Mandy, and said that she had asked about a charter. She sounded very pleasant. This would be the first time that they would be on a sailboat and she wanted to be sure that they would be comfortable with me. Sounded reasonable. Some people see my picture on my web site and assume that I’m just another harmless romantic on a sailboat in paradise. Works for me.
But Mandy was much more thorough than that. First, she wanted to be sure that she would not be spending time hanging over the rail feeding her last meal to the fish. I assured her that that would not be happening. (I didn’t tell her that it was because there are no more fish in the Aegean.) Then she started to ask personal questions - my education, what I used to do for work, etc. She said that was to confirm she and Bob would have subjects that we could talk about.
I used to run the IT department at a large corporation. I’m reasonably over-educated and I try not to be too overbearingly pompous. Sometimes it works. My political views are very different from when I was a corporate manager. But now nobody cares about that. Normally it’s more interesting that I can fillet a fish. Or it would be if I knew how to fillet a fish – I can’t. Fish laugh when I cast my line.
Anyway, at the end of our conversation I felt as though I had been on a job interview. I asked Mandy, “Well, Mandy, did I pass the interview, will you hire me?”
“From everything you’ve said, I think we are a perfect match. Yes, you are hired.”
The cruise was scheduled for the beginning of July, in two months. I told her I would send her all the information and would help them make flight reservations, if they wanted. She assured me that they would be fine.
I brought Comfortably Numb up to Samos early to spend time with an old friend who had also bought a floating retirement home. I had been around the southern Dodecanese Island of Symi and, to avoid getting hammered by the Meltemi wind, I would weigh anchor at first light before the wind came up and make shorts runs north.
The Rogers’ flight arrived late in the evening, and we had made arrangements that on the first day we would just tour Samos to allow them to get over jet lag. They came from North Dakota in three legs and would be tired. I rented a car late in the day and drove to the airport to meet my guests, planning on spending the following day driving them around the island until I had to return the car twenty-four hours later.
I figured that they would recognize me from the picture on the web site. There aren’t that many tall, white-haired men – people sometimes ask me what brand of hair color I use – waiting at the gate. A woman whom I guessed to be in her mid-thirties walked up to me and asked, “You must be Captain Fred?”
I recognized the voice as Mandy’s and replied in the affirmative.
“Is your husband hung up in customs?”
“No,” she said, “Bob couldn’t come. It’s a long story. I hope you won’t mind taking just me; I assume that the cost is the same, one or two people.”
I was a little surprised that Bob didn’t have a problem letting his attractive and, from our phone conversation, intelligent wife pack it in from Bismarck to Samos, Greece, to spend a week with a man of questionable morals on a sailboat in the hot sun in terminally cute places. Begs for infidelity. I didn’t bring it up.
“It’s not a problem at all. I rarely get lady guests, and it will be a pleasure to have you aboard.”
I asked her about any prior boating experience. She had none. Why would a woman from North Dakota, who had never been on a boat and never traveled outside the US, want to spend a week on a boat with a man? She seemed nice enough, the week was pre-paid, so no problem for me.
When we got back to the boat she said that she was totally wiped out, and could she sleep late? I said that I would not expect anything else. The quay at Samos is not the most quiet place to tie up. Directly behind the stone quay where boats ‘Med-moor’ is a narrow road leading to nowhere, and on the other side the traditional row of Greek tavernas. Unlike in Turkey, in Greece such establishments don’t try to outdo each other playing loud, tacky music. Mandy said she would have no trouble sleeping through the noise and soon crashed.
She didn’t wake up until after eleven the following morning. The sun had already been baking the island, but the ever-present breeze helped keep it reasonable. When I heard her stir, I went out and picked up a couple of cappuccinos and sweet rolls at one of the coffee shops near the quay. We sat in the cockpit drinking our coffee and watching the people walk by. The people were watching us watching them. We talked about boats, and she obviously had read up on the subject even if she had no experience. She said that she would want to be able to handle this boat at the end of our week. I said that that would be no problem.
