Caution: This Sex Story contains strong sexual content, including Ma/Fa, Consensual, Romantic, Heterosexual, Cheating, Oral Sex, Anal Sex, Masturbation, Exhibitionism, .
Desc: Sex Story: Chapter 1 - Struggling to make a living on his own, a sea-loving young man sinks all his worldly worth into a small cruise boat. He lucks into chartering the vessel to some wealthy ladies, who become very generous clients - along with two of their daughters.
"Ahoy, the Lady A. Are you Captain Cook?"
I turned to the dock to see who was hailing me. The voice came from a woman, probably in her late forties or early fifties, dressed in what appeared to be upscale tan shorts, open white blouse over a tan tank top, deck shoes and a broad-brimmed straw hat covering shoulder length brown hair with a smattering of silver. With the late morning sun behind her, I couldn't really see the details of her face.
"Yes, ma'am, I am," I responded.
"Is your boat available for hire today?"
"Yes, ma'am, it sure is," I replied enthusiastically.
It had been several days since I had a charter and I was in need of the money. I loved my boat but it took everything I was able to raise to keep it going. I had purchased the 58' 6" catamaran at the end of last season, sinking every penny of a nice inheritance, all of the proceeds from the sale of my small house and still signing a sizeable mortgage. I figured I could make ends meet by working the winter season in the Caribbean islands and the rest of the time in the more affluent resort areas of the northeast states. Still, things had been slow so far and I was glad to get a charter, even if I had to drop my standard rate.
"Good," she replied with a smile. "Consider yourself hired."
She stepped on the gangway, intent on coming aboard. I leaned my mop against the cabin and hurried to the gangway, offering her my hand although she walked steadily down the short access. She almost jumped the last couple of feet, laughing as she landed in my arms. For the first time, I could see she was a strikingly pretty woman.
"Thank you, Captain," she laughed, quickly disengaging herself from me. She put her hand in mine for a quick handshake and said, "I'm Eleanor DuPont."
Noting the ring on her left ring finger, I said, "Very nice to meet you, Mrs. DuPont. Let me show you around." I pointed her toward the four steps down to the main salon. "Will anyone else be joining us today?"
"No, it's just me," she said. "I need a relaxing time to rest and a quiet sail is always relaxing to me."
"Okay. Any particular destination or shall I make the choice?"
"You pick it, Captain. My only requirement is that we get a great view of the sunset this evening."
I showed her four of the five cabins, omitting the one I used in the rear of the right hull. I suggested she take the master stateroom when she wanted to rest below decks and she left her large bag on the bed.
Back on the main deck, she checked out the cushioned bench seats around the aft portion, as well as the various comfortable seats around the pilot area and its opposite side. I pointed out the mats on the sun deck in case she wished to take advantage of the wonderful sunlight we were sure to have. She seemed very pleased with the layout of the boat and its cleanliness.
"I need just a few moments to set our course. Would you like something to drink? I have fresh coffee, orange juice and apple juice. Of course if you'd like something stronger, I would be happy to get that for you."
"Hm, I think just an orange juice, if you please," she answered with a smile.
"Yes, ma'am. Be right back."
I hurried back to the salon and opened the bar fridge. I poured a glass of juice, picked up a freshly ironed linen napkin and took them up where she was sitting on one of the benches.
"We'll get underway in about five minutes. We'll use the motors to get out of the harbor and then raise sails and cut off the engines until we get back to harbor tonight."
"That sounds good, Captain."
Turning to the pilot station, I set the computer to calculate a ten hour sail, since sundown would not be complete until after nine o'clock at this time of year. The course it set was triangular with a relatively short second leg and allowing for a fairly strong wind on the homeward leg.
On my way to the gangplank, I stowed my deck mop and cleaning gear in a locker and pulled in the short plank. At each of the fore and aft cleats, I pulled on the mooring lines until I could flip them off their cleats, then pulled in the lines and stowed them.
Back at the helm, I shifted to reverse and revved the engines just a little to back out of the marina. Once clear, we turned and followed the buoys along the traffic pattern to clear the little cape that provided some weather protection to the harbor. Soon we passed the breakwater, heading east into the ocean.
