Schooner Tales Ep. 01

This is my first story which I suddenly felt inspired to write a couple of months ago, and roughly 15 years after I first found literotica.com. The story took shape very quickly, in just a day or two, but I have left it to age since I first drafted it, reviewing and tweaking it several times, so I hope it is now fairly free from errors and typos.

I envisage this story being the first of several episodes, but if the drafts of other stories that I have started evolve into works fit for publication I don't expect them to be traditional chronological chapters, more a series of tales, each a stand alone story featuring the Captain of the schooner ("me" - the stories are written in first person) and Cassie, the first mate. I may add other recurring characters, but not all stories will feature Cassie in a major role, and indeed she only has a bit part in this story.

I am not promising when other episodes may be uploaded, they might be weeks apart, or longer.

As this is my first story, I look forward to comments, feedback, and constructive criticism.

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I was working as a schooner captain doing short cruises into the bay, raising the sails for a couple of hours and pointing out buildings, homes and islands of interest to tourists. These cruises ran throughout the day, and ended with a 7pm-9pm evening cruise, at which point we tied up the ship and went home. I had an idea that, in the more liberal times we live in, that there might be a market for couples night cruises, where we sail into the bay on warm summer evenings, drop anchor on the leeward side of one of the uninhabited islands for a couple of hours and enjoy a little wine or beer and the couples let their passions run free under the moon and stars.

I pitched the idea to the owners of the ship, but while they didn't want to get involved, they agreed to let me rent the ship for a late cruise, effectively splitting the revenue 50:50, so they made some extra profit and I pocketed a tidy bonus income. The owners would let me use fuel in the tank, and I would pay the ship's mate out of pay share. The ships mate is Cassie, she is Anglo Hispanic, Puerto Rican, I think, recently out of college, so early 20's, a little over average height, maybe 5'6", black hair, and generally slim, but maybe carrying a few extra pounds on her derriere, giving her a nice rounded ass without being at all overweight.

I knew that selling the idea to Cassie might be a challenge, or at least selling it to her boyfriend, Andy, so I suggested that he could come along too if he liked, any time he wanted, ... with the same benefits on offer once we had dropped anchor and the active participation of the ship's mate was no longer required.

I was able to find a few places to advertise these "romance cruises" on-line, and I booked four couples for the first cruise. I let Cassie know that we're in business, and that she should let Andy know, if he was interested.

The schooner isn't large and there isn't much room for privacy, but then it would be fairly dark out in the bay and by restricting numbers to four couples there would be one couple fore and aft on each side of the seats and hatches on the center line, so there would be room enough, and I assumed that mostly couples would respect each other's privacy. Cassie and Andy would be upfront in the bow area, and I would most remain at the wheel in the cockpit. Maybe I would stand up and lech a bit if things got interesting, but while a bit of voyeurism sounded fun, I didn't expect to spend too much time perving.

I wasn't sure who would respond to my ads - I was asking $200 per couple which wasn't expensive, but it was enough to price out most frisky college students, however soon discovered that the appeal of an amorous evening under the stars had a broad appeal, from couples in their twenties up to at least those in their fifties.

Then there were couples such as Steven and Claire, I would put their age different at around 25 years, her around 35 and her husband around 60. They were celebrating ten years of happy marriage, and looking for a memorable evening that was a bit different from just dinner and wine by candlelight. Clearly Claire had been a trophy wife, and to be fair to her, she still is, but married at 25 she had born Steve a son and a daughter, and had worked hard to keep her figure, and now, in her mid 30's was still a picture of womanly beauty.

As they came aboard I noticed that Steve was casually dressed in khakis and a polo shirt, carrying a bottle of champagne and plastic cups (no glasses are allowed on board). Claire was wearing a simple white shift mini-dress that showed off a considerable length of tanned, well-toned leg, and with almost flat white sandals, and carrying a small white clutch. They settled down just ahead of the cockpit, on the port side. Other unremarkable couples boarded and Cassie showed them to their part of the deck further forward and on the rear starboard side, on the other side of the mast from Steve and Claire.

