The Downhill Run Pt. 03

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The voyage gets underway and more exciting.
4.2k words
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Part 3 of the 5 part series

Updated 06/08/2023
Created 11/24/2017
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"Oh fuck, that's always so incredibly hot!" Trish exclaimed, her fingers working her own dripping pussy slit furiously.

"Damn right, girlfriend, I just ever get enough of that," Amy chimed in pinching both of her little tits hard.

Just then, Jerry let out a howl, his back arched and his whole body tensed, The first of five spurts of his creamy cum exploded into my mouth and down my throat.

As he went limp, I let his softening dick slip out of my mouth and turned to grin at the girls. A couple of strings of Jerry's jism stretched from the corner of my mouth and down below my chin when I open up to show them the cum coating my tongue.

"Don't you fucking dare swallow that!" Trish exclaimed as she and Amy scrambled over to me, pushing me on to my back and trying to ram both their tongues into my mouth at the same time. Trish won and Amy decided to suck my cock as hard as she could while waiting her turn.

After I shared some of the remaining jism with them both, I leaned back and lit a joint while they licked my cock and balls and spread my asshole with their fingers. It didn't take very long for me to be more than ready to slide my dick into a warm pussy or ass.

Trish got on her knees with her face buried in the seat cushion and Amy climbed on her back, stacked one on the other so I had my choice. Never one to make a final decision until absolutely necessary, I took turns fucking them both until I stated to cum inside Amy. After a couple of spurts I pulled out of her and finished in Trish.

I was done for a while, so I rolled off them both and took a few more hits on the joint that Jerry was working on by then. Damn, I never get tired of watching the two girls licking cum out of each others pussies.

We were about twenty miles off shore heading in a generally southerly direction a few days later when Jerry called us all on deck. So far, it had been smooth sailing and we all settled into a comfortable routine.

"Anyone have a preference for where we head first?" Jerry asked as we settled in on the cushioned benches on both sides of the helm.

"Does it much matter?" I responded as I rolled a nice thick joint.

"Depends how long everyone wants to stay on the boat. We could stop in Cabo or keep heading down the coast. There are several resorts further south that Mel recommends and we have a few months before making the run to Hawaii."

"Can we get shit faced drunk and fuck some whores when we get to shore, like real sailors?" Trish laughed before taking a deep hit on the joint.

"Geez, Trish, changing your priorities to getting drunk before fucking?" Amy giggled taking the joint from me.

By the time we hashed it out and decided to skip Cabo, we were all pretty wasted. That meant we were all super horny again too.

Trish pushed me down on my back on the deck and climbed on to my rigid dick. Then she leaned forward with her stiff nipples brushing across my face while Jerry mounted her from behind and shoved his cock deep into her asshole. Even stoned, I always would cum hard and fast when we DPed one of them, feeling Jerry's dick rubbing against mine.

Amy got herself off once or twice watching us. After our dicks slipped out of Trish's ass and pussy, Amy went to work on Trish's pussy and asshole, licking up as much of the seeping sperm as she could manage while Jerry and I worked on a second joint.

After almost three weeks, we were all ready for a change of pace and get back to some solid ground. Jerry looked over the list Mel gave us and found a resort south of Puerto Vallarta we could reach by mid morning of the next day.

The place really was idyllic. As we approached, we could see a number of casitas scattered along the shore behind a line of tall palm trees. Getting closer to shore, we saw a number of people lounging in the sand or standing in the shallow water.

Jerry had us drop anchor about a hundred yards off shore, since our charts didn't tell us how close we could get. Even before we could get our inflatable dingy set up, a motorized skiff headed out to us, piloted by a tall deeply suntanned guy with flowing blonde hair wearing just a loose fitting mid thigh swimsuit.

"Oh, I'm so going to fuck him!" I heard Trish mutter lowly as the small boat tied up next to us.

"You and me both," Amy responded and edged closer to the railing.

As we first approached the resort, we all put on some clothes for the first time in a few weeks. Jerry and I wore some shorts, while the girls put on tight shorts with skimpy bikini tops that barely covered their nipples.

