“So this is how it’s going to be”, I thought to myself.
I looked around at my crew and couldn’t believe my eyes. This is what I get for putting an ad on Craigslist. I should have known better.
Free Trip to Hawaii
I am off to sail the South Pacific and need crew to help sail my boat to my first stop in Hawaii. No experience necessary, just a healthy sense of adventure, no fear and willing to learn and work. Please text me at …
All the men that responded were either pretty weird, running from the law, were lazy or afraid of water. I have no clue what’s wrong with men these days.
Not many women responded – some said they would cook or work in the galley, some said they would go and provide companionship. What’s that mean? Free blowjobs for a trip to Hawaii. That’s the last thing I need is to show up in Hawaii with some disease and someone clinging to me for companionship.
That left me with Monica and her two younger cousins. I looked intently at the girls to try and gauge them. Monica looked to be about 28 or 30. She was very pretty but you could tell she had a rough life. Her tattoos and demeanor along with tell tale scars on her wrists made me think twice if I wanted to be on a boat with her for a few weeks. But I could tell she was someone who had worked hard and would be willing to work hard. Maybe she needed a fresh start. Maybe she just need to escape her life for a while. I don’t know…who am I to judge?
Her cousins were another story. Too young I thought to be away from their parents and out at sea for several weeks with a stranger.
“What’s your story?” I barked at them. “What makes you think you could sail this boat all the way to Hawaii and make it safely? Your hands show you have never worked a day in your life and I see no reason you are going to start today. I need people who are willing to work so get the hell out of here!” I growled at the two younger girls.
The more petite of the two, who I would learn later was named Jessica, instantly started crying and made me feel a bit guilty but I knew they had to be toughened up.
Monica spoke up in their defense, “I’m sorry but we come as a team. I’m responsible for them. Their parents died in a car accident and they have no other f****y. If I’m going then they are going. I promise they will not be any trouble. They need this – to get away from where they lived and all the memories. They need to start a new life. I need this, too.”
I could see a tear in her eye for a moment but she quickly wiped it away and f***ed her blue eyes to look right through me. I felt like a complete asshole.
“Alright”, I said, “if that’s the case then let’s get to work.” I made sure they knew the rules on my boat. They agreed, almost too eagerly but I knew if I was going to the South Pacific one more time they would have to do.
I reached for a line and started teaching them all the knots they were going to need over the next few weeks.
Monica was just like I thought, she was a hard worker and had worked all her life but never caught a break. Over the next few weeks I found out men had mistreated her, stole from her, her f****y never approved of her or her choices. She was a beautiful girl with wavy brown hair and blue eyes. She was average height and she wasn’t too skinny. She kept in shape and when she wore her bikini top around the boat as we worked I could watch her abs flexing with the work. She had a tiny ass with strong legs like a gymnast and her tits were pretty small as well. I would guess a B cup. In the evening, when the air would cool and the breeze pick up a bit her tiny pinhead nipples would press against her top. She worked hard, was pleasant to look at and was fun to be around. I could see how some men would be able to take advantage of her. I think now, with the responsibility of her cousins, her priorities had changed. She wasn’t looking for a boyfriend or husband. She was just trying to do the right thing.
Jessica, little petite Jessica, was just 18 and had barely graduated from high school. I say barely in two ways: just a few weeks earlier and also just barely with her grades. According to her 19 year old s****r Jennifer, or Jen, she was the school party girl. She had been suspended almost every year for d**gs, drinking on campus, sex in the bathroom, flashing, among other trivial things like absenteeism. She had always had a boyfriend and was a handful for her parents to handle. She could get away with everything because she was so damn cute. She was a little shorter than Monica but much smaller. Almost too small. Her legs were very nice and went all the way up to a tiny little ass with pretty large thigh gap. And she liked to show off her legs and ass by wearing little cut-offs with barely a strip of cloth between her legs. And I swear she never wore any panties. Her taut stomach and waist gave way to small tits with perpetually hard nipples. I don’t think a bra would do her any good as swollen as her nipples always were. Not that she would wear one. She had blond hair and deep brown eyes that she could puppy dog you with. I could tell she would be a hard person to say no to.
Every day she would come out on deck and stretch and do a little yoga (which is hard to do on a sailboat). Jen and Monica would groan when they would see what she was wearing every day, short shorts, halter tops, bikini tops and bottoms, loose shirts tied up in a knot. And then she would stretch. I don’t know how she did it but she would always find a spot where I could get a good look at her body. And it was a show for me every morning right in front of Monica and Jen. Pulling a leg up tight against her side while she stood on the other, her bare pussy visible to all. Then the other leg. Bending and letting her top fall away from her body exposing her tiny tits capped with their giant, hard and dark cherries. She was all bubbly and excited when she finished. I could tell she was up to something but I determined I wouldn’t get caught up in their drama. I think she thought if she could seduce me than she wouldn’t have to do her share of the work. I was on to her.