As we set sail the couple all opened their drinks of choice and were soon happily kissing and cuddling, and by the time we had sailed across the bay and Cassie had dropped the anchor overboard, each couple was lost in their own world of passion, except for Steve and Claire, where things were, er, apparently a bit of a let-down, at least on the part of Steve. Steve and Claire had been drinking champagne, and cuddling, and the cuddling had given way to fondling and groping, but Steve was of an age where ED was an issue, and he was unable to perform. After a while Claire stood up, looked back at her husband and then slowly walked over to me where I was propped in the cockpit. I had been daydreaming and looking at the stars, as well as keeping an eye on the activities of the several couples on deck.

Claire stepped down into the cockpit, approached me and whispered in my ear. She pulled back and I looked at her, trying to decide if I had really heard what I thought I had heard her say. Her husband wasn't up to the task this evening, and he had told her to come and ask me to take care of her. With barely a moment's thought my expression went from puzzled to uncertainty, then she leaned forward again and nibbled on my left ear, her breath heavy on my neck. She paused, and then stuck her tongue in my ear wiggling the tip of her dainty tongue around in the folds of my ear, making it wet. It was a strange sensation, and not one I was used to, but I soon felt an involuntary tightening in my groin, followed by a swelling of my member.

Getting into the mood I placed my hands on her hips as her arms reached around my chest to hug me. My hands slid around to the small of her back and I felt her take a deep breath. She pulled back from the attention she had been giving my left ear, and looked me square in the face before leaning forward and gently kissing me. We held the kiss for a moment then we both relaxed our lips and our tongues entwined. Keen to keep things progressing I reach up her back to find the top of her dress's zip and I pulled it down; as did so I noticed that the dress was help in place with a hook and eye, which I unhooked, before lowering the zip through the small of her back and to it's end just above her rump.

We released our lip-lock and Claire stepped back to allow me to ease her sleeveless minidress off her shoulders, which then slid effortlessly to the deck. There she stood in nothing but a soft white bra and cotton panties, perfectly complementing the simple white shift dress that she had been wearing. She leaned forward against me and we embraced, and I took that as a sign that I should unhook her bra. She shrugged and the bra slid off her arms. My hands dropped and I hooked my thumbs in the waistband of panties and slid those down too, to join her dress and bra on the deck. Claire then stepped back, paused for a moment as if unsure, half-turned and looked back to where her husband still sat on the deck, watching his lovely young wife disrobing, as he sipped champagne. She looked at her husband and although in the near-dark his face appeared to indicated encouragement to continue, the shooing action of this hand left no doubt, that she should continue down the path she had started.

Claire turned back to me, barely an arm's length away, and apart from a pair of diamond stud earrings and the rings on her left hand, she was as naked as the day she was born. She was truly a thing of beauty - quite tall, maybe 5'10" with a toned figure, neither slim nor muscular, which she had clearly taken good care of, but still with sensuous curves in all the right places, modest breasts that were either a B cup, or a small C cup, and a trim flat stomach. She was the image of a woman at the height of her sex appeal - not a hint of girlishness but not yet at middle age when the effects of age gravity would start to take a toll on her body.

Claire stepped forward, emboldened by the encouragement of her husband just a few feet away, and started to unbutton my shirt, while I loosened my belt and with one swift movement dropped my pants and briefs. At this point I realized that it really was about to happen, and so did my penis, which resumed swelling.

Freed from our clothing we embraced again, and our bodies pushed together as we clutched each other. My member was now hanging heavy, but not yet fully rigid and as it rose it brushed against the softness of Claire's inner thighs, rising until nearly horizontal when it lodged under her lips. She could feel it, and as she wriggled, I could feel her heat and the moistness of her lips as her hips moved back and forth almost imperceptibly with the gentle rocking of the ship; my penis strained to find her entrance.

Claire lifted her right leg to give me more room, and flexed her knee to rest her foot on the edge of the cockpit where I was leaning, she then reached down to guide me in, and as she lifted herself onto the tip-toe of her left foot, the head of my penis found her slit and it started to slide home. Claire had born two children for Steve, so was no virgin, but exercising regularly her muscle tone was good and her vagina was snug and felt good. As I slid further in I supported her under her thighs and she slowly lifted her left foot, which left me supporting much of her weight, but her body pushed down, taking me further inside and all the way until her lips pushed against my crotch, and she placed her left foot on the edge of the cockpit behind me. Then she started to flex her lower back and lift herself almost imperceptibly with her legs, before dropping back and impaling herself on my engorged member. This continued for several minutes, and we could have perhaps both achieved great satisfaction in that position, but it was limiting and not exactly either comfortable or conducive to energetic fucking.