The guy introduced himself as Shane, the dive master at the resort. He explained that mariners were always welcome there and offered to ferry us in to meet the manager. Jerry and Trish went with him while Amy and I stayed with the boat. Even as they pulled away, I could see Trish flaunting her ample tits for Shane's benefit.

"Think she'll fuck him before they get back?" I asked Amy, cupping her little tits from behind.

"That depends on lots of things but if she doesn't she'll definitely give him a blow job on the ride back," Amy answered and rubbed her taut ass back against the growing bulge in my shorts.

I reached down and slipped my hand under the top of the shorts, pushing my fingertip through the soft cunt hair just above her slit. She was already pretty moist as she groaned lowly when I started swirling my finger over her hard little clit and immediately got a lot wetter. I held her close, fingering her clit and pussy slit as she tensed, her legs quivering when she began to cum.

As her orgasm faded away, she turned, pulled my shorts down around my ankles and dropped to her knees to take my dick into her mouth. I was pretty stoned so knew it would take a while to shoot my own sperm into her.

"Let's take a swim and then I'll fuck you anywhere and anyway you want," I said to her, stepping out of my shorts and diving into the water on the side of the boat facing away from the beach.

She immediately dropped her own shorts and top and dove in after me. We splashed around for a while before climbing back into the boat and going below decks, taking a few more hits on the nearly finished joint which made us both even hornier.

Amy sucked me to the edge of cumming with two fingers in my ass. She stopped and got on her hands and knees so I could easily tongue fuck her asshole while she fingered herself to a quick climax. My dick was throbbing when she rolled me on my back and slipped her dripping pussy down over me, riding me slowly at first and then harder and faster, cumming twice more before my jism flooded into her pussy.

We dozed off to be awakened by Trish climbing on to the bed, leading Jerry in one hand and Shane in the other. Even in the subdued light of the cabin, I could see her tits bouncing freely and a sheen of cum glistening on her cheeks and chin.

"Move over!" she commanded as Amy and I scrambled out of her way.

Trish flopped on the bed then sat up long enough to pull Shane's shorts down around his knees. Unlike all of us, he definitely had pronounced tan lines at his waist and half way down his thighs.

Amy took one look at Shane's pale, half erect dick and crawled over to add her tongue and lips to the guy's balls while Trish swallowed the entire length of his dick until her nose disappeared in his thick pubic hair.

Jerry glanced at me and just shrugged. I reached over and pulled Trish's shorts down and got up on my knees behind her, easily sliding my now hard again cock into her dripping cunt. Jerry did the same with Amy and we fucked them together until Shane grunted his load of cum on to their faces and into their mouths.

The girls kissed each other, sharing Shane's jism on their tongues until in turn they each trembled and groaned their own climaxes. Jerry's cum gushed into Amy just a few thrusts before mine flooded Trish's pussy.

It turned out, the resort was probably as happy to see us as we were to see them. In return for giving the guests a two hour sail each morning and afternoon, they let us share one of the casitas, eat and drink our fill and use any of the other facilities. The initial response was so overwhelming, we had to limit the number to eight on any given trip.

On the very first day, Shane ferried four couples ranging from about our age to that of our parents. All of them were wearing bright orange life vests over their swim suits. Jerry looked at me and shrugged, while Amy and Trish giggled. I was kind of disappointed since their were some very promising tits and asses being partially concealed in that group.

Jerry gave everyone a little speech about not going below deck or falling overboard and such while I was trying to get a better look at some fresh pussy. We planned to go out a couple of miles, sail around a little and head on back in. If we were lucky, we might even catch sight of a few dolphins or something.

Leave it to Trish to get things all stirred up.

We were underway maybe twenty minutes when Trish sauntered up to a guy who looked old enough to be her father. His eyes darted back and forth between her tits and her pussy since she wasn't wearing one of those vests. Her bikini top consisted of two patches about the size of a silver dollar and a bottom about the size of the palm of my hand. The only thing left to the imagination was just how dark were her nipples and cunt hair.

Trish grinned devilishly at the guy before reaching up and fumbling with the snaps on his life vest until they fell open. She kept her eyes locked on his as she brushed just the very tips of her fingers across his now exposed chest.

