Caribbean Cruise

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Rick takes Ashley, her father tells him a secret.
6.2k words
4.52
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Part 1 of the 9 part series

Updated 10/19/2022
Created 06/21/2004
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Rick Chaplain was one of those All-American boys; dashingly handsome, intelligent, and witty, with short-cropped dark brown hair, piercing blue eyes, and a rough, matured, attractive face that was weathered and appropriately tempered by the elements. He was originally from Patton, Ohio, a small town in the middle of nowhere, and had learned from a very early age how to make his own fun and get his own level of enjoyment out of the most bleak and disheartening of circumstances.

Having been discovered by a local oddity, a drunken ex-NFL superstar-turned-talent scout, – who saw potential in the young man’s football skills that few others imagined – and through his own passion to succeed at everything in life, Chaplain wound up on UCLA’s vast, formidable college football team, proving his worth against some of the best and brightest young football prodigies from all over the United States. It was there, when he was just 23-years-old, that Rick met and fell in love with 21-year-old Ashley Collins, a gorgeous, buxom blonde cheerleader with an I.Q. of 190 and a body to die for. She had a sexy, voluptuous physique with a nice round, meaty ass and a real big, firm pair of 34D-cup hooters.

It wasn’t much intentional that he fell in love: Rick knew it was fated to be, and he thanked God every single day for having Ashley in his life. She was beautiful, kind, generous, sincere, and loved to laugh. She made Rick smile just by being with him, and every time she wasn’t by his side made his heart ache with longing. Their sex life together was the best Rick had ever know…full of passion and tenderness, fire and ice, a perfect blending of extremes that he could never in all his years that he lived imagine tiring of.

They had been dating quite seriously for the past 3 years now. In the summer of the third year of their relationship, Ashley invited her boyfriend Rick to join her on a little yacht excursion to the Caribbean, which was a gift from her and her two sisters to their parents for their twentieth wedding anniversary, and he had readily accepted the invitation. He was now 26-years-old, and she herself was 24. He was a rookie for the Dallas Cowboys NFL team, and she was a student teacher at one of the local high schools.

The fifty-foot catamaran must have cost a small fortune to rent out for an entire week, but then Ashley’s father, Andrew ‘Andy’ Collins, was an extremely rich man, making his fortune by investing in some sort of oil scheme quite a few years back. Andrew was 55-years-old, and formerly a U.S. Navy SEAL, Ashley told her lover Rick. The guy was a nice enough fellow, or so Rick found, but there was an underlying tension between them… Rick believed it was because Andrew suspected he was ‘putting it’ to his middle daughter, Ashley.

His wife, Billie, was actually Ashley’s stepmother, but they got along like Mom and daughter. Ashley hadn’t known her birth mother; she had died when she was only a baby in a tragic skiing accident, so Billie was the only Mom she had ever truly known.

Billie was actually the mother of Andy’s youngest child, Ashley’s half-sister Constance. Billie looked young enough that Rick had logically thought she was one of Andrew’s daughters the first time they’d met, not his second wife, but she was in fact 38-years-old. She was a lot better looking than Rick could believe, and he found himself becoming bewitched with her physical splendour every time he was in her presence.

She and her daughter Connie looked much more like sisters than a mother and daughter. They both had dark tans and golden-blonde hair, and wear their hair in the same short, pixie style. Connie was slightly taller. Her mother was a lot fuller in the chest and hips, and of course looked older in the face. Billie had a full, luscious pair of 36DD-cup breasts, which Rick found so alluring and very hard to resist, despite the fact that he loved Ashley with all his heart.

Connie was just 18-years-old, and had a tall, lithe body full of femininity and sensuous delights. Rick found himself drawn to Connie as well as her mother because she was so young and tender, so innocent, so gorgeous in her naivety. Perhaps it was the fact that she was so young, and so inexperienced with the ways of the world, that Rick felt an overwhelming urge to be there for her, to protect her and guide her, just like his girlfriend Ashley did.

She had a firm, taut ass, and long, sleek legs that were toned from daily runs and exercise at gyms. Connie had smallish, cone-shaped 36B-cup tits, but these only seemed to lend to the rest of her youthful, feminine sensuality, which Rick found helplessly erotic. She was the only Collins woman without a date for the cruise, but she seemed to have attached herself almost desperately to Ash and Rick.

