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Sailing with Samantha

Category: Mature
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It was a beautiful warm sunny day — well, hot actually — though the stiff on-shore breeze blowing up from the south made the heat tolerable. Otherwise, it was a perfect day for sailing.

I sat at the wheel of my sailboat, named Felicity, which my wife, Karen, always insisted on calling a “yacht” because it was just over thirty feet in length. Karen wasn’t on board with me.

At the last minute on Friday, her boss had asked Karen to fly to Boston for a crucial project and he needed Karen to meet with the proposal team early Sunday — today — so she’d flown out last evening.

Ordinarily, I wouldn’t have considered going out for a sail without Karen as my crew, but, over a week ago she had promised her favorite niece, Samantha, that Sam could come sailing with us this week end. Sam had been begging Karen all summer to go out on the boat with us.

Before Karen left for Boston she reminded me about taking Sam out sailing.

“Dear, just call Sam and tell her she can come out with us next week end.” I suggested to Karen.

“No good. My brother and Sara are driving her up for freshman orientation Thursday. Sam’s been after me all summer to go out and since last Wednesday was Sam’s eighteenth birthday, I promised her as a birthday present that she absolutely could come with us this week end. So, you’ll have to take her out yourself.”

Sam was not only Karen’s favorite niece, she was more like our third daughter since she’d spent so much time at our house before our girls flew the coop, so to speak. I liked Sam a lot, but I knew she would be pretty useless on the boat. She had often come out sailing with our family in the past whenever our girls would go sailing with Karen and I. But Sam had never shown one bit of interest in helping out operating the sailboat or learning how to sail; she and my daughters had been more inclined to sunbath, listen to rap music and giggle with each other over whatever whispered secrets they shared. Typical teenagers I supposed.

So, it meant I’d be without a crew, that is to say, Karen. I would, in essence, be sailing Felicity by myself.

“Damn. Well, alright … if you promised.”

“Sara said she’ll drop Sam here Sunday morning by nine.”

So there I was, on Sunday, motoring out of the marina, and I needed to get the sails up. I yelled down to Sam, who was below in the cabin changing. I asked if she could come up on deck and give me a hand. If she could take the wheel while we were still motoring, I could get the sails up in just a few minutes, then take the wheel again and Sam could sunbath; which was about all I was expecting of her during our sail.

“I’ll be right up, Uncle John, I’m just getting changed.”

A moment later she popped up through the companion way in a rather skimpy bikini — fairly typical of what she and my girls had usually worn when on the boat. Sam’s build was just about perfect for a bikini. I guessed her to be about five six since she was about the same height as my youngest and Sam was probably not more than a hundred and twenty pounds. Nicely proportioned, with ample, but not overly large boobs. I caught myself looking at her for the first time, not as my daughters’ almost constant companion, but as a mature young woman — and not at all bad looking, at that. When I felt an inappropriate stirring in my groin I forced myself to look away.

“Sam, I need you to take the wheel while I hoist the sails.”

“Oh geez, Uncle John, I don’t know what to do … I never …”

“Don’t worry; it’s a piece of cake. Come around behind the wheel and just steer it like a car.” I said as she came around to stand behind the binnacle on which the boat’s steering wheel was mounted.

“Just keep the bow aimed at that buoy.” I said as I pointed to the red navigational aid several miles dead ahead.

“Bow?” Sam asked.

“The pointy end of the boat.” I answered, with exasperation.

“Oh, OK. But don’t be too long … this makes me nervous, Uncle John.”

“Sam. You’re an adult now … just call me John … Uncle makes me sound … I don’t know … old, I guess.” And I gave Sam a smile.

As I was retrieving the wench handle that I always stowed in the lazarette located just behind the steering station, when I noticed the back of Sam’s bikini for the first time. I was a bit shocked to discover that it was a thong bikini – a mere string running down into the crack between her very alluring cheeks. Sam had never worn such a thing when she was younger and she had sailed with us. It made me realize that she really was an adult — a child no longer. It also re-energized the stirrings I had suppressed a few moments before.

