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!”

.... There is more of this story ...

The source of this story is Storiesonline

For the rest of this story you need to be logged in: Log In or Register for a Free account

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