For more than an hour, she sat on the same bench sipping the juice. I went back and asked if she would like some lunch but she declined, saying she needed to watch her girlish figure, laughing at herself. I almost told her she didn't need to do that because I would watch her figure for her but decided I might offend a potentially good customer.
When I went back to the pilot station, she went downstairs, only to reappear twenty minutes later, barefoot and wearing a beautifully filled-out white bikini. She climbed the four steps to the sundeck and selected the mat on the starboard side, furthest away from the pilot station. However when she lay on her stomach, I couldn't keep my eyes off her slightly broad-beamed bottom, well rounded and firm and oh so inviting.
It didn't take long for me to have a raging hard-on. Nor did it help when she turned over to toast her other side after a half hour. Because of the shifting of the sun, she moved to a port side mat almost directly in front of me to catch more of the sun away from the shade cast by the sails.
The top of her bikini was well filled and well rounded and the view between her legs left little to my imagination with such a small patch of cloth covering the gateway to her delights. I couldn't see her eyes for the dark shades she wore but wondered what the smile that curved her lips represented. I had to duck my head and keep my gaze from her to keep from attacking her. With the boat on autopilot, I just pretended to be occupied sailing the vessel.
When she gathered her towel and book after another half hour and made her way back downstairs, I seemed to be studying the electronic gauges and working the wheel, even though my actions had no impact. I couldn't help but look up at her as she came down the steps.
She smiled at me and asked, "Would you show me how you handle such a large boat by yourself, Captain?"
I went through a short discourse on what each of the controls and gauges were for, showed her how to read our heading and use the wheel to keep it steady.
"Would you let me steer for a bit, Captain?"
"Certainly, Mrs. DuPort," I replied surreptitiously
I flipped off the autopilot and started to move out of the Captain's chair.
"No, no, stay right there," she teased. "I just want to try it for a few minutes to get the feel of how she handles."
I groaned inwardly because, although there was room for her to squeeze between me and the control panel, it would not be without our bodies touching. But before I could reply, she had scooted between me and the wheel, her bottom brushing my crotch all the way. I felt the round mounds of her buttocks pressing against my jewels and quickly my cock was again the raging erection I had worked so hard earlier to quell.
She took hold of the wheel as if she had experience at sailing and although she let it drift a couple of points to port, she soon corrected it and had us back on course. I could have sworn she wiggled her bottom a couple of times unnecessarily but I must have been mistaken.
She pressed herself backward into me and turning slightly, asked, "Is that for me, Captain?"
"Uh... well, I..." I stammered.
"Speak up, Captain. Don't be bashful. If it is, I'm flattered."
"Well... yes, ma'am."
"Good! I like still being able to do that to a man. So," with two quick moves of her hands, both pieces of her bikini floated to the deck and she rubbed her now naked body against me. "I think we need to do something about your condition, don't you, Captain?"
I groaned. I could just see my charter fee going out the window when we got back to shore and she complained that I had forced myself on her or something. Even the threat of a formal complaint and I would have to forego my fee. But the head on my shoulders was not in control.
I unfastened my shorts and pushed them to the deck, kicking them out of the way. My straining penis slapped her butt and she laughed, squirming, feeling it settle between her legs as it pushed down. She leaned forward, pressing her boobs against the wheel, offering her bottom to full advantage in the confined space.
I carefully worked my tool back and forth in the spreading moisture and my inflated arrow found the opening to her soft pussy, slipping inside. She was rather tight for a married woman and it took me several thrusts to get my whole rod buried inside her. It was a fantastic feeling.
She leaned back, pressed into my form from knees to shoulders and said, "Oh, my, Captain! That feels so good!"
"Yes, ma'am, it does."
"And please don't call me ma'am or Mrs. I like to be called Ellie."
"Yes, ma'am... uh, Ellie. And I'm Tom."
"Good. And Tom?"
"Please fuck me long and slow. Make it last."
I bent over and kissed her neck just below her right ear. She leaned her head to the left, offering that pretty tan neck for my use and I took advantage of it while starting a slow pumping motion of her pussy. The confined space kept me to short strokes and constantly reminded me to go slow.
