Dirty Naked Poker

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One couple. Two siblings. Six friends. All come together.
35.9k words
4.78
550.6k
1.2k

Part 1 of the 2 part series

Updated 06/07/2023
Created 05/03/2015
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[Hey there Literotites. First time, long time. This one turned out a little longer than intended (ha ha), but I'm happy with how it ended up. If you like masturbation, voyeurism, incest, anal, loving wives(girlfriends, really), oral, girl/girl, reluctance, or group sex, there's something here for you. If you don't like those things...well...I don't know what to tell you.

I put this in the Incest/Taboo category because, in the end, it is a story about a brother and sister.

Everyone here is over 18.

Good times.]


"That sure is a lot of condoms, Sam," I said.

I stood as far back from my friend as I could.

Sam just reached into the box for another handful and tossed it into our cartÑalready filled with Gatorade, salted nuts, and granola bars. Everything two growing boys needed for a 'promising' weekend on my parents' yacht.

"It's going down, I can feel it," Sam said.

"You have a girlfriend. How much shit is really 'going down,' man?"

Sam snorted.

"Kate's cool," he said.

I've known Kate since high school. One thing I know for certain is that she was not 'cool.'

Sam had told me stuff, too. Kate wasn't exactly...enthusiastic in bed. It had taken almost a year of dating for her to go further than a tentative hand job. And everything was with a condom. Everything.

No cumming inside her. You sheathed your dick and you did your little back and forth. Then, long before anything might happen, you pulled out. And since nothing was going in her, nothing was going on her either. Your...efforts were to be deposited into the condom. The end.

Once, Sam told me, he had accidentally spilled a bit of sperm on her stomachÑher stomach!Ñand Kate had freaked for weeks. This was not a girl who was 'cool.' This was a girl who was having sex for the same reason you curb your dog or clean the litter box. If you want the relationship, you've gotta do some ugly stuff or everything turns into a big smelly mess.

Based on everything he told me, I wasn't sure why Sam was with Kate. Actually, that's a lie. I knew exactly why he was with Kate. It was the same reason I had pined after her for all four years of high school.

Kate was H-O-T hot. Super hot. Tall, big blue eyes, long brown hair that seemed to shimmer in the sunlight, blow job lips (Not that she ever gave blow jobs, but damn, those lips looked like they were made for it. Kate's unwillingness to suck Sam off was like a dude going speed limit in his Porsche), and the pieces-de-rŽsistance: huge gravity-defying tits. Kate was real world gorgeous hot. Which meant she could get away with being a bit of an ice queen. OK, more than a bit. Kinda the queen of the ice queens?

All right, that's not completely fair. But still.

"You getting any?" Sam pointed to the shelf.

"Nahhh. No girlfriend to use em on," I said, feeling a little embarrassed by my current state of singlehood.

"Come on, Jason, you never know," Sam said, "gonna be lots of ass to choose from at this weekend."

"Well, let's see, there's your girlfriend, my sister..."

"There ya go," Sam said.

"I'm not doing my sister," I said.

"But she's bringing a friend, right?"

"Doing my sister's friend is too much like doing my sister," I said.

"Well Kate said she'd be bringing someone so..."

"Didn't you tell me all of Kate's friends were dogs?"

"You don't have to look at the girl, just..."

"No thanks. Just...no thanks," I said.

So I didn't buy condoms. Of course, Sam went ahead and bought enough to keep an entire Olympic Village going at each other for at least several weeks, so maybe I just figured I was in the clear.

Or maybe I was just lying to myself. I'm not sure, to be honest.

*

Sam and I were first to arrive at the dock. We took the little two-stroke engine motorboat across the bay, and then bivouacked our supplies onto the yacht.

It wasn't the biggest thing the world, but it slept four pretty easily and it wouldn't feel too crowded with six. There was one master bedroom, a smaller bedroom with two bunk beds, a full head (aka, bathroom), a main room with a fold out couch, a little kitchen on the far side of that, and plenty of sitting room above deck, as well.

There was no TV, no Internet, but an absolute ton of alcohol. My sister and I nicknamed the ship the "S.S. Trouble" back when Dad first bought it.

He'd gotten it on a lark, trying to create a way for the family to spend more time with each other. It had kinda worked. I mean, my sister was joining us so...

The first to text us for a lift was Kate and her friend, a girl I hadn't met before. Sam, being the boyfriend, won the right to ferry the girls back to the boat. I was organizing plates and glasses, not really paying attention, when the three of them came below deck.