I quickly went up and hoisted the mainsail, unfurled the jib, and got all the lines squared away; all the while, making sure I keep my back to Sam to hide my hard-on that was diminishing, albeit, rather slowly.

“Uncle John! I mean John … there’s a boat coming! What do I do?” Sam yelled from behind the wheel.

I looked back at her and saw her pointing to starboard where another sloop was indeed headed in our general direction. In a few seconds, I determined we were not on a collision course.

“It’s OK. Just hold your course. — point her at the buoy.” I yelled over the sound of the waves slapping the hull and the wind singing through the rigging. I headed aft and took the wheel back from Sam.

“Good job Sam.” I told her. “I couldn’t have gotten the sails up without you.” I lied; though it did make it easier having someone at the helm while I hoisted sail.

Sam had a big grin on her face as she sat down with her back against the deck house. She wrapped her left arm around the leeward jib wench. The boat heeled nicely in the stiff breeze; Sam was on the low side and casually dipped her fingers in the warm salt water as we bounced over the waves.

“That was sort of fun, Unc … I mean, John.” She said. “I almost wish I’d paid more attention when I used to come sailing with you guys; you know, when Jenny and Amy were still at home.”

“Well Sam, if you like, maybe you can take the wheel again in a little bit and see what it’s like sailing her with the sails up.”

“Oh could I? That would be awesome!” She said.

“Sure, but let’s wait till we get a few miles offshore where there’s less traffic. OK?” On week ends everyone in the area came out to sail, or motor, if the weather was good. And that Sunday was no exception.

“OK. I’m going to put some sunscreen on before the sun gets too high.” With that, she went below and popped back up a moment later with her lotion.

She rubbed lotion all over her legs and arms and belly while we headed out into the Gulf. When she was finished, I motioned for her to come over and take the wheel again. As she took hold of the wheel she handed me her bottle of lotion.

I explained to Sam how steering with just the wind driving the boat was different than when the engine was doing the job. As one would expect with a novice helmsmen, the head sail luffed over and over until she got the hang of it. When she finally learned how to keep Felicity “in the groove” the boat heeled nicely to leeward and Felicity sliced through the building waves one after the other.

“Wow! This is soooo … awesome!” I was happy to hear her say she was having a good time. “Say, John, could you put some lotion on my back? I can feel the sun on it. I didn’t do my back earlier.”

“Sure.” I said, and I squeezed some of her lotion on my palms and applied it to her shoulders and back. As I was rubbing the slippery lotion into her skin I became acutely aware of how good her young body felt and my cock started to act up again.

“Make sure you get some on my … ahhh butt … I ahhh … I don’t have much covering it.” She giggled as she said this.

I wanted to do as she asked but I also had mixed emotions given that she was my wife’s niece. However, my mostly erect cock that was straining against the material of my sailing shorts argued strongly for complying with her request.

“Ahhh … Sam, I’m not sure … I ahhh, should …” I stammered.

“John. It’s OK … you’re the one who pointed out that I’m an adult now. Please? I don’t want to burn.”

I sat down on the lazarette hatch cover right behind Sam and squeezed out a bit more lotion. Then I spread it over her beautifully exposed and exquisitely proportioned ass checks. She felt absolutely luscious and my hard-on was causing me pain, I was so stiff.

“Put some more on the back of my legs, too, please.”

“Ahh … alright.”

My hands slid down over her bottom and I rubbed more lotion on the backs of her thighs. My fingers moved up to the top of her legs and over her checks again and I thought I heard a little moan over the sound of the wind and waves.

“Another boat, John.” Sam exclaimed, pointing off to port. I could see it just under the foot of the jib. There was a very large motor cruiser blasting at full speed parallel to the shoreline.

“That’s OK … it will pass well in front of us … just hold your course.” I said. I continued rubbing the lotion in; long past the actual need to do so. My hands slid up her inner thighs, and once, my finger tips brushed the bikini that just barely covered her sex. She squirmed a little and I distinctly heard her moan then, but she said nothing.

