Captain Jack

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Captain and the two Ladies.
4k words
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Part 1 of the 8 part series

Updated 09/30/2022
Created 12/23/2002
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Life has been good to me in many ways, and yet I am alone. My wife of 25 years is gone after a long illness. I didn’t think I would ever recover, but here I am healthy and in great physical condition for a man of 53. I am 6’2” 225 lb, hair is salt and pepper, I have hazel eyes. I try to keep in good shape, since I was a Navy Seal for 8 years it’s hard to break the habit of running and working out. I have a 65 ft power yacht that I live on and charter out for fishing or just having fun. I was just finishing my morning 5-mile run and was approaching the dock and I spotted two women standing in front of my boat “Good Feelings”.

One of them was a tall blonde; I would say about 5’9”, her hair hung down to her shoulders. She was slender with long legs, which were nicely shaped and a beautiful tight ass. Her breast were rather small, I would say she was a 34 A, or slightly larger. I could see she was not wearing a bra; her nipples were at attention, jutting straight out. She was wearing white short shorts; a powder blue tube top and white low heal sandals. She had the face of and angle, dark blue eyes, frame by her soft ash blonde hair. Her nose was very delicate and her mouth was very sensual, with thick full lips. Her friend was about 5’4” and very petite. Her hair was red and shortly cropped, like a pixie. Her eyes were emerald green; her nose was very tiny and kind of pug. Her cheekbones were high, and she had a set of lips that were full and very soft looking. She was bigger busted than her friend I would say 34C, and a rather small waist that flared into beautifully formed hips. Her ass was like a fine piece of china. She was quite a package dressed in lime green short shorts that clung to her ass like a second skin and a lime green halter-top that was very tight. She was wear a medium heal pair of green shoes. I could see the nipples on her breast poking through the rather thin material. They were the size of my little finger. They had to be at least a quarter of an inch long. They were both smiling as I approached the boat. I was feeling a slight twinge in my groin as I stopped and tried to gather my composure and breathe at the same time.

The red head asked if I was Captain Jack, panting I said yes I was and sat down on a bench that was on the dock. Then she asked if my boat was available for charter, I replied that yes it was, would they like to come on board and inspected the boat.

The redhead held out her hand and told me her name was Sheree Wilson, I shook her hand and said, and I am Jack Nelson. She was still holding my hand and she turned and said, this is my friend Sandra Russo. She nodded and smiled. Her eyes were saying, here I am sweetie come and get me; then I felt Sheree squeezing my hand and I remembered where I was again.

After a tour of the boat we were setting in the main saloon and Sheree said that they wanted to charter the boat for 2 weeks. Looking straight at me and said, the boat has everything we want. She was smiling again, a lusty smile! I said you want the boat for 2 weeks and you haven’t asked what my price is for a day, or a week. Then all of a sudden
Sandra, purr’s; money is no object; we want this boat for 2 weeks name your price. Sheree was leaning forward and sitting with her legs spread, I could see the outline of her pussy lips through the material, shit I was starting to get hard. She caught me looking and she smiled. I though to myself, boy oh boy, two weeks alone with these two will be heaven, yes sire can’t wait.

Then Sheree says, that there would be four people on the boat for the two weeks, Sandra and her husband Joe, and Sheree and her husband Jason. My heart sunk when I heard that and though oh well, easy come easy go.

Sandra was quite the whole time except for the one time she spoke about money being no object. She purred again, do you have a crew and I answered just my cook, who does a lot of other thing also. He is Japanese and he is about 68 years old. I met him in Asia when I was in the Navy. Sandra purred again, how much should we make the check out for?
I said, my rate is usually $800. Per. day, but If I have to feed four people for two weeks it will be$ 1,200.00 per day.

Sheree opened her purse and took out a checkbook and said, what’s the total, I said, that will be $16,800.00. She wrote the numbers in and handed me the check. Can we sail by Sunday, she asked? I replied yes, that would give me 2 day to supply the stores and ready the boat for sea. By the way where do you want to go? She replied, we would leave that up to you, just nice scenery and good beaches. Ok, I said we will sail at 9:00 am. I sat there on the deck watching them walk away. What a sight, two beautiful assess in their own right. What a great set of four cheeks.

