Aye Aye, Captain Jack!

"Uh, Clara, it's getting late, and we got a long day ahead. I'd like to get a ways into the Italian coast."

"Aye aye, Captain Jack."

Damn, why did I say that? Did I chicken out?

After cleaning up from dinner and putting the leftovers in the fridge, we bid goodnight and I close the door to my cabin behind me. And let out a big breath. I'm still raging hard with thoughts of what I want to do with Clara, what I want her to do to me. I climb into bed and start rubbing my erection. I want her so badly. How far is she willing to take this? How far am I willing to push my luck? I've got to finish myself off tonight if I want to get any sleep. Glad there's a supply of Kleenex in here. As I stroke myself, it's Clara's hand doing the work. Those soft, delicate fingers, sliding my loose foreskin up and down. I'm about to cum and she lowers her lips onto the head. Looking up at me with those big, longing eyes, I can't hold back. Oh God. I'm squirting into the Kleenex, but it's really her mouth. I keep, I mean, Clara keeps stroking through the duration of my climax. She takes it all in a single mouthful, and then tilts her head back and seductively swallows. A few more strokes and a residual drop of cum forms at the tip. She scoops it up on a finger and offers it to me. I suck it off of my finger, but it's really her finger. I fold up the Kleenex and throw it away.

--- Day 3 ---

Jack:

The next morning, ready to cast off. Clara starts the engine, but I say let's just sail off the mooring. We've got plenty of room. Clara kills the engine, while I raise the sails. I backwind the jib to port to push the bow to starboard, then quickly sheet it in on the starboard side and we're moving. When the anchor is directly abeam on our port, I tell Clara to come about and head for the anchor while I switch the jib to port again. As we approach, I'm at the bow quickly pulling the anchor line on board. Over the anchor, I holler to Clara to hold the heading for now. The anchor lifts easily and I store it in the forward hatch before returning to Clara in the cockpit.

"We make a pretty good team!" Clara exclaims.

"I only hire the best."

"Maybe I should ask for a raise."

We tack a few more times until we're clear of the mouth of the bay and the peninsula that is Saint-Jean-Cap-Ferrat, then I tell Clara to point us north-east and I let out the sails for a beam reach up the coast.

Clara:

That was fun, sailing off the mooring like that. We're now headed up the coast toward Italy. Jack said I'm doing such a good job I can just stay at the wheel.

"There's Monaco," Jack point out.

"Take the wheel," and I dive below deck to grab some binoculars. Back in the cockpit, I start scanning the mega yachts.

"Find your prince?" Jack asks.

"Nah."

"Maybe it's too early for the leisure class to be out of bed."

"I'll just have to settle for you, you old fart."

"That's no way to talk to your elders. Maybe you should learn some manners."

"Maybe you should spank me!"

"Don't tempt me."

We're making great time today. The water's flat, and as the coast has bent to the north, the actual wind is slightly astern of starboard. But with our speed, the apparent wind is directly to starboard, so we're still on a beam reach and just flying through the water. Sailing at its best!

Jack's turn to make lunch. More fruit, vegies, bread and cheese. We take turns trying to toss grapes into each other mouths. We're not very good.

Jack:

"There aren't many good anchorages along here," I tell Clara, "and we may have to put in for the night at a marina. But there's a little island off Albenga called Isola Gallinara. The north side may be out of the wind and a good spot to anchor."

The island comes into view. We approach and go around the west side. And just as I thought, calm water on the north, very little wind, perfect.

"Very private," Clara notes. "I like this."

After anchoring, "Can I have your passport?" Clara looks puzzled. "We've 'landed' in a new country. I've got to declare us in to Italian Customs. She digs out her passport, hands it to me. I head for the radio, while Clara strips down again and jumps in the water.

Customs formalities done, I'm back on deck, Clara hollers for me to join her. Ah, what the hell? I strip down, jump in, and swim over in her general direction. We splash around and dunk each other like a couple of kids. Worn out and unwound, we head back for the boat. She's first out of the water, claiming the first shower. Fine with me as I get to watch her glorious ass climbing up the ladder. I follow, but by the time I'm back on board she's modestly covered herself with a towel and is ducking into the salon, bound for the head.