Several minutes of magnificence sliding in and out of her velvet receptacle had passed when she looked over her shoulder and said, "Tom, I think you should reengage the autopilot."
I felt like an idiot but reached over and flipped the switch allowing the computer to take over again. Then I slid both hands up her sides, over her stomach and cupped her generous breasts, finding her nipples hard and proud. For several minutes, I kept up my slow short strokes while my hands kneaded her tits, pulling on her nipples, all to the soft moans of a lustful woman.
I slid my right hand down over her stomach and into the valley between her legs. My middle finger found the top of her crease and eased inside, teasing her clitoris and a few moments later, she hissed through clenched teeth, "oh... oh... oh... oh... oh, yes, Tommy! I'm cumming!"
I held her closely until the waves of pleasure coursed through her body. Then carefully I backed out of her, turned her around and straddling the captain's chair lifted her back onto my spear. I planted my lips on hers and was delighted when her tongue charged into my mouth. Holding on to her magnificent ass, I lifted her and let her fall back onto my pole over and over until at last we both came just a few seconds apart.
Afterward she clung to me for a long time before she finally pushed back enough to look in my eyes. She was smiling as she said, "Captain, I think I just got more than I bargained for today. That was incredible."
"Yes, it was, Ellie. Thank you."
"I think I should be thanking you."
"Well, how about we just say it took both of us to make some fantastic feelings today and I'm glad I met you."
She nodded and planted another big kiss on my mouth.
She put a hand between her legs and brought it up, wet from our combined juices oozing out of her. "I'd better get a towel," she said.
Ellie hurried downstairs and was back in a few minutes with a towel in hand to wipe the cum from my chair. She was still naked and there were streaks of cum running down the inside of her legs.
When she noticed me staring she said, "I like the feel of it, honey. If you don't mind, I'm not going to put any clothes on just yet. It feels good to go au natural out here where nobody else is watching."
"That's perfectly fine with me," I said. "And I admit I like knowing that it's partly my cum running down your legs."
She laughed and hugged me. "You know it's been a long time since I felt like this."
"Oh? Don't you and your husband do it anymore?"
"Oh, sugar, I thought you knew. My husband died over two years ago."
"I'm sorry, Ellie, I saw your ring and assumed..."
"That's okay. John had a stroke nearly four years ago and our lives after that were not what you could call normal. There was no sex after the stroke and precious few outings of any kind."
Ellie sat on the short bench facing the pilot station and we sat for a time just enjoying the fresh salty smell of the ocean air. I found I couldn't keep my eyes off her for long. Nor did she seem to keep her eyes from me. It seemed like she spent half the time looking at my face and the other half looking at my crotch while occasionally licking her lips.
On impulse, I rose and quickly crossed to the bench where Ellie was and I sat beside her, pulling her into my arms. She did not resist as I planted a spit-swapping kiss on her pretty mouth and our tongues were soon entwined in first her mouth and then mine. Both her hands went around my neck but then one stole down between us and began to rub my growing cock.
Unsteadily I picked her up and carried her downstairs to the master stateroom, where I placed her in the middle of the queen-sized bed. Then climbing into her saddle, I kissed my way from head to toe and back and then fucked her again when she begged me to enter her. We tried several positions, all of them good, while she had three orgasms and I filled her pussy with another load of cum. Afterward she pulled my head down between her breasts and held me tightly for a long time.
I felt the autopilot shifting the sails and turning us in a southerly direction so I got up to go topside to verify that it made the right course corrections.
Ellie suggested, "How about I make us something to eat?"
"I'm supposed to do that. It's part of the charter."
"Well, let's make an exception today, okay. I feel like being domestic. Will you trust me with your galley?"
I laughed. "I think I'd trust you with anything I've got. If you want to do it, help yourself. Anything there is fair game."
So as I went up to the pilot station, she went into the galley. Just as I knew it would, I found the computer had us right on course and moving swiftly. We were heeled over slightly to starboard but it was still quite comfortable on the big cat.
