Sailing Sweethearts

by Tony Tiger

Caution: This Sex Story contains strong sexual content, including Mult, Teenagers, Romantic, Fiction, Polygamy/Polyamory, .

Desc: Sex Story: Photographer takes two honeys for quite a sailboat trip.

My neighbor’s two daughters have gone from giggling girls to young women during the time I’ve lived here. We’ve always been friendly since I even babysat for them when they were younger. They’re always welcome to use my swimming pool and I’ve enjoyed watching their young bodies develop, especially with the swimsuits which kept getting briefer and briefer as they matured.

I’d gone half with a friend on a 35-foot sailboat in a big lake about an hour away. It had been years since I’d been able to enjoy that relaxing activity and it was delightful. A boat that big can be sailed by one person but it really helps to have at least one other crew. I got the idea to involve the neighbor girls. Besides having the energy of youth, they would really improve the appearance of the boat, especially in warmer weather. [grin]

We started out in the spring and they spent some time learning how sailboats worked and the basics of navigation. They weren’t just going to sit there like on a powerboat but be actively involved in whatever needed to be done. They loved it and kept asking me when we could go again.

The young women didn’t even look like sisters. Kelly, the older at 19, was taller and slender with what I estimated were b-cup breasts. She was a brunette who kept her hair cut short and neat. Molly was a year younger and almost the opposite, barely 5 feet tall with nice c-sized jugs on her chest. Long blonde hair and the curves on the rest of her body were proportional to those upfront.

We usually got an early start on a weekend day and wouldn’t get back until late that night. On the first couple of outings the gals were asleep in the car before I even pulled out of the marina headed home. They built up their endurance though and rapidly became very good deck hands.

We were into early summer now and they asked to do an overnight. I reserved the boat for Friday night and Saturday. We looked at the chart and decided there was an anchorage on the lee side of a small island about two hours sail distant. We got underway quickly and had brought a shrimp pasta salad that we could eat as we sailed.

We found the anchorage in the early dusk and they learned how to secure the boat on a hook (an anchor). It was a clear night and we were far away from city lights so the display of stars was dazzling. We sipped on rum and listened to quiet music and enjoyed the spectacle. Finally they gave me a kiss good night and headed for the vee berth in the bow of the boat. I took the one in the stern.

The water was pretty warm so in the morning we swam to the shore of the island and walked the beach all way around it, looking for shells and interesting driftwood. It gave me great joy to watch the delights that these young ladies were experiencing. Sometimes if they bent over in front of me, though, I had to kinda steer my thoughts away so my swimsuit didn’t bulge too much.

After lunch they wanted to work on their tans and Kelly shyly asked me if it was okay for them to take their tops off. I tried not to jump for joy at that suggestion but just acted rather cool about it. It was fine when they were on their tummies but when they turned over I had to look away and admire other scenery. I was doing just that when Molly quietly came up beside me to ask me something and noticed the front of my swim trunks. Her giggle alerted me that she was there. When I turned my head I saw where her eyes were fixated. She grinned and blushed.

I smiled and said, “I may be older but I’m not dead. Please take that as a compliment.” She nodded and went back to sunning but on her stomach. I saw the sisters whispering. They stayed topless the rest of the day even through dinner and kept glancing at my crotch to see if I was reacting.

I guess it became sort of a contest for them and when we sat out in the cockpit to watch the sunset they brought a blanket and snuggled close to me with it wrapped around all of us together. I had on a T-shirt and they seem to make a point of rubbing their breasts on my arms whenever they moved around. Of course I was erect and I excused myself to go get beverages. I decided to serve us all some wine and made sure that my cock was visible inside my sailing shorts as I returned in the fading light. That made them giggle.

When I finished my wine, they were still working on theirs so I put my arms around their necks, over their shoulders, and cupped a very different breast in each hand. Molly was just taking a sip of her wine and almost spit it out in surprise but I got no objection. I just held them quietly and gently to see what would happen next.

As a team a female hand from either side descended upon the outside of my crotch. They sorted out who would hold the top half and who would get the lower part. My pecker twitched and I know they felt it. We stayed that way quite a while, enjoying this new level of intimacy. When it finally started to get chilly, we went below and prepared for bed.

In order to minimize the load on the holding tank I usually peed over the side when possible. As I went up top to take care of it, Molly followed me and asked timidly, “Can I help?”

I immediately replied, “If you don’t make it so hard I can’t let go, then you’re welcome to.” In the light of the rising moon she watched, fascinated, as she painted patterns in the water with my stream.

“I wish I could to that,” she muttered.

“I’ve known girls who did,” I said with a chuckle. “I’ll show you how tomorrow if you’re brave enough.” She gave my pecker a couple squeezes and then let it go.