A few moments later we encountered the motor yacht’s substantial bow wave. I must admit, I was too caught up with applying lotion to Sam’s sexy thighs and beautiful ass, so I didn’t think to warn her to hold on tight before Felicity’s bow suddenly reared up and then crashed down the other side of the steep bow wave. The next thing I knew, Sam was thrown on top of my lap. With one hand I grabbed her to keep her from falling on to the deck and with my other hand I grabbed the wheel that she was no longer holding.

“Oh geez! What happened?” She blurted out.

“Just a bow wave. It’s OK” After the big wave, the boat settled back to just bouncing over the regular sized waves.

Sam squirmed a little, but made no effort to extract herself from my lap.

“Are you OK?” I asked, genuinely concerned for her.

“Oh yes … John … and that feels so so good too …” Her voice tailed off, sounding very sexy and naughty at the same time.


“Your hand … ahhh … holding my breast … and … ahhh … I mean … there’s this big hard lump under me that is starting to make me very wet, John.” As she spoke, I felt her hips start grinding sideways and back and forth over my lap — over my hard cock, to be more precise.

In shock, I realized she was right. When I had reached up to help her avoid a fall, my hand connected with her firm pert breast. Conscious of it now, I marveled at how fantastic her sweet young form felt in the palm of my hand. I knew I should immediately let go. But I didn’t. Instead, I moved my hand so it slipped underneath the bikini top where I could gently squeeze her nipple.

“Sam, we shouldn’t do this.” I said, trying to be noble; but at the same time, I could not bring myself to relinquish my hold on Sam’s perfect breast.

“Don’t stop … John … please … it feels so nice …”

“Hold the wheel, honey …” I said, giving up any further attempts at propriety.

She placed both hands on the wheel, but she remained seated on my lap; grinding on my hard cock. I continued fondling her firm breast and taught nipple; then, with my other hand free, I placed it on the inside of her leg and moved up her thigh until my finger tips brushed the material of her bikini between her legs. Her bikini bottom was indeed soaked. I pressed the stretchy material and my finger tips were forced into the crease of her pussy lips. Then I started moving my fingers slowly up and down between her pussy lips through her bikini.

“Oh fuck!” She said breathlessly. “Ahhhhhh! Oh … don’t stop! Oh John!”

“I won’t stop, honey.” I knew that what I was doing was wrong, but I did not, could not, stop.

I let go of Sam’s luscious tit and used that hand to pull the string ties of her bikini top. Then I pulled the top away and dropped it on deck. Next, I untied both sides of her bottom. With my other hand, which had been rubbing her pussy through the bikini, I pulled the material away from the front and she was suddenly totally naked. she still sat on my lap and she was still steering the boat. Although, her steering had become somewhat erratic.

“What are you doing? Oh no … what if somebody sees me naked?”

“There’s nobody close to us.” I assured her as I inserted first one finger, then another, into her extremely well lubricated pussy. I moved in and out of her with one hand and my other hand reached around and cupped her right breast again so I could pinch her hard nipple with my fingers. She was moaning and letting out little yelps and pushing down hard on my lap making my cock desperately want to escape. As I worked my fingers in and out of her pussy, my thumb was able to cover and stimulate her clit. I could hear her breathing change to a series of gasps. I sensed that she was getting close.

“Oh John … I … I … I’m going to cum!” And she did. I didn’t stop my ministrations, so she came over and over again. I sort of lost count. There is nothing that excites me more than hearing and watching a woman have an orgasm.

“No more … please …” She said finally, sounding out of breath.

I pushed her bottom up off my lap so that she wasn’t so much standing as leaning over the wheel — hanging on for dear life, it seemed.

I quickly unzipped and pulled my shorts and briefs off in one swift move. I gently grabbed her hips and guided her back onto my lap. My swollen dick touched her pussy lips and I heard her yelp in pleasure. I used one hand to guide my cock to her wet opening. As soon as she felt the head of my member touching her there, she eased herself down on the length of my very stiff shaft.

I was in heaven.

The feel of her tight hot wet pussy squeezing my dick was better than anything I’d ever felt. Even Karen, when we were both younger, never felt so good.

