Never Have I Ever

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Old high school friends go out on a boat and play a game.
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[MMMFF, anal, double penetration, rimming, boat]

"Hey Casey -- pass me another beer, will ya?"


Casey reached down to open the cooler, almost falling over when the boat rocked in the wake of a passing party boat.

"Here you go Dave -- one ice cold brewsky," said Casey, stretching to pass it to him over Melody's perfectly tan bikini body. A bead of ice cold sweat dripped onto the warm, smooth skin of her leg, making her yelp and shiver.

"Thanks," said Dave, popping the cap on the bottle opener built into the boat.

"Case, pass me one two? I'm parched," said Josh, across from her. She handed him one and grabbed herself a hard lemonade. Why not?

"Hey Dave," called Rob from his perch at the driver's seat. "Do you mind if we explore one of these coves? I'm getting tired of being rocked by these big boats. Hardly anyone visits the coves here, so we could have our own private party, undisturbed."

"Yeah, sure. Okay with you, Mel?"

Dave and Mel were the owners of the boat, but this was Mel's party, so he let her make all the decisions.

"Yeah, sounds cool," said Mel, sitting up from her makeshift tanning bed. "I'd love some privacy. And then we could go swimming, too."

"Great!" said Rob. "Get your lifejackets on then, and I'll show you my favorite cove on the lake. Very private, and not accessible by those big party boats."

As everyone shrugged on their bulky lifejackets, Rob kicked the speed boat into gear. "Hang on!" Then the boat lurched into motion, gaining speed.

"The place I have in mind is all the way at the other end of the lake -- but I promise you won't be disappointed!" he shouted over the roar of the engine.

As they bumped over the wakes of other boats, wind in their faces, Casey sipped her Mike's Lemonade.

She never imagined that she'd find herself on a boat anytime soon. Much less an old friend's boat.

She knew Dave, Mel, Rob and Josh from high school (though Dave and Mel had been "frenemies" back then). While she'd remained "friends" with them on Facebook, there hadn't been much actual friendship in the last 10 years, aside from sharing funny memes and some light stalking of each other's adult lives.

Two years ago, Mel and Dave had finally tied the knot after years of not-so-subtle flirting and off-and-on dating. It had taken them a while to settle down, but now they had the American dream: a house, a dog, and, just this year, their own boat. Casey was sure the two and a half kids would be on their way soon.

Josh, on the other hand, was still struggling to land himself a decent job, much less a girlfriend -- or was it boyfriend? -- Casey wasn't sure. Either way, he spent most of his days playing video games online, which showed in his pale skin.

And Rob was not much different from the fun-loving playboy he'd been in school, with a different girl on his arm each month.

Casey had seen the pictures of Mel and Dave's new boat a couple months back -- the perfect smiling couple, with perfect smiling friends, having a blast drinking beers and fishing on the lake. She couldn't lie -- she'd been more than a bit envious. She didn't have enough real friends to have a party. And certainly not on a boat.

So she was very surprised when she'd gotten an invitation from Mel to go out on the boat. She said she wanted to reconnect with her high school friends -- a reunion of sorts.

Curious -- but mostly thinking about the pictures of smiling friends -- Casey had accepted.

So here she was, awkwardly hanging onto the rail, feeling very out of place. She hoped that things would go well and she'd have more friends -- but downed the rest of her Mike's for some liquid courage.

The boat slowed as Rob steered into a cove that wasn't even visible from the main lake. If you didn't know it was there, you probably wouldn't find it. And it was definitely too shallow for the party boats.

Rob carefully threaded the narrow straight, curving around the bend -- and suddenly, it opened up again into a luxurious cove, complete with a deep pool for swimming, and a rock wall for diving.

Nobody would disturb us here.

Excited, everyone immediately started tearing off their life jackets. The guys took off their shirts to soak in the sun. Mel had already returned to her tanning bench and was sprawled in the UV rays.

"Great choice Rob! This spot looks amazing," said Josh. He was the only one who kept his shirt on.

"Yeah, a friend showed it to me last year when we rented some jet skis -- definitely a local secret. Don't tell!"

Rob parked the boat in the middle of the pool. Then they all raided the cooler for more drinks. Even Mel got up from her sunning to grab a drink.

"So guys," she said, "thanks so much for coming out on my little reunion. I see your faces all the time on the Facebooks and I just thought -- why not catch up? It's been entirely too long. I feel like memes don't really count."

"Definitely," said Rob. "Plus, you know -- I get to drive your sweet-ass boat!"