"Now, you don't really need this silly thing," she cooed, pushing the open vest back over his shoulders until it fell to the deck behind him and at the same time pushing her tits out toward him. "As you can see, none of us are wearing them."

The guy's face flushed and I could see the beginning of a growing bulge in his swim trunks. It also occurred to me the older woman he came aboard with might not appreciate what Trish was doing. I took a couple of steps toward her, then stopped short. The older woman was grinning happily as she loosened her own vest and let it drop. Within minutes, the other passengers did the same.

We spent the next couple of hours cruising around in circles, giving anyone who wanted a chance to steer the boat, with one of us hovering close by. Jerry even did a bit more than hover with a few of the more scantily clad women which was fine with me. I had no doubt we would get to know them a lot better later that evening.

At one point, I noticed Trish was nowhere in sight. When I asked Amy, she had no idea and didn't much care since she had some guy practically drooling down between her tits. When I went to look below, I stopped short half way down the steps. The older guy she teased earlier had Trish bent over the table, fucking her hard from behind. His wife sat in a nearby chair, her swimsuit pulled down around her knees as she furiously rubbed her hairy pussy and urged them both on with language that almost embarrassed me...and I'm a sailor.

The woman looked up when she heard me, grinned wickedly and motioned me to her side. By the time I got there, my dick was at full attention pressing out against my swimsuit. She pulled my trunks down far enough for my dick to pop out into her hand then went back to watching and encouraging her husband to fuck Trish. I just stood there getting harder by the second until she turned back to me.

"So what the fuck are you waiting for, dickhead, get over there and stuff your cock in the pussy husband of mine's mouth. Fuck his throat hard until your cum shoots down into his belly," she commanded, gave my balls a squeeze then slapped my ass hard.

The guy never missed a beat when I stepped next to him, sliding his lips around my dick while continuing to pound Trish's pussy. I had to admit, he gave a damn good blow job, made even better by looking back and forth to his cock slamming Trish and his wife furiously rubbing her clit and pinching her nipples.

Trish started bitching that she couldn't see, so we all separated momentarily, long enough for her to roll on her back just as the guy's jism spurted on to her cunt and belly. Meantime, the guy dropped to his knees and was pulling my cock even deeper down his throat. I knew Trish wouldn't mind just bringing herself to another orgasm while watching, just so she got to see some of my jism on his face or in his mouth.

It turns out the woman who was easily my own mother's age felt the same way, urging him on and telling him not to swallow. Just as I started shooting my cum into his mouth, he pulled the head of my dick out and waved it around, spraying his face and chest.

I collapsed back against the table. Trish grinned up at me while fondling my deflating cock.

The woman got up from the chair, pussy juices freely flowing down the inside of her thighs and walked over to the guy. He leaned back on his legs, looking up at her with his mouth open and tongue extended, my jism coating the surface and dribbling down over his chin. He kinda looked like a panting dog.

When she got next to him, she leaned over and rammed her tongue in his mouth, scooping the cum out before standing, walking over to Trish and kissing her deeply. When she was finished she turned to me and fondled my flaccid cock.

"When you get this hard again, you're more than welcome to fill my cunt or ass or mouth or...if you rather...his ass," she cooed, took her husband by the hand and went back on deck.

"Can I watch?" Trish giggled and sucked me hard again.

And so it went for the next couple of weeks. Twice a day we sailed around for a couple of hours then partied with the guests we met. None of us was complaining at all with the ever changing variety of pussy and ass and cock. It really is amazing what some people will do and cut loose on vacation far from home with people they will never see again.

With the casita the resort furnished, we had a place to sleep, shower and such although one of us stayed on the boat every night, although not necessarily alone. It turned out that Saturday was turn around day, meaning most of the guests who were staying for a week left on Saturday morning to catch planes home. New guests arrived on Sunday. The partying on Friday night was usually the wildest and lasted the longest.

As a result, the first Saturday evening we were there was shaping up to be pretty quiet, with a just few carry over guests and the residential staff.

Jerry and I were sipping some beers after lunch, admiring the really large boobs and bubble butt of a woman twice our age that she was happily and very openly flaunting for us in tiny bikini bottom and top pushed down to expose the beginning of her dark brown nipples. We were debating which of us would fuck her first when the resort manager came up to us, carrying three fresh beers.

