Rough Waters - Cover

Rough Waters

Copyright© 2025 by soopad00pa

Chapter 11

BDSM Sex Story: Chapter 11 - 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  

Running around Key West was annoying, but for whatever reason, I sucked it up. It wasn’t all bad - there were some good moments, for sure - but I have trouble following someone else’s lead and the girls were definitely in charge of the day’s itinerary.

The day started with a bang. I woke up with Beth’s mouth around my cock - odd, since she’s usually very slow to wake in the morning.

“Hey, baby,” I said, stroking her hair.

“Mmrnin, ‘aby,” she mumbled around my cock.

“Why you up so early?” I asked.

“She had a bad dream,” said Anna, still curled up in my armpit. “So she went to her happy place.”

Beth crawled up toward me, slipping me inside of her.

“It was awful.” She started rolling her hips. “I was shopping and my card kept getting declined and they wouldn’t take cash and then, mmmmm, then like, my cash turned out to be fake and I got arrested by these dudes that weren’t like, real, ooooh!, uh, cops.” Anna’s hand was wiggling down there somewhere - I couldn’t tell if she was playing with herself or her sister. Maybe both.

“Then they locked me in a room and like, turned on super loud white noise. Ohmigooosh.” She rocked faster and stopped talking and started panting and moaning. I gripped her hips, digging into her flesh hard, and ground her against me faster, lifting my hips to stuff myself deeper into her. After a few more gyrations she cried out, cumming, and then dropped to my chest.

“Anyway,” she whispered, breathy. “It sucked and worse, it woke me up. I hate waking up.”

“And I hate being on the bottom,” I said and gave her a little hip bump and rolled us over. I gripped behind her neck and lifted her up and pivoted us so that Bath now lay across her sister’s legs - they could figure the rest out themselves - and I started stroking into her. No fast and furious this morning, I didn’t want a workout five minutes after waking. Just good old fashioned sex.

Beth twisted a bit and Anna opened her thighs so her sister could work. Beth went down on Anna while I fucked her. It didn’t take too long for us to all find satisfaction and we finished waking up by jumping in the water.

I took a quick look around and our neighbors weren’t up top, so we all hopped in in the altogether.

“I feel so naughty,” laughed Anna, treading water off the stern.

“You are, you slut!” said her sister, splashing her.

“Don’t wake up our neighbors - if they see you guys they might have a heart attack.”

“What about you, Mr Swinging Dick?” said Beth.

“No one cares about a crusty old dudes saggy balls,” I said. The girls laughed and attacked me, trying to dunk me. I let them push me down, but then I grabbed a leg and yanked Anna under and used the pull to bring me back up so I could dunk Beth in turn.

As it turned out, our neighbors were awake after all and the old fella came out on his back deck and saluted us with a coffee mug. “Mornin’ neighbors,” he called.

I waved back and shouted ‘mornin’ back. The girls were blushing and laughing and tried to hide behind me even though they were hidden in the water, but they waved too.

“Whaddo we do?” asked Anna, sounding nervous and shy.

“Get back on the boat - we’ve got shit to do,” I said with a shrug. We were 100 meters away - while they might be able to tell we were nude, they wouldn’t see anything useful.

Beth went first and climbed into the cockpit without hesitation and stood there proudly, rinsing off, making sure to face the trawler. She really will do just about anything if she thinks I’ll approve. When she was done, she waved at the grey-hair. Once Beth cleared the swimstep, Anna climbed up and rinsed off as well, though without the exhibitionism. She didn’t wave and sat down to dry off.

Finally, I climbed aboard and rinsed the salt off. I’m no exhibitionist, but I couldn’t care less if someone sees my junk.

Both of our neighbors were outside, now sitting on the back deck and having breakfast as the sun started climbing out of the water.

After a quick breakfast of our own, simple bagel sandwiches and coffee, we dressed for civilization and piled into the dink. Our neighbors were still out so I took us over to their boat just to needle the girls a bit.

“Morning,” I said. “I’m Jack. Beth and Anna.” I pointed as I spoke.

