Great Loop Ch. 04

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Oca 8, 2023 // By:analsex // No Comment

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This set of stories are meant to be read as chapters in a book. If you haven’t read the previous chapters of the Great Loop, I recommend you do to better understand the characters.

All characters are fictional. Obviously, many of the place locations are real.


Looking at the charts, I decided to circumnavigate Lake Ontario in a counter clockwise direction. I’m not sure why. The long range weather forecast showed some storms coming thru the area in 3-5 days so I wanted to stay reasonably close to shore so I could find protection if I needed to. I had three weeks to do the circumnavigation and I wanted to spend about a week in Toronto. I planned to cross from Oswego to Kingston, Ontario and then work my way down the coast of Canada to Toronto, then to Niagara Falls, Rochester, NY and back to Oswego. I planned to spend a few days in Rochester because I wanted to visit the Eastman Museum.

I got a good start to the day. It was sunny and warm and the waves were running about 2-3 feet. I cleared the break water and pointed the boat towards Kingston and got into the routine of the boat. As the day progressed, I noticed a cloud bank beginning to build in front of me. I pulled out the charts and found some islands to the east of me that I could anchor off if I needed to. I’m a cautious sailor and because I wasn’t on a schedule, I didn’t object to taking a day or two longer to get somewhere safely. I also needed to be cautious because I was cruising alone. I continued to monitor the cloud bank until I realized it was a fog bank and it was only about 5 miles in front of me. I immediately turned east to head for an anchorage that would allow me to safely wait out the fog. Rounding a point of an island, I found a sail boat already in the process of anchoring. I picked a point about 75 yards from him and lowered my anchor and put out enough line to assure the anchor wouldn’t drag. I also wanted to be sure that as the wind changed, I wouldn’t interfere with his anchor line.

As I was finishing up getting everything squared away and my anchorage lights on, I heard, “Hey, Mate. Come over for drinks. This bloody soup is going to be with us through the night. My wife’s below making up some snacks.” I was amazed how well sound traveled in the fog. I yelled back, “Be over in a few minutes.”

I motored over in the dingy, tied off and climbed aboard their boat. Looking back at Second Chance, I realized how thick the fog was. I could barely make out the anchorage lights on my boat.

“Hi, mate, my name is Peter.”

“Hi, I’m Jim.”

“Nice to met you James, looks like we’re in for a thick night. Why don’t you go below and get a drink. My wife, Helen, is down there fixing snacks.”


“By the way, she’s naked. She always is when on the boat unless it turns really cold, so pay her no mind. However, if she wants a shag, go ahead and give it to her. She gets horny as ell when she’s on the boat.”

“Huh, are you sure, I mean we just met.”

“No problem Mate, we swing and she likes a good shagging, so help me keep her happy. We’ll both enjoy it.


“Hey Hel, James is coming down to get a drink. Show him the liquor cabinet.”

Peter was right. She was naked. I got a good look at her and guessed she was around 50 with a little grey in her hair. She had the body of someone 10-15 years younger. As I stepped down the companion way she turned, smiled, “Hi James, I’m Helen. Don’t mind me, I never dress on the boat, it makes it easier to fuck when I want to. I suppose Peter already warned you about me and it’s all true. Get a drink, istanbul escort get undressed, lets go up on deck and you and Peter can fuck me.”

I made myself a big drink, took a big swallow, undressed and headed back up to the deck. Helen already had Peter’s cock in her mouth and was wiggling her ass at me. She turned, looked at me and said, “Oh, nice cock. Fuck me while I suck Peter and after you both come, switch places. I love the way I taste on a cock that has just come in my pussy.”

I took another big swallow of my drink, stepped behind her and slid my cock into a very hot, wet pussy. I got a muffled groan out of Helen as I started to pump into her. She was the most orgasmic woman I had ever fucked. On about the third or fourth stroke she started having little mini orgasms and was vocal with every one of them, even with Peter’s cock buried in her throat. I started rubbing my thumb over her rosebud as I pumped into her and that brought even more orgasms and vocalizations. She started vacuuming Peter’s cock as she moved her lips up and down his cock with the same rhythm as my pumping her. It didn’t take long and he blew his load down her throat. As he pulled out of her she yelled, “FUCK, I LOVE COCK. NOW FUCK ME HARDER.” I started pounding her pussy with all I had. Her body started shaking, “KEEP FUCKING ME, I’M CUMMING!” I shoved my thumb in her ass, reached around and found her clit and sent her to the stars. Her eyes were wide, her breathing ragged and I held her body as she continued to shake.