I took Claire's full weight and lifted her just enough to lift her feet, but not to free my penis from her moist depths. I turned her around and placed her ass on the deck, back from the edge of the cockpit, then supported her as best I could while she hung on and we laid back on the deck, her on the deck with me on top, my chest pushed against her flattened breasts. Released from supporting Claire my hands moved up to hold her rib cage, she still hugged me tightly, and wrapped her legs behind my ass, and crossed her feet to hold me in a lock. But now gravity was on my side and despite her hold on me I was able to flex and thrust firmly into her. Claire's breathing got heavier, and her skin became moist from the exertion. We kissed some more, and my tongue probed deeply. Our rhythm slowly increased heading steadily towards the inevitable crescendo - I pushed and grunted and she pushed back and moaned. The moistness where our genitals met had increased, make no mistake, we were now fully wet, and my penis was slick as it slid back and forth, and soon I would be adding my own contribution to the wetness.

I sensed a movement to my right and I saw Steve move around to get a better view as I pounded his wife towards a climax. His expression was one of interest and curiosity, to see what his wife looked like and whether she was, as he had earlier told her, enjoying herself fully. If this wasn't full enjoyment, I don't know what would be. I thrust some more, and she moaned some more, I pushed firmly grinding my public bone against hers, and pushing her towards her climax. With one last push I tensed, my thighs strained, and I pushed with all my might. At the same time Claire push too, she also tensed and flexed her spine, pushing her pelvis up one last time and then there was a roar and a guttural moan as we orgasmed together. I could feel the semen - one, two, three jets deposited deep inside Claire's twat.

We held for a moment, burning from our mutual heat and glistening with sweat. Claire still held me close and I could feel her chest rise and fall, but more relaxed now as we came down from the highest highs of human experience.

I could feel moisture and stickiness on my balls and mingled semen and Claire's juices ran over her asshole and dripped on to the deck. We broke our embrace and I rolled to one side; Claire slid from under me before leaning back to give me one last kiss. She dropped back into the cockpit to retrieve her clothing, which she casually draped over her arm before stepping back up onto the deck still completely naked and she took a couple of paces to where Steve sat, still entranced by what he had just seen, and what his wife had experienced.

As Claire retrieved her clothes I tore a piece of paper towel from one of the rolls positioned around desk for the purpose cleaning up afterwards and wiped my penis and dabbed at my public hair, but Claire was still enjoying the moment, of nakedness on the deck, the warm breeze on her skin, and was oblivious that she was still dripping on the deck, and then on her husband's pants where she stood over him. Steve took a piece of paper towel himself and reached up to wipe the semen and juices from his wife's pussy. Without thinking he put the towel to his face and inhaled - recognizing his wife's musky scent, but this time mingled with the smell of my semen. As Claire stood over her husband, he put his arms around her thighs and pulled towards him, his face at close to crotch height, and he pushed his face into her pussy and licked at her lips, not realizing that he was about to inflame her passions again.

Claire shivered and gasped at the sensation as her genitals, still flush from fucking and coated in dried juices started to prepare for more activity. She grasped the back of Steve's head and pushed herself against his face, then bent her knees slightly and thrust her hips against him, oblivious in the heat of the moment to his difficulty in breathing as she used him for her own pleasure. Steve used his tongue and Claire again started to moan in response to Steve's vigorous licking along her slit and over her clitoris, and he didn't seem concerned at my semen oozing out of his wife, at least not enough to stop him doing his own bit to pleasure his wife and make it a memorable evening for her.

As we returned to the quay, Steve and Claire hugged and kissed, but she remained naked. I am not sure if it was for her own pleasure, to titillate her husband, or to tease me with the sight, and smell of her womanly perfection.

As we reached land Claire slipped her sandals back on, grabbed her clutch in her left hand, draped her dress, bra and panties over her left arm, and looped her right arm around Steve's waist as they walked off the quay, and through the gate into the parking lot, all the time Claire was still stark naked.