Chapter 34: A Cum Contest at Sea

Ryan was always thinking up new ways to have as much sex as possible, and to challenge those around him to push their limits as well. To him, sex was not just fun ... it was healthy and vital. It charged your life force. It exercised your body in the very best way. It made you feel alive and strong, and connected to other people. Orgasms were the best and most incredible thing you could give yourself, and no matter how many he had, each one was always a special and relished experience of its own ... and for Ryan, there were never enough. He loved helping others reach these heights as well.

Over the next week, Ryan had an idea that he put into action. He had decided to throw some money at orgasms, knowing he would thoroughly enjoy seeing others go for their maximums for the added incentive of cash bonuses. It was a strange urge for him, as he certainly had no shortage of orgasms, but he had no shortage of money either and in his own twisted mind, this was his way of sharing with others who had less. He also wanted to break away from his usual partners and have fun with some new playmates. He figured he would need 3 or 4 girls, and at least 2 other guys to make his fantasy come true.

He thought back to when he had the huge orgy for several days to see decide who his housemates were going to be, and realized he had never yet invited Nicole to come play with them ... and she very nearly had ended up being hired as girlfriend #3. He also called Kristen, of course, who was his newest sex devotee and would do pretty much anything he wanted. He also had Kirsten get hold of Lexi, the hot brunette fuckmate Greg had that night they had all spent at Kirsten’s. For the guys, he chose Jake, the Carter twins’ abused and neglected boy toy who had just turned 18, and Shay, that incredibly hot, blonde Adonis from Golden Boy Pool Service.

Each of them got a free 3 day cruise with Ryan on his yacht, out in the ocean with Andre serving as skipper, cook and cabin boy. Each of them also got $1000 just for taking this little excursion with Ryan, not that any of them would have needed that as an incentive. In addition, they had monetary rewards associated with certain things:

First of all, Ryan took care of himself. Nicole, Kirsten and Lexi were to be a team, and their first goal was to make Ryan cum as many times as possible in 48 hours, starting at 6 pm the evening they set sail. They were to split $1000 for each orgasm they got out of him, which Ryan expected would start them with a pot of $20,000 - $25,000 if he was in good form. In fact, he doubled it after 20; starting with Big O #21, it was $2000 per. Then, he got an evil plan in his mind ... He absolutely LOVED torturing other hot guys by pushing them beyond the limits of the sexual capacity they thought they had. So, they also got $500 for each of Jake’s and Shay’s orgasms, plus a $5000 bonus if either of them managed to be within 3 of Ryan’s total.

Ryan really wanted to enjoy watching these gorgeous young studs try to fuck themselves to death ... so, for their part, Jake and Shay had to agree to something pretty daring: Whoever had the least # of orgasms between them consented to letting Ryan suck them off to orgasm and to fuck them in the ass on the 3rd day of the cruise. Both of these boys were 95% straight, but no strangers to varied combinations of group sex, and while they’d never intentionally had sex with guys all on their own, it wouldn’t be the first time a guy had gotten hold of their cocks in one way or another ... and Jake had already been fucked once by Ryan at the Carters’ that one day. Plus, each felt he could outdo the other anyway. Also, the winner between them got an automatic invitation to the next time Ryan put together a fuckfest cruise like this.

Andre pulled the yacht out its dock and headed out of the bay. Within minutes of departing the dock, Ryan slipped off his shorts, the only item of clothing he’d even brought for this trip, and tucked them into one of the storage compartments. He had no intention of needing them until they returned to the dock in two days. He took the yacht out to sea a few miles from shore. It was a very warm, sunny day with just a slight ocean breeze, and soon Nicole and Kristen took off their bikini tops and asked Jake and Shay to help them put suntan lotion on their bodies.