Clara:

Finally got him out of his clothes, if this really counts. His chest is as hairy as his arms and legs. Can't see much of his cock in the water, though. However, back on the boat, I steal a glance has he coming back on board. Not much of a shower; sure hope he's a grower.

After I shower, and Jack goes in for his, I set about prepping dinner. Simple pasta with olive oil, and a hefty amount of garlic and oregano, both rumored aphrodisiacs.

Suddenly, Jack is behind me. "Smells like heaven," he says.

"Me or the pasta?"

"Both."

And I push my ass back aiming for his groin. Except I only hit his thighs because he's so much taller than me.

Again, we settle into the cockpit for another amazing dinner. And another bottle of wine.

We have the sun later tonight as we're about mile off the mainland so little to block it. No cold excuse tonight for moving in close to Jack, but that doesn't stop me.

Jack:

Wow, that dinner was amazing. Strong garlic and oregano. Winding down, Clara scoots over close to me once more. Can't be that cold; we still have some sunlight and it's quite pleasant. But she's resting her head on my shoulder, and after a gulp of her wine, she sets the glass down and puts her hand on my chest.

OK, the kitten has definitely come to me.

I put my hand on hers that's on my chest, sliding my thumb under her palm, and pull it up to my face to nuzzle her knuckles. She turns her head toward me, watching with keen interest. No turning back now. I release her hand and push some of her hair back over one ear. Then I trace my fingers down her jawline to her chin, which I pinch between my thumb and forefinger, lifting her head up to mine. I graze my thumb across her lips. No resistance.

I tilt her head a little more upward and lean in. She slowly closes her eyes, and I can feel her breath on my lips. Ever so slowly, I lean in and lightly touch my lips to hers, just for a moment, then pull back. Her eyes still closed, she licks her lips.

The hand that was on my chest is now reaching up behind my neck to pull our lips together again. Longer this time. We back away just slightly, and I tug on her bottom lip with my lips. Her eyes still closed, she pulls us in again, this time more forcefully, mashing her mouth against mine, and she sliding her tongue in between my lips, which I welcomingly suck into my mouth. Her tongue retreats, but mine pursues it into her mouth.

Clara turns her whole body more toward mine and throws one leg over mine, sliding onto my lap, straddling my legs, her knees on the seat near my hips. She has both hands holding my face as she further ravishes my mouth. I'm sliding my hands down her back, and by the time I reach her ass, she's lightly moaning.

We back off the kiss, but our noses are still touching. We are both breathing more heavily but not saying a word.

Clara:

I thought he'd never come around. But that kiss. Taken dominantly, but performed delicately. I'm melting.

I want more of that. I reach up behind his neck and pull us back together. Lips locked, I climb onto Jack's lap, straddling his thighs. Due to our difference in size, we are eye to eye. Perfect.

Lips still locked, his hands are now sliding down my back. Oh, please squeeze my ass. Yes. Yes!

We finally break the kiss. And now his hands are coming up my sides, under my shirt. So glad I left the bra off. His thumbs are at the sides of my breasts. Please, Jack. Touch them!

But no, his hands are retreating! Wait, he's got the bottom of my shirt and is pulling it up. Oh goody! I lift my arms so he can remove it, and my tits fall from the fabric.

"Do you like my girls, Jack?"

"Oh, Clara. You have a lovely family."

Jack:

After squeezing her ass, I slide my hands up Clara's sides, under her shirt. My thumbs feel her boobs and the feel massive. I gotta see them. I pull my hands back to her waist and start pulling her shirt up. She raises her arms to allow me and her boobs drop with a luscious bounce. They may not be the biggest I've ever seen, but certainly the biggest I've personally beheld.

"Do you like my girls, Jack?"

"Oh, Clara. You have a lovely family."

Clara now rises up on her knees, which brings her body closer to mine and her incredible boobs right in front of my face. I reach up and cup them from underneath as if to gauge their weight. And they are heavy, but their shape is amazing. Standing firm and proud. Plump, pink areolas that puff out slightly. And a pair of darker, succulent nipples. I start massaging them, caressing them, loving them, and she purrs, more truth to that kitten analogy. She leans closer and I'm nuzzling in mounds of soft mammary flesh. I'm now rolling her nipples between thumbs and forefingers. But, oh, but I've got to have my lips on them. I need to suck them into my mouth.