“Phil,” said the man - hair thinning, tan as a boot, and a little paunchy with skinny legs.

“Marjorie,” said the woman. She was in a navy one piece and looked pretty good for being on the downhill side of sixty. Also brown as a nut. “You guys just got in last night?”

“Yeah, creeping down from Miami,” I said. “We’re headed into town - any must sees?”

“If you like Cuban sandwiches, Ana’s Grocery on the south side is pretty great - they have a spicy one that’s,” Marjorie kissed her fingers with a mwah.

“And there’s a butterfly garden that was surprisingly good,” said Phil.

“That’s on our list!” Anna said with a triumphant grin.

“Can we pick you guys up anything?” I asked. I was pretty sure they’d say no - their runabout was clearly functional - but that’s just what boat people did.

“Ahhh, naw,” drawled Phil, “but thanks for the offer. We’re gonna head in for lunch in a bit.”

“If we’re about when you guys get back, stop by for dinner - we have too much snapper to eat ourselves and I make a mean fish taco,” said Marjorie, smiling at the girls.

“That sounds amazing,” gushed Beth. “I love fish tacos!” Anna kicked her in the shin.

“Sounds like a plan,” I said. “Hopefully things line up.” I hoped things didn’t line up.

We said our goodbyes and there was a lot of waving as we took off. I took us around the north side of the island and around the little island with the navy base and pulled into a small marina a lot closer to the city center. This place charged $20 for us to tie up, but we were going to pay one way or the other - Uber or a marina was getting my money.

The first stop was only about a fifteen minute walk from our parking spot and it was still pretty cool, so we hoofed it. We walked on a side street rather than the main drag, just to avoid the traffic.

“Do you really wanna eat dinner with those guys?” asked Beth.

“Eh, not really,” I said. “But it’s kinda boat-life etiquette. People help each other out and there’s a lot of socializing. Most boats are sold by their ability to entertain as many guests as possible. Not my jam, but it also doesn’t hurt to know people. Never know when you might need a tool or a part or a tow.” I shrugged.

“That makes some sense,” said Anna. “Cuz you don’t strike me as the social butterfly type. Not that I think you’re like, a dick or anything, but just ... curmudgeonly.”

“He is that,” Beth took my hand and swung it up and down.

“I am,” I agreed. “But I’m also aware of my place in the world. And yours. I know you guys aren’t anti-social and what better way to make myself look more appealing than to hang out with some old farts.”

“Older farts, you mean,” grinned Anna. I pinched her ass hard and she jumped away squealing.

The Basilica of St Mary was a modern church that looked like it’d be more at home in a suburb but it had an old grotto in a garden that, I must admit, was kind of cool. It wasn’t a big place and we were in and out pretty quickly. I learned that Beth is a fan of old gothic architecture and that she’d toured a lot of churches when she did a semester in France.

“I’m actually a bit disappointed,” she said as we left. “It looked cool on Google, but it’s pretty puny in real life.”

“Well, you’ve been to like, Notre Dame and shit, so - duh,” said Anna.

“Butterflies and then lunch?” I asked. They agreed and I pinged an uber.

The butterfly place was cool, not just kind of cool. It wasn’t huge, but it was big enough. There were exotic birds - some kind of parrots or whatever - flamingos, and a buttload of all different kinds of butterflies. They had some educational stuff - posters, videos, exhibits, and displays - but the meat and potatoes was a large greenhouse full of critters.

The girls took more videos here than they had at any other point on the trip. And I get it - there was a lot to see. Even I took a couple of pics.

“Omigosh! This one is sooo pretty,” squealed Anna. “And it’s siiiiitting on me!” There was a brilliant blue butterfly perched on the back of her hand. She brought it right up to her face and Beth stepped close to get about a thousand pics.

It wasn’t at all unusual and they sat on us off and on for an hour, the girls never tiring of it. I did, after the first few. I’m so jaded. I parked my ass on a bench and watched them enjoy themselves and at some point a flamingo came right up to me and poked me a couple of times with its weird, flat beak. I reached out and scrubbed it behind where its ears might be and it allowed that for a moment and then stepped away. The girls never noticed my Disney princess moment.