I had coffee made and was sitting up in the cockpit enjoying the sunrise when Molly appeared in the loose T-shirt and baggy shorts she slept in. “You promised me some peeing lessons and I can’t hold it any longer.”

She pulled down her shorts and I positioned her in kind of a bent over crouch with her ass between the safety lines over the side. She complained, “I can’t let it go!” I urged her to relax and finally saw the yellow stuff dribble and then turn into a stream shooting out several feet. She was grinning like mad when she finished and pulled her shorts back up.

I laughed, saying, “You are real sailing wench now. I’m so proud of you.” She beamed.

Kelly came up from the cabin rubbing her eyes and wondering what was going on. She laughed when Molly told her the new skills she’d acquired. Sibling rivalry kicked in and she put on a little show for me as she emptied her bladder.

We could only stay here until noon in order to get back to the marina on time. I’d had several cups of coffee so when I had to pee Kelly insisted it was her turn to provide guidance. Molly watched intently.

The young women were getting very comfortable with me as our play had been essentially nonsexual. They decided to get an allover tan and said I should too. Molly complained that I’d been hiding my object of interest while they’d been showing theirs. I suggested we skinny-dip for starters and they thought that was great fun. The cool water also wilted me a bit. I didn’t last long when they got back up on deck, dried off and I got some great pussy shots as they sunned.

I got lots of hugs back at the marina and even a couple of thank you kisses saying that they were ready to do that again anytime. We looked at our calendars and decided we could in two weeks so I reserved the boat again.


We decided to head back for the same anchorage that we were familiar with and their tops came off as soon as we were out of the harbor. It seemed that nudity, whenever comfortable, was going to be the dress code on board. Or I guess, undress code. I was kinda getting used to this and my pecker behaved itself, just filling enough to not look puny.

There seem to be more chitchat between the sisters that I couldn’t overhear so I just concentrated on when I was doing. It was now protocol for me to have a helper when I peed over the side and when they did I was asked to wipe them. I gave a few extra dabs with the paper before I removed it which produced some charming giggles.

We hiked around the island again, this time naked and only carrying towels in case, for some reason, we had to cover up. Kelly’s bowels hadn’t been ready earlier so she had to stop and dig a little hole in the dirt, squatting over it to take her dump. She tried wiping herself with some leaves but I suggested she just rinse off when we got back to the water. We were getting pretty damn comfortable with one another and I know we all liked that.

That evening, after watching the sun go down together, Kelly said she was tired out and was going below. Molly snuggled up to me and asked if she could discuss something personal. With my approval, she continued, “I have a boyfriend that I have sex with, and I did it with the one before him too. I’m telling you that so you realize that I understand what I’m going to ask. To make it real simple, I’d like to have sex with you right here and right now.” She reached down and felt my pecker inflate in her hand. She stretched up to kiss me and commented, “Part of you seems to be interested in the idea. What about the rest?”

“Well,” my surprised reply began, “You are very attractive and I haven’t been getting any for a while and we get along well, so why not?”

She gave a quiet squeal and bent down to engulf half of my cock in her mouth. Damn that was good! She knew what she was doing and even though I warned her she got a mouthful which she swallowed and then kissed me. “Now you’ll last longer where I want you next!”

I put a towel down on the longer side of the cockpit and she laid back in the classic welcoming position. She moaned and whimpered as I tongue lashed her lightly furred twat until it was good and wet and then buried the erection I hadn’t lost. Her hips rocked back in time with my thrusts and she came, wrapping her arms and legs around me tightly for a short time. I kept moving again as soon as she relaxed and when she felt me swell up and pulse my cream into her, she came again.

We lay together quietly for a while, kissing each other’s necks and enjoying the afterglow. She joined me in the aft cabin for the rest of the night and that’s where Kelly found us.

She didn’t seem surprised and made no comment so I figured the girls had been communicating before it happened. So what would be next, I wondered? After lunch Molly said she was going to take a nap and that left Kelly in the cockpit with me. She wanted to talk so I got agreeable.

“I heard you guys last night and Molly said she had a wonderful time. Even though I am older than she is, I’m still a virgin. It’s not a matter of fear, but rather not finding a guy that seemed right for me. I know I’m not built sexy like my sister, but do you think I’m attractive enough to fuck?”

“If that’s an indirect way of asking me if I would get naked with you, the answer is yes. Sexy is a lot more than appearance. Attitude and enthusiasm probably count for more.” We talked for probably an hour, asking each other questions until I stopped her, “Kelly, I think I can make it a good experience for you and I wouldn’t want anything less for a friend. It’s your choice to go below or enjoy your first man up here in the daylight.”

