Resort Pt 00 The Setup

Dan and Penny's Room

"How do you want to introduce it?" Dan was laying his clothes out for the evening. They had been planning for this night for over two months (and thinking about it for much longer). Now that it was here, he wanted to make sure they did it right.

"I think we should just go for it." His wife, Penny, was checking herself out in the mirror, her hands smoothing out her skin-tight dress. "Tanya's so desperate, I bet she'd get down on her knees right there at the table and start sucking you off. God, wouldn't that be sexy-she's so turned on by the idea of swinging she can't even help herself? Just gets on the floor and embarrasses herself in front of everyone just so she can get some of this dick." She walked over to her husband and grabbed his dick through his bathing suit.

"You really think it'll be that easy?"

Penny pressed her hand against her husband's groin and started sliding it up and down, warming it up before reaching his stomach then reversing direction and plunging her fingers into his shorts where she wrapped them around his hardening dick. "I don't know. How do you think she'll react to seeing this?"

Dan smiled, "Only one way to find out."

Dan and Penny had been swinging for only a few years. It wasn't until four years ago, when they discovered FlipFlops, an island resort with a growing reputation as the place to go for swinging couples (unadvertised, of course), that they had really stepped up their game. Their previous two trips had been a success, nabbing a couple each time, but it wasn't until the second couple the previous year where they had truly started to understand the power they had over others and how they could use that to ensnare the ultimate prize.

"We have been friends with them for a long time," Dan said. "That could make it harder. Me and Fred go back to middle school."

"And Tanya and I only go back since we each started dating you guys and I can already tell what that bitch needs."

Dan had to shake his head, equal parts bemused, stunned, and turned on. He knew Penny; his wife had a competitive streak-she had since they first met-but she could still surprise him with the things she desired. Their first night together had only been a preview of that. After dinner she had invited him to her apartment and started kissing his neck, working her way up to his ear where she asked him about his previous conquests-her word. He'd told her of the various girls he had bedded and in response she bragged that she'd be better than all of them.

By the third date it had become clear "conquest" wasn't just a word Penny used casually. There was real meaning behind it. She tried to turn Dan into her newest trophy, but things hadn't worked out as planned. She had a game she liked to play: who could make who cum first. Not just cum first, but want it, need it, beg for it before exploding everywhere. Whoever shot their load first was the loser-again, her word-and would have to serve the victor. Dan had never played before but proved himself a champion, making his future wife cum all over his dick. The loss had shocked Penny at first, but she soon learned to derive a perverse sort of pleasure from it. A conqueror being conquered was not something to cast off lightly. Anyone could conquer a weakling. But to conquer a true sexual warrior? There was a challenge. And to be conquered despite being a proven winner? That was new. Embarrassment and shame followed, sure, but also a pleasure stronger than she had considered possible. The night Dan had fucked her silly, he stood up after and made her drop to her knees where he commanded her to suck every drop of cum off-and out-of his dick. It still sent shivers down her spine. Not to mention a flood of wetness between her legs.

"Yeah," Dan said, placing his hand on his wife's ass. "She's probably going to need a lot of help with it."

Penny tugged on her man's dick, enjoying the feel of it hardening in her hand. "Definitely. After being with Fred for all those years there's no way she can handle this."

"You think you'll have to put your hand on her head to help her get used to it?"

Penny laughed. "She'd have to get used to it pretty fast if that's the case. I plan on pressing that bitch's mouth down on this thing so hard she's going to choke to death on it. Can you picture that, baby?" Penny leaned closer to her husband's ear and started whispering, painting a scenario for him that they both hoped-and expected-to come true later that night. "Her gagging on this dick, eyes all watery staring up at you, Fred playing with himself in the corner because it's so hot watching his wife get dominated by a real man."

"Fuck, baby," Dan groaned, pulling his wife closer. He leaned in to kiss her, but she brought her hand up between them and removed her other from his pants at the same time.

"Not yet. Save it. I want there to be plenty in here for when you cum all over her. I want her covered, mouth, face, tits. All of it. That way she knows she's completely owned."

"Fine. But afterwards you're going to have to finish what you started."

His wife smiled, punctuating it with a sharp raise of her eyebrows, "Hopefully I won't be alone."

At Dinner

"So, how long you guys been coming here?"

Dan shrugged nonchalantly. "How long, babe? Three years?"

