Island Sisters

Literotic asexstories – Island Sisters by Toro1,Toro1 Widower descends into love and debauchery with two sets of sisters.

Griff is recovering from a tragedy that took his family and rediscovers love with two sisters and then some.

Many thanks to kenjisato, who is my editor, and made this better in every way. Any mistakes here are my own.

If you have comments, please add them, and consider favoriting the story or even following me. I appreciate the feedback and interest which keeps me writing. I have used many of the comments to improve my writing or as ideas for future stories.

This is my submission for the Nude Day story contest. Please rate the story to help me in this contest if you like it.

As is customary with my stories, I listed a porn star who approximates the physical image of the character. It is listed at the end of the story, as many readers may want to use their own imagination.

All characters are 18 years of age or older. This story has themes that involve group sex, mild domination, lesbian sex, and anal sex.

Chapter 1: Aftermath

Something had to be done. I needed a change of scenery, a new place, anything to get me out of this funk of sorrow. I kept seeing my wife of twenty years driving with our daughter and getting hit by that detached truck wheel which killed them instantly.

The driver and trucking company were shown to be deficient in safety inspections that were required. It resulted in a large insurance settlement that allowed me to step back from work to settle my affairs.

After dealing with all the arrangements, I found myself alone in a house that was packed with memories that continually made me sad. Work seemed meaningless without family to support. Neighbors and old friends provided some help, but were busy with their own lives. Some wanted to provide more than support, as evidenced by all the casseroles, invites, and finally propositions from female acquaintances. They all fell on deaf ears. I wasn’t prepared to start a relationship.

I decided to get out of my small town and head to the family cabin. It was a four-hour drive north, and located in a group of islands at the end of Lake Ontario called the ‘Thousand Islands’. I had spent the summers of my youth there. As a family, we had been part of the community for years.

All the cabins were boat-only access. You would think that this would limit the sense of community, but that wasn’t the case at all. Families had been going there for generations, and everyone spent time socializing and helping each other out. Having a place on an island made us more social, not less.

We’d bought out my brother a few years back, as he was working abroad and couldn’t use the place.

I got there in late June. The water was starting to get warm, and families were starting to filter into their islands.

People think of cabins as great places to relax. They are, but do require significant work every year. The elements take their toll. Wood rots, and the winter ice will ravage your dock.

At first, I just completed the litany of small jobs that were required to open the cabin. I’d always been handy, as I learned it from my dad who’d passed shortly after my mom a few years earlier. It was what inspired me to go into engineering as a profession. Some engineers are useless with practical tools; my upbringing ensured that I was at least reasonably capable.

Doing physical work and solving small issues was a tonic for my soul, and was getting me through the worst of my grief. I contemplated a larger job on the cabin, and decided to tackle enlarging the deck. It would take me about a month to complete and keep my mind occupied.

My office had been enquiring about my return. I told them I was taking at least the summer off. I wasn’t sure if I’d have a job to go back to, but I didn’t care. The money from the settlement would cover me for the foreseeable future.

Summer residents started arriving and I would then see more boats buzzing past the cabin. Many stopped to offer their condolences.

In early June, Walt, who had a place a few miles away, stopped at my dock. “How is the deck building going?” Walt asked amiably.

“Pretty well, as long as I don’t run short of something and have to make the trek to the hardware store,” I replied.

Going into town to get anything required a boat ride to the marina and then a drive to the store. It could easily be two to three hours for a round trip, and was a common destroyer of time.

“Always come over to see if I have it,” Walt offered kindly. “I’ve a well-stocked tool shed and would be happy to save you the time.”

Walt and I discussed my project further. He had some great practical advice on putting a layer of plastic on the beams to stop water from rotting them out. It was good to talk to a friend about something other than the accident.

“I’m doing a project of my own,” Walt mentioned. “I’m replacing some of the wooden face boards that have finally given out to weather. I could use some help in a week in getting them up. They’re hard to get level without an experienced set of hands. My daughters are coming up in a few days, but they generally don’t concern themselves with maintenance projects.”

“No problem,” I offered. “It would be good to do a job together and I am in need of some social contact, now that I am up for it.”