Jen was the quiet, shy one. Very studious and learned her knots faster than anyone. She was the one I could count on in a pinch. She hardly ever wore her bikini top and prefered loose fitting sweats or shorts. I could tell she had a nice body but prefered not to show it off. I could have a conversation with her that made sense. She knew the sail plan, she knew how to a handle a man or woman overboard situation. As she got to know me she loosened up a bit and shared how her little s****r always got the attention and got her way. I could tell she was a little jealous but I assured her that in the real world, not high school or college or mommy and daddy’s house, Jessica’s act would wear thin in a hurry. She would be the girl everyone dated and no one married.
We worked together everyday for several weeks getting things ship shape and ready for a two to four week sail to Hawaii. We prepared like it would take four weeks because you never really know. Jen and Monica doing most of the work and Jessica providing an outlet for all of us to be a little ticked at. I tried to keep on her but she was so cute and fun to be around and I think the other girls just put up with her but I knew they really liked her deep down.
After a couple of weeks we got a good weather window and we knew we would have to leave early the next morning. I sent the girls to town to pick up supplies, food and water, to last a month. I spent the evening on the internet and radio giving the Coast Guard our sail plan, how many on board, ages, ID numbers, etc. The Coastie on the other end just laughed and said, “I hope you have a good trip…I know you will!”
I didn’t catch his humor at first since he was all business when I first started talking with him but after a moment or two I understood what he was trying to say.
“It’s not like that,” I blurted out, kinda embarrassed, just as the girls returned with all the supplies. “Yeah, right! Fair winds Cap’n” and with that he was gone.
“OK, let’s get organized,” I said. We got our our notebook and Jessica took notes while we packed everything into the lockers and under the settees and every other empty spot on the boat. I found stuff that wasn’t on the list, like beer and whiskey and wine and champagne, even a package of condoms. This really pissed me off.
“What the hell is this?” I yelled.
Monica apologised and said it was for her when she got to Hawaii. She said she had already gone three weeks without sex and she wasn’t looking forward to two or three more weeks. She said that when she got there she was going screw the brains out of the first man she saw.
What could I say, I just laughed and said, “Good luck with that!”
We got everything packed and set our alarm for 3:00 AM. We discussed our watch schedule. We set it up so everyone had 6 hours on watch every day but it was broken into 4 and 2 hour shifts. That way everyone would be able to get some sl**p every other night and also not be paired with the same person every time. Basically when you were on 4 hour watch, half way through someone would relieve your partner. When you were off watch you got 6 and then 12 hours each day. Enough for plenty of rest and also to not get so bored. I had made this trip a few times and boredom was the sailor’s biggest enemy. You could go a week without seeing another boat or two weeks without talking to anyone.
Three AM came quickly as we all went to sl**p after our work was done. We eased out of the slip, pulled in the lines and quietly motored out of harbor. As soon as we were around the breakwater we hauled up the mainsail and let the gyb run free until it caught the wind. We adjusted the sails like we had practiced, shut off the engine and listened to the quiet of the boat as she cut through the swells gently rocking us. I had the first watch along with Jessica. We watched the stars go by and discussed what we expected the next couple of weeks.
She said she really wanted to show how good of a sailor she was and how much she had learned. She also said she really appreciated how much I had done for her and her s****r.
She was looking forward to an adventure trying to be “mature for once” as she put it.
After a couple of hours Monica came up on deck and relieved Jessica. Before Jessica went to sl**p she put a pot of coffee on and they went to bed. Monica would be on for four hours and I was to go to bed about 8 AM. I knew I wouldn’t be able to sl**p the first day. Too much excitement for me. This is what I lived for – the open ocean. No cell phones or news. Man vs.nature. My plan was to make a nice breakfast for everyone and then do some chores around the boat. Make sure all was well, take a nap and then go back on watch.
The first couple of days went smoothly but I could tell boredom was setting in.
I awoke to Jen’s voice yelling, “Jessica, put your clothes back on!” “He will see you and your supposed to be on watch, not getting a suntan!”
I could tell she was mad as hell at her s****r and this had been going on a while. I didn’t open my eyes but I stirred in my bunk and re-arranged myself so I could see what was going on. Sure enough Jessica was lying naked in the cockpit, Jen was covered up as if she was a nun and the two of them were going at it. I pretended to be asl**p and just enjoyed the view. Jessica was stunning, she always had been. Her were egs spread and her open pussy just staring straight at me.