Eventually we had to leave and luckily the Cuban place Marjorie recommended was about a block away. We ordered sandwiches and sodas and walked a couple blocks to a gazebo out in the water and ate in the breeze and the shade.

Marj was right - the sandwiches were quite tasty. Beth and I both got the spicy version and Anna the regular and we all got glass bottle Mexican Cokes to drink.

“Man, that butterfly place was the coolest!” gushed Anna.

“Mmmmhmmm,” agreed Beth around a mouthful of lunch.

“I might’ve filled up my phone.”

“I’m sure you guys got some good stuff,” I said. The spicy could’ve been more spicy, but it sure was tasty. Plenty of cheese to glue it all together and the biting sugaryness of the Coke was a great complement.

“Sooo much,” said Beth. “My instagram is gonna be so lit!” She stuck her tongue out at me, knowing my opinion of social media.

“For real,” agreed Anna. “I’ve already got a shitload of likes and I only put up one story!”

I rolled my eyes in silent protest and focused on how good they looked in their short shorts and belly baring tops.

After lunch came the worst part. We headed over to the super popular shopping, bar crawling tourist strip. There was an endless parade of clothes stores, jewelry stores, shitty art galleries, and tourist bars that all had some kind of garishly colored signature drink in its own goofy container.

The afternoon passed in a haze of misery as the girls traipsed in and out of clothes shops and various knickknack joints, getting their mitts on virtually everything in Key West. I mostly sat on the sidelines, occasionally being dredged up from daydreams of killing everyone in sight to render judgement on some shirt or skirt. The girls had good taste and were lovely to look at but I’m just not a shopper. I order a few shirts and a couple pairs of shorts a year from Amazon, just to replace things I destroy doing boatwork or something.

They were enjoying themselves and I made an effort to not be too much of a buzzkill since, for the most part, they hadn’t submitted me to much at all of the ‘kids today’ bullshit.

Finally, they determined they were done. Each had a couple of small bags which I happily took - as a heterosexual man, carrying stuff is hardwired.

“Thanks, daddy,” Beth nuzzled into my ear. “We’ll make it up to you - promise!” Anna kissed me on the opposite cheek and nodded in agreement.

“I know you will,” I growled. I was aiming for playful, but some anger must’ve leaked out because Anna’s eyes widened and Beth purred, melting against me.

I took a breath and smiled. “OK - options,” I said. “We can head to the lighthouse and if it’s not too crowded, watch the sunset. We can wander and find a restaurant. We can head back and eat Marjorie’s fish tacos.” I held up fingers as I listed their choices.

The girls looked at each other and without discussion said “Fish tacos!” in stereo.

“Tacos it is,” I said, inwardly gritting my teeth.

“That way we’ll be back at the boat sooner so we can like, help you relax after your stressful day,” explained Beth.

“So much relaxing,” said Anna with a giggle.

We stopped to grab a couple of things - we of the elder generations don’t show up to people’s homes empty handed. A small boutique grocery by the marina where we parked made a one stop shop. I grabbed a bottle of Reisling and a six-pack of some hipster IPA with a pirate on the bottle and finally, a blackberry cheesecake.

Beth argued for apple pie, but I pulled her in close with a deathgrip on her ass and bit her neck until she whimpered “I like cheesecake toooo, daddy.” I let go and she stumbled a bit, breathing heavily.

“What?” I asked Anna, who was watching us. “You want some?”

“Yes,” she said, so I stepped in close to her amongst the fancy desserts and stuck my tongue down her throat until she began to panic from lack of oxygen.

A couple of shoppers took note of our shenanigans, but it was a party town so we weren’t particularly out of place. We left arm in arm, bags dangling from our conjoined elbows, as we made our way back to the dinghy.

