Thomas Theodore Randle the Fourth - Cover

Thomas Theodore Randle the Fourth

Copyright© 2019 by islandic

Chapter 6: Sailing Surprise

Erotica Sex Story: Chapter 6: Sailing Surprise - Born into wealth and trying to cope.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/ft   ft/ft   Teenagers   Consensual   BiSexual   Heterosexual   Fiction   Incest   Brother   Sister   Cream Pie   Exhibitionism   Oral Sex   Voyeurism  

I had always loved the ocean and so I loved boats as well. We stood on the wharf and admired the gleaming white hull of the vessel we would be spending the next six hours on. The Captain was the son of one of the owners and would be skippering us with one other crew on our cruise around Long Island.

I’d brought a duffel bag with some items that I thought we might need like sun screen and a change of clothes even a windbreaker if the weather changed. The girls had similar bags and totes with them. When we boarded we were surprised to find that the delivery girl from the other night was the crew and sister to the captain. They introduced themselves as Pete and Wendy. Wendy was Peter’s stepsister and that was the reason for the sixteen year age gap. Pete told us of his experience with being a captain and of the day he had planned out for us. Wendy showed us to our cabins to stow our gear and then gave us a tour of the boat. It was real luxurious and even had a Jacuzzi on the upper deck. Wendy would be our cabin crew and cook. She planned to have chicken or ham salads for lunch with fresh fruit or cheese cake for desert and ice water was available from the mini fridge behind the fully stocked bar. As we pulled away from the dock I would have loved it if were leaving for a longer cruise, say The Bahamas or BVI. One day I’ll get there I promised myself.

The girls quickly settled into the boating lifestyle and stripped down to their bikinis and were lounging on the lower deck in the sunshine. I was in the wheelhouse and Pete was giving me a quick rundown on the running of a boat this size and explaining the technical terms of yachting and navigation. Once we were underway I had a go at being the captain and steering.

Pete told how he was always busy doing charters with the boat and when he was not on the ocean he was with his wife and three kids in Northport. Wendy was single and had a small flat above a Marine supply shop at the docks in Northport but usually spent some of her time attending to the boat and sleeping on board which was good for security reasons and kept up the maintenance of the boat as well. Not too long into the trip Wendy called us all in to the dining room that seated eight and we had lunch. We reached our first port of call and dropped anchor. The inlet was secluded and away from the wind and G race and Eve went up to the Jacuzzi and Mel and I watched as Pete lowered the Jet Ski into the water and after some quick instructions we were off. By the time we had finished we both thought that we had to get one of these. I looked towards the boat and said “I want one of those.”

Grace and Eve were content to lie in the sun so Pete stored the Jet Ski on board and we started off to our next stop. We motored slowly past some of the really big houses along the shoreline and waved to everyone that we could. Surprisingly there wasn’t that much other boat traffic around. Our next stop had us pulled into a wooded cove with a sandy beach and Pete broke out some snorkels and swim fins for us. All the girls wanted to have a go of this so I waited on board for my turn. Wendy, Pete and I sat on the aft deck in the shade and had a cool drink. They told me about their life and how their mum and dad had split up and dad had married again. He was an investment manager of his own firm and she was the daughter of a wealthy Asian businessman. This explains the slightly Asian look of Wendy. Their dad and mum lived in an apartment in New Rochelle and seldom came out this far along Long Island. The boat was owned by a group of businessmen that wanted a tax break of some sort and paid him and Wendy a good wage to captain and manage the boat. Occasionally one of the businessmen would want to be taken out for a weekend on the boat, sometimes with their wives and other times with their secretary’s.

I told them about the recent death of our father and that we were staying at the house in Centerport for a week or two with our mother and as they weren’t too far from our house I invited them to drop by if they could. Peter said he liked to spend his down time with his wife and kids but Wendy would love to drop by soon.

Grace and Eve pulled themselves up onto the swim platform on the rear of the boat and our attention was drawn to their bodies as they brushed off the excess water and adjusted their swimwear to cover their breasts and bum. All males find this small act riveting and I noticed Wendy licking her lips and wriggling in her seat. I wonder.

I decided to have a swim and joined Mel in the water. There was a small wreck towards the shore and Mel showed me a bracelet that she had found sparkling on the bottom. It was nice and seemed to be gold she said excitedly that she’d been searching for the rest of the pirate treasure ever since. When we returned to the boat I noticed that Wendy and Mel in a whispered conversation and the bracelet being passed back and forth. Half our day was now over so we started back. The girls lay on the foredeck with their tops off and their bodies glistening with sun lotion.

As we were underway Wendy sat with the girls and chatted while Peter and I shared the piloting. Peter wasn’t surprised when Wendy took off her halter top and lay down next to Mel. “You have to put up with this view every day, how sad for you.” He joked and I laughed along with him.

We both had to adjust our cocks in our pants when Wendy applied lotion to Mel and Eve’s breasts and then Mel did the same to Wendy. This went on for some time. She was being very efficient and not missing a spot. Wendy came in a one point to get some cool drinks for everybody and we both turned to watch her every move. She stopped with an arm full of drinks in the companionway and said “Men. You’d think you’ve never seen a pair of tits before.” And laughed all the way back outside. A quick whisper to the girls had them all laughing.

As we neared the Dock the girls dressed and returned to their rooms to gather their gear and bring it up top. Peter told us that he owned a 45 foot Beneteau sail boat and that when he had some time off to sail it he’d give us a ring and experience real sailing. Wendy asked if Mel would be interested in helping to crew for the next charter they were taking out the following weekend. It was going to be a short cruise around Long Island Sound and back.

“Oh I’d love to go.” She looked to me and I nodded. She smiled and gave Wendy a hug.

Back home we found Bridie hard at work in the kitchen preparing Dinner. Mother was home and had Connie up in her room helping her arrange her wardrobe and looking through catalogues of dress shops in New York. I said to Bridie that she should bring Bonnie in to help as I suspect that Connie will be tied up with Mother especially if she goes on a shopping trip to New York.

“I rang her at lunch when your mother arrived and whisked Connie away. She’ll be here in the morning with me to help with the rooms and wot-not. She was staying with my family but even I get very tired of all the blarney that goes on with them. She’s happy to help and eager to get away from that lot.” Ha Ha.

Dinner was not too formal but enough to placate mother and ensconce her as head of the household. She regaled us with her friend’s stories of her trips overseas to Europe and the USA. I could see she was excited and suggested that she might like a trip OS, possibly a cruise on one of the big ships. Her eyes widened at the thought and asked us all if we would come along. We explained that we had school and other commitments but we would be pleased to help her arrange a trip. Over the next week she arranged to go on a world cruise on the Queen Mary 2 leaving the big apple for 115 nights and visiting England, Dubai, Hong Kong, Australia and Africa. She was so excited that she went back to the Estate in Portland Maine the next day to organize what cloths to take for such a long and extended tour. She decided to take her friend from Long Island with her as she had some experience with traveling.

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