Ahoy, There!

My god, they were sexy. Drunk, but undeniably sexy. Being the only male onboard, I was the target of some merciless teasing. Wendy in particular took great delight in shaking both her booty and her spectacular rack in my face. It was a voyeur's dream, except I had no chance to take care of the resulting erection in a timely fashion. After a couple of hours of torture, it was Rose that called off Wendy's assault. We weighed anchor, and headed back to the marina.

Rose didn't say too much in the car, on the way to drop her off. I put it down to the wine. She smiled as she got out of the car, and leaned in the window to talk to me.

"So, that's Wendy," she said, her big breasts hanging in her bikini top for my viewing pleasure. "I'll let the two of you schedule your trips. Is it okay if I tag along occasionally? I had a good time out there. Who knew boats were so much fun?"

The blood that had finally drained out of my penis turned around, and swelled it again as I looked right down her fabulous cleavage. I caught her eyes on my bulge for an instant, and she bit her lip unconsciously.

"Of course," I replied, and she said goodbye, heading inside unsteadily.

*

Now, I had her daughter's breast in my hand, and was fondling it gently, feeling the nipple stiffen into a little pebble of desire. I made the next, logical move, trying to get my hand inside her top, at least as far as her bra.

No such luck.

"Sam, not now, okay? Just be patient," she told me. Again.

"Fine," I exhaled, frustrated. "I'll take you home, so I don't get carried away."

The drive was quiet, and after she left me alone in the car with a kiss and a smile, I sat there, thinking about my situation.

My frustration with Jayne.

My very exciting new student, Wendy.

And... the disturbing rumours I had begun to hear at school. Rumours that Jayne wasn't being honest. Rumours that she was playing me for a fool. Rumours that someone else was involved. Rumours that, if true, cast serious doubt over our relationship.

"Fuck it," I grumbled, and went home to jerk off to memories of Wendy and Rose.

***

"Look over there," I pointed, causing Wendy to turn her head to port. "More wind over there. Let's motor in that direction."

"You got it, Teach," she laughed, spinning the wheel left.

It was a glorious day, without a cloud in the sky, and unfortunately, hardly a breath of wind. We'd been searching for some sailable breeze since we left the marina, and Wendy was happy to 'drive', taking over at the wheel once there was little to hit. I had directed her to a patch of water that was being ruffled more by wind than the rest of the glassy surface, but by the time we got there, that gust had died out. It appeared that there would be no sailing today.

"No wind," she pouted. "How can I learn to sail if it won't blow?"

I couldn't see her eyes, as they were hidden behind her sunglasses, but the twitch at the corners of her mouth told me she was aware of the suggestive nature of her words. Her ruby-red lips parted a bit more, and I envisioned them sliding along my cock.

It did seem that her default setting was a bit on the flirty side. She had, however, learned a few things from our first outing, and greeted me this time appropriately shod for wet, slippery, unstable conditions. Her ensemble today was a monochrome of white, from top to bottom. The tiny shorts were back, and her top was every bit as snug as last week, stretched tight over her round boobs. Even her bra was white, and its lacey cups telegraphed through the shirt quite visibly.

It was just the two of us today, as Rose had been unable to join us. I must admit, the prospect of being trapped alone with Wendy was as much terrifying as it was titillating. Maybe I could find us a deserted island on which to become shipwrecked?

Not likely. Even a total rookie such as Wendy could man the helm, today. All I could teach her was basic steering. She quickly got the hang of the port-to-port pass, and was soon doing it without me reminding her. Of course, she had her own, unique way to remember it.

"The logo on a shirt is on the left boob... Left is port... I show them my port boob," she smiled.

"Um, yeah, that's about right," I replied, shaking my head.

"Not right. This one's my starboard boob," she giggled, pointing the orb in my direction. Her nipples were at attention again. She liked playing this game.

It was a short day on the water, and we spent some time watching the seals lounging on the rocks of an island that would disappear at high tide. She pressed herself against my back as we sat and observed them.

"No wind, but I still had fun, and I still learned something," she said quietly in my ear. "You're a good teacher. Thank you, Sam."

"Until next week, Wendy?" I replied.

"I look forward to it," she answered. There was a sultry purr to her voice when she said it that captured my imagination.

***

"What's wrong?" Jayne asked, as we parked in our usual spot. It had taken me all evening, through dinner and a movie, to make the decision.