Walt looked at the ground, and quietly said, “We’re all devastated for your loss. I’m glad this place is working to help heal you.”

“It’s helping to be here, being around people who genuinely care,” I said, as I put my hand on his shoulder to acknowledge the sentiment.

Chapter 2: Sisters

A week had passed, and I headed to Walt’s place to help him with the facia. As I pulled up to his dock in my ‘tin can’ boat. It was an old aluminum boat with an old fifteen-horsepower outboard on the back. I was greeted by both his daughters, Holly and Hailey.

Holly was in her late thirties, about five years younger than me, and Hailey was thirty. They were both stunning in different ways. I knew Holly from when I was younger. She was tall and lithe with long red hair that was always in a French braid. Her skin was white with a dusting of freckles. She sported yoga attire which showed off her toned body.

Hailey was shorter than her sister, and had long blonde hair that was a loose mess of curls. She was always tanned and tended to wear loose muscle shirts over a bikini, which showed off her round boobs above an equally toned, but slightly curvier body.

Holly had two daughters who were just younger than my daughter had been. She came up to the cabin most summers with them, and was only periodically joined by her husband. I had known her all my life. She had kids earlier than me, but the closeness in age of her daughters meant that we saw a lot of her most summers. Hailey, on the other hand, was the rebel of the two daughters. She was known as more of a free spirit in the community. Various boyfriends appeared and disappeared each year.

They both grabbed the lines from my boat ,and fastened them to iron rings on the dock. I grabbed my tool box and jumped onto the dock. Both women gave me meaningful hugs and expressed their sympathy.

“Walt sent us down to help you,” Holly said. “He was feeling a bit winded this morning.”

“I can always come back,” I offered.

“No, he has been looking forward to this,” Hailey said. “He gets tired of just talking to women all day, and we need to hear something else other than all his business stories.”

We went up their path to the cabin and found Walt pulling off the rotten boards from the front of his cabin. Their cabin was much larger than mine, and featured an incredible view of other islands and the sunset. His family had been here for generations, and they had a grand old place.

We quickly got to work helping Walt. Holly and Hailey proved to be very helpful and were quite capable on the work site, which didn’t fit with Walt’s assessment of them earlier that week.

We finished the tear down of the old boards and then sealed up the wall with that paper that protects buildings. We were running out of light when Walt called it quits, and demanded that I stay for dinner, which Holly had prepared.

Over dinner, I got updates from both girls.

“Is Mike making it up here this summer?” I enquired.

“I don’t think so,” Holly said with a frown. “He has a computer project in California that will keep him away.”

“That’s too bad,” I said. “Are your girls making it here soon?”

“Kylie will be here in a week,” Holly said. “She has a modeling gig in New York that should wrap up by the end of June after her freshman year. Kelly will be here shortly after that. She is finishing up a dance recital with her team after finishing her senior year in high school.”

“What are your plans this summer?” I asked Hailey.

“I started a new career last year doing photography and graphic design,” Hailey said, with some pride. “The work allows me to be here for the summer as it is all online and with the advent of Starlink, we now have great internet.”

“You ladies were a great help today,” I said, sincerely. “You pitched right in and had good ideas for the work.”

They both glowed from the compliment, and I could see the pride on Walt’s face.

We ended up playing euchre for an hour after dinner, which is a four-person card game. I was paired with Walt and the girls were with each other. The conversation was easy and relaxing with these old friends.

As the evening wrapped up, I made plans to come back in two days to help with the next stage. I didn’t think that Walt actually needed the help, his daughters were competent workers, but I’d genuinely enjoyed their company.

Chapter 3: Deck Help

The next day, I had to start putting down the decking. As I was setting up the boards, I heard a boat approach my dock. I went down to find that Holly and Hailey had arrived and wanted to return the favor and help me with my project.

“You need to keep helping your dad,” I argued.

“He said he needed a break day, after yesterday,” Hailey claimed.

“Well, that is very kind of you,” I said, with meaning.

We got to work laying the deck boards. They were both helpful in handling the long boards and ensuring spacing. I taught them both how to use the nail gun which they picked up quickly.