“Oh … John … fuck me baby … fuck me!”

“You have to do the work … move up and down Sam … I’m sort of pinned here, honey.”

So she did. I got one arm wrapped around her so I could keep rubbing her clit, while the other hand kept her from going too high on the up swing. It wasn’t long before she had another orgasm. As she was screaming and twisting around — I think she had her eyes closed — I heard the headsail luffing loudly. Too late; the wind got behind the ginny and shoved the bow around so that we were soon heading back in the opposite direction. We were running down wind, but with sails set for beating to windward — very un-seaman like. But with that exquisite creature bouncing up and down on my cock, I couldn’t have cared less about re-setting the sails

That’s when I noticed the large ketch sailing towards us. She must have been behind us for a while and had gained steadily, but I had been too pre-occupied to notice. Now, we were closing with the other boat rapidly. Sam was hanging on to the wheel — not really trying to steer anymore — more like using it to keep from falling over after her last tremendous orgasm. I reached around her with one hand and turned the wheel as best I could to; 1) avoid hitting the on coming ketch, and 2) to try to let the sails catch a bit more wind so we didn’t just sit and rock back and forth in the waves and get seasick.

Sam was still moaning with delight but seemed to be coming back around when the other boat passed rather close to windward. Her skipper and crew started waving in the typical friendly manner sailors are apt to do when out on the water on such a nice day. But, then I heard a wolf whistle and saw one of the women on board the ketch point at us. A young guy in the crew made some apparently lewd remarks – I couldn’t really hear his exact words.

Sam looked up in shock. “Oh my gawd!” She made a feeble attempt to cover her naked breasts with both hands. To do this, she had to let go of the wheel — thankfully, I still had one hand on it. Without the wheel as support, her body came down hard on my cock on which she was still impaled. Maybe slamming down so hard caused my dick to hit her “spot,” or whatever, all I knew was that it kicked in the loudest most intense orgasm she’d had yet.

She screamed and started yelling, “fuck me … fuck me John! Oh gawd … fuck me harder!”

The ketch we had just past should have been out of ear shot by then, but I looked back briefly and saw heads turn as Sam shrieked in ecstasy.

Sam eventually regained her senses and just sat on top of me with my throbbing dick jammed as far up her sweet snug pussy as it would go. Felicity pitched gently as the waves coming from astern lifted the transom and then let it drop, over and over.

“Did you cum John?” Sam said in a raspy voice.

“Not yet.” I answered. “Are you OK … for a second there I thought I’d hurt you.”

“Oh no … you didn’t … didn’t hurt me. No, it was the best … I’ve never felt like … like that. John … I want to feel you cum inside me, John … please?”

“OK” I said. My balls were aching; I needed to cum, so she was getting no argument from me.

I pushed her bottom up off my lap and my cock slipped out with a little “pop.”

“Bend over … hold on to the wheel … steer, if you can.”

I stood up behind her. Her womanhood was presented to me and she was literally dripping wet. Her juices ran down both thighs. My cock swung up and down with the motion of the boat as I moved towards her luscious rump.

“Oh gawd John … hurry! I need you inside me again … I want your hot cum … now!”

I guided my member to her pussy lips and teased her with it; rubbing it up and down her slippery crease. Then, ever so slowly I pushed the head inside her and just held it there. Slowly, I eased in, more and more until my pubic hair was pressed against the soft round globs of her ass. I grasped her hips and pulled her tight to me; then I thrust just a tiny bit, and she gasped.

“Oh John … fuck me hard … I want it baby … really fuck me fuck me fuck me.” She yelled.

Never being one to deny a lady in need, I started slamming into her as hard as I could. One after the other … slam … then slam again … and again. Then I upped the pace. Faster. I fucked her with every ounce of energy I possessed and I felt my own climax building. My vision blurred and tunneled in on just her bare ass checks and on my cock going in and out and in and out and I heard the squishing of her pussy and heard the slapping of my balls against her with every thrust and then I exploded … over and over and over, until I was completely spent and exhausted.