Then, there was the eldest daughter, Kimberley, who was 27-years-old. When measuring the Collins women on their physical beauty, Kim Collins would win hands-down every single time (though Billie was definitely very close behind her eldest stepdaughter when it came to looks). She was a tall, gorgeous Amazon warrior-woman, one of the most erotic and intimidating women Rick had ever encountered in all his years. She had a voluptuous figure which she liked to flaunt at every opportunity, wearing the skimpiest of bathing suits and at times flashing her ample 38C-cup bosoms or moist, wet gash when the chance arose, which never failed to bring a smile to Rick’s face or get his meat-stick all hard and aching.

Kim and Ash’s mother had been half-Cherokee Indian, so they both had that genetic trait coursing through their veins – with Ashley, it was not all that evident, as she had inherited much of her looks from her father’s family, but with Kimberley it was quite apparent. She was very much her mother’s daughter, and had the silky-smooth skin and the darkened complexion of the Native-American Cherokee. She also had her half-sister Connie’s obsession with exercise, as she always had to run and do push-ups every morning before the sun rose up too high in the east. With long, billowing jet-black hair, piercing emerald-green eyes, and an achingly sweet, feminine face, Kimberley was the best of both her parents, and seemed to be the living continuation, as it were, of her and Ashley’s mother, who had died all those years ago.

She and her husband, Keith Stevens, were not getting along all that well as of late for some reason which neither party wished to share with the rest of the company. Rick could smell some serious marital problems in the air, and wondered to himself why they would even come of the holiday with everyone else if there were some serious problems between them. Keith at least should have stayed back on shore, so at least the entire Collins family could be together at this special time and have some fun. But their issues were now affecting the entire group, and there was little anyone else could really do to rectify the situation.

On the first day of their holiday cruise around the Caribbean, they had just sailed around a number of pristine island inlets, heading away from the more popular, crowded islands and shipping lanes to try and find their own little piece of paradise to enjoy. Rick and Ashley spent much of the morning sleeping off their long flight down from Miami, seriously jet-lagged and just happy to have finally reached their destination. But when they finally awoke, Ashley was feeling a little bit amorous, and was looking for a good long servicing from her personal sex-stallion, Rick…

Both he and Ashley liked to sleep in the nude, so there was no clothing to impede her access as she moved up against her lover’s naked body, rubbing herself up against his side. She slowly, laboriously slid her wet, dripping moot up and down Rick’s right thigh, leaving a long, glistening trail of pussy-juice down his leg. She then reached for her boyfriend’s right hand and, slowly grinding her pelvis now up against her handsome lover’s body, guided it down to her gaping cunt-slit.

It was at this moment when Rick came out of his deep slumber into semi-consciousness, to find his right hand buried in the pink, fleshy folds of his girlfriend’s dripping, super-sensitive snatch. He began to slowly work one cum-slick finger into the inner depths of her ultra-tight twat as he became more alert and began to realize what was going on, driving and gyrating the piercing digit into the very deepest recesses of Ashley’s body, causing her to grasp and arch her back against his probing with pleasure. Then he pushed in a second finger, working it in around her tight pussy with the first digit til Ashley was grasping and hollering with lust.

Rick moved slowly down until his face was level with Ash’s gaping gash, then he went in for the kill with his mouth and tongue, licking and sucking at his girlfriend’s budding, blood-red clitoris with a passionate relish. Opening his mouth to engulf his lover’s thick, throbbing love-button, Rick sucked back on the fleshy nubbin with all his might, causing her to scream with ecstasy as she came with a sticky flourish all over his face.

While he kept working his fingers relentlessly in and out of her sopping wet cunt, mercilessly finger-fucking her pink pussy as Ash orgasmed, Rick drank back her potent sex-sauce with the need of a man parched with thirst. As she kept squirting creamy pussy-juice into Rick’s wide-open mouth, he began to work his tongue up into her tight, hairy smoo, lapping at the inner folds of her vulva and scooping out Ashley’s girly-cum for himself.

He pulled his probing fingers out of her twat, licked and sucked the digits back into his mouth to get the sweet, savoury vadge-lube, then stick the two fingers back up her snatch again. This made Ashley screech at the top of her lungs with pleasure, as Rick filled her cunt-hole with his probing digits while licking and sucking at her sensitive clit at the same time. The sensory overload was, to Ashley, nothing short of exquisite…

Rick’s stiff, throbbing 8” cock was sticking straight up towards the ceiling, the mushroom-shaped, bulbous head, swollen with blood and light purple in colour, covered with glistening pre-cum, which was literally pouring out of the tiny little piss-slit at the top of his dick-knob. It was 8” of thick, rigid, circumcised dick-meat, quite an impressive specimen of the male form indeed… Rick was more than a little proud of his big, fat dick, and knew that it had rocked the world of every single lover he had ever taken to bed. In the end, he knew, they all fell in love with his massive cock, and went weak at the knees imagining what his throbbing phallus would do to their tight little snatches.