She was obviously not used to roughing it in warm climates. The boat outfits that I had suggested; shorts, simple tops and bathing suits, were not part of her North Dakota wardrobe. She said that she had had to spend some time shopping and she hoped her outfits were appropriate. I said, “Mandy, whatever you decide to wear is appropriate – just be sure that whatever you wear on your feet has rubber soles. Better yet, go barefoot.”
Some women can make an expression that says "Wait till you see what’s next." Mandy did just that - or at least that’s what I read into her sort of smirk.
We drove around the island of the Greek mathematician Pythagoras. When we got back to the main town, I bought her a Pythagoras t-shirt with a graphic of his theory, you remember: a2 + b2 = c2. She seemed happy. She was definitely not a t-shirt girl, more a Gucci woman. I like t-shirt girls, but paying guest Gucci women are even better. We had dinner at one of the tavernas. I never cook dinner for guests, they live longer that way. She was a great conversationalist and I enjoyed her company and she, I thought, mine.
She told me about her life, how she and Bob had been married for five years. He was a patent attorney and she was now a middle manager in a pharmaceutical firm. She had started in the marketing department as a cost accountant and, after getting her MBA, rose rapidly in the ranks. She and Bob had met at work when her company was seeking a patent on a new product. They had a nice house in the suburbs; he played golf every weekend; she played tennis, and they both regularly visited a health club. So exactly the kind of life I was escaping from. When the subject turned to children - neither she nor I have any - she seemed to close up and I sensed that it was a taboo subject. She and Bob had decided that they needed some time totally away from the everyday and one of her girlfriends had suggested a cruise. She told me that her friend, who had done a charter with me a few years back and had very much enjoyed it, had suggested me. She named my benefactors and I remembered having had them aboard. I made a mental note to send them a thank-you note. The best references are word of mouth.
The following day we left the lovely port of Pythagorion for an anchorage on the south side of the island of Agathonisi. The Meltemi had picked up and it would be a pretty boisterous downwind run. This first day would be the hardest; after that, short hops with relatively calm seas. She said that she was ready for a new experience, that she had regretted asking for calm conditions. I told her that I’d sort of lied, but downwind should be okay for her. And this was a great sea boat. She said she had read up on my boat, and that had helped convince her that it would be okay.
It was around eighteen miles and I figured we’d do it in less than three hours. Hopefully if she had a tendency to mal-de-mer, it would take a while to develop. I told her that the first thing she would need to do is learn to steer the boat. She hand-steered for the first hour. I always ask any crew that are a seasickness risk to steer the boat. It requires the person to look at the horizon and keeps their mind focused on something other than how miserable they feel. I was taking no chances with Mandy. I carry seasickness pills, but they either do nothing or make the person so drowsy that they have no clue of what’s going on.
Mandy was a bit intimidated at first. Comfortably Numb is a relatively light forty-four foot sailboat, but with the big genoa pulling and the rushing of the big seas breaking at the stern, it can get intimidating. She was determined to do well, and after a while seemed to enjoy how the boat surfed on the big overtaking seas.
We made the island by 1400, before the stronger afternoon winds came up. We motored into the SE anchorage. We were the only boat – no surprise.
I dropped the anchor in eight meters of water over a sandy bottom in the small cove of Palos and shut everything down after the anchor was securely set.
“Do people here sunbathe topless?” Mandy asked from inside the boat.
“People on my boat do whatever they want. Do you see an audience?” I replied, hoping she wouldn’t name me.
She came up the companionway stark naked. My brain and heart stalled momentarily. Part of me is still in my prepubescence; I stare at breasts. Just can’t help it. I did also notice that except for the bikini wax, her bush was ample. I prefer a bald pussy, but it is what it is. I didn’t expect to see any tattoos or piercings and there were none. I’m fine with small discreet tattoos, I think big in-your-face tattoos are tacky. Piercings, other than earlobes, are a major turnoff. I cannot understand why a person would do that, especially in sensitive areas. Makes me cringe. Probably my old age.
“Okay, what are you looking at?” she sounded a bit self conscious. I mentally gave myself a firm kick in the butt.
“At the loveliest sight on this boat in a long time,” I tried to make up for the brain-stall.