I let my hand find it’s way down to my cock and I slowly stroked it, feeling it harden with every tug. I knew they couldn’t see my hand so I pulled the blanket off and let ‘The Sea Monster’ dangle in the cool salty air, slowly stroking as I eyed Jessica’s young, nubile body. I could feel my cock thicken and lengthen, slowly growing to it’s full 8” length and 2” diameter. The head growing even thicker and brighter, slowly oozing pre-cum which I used to lubricate myself. It had been many years since I had been with a woman who looked like Jessica. The old whores around the marina gave my dick the ‘Sea Monster’ nickname years ago but they sure didn’t compare to the vision I had that day.
“I guess you like what you see, eh Captain?” I heard from across the cabin. Dammit – I forgot Monica was down below. She wasn’t on watch and she obviously wasn’t sl**ping.
She came across the cabin while I was dumbfounded. I hadn’t been caught masterbating since I was a teenager and now I’m 55 years and some young girl catches me. She came across the cabin and her hand quickly replace mine since I had instinctively pulled my hand back. She slowly stroked me up and down and said, “You watch that young teenager on deck and I’ll make sure you never forget what a real woman can do.”
I felt her lips wrap themselves around my head, one hand fondling my balls while the other hand squeezed and slid up and down my shaft. I watched Jessica as she try to tan while Jen did everything in her power to cover her up but she kept throwing off whatever Jen put over her.
The feeling of Monica’s lips and tongue were too much. I closed my eyes and felt the suction of her mouth, the softness of the lips, the gentleness of her hands. I also felt a stiff finger slowly start to slide in and out of my asshole. I had never felt that before. Every time it went in and out it made me want to cum but I couldn’t, not yet. I watched Jessica say to Jen, “if you don’t like me working on my tan you sure as hell won’t like when I make myself cum!” They were yelling at each other at this point. It’s a good thing no one was around for 100 miles to hear the two s****rs fighting.
Jessica started rubbing her pussy and pulled her lips as far apart as she could. Slowly dipping two fingers in and out of her pussy.
“You disgust me!” I heard Jen cry out. You could hear the tears in her voice.
My instincts got the best of me and I yelled out, “Hey you two, knock it off!” Unfortunately all that did was change the focus to me laying in my bunk with my cock in Monica’s mouth and her finger up my ass.
Oh shit, I thought to myself. Now I’ve really screwed things up.
“Cap’n?” I heard Jen say, totally confused about how her ship shape boat and captain had suddenly become a floating den of iniquity.
“Cap’n!” I heard Jessica say excitedly almost simultaneously as Jen. “Fuck yeah! Suck him off Monica!” she yelled as her whore party girl alter ego came out.
Just as she was saying that she spread her pussy wider and started furiously finger fucking herself and rubbing her clit. I could tell by the spasms of her stomach she was getting pretty close to making herself cum.
That sent me over the edge and I blasted the back of Monica’s throat with spurt after spurt of cum. She swallowed nearly all of it but a little leaked out of her mouth and down my shaft. She kept on sucking and milking me as dry as she could.
Seeing the cum leaking out of her cousin’s mouth put Jessica over the edge and screamed “OH FUUUUUUUUCK ME!” and she shook violently in her orgasmic spasm. She kept pumping her fingers while she was cumming and in about minute she came again, not quite as loud and violent but she was definitely came, judging by the beautiful creamy flow coming from her pussy.
I couldn’t help but watch her as she looked straight at me. She cupped her fingers and pulled as much of her cum up into her mouth, tasting herself while she left a slippery trail of cum from her pussy to her mouth. God, I wanted to follow that trail with my tongue.
Fuck, what am I thinking. I have to get control of this situation and get my crew back on task. No one had been on look out for about half an hour now and we could have been run down by a cargo ship. I looked anxiously at Jen hoping she was on lookout and she had pulled her top off and was twisting one of her huge nipples into a hard nub while her other hand was down her sweatpants. That was new one for me. What the hell is happening?
I stood up and poked my head out into the cockpit. I knew I had to look around to see if we were safe but with two teenage s****rs, each with their hands on their pussys and massaging their tits it was pretty difficult. On top of that, my shorts were down around my ankles and Monica was busy pulling her bikini top off. Things were getting out of hand real quick.