Sunday, June 12, 1992

Singhi was in the galley; he was finishing the cleaning and putting away, the stores. I had just finished swabbing the deck and was checking out the electronic systems to make sure the sonar and radar were in working order. I had checked the auto-navigation system yesterday and all was well. We were ready to sail. I was wearing my usual white shorts, white polo shirt and white tennis shoes.

It was 7:30 am, and it was starting to get warm already. I pulled the shirt over my head and tossed it on the navigation table. Damn, I was in great shape for a guy of 53 years. I was still as hard as a rock. I am always told by my friends that I look like I am 33, but I sometimes feel like I am 63 when I think of all the sadness and bad times I have been through. I could see my sweet Michelle lying in her deathbed, smiling at me. I could see the dead bodies of my crew, on our last seal mission, floating in the water off the Korean coast. I could not get these thoughts out of my mind. I was startled back to reality, with hi, “Captain Jack”. I looked and there were the four of them on the dock. I told them to come aboard. The two men were both about 5’10’, the one with Sheree was kind of heavy, not fat but thick, if you know what I mean. He had brown hair and eyes. He held out his hand and Said, I am Joe; pleased to meet you Captain Jack. Sandra’s hubby was older, I would say about my age, very thin and pale, his eyes were sunken and sad brown, his hair was receding and light blonde, white gray taking over. I took his hand in mine and shook it, it was cool and clammy. Wow, what a cool fish for such a hot sexy lady.

It was 9:15 am and we were clear of the breakwater, I looked back and watched the San Diego skyline as it sunk into the horizon. The sea was beautiful, the sun shimmering on the ripples as we cut through the colors on the water. I put the controls on Auto-Navigate and walked to the bow of the boat to watch us cut through the sea. The couples had the two suites on the topside. They were unpacking and relaxing I guessed; but if I were with either Sheree or Sandra, I would be fucking!

I heard footsteps behind me I turned, what a sight; Sheree and Sandra were booth topless. Damn, my jaw dropped and my mouth hung wide open. Sandra’s small breasts were like bullets they stuck straight out, with beautiful pink nipples. They were big nipples the silver dollar size. What a mouth full they would make. They were very firm and did not move much; boy did they look eatable. Sheree was another story her breasts were the size of two softballs, nice and round, her nipples were pointing up and the sky. They were dark in color about the size of a half dollar, I almost reached out and touched them, it was hard not to.

She said, I hope you don’t mind, since you were topless; we figured it was the dress code of the day. I replied jokingly, gee maybe I should take my shorts off too. Sandra purred, yes we would like to see that. Sheree, smiled and said be my guest. My cock was starting to strain at the fabric of my shorts. They both looked down at my crouch and Sheree said, ummmm that looks interesting, she reached down and rubbed her hand across my bulge. Damn, I was in pain. She then asked, is it as big as it feels? Sandra, asked could I see it? I asked were are your husbands. I think they are playing gin or taking a nap was the answer. Sheree by this time grabs my zipper and slides it down and her hand is searching in my shorts for my cock. I feel her hand close around the shaft. She looks at Sandra and says; I think this is a big big boy, smiling. Sandra says, lets see, pull it out. Sheree pulls out all 9 inches of steel hard cock. Her hand does not encompass the shaft. Sandra stares and says, oh I want that, please Sheree can I be first, please.