I needed to know. Those rumours hadn't subsided. If anything, they grew louder, and I didn't like what I was hearing. I was hearing a lot.

She didn't wait for an answer, rather just planted her lips on mine. It derailed me enough that I merely kissed her back, and even moved my hand up to cup her left breast again. I chose to proceed, and began to unbutton her blouse, intent on further inspection of her tits. She pulled back.

"Excuse me?" she frowned.

"Oh, I thought a new baseline had been established," I replied, fixing her with a stare. "You've gone further with, what's his name? Mitch? I figured that applied to me, as well."

I watched her eyes go from her initial anger, to wide surprise at the accusation, then to a neutral acceptance that she'd been caught cheating. She said nothing, and simply turned straight in her seat, staring out the windshield.

"We never said we were exclusive," she offered, a weak defence.

"Maybe not in so many words, but the implication was clear enough," I returned. "You knew how I felt about you. How long have you been cheating?"

"Three weeks," she replied. "Again, I wasn't cheating. I just wanted to date him too."

"That's not exactly what I heard," I growled. "He's running around, telling the world how he fucked you, and how you have this other guy on a string, playing him like a fish. You understand, as the guy on the string, how I might be upset by the news."

"So you want to fuck me, too?" she said softly, not even trying to deny it. "Why not? It's fun. Let's go. Get your cock out."

"Not likely," I snarled. "You don't get to buy your way out of it, even with a piece of your delectable ass. You're busted. You're caught. You're a cheater. I'm done with you. Get your entertainment elsewhere. Oh, and tell him he's lucky he goes to a different school, or I'd knock his fucking teeth out."

I turned the key, starting the engine. I briefly considered tossing her out right here, but I still had to deal with her mother occasionally, and things would be awkward enough without abandoning her alone in the night.

Neither of us said a word until I had stopped in front of her house.

"Don't apologize. Just get out," I told her sternly.

"I wasn't going to apologize," she spat.

"Yeah. Why start now?" I laughed. "Fuck off."

***

Two days is not much time to deal with what I was feeling. I was hurt, betrayed, angry, embarrassed, ashamed... and those were just the ones of which I was aware. I contemplated cancelling Sunday's day at sea with Wendy, but the calm weather last week had already set us back. Besides, I could use the distraction.

When I arrived at the marina, that's exactly what I found; a distraction named Wendy Turlington, dressed today in a short, baby blue sundress.

"Shall I take us out, today?" she asked, her eagerness bubbling to the surface. "I'll be careful. You tell me what to do, and I'll do it, okay?"

"Sure. I'll cast us off," I smiled, immediately happy I hadn't cancelled. Wendy had a way of rubbing off on those around her, and she was fun, just what I needed. Within seconds, the lines were loosed, and she was delicately easing us out of the slip. I watched the bow swing into the clear, impressed at how far she had come in only a couple of lessons. She handled the boat very well, even in the relatively tight confines of the harbour. We slowly wended our way out, turned left through the breakwater, and were clear.

There was wind, today. It was time to sail. The breeze was out of a different direction, but we could still make it work. I let her stay at the wheel, and talked her through deploying the sails. I left the mizzen furled.

"What about this one?" she asked, gesturing upward over her head.

"We have to sail into the wind. The problem with a ketch is that the mainsail spillage stalls the mizzen. It's great in every other breeze, just not upwind," I explained.

"A ketch? I thought it was a sailboat," she smiled, clearly not as ditzy as she often pretended to be.

I don't know it you've noticed, but certain people talk with their hands. Pilots, race drivers, and sailors are among them. I used my hands as the wind, and she supplied one to play the boat, as I explained the technique we were working on. Her hand was soft, and I enjoyed the contact of the tack.

I also enjoyed the effects of the wind, each time we changed direction. Every time we went from right to left, or left to right, the breeze would become a jumbled, swirling force in the area of the cockpit, and Wendy's sundress would billow upward. It was very Marilyn Monroe, except Wendy had two hands on the wheel, and none left to push her dress down. Her panties were white, a little bit shiny, and cut high over the hip, leaving a good portion of her lower glutes bare.

What is it about underwear that is so intimate? I had seen her in a bikini in the past. What I was seeing now was no more revealing than that, but this was so hot, it was all I could do not to grab her ass. She made no effort to stop the dress from flapping.