There was a loud bang, like someone dropping a large amount of luggage. Kate and Sam were already bickering, Kate's friend stood off to the side, looking anxious.

"Where are we sleeping?" Kate asked.

I shrugged.

"I dunno. Wherever, I guess."

"Really Jason? We're gonna just sleep on the floor like fucking animals?" Kate shouted. Her friend seemed to step back even further.

"No."

I raised my hands in surrender.

"I just...didn't plan anything 's all. Just...I dunno, take my parents room."

Kate made a "urrgh"Ña growl of satisfaction and exasperation, then marched past the kitchen to the main cabin. Sam followed, lugging several suitcasesÑmore bellboy than boyfriend.

I looked over at Kate's friend, still cowering in the corner of the living room.

I extended my hand.

"I'm Jason."

"Ashley," she said, smiling slightly.

Ashley's golden hair fell in cute little ringlets around a not-too angular face. Her nose and ears were just a little too big. Everything else on her was tinyÑthin little lips, neat agile fingers, bit of a bum just peaking out from under her long, brown sweater. She couldn't be more than 5'1", maybe 5'2" with the right set of shoes.

Really super cute. She was like a mix of the weird artist chick in your freshman dorm and the nice girl who grew up down the street from your childhood home. She made me wish I'd bought condoms. As soon as I let go of her hand, the smile raced off her face. I gestured for her to sit, but she just stood there. Thin, quiet, standing on the side of the roomÑshe was like an attractive, fuck-able lamp.

My phone buzzed, letting me know it was time to get my sister. I told Ashley where I was going. She just nodded, nailed to the floor. If she didn't move soon, I was gonna have to try to return her to IKEA.

*

My sister Emma gave me an awkward half-kiss half-hug when I arrived. Her friend, Kristen, blonde and beautiful, started picking up boxes and helping me. Em got the hint and helped as well. We were on our way in minutes.

The girls sat at the front while I steered from the rear. They both looked angelic, sitting at the bow, their hair whipping in the wind. Kristen was tall, almost my height, farm girl looks in full display. She had thick blonde hair down to the small of her back. Freckles splashed across her nose and shoulders. She was probably a couple pounds overweightÑ10 if you believe Cosmo, but I don't. It filled her out nicely, honestlyÑit added a little extra heft to her boobs and ass. I'd known Kristen since my sister was in middle school. They were both a year younger than me, finishing off high school, getting ready for year one in college. They'd already planned on going to the same school, natch. They were inseparable. Kristen and my sister.

My sister. Yeah. The little brunette leaning back in the boat, eyes closed, soaking up the salt air. She looked even better than I remembered. Her chest a little fuller, her body a little more defined. Em played soccer since forever. She always had her brown hair tied up in a ponytail. Always dressed in a t-shirt and shorts. Guys would tease me that my little sis was more of a dude than me. They wouldn't say that looking at her now.

Yeah, I guess it's fair to say my sister was kinda my dream girl. Not my sister sister...I mean, that's just not a good idea. But a girl that looks and acts and is just like my sister. Yeah.

This just had to end well, right?

Yikes.

*

After a day of travel, no one really felt like doing much. We ate soup I warmed out of a can, we changed into pjs, we called it a night. Not a beer was cracked.

Sam and Kate had already claimed the master bedroom. Emma and Kristen agreed to squeeze into the bunk beds in the other room. That left Ashley on the fold out couch and me in a sleeping bag on the floor nearby.

I noticed Ashley was wearing pink pj pants and a little strappy pink top before she slid under the covers. I was wearing long flannel pants and nothing else. If she felt uncomfortable, she didn't say anything. But, then, I wasn't sure she'd speak if she was sleeping on needles. Quiet little lamp.

The room was almost totally dark. The ocean rolled in the distance. I sighed, contentedly. It was nice to be back on the boat. We were only a few miles off shore, but I was already too far away for my troubles to reach me.

I heard the squeaking first.

Then the hushed voices. They sounded excited, a little upset, maybe even a little angry? Then more squeaking. I couldn't help but look up at Ashley on the couch. She was wide eyed. I couldn't see where her hands were.

Then there was grunting.

Sam's voice. "Oh. Oh yeah. Oh baby. So good."

Over and over. Little grunt from Kate.

"Oh yeah. Come on..." I heard her say.

"Come on..."

I looked over at Ashley again. Her little curls were trembling. Her blanket shifted back and forth. Working herself pretty hardcore there. I reached into my own pants and took hold.

"Oh god..." Sam said.

"Come on, baby..." Kate said.

"So good..." Sam said.