She reaches down and grabs my cock out of Sheree’s hand, she goes down to her knees and I feel her lips on the head of my cock kissing and sucking just the head. My knees almost buckle, damn she has now got maybe five inches in her mouth and sucking, I can feel her tongue sliding around the head, licking and sucking. I look down and she is trying to take her shorts down, finally Sheree helps her get them down. Sheree then says she will be back in about an hour and leaves. I pick up Sandra and take her to the saloon. I lay her on the couch, she is beautiful, her nipples are as hard as rocks, and her pussy is smooth as a baby’s ass. I could see she is very wet and the juice is running down her ass cheeks as it drips from her large pussy lips. I knee between her legs and smell the aroma of sweet pussy. I put my tongue on her pussy and I feel her shiver with delight. I bury my tongue deep into her pussy and lick and suck, I find her clit and play with it, she closes her legs around my head and she screams, I’m cumming, oh god, I’m cumming, IEEEEEEE…AHHHHH. She exploded, and she kept cumming, spasm after spasm. She grabbed my head and pulled me up to her mouth and pushed her tongue in my mouth and said, Fuck me, please fuck me. She wrapped her long legs around my waist and tried pull me into her. I felt the head of my cock at the entrance of her pussy. I rubbed my cock head up and down her pussy lips; she was begging me to fuck her. I pushed the head into her pussy and I could feel it stretch, she was tight. I pushed again and I slide into her hot velvet tunnel. It felt like my cock was in a vise. She was moaning and she exploded again she wrapped her legs around my ass and pulled me in all the way. She was on fire, she was thrusting he pussy up to meet my cock and she was asking me to fuck her hard and fast. I pull my cock almost all the way out and rammed it back in hard and she meets my thrust wit a thrust of her own. I keep thrusting hard and fast, we keep this up for maybe 15 minutes and I can feel my balls start to get tight, she senses I am about to cum and she starts to have series of orgasms. I can feel the cum shooting up my balls into her pussy, stream after stream of cum. Her pussy muscles were squeezing my cock, draining me of every ounce of fluid in my body. Damn, she just kept the muscles in her pussy squeezing then releasing, over and over.

Finally I rolled off. She sees that I am still hard; so she rolls over and gets on top and slides down on my cock again, and starts fucking me hard. Damn I am so hot, my cock stayed hard and she was fucking me like a bitch dog in heat. She was having orgasm after orgasm. I look up and there is Sheree watching us fuck. She says; my god you have been fucking for over two hours, save some for me Sandy and she walked away. After almost two hours of fucking I was exhausted and she was still wanting more. I pulled on my shorts and told her to get dressed and went down to take a shower.

The hot water felt good, I just let the stream of water hit me in the chest and soaked for the longest time. Sandra was so hot I was getting hard again just thinking about her. She sure loved to fuck! I turned off the water and stepped out of the shower. I threw my terry robe on and dried myself. I then dressed in a pair of white shorts and my tennis shoes.

I went back on deck to check the navigation system; everything was functioning properly and we were right on course. In two hours we would be about 10 miles shy of Ensenada Mexico. We will spend the night in a small cove with clear water about 30 feet deep. The cove is surrounded by mountains and a beautiful white sand beach. Singhi wanted to know what to fix for dinner that night. I told to ask the guests and he disappeared around the corner. The sun was getting lower in the sky and soon the water would be painted in a beautiful palette of colors, reds, orange, purples and yellows. The one constants of the sea is that its always every changing and beautiful.

Hi, I heard and looked to my right, there was Sheree entering the bridge. Hi back at you Sheree, I replied. Do you think you have anything left for me? She said, with a big smile. Her nipples still pointing to the sky as she rubbed against my arm. Damn, this little pixie was getting my cock to stir after all the exercise it had this afternoon. I sure hope I do, I heard myself saying. She said I have something you can take to help you stay hard for a long time and maybe even make your cock a little bigger. Really, I replied what is it Viagra? No, it’s a product that my husbands firm has developed in competition with Viagra. Is it dangerous? For me it is, she said, because it will keep you hard for hours so you can fuck me all night. She had a big grin on her face. I asked what will your husband be doing while I am fucking you all night. Her reply was, I could do as I please; the only thing that he might want is to watch you fucking me. I reached down and cupped her breast in my hand; she got on her tiptoes and kissed me. Her tongue pushed into my mouth, searching and probing, her arms were around my neck. Her nipples were burning holes in my chest as she rubbed them into me. She pulled away from my mouth and handed me a pill. I looked at it and it looked harmless. I opened my mouth and tossed the pill in and swallowed. She ran her hand over my cock and smiled. Sandra said, you are the best she has ever had and she’s had them all, with a laugh. Well I guess I better get ready for dinner and she left me with my thoughts of the night to come. I had Singhi bring my dinner up to the bridge so I could be alone for a while and check the charts again. We should be anchored at Cabo Blanca by 6:00pm, just a little off schedule. Then in the morning we head into to Ensenada for fuel and head down the arm of Baja California.
I was setting there wondering just how that pill would affect me? Would it really help? Would it make me bigger? I thought to myself hell I’m big enough already. Well, we will just have to wait and see.