I bring my lips to one of them. At first, I just pinch and roll it between my lips. Then I suck the nipple, the areola, and a little more into my mouth and swirl my tongue around the nipple.

"Oh, Jack, that feels so good. But please, the other one, too." I can only oblige.

After suckling on Clara's nipples for a while, she sits back down on my lap. Oh please, don't take those boobs away from me. But she leans in for another kiss. Lingering, she slowly slides the rest of her body backward, off my knees, and breaking the kiss but not the eye contact, and descending to the floor of the cockpit.

She now has her hands on each side of one of my legs, and they are sliding up inside my shorts. The one on the inside of my thigh reaches my dick, she finds it hard and throbbing.

"A grower!" She smiles.

"A what, sweetie?"

"Nothing Jack. Just a private little affirmation."

She pulls her hands out and grasping the elastic waist band of my shorts, starts pulling them down along with my briefs. I lift my butt for her and she slides them off of my legs. My dick springs up in front of her face. She stares for a moment, then mouths, "Oh my god."

Clara:

"A grower!"

"A what, sweetie?"

"Nothing Jack, just a private little affirmation."

With both hands, I pull down the waist of his shorts, along with his briefs. He lifts his ass to cooperate. Halfway to his knees, his cock springs skyward. Oh my. It's not the biggest but plenty big enough for me. But the shape. The top half of his shaft is the thickest, and it tapers in slightly toward the base. I like 'em like that. Nothing like getting stretched both sliding in and sliding out. He's cut, and the groove beneath the crown is deep and wide. More vaginal stimulation. And the veins. Like on his arms. "Oh my god," I sigh.

Above the groove, the head is the same diameter as the upper shaft. But it's bulbous, and purple, and taut like a balloon about to pop. There's already a little drop of pre-cum at the tip.

"Been thinking about me all day, haven't you Jack?"

"Sorry?"

"You're already juiced up!"

The whole display looks angry. And beautiful at the same time. It's magnificent. I wrap my fingers around the thickest part, and I can barely touch my fingers to my thumb. Gripping it like that, there must be at least an inch and a half still exposed above and below my hand. I give it a couple of gentle strokes up and down, and Jack's head falls back, looking at the sky.

I push it down so it's aiming at his face. Licking the palm of my other hand, I start sliding that hand up and down the length. Damn, but it's longer than my whole hand! Jack lifts his head and moans, and lets it fall back again.

I just gotta wrap my lips around it. I release the hand that was aiming it up and it springs back toward the heavens. It's so hard now that it's dancing with Jack's heart rate. I rise up on my knees and kiss the end, sucking in that growing drop of pre-cum. Tasty.

I slide my lips over the head until my upper lip drops into that big groove between it and the shaft. Jack's raises his head to observe this new sensation. Our eyes lock once again, I tilt my head back a bit, keeping my upper lip in the groove, but giving my tongue access to his frenulum, and I slather my tongue back and forth over it.

"Oh my god," moans Jack. "That's so fucking good." And his head falls back, staring into the twilight. I keep up this onslaught with my tongue, back and forth, back and forth. It isn't long before Jack suddenly grabs my head. "Whoa!" and making me stop. "I'm not ready to finish yet."

I pull my mouth off of his cock. "Me neither, Jack. I want to draw this out. You just stop me whenever you need to."

I suck his cock back into my mouth again. Curious how much of Jack I can swallow, I force my mouth downward, but I'm gagging at about half way.

"That's OK sweetie. You don't need to do that. Your tongue is your gift, and it doesn't hit my sweet spot down there."

So I proceed to focus on the top half, up and down, slowly, with my tongue covering every last square millimeter of the underside. Up and down. Up and down. Once more Jack grabs my head to stop me.

"God, I was so close. You are so good babe."

He's all wet and slippery now, so I go to work with my hand. Starting at the top with an almost too-tight grip, I slowly slide over the head, pulling his little slit open emitting another drop of pre-cum. I do it again, from the top, and the pre-cum drop grows. A couple more of these and it's running down.

So I use that lube to forma ring with my thumb and forefinger in that groove and I twist back and forth, my palm focusing on his frenulum. Jack's moaning and uttering something undecipherable, until he once more yells, "Stop!" and I let another near-orgasm subside.