Dave laughed. "Glad we could make your nautical dreams come true Rob."

"Yeah, I feel like it's been an age since we played Never-Have-I-Ever at Rob's high school graduation party," said Mel. "Oh hey! Guys! I have an idea -- why don't we play it, here and now? See how much we've changed, break the ice. What do you say?"

"Um..." Casey mumbled. She had never been much of a fan of Never-Have-I-Ever. It looked like Josh agreed, but he didn't say anything.

Before she could suggest something safer -- swimming, perhaps? -- Rob belted out "HELL YEAH! Let's do it."

"Awesome -- but there's a catch! We're gonna play the drunk version. Get this party started! You have to take a drink every time you put a finger down. Okay?"

"Yeah, sure," said Josh, still trying to fit in with the "in" crowd.

Mel passed out more drinks, and the game began.

It was just as awkward as Casey remembered. Everyone struggling to think up the most embarrassing acts they knew, while everyone else laughed and pretended it was cool that their closest friends were divulging their deepest, darkest secrets to the public.

Dave started. Sure enough, he held nothing back.

"Never Have I Ever... gagged while deepthroating a banana!"

He belly laughed as Mel put down a finger, smacking him with her other hand. "Not fair, you know too much about me!" she said, laughing. She took a deep swig of her drink.

"Well, you know everything about me too, so... I guess Casey, Rob and Josh can duke it out while we get shitfaced!"

Rob was next.

"Never Have I Ever... given a dude a blowjob."

Casey and Mel both rolled their eyes and took a drink. But to their surprise, Josh hesitantly took a drink too.

I guess that answers THAT question, Casey thought.

Everyone was staring at him. Flushed a deep red, Josh mumbled, "Um... I'm not gay or anything. Well, I guess you'd say I'm... bi? Bi-curious?" More silence. "I like girls, mostly, but I'm open-minded."

"Wow," said Mel, breaking the silence. "Good for you Joshie! I'm impressed."

The guys quickly chimed in, "Yeah, man, totally support you." "Totally cool."

"So..." Mel drawled on. "Who was the lucky fella? Anyone I know?" Of COURSE she'd want the juicy details. Always one for the gossip, Mel.

"Um... it was really just a one-off thing. But it was nice, I guess. Like I said, I really prefer girls -- so no worries guys -- but I had an opportunity to try it once, so I did."

Before Mel could dig deeper, Josh quickly added "Okay, my turn yeah?" Mel pouted, but waved him to continue.

"Uh... Never Have I Ever... done anal sex."

"Giving or receiving?" asked Rob.

"Uh... Either?" said Josh.

Rob took a drink and Dave gave him a fist-bump. "Blue-hair girl from college?" he asked.

"Yeah man," said Rob. "That girl was FREAKY. Love it."

Casey sighed. She knew she was going to regret this, but her honest side wouldn't let it lie.

She took a deep drink, finishing off her Mike's for good measure. If she was going to deal with this, it may as well be with a nice buzz, she thought.

She put down a finger, sealing her fate.

"WHATTT!!!" Mel exclaimed. "Shy Casey, doing anal? Who would've thought?!? I need details please. With who, when, where, what was it like, did it hurt, did you like it...?" Mel rambled on excitedly. Oh boy.

"Well... I guess I have a bit of a confession to make. But please don't go nuts on me Mel, okay?"

Mel, wanting details, pretended to zip her lips and toss the key. "I promise."

"I'm... um... I've actually always been into anal. It's kind of a fetish. I never really liked it the 'regular' way."

Mel looked like she was about to explode with excitement. Her eyes were popping and she was sitting as close to the edge of the seat as she could without falling off. But true to her word, she stayed silent... for now.

"I started just with myself -- there wasn't a guy or anything, which is probably best because it's much easier to get started on your own, rather than having a guy ram at you.

"When I started dating, I tried regular sex, but it was honestly just boring. And I had a hard time... you know... getting off... without it.

"So I started looking for people who like anal only, and that's how things have been since college, basically."

Casey looked bashfully at the floor of the boat, waiting for the freakout. But surprisingly, it never came.

She looked up to find curious eyes looking at her.

"Wait, so... you ONLY have anal sex? No vaginal sex?" asked a quizzical Dave.

"Nope -- not if I can help it. It really just is boring to me."


Then he suddenly burst out: "... see babe, CASEY likes anal, why won't you just give it a try? It can't be THAT bad."

"DAVID!!! That was private." Now Mel was the one blushing.

"What, Casey just poured out her deepest secret in a stupid game of Never-Have-I-Ever, but you're not willing to admit even the possibility of anal?" said Dave.