"Come on, baby," Kate pleaded, "get there. Come on, baby. I know you can get there. Come on."

Ashley's squishy sounds were almost as loud as the squeaking bed now. Her breaths were coming in these short, deep little gasps. I was working myself full on, now.

"Ohhhh...almost...," Sam finally exclaimed.

"Pull out baby! Pull out pull out pull out!" Kate cried.

"Oh god, but I'm so close," Sam whined, "I've got the condom on, baby, come on, just this once why can't I..."

"No!" Kate practically shouted. In that moment, my dick dropped limp like the poor little guy had been shot. I looked up and saw Ashley shudder, arms locked at her sides, head tilted back, a little squeaky gasp escaping her mouth.

Guess not everyone is turned off by a bit of arguing.

"Baby, I..."

"Sam. No."

I heard the sound of a shove. The squick squick squick of a hand working a cock. I know the sound. I had just been making it myself.

"Ahhhhhh," I heard Sam reach his climax.

"There you go, baby. Isn't that better? You feel better, baby?" Kate asked.

"Uh huh," Sam said. I heard a click, like a light being turned on. Bright yellow spilled from under the door. I quickly readjusted myself, waiting for someone to come out. Nothing happened. The light clicked back off.

It was dark. All I could hear was the ocean and the sound of Ashley's slight snore. I was blue balled as all get out, but my cock stayed limp. For whatever reason, now that Ashley had finished, I felt a little strange tossing one off with her in the room. At a certain point, I guess I just fell asleep.

*

The next day, we swam in the ocean, ate whatever, napped, then did it all again. We also opened up the alcohol.

By the time the sun was down we were all pretty good and lubricated. No one was falling down drunk, but we had all discovered a wonderful midpoint between buzzed and blasted. Then Em pulled a joint out of...somewhere?...and we passed that around for a bit, too.

We all sat around the living room, alcohol bottles resting everywhere there was flat space. The ocean sighed. I was in a nice, comfy place.

"See, now this is when a TV would be really super nice," Kate said. Emma just glared over at Kate. My sister had never gotten along with her.

"I think this is nice," Kristen said.

"Me too," I said.

"So what's on for tonight?" Sam asked, maybe a little too anxious?

"I think we can figure something out," Emma said, smirking. She stood up. Still seated, I could almost follow her smooth, muscular legs right up the bottom of her shorts to the promised land. I wasn't the only person looking, either.

Emma practically pranced over to the kitchen. She grabbed an empty wine bottle and brought it back to the circle. Just looking at the bottle, my cock began to grow. Good times.

We'd all gone to high school together, except for Ashley. We'd all played games like this one. Spin to win and all that. It never went much beyond basic cable nudity and a bit of making out. But then, that was high school. With my parents in the next room.

Now four of us were in college and Emma and Kristen were both of age and headed to uni in the fall. And there were no parents here. And we were drunk and high and horny.

"I believe we're all familiar with our little friend here?" Emma asked,

"Except maybe Ashley?"

Ashley nodded pleasantly. My little lamp. Maybe tonight I'd figure out how to switch her on.

Emma was explaining.

"...and then you give them a dare. Anything you like. Preferably something dirty, but, y'know, whatever, really."

Kate shifted, slightly. She was sitting to my right and I felt her stiffen.

"Guys...I dunno. I mean. We've done stuff like this before, but...," Kate said, "now I'm together with Sam and I..."

"You don't have to do anything you don't want to do," Emma said, reassuringly.

"C'mon, babe," Sam said, totally not looking at Kate, "It'll be fun."

"I dunno," she repeated.

"I've got a problem, too," I said. Everyone turned to look at me, confused. I pointed at my sister, Emma.

"What?" Emma asked, "I'm 18, Jay Bird. You're going to have to accept that I'm a grown up woman with grown up woman wants and grown up woman needs."

"No no. That's not... I mean, you want to let a bunch of guys just fuck around with you I'm not gonna stop em," I said.

Then I realized what was coming out of my mouth and stopped myself. "I mean, I care."

"That's my bro!" Emma exclaimed, "so sweet and protective!"

She leaned playfully into Kristen who laughed along with her best friend.

"No! That's not... Look, I'm a little drunk here. And a little high. Just, like, cut me some slack or something, OK?"

"It's fine, bro," Emma giggled, "I'm glad you're so excited about your slutty little sis."

I moaned, exasperated.

"Look, if we're gonna spin the bottle around and do, I dunno, whatever, I'm just... I mean... Like, if it's pointing at Emma I don't want to..."

"So maybe Kate and Emma, like, just don't play," Sam said, "That way no one does anything they don't want to."

