Rough Waters - Cover

Rough Waters

Copyright© 2025 by soopad00pa

Chapter 10

BDSM Sex Story: Chapter 10 - Jack introduces his much younger girlfriend to BDSM and then her little sister joins them on a boat trip.

Caution: This BDSM Sex Story contains strong sexual content, including Ma/Fa   Ma/ft   Fa/ft   Mult   Consensual   NonConsensual   Incest   BDSM   Rough   Group Sex   Anal Sex   Sex Toys   Squirting  

The wind was up and it was raining. Not hard, not cold, but steady. We hauled up anchor after a leisurely breakfast, deciding on a whim to take advantage of the wind to head to Key West. From there, the girls would have to take a bus back because there was no way in hell we’d make it back in time on the boat.

The sailing was downwind and I poled out the jib and we were wing on wing - one sail on each side of the boat - and hauling ass. Well, for a sailboat. We were making seven and a half, eight knots and the sea state wasn’t bad. We were out in the actual ocean and the waves were maybe six to eight feet, but they were spaced out at a comfortable distance and that’s what determined comfort. These were coming nice and slow so the boat was surfing up and down in an easy motion. It wasn’t always like that. If it weren’t for the rain, it’d be a fabulous day of sailing.

“If it wasn’t for the rain, it’d be pretty perfect,” said Beth. I frowned - get out of my head!

“I like it,” said Anna. “It’s like an old lady roller coaster and the rain is just the right temp.” Beth stuck her tongue out at her sister.

“Well, if the weather holds we’ll be there in about six hours. Assuming we can find a spot - it can get pretty crowded down here.”

“Does that mean we hafta wear clothes?” pouted Beth.

“Definitely not.” She leaned forward and kissed me on the cheek.

“How about rope?” asked Anna.

I smiled at her. “Let’s see where we end up. If we’re not surrounded by little kids, I don’t care.”

Anna cooked up some fancy hotdogs for lunch and the rain died just after that. Suns out, buns out - Beth was the first to shuck her damp clothes.

We played cards - some family version of rummy with rules that were constantly changing to make sure I lost. I have a competitive streak, but I didn’t really care about cards when I could just shove my cock in whatever hole I wanted whenever I wanted. Lull them into a false sense of security...

Right in the middle of a hand Anna squealed and jumped up, pointing. There was a pod of dolphins surrounding the boat; at least a dozen of them. The girls grabbed their phones and scrambled for the bow. I double checked the autopilot and the sails and followed them, cards scattered and forgotten.

Aside from the few we saw in the creek in the dark, these were the first dolphins of the trip.

The girls were laying on the deck hanging out over the water trying to get some good video and laughing and yammering excitedly. Dolphins are always fun to see and these were putting on a show, dancing under the bow as we sliced through the waves. They jumped and dove and crisscrossed back and forth for at least fifteen minutes and the girls stayed the whole time, chattering non stop to the swimmers.

Eventually the dolphins took off and the girls came back to the cockpit.

“Dude!” said Anna, “that was like, the coolest thing I’ve ever seen. Ever!”

“They’re so cute!” said Beth. “I thought I was gonna get to touch one, they were sooo close!”

I laughed and pointed and the girls looked down. Their entire nude bodies were imprinted with the lines from the teak planking that covered the deck.

About an hour later we dropped the sails and turned on the engine. The girls had put their suits back on and Beth was steering us into Boca Chica channel. They wanted to anchor the boat themselves, so I sat back to relax (and spring into action if they screwed up). Anna headed up to the bow as we approached our anchorage and they found us a spot not too far from the bridge and not too crowded and the process of dropping the hook went smoothly. I didn’t even get up.

The wind was still blowing pretty good, but we were well sheltered by the islands and the water was pretty flat and comfortable. We had a big, shiny trawler about 100 meters off to our port but their dinghy was gone; probably in town.

“Nice work, ladies,” I said. “We might have a bit of privacy after all.”

“Thanks, daddy,” purred Beth, leaning into me. I gripped her hair and gave her a kiss and out of the blue, my lust reared up. My cock swelled rapidly with need and I twisted Beth around and bent her forward, pulling her bikini aside and pressing my cock into her with a bit of unfocused anger.

She was moist but not sopping and getting in was an effort and uncomfortable for us both. She grunted in pain but pushed back against me, sensing my need. It only took a stroke or two to wring out enough juice to travel freely and I pounded her cunt hard.

Anna sat across from us, bemused.

Beth clung to the grab bar with one hand and braced on the bench where her sister sat with the other as I battered her small body. “Oh god, daddy! I’m your little fuck hole! Take it, daddy! Yes, fuuuuucking fuuuck!”

Anna reached up and knotted her fingers in Beth’s hair with one hand and pinched a nipple with the other. I gripped Beth’s hips and sped up, getting closer.

“Are you gonna cum, you slut?” Anna hissed close in her sister’s ear. Beth nodded. “A few strokes in your dirty little cumdump and you’re ready to pop? You’re such a fucking whore!”

Anna yanked Beth’s lips to hers and Beth wailed into her sister’s insistent mouth and began shuddering with her orgasm. That was all I could take and my already imminent release was released. I grunted hard and punctuated it with a couple more slams of my pelvis.

Rage extinguished, I collapsed back to the bench behind me, slimy cock pointed to the sky. Beth sighed and sagged, relaxed.

“Fuck you, you’re not done, slut,” growled Anna. She leaned back and spread her legs, dragging Beth to her crotch by her hair. Beth dropped to her knees and eagerly dove into her little sister’s cunt, greedily lapping at Anna’s lips.