"About that."

"It's so beautiful," Tanay said, looking around. "You always have a good time?"

Dan and Penny exchanged a look. "Yeah. Matter of fact last year things got really wild."

"Uh oh," Tanya said, looking at Penny. "What you do?"

"Oh, nothing." But Penny made sure to give a sly little smile before sipping her drink.

Everyone at the table laughed. "Well," Tanya said, "now I have to know what happened!"

"Naw," Dan said. "You wouldn't be into it."

"Let me guess," Fred said. "Dan got so drunk he tried picking you up and you both fell into the pool. Like that time in college. Spring break down in Florida with what's her name?"

"Jocelyn," Dan said. "I ended up fucking her."

"Dan!" Tanya shouted, slapping his arm.

"What? We're all friends here. Nothing wrong with talking about the old times. Plus, you want to talk about wild."

"Penny! You don't mind him talking like that?"

Penny shrugged. "He's my man now. Doesn't matter. Besides, I know she doesn't hold a candle to me."

"That's right. See, Tee? Trust. That's very important. Especially when things start getting wild."

"Oh my God, you guys." Tanya shouted. "Just say it already."

"Well...naw. You wouldn't want to hear it."

"We do! Right, Freddy."

"Sure," her husband agreed, though he didn't sound too enthusiastic.

"You'd just judge us," Dan countered.

"No I wouldn't!"

"Pen?"

"She's very judgy."

"You guys are awful," Tanya said, pouting.

"No, it's because once you hear it you're going to look at us and be like, 'Oh my god I can't believe they did that.' Dan said in a mocking tone. "And then when this trip is over you're going to go back home and tell the whole group about it and talk about us behind our backs."

"We would never!"

"I'm just saying. Penny?"

Penny smiled again and shrugged while she took another sip from her drink. She loved watching her man work. Whipping potential conquests into a frenzy, getting them to beg before they even knew what they were begging for. It made it all the sweeter when they finally found out what they were asking for, and ended up begging for it anyway.

"Alright, alright," Dan said, making a big show of waving his hands to calm everyone down. "Let's just say we met some people, another couple, and we all became very good friends."

Fred laughed. "You're a jerk."

"What?" Dan asked, incredulous.

"You just are."

"What?" Tanya looked back and forth between her husband and his friend. "I don't get it."

"Dan is just bullshitting you."

"No I'm not. Honest."

"So, you like, did what...exactly?" Tanya asked, genuinely lost.

Penny giggled, but this time she decided to get in on the act. Playing with her straw, she looked intently at Fred then put it between her lips and sucked. She didn't have anything against Fred. He wasn't horrible looking-at least he was somewhat tall-but beyond that she couldn't conjure too many positives. He always struck her as boring-borderline lame-and as far as physical features went he had nothing worth talking about. The real prize was Tanya. After Pen finished with Fred-which would be more like work than she wanted-she would have her fun with his wife.

"All I'm saying," Dan continued. "Is that we had some very good times. Isn't that right, hunny?"

"That's right, baby."

"I still don't understand."

Penny loved this. Watching her friend honestly grapple with what was being said. Six years with Fred; no wonder she had no imagination when it came to sex. They had talked-as all friends do-and from what she told her Fred was fine. Just fine. A nice enough dick. A nice enough fuck. But someone who seemed more interested in getting into a rhythm-not the fun kind-and leaving it at that. If they could pull this off, Penny could see Tanya never being the same afterwards. As a matter of fact, that was the goal. A longtime friend turned into a longtime fuck slave. It would be so convenient. And who knew, maybe the start of a sexual conquest that encompassed all the other couples from their group of friends. The possibilities were limitless.

"Tee, come on." Dan said. It was never clear to anyone, even his wife at times, if he was being sincere, smug, condescending or some combination of the three. Either way, it worked miracles with people, keeping them off balance, leaving them eagerly wanting to hear more. He was impossible to trust which made him endlessly interesting. A puzzle in need of solving. "You're an adult. Pen's an adult. I'm an adult. We're all adults here. I think we can all read between the lines."