"Mind if I join you?" he asked, handing each of us a beer and opening the last one for himself.

Henri was a Frenchman in his early forties from Paris. He managed the resort for the company that owned it and number of others around the world.

We all sipped silently for a few minutes watching the woman lather up her body with sun tan oil in a way that openly suggested she was more than willing to take all three of us on. She kept her eyes locked on our growing boners the entire time.

"I have a favor to ask," Henri finally said when his beer was almost gone. "Would you be willing to take me and a few others on a moonlight sail this evening. The moon will be almost full."

"Sure, no problem," Jerry responded, "that's the least we can do after all you've done for us."

"Excellent, shall we say 8:00 at the dock?" he smiled and stood.

He walked over to the woman, leaned over and whispered something into her ear. Her smile widened as he spoke and her hand rubbed over the fabric barely covering her prominent mound. As he walked away, she rose and stepped over to us, kneeling in the sand between our loungers and running a hand over both of our stiff dicks through our swim suits.

"My husband said you boys had no plans for the rest of the afternoon and told me to make sure both of you very well taken care of."

Her name was Yvette and she sucked and fucked like a pro. Maybe she was. In any case, Jerry and I fucked her every way we could manage for the next few hours. Henri was a truly lucky guy.

By the time Jerry and I and the girls got to the dock after dinner, Henri was already standing there with four young women. We loaded everyone and a large cooler of beer on the skiff, went out to the boat and were shortly underway.

From the moment we got going, it was obvious Henri was there strictly for Trish and Amy. The four girls immediately turned their full attention to Jerry and me. While he showed two of them how to steer the boat with lots of giggles, I went forward with the other two.

When the boat rolled slightly with a low wave, both of them fell against me. They didn't pull back from my arm around each of their waists and before I knew what was happening, they were both kissing me and stripping off my clothes. I looked back to see one of the other girls on her knees sucking Jerry while he groped the fourth one with one hand and tried to steer the boat with the other.

Now the wooden deck was pretty hard, so as soon as the three of us were naked and I had a chance to finger both of their pussies, I took them by the hand and led them below.

Amy, Trish and Henri had already beaten us to the bed. He was fucking Trish from behind while she fingered and licked Amy. He looked up when he saw us standing in the doorway, my hands fondling the two girls' asses while one stroked my dick and the other massaged my balls.

Henri just grinned and moved Trish over to one side, giving us room to join them on the bed. Over the next hour or so, I shot my cum in both girls' mouths, licked their asses and pussies and fucked one in the ass while the other licked my asshole. I'm pretty sure Henri was doing about the same with both Trish and Amy, at least their moans seemed to mean they were enjoying themselves.

On deck, Jerry had enough presence of mind to engage the auto steering before going to town with the two girls on the cushioned seat around the cockpit. By the time we all needed a break we were quite a way from shore. So we turned around and headed back, with the girls trading off and I had the two Jerry fucked and vice versa as we sailed to shore.

It was my turn to stay overnight on the boat. As the others climbed into the skiff to return to shore, Trish came up behind me, wrapped her arms around my chest and whispered in my ear.

"Want some company tonight?" she cooed before sucking my earlobe between her lips.

"Of course, baby, you know...." I started to say and stopped suddenly as I turned to her.

Two of the young women were still on the boat, lounging on the cushions while fondling each others tits. They just grinned and spread their thighs when I looked their way.

Now my dick was pretty limp right then, having just cum three or four times in the space of a couple of hours. As usual, Trish had a perfect solution. She pulled me over to the two girls and headed below. She came back in a minute or so with huge joint.

As I lit up, she took each girl by the hand, kissed each of them deeply and went below again. With the first hints of my coming buzz, I could hear their moans growing ever louder.

The longer I waited to go below myself, and the more of the weed I inhaled, the noisier they got. Finally, with just the first stirrings of a hard on, I stumbled down the ladder and into the doorway of the cabin.

The girls all looked up before one of them got off the bed, took my hand and pulled me down with them. I was immediately engulfed in the scent of their sex, bouncing boobs and some very wet pussies.

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