“Bullshit, Fred, but I like it anyway. I am not used to walking around in my altogether, so you have to act a little more nonchalantly. In fact, I have a better idea.”
“What will your husband say if you came home with an all-over tan?”
“He’s expecting it.”
“You’re joking? He expects you to be naked with a very untrustworthy older person of the male persuasion?”
“Of course not, silly. He has no idea I’m here.”
“Uh... Bob doesn’t know you’re with me?”
“Not a clue. I said I was going to a sun, fun and fitness luxury spa in Arizona.”
“What if he tries to call you?”
“My phone works here, I have an all-band smart phone. But I told him not to call me, that I would call him. It’s nine hours later here than in Bismark and that might lead to middle of the night calls if he called after work,” she said confidently.
“Is there more to this story?” I asked.
“There is.”
“Are you going to tell me?”
“Eventually. Maybe,” she said.
“Wow!” Sometimes I get very articulate.
“Stop changing the subject, I told you I had a better idea,” she said.
I love a mystery. “And that would be?” I asked.
She said, “Give me one reason why I should be the only one sans clothes?”
“Cause you’re a married woman and I’m a lecherous old man who might try to take advantage of a scared, vulnerable woman.”
“So far no reason. I don’t see any scared or vulnerable women. The lecherous bit’s not bad. Work on that,” she smiled and stretched out on a beach towel, adding, “I’ll look the other way, I’m sure you’re a modest man.”
She had, until then, given me no reason to doubt her honorable intentions; no fuck-me pumps, no high exposure clothing, no solicitous ‘accidental’ contact, no talk about sex. But of course the naked appearance had an almost immediate effect, and now the evidence was, uh, mounting.
I took my t-shirt off. She looked amused.
“Hesitation is for cowards, keep going.”
I pulled my shorts down. Surprise! A hard-on.
She said, "Thank you!”
“For what?”
“For sporting that serious woody; I started to think you didn’t like me.”
“Mandy, you hired me to take you on a cruise. You are obviously a woman of class - and don’t you think it would be inappropriate and highly presumptuous of me to act as anything but your guide? And yes, I find you very desirable.”
“You really are a bullshit artist. I have an MBA just like you. I have a responsible job at a Fortune 500 company where there are over fifty names under mine on the organization chart. Do you really think that I can’t take care of myself?”
“So, Mandy, what’s on your mind?”
“I think we should do something about that condition of yours. I couldn’t relax in the sun while you were stressed.”
She came over and straddled my lap. Her firm breasts, pointed at my chest, demanded attention. I cupped each and gently squeezed. She purred softly and kissed me tenderly. “Much better,” she said.
Her hands grabbed my balls and played with them. I kissed her nipples. They were nice and hard now. I flicked my tongue over each.
She got up and reversed her position. Her back was to me. I reached around her and pulled her to me by her breasts. I can’t resist squeezable breasts and firm nipples. She now reached for my cock and rubbed it against her pussy. She wet her finger and rubbed in on the bottom of the head of my cock. Then she pushed her pussy lips apart with my cock and rubbed it back and forth against her opening, slowly and methodically. I made some encouraging sounds.
“What do you think so far?” she asked.
“I think I am about to fuck a beautiful woman.”
“That’s a roger, Captain Fred,” she joked and gave my pole a few strokes.
Somewhere in the windup to the good part of the excitement, I bring up the issue of safe sex. The era of fear of communicable diseases seems to have passed, at least among the ladies that it has been my pleasure to be intimate with, but I still offer to use a condom though I admittedly find the things revolting. I mean, how do you gracefully switch from a mind-shattering blow job to a deliciously titillating fuck if you have to stop and reload? It just dampens the mood.
Mandy had laughed when I brought up the subject, said she knew all about me and that she wasn’t a teenager any more, so that I shouldn’t even think about it. I didn’t really understand either of her reasons, but since she had given the right answer I didn’t dwell on it any more.
She leaned back and said, "Lie down.”
I lay on the settee; she was still straddling my waist facing away from me. She slid back so her pussy was over my face and she leaned forward and slowly slid her lips over my dick, flicking her tongue all the while until she had the whole thing down her throat. I was mesmerized.