Forty-five minutes later, I was relaxing in the Captain's chair when the whirring sound of the winches brought me fully alert. I never tired of watching the electronic gear sail the boat without a hand touching it, once it was set. Now, with the wind almost directly behind us, some of the smaller sails were furled and the spinnaker, with its big red, white and blue vertical stripes went up like a balloon and we seemed to just skim over the moderate sized waves.
We had hardly settled on course when Ellie called me into the salon to eat. She had grilled steaks, tossed a salad and baked potatoes in the microwave oven, indicating to me she knew her way around a small boat's galley. Although mine was bigger and better equipped than many, it still would challenge many cooks who were unused to working in such a confined space. However, this food was superb.
I insisted she let me clean up after we ate and she didn't argue the point. Actually, with a big dishwasher and a trash compactor, it wasn't all that difficult. By then it was early evening and the sunset was still over an hour off but the sunlight was turning the sky all kinds of beautiful hues of red and orange and yellow. I escorted Ellie to the sundeck where we relaxed in the two forward lounge chairs with the last of our wine from dinner.
We watched the sky as if it were a movie and savored the moderate breeze. The sun was leaving the last red streaks across the western skies when Ellie turned to me and asked, "Would you like to play around again?"
I jumped down to the pilot station and verified our position... just a few miles from the mouth of the harbor. I reset the autopilot to furl most of the sail and just keep a minimum headway, verified that all running lights were illuminated and then hurried back to Ellie. She welcomed me to one of the sunning mats with open arms.
I spent several minutes kissing and touching her all over before I slithered down her form and buried my face between her legs. Although she had a strong aroma and taste of our former sex sessions, it was still a heady taste and smell to my sex crazed brain and I feasted on her wonders.
Soon Ellie began to have a series of mini-orgasms whose output just added fuel to my internal fire. I kept eating and kept being rewarded with just enough fresh output to whet my appetite. Occasionally I heard the horn of a passing vessel sound as they moved along faster than us and each time I would pop my head up to take a look and ensure we were not on a collision course. Something about being outside, in the openness, naked with a very desirable woman added to the wantonness of the act, even though the passersby could not really see us. At best, they could see outlines of people in the bit of moonlight that shown through the clouds every so often.
I dropped my head back to my sweet task and was finally rewarded when Ellie clamped her legs around my head, used her hands in my hair to pull me tightly into her and moaned and shivered through a more fulfilling climax. Only when it had passed and she had relaxed again did I climb up into her saddle and pierce her with my throbbing erection. I took time to ravage her mouth and her breasts and then set about fucking her harder and faster than earlier in the day.
Ellie responded with encouragement to the more animalistic pace, telling me to "pound my pussy, Tom" and "fuck me hard, honey" while covering me with kisses. I felt my balls contract and knew I was going to climax before her, sad because I didn't know if I could keep going until I got her to peak again. As it turned out, the splashing of my hot cum into her slick wet pussy must have been what she needed because she came maybe a minute after me and just before my legs collapsed from the adrenaline burn.
We lay together a little while before I said, "we'd better dress and get into port before someone discovers us."
She laughed. "And what would they do if they did?"
But she went downstairs with me and dressed in the same outfit she wore onboard that morning while I put on my shorts and shoes. Back at the pilot station, I took control, lowering all sails and turning on the motors for the final approach into the marina.
Just as I hooked the second line to the pier cleat, Ellie met me at the gangway holding out an envelope.
"I think this will cover the charter, Captain," she said with a smile.
I took the fat envelop and opened it. Inside was a stack of $100 bills. I flipped through them quickly and without counting, knew this was more than my charter fee
I protested, "Ellie, this is way too much."
She leaned into me and whispered, "Listen, I'm a rich woman and I'm used to paying well for quality services. Today's cruise was beautiful, just what I needed. Don't EVEN think I'm trying to pay for the fun we had. That was just between you and me and I loved it but I'm not about to start paying for it now. Okay?"
I stared into her eyes, trying to decide what would be the right thing to do. She looked so sincere that I folded the envelope and put it into my pocket. "Thank you," was all I could say.
Nimbly, Ellie scampered up the gangway to the pier. After a couple of steps, she turned and called back, "Book me for the same time next week, okay, Captain?"
I nodded, waved and watched her skip away like a schoolgirl.