Thankfully all was clear. I looked around at the sexy women around me, our situation far from shore, in international waters where the captain’s word is law, and realized I had stumbled on every man’s dream. Suddenly my goal of getting to Hawaii in a few weeks didn’t seem so important. Time was of the essence. How do I use these young hormones to my advantage? How do I do it without getting arrested in Hawaii? How long can we stay out here as long as possible without these girls getting suspicious?
“What the hell, Jen!” I yelled with my most commanding voice. She immediately stopped her nipple pinching and clit rubbing and looked at me with her beautiful puppy dog eyes.
“I leave you in charge and I wake up to an almost full blown orgy!”
“But Captain…..” her voice trailed off looking for an excuse or reason that she knew didn’t exist.
“Everyone on deck,” I commanded. “In light of today’s events we are going to have to set some very specific rules.”
I knew blaming Jen was wrong but I also knew that I could rely on her to make sure the rules were kept from now on. She was my enf***er, the one I could trust. She also had the most beautiful, thick nipples. I wanted to see more of them. I wondered if she had beautiful thick pussy lips. The kind that’s fun to suck on and pull deep into your mouth.
“I see your young hormones are going to be a problem. We are only two days into this trip. We have many more. We are going to make sure this does not become a problem.” I stated in my most matter of fact voice.
“I’m sorry Captain,” Jen finally spoke up. I turn to her to her to see what she had to say.
“You will not be making any more rules or telling us what to do or when to do it. We are in charge now. We will be making new rules and you will have to follow them explicitly or your body will never be found. Accidents can happen at sea, no one would ever see you go overboard and no one but the sharks will ever find you.”
“You can’t do that!” I yelled at her about the time I felt two lines going around my arms as Jessica and Monica quickly had me tied to the forward starboard and port winches. The knots I had expertly showed them a few weeks ago now held me prisoner on my own boat. I heard the lines going through the winches and being pulled taught. My arms involuntarily spreading as I pulled against the impossible strength of the winches. I spread my legs to gain gain some balance and leverage.
Jen reached down looped two more lines around my ankles. She quickly tied them up and they were already fed through the aft winches. She quickly pulled them tight and as they pulled I felt myself slowly being pulled into a horizontal position. Monica grabbed the emergency halyard and hooked my belt buckle into into it as Jessica pulled me up about two feet off of the deck.
“These bitches,” I thought. “They had been planning this all along. What a fool I am”.
Slowly Monica cut away all my clothes so I has hanging there completely nude. As she used the knife her hands massaged my cock, slowly and involuntarily, bringing it to life.
“See girls, this is what a real cock looks like” as they all gathered around and let their fingers explore my manhood. They made it twitch and they massaged my balls. Jessica let her fingers run through the hair on my chest and then back down the my hard dick. They took turns pulling the massive head into their mouths and letting it ‘pop’ out. Giggling like c***dren with a new toy.
“Rule 1,” I heard Jen say, “you will be naked for the rest of our trip at all times. Just so it is fair, we will be naked as well. Clothes will only be made available in case of visual contact with another ship.”
“Rule 2, our pussy’s will need to be eaten every day. We are young and need to come everyday. Fucking will only occurr once our pussy’s are eaten and made to come in a satisfactory manner.” said Jessica.
“Dammit Jessica, that’s supposed to be Rule 4! Why can’t you get anything right?,” exclaimed Monica.
“Fuck you, I need my pussy eaten now. I don’t have time for all these damn rules!”
Slowly Jen leaned over and gave Jessica’s pussy a lick from her asshole all the way up to her clit and slowly began sucking on her clit.
Jessica began to moan and then Jen pulled away real quick and laughed. “There’s more where that came from if you just let us get through the rules.” she said.
I could feel pre-cum oozing from my cock. Monica quickly noticed and ran her tongue up and down my dick, cleaning it all up.
“Rule 2, you will cock and balls and asshole will be shaved clean” said Jen. “They are our property and we can suck and fuck them as we like.”
“Rule 3, you will not be allowed to jerk off like you were earlier today. We love come and we do not want to see any of it wasted.”
“Rule 4, it is your job to make sure each of us comes every day at least once. The more the better.” As if to emphasize Jen’s point Jessica slowly lowered her pussy onto my mouth. I could feel and taste her warm juices flowing from her cunt. She was a horny little bitch and she couldn’t wait much longer. I could feel my dick twitching as more cum leaked out the tip. I could feel Monica’s tongue doing clean up duty.
“Dammit Jessica!” Jen again trying to get through the rules. At this point I was getting a little impatient. I did not see any problem with these rules.
“Rule 5, no one will ever know what happens on this trip. If you say a word there will be three young, proper ladies claiming **** against you.”
To be continued….