They stopped the boat, and for the first couple hours, the young and mostly nude group partied and enjoyed champagne, hors d’ouvres, Caribbean music, dancing, and a beautiful sunny day on the ocean. These friends were really fun to hang out with in many ways, not just sexually, and Jake in particular was thrilled to be included in this adventure. Though his chiseled, athletic, studly young figure had helped him bed a couple dozen girls in high school like a true jock, he had nowhere close to the experiences and perspective that Ryan had on all that sex could be and all the different ways you could have it. In fact, he’d been so fucking loyal and devoted and whipped by those damn Carter twins and all the delayed gratification they forced on him, that he really hadn’t had a lot of healthy sex with anyone else the last 6 months. He loved the attention he got from the three hot young ladies on board, and he also loved picking Ryan’s brain and hearing sex stories and thinking of new things he would love to try. Ryan couldn’t help sporting a nice, full erection the whole time talking about sex with his friends, especially with three naked women across from him, and noticed Jake and Shay had large bulges and precum wetspots in their trunks as well.

At 5:00, Ryan stood up and announced it was time for everyone to get rid of all clothes for the next 49 hours. Once everyone had stripped off their shorts and bikinis, he had Nicole gather them all up and lock them in the storage compartment where he had put his own shorts. Lexi was just the slightest bit uncomfortable with this, but had made a vow to herself to be brave and go with the flow this trip, trying new things and getting over any inhibitions. This also required a new level of bravado from (barely) 18-year old Jake, though he was eager to challenge himself and experiment with all this.

Lexi didn’t have much time to stress about the nudity though. At about 5:45, Ryan chose her first, knowing she would be the one most in need of letting everything go. In front of everyone and without asking, he hoisted her up on the edge of the boat where she could halfway sit while grabbing a nearby railing, and dove right onto her pussy with his mouth. She screamed and freaked a little at the intense stimulation she suddenly felt, and had a couple minutes of really talking herself out of feeling weird that four other people were watching and encouraging this from just a few feet away ... but Ryan was unrelenting and was determined that she would cum in front of everyone before anything else happened. Young Jake sprouted a raging hardon almost instantly with the bold display of lust happening right in front of him, and Nicole was kind enough to at least start stroking his cock lightly for him.

A few minutes later, Lexi was lost in delight, and gave up all feelings of concern in exchange for more pleasure. She writhed and screamed and gasped as Ryan brought her to a shuddering orgasm, and laughed as the others cheered and clapped. Damn that was weird, she thought, but amazing too. This was going to be one hell of a cruise.

Ryan handed Lexi off to Shay, who was more than happy to let Lexi inhale his meaty cock down her throat. She fondled his balls and groped his sexy, tan, muscular body as she sucked him to full mast, preparing him to fuck her for the first time. Meanwhile, Kristen had noticed that 6:00 pm had just passed, and if she wanted to pocket some serious money this week, it was time they got Ryan started on his first orgasm. She dropped to her hands and knees, looked back at Ryan, and begged him to take her doggy style. From that position, she was also able to help Nicole suck Jake’s cock as he lay on the deck just in front of her. Ryan slammed his raging cock into Kristen’s oh-so-beautiful pussy, and within 5 minutes he announced #1 was on its way. He pulled out, Kristen turned around, and he sprayed it all over her ample tits, ecstatically screaming and hollering. He wanted to have the first ... and last ... orgasms of the three guys this trip. He only beat Jake by about 20 seconds though, as the studly teenager desperately hurled his own first load into Nicole’s mouth and all over her face, nearly passing out with the overwhelming sensation. All four turned to watch Shay, who was now pounding his pelvis in and out of a writhing Lexi, and after a few minutes, he also pulled out and launched big jets of cum all over her face and tits.

And so it began. Nicole wasted no time in taking a handful of Jake’s cum and using it to grab Ryan’s still-hard cock and start jerking him with both hands. “Fuck yeah!,” yelled Ryan. Something as nasty and sexy as that caused a HUGE surge in his own hardness, which Nicole soon slurped and licked expertly, loving the taste of Jake’s cum on Ryan’s beautiful cock. Jake didn’t know quite what to think of that, but didn’t care for very long because his own cock was being impaled by Kristen’s pussy as she lowered herself down on him. He screamed and steeled his will to start fucking again right away.

Lexi wanted to get her hands on hot young Jake too, so she lay next to him while Kirsten fucked him, and kissed him and ran her hands all over his body. He in turn grabbed greedy handfuls of her tits and relished the freedom he had to grope and squeeze such beautiful orbs.