“How about breaking for lunch?” I suggested.

“Sounds great,” Hailey said, as she wiped sweat from her brow. “I think we should all jump in the lake prior to that, though.”

Holly and I both agreed, and we ran down to the dock to take the plunge into the refreshing water.

Watching them climb the swim ladder was causing some stirring down below. Hailey seemed to detect my glance, and responded by giving her bum a wag as she climbed the ladder onto the dock.

I took a moment to calm myself, as I was wearing swim jammers that were skintight. I’d been a competitive swimmer in college, and still did laps at home, and distance swims at the cabin to stay in shape. As I climbed the ladder, I gave the exaggerated bum wag that Hailey had done.

Hailey made a wolf whistle which earned her a splash from Holly, who was more uptight.

“Griff earned that,” Hailey said, in her defense. “He was checking us both out when we climbed the ladder and I saw your eyes lingering, as well. I just articulated the feeling.”

Holly was blushing, having been caught by her sister.

Hailey took it up another level when she said, “While I like looking at his ass, I am even keener when he faces us. Those shorts leave nothing to the imagination.”

Holly kept silent and we moved past the awkwardness and proceeded to dry off with towels that helped conceal my growing problem.

I pulled together a quick lunch which we accompanied by a beer.

“We’ll head back after we help with those last boards,” Holly suggested. “Dad didn’t seem well this morning and I want to check on him, and try to give Mike a call. How about joining us for dinner again tonight, and another round of cards?”

“That sounds like a plan,” I said.

“Calling that loser isn’t worth your time,” Hailey chided.

Holly gave her sister a withering look, which ended her teasing about what had to be a difficult situation.

Chapter 4: Revelations

I noted that Walt didn’t finish his dinner that night. He said that he still wasn’t feeling well and had talked to his doctor that day.

“I am going to have to head back home to get some tests,” Walt said. “Getting old sucks, but it is better than the alternative. We’ll have to put my project on hold.”

“I think we can finish it up,” I offered, looking at the girls, who were nodding their agreement.

“That is great,” Walt said. “They are really showing ownership in the place. Grif, thanks for all your help.”

“No issue, Walt,” I said. “Holly and Hailey really helped me out today. I am ahead of my plan because of them.”

Walt retired early and Hailey suggested a night swim. “It is a clear night, and stars are amazing when lying on your back in the cool water,” Hailey said.

I shrugged my shoulders and agreed. I didn’t have any trunks with me, but could just go in my underwear. Holly agreed, and we all headed to the dock.

We got to the dock and Hailey started stripping. “There is only one way to do a night swim,” she said, as she stepped out of her underwear and bra and then jumped in.

I had my shirt off and decided there wasn’t any harm in going nude.

Holly had made the same decision, and I was treated to a view of her lithe, alabaster body which almost glowed in the starlight.

We treaded water on our backs to take in the Milky Way.

“That is Orion’s belt,” Holly said, pointing to three stars.

“There is the Little Dipper,” I said, pointing to a group of stars.

“I am more interested in the Big Dipper,” Hailey said, as I felt her hand grasp my semi-erect cock.

I recoiled in surprise and Holly could tell what happened.

Instead of admonishing her little sister, Holly said, “I hear dippers hold cream. Should we find out?”

This earned a double take from Hailey who wasn’t used to her sister not being so uptight.

“What happened on that call with Mike today,” Hailey asked her sister with concern, as she removed her hand from my groin.

“I’ve had a very big day,” Holly said, with watery eyes. “I did some searching on the conference that he was attending. The conference was moved out by a month, so he clearly wasn’t in San Francisco for that. I did some more searching and saw that there was a big get together for the LBGT crowd.

“I browsed the photos, and saw one of Mike wearing women’s clothing. I confronted him with this on our call, and he came clean saying that he wanted to pursue a different lifestyle.”

“Oh my god, Holly,” Hailey said. “I know that I tease you about him, but that is so sad to hear.”

“Honestly, I am happy that there is a reason for his distance,” Holly said, with her voice cracking. “I don’t have to feel responsible for it.” Holly had tears running down her face that reflected in the moonlight.