As I came, she screamed in ecstasy too. Then I slumped over her back and held on to her tightly — my hands grasping both of her breasts — and I tried to catch my breath.

The thought, “am I getting too old for this?”, ran through my head. And it occurred to me that I had just fucked the bejeezes out of my wife’s niece — what had I been thinking?

Sam pushed up from her bent position, stood upright, and turned to face me. She lifted her arms and wrapped them around my neck and then she kissed me with both tenderness and passion. Her tongue darted in and out of my mouth, playing tag with my own tongue.

After who knows how long, she broke the kiss and said, “I felt it.”


“Your hot cum. I felt it inside me … I never felt that before. It was so special … each spurt as you pumped your seed inside me.”

“My gawd … you weren’t a vir…”

“No, Love, I’ve had sex twice before. But I made him use a condom.” She said. “Hmmm … in fact, John, I can feel your cum running down my legs right now.”

As she spoke the boat took a sudden lunge over to leeward. With no one attending the wheel, Felicity’s natural weather helm took her back around toward the wind and a gust had caught both sails pushing her over to nearly thirty degrees. We both nearly went over the side but I managed to get one hand on the binnacle and the other around Sam and saved us.

“Damn!” I said. Sam giggled — she seemed to think it was fun.

“I’ve got to get those sails down.” I told Sam. I quickly got the engine started. “Take the wheel and point into the wind and hold her there.”

I grabbed my shorts, quickly pulled them up without even bothering to zip, then I jumped up on top of the cabin and got both sails secured. When I returned to the cockpit, Sam was standing there steering — still naked. She was amazingly beautiful.

“Don’t you want to get dressed?”


“Why Not?”

“I want to do it again.”

I felt my cock stirring once more. So, I locked the wheel amidships — with the engine turning at low speed, it would keep us heading out into the Gulf, and away from traffic, without the wind affecting our course.

Sam came around from behind the wheel and pulled my shorts down. She knelt and took my soft but growing member in her mouth; she swirled her tongue around and over the head. As she started pumping her mouth up and down my shaft I became fully hard again.

She removed my cock and said, “Oh John … I never felt a man’s penis grow in my mouth before. That’s so … so … special. I love it!”

“You’ve sucked cock before?”

“Yeah. That’s one way you keep boys out of your panties.” She said with a naughty grin. “I want to taste your cum, John. That’s one thing I’ve never done. I never let a boy squirt in my mouth but I really want you to so I can taste it and swallow every drop. OK?”

All I could think to say was “sure.”

As we motored slowly away from shore, she gave me the most exquisite blow job and I did finally erupt in her mouth. A little bit of cum dribbled down her chin and some fell onto her chest, but to her credit, Sam did swallow most of it. When I was done she kept pumping my cock with both hands. I never thought I had it in me to climax twice inside an hour and still maintain an erection; but that was the effect Sam had on me that day.

“Wow. I love the taste and the feel of it hitting the back of my throat. Each squirt … and having my mouth full of you warm cum. It was beautiful.”

She wiped the bit of cum from her chin and licked her fingers. “Yum!”

Then she pushed me down onto the cockpit seat and straddled me and grabbed my still hard meat and shoved it up inside herself.

She rocked back and forth and lifted her hips over and over for what seemed like another hour; though I am sure it couldn’t have been so long. She had more orgasms — I’ve never encountered a woman like Sam who was so easily pushed over the edge. She was just amazing. And she was so vocal telling me how it felt having me inside her and how it made her tingle and feel dizzy. Finally, after who knows how many more climaxes, she sort of slid over to one side and curled up on the cockpit cushion without saying a word and was asleep. I had not cum again — gee whiz, wonder why … could it be I’m an old man? I’m certainly not a kid anymore but Sam sure made me feel like one again that Sunday afternoon.

I pulled on my shorts one more time and cranked the engine up to full speed and turned the boat back towards the marina. It took well over an hour before we were heading back into the marina’s breakwater. On the way back, I went below and found the pair of cut offs and Sam’s tank top were she had left them when she had changed into her bikini. I managed to get these on her while she slept so she wouldn’t be lying on deck naked when we got back to the dock. She sort of half woke up while I dressed her, but then drifted off again.