Meanwhile, Shay took a break for a few minutes and sat back watching the delicious scene in front of him while he stroked his cock. Ryan gazed at the blonde Adonis, soaking in his perfectly muscled form and beautiful features. He had hoped to get his hands on Shay from the first day that Kerri had him over cleaning the pool, and though he knew Shay was straight, he got a vibe that he could be swayed, especially after all the new ways he must be having sex now with pool clients. For now, though, Ryan was very happy to watch him. He motioned Shay to come over and join him in pleasing Nicole. Shay surprised her by sliding his cock in from behind, causing her to let out a little scream of delight. Ryan got up on his knees and began fucking her face while Shay fucked her pussy.

“Oh fuck yeah,” yelled an overwhelmed Shay, “this is so rad! Out on a boat in the ocean, fucking for all I’m worth with you hot people ... yeah! Oh baby, your pussy is so hot!”

Ryan reached across towards Shay’s shoulders, and the athletic stud didn’t hesitate at all to reach out for Ryan’s arms too. The lusty boys grabbed each others’ arms for support and then doubled the range of motion their cocks had, slamming further and deeper in and out of Nicole while they steadied themselves above. They started pumping into the poor, helpless girl at the same rhythm, with their cocks driving so deep into both ends of her that Nicole expected them to meet in the middle of her body any second.

“Stick your fucking cock in her ass!” Ryan commanded Shay. Shay sat back in a large, plush leather captain’s chair, and as Nicole positioned her ass over his cock, Ryan got another handful of Jake’s copious earlier cum load from Nicole’s face and used it to lubricate her ass to prepare for Shay’s entrance. Shay again pushed past his instincts to avoid contact with another man’s cum, and began inching his huge cock into Nicole’s ass as she leaned back on him. He grabbed her tits and bit her neck as she impaled herself down and down until there was no more space between them. Shay grabbed her hips and slowly began lifting her up and down his shaft.

Ryan took the opportunity to lick and nibble Nicole’s beautiful tits, and started fingering her clit slowly while she got used to her anal intruder. Nicole writhed and gasped as her pleasure mounted, and soon Ryan latched his mouth onto her pussy and gently serviced her. Whenever 4 or 5 inches of Shay’s long cock pulled out of Nicole’s ass on his outstrokes right beneath Ryan’s mouth, Ryan began putting his tongue where the cock would slide against it on its way back in. Soon, Ryan noticed the cock would linger a moment or two longer for this, and before long, he was licking and mouthing it more fully once every 20-30 seconds as Shay accepted and began to enjoy this.

Shay grunted and groaned, and threw his head back in pleasure. The sun was on his face, his cock was drilling the ass of a beautiful girl he’d just met, and now ... a really expert tongue was dancing all over his shaft whenever it emerged. Next, he felt Ryan’s tongue on his balls ... and screamed “oh fuck yeah!” in delight. Ryan knew Shay was letting go of all concerns, and boldly began sucking the blonde’s balls as well as Nicole’s pussy.

Ryan’s own cock was steel hard and straining for stimulation, and after several minutes of pleasuring his friends orally, he joined them by ramming his cock deep into Nicole’s wet pussy. His balls and sometimes his shaft were in full contact with Shay’s at times, and his arms braced himself on the young man’s shoulders while they sandwiched Nicole between them. Ryan kissed and sucked Nicole’s neck, and the three of them rocked away on the giant chair. Sweat poured, screams echoed, lust rose, and they kept going, eventually moving to lay on a bench seat against the rail. Ryan positioned himself where he could brace himself on the boat railing and enjoy hanging his head and arms over it while letting his torso go crazy slamming away into Nicole’s pussy.

Shay couldn’t handle it much longer in this new position, and announced he was about to fill Nicole’s ass with his load. A moment later, his whole body went rigid as he screamed his delight and emptied his balls inside her. Ryan pulled out of her pussy, and boldly grabbed Shay’s cock and pulled it out of her ass, and then he and Nicole knelt down and bathed it with their tongues. Ryan put Shay’s cock fully into his mouth a couple times and gave him a light blowjob, and Shay treasured the feeling and began to understand why boys have always said other boys give the best oral sex since they know how it feels. After a couple minutes, Nicole sprawled on the bench and pulled Ryan on top of her. Ryan entered her pussy again, his cock desperate to cum, and fucked her hard and fast until he felt orgasm #2 upon him. He pulled out and blasted ropes of cum up and down Nicole’s face, neck and tits.

