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Business on a Sailboat

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The day started at 5 a.m. and our first charter was at 9. I had a 2 ½ hour drive to work with the Captain on my first service charter! We had the discussion for some time to expand the options he included in his business to make memories for clientele as well as income for the business. This seemed like the perfect opportunity! My husband and I have know the Captain for several years and my husband trusted me and also knew the Cap?t would keep me safe in any situation. After packing several items for the day and showering I gave some love to my husband and headed for Michigan.

Arriving at the boat around 8:15 a.m., I helped get things ready for our full day, full service business charter. The sailboat is pristine, and we have enjoyed lots of great personal memories on her with the Cap?t but today I was working for someone else! My role for the day was to keep the clients happy and make sure they had everything they needed?.drinks, food, music, and comfort during their day. Easy enough! The captain informed me of our high-titled group of gentlemen that booked their cruise to get away from the pressures of work. They are CEO?s or Presidents of a nearby business.. (Business name left out for the privacy of our client.) They were paying good money to have a full day charter and the extra to have it also full service, with me as their personal assistant!

As the time approached to set sail, I was ready and dressed in a flowing yellow and white plunging, halter-top sundress and barefoot. My dark blonde hair was pined up in a loose twist and I was wearing my sunglasses. I am 5?9? and long legs with nice full C-cup breasts. A very sexy picture to start the day and the Cap?t approved very much which was no surprise (considering I know how much I already turn him on!)

We see our clients walking the boardwalk to our slip and I noticed very nicely dressed, for a hot sunny day, four businessmen. They each carried a small bag, which I assumed had changes of clothing and items for the day. Hiding behind my sunglasses I was able to look each one over, as they got closer and tried to get a first impression from each of them. The Cap?t introduced himself and then me and we all shook hands and he welcomed them onto the boat. He then took my hand and helped me aboard and then untied all the ropes. He then boarded himself.

The gentlemen looked to be between late 30?s-mid 50?s, but they all had sunglasses as well. It was hard to really figure out because they were all in great shape and well groomed. I couldn?t tell who was looking at me and scanning me over and who was not! Although I was pretty nervous, while Cap?t was getting ready to pull out of the dock I showed our guys around the living quarters on the vessel. I showed them where to put their belongings in the bedroom at the bow. I had already claimed the stateroom for my belongings! Cap?t went over the mandatory safety guidelines of the sailboat and I broke out the first round of Michigan brewed beer. As we were heading down the channel toward Lake Michigan we sat near the captain?s wheel and discussed the expectations of the day. They wanted to sail most of the day, enjoy the sun and at some point, drop anchor and swim from the boat. Sounded perfect to me! They were really nice guys and conversation flowed easily. Our captain was very comfortable with them and gave me thumbs up?my queue that things would be fine! As we reached the lake, 3 of the guys had already finished their first beer, so I immediately took the empty bottles and went downstairs to get their refills. They were chatting with the captain as I came back up to the stern. I heard the captain say, ?that?s solely up to her.? ?Fill me in?!?, I questioned.

One of the younger guys had asked the captain if I was going to be in a swimsuit at any point. I laughed and told them, ?Okay, here?s the deal. You paid for a ?waitress?, but if you want it to get better, I will be collecting tips!!? ?The higher the tip, the better your time will be!? (That took some courage; because I have never done this before- remember it?s my first charter!) The Captian said, ?So to get you from the dress to a bathing suit?they have to tip you?? ?Precisely?, I smiled. He smiled back because he knew he?d have a great view for free, all he had to do is man the wheel! The guys all seemed to comply with out a flinch. The youngest of the group took out $20.00 and handed it to me. I looked at the others and they followed suit. I took the money and headed downstairs with 2 empty bottles. ?I?ll be back with your refills in a moment,? I told them. I went into the stateroom and put on my tank-ini. Cute, but not the sexiest suit I owned! This was just the beginning!! I grabbed the 2 bottles and headed back up. ?Okay, okay I see where this is going,? one of them said. We will call him Jake. He was the same one who asked about the swimsuit to begin with. He was around 40ish. I really couldn?t complain, they were all nice looking. Another guy, ?Robert?, asked if I had anything else to wear because this suit was not showing enough. I just replied, ?We will have to wait and see!?

