Sweet Escape Ch. 01

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Captain Dev finds her top crew ready.
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Part 1 of the 3 part series

Updated 09/22/2022
Created 04/18/2008
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Chapter 1: The Best Crew

"Let's head south."

That's what I told him.

We were finally ready! Really ready. The boat was re-fitted to within an inch of its life. Now it would take us safely, (we hoped!) anywhere we chose to go. And being the "Admiral", I chose south. I wanted to head back to the San Blas Islands of Panama. We both wanted to go back to those picture-perfect white sand beaches and palm-tree farmed islands. I was thrilled that this time we would be on the "perfect" boat; a nice-sized catamaran. Not too big, but big enough to take crew or family/friends along when we so desired. We had some fairly long passages ahead of us and I was thinking about that very question: Who to take as crew?

I'll admit here that I've had a long-running fantasy of having that "special boat boy" for a crew member, ever since I started cruising over nine years ago. Now that I've just turned 50, that fantasy is about to become a reality. Of course it would depend on who is available. My first choice would be Alex, of course! We've been fantasizing about doing a voyage together for a very long time. Timing has always been the issue. So I promised him that when we got the next boat, we'd take him along on a passage or two. Also, he's one of my favorite lovers, going on some 20 years now!

Second choice would be one of other guys who I've come to know more intimately and who also sail. That's the prerequisite, you see; they have to do both! So it's time to put out the word that I'm looking for that very special crewmate. Time to write up a clever email to send to these guys, tell them how fabulous the trip will be and how much fun they will have.

There's just one little problem: my partner. How do I tell him? "Hey hon, remember how I said I wanted a boat boy? Well, do you mind if I fuck 'em?" "It would make the passages go so much better for me, ya know?" It's either that, or you go with a hired crew and I'll fly!" I wonder how he's respond to that. I have to tell him. Boats are very small spaces to live together in. You'd be hard pressed to keep something like that under wraps on a boat!

Well, we'd have to cross that bridge when we come right up on it. And let's hope I get all the leeway I need. In the meantime, I needed to pick my crew.

As it turned out, Alex and Jon were available and willing. I gave them the schedule of when we hoped to shove off from Miami, they would meet us before we sailed by at least a couple of days, so that we could deal with last minute provisioning and those details that always seem to creep up just as you're ready to split. I couldn't wait! I hoped that my mate would be busy with last minute work, so that I could get reacquainted with Alex and get to know Jon a bit, maybe all together!

The day finally arrived: Alex showed up first, knocking on the hull early Wednesday morning.

"Heeeelllooooo! Anybody onboard?" he yelled loud enough for all to hear.

I yelled back from the salon, "Come aboard!" It was great to see his smiling face again after more than a year.

"It's good to see you, Dev," he said as he threw his arms around me.

We hugged our usual long-ass hug and then pulled back to stare at each other. He looked pretty much the same. His blond hair, longer now then when I last laid eyes on him, gleamed in the morning sun. I leaned in to kiss him. Some things never change! He always wants me to make the first move. He kissed back and seemed to melt into me. It had been a long time! My hands grasped his face and then caressed his silky hair.

Man! I'd missed running my hands threw his fine hair. My mind jumped immediately back to the day that met. He was so awkward, looking like a total fool dancing at the empty club in Marin. But I was already sucked in but his quirky humor, naïveté and odd sense of being in the world. Another "Stranger in a Strange Land," like me! He was so inexperienced back then, but oh, so willing to learn. I told him to grab his bag and stow it in the starboard aft cabin. He obliged and I offered him a drink. It was November already but it was still hot in Fort Lauderdale. We were both starting to sweat. I poured him a cold tea and we sat at the salon table and caught up a bit.

It wasn't too long before we were touching again. We were always very hands-on, ever since we met almost 15 years ago. The next thing I new, my hand was stroking his growing erection. He smiled and kissed me before unfastening his shorts to lose his long cock and let it unfold. It was just as lovely as I remembered and I leaned down to give it a lick. He moaned loudly and lay back on the setee.

"Ah! You haven't forgotten how that feels, eh?" I whispered.

He moaned his answer and said, "I could really use a good fuck."

"Ok!" I replied as I took him by his hard-on and led him into the aft cabin, in case my mate should come back early.

We stripped completely taking each other's clothes off slowly while licking and kissing each other all over. He sat me on the bed and stuck his cock in my face.

