Ahoy There

All characters are over eighteen. Thank you for reading.

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"Mmmmm," she sighed, her arms around my neck. I was nibbling her collarbone, wondering if now was the time to head south. She had nice tits, and I really wanted to touch them.

Kiss them... suck them... Oh, hell, as a reluctant virgin, I'd settle for anything.

Even making out with her was better than I'd managed with any previous girlfriend. Things with Jayne were definitely looking up.

I'm not just saying that because she was straddling me on the front seat of my car, and I really was looking up. We'd been going out for several weeks, and what had started out as a few awkward kisses had progressed to some very hot ones, but nearly every attempt to escalate things to include even some petting, had been rebuffed. I did have my hands on her ass right now, but her boobs remained off limits.

A bit of a double standard at work here, as I'm certain she could feel the lump she was causing in my pants. She was, after all, sitting right on it. Her hot little pussy was safely protected by her tight jeans, but just like the princess and the pea... well, my lump was much, much bigger, but you get the point... she had to know it was there.

Her lips found mine, and she pressed herself tighter against me, making me even more aware of the delicious fullness of her breasts. My hands wandered up her back unchallenged, tracing the lines of her bra, but when I moved around the sides slightly, just enough to feel the swell against the heels of my hands, she pulled back.

"Sam, please... I'm just not ready for that right now," she said softly. "Please be patient."

Patient. Are you fucking kidding me? Every week, I go home with a case of blue-balls that would kill a horse, and you want me to be patient? I think I've been more than patient. Lemme at those tits, honey. I'll show you patient.

"Okay, I'm sorry. I got carried away," I replied, obviously editing my internal voice to avoid burning my bridges completely.

"Thank you, honey," she smiled, rolling off my lap. "I think you had better take me home, now. It's getting late."

It took a few minutes to de-fog the windows of the car, and for the blood to exit my swollen penis, but we were soon on the way back to her house. As we pulled to a stop in front, she turned to me.

"Oh, hey, I almost forgot," she said, with some urgency. "My Mom has a question for you. Are you coming over tomorrow?"

"Well, I, um... what question?" I asked.

"I didn't ask her. I just said I'd ask you. Are you coming over or not?" she replied, somewhat tersely.

I did enjoy using their pool, and seeing Jayne in a bikini was always nice, reminding me what I was being, um... patient... for. On the other hand, the thought of being grilled by her mother was less appealing.

"Yeah, yeah, I'm coming," I told her. "Should I be worried?"

"Why? We haven't done anything yet," she smiled, giving me a quick kiss goodnight. "See you tomorrow."

We haven't done anything yet.

Yes, I am aware. Painfully aware.

***

"Hi Sam," Jayne smiled, letting me in the front door. She was wearing a cover up, but it was open down the front, giving me yet another tantalizing glimpse of the breasts I longed to sample. "Come on in. My Mother is out back, and really wants to talk to you."

There it was again, that feeling of dread. I reminded myself that we hadn't done anything other than kiss each other. Her mother couldn't be mad about that, could she?

I walked out the back door, onto the pool deck, expecting to have Jayne right behind me, but she had turned down the hall to her room.

"Sam! Over here," Mrs. Farmer called, raising her arm from her place in the pool. I moved in her direction.

Oh my... I thought, looking down at her. If daughters really do eventually look like their mothers, it was still more reason to covet Jayne's body. She already resembled her mom facially, and I thought they both could pass for Jacqueline Bisset in the right light, with their thick, dark hair and beautiful eyes.

Mrs. Farmer was treading water in the deep end, and that motion set up a ripple in her chest that was impossible to ignore. Her boobs were significantly larger than those of her daughter, and Ms. Bisset as well. I tried not to stare too much.

"Jayne tells me that you are the one to talk to about all things nautical," she said as evenly as possible through the exertion of keeping her head above water. "Is that correct?"

"Um, yeah, I suppose so," I nodded, my eyes darting up and down between her face and dancing cleavage. "I've been on more boats than I can count, ever since I was too little to reach the wheel. My Dad teaches the power squadron classes, and occasionally does private lessons for advanced sailors."

"Help me out, please?" she asked, tilting her head toward the nearby ladder. I moved to the top of the treads, and took her hand when she arrived, pulling her up and out of the pool. "Thank you."

She stepped over to her lounge, and used her towel to give her hair a preliminary drying, a process that did nothing to quell the activity in the top half of her bathing suit. She finished and wrapped herself in the towel, finally putting that distraction to bed, so to speak. Taking her seat, she gestured for me to sit as well.