I suggested that they should change into their suits so they could relax on the bow and enjoy the sun and their beer. Thinking it was a good idea; they went downstairs and took turns in the bedroom and bathroom to change. Robert, probably in his early 50?s, was finished first and was standing by the couch talking to ?Steve? who was mid to late 40?s. While they changed, I stayed upstairs and was chatting with Cap?t. ?What a great idea!? he told me. ?Well, I wasn?t sure it would work, but they don?t look like money is a problem for them, so they can afford a little fun!? I just knew that if I wanted a good paycheck, I needed to turn up the flirt factor!

They started back upstairs to where we were sitting. The 4th one of the guys, ?Ryan?, who was also the oldest of the bunch, guessing maybe mid to late 50?s but still very sharp looking and classy, said ? So how much to change out of this bathing suit?? I was caught a little off guard but replied, ?another $20.00.? ?No problem.? I told them to relax at the bow and I?d bring them another drink and a different suit. The captain smiled a huge smile, again, as I headed to the stateroom. It was only about an hour or so into our cruise and things were going great so far! I changed into my pink leopard print mono-kini. It is very low cut and sexier but not quite a bikini!

I prepared a plate full of cheese and crackers and gr*pes and grabbed 4 bottles, which were super cold, against my skin, causing my nipples to become erect! With my hands full I managed to make it to the bow and handed the plate to Steve. They were all smiling of approval and grabbed their drinks. (That?s a good sign!) I told them to enjoy themselves and I would be back in a little bit. I sat under the dodger facing the captain and we talked for a little while when Ryan was waving for me. It was about 11 a.m. when they asked if I could make them some sandwiches and another drink. I told them I could make them a shot to go along with lunch. They liked the idea and I took the bottles and mostly empty plate and went to the kitchen. I worked on making their sandwiches and poured 4 shots of Jose Quervo. I put the plates of sandwiches and fresh veggies on the tray along with 4 shots. I brought up a beer for the captain as I took the tray to the guys. As I approached them they each had another $20 in their hands. I laughed and traded the tray for the cash, knowing what they wanted. They made a toast, ?To sailing, bikinis and good friends!? I took the shot glasses and headed once again downstairs. I tucked away that money and changed into my skimpy string bikini with triangle top and tie sides. It was very bright colors to extenuate my tan. I also took the time to text my hubby and tell him I already made $320.00 in tips and had only changed my clothes! He texted back to have fun and enjoy my day on the boat! What a sweetie!

I grabbed more beer, and also one for myself and took them to our clients who were starting to get louder and silly. ?I think the alcohol is setting in,? Captain said. When I approached them Steve said, ?Now that?s what I?m talking about!? They seemed to all approve of this new suit. I gave them a few more minutes to finish their lunch before gathering their plates. It was nearly 1pm and the captain and I could tell they were enjoying themselves. They headed back toward the stern where we were sitting and I moved so they could sit in the seating area between the steering column and the dodger. I sat under the dodger again, facing the captain. It was very comfortable just sitting and hanging out and talking. Robert suggested some music, which I thought, was a great idea. They all agreed that they didn?t care what kind of music so I played my I-phone play list. (Yay for me!) I made another shot for each of them while I was setting up the music. I gave them their shots, waited for them to decide what to toast? ?To having a great time on the lake and having an awesome captain and waitress!? (Okay, works for me.) I took the glasses back downstairs. Six beers came back up with me and Ryan made the comment that he hoped I wasn?t going to burn with so much skin showing. Cap?t quickly spoke up and offered his lotion. ?For the right price, she may let you all take turns applying it!? I threw him a quirky smile and he smiled back. ?Well, that would include touching, so that gets a little steeper on the tip.? Without a second thought Jake said ?$50 bucks to let us each apply lotion to you?? I didn?t think twice either and quickly agreed.