Ash noticed her boyfriend’s erection after finally coming down from her huge, mind-blowing climax, and quickly moved around and down between Rick’s legs to take his throbbing, blood-gorged pole of man-meat deep down the back of her throat. With little to no preliminaries required or necessary, Ashley Collins began to deep-throat her lover’s penis, using a good deal of spit to get his pulsating prick all lubed up so that it could slide in and out of the depths of her throat with more ease. As she sucked and slobbered on his phallus, Rick groaned with deep, pure animalistic lust, arching his head back and squeezing his eyes tightly shut as wave after wave of incredible pleasure coursed through his entire body.

She had a lovely mouth… Rick had never known anybody who could suck cock as well as Ashley could – she seemed to have developed the technique perfectly, honing it down to a fine art. Rick didn’t particularly want to know how exactly Ash became so good at slurping at his dick, but she was definitely very capable when it came to cocksucking…

Ash seemed to have no bounds when it came to sex, willing do whatever it took to bring the most intense pleasure to Rick when they made love. Every time they were intimate together, it was a new and vastly enjoyable experience for him, and Rick only hoped that he could make Ashley feel at least a tenth as good as what she made him feel.

“Oh Goddamn… ah baby, yeah, suck my dick just like that! Jesus, you’re so fuckin good at that, Ash!” Rick cried out, grasping two good handfuls of her long, billowing blonde hair and forcing her head down on his rigid tool. Soon enough, his ball-sacs were beating a regular tempo against Ashley’s chin as Rick fucked her throat with his cock. Finally feeling his pleasure reaching its zenith, groaning with lust as he felt his orgasm began to come rushing down upon him, Rick quickly pulled his cock out of Ash’s mouth and hurried wanked his dong with his right hand.

Ashley Collins let out a moan of lust, sliding over onto Rick’s right leg so that he could pleasure her meaty smoo with his foot as she licked and slurped at his cockshaft, then she spat a thick, gooey blob of saliva onto the very tip of her lover’s rigid staff. Following this up by moving down to take first one of Rick’s ball-sacs, and then the other, into her mouth to suck upon, Ashley then moved slowly up to lick a long trail up the underside of her boyfriend’s turgid, throbbing dick-stick with her tongue. Rick let go of his cock and allowed his woman to take back control of proceedings, giving himself over to her sensuous oral ministrations.

This time around, Ashley concentrated upon the bulbous head of Rick’s prick, using her teeth and suctioning mouth to pleasure her love’s manhood. She looked up at her hunk with wide, luscious eyes, savouring the look of pure bliss that was plastered all over Rick Chaplain’s face at that very moment. He could hardly believe how good it felt to have Ashley biting lightly down on his swollen, ultra-sensitive cock-knob, while at the same time she was licking and slurping at the tiny little pee-opening on the very tip of his hardened member.

“Oh Jesus, yesss!” Rick groaned out loud, rolling his eyes back in climactic pleasure as waves of pure orgasmic ecstasy coursed through his system.

Ashley then pulled her lover’s penis out of her mouth, and moved down under his balls to take a swipe at Rick’s brown, puckered asshole with her tongue. Rick let out a mighty roar of lust as Ashley took another long, sensuous lick at his butt-hole, causing him to shudder and thrash about with agonized pleasure. Then it really got interesting when Ash pushed into her lover’s tight, puckered little bunghole with her tongue…

Rick had never truly imagined that sex could ever be as incredible as what he was feeling at that very moment as Ashley Collins pushed into his tight brown butt-pipe with her tongue. He felt her thin, probing tongue sliding up against the walls of his anus as his rear-end gave in to his girlfriend’s determined probing, and soon he was arching his back and letting out a long, contented, protracted sigh of sexual ecstasy as Ash’s tongue finally worked its way into the very depths of his tight, constrictive bunghole. She had as much of her tongue as she could in Rick’s asshole, and it was one of the most intense, exquisite feelings he had ever experienced in all his years alive.

It was something that Ash had never done to Rick before, but he had certainly done the same thing to her many times in the past, especially when he was about to have anal sex with her, which required a lot of lubrication… she had quite obviously liked the experience when he had licked and tongue-fucked her tight asshole, so Ash seemed to have decided to return the favour in kind. He had ever even imagined that his anus could be such a pleasurable, orgasmic orifice.