We both seemed to recall the last time he came that way, something he doesn't experience very often, as he tells it. We were in my old apartment and he was visiting us for a couple of weeks while looking for a boat to buy. My mate was in the other room, dozing in front of the TV. Alex had just come back from a "date" and was horny as usual. My libido was in overdrive since he had arrived. We were fucking morning and night and sometimes a quickie in between. I was sitting at my desk playing on the computer and he was standing next to my chair. I swung around and was face-to-cock! I started to suck him and decided to go for it. I knew that it was hard for him to cum this way, so I gave it my all, slurping and sucking and using my hands. I griped his tool right at the base while I fingered his asshole. He loved that and I knew it would make him cum sooner, hoping that I wouldn't hurt my lips before that. It took what seemed like twenty minutes, the longest head I've ever given, but finally he came and squirted his creamy load down my throat. It was pretty exciting and tricky as I kept looking at the space between the door and the hall to see if my partner would walk in on us! (He never did!)

Now we were finally poised to do the cruise that we'd talked about doing for all these years, and it made sense to the start with a nice blow-job. I took his long, lean cock in hand and began sucking it for all it was worth. He loved it!

"God, that feels great!" he moaned.

I could only hum my reply and that made him moan even more. I sucked him for a few minutes and then came up to tell him what I wanted.

"This time, I want you to lean me over the bed and fuck me fast and hard for a while. Later, I want you to fuck me on deck and on the tramp. That should be fun!"

I turned over and reached for the floor. He really loves that! He reached his hand down between my legs and parted my lips, inserting a finger to feel how wet I was. Then he guided his cock into that hotness.

"Oh yeah! That's it baby, slide it in nice and slow, then slam it!" I told him.

He let out a long gasp as he slid his cock all the way inside me. He fit so well and he always loves that first entrance, how it feels to be engulfed inside my hot cunt. It gave me that tingly-butterfly feeling in my womb, the one I always get when I reflect on an especially erotic moment.

And, the way he sucks in that breath as he enters me... I love it! Once he was deep inside me, he pulled out almost all the way, and then thrust back in fast, repeating that slow, then-fast, motion until I changed the rhythm by backing onto him as he leaned in. We picked up the pace, me leading the rhythm for another 15 minutes or so.

Now Alex can fuck longer than anyone I knew. He has a real talent for not cumming until he's told to. I've always appreciated that about him. But worried that my mate would be back anytime, I encouraged him, fucking him fast and furious for another 15 minutes before telling him that I wanted to feel his hot cum fill me up. He immediately changed the pace and the motion, slowing down and grinding his cock into me before withdrawing it until it was almost out, before sliding back in, nice and slow. I was getting pretty damn hot now and I reached around for his hand and directed it to my clit. He started rubbing and it felt fantastic.

It was so hot to have his hard cock inside me, squeezing it as he rubbed my clit. He brought me to orgasm in minutes and knew that I wanted him to cum with me. As I cried out with the release, he pumped his cock a few fast thrusts and stopped to feel my contractions while he let go a thick load into me.

"Wow! Nice fuck, sweetie! It's good to see you again too!" I told him.

We laughed, enjoying being together again and collapsed together onto the bed.

Thank goodness we had another half hour to hang out before my first mate returned from errands. I called him on his cell and reminded him to pick up the mail on his way back to the boat (and to get his ETA!) and Alex and I lay side-by-side discussing the upcoming voyage. We were headed for the tropics and both enjoyed what came with that; little or no clothes, lots of time in the water and as much beach time as we could get. Not to mention, all the sex we could fit in. Not a bad way to go!

Then Jon showed up on the scene and on my screen, (he found me online and I'm still not certain how. Perhaps someone forwarded my crew search email to him). It was to be a fortunate set of circumstances that he came to sail with me on my sailing fantasy.

I'll let Jon's tell his story...

"I'm on my way down to the City Marina in Fort Lauderdale to set off on a sailing adventure from Florida to the beautiful blue waters of the Caribbean. Excitement overcomes me as my cab pulls up to the marina and my new captain and guide (a beautiful 49 year-old women, is waiting to meet me. I follow her careful directions and locate the large cat on the end of dock 'C'.

I call out "Anyone on board?"