Finally - the tables have turned, Casey thought.

"It's so embarrassing though!" exclaimed Mel. "Don't you think it is embarrassing, Casey? I mean... that's where POOP happens. And yes, ladies do poop," Mel added, looking at the guys.

"Well, I guess it was embarrassing at first... Even in private, I thought, this is so wrong. But it also just felt so good, and it wasn't hurting anybody, so... why not?"

"But... doesn't it hurt? Isn't it gross?" Mel asked, now unsure.

"It can hurt if you do it the wrong way. You have to prepare for it, use lube and go slow. But once you're prepped, it feels AMAZING. And as far as gross goes... well, you can prep for that too, get clean. But it's not usually a problem. And if it happens, well... you just clean it up and carry on."

"Oh. I guess I never thought about it so much before. You really like it?" she asked, shyly.

"Yeah, it feels SOOO good. Nothing makes me cum harder. I especially love being stretched. But you still need clitoral stimulation, usually."

Suddenly Casey remembered that there were three horny guys on the boat with them, hanging on her every word. She'd forgotten in her passion to answer Mel's surprisingly genuine questions.

"Uh... but yeah, it feels good, when you do it right. The best."

Mel sat thoughtfully. The guys, she thought, looked like they were still in shock that girls were discussing anal in front of them. Josh was crossing his legs in an odd sort of way, turned away from them.

Rob, having done anal once before, was the only one who didn't seem completely lost by this conversation.

"Yeah man, anal rocks!" He lifted his bottle in cheers, surprising her -- she never thought Rob would be the one she'd bond with.

Dave, seeing an opportunity that might work in his favor, asked: "Hey Case, if you don't mind... could you share some pointers? Like... what advice would you give to someone who had never done anal before?"

"Um, sure I guess? Well, first thing I'd recommend is that you practice on yourself first. It's a lot easier to control things while you get used to the feeling.

"Start small -- a finger usually works best -- use a lot of lube and go very slowly. Like, take your time. Rub it. Enjoy it. Start to get a little turned on. Let yourself loosen up.

"Then slowly insert the finger, taking it a bit at a time. It'll be kind of weird at first, but in a good way. Keep working with just the one finger until you are comfortable, then you can go faster, enjoy it more. Maybe get off. Do that until it gets easy.

"Then, when you're ready, slowly add another finger. Feel the stretch. You kind of have to train your asshole to stretch further each time. It might take a while to get up to a certain size. But it is worth it. It feels so good. Remember to keep applying lube, if needed. Lube is very important. And don't push yourself too far, too fast.

"THEN -- once you are comfortable with two or three fingers -- THEN and ONLY THEN should you consider having a guy try his dick. If you can't warm yourself up, then make him do it -- have him start with a tongue, a finger, and move up. It should be his job to get you ready and check that there's enough lube."

Silence. Then --

"OH MY GOD!" Mel shouted in disbelief. "Is that a boner, Josh?"

Poor Josh had abandoned his attempt to cross his legs, going for a life-vest to cover his erection instead, but alas -- Mel had chosen the exact wrong time to look over and discovered a very large bulge in her face.

Josh immediately put his hands over it like a kid in grade school, then tripped over the life vest he had dropped. Hilariously, he landed with his face in Mel's lap, right between her legs.

Josh took one whiff of her sex and his boner surged anew, visibly throbbing through his thin swim trunks.

Casey, staring at what was obviously a very large, very erect cock, felt a throb of desire herself. Her nipples hardened through her swimsuit, which did not have any padding to hide them.

Josh, nose embedded in Mel's very damp crotch, moaned, sending a wave of wrongful pleasure through Mel.

Dave and Rob, both better able to hide their boners behind the front seats, stoop up to catch Josh, revealing their "masts" in the process.

They got Josh off Mel, but not before everyone had seen the soaking damp pool of wetness that was the woman's swim bottoms. Some of it was even smeared on her thigh. Casey was impressed.

Mel blushed. "Um... Casey's advice just got me, you know... turned on?"

They all looked at each other.

"...yeah. Me too," said an embarrassed Josh, pointlessly cupping his monster cock.

Another silence.

"Yeah," Rob agreed, tearing his eyes away from Josh's cock. "Hot."

They stood there for a moment, all throbbing silently with desire.

Then Mel suddenly leaned forward and kissed Casey on the lips. Casey could taste the beer on her lips, feel her body sprawled across Casey's chest. That warm, smooth, olive skin.

For a moment, Casey didn't reject her. The kiss lingered. Deepened.