She grinned and said, “Anybody can fuck in a bed or in the dark, but I want this special time to be in the sunlight and the great outdoors! I’m ready!” I arranged the towels again in the same spot that Molly had been last evening, took off the few clothes she was wearing and removed mine also. She was unsure how to start so I laid her back, gave each of her nipples a few moments of oral attention and headed for the Y. From all the noise she made I figured that Molly could hardly be napping and was probably diddling herself listening to what was going on. I later found out that’s exactly what happened.

I stood by her head so that she could explore my equipment with her hands and mouth for little bit and then I position myself between her legs. I encountered her hymen, the first one I’d ever experienced, and pushed through with a little yelp from her. That quickly turned to moans as I used every bit of my experience to pleasure her. When she began begging for me to cum inside her, I complied with her wishes. As we lay quietly together, both descending from our peaks of pleasure, we heard Molly clapping softly, her torso in the hatchway to the cabin.

She brought us all a glass of wine and we toasted Kelly’s new womanhood. Molly reminded her sister that it was her turn next with me and wondered how long it would take me to recover.

I laughed and said probably not too long depending on how much attention my pecker got. Next time I would get a prescription for Cialis. Kelly smirked and said “Who says there’s going to be a next time?”

I grinned back and said, “Ask your sister how addicting sex is. You are going to want me all the time now. I just hope you don’t become a nuisance!”

That statement was a bit of foreshadowing since Molly had a boyfriend, soon to evolve to two, to bang her but Kelly didn’t. I was her outlet and she visited me every day for a while then it tapered down when she got busy at her job. She wanted to spend entire weekends with me which was awfully attractive but I was rather used to the freedom of being single so we had to set some specific times for her to visit and get her horns clipped.

The fact that I had a vasectomy was a big benefit in all this. Molly was on birth control but Kelly wasn’t.

For the summer we pretty regularly took the boat out overnight every other weekend. Molly’s boyfriends wondered why they were never invited and were told it was a family outing and there wasn’t room for anyone else. I did get the prescription and it really helped but I was a tired dude when we tied the boat up again. That is not a complaint, I want you to clearly understand. For a guy in his 40s to have two young women bouncing on his boner that much is like a miracle.

They were welcome in my bed anytime between outings, of course, and took advantage of it frequently. Molly got a kick out of slipping into my bed after a date with a boyfriend and offering me seconds with the option of the erotic details about the current wetness in her pussy. I got to enjoying seconds.

Kelly’s sexual aura had changed and she began to get more interest from younger men. Although happy with our sex life, she wanted some social companionship that I couldn’t provide, much like her younger sister had with her boyfriends.

We had some serious talks about screening good candidates and proceeding slowly towards intimacy. She needed reassurance that I was OK with her exploring sex with others because I was very important to her. The best answer to that was reminding her how she felt about my sex with her sister. That reassured her and she wanted to know if it was OK to share her experiences. I told her that it would probably be a turn-on like it was when Molly described her adventures. “You will just be sexier, I am sure.” She blushed as she nodded.

For a couple of months her dating was pretty platonic with just a little making out. Even that helped her sort out the men she was most interested and comfortable with.

Then one night she came to my place late at night, flushed and different. She awoke me by climbing into my bed nude. Not an unusual occurrence but she was breathing differently. “I DID IT!” she announced emphatically, “I fucked my date tonight!”

“Congratulations,” I said as I hugged her naked body, “Do you want to tell me about it?”

She sure did and made me slip inside first. I had her ride so she could control the whole thing, remarking, “Doesn’t feel very slippery.”

“I made him wear a condom based on what we talked about and even though it’s a pretty safe time I won’t take chances. You were right, it doesn’t feel nearly as good.”

“Tell me about this new lover of yours.”

She smiled and began moving up and down slowly, remembering how he felt just an hour ago, “His name is Nick and he’s twenty-six, just out of the military and going to college. A pretty serious guy with a solid body and a good brain. Kind of shy but I think I prefer that. I asked him to take me to a parking spot that Molly told me about and subtly encouraged him to keep exploring. We took a blanket down by the river in the moonlight and it was very romantic, much like on the boat.”

She made a doctor’s appointment the next day to get on birth control and soon worked up to barebacking him when she found out he hadn’t dated since he left the military a few months earlier. Now I could get sloppies from her too and she felt very sexy doing two men in a row, more or less.

The new relationship seemed to be going well for a couple of months. Then I noticed some strain in Kelly when we got together. “What is bothering you, my dear?”

She reluctantly admitted that Nick had begun getting more possessive lately. “He lost a fiance while he was deployed and I think he wants me to replace her in his life. Last night he asked if I was having sex with anyone else and I admitted that I was but no details. He seemed hurt. I explained that I was not ready to get too serious with any one yet and I don’t think that set well. We didn’t have sex for a change.”

I consoled her and said to be patient. Things usually work out the way they are meant to be. She fucked me gently that night.