Tanya's head tilted to the side. She hated looking like an idiot, but she'd rather appear naive than perverted. At least in public. She knew what Dan was getting at. Of course she knew. All he did was brag. Every party, every cookout, every dinner date, every brunch. He never passed up an opportunity-overt or otherwise-to flaunt. Whether it was his clothes, the money he made, or the women he fucked, he loved rubbing it in everyone's face, especially his friends. Even Penny at times seemed more like a trophy than a wife. Not that she was a "trophy wife," Tanya thought. She was far too successful and driven to be that. But it certainly felt like Dan enjoyed showing her off. Look at this beautiful, ambitious woman and look who she's with. That was the message Tanya always got when they hung out. It was exhausting-not to mention a little off putting-but the part that got to her the most was that they were probably the couple they clicked with the most out of all their friends.

Fun enough to have a good time with, but down to earth enough not to be reckless whenever it came to making plans they knew who to go to first. She knew Dan and Penny felt the same. After all, they did ask them and only them to join them on vacation.

"Alright Dan, I guess you're just going to have to spell it out for me." If this was the game Dan was going to play, then Tanya would make him play it on her terms. No gross innuendo, no mind games, no making her look foolish. If he wanted to talk about this stuff-Fred had told her all about Dan's comments in group chats with the guys, how he had insisted he had had threesomes with Penny and her friends, and other sexual exploits-then she'd make him do it on her terms: out loud, in public, and, hopefully, in a way that finally made him feel a little shame. Though she wondered if he was capable of feeling any.

Dan let out an exaggerated sigh. "Alright. But if it gets too heavy, just remember I warned you."

"I'll try to keep from fainting."

"Penny and I met a couple last year and after talking for a while, and drinking, and getting to know each other on a personal level, you know, making sure they were good, honest people, we all decided as a group of consenting adults to go back to each other's respective rooms with each other's respective spouses and spend the night."

"Bullshit," Fred said, putting his hand to his mouth to form a mock bullhorn; a relic from his more immature years that he had somehow never dropped.

Tanya hated whenever he did stuff like that, but in this instance, she needed all the support she could get. "I agree. I call bullshit."

"See," Dan said, looking at Penny, "I told you they wouldn't believe me."

"You were right, baby."

"Penny! I can't believe you let him talk about you like that."

"Like what?"

"Implying that you're sleeping around!"

Penny smiled. Shrugged her shoulders. Took another sip of her drink, this time keeping her eyes on Tanya, telling her friend everything she needed to know.

Tanya got the message. "Holy shit, you're serious?"

Again, all Penny did was shrug and smile. She enjoyed playing aloof. Letting her prey know what she was planning wasn't her style. At least, not until she had them where she wanted them.

"Penny!" Tanya shouted before quieting down and whispering the rest. "You slept with a stranger."

"Cameron wasn't a stranger."

"Cameron! I can't believe it. No, no. This is bullshit. Dan put you up to this. I refuse to believe otherwise."

"That's fine. Doesn't change anything."

Tanya was torn. That Dan could do something like this seemed possible-even likely. He had the attitude, the bravado, but she assumed his infatuation with Penny-if she could give Dan one compliment, it was that he seemed to worship his wife-would keep him from pursuing a swinger lifestyle. But Penny. For all her drinking and partying she never pegged her as...this! A willing participant in swapping sexual partners. The very idea of her being with another man was too wild to be true.

"I just can't believe it."

"Fine. Here." Dan reached across the table and pulled up a picture on his phone: Dan and Penny sitting at a table with another couple. All of them smiling, clearly drunk.

"That doesn't prove anything."

"I could prove it to you," Dan said. "But if you're already having a hard time with it then I don't know how you'd feel seeing it."

"Oh, what, you took pictures?"

"Well..."

"Gross!"

"It was a special night."

"Just show her the texts," Penny said.

"I can't believe this. Penny, why are you playing along?"

Penny took another sip from her drink, this time glancing at Fred. He fixed himself immediately, clearly getting turned on not just by the conversation, but by the look his friend's wife was giving him.

Dan tapped his phone then held it to his chest. "Now, there's some explicit stuff in here. Some very personal information."

"What, you give her your social in order to pay her off?"

"Very funny, Fred. No. No payment needed. Just some personal views exchanged between me and Jessica."

"Jessica," Tanya repeated in disbelief.

"You want to read it or not?"

"Yes, yes. Sure. Let me read this bullshit."

"Ok. No judging. I know you."

"Whatever."

Dan put his phone on the table and slid it over so his friends could read.

Jessica: Hey, hope last night went the way you wanted it to [smiley face emoji].