"I have a friend who owns a boat, or at least her husband did," she explained. "He passed away a few years ago, and up to now, she's been content to think of the boat as a floating lounge where she can meet her friends for drinks. It's been a long time since the boat left the marina, but it's been well maintained, and now she wants to learn to sail it."

"I see," I nodded. Like her friend, Mrs. Farmer was a widow. Jayne's father died almost ten years ago. "So, why me? There's plenty of people who could teach her."

"Yes, I'm sure there are, but she heard me talking about you, and figures you might be interested in the money more than someone older," Mrs. Farmer continued. "To be honest, I think she has some trust issues with men her own age. Golddiggers are not exclusively female, if you follow me."

"Ah, okay," I laughed. "Rich, is she?"

"Let's just say comfortable," Mrs. Farmer smiled. "Considerably more comfortable than Jayne and myself. She can certainly afford you."

"Thank you," I nodded again, mentally counting the cash, which I could use. As for the comfort level, Jayne had told me that her mother well enough off that she didn't need to work to pay the bills, but not well enough to be frivolous. Apparently, her friend could afford frivolous. "When does she want to start?"

"Tomorrow?" she asked.

"Tomorrow works for me," I replied.

"Okay. I'll let her know. Pick me up here?" she suggested, putting me in the driver's seat.

"Yes, Ma'am. See you then, Mrs. Farmer," I answered. I looked around for Jayne, and eventually found her in her room. She was on the phone, gossiping with one of her friends. I waited as long as my sanity could hold out, before waving goodbye and heading home. It wasn't very likely we'd be doing anything more than swim, anyway, and I had a distraction.

Tomorrow, I'd get paid.

***

"That's her boat, down there," Mrs. Farmer pointed.

Below, in the marina, a gaggle of sailboats of various sizes and styles filled the slips. One stood out. A bit longer than most, about fifty feet or so, the name on the stern was clearly visible.

"Gwendoline? She's a ketch," I said, still scanning her lines.

"Do you know Wendy? I'm sure she'd be thrilled to hear you say that about her," Mrs. Farmer smiled.

"Huh?" I frowned, lost in the sudden turn the conversation had taken.

"You said Wendy was a catch. I mean, she is very attractive, and since her husband passed, I suppose she is available... but, well," she shrugged.

I was still trying to decipher what she was saying, when someone appeared on the deck of the boat in question. Even from this distance I could see it was a woman. No man has curves like that. It suddenly occurred to me what the confusion was about. Her lines were nearly as impressive as the boat's.

"Oh, I get it. I was talking about the boat. The Gwendoline. She's a ketch... a two-masted sailboat with a taller main mast and shorter mizzen. I said ketch, not catch," I laughed. "That's so funny."

We were both still laughing as we walked along the floating dock towards the boat. The woman on deck noticed us and waved. It was that overly animated wave that people on boats all seem to have.

"Hi Rose!" she called out, waving her arms wildly. Her movements shook her ample chest, drawing my eye to her more closely.

Hmmmm... maybe I did mean catch, I thought, eyeing the blonde bombshell. She must have guys lined up around the block, wanting to claim a rich widow, with a body like that.

The horizontal red stripes on her polo top stretched over her lovely breasts, exaggerating their curves, especially as they reverted to parallel in the area near her narrow waist. Below, a pair of miniscule white shorts hugged her hips tightly, and long, smooth legs completed the journey down.

Oh, and she was pretty, too. Not even the large, mirrored sunglasses she wore could hide her high cheekbones and brilliant smile. Long waves of blonde tumbled over her shoulders, and a white sailor's hat topped it off.

"Hi, Wendy!" Mrs. Farmer smiled, returning the wave in a more reserved fashion. "This is Sam. I told him about you wanting to learn to sail. He's here to help."

"You mean we actually get to go out on the boat, instead of just drinking on deck?" Mrs. Turlington smiled, taking my hand as we climbed aboard. "Nice to meet you, Sam. I'm afraid this thing was my husband's toy, not mine. For years, I thought he was cheating on me with a woman named Gwendoline. It never occurred to me it was a boat."

"Well, how many Gwendolines do you know?" Mrs. Farmer asked with a chuckle.

"I haven't been Gwendoline since I was little, and I haven't been little for a long, long time," Mrs. Turlington laughed, looking down at her chest and shaking her shoulders. "See?"