Two days later she was more buoyant. “Guess what?” She bubbled.

“How can I?”

“Oh, yeah,” she realized, anxious to share. “There is another student, Xi, who is here on exchange from Taiwan. I’ve been helping him with his English and he’s invited me to a party that the other people from his country are having. That will be so neat!”

After the party she was still bubbling. “Their English was bad but we communicated well anyway. There are no young women for Xi to do things with so he is happy I am willing to be his friend. We are going out on a real date this weekend.” I told her I was pleased that things were going well on that front. Nick and she weren’t doing so well, especially when she told him that she had other plans for Saturday.

Xi and she took a long hike that day and went to dinner afterwards. He had a tiny rented room and invited her there for some wine and pastries from his country. They talked and she gave him a warm kiss as she left. He seemed very awkward with that but not unhappy.

“Could we take him on the sailboat next weekend? It’s getting warm enough and Molly said she’d like to go too. How about an overnight?” I commented that it seemed to be pushing it a bit fast for this very shy and possibly innocent young man. She laughed and said she wouldn’t hurt him.

Xi was full of questions but clearly excited. This was a totally new experience for the city-bred boy. He had met Molly but not me. I stopped at his place to pick him up on our way and he sat in the front seat. The gals wanted to talk and we could get acquainted. I had to ask him to speak up over the road noise.

He was shorter than Kelly and possibly lighter too. I got some family history and that he was studying computer engineering since his father owned a tech company at home. No athletic aspirations and very focused on school. I thought that Kelly and I might give him some other interests!

He loved the sailing, having done a crash course on the internet after getting the invitation. All theory of course, but he was quite adept at applying it to the hands-on part of sailing. We hit it off quite well.

In the evening after sunset we always liked to get throws and snuggle in the cockpit to watch the stars come out and sip on something tasty. Kelly fussed over him and he was both embarrassed and pleased. He saw how Molly and I were close so he figured that was the custom.

At bedtime he was a bit confused since Kelly had given him no warning that there were only two berths on the boat. Molly and I stripped right in front of him and slid into the stern one. Kelly said his eyes were like saucers as she did likewise. He only went down to his underwear and carefully go in the far side of the v-berth. Kelly didn’t push the issue. Molly and I screwed quietly. In the morning none of us dressed and we all peed over the side. I told Xi to follow my lead and he turned away as he voided. We tried not to smile at his behavior.

When I suggested that the sun was good all over his body he whispered in my ear that his erection wouldn’t go away so he didn’t want to offend the women. I laughed, “These women would be offended if you did NOT get erect looking at their naked bodies. It is a great compliment.”

“But why you not hard?”

“Because Molly had sex with me last night and this morning.”

“Are you married to her?”

“No, we are very good friends. Kelly would have sex with you when you are very good friends too.”

His logical mind was at work, “But you and Kelly are very good friends I think. So you must be having sex with her too?” I nodded and he went into deep thought. Then he took off his shorts and a small uncircumcised erection got sunlight for maybe the very first time ever.

Molly saw him first and came over to give a naked hug. His pecker got a bit bigger I think, feeling her abundant charms. He smiled at that. Then Kelly did likewise, giving him a little kiss to boot.

We lounged and swam the rest of the day away. Molly and I went below for a sex-nap and Xi had an envious look on his face when we emerged into the cockpit again. I mentioned that to Kelly who said she’d make a move on him tonight.

When we retired Xi once again was in his underwear on the opposite side of the berth. Loud enough for us to hear in the stern booth, Kelly addressed him, “You must not know that it is rude to be clothed when in a bed with a naked woman.”

The shy young man was so flustered we could hear it in his voice, “Oh, I am so sorry. Please forgive me. I have never been in this way before.”

Kelly softened her voice, “Just follow my directions and you will do fine. Now move closer...”

We were able to follow the action by her words, a bit of watching in the dim light, the rocking of the boat, and the sounds each made. Finally, Xi was snoring and Kelly came to our berth. We made room for her. She whispered to me, “My first virgin! And my first uncut one too. It got me fired up but not finished. Please polish me off.” I fucked her to a quiet orgasm and she returned to the v-berth while I finished myself up with Molly who was very clingy with all that had transpired.

Just before dawn we heard more from the bow and saw them screwing again. There isn’t enough headroom for full cowgirl in those berths but Kelly was on top this time. At breakfast Xi wasn’t sporting an erection and when I mentioned that it sounded like he had a good time he smiled and looked away.

During our sail back to the marina Xi whispered in Kelly’s ear and she grinned at me as he took her below for a while, returning dressed. Molly and I did the same.

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Story tagged with:
Mult / Teenagers / Romantic / Fiction / Polygamy/Polyamory /