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Chapter 5
What should you do?
Allow the kiss
While you're afraid of the consequences, there's a side of you that wants to see....something. Although at the same time, you don't want it to be Uncle Rick and your girlfriend doing it.
Maybe, you can risk taking it just a little further, and see what it's like. You can always stop them later, right? It's just a kiss...
Rick: "...well?"
You clear your throat, as nervous as you've ever been.
You: "uhm....just one kiss, right?"
Jen: "Yeah...no big deal."
Rick: "No big deal" he says, shrugging his shoulders.
They then stand up, like you did when you kissed Jen. When they do, you realize you didn't consider one tiny detail. This is not just a regular kiss. This is a kiss, while they are butt naked, while he has a raging erection, and Jen is more aroused than she's ever been. When they embrace, you can't help but think you've made a mistake, a huge mistake. Maybe you should have listened to your dad. You should say something, but you swallow your words and turn the hourglass that counts the time they should kiss.
After they embrace, and press their naked bodies together, they look each other in the eyes, deeply, and laugh a little in their shared nervousness of what they're about to do. Jen's large, perky breasts are now pressed tightly against Rick's thick chest hair. Rick's erect cock is just kind of sandwiched between them, reaching far above her navel, smearing little bits of precum on her smooth, silky, taut stomach.
They are so much on the opposite end of the spectrum of sexuality and sensuality, that their contrast makes for a disturbingly beautiful image. He's a man, and she's a woman, it's like watching a nature documentary.
Jen has to stand up on her toes, and Rick has to lean down slightly for their lips to meet. They kiss, kind of shyly at first, then after a few seconds, they start using tongue. Jen takes a deep breath through her nose, enjoying Rick's scent, while Rick's big, muscly hands explore her back, eventually finding their way to her butt. Jen lifts herself further up on her toes to allow him easier access.
Wait a minute, the card didn't say anything about fondling....they shouldn't be doing that.
But you say nothing, as Rick grabs Jen's ass cheeks firmly, and effortlessly lifts her up. Jen crosses her legs behind him, planting her pussy on his stomach, leaving her own mark on his body, like the precum he left on her. Rick's cock is now nestled comfortably between her legs, sticking out from under her lewdly, still leaking precum, and beating in rhythm with his heartbeat, which, has clearly gotten faster.
Their kissing has grown wilder with each passing second, Rick seems determined to explore every crevice of Jen's mouth. Meanwhile, Jen seems equally determined to let him, she really meant it when she said she wanted to go wild. You suppose it's all those years of suppressed sexual frustration in high school just venting out now.
Jen had always rebuffed the advanced of even the most popular and handsome guys in high school, and even college. Believing that she was saving herself for the right man, or just blindly following the catholic churches code of abstinence over contraception. In any case, she certainly doesn't seem repressed now, with your Uncle Rick.
You are unsure if that's a good thing or not.
Jen has started to instinctively grind her hips back and forth, stimulating herself on Rick's shaft, and moaning slightly. The thought enters your mind, maybe she is just trying really hard to win the game. The goal for her is to make both the men reach orgasm, so maybe she isn't actually this into it, just playing the game right.
You snap yourself out of your thoughts, and look at the hourglass. It's spent already, you have no idea how long they've been doing the "1 minute kiss" for. 2 minutes? 5?
You: "Uh...guys? Times up..."
You look down at your crotch, now your dick is at full mast, only after watching Jane make out with and dry hump your uncle, and your hand is unconsciously wrapped around your 4.5 inch shaft. What's wrong with me, you think.
After about 10 more seconds of ignoring you, they finally part their lips from each others.
Rick: "huhh.....you sure? Felt short..."
Jen: "hah...yeah..."
You: "Yeah....no I'm sure..." They have no idea how long they actually took either.
They're both completely out of breath, Rick's still holding Jane, his cock beating with senseless arousal. When he let's her down slowly, he keeps his cock between her legs, then slowly slides it out, stroking her pussy with the entire length of his cock, leaving a trail of her nectar on his cock. Jen moans slightly and supports herself on his chest.
Rick: "Sorry...."
Jen: "Yeah, no....problem...."
They sit back down, clearly angsty they didn't get to continue. Jen's face is completely flushed, and Rick's cock and stomach are covered in her juices.
Rick: "Fuck....I don't know how much longer I'm gonna last, you might just win this game, Jake."
You: "Why's that?"
Rick: "To be honest, after you showed me that picture of Jen at your graduation party, I haven't jerked off, or had sex, even once. I am absolutely bursting, man."
You: "Gross..."
Jen: "Oh my, why'd you do that?"
Rick: "It probably sounds weird, or kind of gross, but after I saw Jen's picture, something told me that jerking off anymore was wrong. A man's seed should go to a woman." He says while gesturing to your naked girlfriend next to him.
You: "Ugh..."
Jen: "You know what, the church agrees with you. So I agree, it's unnatural to masturbate. That stuff should be between man and woman, not man and....sink, or paper towel." She says, seemingly ignoring the fact that Rick has purposefully saved his cum for a whole week just for her. Was he planning on this the entire time? And why does she seem to like that fact?
Rick: "Exactly. So, I've got to thank you, Jake. For not only showing me this goddess of a woman, but bringing her on this trip with me, that was a really, really cool move, man." Uncle Rick tells you this, while buck naked, sporting the biggest erection you've ever seen, only a foot away from your very naked, and very aroused, girlfriend.