My dick was so stiff it hurt, but I was able to find a comfortable position for it if I stood. Looking over her shoulder, I could see the pointy tips of her nipples. Was it the cold? I think not.

Oh, how I wanted to reach around, and grab both her big beautiful breasts. I'd rip her dress down, and...

"Should I head for that cove?" she asked, pointing to the right, and the spot where we had lunch before. "I'm kind of hungry."

"Um, yeah, me too," I laughed, as the breeze gave me yet another view of her ass. So firm, and smooth, and tanned...

I caught her glancing at my crotch, while she caught me staring at her ass. I think we both smiled, and she steered in the direction of the island. She even knew enough to switch to the engine as we entered the mouth of the cove, and I used the boathook to grab the buoy for us to moor the boat. She shut down the engine.

"Give me a few minutes to get lunch together," she smiled, and I caught one more quick glimpse of her smooth thigh as she scooted down the ladder into the cabin.

Yes, indeed... Just the distraction I needed, I thought, leaning back in the corner of the seating area. I looked around; yet another perfect summer day, with blue water, bluer sky, and a thick carpet of green that covered the islands, except where rugged outcrops of stone poked through. An eagle dipped low, snatching a fish for his lunch, and bringing my attention back to the present.

I heard a low moan from below, then another.

"Everything okay, Wendy?" I called out.

"Oh, yes," came the eventual reply. "Just, um, missing an ingredient I needed. I'm almost ready."

"Okay. Do you need any help?" I offered.

"No, not yet, anyway," she laughed, appearing at the hatch way. "Later, maybe. I'm sure you'll know when." With that she dropped out of sight again.

I was still trying to make sense of her cryptic response, when she came into view once more, carrying a tray. I jumped up, taking it from her so she could climb the ladder. A moment later, she had unfolded the small table in the centre of the cockpit, and I placed the tray on top.

"Sandwiches, cheese, various other things to nibble on," she smiled, in a way somehow different than I'd seen before. "I forgot the drinks. Just a sec."

One more trip below, and she was back with her usual bottle of wine, a single glass, and a non-alcoholic drink for me.

"Sometimes, Sam, I almost forget how young you are," she explained, taking a seat next to me. "You are so mature, and so confident when you're teaching. More a man than a boy. Rose told me what happened with Jayne. I'm sorry."

And... There goes the distraction. All those negative emotions came flooding back, overwhelming my composure. I'm sure it was apparent on my face.

"Oh, Sam, I'm so sorry, I never should have brought it up," she said softly, reaching out to take my hand. "I know it may not seem like it now, but mark my words... you'll get over her, and someone better will come along. You won't even remember 'what's her name'."

I didn't answer. Wendy sat back, eating the sandwich she had picked up, a thoughtful look on her face. If I had been fully aware, I might have seen something else in her eyes. She stood, and stepped over to the helm.

"I really want to thank you for helping me learn to sail. I understand now why my husband spent so much time on this boat. It's very freeing. To know he named it after me, and the feelings I feel now... I can't help but take it as a compliment. I know I still have a lot to learn about sailing her," she smiled, turning to face the wheel, "but if you'll teach me, I promise to listen. Maybe I can return the favour somehow?"

With both hands on the wheel, she couldn't have had anything to do with what happened next. As if on cue, a small gust kicked up, tossing the hem of her dress upward again. I was sitting, so I didn't miss the show. Her ass was at a very convenient viewing height.

The panties that were visible earlier? No longer. I saw nothing but bare flesh, and between her casually spread thighs, the damp folds of her labia, dangling open.

I heard the sound of her grip on the wheel tighten, a squeak of skin on teak. Her head was turned, watching me out of the corner of her eye, as the wind played its part in our game. It fluttered through again, baring her succulent sex for my eyes once more. She reached back and caught the edge of her dress, now holding it up actively, while wagging her hips from side to side.

I may have been blind enough to let my girlfriend to fuck another guy without noticing, but I wasn't dumb. I stood and moved behind her, letting her rub her firm behind against my bulging erection.

"Oh, Sam... Yes. Such a nice, hard cock," she purred, arching her back like a happy kitten. "Touch me, please. Touch me."

If you recall, I told you earlier what I'd like to do to her, in just such a situation.

My hands slid around her sides, cupping the fullness of her breasts. No bra stood in my way, as I squeezed the large globes gently, kneading them together.