“Bloody ell, mate. What’d you do to her? I’ve never seen her cum like that. That was the most beautiful thing I’ve ever seen. Look at her, she’s still cumming. It’s running down her legs. Beautiful!”

Slowly she returned to reality, looked at me and gave me a major toe curling kiss. Then she dropped to my cock and said to Peter, “Fuck me, hard!” She sucked my cock into her mouth and began trying to get every drop of cum out of my balls. She was like a vacuum cleaner she was sucking so hard. It wasn’t long and I exploded down her throat and Peter dumped his balls in her pussy. We all collapsed to the deck, breathing hard. My cock went limp quicker than it ever had before.

“FUCKING HELL, THAT WAS THE BEST CUM EVER.” How come you never stuck your thumb in my ass, Peter? That’s what made me cum so hard, ohhhh, I need to try a cock up my ass. Maybe later tonight when you guys recover.”

About that time we heard, “Ahoy, that sounded like fun over there. Can we join you?” All three of us were surprised because we couldn’t see another boat.

“Hey, Mate, where the ell are ya?”

“We’re looking at a cruiser. Aren’t you on that?”

“No, that is between you and us. Come on over, but be warned, no clothing allowed!”

We heard three splashes. I looked at Peter and Helen and held up 3 fingers with a questioning look. Helen shook her head yes. A few minutes later 2 women and a guy appeared swimming past my boat and climbed aboard Peter and Helen’s boat.

“Hey, Mates. I’m Peter, that’s Helen my wife, and this is James from the cruiser. Welcome aboard. Now get those suits off.”

“Hi, I’m Phyllis or Phyl as I prefer, that’s my sister Joyce and her husband Jack.”

All of them were stripping out of their suits. They appeared to be in their late 30’s, trim and fit. Both girls had smallish breast, and Jack had a substantial cock. It caught Helens eye immediately.

“As you know, we just finished shagging Helen so James and I are in recovery, but feel free, Jack, to shag her. She looks like she is ready for your magnificence cock.” esenyurt escort

“James, lets get the ladies a drink and get them warmed up so that when we’re ready they are too.”

When we came back up with the drinks, Helen was sitting on Jacks cock and bouncing away. The look on her face was pure bliss. As we handed the girls their drinks, Joyce sat on her husbands face and played with Helens tits.

Phyl came over and sat next to me and made sure her tits rubbed my arms as she reached for my cock and started trying to stroke some life into it. Peter stood next to Helen and Joyce and they took turns trying to suck life back into him. Watching Helen, Joyce and Jack with Phyl stroking my cock, it didn’t take long for life to return to it. Phyl leaned over, kissed me and started sucking my cock. I reached around her tight little ass and found her very wet pussy and started to finger it. Quickly we migrated to a 69 position and began to pleasure each other orally.

I think anyone within a hundred miles heard Helen when she came. She collapsed on Jacks chest and simply laid there. Joyce was sucking Peters cock as she crawled off Jacks face. Phyl pulled off my cock and said,”I need your cock in my pussy, fuck me.”

Turning around, I pulled her legs up over my shoulders as I entered her. What a tight little pussy. It felt marvelous and I took my time as I slowly stroked in and out of her.

Looking over, Joyce was on her hands and knees and Jack had entered her from behind. Peter was balls deep in her face. Helen had crawled over to Phyl and I and was playing with Phyl’s clit. Both girls seemed to cum at the same time, but Phyl screamed out as she came matching Helen’s scream. I looked down. There was Helen smiling with her thumb in Phyl’s ass. At that moment, I dumped a small load into Phyl before sliding to the deck. Helen was quick to clean my cock before moving to Phyl and cleaning her. Joyce had Jack’s cum running down her legs and her face was covered with Peter’s spunk.

It had cooled down considerably and everything was damp from the fog, so Helen and Peter passed out blankets for us to sit under as we recovered. As we sat there, we learned each others story. Peter and Helen lived and worked in Toronto and were out on the boat every weekend. Helen would spend the entire weekend naked and she often walked around their home naked. She said she loved sex, any where, any time, any way. They had a group of friends that they swung with and sometimes swapped partners for a few days at a time.