I reached out and gave her a hug, which she reciprocated.

Hailey did the same, and said, “I’m sorry for my teasing about him now.”

“Don’t be sorry,” Holly admonished. “Your comments are what led me to doubt him. I feel totally liberated now, and must think about breaking this to my girls.”

We all got out of the water and towelled off and donned our clothes in silence.

“That’s some heavy news,” I said, with empathy. “Do you want a break from work tomorrow?”

“No, doing these projects has been a good distraction and a great way to spend time with people I care about,” Holly said, with emotion in her voice.

Hailey gave Holly another hug, then Holly came to me, and held me tight.

“I feel the same way about spending time with both of you,” I said, honestly. “Losing my wife and daughter has been devastating. Doing work with friends has helped heal me.”

I came away from Holly with tears in my own eyes, and Hailey came to give me a hug, as well.

We all looked at each other with sheepish smiles. What a night of revelations and honesty.

Chapter 5: Alone with the girls

I arrived the next morning to find Walt and Hailey loading their boat, so she could take Walt to the marina.

“How are you feeling today?” I asked Walt.

“Still looking at the green side of the grass,” Walt said with a smile. “I do feel better, but want to get this looked at. I’d a kidney issue a few years ago, and want to catch it early if it is the same problem.” After a pause, he said, “Grif, look after my girls while I’m gone, and don’t take any lip from Hailey.”

“I’ll do my best,” I promised. “Take care of yourself.”

Holly and I went up to the cabin and I prepared to get to work.

“Want a coffee?” Holly offered.

“Sure,” I responded. “I take it black.”

Holly came out with two steaming mugs.

“Thanks for your empathy last night,” Holly said, as she emphasized herself by touching my shoulder.

“We have both had some tough times,” I said. “Better to go through those with friends.”

“Hailey has had some shitty times with boyfriends, as well,” Holly said. “She hides it behind her flirty exterior, but she hasn’t been treated very well, either.”

“I don’t understand most guys,” I offered. “How could they treat you both so poorly.”

“We are both drawn to strong male figures, like my father,” Holly said, insightfully. “Unfortunately, many of them are faking it, or abuse the trust that’s implied.”

“That is very insightful,” I offered. “I guess that you have to keep trying to find the right person.”

We were interrupted by Hailey’s return, as she bounded onto the deck.

“Are you two being all mopey this morning?” Hailey said.

“No, just having a really good conversation,” I said, as I stood up and headed to my toolbox.

The siding went up quickly over the day. We all swam at lunch with each of us making a show of climbing the swim ladder.

Hailey took it up a notch. She was sitting on a pool noodle in the water and said, “I can think of something else that feels better down here that isn’t plastic.”

“Oh, you should be used to plastic by now without a boyfriend for the past year,” Holly teased her sister.

“I’m not the only one riding plastic in this family,” Hailey retorted.

“Ladies, you are going to have to calm down, or I am going to have to ignore your father’s advice of not taking any lip from either of you,” I said, with a grin.

“Oh, I can give you some lip,” Hailey said with a grin, and tried to reach for my crotch.

I batted her hand away and shook my head. What was I thinking, egging them on. I headed back to work, and we finished the siding.

Both girls took the opportunity to make more physical contact with me throughout the afternoon in little ways.

Hailey made dinner for us all, and I then excused myself to get back to my cabin before I initiated something I might regret later.

“Don’t leave us alone,” Hailey implored.

“You always have your plastic friends,” I teased, as I headed to my boat.

Chapter 6: Proposal

Back at the cabin, I poured myself a scotch and contemplated life on the couch. I was feeling close to both girls, and they both seemed to reciprocate, each in her own way. Holly was more reserved and thoughtful, while Hailey had playful energy to burn.

I was worried that going further would ruin my relationship with their family and cause hard feelings with the other sister, if I started a relationship with one of them.

As I was thinking this through, I heard a noise outside. Sure enough, the sound of footsteps on the deck got louder, and then Hailey and Holly busted through my door in their pyjamas with a half-finished bottle of wine.