Meanwhile, Jake had already cum once from the aggressive and unrelenting double blowjob that Kristen and Lexi had treated him to, and was already half-hard again while doing his best to eat Kristen out and finger Lexi at the same time. Nicole thought the athletic teenager looked so cute as he awkwardly tried pleasing the two ladies at the same time, and also noticed his nice cock rising stronger and harder. She rewarded him by laying between his legs and licking his shaft, twirling the head around on her tongue, and sliding her lips up and down his length. She put one of his balls in her mouth and gently rolled and tongued it, and then the other. Then she began sucking his cock in earnest.

The orgy continued non-stop until after 9:00, when, silhouetted by the setting sun, Ryan’s cock shot his 6th load of the evening all over Kristen’s lovely tits. Jake and Shay had just cum in unison a few minutes before while plugging Lexi at both ends, and now lay on the cum-covered deck heaving for air, limp noodles hanging between their legs. Ryan had Andre put together some dinner for them all, and recruited Shay to be the bartender and make Long Island Iced Teas for everyone.

After an hour of eating, drinking, resting and laughing, Ryan noticed Kristen slowly making her way along the railing towards the bow. She was stretching and closing her eyes, deeply breathing in the warm, gentle sea breeze. He joined her at the front tip of the yacht and stood behind her and wrapped his arms around her. He knew she was really falling for him, and he was flattered and so very attracted to her as well. He gently kissed her neck and groped her breasts from behind for several minutes as they quietly looked up at the stars and enjoyed the night air. Soon, Kristen felt his hard cock sliding up and down between her buttocks, and turned her head back over her shoulder to kiss him.

The gorgeous young pair soon found themselves passionately making out while lying on a large, cushioned chaise lounge nearby. Ryan was on the bottom, and soon Kristen moved her face down his body and took his cock in her mouth. She lovingly bathed it in the incredible sensations that only a skilled mouth and throat can provide while Ryan oohed and aahed. Several minutes later, he returned the favor, stimulating her sweet pussy with his expert tongue, and then moved up and earnestly slid his cock inside. He kissed her deeply as he began pushing deeply in and out of her. In the midst of this frantic, lusty orgy, this encounter was more like ... making love ... than another fuckfest romp. It was sweet, caring, passionate, and deeply satisfying to both Ryan and Kristen. When they both finally orgasmed, they remained joined together, embracing and kissing for several minutes...

... but soon it was hard to ignore the sounds coming from the upper deck above them. They looked up to see Nicole’s head and arms leaning over the railing, bouncing and shaking. Her face showed pure lust and ecstasy, and she was screaming and writhing in what must have been an earth-shattering orgasm! Then, they noticed Jake’s smoothly muscled back against the rail beneath her, and Shay’s hands reaching from behind to grab her firm tits. He was fucking her ass from behind, and Jake’s mouth was clamped on her clitoris from below at the same time, causing the intense screaming and thrashing as Nicole came continuously.

Ryan and Kristen watched and laughed for a couple of minutes before making their way up to the deck, just as Shay pulled out and slapped his cock against Nicole’s ass, hollering as he mustered a few small spurts of cum. They also noticed Lexi was laying on the ground between Nicole’s legs, expertly sucking Jake’s cock. Ryan’s own cock was still hard, so without warning, he laid himself down on top of Lexi and shoved his cock into her from behind. Fucking again! There was no stopping him tonight. He came in just a few minutes, and collapsed against the railing next to Jake, who still had not cum despite Lexi’s best oral treatment.

Nicole had finally succumbed to the Jake/Shay onslaught and was a heaving, panting heap of flesh lying on a nearby seat. Jake had a pained look on his face, straining to cum again and doing all he could to will yet another load from his tired cock. Lexi knelt and used her hands on his balls at the same time, and Jake moaned and cussed and almost cried in pleasure, but still wasn’t coming ... so Ryan decided to help. Suddenly, Jake felt a long, strong finger entering his ass from below, as Ryan had reached his hand under Jake’s butt and maneuvered his middle finger into the tight hole. He found the kid’s prostate, and buzzed it ... hard ... and that was all it took. Jake nearly shot up into the air as the deep-rooted orgasm hit him, and hit him hard. He screamed and his body went totally rigid, every nerve ending firing in pleasure, as the orgasm seized him and few small but insanely intense ejaculations pulsed from his cock.