I pulled the boat into my slip and tied her up. Then I gently shook Sam awake.

“It’s time to go, hun.”

She looked up at me bleary eyed. “Huh?”

“You’ve been sleeping. We’re back at the marina.” As I said this, she wrapped her arms around my head and kissed me again. I had to push her away; there were people around who knew me and Karen and they would wonder what I was doing with a young girl passionately kissing me.

“Not here!” I said.

We packed up our stuff and took everything to my car. As I was pulling out of the marina parking area, Sam got on her cell.

“Hi mom its me. Oh Mom, we had such a great time … I got to sail the boat! It was fantastic. Oh … no. Uncle John is dropping me at Cynthia’s … she called while we were sailing and wants me to go over and spent the night at her place. It’ll be the last chance I get to see her before I go to school. Is that OK? Sure. Yeah, I’ll call in the morning … yeah, I’m sure she can give me a ride home so you won’t have to be late for work. Bye. Love you too.”

I asked Sam where Cynthia lived so I could drop her.

“I’m not going to Cynthia’s.”

“Huh?” I said, confused.

“You said Aunt Karen wasn’t getting back from Boston until Tuesday, right?”


“I want to sleep with you tonight. I want you to make love to me again and then fall asleep in your arms.”

“Sam …”

“Please?” She begged.

So that’s what we did. We went to bed right after dinner and I fucked Samantha for another hour or two. She wanted me to fuck her in every conceivable position. She told me that her previous two experiences with her boyfriend had both been missionary. Sam said it had been nice her first two times, but she wanted to learn everything; experience everything — she was insatiable.

When we did finally manage to go to sleep we were “spooned” – my front pressed to her back – and my cock was still inside her. I remember just ever so slowly moving in and out of her. The next thing I knew, it was morning, and I awoke with Sam’s mouth on my hard cock. Before I could get the sleep out of my eyes she was astride me and riding me like a bronco rider. She called her mom on her cell while I was still inside her, for heaven’s sake!

“Mom. Yeah, still at Cynthia’s. Listen, she wants to drive over to the mountains and go hiking. Yeah, I know … I’ll work on packing tonight when I get home. Probably late … I don’t know … we’ll be fine, honest … no, she’s lending me some of her cloths … I tried on a pair of her hiking boots and they fit fine. Geez Mom, I’m not a kid any more … well, the cell phone isn’t going work up there, you know that. You’ve been up there before. Yes … see you tonight. Late. I love you too … bye.”

All the time she talked she was grinding away with my stiff dick deep inside her. After her call, she just grinned a very sly grin.

“You’re something else, Sam.” And then I came inside her for the first time that second day. She lifted her hips off my cock and reached underneath to retrieve my cum as it dripped from her pussy.

“Hmmm … so yummy.” She said, licking her fingers. She repeated this several times, kissing me once in between to share the taste of the pussy juice / cum cocktail with me. I had to admit, it tasted pretty good.

We spent most of Monday in bed. We showered and fucked in the shower. We had lunch and she wanted me to fuck her on the kitchen table — so I did. I came three more times that day and by ten o’clock that evening I could barely walk. My pubic bone above my cock was sore from pounding Sam so much of the day. How she could take it, and still want more, was beyond me.

I drove her home late that night. She made me drop her at the corner so her mom wouldn’t see my car. She kissed me passionately, one last time.

“Thank you John.”

“For what?”

“For teaching me what it is to be a woman.”

I opened my mouth and was desperately trying to think of something appropriate to say, but Sam didn’t wait.

“I want to go sailing with you again next summer … just you and me again. OK?” And then she jumped out of the car and was gone.

Sailing with Sam never happened again. The following year I heard from my kids, who stayed in touch with Samantha, that she had signed on for a “semester at sea” program — she was double majoring in marine biology and oceanography.

But I’ll never forget sailing with Sam … for as long as I live.

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