After dropping anchor I just sat and watched the beautiful scenery around me, a paradise of sand and water. Everyone had eaten and they all came out of their cabins. The men went to saloon and read for a while, then went back to their suites. The women were still topless and Sandra still had that fuck me look in her eyes. Sheree just smiles and blew me kisses. I was starting to feel the blood rushing into my cock. Sheree said something to Sandra and got up and walked back to her suite. I watched Sheree walk toward me her breast swaying and moving with the boat. Her nipples were erect and looking for attention. She was wearing a wrap around short flowered skirt. She walked toward the saloon and waved me to come with her. She turned and pulled on the skirt and it fell to the deck, she was nude and what a sight. I followed her in and she stood there with her arms open, I walked into them and they closed around me. We kissed, her tongue probing my mouth her breast buried in my chest. I could feel my cock growing; she was rubbing herself against it. I reached down and slid my zipper down she grabbed my shorts and pulled them down.

My cock sprung out and she kissed it on the head, she was holding it with both hands. Her tongue started at the tip and worked it way down the shaft and back up licking all the way. She then took the head into her mouth and sucked and licked, then she started sucking my head in and out of her mouth like it was in her cunt. Oh, what a feeling, my cock was like rod of stainless steel. I could feel my cock slide further into her glorious mouth. She had almost all of it in her mouth; I could feel her throat massing the head of my cock. I was so hard I though my cock would burst through the skin. My cock felt bigger than I every was before. Watching my cock slide in and out of her mouth was so erotic, it started my cock to quiver and I knew I was going to cum. Sheree felt me and started sucking harder. When I shot the first stream; it felt like my balls exploded. I kept shooting stream after stream and she swallowed every drop, she kept sucking till there was not a drop left. I could not believe that my cock had not lost any hardness, damn. She was kissing the head again and she said, I want that big cock in my pussy. I threw her on the couch and spread her legs and kissed her pussy lips, they were wet with sweet nectar. I found her clit and sucked it into my mouth. Then I started fucking her with my tongue and she was fucking back and she had an orgasm. She was having a wave of orgasms, one right after the other. She whispered please fuck me with that horse cock.

I looked down at my cock and it looked like a telephone pole, it was massive. I pushed her back on the couch and grabbed her ankles and put them on my shoulders. I pushed into her so my cock was resting between her pussy lips. I kissed her nipples and pushed my cock all the way into her cunt with one thrust, hard and as deep as it would go. I could feel my balls slap her ass. She looked into my eyes and smiled. I was like a mad man I started ramming my cock into her cunt with every ounce of strength I had and she was fucking back as hard as she could. I could feel her cunt opening and closing with every stroke. We fucked like that for a half hour, and then she pushed me on my back and squatted over my rock hard massive cock. Down she went and in went my cock to the hilt. She was riding up and down like a yo yo, riding hard she leaned into me and I was sucking and biting her nipples. Her eyes were closed and her head back again, and she was fucking for all she was worth. I could feel her starting to cum again, she screamed and started to cum, she was moaning and she could not stop cumming. It was so intense that she made me cum also. It was great, I came so hard it hurt and I was shooting rope after rope of cum into her pussy. And she was still riding and fucking with everything she had. She started to slow down, she was still impaled on my cock just sitting on it and flexing and releasing her muscles. God, my cock was in heaven. She finally stopped and rolled off to rest.

She got up and said I’ll be right back. She disappeared through the door and in three minutes she came back. My cock was still as hard as when I started fucking. She grabbed my hand and led me to her suite. When we entered her husband was not there. I asked where is Jason. She said he is sleeping in the saloon tonight, because we need this bed for the rest of the night.

She was like a cat. She stretched out on the bed legs spread and knee up in the air. She reached for my cock and smiled. Mmmmm she muttered, still hard as a rock. This was crazy; my cock was so hard I think it could have cut glass with it. I looked down and saw her pussy lips open, I pushed her legs further apart and drove my cock all the way in to the hilt. We just lay together with my cock buried deep into her cunt. I could feel her working her muscles again. Then I slowly started stroking in and out and she was probing my mouth with her tongue. We fucked like that for what must have been about and hour, in which she was having orgasm after orgasm. I could feel my cock start to pulse and my balls tense. I can’t believe how hard I came. I could finally feel my cock start to soften and I rolled off of her. She reached over and took the clock in her hand and adjusted it, and said, I set the alarm for two hours. She smiles and said rest my darling, because were not through for the night!

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