Phil and Marjorie weren’t out when we passed but their dinghy was tied off the back, so they were likely around. Anna tied off our dinghy with an expert cleat hitch and held the inflatable steady as Beth handed up the bags.

During the boarding process, Phil stepped out on deck and waved his radio. I gave him a thumbs up and signaled ‘just a minute’ and nodded and headed back in out of the sun. We got the stuff settled and the girls started shucking their clothes.

I grabbed the radio and hailed on channel sixteen, the generic channel. “Fishy Business, Fishy Business, this is Inconnu, over.”

“Go to twenty, Inconnu,” Phil replied. I did. Anna knelt in front of me and began tugging at my shorts.

“Hey, Phil - what’s the word?” I asked. Beth was peeling my shirt off from behind.

“Dinner in about ninety minutes?” he asked. Anna ran her tongue down my belly toward my twitching shaft.

“Can do - gives us enough time for a, uh, dip.” Beth stroked her fingers down my back, scratching lightly.

“See you then! Fishy, out.” Anna took my cock in her mouth with an ‘mmmmm’ as Beth’s body pressed in close from behind, her fingers stroking my thighs and belly.

I gripped Anna’s hair and gave her throat a couple of hard thrusts, making her gag, before letting her take over again.

“I know you were miserable today, Jack,” whispered Beth, nibbling at my ear. “I really appreciate your patience.”

“Show me,” I whispered.

Beth bent forward and whispered to Anna; they both moved to the bed. Anna lay on her back and Beth straddled her face and knelt on her forearms, effectively trapping Anna’s hands.

“Daddy, do you wanna fuck my baby sister? She needs to learn who’s boss,” Beth pitched her voice to sound innocent and helpless and while my brain knew it was cheesy, my lizard lifted his head, paying attention.

I stepped forward and lifted Anna’s legs, pushing them back for Beth to hold. Anna was licking her sister’s cunt absently as they both waited.

I aimed my cock at Anna’s moist hole and slammed in without any preparation. She cried out into Beth’s cunt and her body went rigid. I slowly withdrew and bent down to softly lick the length of her from ass to clit. Her body sagged, relaxing a bit.

As I gently teased Anna’s clit with my tongue, she must’ve resumed her work on her sister because Beth began sighing and circling her hips on Anna’s face. Anna would shiver and moan and tense when I focused on her button and then sigh and relax as I took long swipes up and down with a wide, flat tongue.

I stood up and pumped into her a couple of times and then dropped back down to suckle her clit some more. This time I worked a wet finger into her ass and her moans escalated. Beth was getting louder so I stuffed my cock back into her sister and leaned over to get in Beth’s face.

“No cumming,” I said. She pouted, biting her lip, but nodded.

I took a few more strokes and then mouthed Anna’s holes again, slipping two fingers into her ass.

Anna must’ve heard me because she was really going at her sister. I imagined she wanted to get Beth in trouble - it might work. Beth was panting and gyrating hard. I let her work a bit to see who would win and then I decided it was going to be me.

Standing up, I pressed my cock into Anna’s tight little ass for only the second time ever.

“Oh fuck meeeee!” Anna squealed, muffled by Beth’s juice box. I stroked slowly but firmly into her depths. “Fuh fuh fuuuuuuh-uuucck, omigooosh. Oh Chriiist!”

Beth, having settled down a bit, gripped Anna’s nipples and twisted them hard. “You tryna make me cum, you whore!? Get me in trouble!?” More twisting and Anna was writing and squealing beneath us.

I pulled out of Anna’s ass and plunged into her cunt hard. Then back into her ass, alternating as quickly as I could switch.

Anna was grunting and panting and begging. “Oh jesus! Fuck me, omigod moooore! Oh, it huuuurrrts! Oh I’m gonna cuuum, jesus daddy!”

When Anna screamed ‘daddy’ Beth started slapping her tits hard. “He’s my daddy, bitch!”

Anna was about to explode and I froze and grabbed Beth’s hands. “Don’t move,” I said. Anna shuddered and moaned under us and then, realizing we’d stopped, began to wail and beg.

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