Then Mel, as if suddenly waking up, jerked off her, saying "Sorry, so sorry... had too much to drink..."

But Casey grabbed her arm and pulled her back, kissing her deeply. Feeling her soft, toned back. Enjoying her lithe body, pressed against her.

"Whoah," said Rob, dumbly, awestruck.

Dave, on the other hand, didn't look as pleased. "Mel, what the hell, babe..."

He was cut off as Mel broke from Casey and advanced on him in her lust, like a cougar on the prowl. She launched herself at him, legs wrapped around his waist, grinding on him, kissing him passionately. He couldn't resist her this way.

Before he could object, she had unzipped his pants, freeing his cock. Pulling her bikini bottoms to the side, Mel impaled herself on it, moaning. She started to ride him, out of control.

Rob, the cheeky bastard, was the first one to come out of shock. He walked over to Casey, unzipped his trunks and spread his arms, as if to say... ehhh??

Casey looked at him. She felt her stomach drop with arousal.

She nodded, then let herself be taken up into his arms, kissed hungrily. Then he flipped her around onto the bench, facedown. Pulled her bottoms off her ass.

As he plunged his tongue deep between her cheeks, she melted into a pile of goo, moaning. Her hand found its way to her clit, rubbing it furiously.

Dave, seeing this out of the corner of his eye while Mel fucked him, stopped her and turned her over the same way. Replacing his cock, he fingered his wife's g-spot with unmatched skill, making her squirm with pleasure. At the same time, he buried his face in her ass, tonguing her hole as he moaned. He'd wanted this for so long.

Distracted by his fingers, Mel didn't have a chance to object to being rimmed -- in fact, it actually set off an orgasm so intense she could hardly believe it. She never thought that her BUTT could be this pleasurable!

She decided then that she wanted more. But she wanted to do it the right way. With an expert. Someone with experience.

She reached an arm across to where Casey was obviously enjoying the same pleasures -- except that Casey already had two fingers in her ass!

Tapping Casey on the arm, she crawled over and kissed her. Then turned and positioned her ass towards Casey.

"Show me how to do anal? Please?"

Casey stopped for a minute -- Rob's fingers still embedded in her ass -- then she leaned forward and kissed Mel's beautiful asshole. Mel shivered.

Casey tongued her hole deeply, sending waves of pleasure up Mel's body. As she did so, she rubbed Mel's soaking wet lips, coating her fingers in her juices as she massaged her clit.

Once she had enough moisture, she replaced her tongue with a finger, rubbing Mel's ring gently in circles, the tip of her finger slowly inching deeper and deeper inside.

Moaning, Mel is already pushing back against Casey's finger. So Casey starts adding another one. Feeling this increased stretch, Mel tenses for a second... then opens her ring to allow the new finger. Casey slowly works her hole, in and out, a little deeper with each stroke. Finally, both fingers are embedded in her ass.

As Casey lets her get used to this width, she feels Rob again, twiddling his fingers inside her. She gasps, using her free hand to rub her clit. She's soaking wet.

Seeing the wetness, Rob can't help himself. He positions his cock at her soaking pussy, stopping as if to ask permission. Casey nods hungrily and he plunges his cock in deep in one stroke, his fingers still deep in her ass. She moans.

Now Mel is up to three fingers in her ass. Dave, seeing that she is ready, pulls his wife away from Casey, who is thoroughly distracted by cock.

Laying Mel on the sunbathing bench, he thrusts once, slowly, into her sopping pussy, watching her face to see her reaction. She stares back into his eyes in ecstasy as he fills her.

Then he comes back out, positions his now-lubed cock at her asshole. "Ready?" he asks, staring deeply into her eyes with love.

She stretches her neck up to his ear, sending shivers of sensation with her whisper: "Fuck. My. Asssss."

So he does -- slowly, teasingly, making his wife squirm with desire as he holds the tip in place, pressing in, making her want it. She loses her patience and starts bucking her hips onto him, sending him deeper.

He pushes a bit further -- she braces, feeling the stretch -- and suddenly, the head pops in. She moans, cumming, her asshole convulsing around his cock. It's all he can do not to cum immediately.

As she settles from her explosive orgasm, Dave turns her over into doggy position. He whispers lovingly back into her ear, "I'm going to fuck your ass now, wife."

Then he plunges in.

She gasps in pleasure, feeling the delicious ache of having her ass stretched, over and over. She feels so full, it's so intense. And it doesn't hurt, not really.

And so, as her husband cums, she cums again, and they collapse into a pile.