She made a loud moan that I correctly interpreted as an invitation to make a contribution to the procedures. I reached forward and squeezed her breasts and my tongue started to lick around her pussy. Then I buried my face in her muff and got as deep as I could into her sopping pussy. She was slowly moving up and down on my cock, and I would move my hips up as if to get her to take in more. I gently sucked and licked her clit, then licked the edges of her pussy. I seem to meet prodigiously flowing women; the seat cushions once again would require serious cleaning.
I wasn’t going to last too long, especially since this was the first time with Mandy. She sensed that I was near my threshold. She got up, turned around and lowered herself onto my cock. I instinctively thrust up, but in this position she controlled the action and she was clearly not ready for me to cum. She slowly ground her warm cunt around on my dick, not letting me move up and down.
I reached up and squeezed her beautiful breasts and rolled her nipples between my fingers. She liked that, and I continued working on her nipples. Meanwhile she kept moving her very warm pussy sideways and back and forth, causing friction on her clit. She leaned forward and lay on top of me.
“Time for the last act, dear Fred,” she whispered and rolled over. In a relatively small boat it requires a certain amount of athleticism, but she got me on top of her.
“My pussy is craving for some deep company. Why don’t you put that big thing of yours in and let’s relieve some tension. I haven’t been fucked really well in a long, long time. I want to feel your cum heating me up deep inside.”
I easily slid into her very slippery pussy and slowly moved in and out. She reached forward and rubbed her clit.
“Go slowly, Fred. Make that cock a piston, slide up and down. Can you feel my pussy squeezing your cock? I guess you can.” I had moaned when she contracted her cunt and increased the pressure on my rapidly dwindling will power. She kept squeezing. I couldn’t figure out how she could do that. I had never met a woman who could apply so much power.
“Are you close yet?” she asked.
I grunted. Sometimes words are elusive.
She sucked my earlobe and whispered in my ear, “I’m almost there, I want you to try to cum just after I do. Shoot your spunk into me. Deep. Deep and warm,” she whispered in a low, seductive voice. The seduction part was, of course, long past necessary.
“You’d better cum now, Mandy. Cum for me, cum now,” I said, increasing my thrusts as I started to lose control.
She issued a deep moan, then a louder moan and started to move her hips rapidly.
“Ohhhh, here it comes. Hold it as long as you can, Fred. Ohh.. fuck me harder, fuck me. I love that cock of yours.”
I shuddered trying to hold back as I wanted her to climax as long as possible. Her voice kept going up and I knew she hadn’t peaked yet. She grabbed my ass and pulled me against her, heaving her hips. My cock was totally buried into her deliciously hot pussy. I couldn’t hold it any longer and I felt my balls contracting as my cum flowed deep inside her. She could feel my climax and got off with me. Cumming with your partner is definitely one of life’s finer moments.
“Move slowly, Mandy, and squeeze my cock, draw all my juice,” I moaned.
“Keep moving at whatever speed you can that feels good. I’d love to be fucked for a while longer. This is just sooo good.”
She stroked my hair and put her tongue in my ear while whispering sweet nothings. She reached down and very gently played with my balls, saying how good they felt and how much she loved being with me. I held her tight.
We eventually got up and went for a swim. This bay has crystal clear water and you can see the bottom clearly. I snorkeled over the anchor to be sure it was well set in a patch of sand and we enjoyed a drink as the sun lowered over the cliffs in the west.
The island’s main (and only) town has a restaurant that makes a renowned fish soup that you have to order in the morning. Mama then goes to the fisherman, buys what she needs and in the evening there’s a meal that’s worth the journey. I had called before we left Samos and our table would be waiting at 1900. Its a two-and-a-half mile dinghy ride around the point to the main harbor. My dinghy has a fifteen-hp outboard and, when conditions are calm as they were now, it would take less than ten minutes and we would stay mostly dry.
Mandy went down to change and came back up in a stunning tie-dyed light dress that showed a lot of cleavage and, as she was not wearing a bra, silhouetted her hard nipples. “Nice dress!” I said, “Maybe we should take a few minutes before we leave to...”
“What kind of girl do you think I am?” she laughed.