I stood in the center of all 5 guys and held onto the handle of the dodger, while letting them all one by one, rub lotion on all my bare skin. Jake and Robert each took a leg and didn?t hesitate to rub it into the utmost part of my inner thigh to my ankles. Ryan rubbed down my back and shoulders and Steve was rubbing it into my abdomen and arms. Wow, what a feeling! I don?t think I?ve ever had 8 hands on me all at once and it was really turning me on. After all the lotion was rubbed in I started swaying my hips to the music. Two of them got up and started their own dance while the other two continued to talk and watch the view. This dancing and talking went on for a couple more drinks, when I finally spoke up and said, ?Hey boys, I have another outfit.? They reached into their pockets and pulled out another $20 each. I went to the stateroom, took a deep breath and came out with a bright purple, ruffled thong, and no top. As I headed back upstairs, all five men stopped mid-sentence and starred at my tits and my very revealing thong. That?s the reaction I like! ?Wow? ?holy shit she?s so hot? was a couple things I was hearing. My full C cup breasts and erect nipples were exposed to these 4 strangers and my Cap?t. He of course grinned from ear to ear and took a picture of me to send to my husband. ?Damn, she?s so hot?, was the reply he got back. There was more drinking, dancing and conversation when one of my favorite songs by Rob Thomas came on the surround sound. I started touching my abs and caressing my breasts as I was dancing and had their full attention. By this time in our cruise we had sailed far enough from the coast that I was not worried about anyone else watching. I closed my eyes and let the music take me over. I rubbed myself and was dancing in the midst of ten adoring eyes! When the song was coming to an end, I opened my eyes to see Robert and Jake rubbing themselves over their swimsuit. I smiled at them. As the song changed, I said,?Who needs another beer and a skinny-dip?? ?Hell yeah,? Steve replied. ?But, skinny-dipping requires no clothing.? the captain reminded. Two of them had to go downstairs and grab additional cash and after returning they all handed me another $20, and the captain gave me a wink. He pulled the sails down and we anchored the vessel.

At her stern is a swimming pad so we were gathered toward the rear of the boat. ?What are you guys waiting for?? I asked. Jake replied, ?Ummm, well for you of course. Ladies first after all!? I slid my thumbs under the sides of my thong and slowly slid them down my hips. I could feel the moisture in my thong as they moved down my legs. I caressed my thighs as I pushed the thong lower. I slid them all the way off and slid my hands back up my legs as I stood up. I rubbed my inner things and up to my breasts. Besides the music playing, no one was saying a word. Just eyes. All over my naked body. How exhilarating! ?Well?? I said?and they all started undressing! ?You guys go in first.? One at a time they jumped into the open water and turned to watch me. I grabbed the clip in my hair and shook out the twist so my hair fell around my shoulders and down my back. Steve said, ?How beautiful, I didn?t think it was that long.? I ran my hands through it a couple times to give the guys a good look at my body before diving in with them.

Cap?t threw in a float and a rope lead, so I climbed onto it and tied the lead to the handle of the float so the waves wouldn?t carry me away. The guys were swimming around the float and splashing each other and me. They were definitely having a great time. The captain also came in with us. The sun was hot and it was about 3 o?clock. We spent a while in the water and then Robert asked if I needed more lotion. I told him ?sure?. I was lying on my stomach so they all gathered around the float and started rubbing lotion all over my skin. A few times I felt someone?s hand graze my labia and it made me squirm. Having their hands all over me, that close to my pleasure points was intense. I told them I needed to turn over so they could rub lotion onto my front side. Cap?t was sitting on the swim platform taking a few pictures. I knew he was sending them to my husband, who was probably going crazy wondering how my cruise was going! He said that he told hubby things were going great, so that relieved me. I knew I was safe with Cap?t there.

I was on my back and my breasts were point to the sun. Ryan asked if he could apply the lotion to my girls, and I nodded yes. He softly rubbed lotion around and over my nipples and I could hear him moan quietly under his breath. The others were watching in anticipation for their turn. While waiting, I was starting to get that throbbing of lust in my sweet spot. I could feel their eyes on me and they could see that my pussy was starting to glisten in the sun. Robert cupped my breast in his hand and started to flick his tongue against my nipple. I was getting so turned on, so I told them we should take this back aboard the boat and get another drink. They agreed and as they were climbing back onto the swimming pad, I could see that they all had erections, including Cap?t! (Wow, I was doing this to 5 guys and I hadn?t really done anything at all!)

?You guys can get dressed if you?d like, but I think I?m more comfortable like this,? I told them. ?Would you all want shots, beer or both?? I hollered back upstairs to them. Steve answered back, ?Bring us all 1 of each, including yourself.? I poured 6 shots and grabbed 6 icy cold bottles and handed them up to my horny men. I told them that they each had to take their shot from between my tits without using any hands. They had no argument with that. I placed each glass one at a time between my breasts and one by one they smothered their face into my chest to take their shot! I was so wet and horny! After they were done with the shots, the captain and I clinked our glasses and took our shot. They sat back in their seats while I sat under the dodger. It was going on about 5 p.m. The sun was still warm and we were all feeling good.