I saw Anna’s fist twist hard in Beth’s curls as she ground her pelvis into Beth’s face. “Eat my fuckin cunt, you whore. Get your greedy little tongue in my hole, bitch!”

Beth reached a hand back to rub herself and Anna leaned forward and smacked Beth’s ass hard, making her yelp. “Me, bitch! Pay attention to me - you got yours!”

Beth groaned desperately into Anna’s cunt as she swiveled her face back and forth making squelching sounds.

“Yes! Do that! Fucking fuuuuck - harder don’t fuckn stop ooooohhh fuuuuuck!” Anna gripped Beth’s hair in both hands and bucked her hips against her sister’s face. Beth gripped under Anna’s legs, hooking her pelvis and hugging her to her mouth. A few more seconds of this and Anna’s back arched and she wailed in ecstasy as her sister sucked out a bit of her life force.

As if her strings were cut, Anna slumped back onto the bench, relaxed. Beth went from desperate grinding to gentle nuzzling and cooing.

These girls were something special. I loved my life.


We weren’t technically at Key West but at Stock Island, the next key east. It was the ‘ghetto’ bit, with campgrounds and trailer parks, though a trailer park in one of the most expensive zipcodes in the US is a different animal. We tied up the dinghy at a dock run by a large RV park and paid a few bucks at the office on our way out.

It was getting late, the sun creeping toward the sea, so we just moseyed through narrow streets flanked by some of the nicest doublewides you’ve ever seen. Well manicured postage stamp yards, fresh paint, homey knickknacks adorning small porches, they were crammed in just feet from each other, just enough to walk between. A few blocks took us past what used to be an old marina - now acquired by a large national chain and renovated to a shiny corporate thing with much higher slip fees. We passed it by and reached our destination in short order.

The Docks Rawbar was a place I knew from experience would have good food. It was a small, modern renovation of what was likely an old storage facility for a long gone marine business. Rollup doors faced the water and let in the breeze. Tall, open ceilings with fans hanging everywhere and plenty of old boat and fish decor made it look seasoned but not too trendy.

The service was passable. Our waitress was an attractive bottle blond not quite my age in short shorts and a bikini top. She was friendly but a bit harried even though it wasn’t crowded. The food made up for it - a cut above good, if not great. The fish was fresh and the menu was that twist on old favorites style.

The girls surfed on their phones looking for things to do in town tomorrow - we only had a couple days left before they had to return to reality and they wanted to see all the things. Beth had been to Key West once before but mostly just barhopped; Anna had never been and none of us were much for a bar crawl. Well, I wasn’t and so they weren’t.

“Ooooh, there’s a butterfly zoo!” said Anna, showing Beth her phone.

“That sounds cool!” said Beth. “Also a tropical botanical garden and a lighthouse they let you up in - the view looks pretty sweet.”

We sketched out some plans and left plenty of room to just wing it. We left just before sunset and walked down Front Street, Shallow flats on one side and warehouses and tanks on the other until we got to the point, right on the gulf.

The sun was out of sight behind the bulk of the island but the sky was a deep orange with wisps of clouds adding contrast.

“Havana is a days sail that way,” I pointed due south.

“Oooh, that’s cool, daddy,” Beth leaned into my shoulder. “Can we go there?”

“Maybe someday. It’s a little tricky since our government doesn’t like theirs.” She booboo lipped up at me and I leaned down and bit it, making her squeal and do a little dance. I gathered Anna up under my other arm and we all stood out on the edge of the land watching orange turn to purple.

We walked back and stopped by a small grocery store for some ice cream before heading back to the boat. Our neighbors in the nearby trawler were back; they were a couple of grey hairs on their back deck sipping away and we all waved and shouted hellos as we puttered by. Boaters tend to be friendly folk, sometimes to the point of being annoying, but they were also very helpful. There’s a kind of shared recognition that any of us could have trouble at any time - engine trouble, bad weather, whatever - and so we all tended to help each other out knowing that it might be us needing a hand tomorrow.

I ducked below and brought up spoons and a couple of bowls and we just filled them up, dividing the bucket in three. It was a fancy boutique brand of Lemon Blueberry Crumble. I don’t know what they crumbled but it was a sweet and tangy combo. We all sat so that each of us was touching another, our legs tangled in a gordian knot.

I finished my ice cream quickly. I always ate fast, probably a habit formed in the military.

“What was all that ‘eat my hole, bitch’ about earlier?” I asked Anna.

Beth grinned and Anna hid her face in her hands, her spoon smearing a bit of ice cream on her forehead.

“Oh my goood, shut up!” she cried. “I dunno like, it just came oooouuut!”

“It was hot,” cooed Beth. “I think I like it when you’re bossy. Is that weird?” she asked me. “I feel like it’s weird.”

“I don’t wanna talk about it,” said Anna.

I leaned in and licked the ice cream off her face. “It’s ok to be you, whatever that might be,” I cupped her cheek and gave her a light kiss on the lips. “It was hot, lil bit.”

“I know,” Anna whispered.

“I mean, if you get bossy with me, I’ll probably beat you up and fuck the bejesus outta you,” I chuckled, “but you can boss your big sister around whenever you want. She loves to be pushed around.”

Beth smacked me. “I do not!” she exclaimed. “No, ok, I really do. I’m getting wet just thinking about what you might make me do. I never really know and sometimes that’s scary and that like, makes me even wetter. Oh god, I’m stuck in a loop and my cunt is on fire!” She reached into her shorts and brought out a couple of slimy fingers. She offered me one which I sucked clean and then pushed the other to Anna. Anna leaned forward and grabbed Beth’s wrist and dragged the shiny finger to her face, pulling Beth across the cockpit and practically into her lap. She licked up and down the finger deliberately, making hard eye contact with her sister.

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