A deep, coma-like sleep came over the six naked people that night. Ryan, Kristen and Nicole took the king sized bed in the captain’s suite. Lexi and Shay shared the second bedroom, where Lexi coaxed another hard-on and a load of cum out of poor Shay’s cock later during the middle of the night. Jake initially passed out on the deck after that last fuck, but Andre’, who had been quietly going about his many duties all evening, found him an hour later and woke him. Jake made his way to a couch in the living quarters and collapsed.

In the morning, Lexi woke wanting to get another load out of Shay. Lexi was really keen on the money Ryan had put up for incentives, but despite 20 minutes of truly great cock sucking, she was unable to get Shay more than half-way hard and half-way awake. She slid out of bed and made her way across the living quarters to Ryan’s room and found him asleep with Kristen and Nicole cuddled up on either side of him. She crawled under the covers between Ryan’s legs and up to his thighs, and found his large, long, beautiful cock uncharacteristically soft for once. “Well,” she thought, “we’ve got to get as many loads of cum out of this crazy stud as we possibly can today, so we’d better get him started early.” With that, she began licking his balls, tickling between them with her hot breath and soft tongue. Ryan squirmed and gasped slightly, and opened his thighs a little further apart. Lexi tongue-bathed his entire nut sac thoroughly, removing all traces of last night’s cum and sex juices, and gradually turning his 5” soft penis into his 8 ½” steel hard shaft.

As Ryan gasped and moaned in pleasure, Nicole and Kristen woke up smiling. Nicole began stroking his chest and teasing his nipples, while Kristen kissed his neck, his ears and soon his mouth. Nicole pulled the blankets off of them, revealing Ryan’s lean, tan, stunningly perfect body ... she thought she could simply stare at it for hours ... and that crazy-awesome cock going in and out of Lexi’s mouth. She joined in, treating Ryan to a double blow job with Lexi. They ran their mouths up and down his shaft at the same time, and then Lexi returned to his ball sac while Nicole nibbled on his cock head. Then, Nicole engulfed his entire member and expertly deep-throated it, vigorously pumping it in and out.

“Oh fuck, oh yeah ... uh huh,” Ryan blabbered, “just like that, oh that’s good head ... oh please, yes, YES, fuck! You’re going to make me cum already...”

“Yes baby,” Kristen said into his ear, “cum for us. We all want your cum! You’re going to do plenty of cumming for all three of us for awhile this morning. Start now, Ryan ... give us your hot cum ... a BIG load of your cum...”

Ryan obliged. As the girls gathered their faces around his cock, Nicole released it from her mouth just as the first rope launched up into the air. It flew over three feet in the air and painted her face as it landed. Ryan screamed. The second and third ropes flew frantically up and out, and landed in Kristen’s hair and all over Ryan’s chest and chin. Nicole kept pumping his shaft with her hand as 8 or 9 more spurts sprayed out all over them. Ryan’s eyes rolled back in his head as he felt euphoric for a few moments.

“Damn, I thought you’d be kind of low on cum after last night,” Lexi said.

“You all sure drained me, but I recover fast. I always seem to need more cum pretty quickly again.”

“Well I hope you have more for us now, then,” said Kristen, “because I want it.”

With that, Ryan rolled over and positioned himself above her warm, wet pussy and impaled her with his still-hard cock. “You better believe it, baby!” he thought to himself. For the next half-hour, Ryan fucked all three girls by himself, driving himself crazy with lust and pleasure. At one point, they managed to lay themselves on top of each other, with all three of their pussies lined up in about 2 feet of vertical space, and Ryan rammed away in one and then another over and over until he came. He then licked up his own cum as it dripped down all three snatches. A few minutes later, he found himself lying on his back with the three girls taking turns riding him from above. He thrust his pelvis up into them rapidly and deeply, and usually tried to have his fingers shoved into one of them at the same time. Finally, he started grunting and moaning extra hard, and pulled his cock out in time to launch his 3rd load of the day all over his chest and the girls’ waiting tongues.