?Well, I have nothing more to take off, but I have something to show you!? I said in a very sexy voice. No one had put any clothes on, so they scrambled for their trunks and each handed me $20. I tucked that into my bag under the steps and turned back to them. Our captain had the direct-on view behind the big wheel of our ship. Two were on my left and the other two on my right. I took my bottle of beer and started rubbing it across my nipples making them tall and perky. I slowly moved the bottle?s end to my stomach and then to my pussy. I spread my knees wide and pushed the bottle against my swollen cunt lips. I moved it up and down and they could now see the darkness of my shaven pussy. I took the bottle back up my chest and poured some of the beer down my front. It ran into my ?V? and made me groan. The coolness felt nice against the sun?s heat. The music was playing, the waves were rocking us gently and I had full attention of all eyes and erect ?members? of our boat.

I rubbed my hand in my inner thigh and over my clit. It was pulsating for my touch. I put a finger on each side of my clit to open my lips up wide and with the mouth of the hard bottle started rubbing my magic spot. It felt so awesome and wouldn?t take long for me to cum with all of them watching. Cap?t took a few pictures and sent them on to my hubby, and told me he was in much approval and proud of his erotic wife! I set the bottle down beside me and started rubbing my fingers over my clit and over my wet hole. I was so wet that it was impossible to avoid slipping my fingers inside. I used two fingers and slowly entered my cunt. I heard Robert, ?Oh yeah baby, bang that cunt.? Steve was stroking his cock, which was about 6 ½ inches in his right hand, and beer in the other. As I looked at each of them, they were all solid hard, sweaty and focused on my every move. I slid my fingers in deeper and with that came a load moan. I pushed my hips against my hand and forced my fingers as deep as they would go. Oh my God, I was finger fucking myself with 5 men right in front of me. I couldn?t believe it. I thrust my fingers in once more and pulled away a very wet hand, sloppy with my sex juice. I started to use the other hand and I licked the juice off of my fingers. Ryan spoke up and asked if he could taste me, so I reached over to him with cum fingers and he put both fingers in his mouth and sucked softly on them. I was mesmerized by his delicacy. ?That was wonderful. You taste amazing.? He commented. I took my hand back and started banging myself harder, ?Oh yeah, oh yeah,? someone said. I opened my eyes to see Jake cum into his trunks on his lap. He was stroking his member slowly now and letting out soft moans. I smiled at his as I continued to trust my fingers. Robert reached over and was fondling my nipple and that added touch sent me over the edge. I leaned back to support myself and my legs were as wide as I could get them exposing my throbbing pussy to all the guys. I was moaning and crying out with pleasure. I sat back up as I was rubbing myself slowly.

Ryan said, ?how much to fuck that cunt?? ?I?m not real sure,? I told him. I looked at Cap?t and asked if he would check with my husband. A short time later he had a reply??200 and only if she?s comfortable with it and he?s covered.? I read it to myself and thought what could be going thru his mind! I told Ryan it would be $200 and I would take him downstairs. He quickly agreed. He followed me downstairs and put on a rubber. Cap?t had a great view from his captain?s chair and Jake followed us down for a better view. I leaned over the table, supporting myself with the mast pole and could feel him behind me. I raised my left leg to the seat and he grabbed my hips and pushed into me. I let out a huge groan as he pushed as deep as his 7 ½ inches would allow. He pulled back and my cunt wanted more. ?Oh again, again,? I begged. He thrust forward again and I moaned loudly. ?I can?t believe I?m fucking this hot pussy, this tight pussy.? I grabbed the mast and the table for support because I could feel his grip getting tighter and I was right. Pound, pound, pound over and over and faster he shoved his penis into me. The captain was taking pictures from his view and sending them to hubby. Jake was stroking his cock and he was hard all over again.