Dan: Perfect. You were great. How's Cam?

Jessica: Fine, I guess. I haven't really asked.

Dan: Penny said she had a good time so that's good.

Jessica: Prob not as good a time as me [winking face emoji].

Dan: I aim to please.

Jessica: You did more than aim.

Dan: You guys thinking of doing the resort again next year.

Jessica: I'm thinking there's no way I'll be able to wait a whole year before getting that big dick back in my mouth

"Alright," Tanya said, pushing the phone away and sliding it back across the table. "I get it. It's a big joke. What? Did Penny text you that or something?"

"Tee, you really think we'd go through all this just for a stupid prank?"

"Do you believe this?"

Her husband rubbed his face, laughing but not really laughing at the whole situation. He shook his head noncommittally then didn't add anything else.

"Freddy! You're no help here."

"What do you want me to say?"

"Support me. Tell me I'm not crazy for thinking this is a big joke."

"I honestly have no idea. After...what...twenty years of knowing this joke you think I can tell when he's bullshitting or not?"

Tanya couldn't believe how useless her husband could be at times. Especially when it came to Dan. It was like he'd been beaten down by years of their friendship and just ceded all control to him. Which restaurants they went to as a group, which bars afterwards, even who got to use their credit card to pay at the end of the night. Dan, Dan, Dan. It made Tanya sick. She wanted so badly to catch him in a lie. To rub it in his face that she had outsmarted him.

But the more she thought about it, the less likely this seemed like a joke.

"I still don't believe you."

Dan sighed and looked at Penny. "I dunno, babe. Should I just show her the pictures?"

"If you want."

"I don't think it's right because those are private pictures of me and Jessica. But if it's what it takes to prove it." Dan tapped around on his phone then held it to his chest just like before. "Ready? Are you sure?"

She wasn't, but curiosity had taken hold of her. All the talk had made it impossible to let this go. But why? Was she really so eager to see whatever was in this picture? To see Dan with another woman? Maybe she just wanted to call his bluff; see how far he was willing to take this. But there was another side of her, the side that hadn't wanted to toss the phone away; that had wanted to read more. And now this picture. What would it be of? Would it prove the text right? Not just that Dan had slept with this woman but the other part, about Dan's...

"You know what, sure."

"Fred?" Dan asked, looking at his friend.

"I've fallen for too many pranks where you tell me I'm going to be looking at one thing and then you show me a picture of your dick."

"You sure?" Dan asked.

"All set."

"So you're just going to let me show your wife a picture of my dick?"

Tanya's heart raced.

"No. Because I know you'll either chicken out or it'll be something else."

"Alright. Fair. Then I'll just show Tanya. Fred doesn't get to look. Ready?"

Tanya scooted up in her seat, excited, though not exactly sure why. Suddenly she wanted it to be true. To see this salacious thing. She could feel herself smiling and fought to keep it from getting out of control.

"You sure? Don't scream or go crazy or anything. Control yourself."

"Oh my god, Dan just show it."

Dan looked over at Penny, winked and smiled, then turned the phone over.

There was a woman. She looked like the girl from the picture, but it was hard to tell. Her blonde hair was pulled back, her makeup streaking, and she was down on her knees with a thick, firm dick in her mouth. Jessica, if that was her name, stared up at the camera, almost adoringly. Something in Tanya's brain told her to look away, warned her that she was staring, but for a brief moment she didn't care. Her pussy was tingling and there was definite wetness there. Without thinking she started rubbing her thighs together. Dan flipped the picture and the next one was similar except in this one he was clearly holding the girl's head down on his dick. Her eyes bulged, watered. She was clearly choking on it. Tanya couldn't blame her. Dan flipped to the next picture and again it showed Jessica from the same angle, staring down at her with her on her knees, except this time her mouth was free of Dan's dick. The reason was obvious: Her face was covered in cum. And she was smiling. Smiling! In the bottom left of the frame, Tanya could just see the head of Dan's dick. Her mind immediately began doing mental math. Adding the tip to the amount that had been sticking out of the girl's mouth in the previous pictures. Not to mention the unseen parts. When she realized she couldn't figure out how big it was she shook her head and looked away. Trying to act as nonchalantly as possible she laughed, but then nothing came to her. No witty remark. No quip. Her stomach was in knots, and below that... she couldn't think about that right now.