"Yes, Wendy, we've all noticed your boobs," Mrs. Farmer added, rolling her eyes. "I brought us a picnic lunch," she giggled, nodding toward the bag in her hand.

"And I always have wine," her blonde friend replied. "It's a party!"

"Let's get under way," I smiled, deflecting the embarrassing turn in the conversation. I didn't need more reasons to ogle either of them.

"Aye, aye, Captain," Mrs. Turlington grinned, standing to attention and making a clumsy salute. She again thrust her considerable chest out proudly. "Want me to do the cloth, thingies?"

"Sails?" I asked.

"Yes, that's them. The sails. Should I put them up?" she replied unsurely.

"No. No sails in port. We motor out," I told her.

"Oh, good. I don't know how they work, anyway," she smiled, immediately turning to her friend.

"All right... cast off," I directed, expecting to see my students paying attention, but that wasn't the case. The two of them were cackling happily, in a world of their own. "Or, not," I shrugged, deciding to just do it myself.

I'm not even sure the women noticed as I hopped back to the dock, scooting forward to free the line at the bow. As the bow began to swing slowly, I moved aft, untying the stern line and stepping aboard once more. The ladies were giggling amongst themselves, oblivious.

Within seconds, I had pushed the button, urging the small diesel engine to life, and we were slowly cruising out of the marina. With a final turn to port, we cleared the breakwater. It only took a few minutes before I could see and feel the effects of the wind.

It was time to sail.

The motor coughed once as I turned it off, and I headed forward to where the ladies were chatting. I stood on the fringe for a few seconds, listening to them gossip, before interrupting.

"So, who wants to learn more about sailing?" I asked.

"I guess that would be me," Mrs. Turlington replied, turning to face me.

"Okay, let's start with directions," I nodded, pointing. "Port, starboard, fore, aft, or bow and stern. Main mast forward, mizzen is aft," I added looking up. I continued, pointing out certain lines that were part of the rigging, Mrs. Turlington did the same, craning her head upward and holding the jaunty white hat on her head while the wind tousled her long blond waves.

I was still talking when a small wave momentarily tilted the boat unexpectedly.

"Ooooo, oooops," Mrs, Turlington giggled, tumbling against me. Her large breasts cushioned the blow as I caught her in my arms, holding her up. Those major melons felt so delicious, squashed between us.

"You okay?" I asked, propping her up.

"Yes, I'm fine," she answered, getting her feet under herself. Her boobs remained pressed against my chest. "Why does the sea have to move like that?"

"It just does," I laughed, looking over her shoulder to where Mrs. Farmer was watching, a smirk on her face. "There is a reason high heels are not normal footwear on a boat, however. You might want to change into some deck shoes, before you break an ankle or fall overboard."

"I suppose," she pouted, "but they're so pretty!" Now balanced once again, she extended her right leg to show me the shoe. "And don't you think they make my legs look nice?"

When was the last time a very attractive older woman came right out and told you to look at her legs?

Well, she did ask nicely.

My eyes first went to her foot, where the shoe really did look nice on her. Five perfectly pedicured and painted toes peeked out through the opening in the tip. Her ankle was thin and delicate, flowing upward into a very firm, shapely calf, which she made sure I could see by rotating it slightly. My gaze tracked up, across the creamy skin of her thigh, which was visible almost all the way to her hip. If I thought the white shorts looked tiny from a distance, they looked even smaller now, with an inseam of perhaps two inches. She turned away.

"And my butt..." she smiled, urging me to check it out.

Yes...Nice ass.

"Alright, Wendy," Mrs. Farmer cut her off. "Sam is here to teach you to sail, not stroke your ego. Go change your shoes."

"Party pooper," Mrs. Turlington answered, sticking her tongue out at her friend. "Fine, I'll go change into something more nautical. I'll only be a minute."

Just because I hadn't shared my opinion of her legs out loud, didn't mean I didn't have one. I watched her ass wiggle as she walked away, disappearing down into the cabin. That ass was fi-iiiii-ine. So were the legs. The well packed chest as well.

Mrs. Farmer intruded on my lusty ruminations by stepping over beside me, causing my eyes to caress her own curves with similar appreciation. The only difference was that I'd seen her many times before. The thoughts were the same. I was on a boat with two very desirable older women.

"Do you want to set sail, Skipper?" she asked.