Deciding now was the best time to fuck his lover, because he did not know how much oral stimulation he could actually bare in the intensely aroused state he was in, Rick reached down with both hands and cupped Ashley’s gorgeous face gently. He looked at her face with tender love and warm emotion, and then slid the thumb of his right hand into Ash’s mouth, which she instantly began to suck upon without a word of encouragement needing to be spoken.

“Are you ready to have my cock inside you now, baby?” Rick asked his girlfriend in a soft, cooing voice. Ashley smiled broadly and nodded her head, acting all innocent and well behaved, which brought a smile to Rick’s lips as well. He shook his head as his grin widened endearingly, then wormed his way back on the bed, away from Ashley a little bit, allowing her to crawl forward until she had positioned herself just over the top of her lover’s rigid, upthrust dick-staff.

Ashley was in the standard ‘cowgirl’ position, facing Rick as she lowered herself down onto his turgid dick-stick, impaling herself down upon his rock-hard cock. It was an incredibly exquisite feeling to have his dick swallowed up by the fleshy folds of Ashley’s moist, pink vulval lips, and Rick let out a soft, sharp grunt of pleasure when the swollen head of his throbbing phallus popped in past the outer ring of his lover’s cunt-hole. Ash then rapidly slid herself down the length of Rick’s granite penis, until pelvis was mashed against Rick’s and his twitching dick was buried to the very hilt inside her tight, wet pussy.

Grunting and grasping softly as wave after wave of intense sexual stimulation coursed through her body, Ashley felt a huge orgasm pour out of her within moments of being fully penetrated by Rick’s cock. She reached down with her right hand, keeping her body propped up on top of Rick with her left arm all the while, and rapidly frigged her own budding clit through the thick, well-trimmed bush of triangular, razor-thin blonde pubic hair, magnifying her own pleasure ten-fold as she bounced up and down on the length of her boyfriend’s erection.

After a while, she started to rock herself backwards and forwards on Rick’s rigid cock when Ash had his hardness buried deep inside her dripping gash. Grinding and gyrating herself around on Rick’s cock, Ashley used every trick there was to give herself and her lover as much pleasure as possible. She leaned down quickly for a long, passionate kiss on the mouth, sliding her tongue into Rick’s mouth and fencing with his own. After a long while French-kissing passionately, she pulled back and sat up again above Rick, continuing to raise and lower herself up and down upon his cock.

Ash’s hands were everywhere; sliding up and down over Rick’s chest, squeezing and manipulating his cum-heavy balls as she bounced up and down on his cock, and diddling her own swollen, sensitive clit with her fingers. Rick grunted and shuddered with lust as his orgasm threatened to overwhelm him again – he wanted to wait, though, until Ashley had cum again before he allowed himself to climax.

Rick didn’t have all that long at all to wait for Ashley to climax; she was quite close at that very moment. Rick reached up with both hands to grasp a-hold of Ash’s hips as he pounded into her thick-lipped twat with all his might, stretching the walls of her snatch to the limits with the girth of his swollen, rock-solid roger. Then he moved up higher still, to grasp hold of her full, luminous breasts and flicking her stiffened nipples with his forefingers. Rick soon had her grunting and moaning at the top of her lungs, as Ashley diddled her hardened nubbin of turgid flesh with a relish.

He could feel the walls of her cunt twitching as her pussy squeezed Rick’s cockshaft like a velvety globe. He could hardly hold out against Ashley as he relentlessly slammed his dick in and out of her twat, but he did in the end maintain his composure, restraining himself from his own pleasure so that he could help her cum first. In the end, Ashley let out an ear-shattering scream and climaxed all over Rick’s rigid prick and cum-heavy balls, her body jerking and shuddering in ecstasy as her thick, gooey, clear pussy-juices bathing his rigid phallus and throbbing gonads.

Ash didn’t waste much time in climbing off and moving back down to slurp at her lover’s cockshaft again, after a while actually taking the entire length of Rick’s dick down into the back of her mouth. She ran her tongue around the bulbous head of Rick’s cock, then pushed the very tip of her probing tongue into the little piss-slit on the very tip of his throbbing phallus. After a while of deep-throating Rick’s straining cock, Ashley looked up at her lover’s face, and then gave her a soft, sensuous little smile. She was so innocent, so gorgeous, and Rick finally felt his self-control give out at last.

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