"Mmmmm, yes, that's it," she moaned, leaning her head back against my chest. "Grab my tits. I've always loved it when my man does that." She turned slowly in my arms, dragging her breasts out of my grasp. "I like my tits. Nice and big, they turn men into drooling fools. Do you like my tits?"

I was trying to form a sentence in reply, when she hooked her fingers in the elastic neckline, and tugged her dress downward. Her boobs were dragged lower, before bouncing back up, clear of the dress and beautifully bare. She pinched her already erect nipples and twisted them, making them longer and thicker before my eyes. Her rosy areolas were a tight, wrinkled disc about three inches in diameter around each delicious nub.

I nodded, words continuing to fail me.

"Another boob man, huh? Well, I think we're going to have fun," she smiled. "My turn."

Dropping slowly to her knees, she inhaled, then groaned.

"I smell man juice," she said softly, reaching up with one hand. She delicately traced a finger around, before palming the lump in my shorts.

"Sam?" she gasped.

"Yes, Wendy?" I answered, no longer mute.

"Is this a third mast for the boat, or are you really, really, REALLY happy to see me?" she asked, getting a grip on the zipper. She dragged it down, and my shaft sprung out, slapping against her cheek. "Mmmmmm, and commando, too. Oh yes, we're definitely going to have fun."

"You're not just doing this because of Jayne, are you?" I asked, like an idiot. Talk about bad timing. Fortunately, Wendy didn't care.

"Fair question," she smiled, now stroking my hardness slowly with one hand. "Stupid question, but fair. No, I'm not doing this because of Jayne. Well, sort of. In truth, I was ready to fuck you our first time out, but Rose stopped me. She didn't want me in the middle of her daughter's relationship, and she was right, although if I'd known you had THIS hanging between your legs, I might have been more difficult to dissuade. Then Jayne pulled that shit on you, and even though we both knew it, we couldn't tell you. Sorry," she finished, kissing the head gently.

"Not your fault. Am I the rock, or the hard place?" I asked, oblivious to the double meaning.

"Mmmmmm, rock hard," she purred, rubbing her face across my cock. "Now, thanks to her cheating, I no longer have that conflict. Just as well. She doesn't deserve such a lovely big dick as this. Excuse me... I just have to..."

"Oh, shit..." I groaned, as her pouty lips parted and slid over the head. Her tongue danced around in circles, and she pushed forward, sucking my shaft deeper. My first blowjob, and it comes from a woman old enough to be my mother. Oedipus would be proud.

My hands had found their way to her head, and I grabbed two handfuls of her lustrous blonde mane. She moaned, sucking harder and deeper, while I looked down into her pretty eyes.

The nod was almost imperceptible.

My hips began to thrust instinctively, pumping my steely shaft in and out of her mouth, and causing saliva to leak out the corners. Her hands were on my ass pulling me in with each stroke. Excitement reached critical mass.

"Mmmmmm, hmmmmm," she moaned again. "Mmmmmmmmmmm..."

"Ohhhhhhhhhhhhhhhhhhhh, shiiiiiiiiiiiiiiiiiiit," I grunted, as my load spewed down her throat. It was better than I could possibly have imagined, and it seemed like I came for hours, but that might just be because time stopped for me. When it started again, Wendy was still sucking and moaning, trying to draw every drop out of my balls. It tickled, but she had her nails digging into my ass, and I couldn't pull away. All I could do is grit my teeth, and hold on.

At last, she released me, and my spent noodle slipped out of her mouth. A streak of cum on her chin marked its passage.

"Better than any dessert I could come up with," she laughed, licking her finger after cleaning her chin. "You okay? Don't fall overboard. I'm only getting started with you, stud. Being eighteen, I'm sure you will be hard again in about ten minutes, you beautiful man. Let's go to the cabin."

Oh yeah. We're kind of exposed here, I thought, realizing I was standing on deck, pants around my ankles, with my dick dripping spit and semen. Wendy was essentially naked, with her sundress bunched around her waist, magnificent breasts free to wobble and bounce with her every move. Boats passed by a couple of hundred yards away, close enough for binoculars to get a clear view.

I followed her below, noting her panties on the table.

"Glad you didn't come down when I was making lunch," she smiled, scooping them up and spinning them on a fingertip. "I was getting my courage up, and getting myself off. I saw you checking out my ass when the wind blew up my skirt."