Dev yells a greeting out from below deck and invites me aboard the boat. She explains that we're just about to loose the dock lines and that I should stow my stuff in the salon for the moment and be on the bow ready to receive a line. I follow her lead and toss my two bags below before running up to the front of the boat. Another crewmate is on the dock now, getting ready to untie the lines.

As we are getting ready to set off Dev, a very experienced woman of the seas, explains that she has an exciting trip planned for us. Dressed very nautically in a classy dress shirt, Khaki shorts and a captains' visor, Dev carefully instructs me how to cast off as she guides our boat out the inlet. A rush of excitement overcomes me as I watch this women set the sails. We motor-sail out Port Everglades and into the Atlantic and the Gulfstream. I have no idea what to expect for the rest of the trip. I just know that it will be good. Our initial chats online have been very hot.

As we glide through the Atlantic I watch as flying fish hit us with the ocean spray.

After introductions, Dev shows me to my cabin in one of the 'amas.' I am impressed with the boat and tell her how excited I am to be accepted as crew. She tells me that I still have a few tests that I must pass in order to become a full crewmate. Then Dev unbuttons her top and takes it off and lets her beautiful breasts hang out and slips out of her shorts. Standing there topless in just a black thong like the goddess of the ocean, riding the four-foot swells, she explains she loves to sail in the nude.

As I sit there and admire her curves, she asks me if I would oil her body up with suntan lotion and advises that she should do the same to me in return. Now I'm getting very excited and pretty horny too. I start rubbing her with the oil, starting on her back, rubbing it down to her ass, then on to her legs and thighs. At this point my cock is throbbing as it's rock solid and it's now very noticeable, all 7 1/2 inches of it. She notices too and she tells me to take my shorts off. I jump out of my shorts and shirt and since I'm not wearing any underwear, I am standing there butt-naked with my cock and balls feeling the ocean breeze blow through the open ports. She turns around and starts oiling my body while at the same times begins caressing my balls and tells me I'm in for the trip of a lifetime, and she adds that she thinks I'm hot!

She makes me feel instantly comfortable and to show her how much I like her, I start kissing her lower back and slide off her g-string, gently kissing and breathing in her scent very lightly. Continuing around her thighs, I work my way down to her hot pussy, gently blowing and kissing on her clit. I slide a finger inside her hotness and notice that she is already really wet. Then she runs her hand through my hair.

As we glide along with warm gulfstream spray on deck, she pushes my face into her pussy and I eat her out and run my tongue gently along her curvy hip and ass doing whatever she desires.

Now it's her turn as she starts kissing me then moves to my nipples and works her way to my balls where she slides her tongue from my balls up to the tip of my cock! Wow! I'm already ready to pop! Then she grasps my rock solid cock and puts it into her mouth with her juicy lips sealing it as I slide my fingers through her beautiful hair. Her tongue moves back and forth along my erection as I look across at the big blue ocean.

After a half an hour of the best blow job ever, she made my cock explode and took it all down her throat as she gripped my balls and I pushed every last drop out. She is ready to have me inside of her, so she pulls me over to the bunk and lays down on her back, spreading her legs wide and runs her finger over her clit while her other hand rubs one hard nipple. I straddle her and she reaches to stroke my cock, getting me ready. I take things into my own hand and start slapping my cock all over her pussy and put the tip just inside teasing her hot pussy until she can't take it anymore and she grabs my ass and pulls me inside.

I pump my hips back and forth, slowly in and out of her wet cunt until things start getting a little more wild, I notice we've started pounding into the waves as I'm pounding her pussy, my hands griping her ass cheeks. She moans and pants, but we can still hear the sound of my balls smacking against her ass and it echoes in the cabin. After a half hour of fucking her from the front she stands up and bends over and grabs the bunk rail as I rub my hard throbbing cock on her ass and then put it back in her pussy. She works my cock and while her ass smacks back and fourth on me, I pound her beautiful pussy from the back, all the while my finger is rubbing her clit.

Soon she is urging me on, "Fuck me harder!"

Telling me that she's about to cum, she wants me to cum inside her.

"Let me feel your hot load fill me up, baby!" she moans.

I'm ready to unload. My balls are tight and full and the feeling of them slapping on her ass is making me crazy. I encourage her now,

"Come on, Captain! Cum for me!"

I tell her I'm her "special" boat boy and I aim to please. She likes the sound of that and the next thing I know, she is writhing, panting hard and she has reached her hand between her legs and is grabbing my balls and squeezing them. Wow! They are definitely ready to unload. I pound her good for another minute and we both release simultaneously.