Jack, Joyce and Phyl were from Watertown, NY. They like to get on the water on the weekends and often played together. Jack and Joyce had gotten married young and were still madly in love but enjoyed spending weekends with Phyl. In the summer, they spent time on the water, in the winter they would go to their cabin in the Adirondacks and snowmobile, ski, and enjoy winter sports. This was the first time they had been in a group sex situation. Phyl had been in a long term relationship, but when it ended, she realized that she enjoyed a variety of men, so she continued to play the field pretending to be looking for Mr. Right. After today, she said, “I want to find a group to play with at home. This is FUN!”

I told them of my business, why the trip and my experiences with Debbie, Julie and Amy. Everyone expressed a certain level of jealousy over me being on a cool vacation for several years.

Since it was getting a little cooler, Peter invited us below where it was warmer. We sort of paired off for the night with Helen and beylikdüzü escort I getting together, Peter with Joyce, and Jack and Phyl got together. We had a few drinks, ate sandwiches and then headed for the state rooms for the night. Helen wanted me to take her ass, but after the days events, I wasn’t able to get hard enough or stay hard enough to satisfy her needs. I did give her several orgasms before falling asleep. Based on the sounds coming from around the boat, everyone was enjoying some form of pleasure.

In the morning, I woke to find Joyce in bed with me. Helen was with Jack, and Phyl and Peter were together. Apparently, during the night, the girls decided it would be cool to wake with a different partner. Joyce gave me a long, tongue filled kiss, crawled on top of me and whispered, “I want a long slow fuck with multiple orgasms, so please don’t feel you have to rush.” As she rode me, I pulled her to me and started with the ears and neck as Holly had taught me. I then progressed to her tits and she had her first small orgasm. My hands continued to explore her body and legs which caused several more small orgasms. With each one, her eyes got a little bigger and her smile brighter. She had a big orgasm when I focused on her clit, but since I didn’t let her stop riding me, we continued letting the big one build. When I sensed it was time, I reached around her, stuck my finger in her ass and we both boarded the orgasmic express to the stars. As she fell to my chest, her arms went around my neck and stayed that way for several minutes as she returned to normal. Then she kissed me again and said, “I love you.”

After a little recovery and a trip to the bathroom, we went topside to find Phyl and Peter. It was still foggy and I could barely see the outlines of “Second Chance”. Suddenly we heard Helen screaming a good kinda scream. Twenty minutes later she and Jack emerged. “Bloody hell, I won’t be able to sit for a week. I had Jack fuck my ass and I had a great cum, but he split me wide open. Damn, I could really get to like having my ass fucked.”

“Well Hel, any of our friends and I would be happy to fuck your ass and your pussy at the same time. We might even make you air tight if you wanted it.”

Helen sat on Peters lap, hugged and kissed him and told him how much she loved him. Jack gave Joyce the same treatment. Phyl kissed me and told me I was a wonderful lover.

We cobbled together a breakfast and then Jack, Joyce, and Phyl found their swim suits jumped over the side and headed to their boat. The weather forecast was for the fog to burn off later in the morning. Peter, Helen, and I had some coffee, talked, exchanged phone numbers and then Helen wanted another session so she sucked my cock and Peter fucked her from behind. When we finished, the fog had lifted considerably. As I was getting ready to go back to my boat, Helen suggested that I call them when I got to Toronto and they would throw a swingers party in my honor. All I could say was “Great.”

As I was taking the dingy back to the boat, Peter and Helen lifted anchor and got underway. As they left, Helen was standing at the bow of the boat, naked and waving to me.

I realized that today was Sunday and I briefly thought about what I would be doing if I were still on Long Island. Probably waking up on the sofa in my office and thinking about what ever parties I had to cater today. I liked waking up with a nude woman next to me on a boat a lot better. Maybe I should sell the business and retire to this kinda life.

As the sun came out, I pulled the anchor and headed for Kingston, Ontario.

After getting tied up at the dock and clearing customs, I walked around the Kingston water front, did some shopping, bought a few groceries, and generally had a nice time. Getting back to the boat, I poured myself a drink, talked with some neighbors and relaxed. Tomorrow, I would motor down to Toronto.

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