"Wait, I have to go hide in the bedroom while everyone else has fun because my brother can't handle what might happen?" Emma snapped.

"And what about you?" Kate rounded on Sam, "You'll just... sit here while I wait for you back in our room?"

Sam's hands shot up in surrender.

"No! I was... It was just... I' m trying to make everyone happy 's all."

"I have a boyfriend, too," Kristen said, quietly, "So I...ummm... I guess I won't play either...?"

The room went silent. I could feel the mood

We all came to the boat knowing we'd do something a little wild. You don't spend all day in skimpy bathing suits, drinking and getting high just to eat a nice meal, have a little chat, and then call it a night. We were in our twenties, not our forties.

Now that the moment had arrived, no one wanted to be the one to start things off. We were drunk, and bored, but we'd talked ourselves into a bit of a corner that no one really wanted to stay in. We just needed an excuse to take advantage of ourselves.

"OK," I said, "Let's change the game a little."

I stood up, taking the wine bottle with me.

"New game," I said.

I rooted around the cabinets.

"This is a deck of cards," I announced, holding up the deck as I walked back to our little circle.

"Wow," Sam said, "you really are full of amazing tricks."

"Ha ha. Now, I'll shuffle the deck and deal each of you a card, face down. High card wins. But before we reveal our cards, each of us can make a bet. Something silly, something dirty, whatever."

"So like, I get a Jack and I say I'll...I dunno...take off my sock if my card isn't the highest?" Emma asked.

"Exactly. If I show a King or whatever, you have to take off your sock. I mean, hopefully it'll be something a little more fun than that. But you get the idea."

"What if I don't like my card?" Kristen asked, "What if I've got a two or something? Do I have to bet?"

"That's the beauty of the game," I said, "if you don't like your card, you can just fold. No harm done. And since you're picking your own bet, you're never doing something you're uncomfortable with."

"What about the winner?" Sam asked, "What does he get?"

"He or she," I said, "is the recipient of the bet. So like, if Ashley bets a kiss and she loses to Kristen, Ash has to kiss her."

Kristen looked a little abashed at my example. Ashley, on the other hand, seemed strangely pleased by the idea.

"Kiss what? Where?" Sam asked.

"Well, maybe Ashley specifies. Or it can be winner's choice. I dunno. It's just a way to get things going, guys. It's our game, we can always adjust as we go."

"Sounds good to me," Emma said.

"Me too," Kristen said.

Ashley just nodded and smiled. At this point, not wanting to be the downer, Kate seemed to agree, as well. I didn't even bother to check with Sam.

"OK then. Everybody get a drink while I shuffle up and deal," I said.

*

I dealt clockwise, as if we were playing poker and not "weird dirty kinda sexy game I just made up." I was still workshopping the name, obviously.

The deal went Emma, Sam, Ashley, Kristen, Kate, then me. Looking back, people were sitting in a way that said a lot about what they wanted that night. At the time I was oblivious. I just assumed that everyone sat wherever.

I was so so so so wrong.

I looked down at what I had dealt myself. Ten. Not bad. Not a big winner, but not terrible either. Again, just like poker, we bet around in the order of the deal.

"I'll bet a sock, I guess," Emma said.

"We're doing clothes first?" Sam asked.

I couldn't tell if he was happy about that or not. No one answered his question.

"OK, I'll call your sock," Sam said.

Ashley folded. So did Kristen and Kate. I looked at my ten.

"Oh what the hell."

It was just a sock, after all.

Emma showed a Jack. Sam had the Ace. I didn't even bother taking out my tiny ten.

"Ha ha!" Sam cried triumphantly.

Emma threw her sock at him. I did the same.

"What am I supposed to do with these?" Sam asked.

"I dunno," I said, "but you won them."

"Yay for me?" Sam said, "I mean, ummm, yay for me!"

"That's the spirit," Emma told him.

Sam looked over at Kate as if to say, "See, not so bad?"

Kate smiled back, wanly.

The rest of the round was sock city. I didn't see anything higher than an eight. To pass the time, I played a little game with myselfÑgiving each of the girls a little award.

Kate was clearly most beautiful overall. Best hair went to Kristen's extra super long blonde hair, no question. Although I could kinda see Ashley's tight blonde curls as a dark horse. I liked watching them sproing every time she moved her head.

Best boobs went to Kate with Kristen a close second. Best eyes: Emma. Best mouth: Kate again. Best hands: Ashley. They were so quick and thin; I couldn't help but fantasize about her wrapping them around my cock.