"Ah, AH, AHHHH," she is almost screaming now.

I wonder what the rest of the crew are thinking, as I pump my thick cum into her hot cunt. She squeezes me until every drop is out and then falls forward on the bunk, taking me with her. I land on her back and we lay that way, panting and letting our heart rates lower a bit.

Turning me over, she rises up on an elbow and looks into my eyes.

"You're going to be a very important part of this crew, ya know?"

"Oh yeah," I respond. "Yes, I can already tell!"

She laughs and jumps up.

"Now I've got a shit-load of things to do and your needed on deck, so hop to it, my hot boat boy, time to get serious!"

(Jon's story is far from over, but I'll get back to it later on.)

We both throw on our clothes and head for the salon. Fortunately, the rest of the crew is in the cockpit sailing the boat and enjoying the afternoon sun. We come through the wide sliding glass doors and I announce,

"I've just finished giving Jon the orientation. He seems to be catching on quite well. I hope everyone will welcome as our newest crewmate and be available to assist him as needed. He's not a very experienced sailor, as the rest of you are, but he makes up for that in many ways."

I watch as Jon begins to get acquainted with everyone. They seem to like his rugged good looks and his easy manner. I like the thought of seeing his hard cock everyday! Something tells me that this next passage will be a dream.

Much to my surprise, I find my first mate and partner, 'T' is watching me with a slightly amused look on his face. I think he is finally catching on and I give him a sideways glance indicating that he should give up the helm to Alex and come down below. I have to keep the entire crew happy or things will not go smoothly.

He picks up on my signal and yells over to Alex,

"Hey pretty boy! Take the wheel for a while. Make sure you keep this heading and don't forget to check the GPS track. We've got some very shallow water around here and I don't want to get into any. Capeesh?"

Alex jumps up and salutes and takes over the helm.

"T" follows me down below and watches me while I grab a cold bottle of beer out of the frig. I open it, take a long swig and hand it to him. He does the same and follows me into the forward port cabin.

"This is going to be fabulous cruise!" I offer. "I bet it will be one that we won't soon forget. Now, as of today, we're starting a new routine. We've got a good, skilled crew that we can depend on. So from now on, when we get underway, you and I are going to find a private spot and have some fun. Ok?"

He nods, not sure what he has just agreed to, but liking it non-the-less.

"Come over here and take your shorts off, please!" He complies, but then decides to sip on his beer some more.

"Why don't you take them off?" He says.

I smile and reach over to undo his button and slide his zipper down. I reach in and give his bulge a squeeze. It begins to respond and grows immediately, unfolding and springing out of his shorts. I kneel down in front of him and take his growing hardon into my hand, running my tongue over the tip and down the head, just like he likes.

"MMMMMM!"

After a couple of minutes of sucking and licking him, I reach my other hand between his legs and tickle his balls. He loves this. Then I run my finger up the crack of his ass and he squirms with excitement. I know it won't be long now before he squirts his load down my throat. I increase my grip on his tool and jerk him while I play with his asshole and grab his balls.

"Ohhhmygod! I'm gonna cum," he blurts out as I flick my tongue over the head of his cock.

Then I take him all the way into the back of my throat and he releases his load of hot salty cream. I lick up the dribbles and wipe my mouth on my arm. Coming up, I kiss him on the mouth and tell him to relax and enjoy himself.

"Hey, later if you want, we can teach the rest of the crew how to do a massage circle. Might as well start them off right, eh?" I tell him.

On this, our first ocean passage on our new boat, we have four crew members along. Alex is my oldest friend; an ex-boyfriend, occasional lover and excellent sailor. Except for the fact that he can't fix anything and he eats like a horse! Alex has brought along a new friend of his. Her name is Sarah.

According to Alex, they met on one of his treks across SE Asia. Thailand, I think. They didn't hook up until recently, when she contacted him via email and asked him if he wanted to do a trip with her. Now Alex has been looking for a woman to travel with for many years. We never got to do it for one reason or another. Our timing was always off. But he told me about her interest and I suggested that they start their journey on Sweet Escape. It would be romantic and easier than biking across a country. He was keen to go and he asked her. As it turned out, she had some sailing experience and was more than thrilled to be asked aboard.

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