Ryan was pounding me and my tits were bouncing uncontrollably. Jake got up and when he returned he laid a $50 on the table in front of me. He slid around the table so his hard cock was by my face and asked if it was enough for me to suck him. ?Please!? he added. So I leaned forward to put his cock in my mouth and Ryan would push so hard into me I thought I would scream, but now had jakes cock in my mouth. I was having a hard time blowing him with all the thrusting going on behind me. I managed to continue sucking on the head of Jakes cock and stroking him with my hand. Ryan would slow down enough for me get a deep throat in on Jake but when he would speed back up, I?d have to go back to the mushroom tip. This pounding and sucking and my moaning and screaming out of exhilarating pleasure, continued and continued. ?I?m cumming, I?m cumming? I yelled out 3 or 4 times. Ryan held me tight against him with his balls touching my clit and started moaning and pulsating. That was my chance to get Jake off so I went down on him as much as I could handle with the BJ my husband would be proud of! He blew his load to back of my throat and I swallowed it down.

Ryan slowly released his grip on me and pulled himself out of my swollen cunt. I was dripping my juices down my thigh. We cleaned off and I used the restroom. When I came back out the guys were all back upstairs. I grabbed 5 beers, (no more for me!) and went to sit up on the deck with them. The sun was getting lower in the sky but was still about 7 p.m. Cap?t turned the boat back toward our channel and we headed back towards the lighthouses. We had been anchored for awhile, and it was incredibly peaceful on Lake Michigan. Now the engine was running so we had to talk a little louder! They decided to get dressed and one at a time took their turn using the bedroom and bathroom, and put their ?business? attire back on. (Who wore polo shirts and khaki pants on a sailboat anyways?!) They were enjoying one last beer as I went back downstairs to put on my sundress. When I came back upstairs we were heading into our channel. They all made comments on how much fun they had and Robert said, ?So Cap?t, I?m engaged to married next summer, can I have a bachelor party with you and ?her? as well?? he said, ?Sure, if she?s available!? They all chuckled as I blushed! Cap?t parked the vessel in her slip and we helped off load the bags and gave the gentlemen handshakes and hugs. ?Get with me about your bachelor party!? Cap?t said. ?Will do for sure!? Robert replied back.

Captain and I went back onboard to clean stuff up from our wild day and he showed me a few pictures he had sent to my wonderful husband. ?Wow, these are really good pics, what was his reply?? I asked him. He brought up my husbands text message. ?She is getting fucked good! She is so damn hot. Don?t forget to ask her for your turn and I want the fucked pussy when she gets home! Thanks for allowing her to work today!? I looked up at Cap?t and his penis was hard again. I pulled my dress over my head and he took me into the stateroom. He laid me on the bed and O watched him put on a condom. I was rubbing my hands all over my body and was starting to throb again. He leaned between my legs and caressed my tits with both hands. I reached down between my thighs and grabbed his erect cock. I moved it over my wet slippery hole and pushed my hips toward him. His shaft slid right in and he pressed into me with my lips devouring him. We thrust against each other and then he pulled out of me and turned me on my side. He entered me from behind and wrapped his arms around me. We changed positions a couple more times before he sent me into climax. ?Oh Captain? was all I could manage to moan out. He came right after I did and we laid there for a minute.

He said, ?Do you realize it?s almost 9 o?clock and we didn?t have dinner yet?? We both laughed and got up. We got cleaned up and got dressed. I gathered my stuff as he gathered all the bottles and trash. I told him I would get a bite on my way home cause I wanted to get home before hubby fell asleep. He agreed and walked me to my car.

?Oh,? he said, ?Here is the other $400 they paid upfront to have a personal server on board for the day.?

?Holy Crap,? I said.

?So you made, what, close to $1400.00 for the day??

?Yeah, I believe so!? I was amazed. ?Anytime you need a personal server onboard let me know!?

?Well, you have a bachelor party next summer for sure!? he said.

We gave a hug and kiss and he closed my car door. ?Drive safe?, he said.

?Thanks, I will?

As soon as I pulled out of the parking lot I called my husband.

?Hi Honey?

?Hello! So how was it? Cap?t sent me quite a few hot pictures!?

?OMG, you wouldn?t believe how much I made, but too much to say over the phone! I?ll give you the play by play when I get home!?

?Well, tell me about it all when you get here, cause I wanna hear all about it and then I?m fucking that pussy!?

?Can?t wait, love you babe!?

?Love you too, drive safe and see you in a couple hours!?

Click.

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