Let's see, for my next course, I tilt my head to one side, plant my puckered lips on the underside of Jack's cock. Sucking hard, I slide up and down his shaft a few times, finishing on his frenulum again, opening and closing my lips, sucking it in and pinching it back out again. Jack's moaning again, and it isn't long till he cries out, "Stop again!"

Jack:

Clara's holding my dick. Examining it. And she certainly seems please with her new toy. The way she rubs her soft, wet hand up and down the length of my dick is just making me harder. She lets it go, letting it spring back upright again.

She laps up a drop of pre-cum, seems to enjoy the taste. Then she slides lips over the head, sucking me in. With just the head in her mouth, she sliding her tongue back and forth across my frenulum. "Oh my god. That's so fucking good." She's keeping it up, back and forth, and I'm about to come. "Whoa! I'm not ready to finish yet."

"Me neither, Jack. I want to draw this out. You just stop me when you need to."

Her mouth is on my dick again. She's sliding down, trying to deep throat me, but starts gagging.

"That's OK sweetie. You don't need to do that. Your tongue is your gift, and it doesn't hit my sweet spot down there."

So she pulls back up, but then down. Up and down, but slowly, just the way I like it. Her tongue is sliding through every nook and cranny. So good! God, I'm about to cum again. I grab her head to stop her.

"God, I was so close. You are so good babe."

Now she's going to work with her hand. I'm all wet with spit, and she forces it down over the head with, oh God, such a tight grip. Like penetrating a tight snatch. And another, and another. Now she's twisting her thumb and finger back and forth through the groove under the head. Jesus! "Stop!"

After another pause, Clara's starts sliding her puckered lips up and down the underside of my shaft. But that suction. Incredible. God, she focusing on my frenulum again. Here comes another one. "Stop again!"

Pleased with her handiwork, and her 'mouthiwork', she sits back on her heels, giggling at what a quivering wreck she's made of me. Then she spits on her hand and spreads it between her boobs. Up on her knees again, she's wrapping her boobs around my dick. Jesus, they're so big I can't even see my dick. But then she starts sliding her boobs up and down, the head peaks out over her boobs just for a moment, and disappears again.

It looks so incredible. Her sweet face. Her magnificent breasts. Her nipples staring me in the eyes. And my dick getting the ride of a lifetime. I'm dumbfounded! Speechless! So much so that another orgasm sneaks up on me. But before I can say anything, it's too late. My body goes rigid. And an uncontrollable groan starts moderately, but quickly grows in intensity. Realizing what's happening, Clara releases her boobs and grabs my dick to put it in her mouth, but too late for the first shot. It boils up, surging along the length of my dick, and squirts up into the air. She catches the remaining spasms in her mouth -- God there must be 15 of them -- swallowing it all down.

She resumes sucking on my dick, but I'm so sensitive right now that I can't take it, and grab her head one last time. So she uses her fingers to clean up the spatters on my belly and lick them off.

"I thought you were going to stop me."

"I was lost in the moment. How'd you learn to work a dick like that? You're so young."

"I had a good teacher. Another older man. Not as old as you though. He was one of my professors."

"You got a thing for older men?"

"Yeah, I think I kinda do. Don't get many opportunities though."

The last of the sunlight is gone. The lights of Albenga glimmer across the water, and cast gentle glow to the sky.

"So Clara, I think it's your turn."

Clara:

Change up. I think what Jack needs is a good titty-fuck. I wet my cleavage with a little spit, take his cock between my tits, and start sliding them up and down his shaft. His purple head now looks kinda cute peaking over the top once every second. Jack seems to be enjoying this, both the feeling and the sight of his whole shaft being lost in my big, luscious tits.

Oh, shit, he's coming already! I missed the first spurt! Damned if he didn't shoot a foot high! I stick his cock back in my mouth to finish him off. Pretty good load, too.

"I thought you were going to stop me."

"I was lost in the moment. How'd you learn to work a dick like that? You're too young."

"I had a good teacher. Another older man. Not as old as you though. He was one of my professors."

"You got a thing for older men?"

"Yeah, I think I kinda do. Don't get many opportunities though."

"So Clara, I think it's your turn."

"Damn right. But it's a little cold being naked out here. Captain Jack, sir, take me to your quarters."

Jack sits up and grabs my hand. He gives it a little peck then pulls me down into the salon, past the head, and opens the door to the V-berth for me. I walk in.