"No, we'll wait for Mrs. Turlington. She'll only be a minute," I repeated, trying to remain focused on my job.

"Sam, if you're going to date my daughter, there's something you need to understand about women in general," she laughed. "Our minutes have little in common with the clock the world runs by. Wendy in particular. I guarantee you won't see her for half an hour. You asked her to change her shoes? She'll have to pick out a new outfit to match them."

"Really? Well, okay then. Let's get moving," I nodded. I had heard something similar from my father, but my mother had always been pretty punctual. Hearing it from another woman made it true, I guess.

This really was a nice boat. Equipped with auto-furling, you could quite effectively sail her alone, from the cockpit. It only took a minute to get the sails set, and we were soon slicing smoothly through the waves, headed offshore and north along the coast.

Mrs. Farmer took a spot to my left, sitting with her legs tucked under her and twisted to face into the wind. That breeze had her long dark hair flowing out behind her, in a very attractive fashion. Her sunglasses obscured her eyes, so I couldn't see if she was glancing my way, but neither could she, and I was definitely watching her out of the corner of my eye. Two distinct bumps had formed on the smooth curves of her breasts as the wind penetrated her shirt, causing her nipples to tighten in response.

She was right about her friend, however. It was indeed almost a half hour before Mrs. Turlington reappeared from below, and she was in a completely different outfit.

It wasn't much of an outfit, mind you, but it was perfectly matched to the clean, white sneakers that had replaced the previous high heels.

She still had the sailor's hat on, but the red-striped polo and white shorts had been supplanted by a diaphanous white cover-up. What it was covering was a very brief navy-blue bikini, and it wasn't really doing a good job. The breeze caused by our forward motion had it fluttering open, leaving her body quite clearly available for drooling purposes. She took her spot next to Mrs. Farmer, giving me even more reasons to glance that way.

Now, I know I was supposed to be here to teach sailing, but I was enjoying myself. Besides the obvious reasons seated to my left, there was the boat itself, or herself. I'd never been at the helm of such a luxurious vessel. This was no little day-sailer. She could accommodate longer voyages easily, and her large sail area made her very powerful, especially with the wind.

We had been out for about an hour or so before Mrs. Turlington smiled and moved over to my side. She leaned against my shoulder with her big, soft boobs, and spoke into my ear softly.

"I want you to teach me how to control this boat, just like you're doing right now. It's very impressive, young man," she said above the wind. "Can you find us a nice, quiet lagoon or something, where we can have lunch?"

"I think you mean a cove, but we'll work on it," I laughed. "Yes, I'll find us a spot, Ma'am."

"Ma'am? Oh, god... You'll have to stop that or I'll really feel old," she replied, flashing her smile. "Please, call me Wendy. Leave the Ma'am talk ashore, okay? Do I look like an old lady?"

She leaned back, again inviting me to cast my eyes over her form. Beads of sweat adorned the upper curves of her breasts, dripping in damp trails down into her deep cleavage enticingly.

"Um, no Ma'am," I said reflexively. "I mean, no, Wendy. Not an old lady."

"That's better," she nodded. "Now, find us a spot to park."

"Anchor," I corrected. "Cars park, boats anchor."

"Whatever," she giggled, taking her seat. Mrs. Farmer looked at her, then at me, and shook her head.

***

Friday night found Jayne and me steaming up the windows in my car again. She had me wedged into the corner behind the wheel, pressing her body against me in an agonizing fashion while we made out madly.

I had my hand on her left breast.

Hallelujah, at last.

It was so soft, yet firm, and filled my grasp so nicely.

*

In the week since we'd last been parked here, my dick had been hard nearly every waking moment. What she didn't know is that her young, nubile body was only a small part of what was bouncing around in my head.

Mrs. Farmer, or Rose as I was now instructed to call her, had packed a very nice lunch last weekend. Once I found us a nice, secluded bay on the leeward side of a small island, we had anchored, and she broke out the food. We sat around in the helm area, nibbling sandwiches and cheese, before Wendy ducked into the cabin. She came out with a coke for me, and a bottle of wine for herself and Rose. It was very peaceful out there. At least, until the second bottle was opened. And then the third.

By then, Rose had gone inside to change, and now both of the mature beauties were clad only in scanty bikinis. They were chatting and laughing, enjoying themselves greatly in the warm sunshine. The tanning oil was flowing freely, and their curvaceous bodies had a shine to them that enhanced every luscious inch of skin.