He smiles towards you, the sides of his mouth still wet with your girlfriends saliva. Some part of you is happy that you managed to impress your cool, rich, uncle, another is angry that he just got with your girlfriend like that, and clearly wants more.
You: "Yeah. You're....welcome...." Unsure of what to say. You want to stop this, but the butterflies in your stomach, and your desire to impress your uncle urge you onward. Did you just say he's welcome to your girlfriend? What the fuck?
Rick: "Well, it's Jen's turn. And since one player is past this point, we switch to this deck, and we only draw cards from now on, each turn." The new deck as an "****" tag on it, which must mean the kid stuff is over now.
Jen quickly draws a card from the new deck, and reads it aloud.
Card: "JEAPORDY: Female receives oral from both males for one minute each. Starting with the male on the left hand side."
Rick: "ooooh, you're in for it now. I'm gonna make you cum so hard, girl."
Jen laughs, and bows her head in embarrassment. Her cheeks somehow turned even redder, they compliment her silky smooth auburn hair well.
You feel yourself becoming more nervous, and sweatier at the thought of Uncle Rick putting his mouth on Jen's pussy. With the express purpose of making her orgasm. Of course, Rick shouldn't be doing any of that with Jen, but you met such fierce resistance when you objected to the kissing challenge, that you hardly feel like you could even stop this if you wanted to.
Goddammit, why did I let this get so far? Don't worry, it's just oral, ok? That's okay, right? That's not cheating. You think to yourself, justifying to yourself Rick sucking on your girlfriends pussy right in front of you.
Wait, if I get to go first, and manage to make her orgasm, I win the game! And Rick would have to just jerk off or something in his room, nowhere near Jen! This thought makes you feel a lot better about your current situation. There's a chance here for you to reclaim your relationship with Jen as something just between you two, and establish some boundaries between Rick and Jen. You steel yourself for the coming challenge, you can do this.
You: "I'm first, Uncle Rick. Get ready for the game to end, I'm gonna win!" You say in a strange sort of false confidence, as if you're okay with what's going on. You're not, but....
Rick just shrugs and laughs in a let's see kind of move.
Rick: "Here, we can go to the sofas on the wall." he says, stands up, and leads Jen by the hand to the sofa, his erection bobbing up and down with his steps. Jen's shapely curves are so distracting, how is her body so damn perfect? She sways seductively towards her seat, her perky butt just begging to be grabbed, fondled, worshipped. Since there is zero sag in her bottom, the tiniest hint of her slit is visible, teasing the two aroused men in the room incredibly.
Jen: "This is kinda embarrassing....I've never done this before...." she says as she sits on the edge of the sofa, her legs closed and her hands flat on her thighs.
You: "Me neither...maybe we should just stop." You say, **** to stop whatever the fuck is going on.
Rick: "Nonsense! Don't be embarrassed. You are two young lovers, eager to explore each others bodies. There's hardly anything more natural and beautiful than that." The most annoying thing is that he's right. It would be beautiful if your 45 year old hairy, big dicked uncle wasn't there to witness it, and worse, take part in it! That can't be natural.
Jen: "Yeah....you're right, I suppose. I'm just so nervous! Kissing was one thing, this is....something else." she chuckles, squeezing her thighs with her hands.
You: "Yeah...."
Rick: "Don't worry, it's a good thing I'm here, I can help you out getting through the first awkward steps, ok?"
How nice of him....
Jen nods, as Rick approaches her on the sofa. Then, very gently, he takes one of her feet in his big hands, and caresses the length of her shin bone, and kissing her toes. After a little while of this, as well as the other leg, Rick moves up to kissing her thighs, and spreading her hands apart, until they're at her sides, palms flat on the sofa. Then he moves on to kissing her pubic bone, then her belly button, then he moves up to her left breast, taking her nipple in his mouth and sucking on it. Jen just looks at this big, burly man having his way with her body, pleasuring her, relaxing her, and moans slightly. Her shoulders have definitely dropped, and she's leaning further down on the sofa as Rick pushes into her, switching to her other breast, and massaging the other with his hand.
After a little while, Rick cranes his neck towards Jen's head, and kisses her deeply, which she seems to welcome. His big hands wander back down to her knees, separating them gently, as he nestles himself between her legs. Their genitals must be pretty close by now....Is he going to fuck her?? You can't really see anything, Rick's body is so thick that Jen is almost completely covered.
Thankfully, he slides down between her legs, and licks her soaking wet pussy with a wide tongue, lapping up all that pent up lubrication she's accumulated over the evening.
Wait a minute, I was supposed to go first!
Rick: "Holy fuck, girl, you taste so good....best pussy I've ever tasted...." he says as he goes in for another lick, and another
Jen moans, grabbing at her heavy breasts. Your eyes focus on her silver cross necklace, symbolizing her purity and her faith. Then your eyes lock in on Rick's hairy back, his head buried between your girlfriends shapely legs. Your cock is so hard it hurts right now, but you resist the urge to jerk off, you have to win this game.
You clear your throat, to remind them of the rules. Rick stands up and sighs. "Right, you were first, nephew. I've got her all warmed up for you." he says as he stands up, leaving Jen completely exposed on the sofa, revealing her most private parts in a way she's never done before. Your heart beats faster, while you bask in the sheer sexuality of your girlfriend baring her pussy to you. Shame it's also being looked upon by your Uncle Rick, who is clearly thoroughly enjoying the spectacle, as he stands there with his rock hard cock just besides you.
Jen: "You...like it...?" she asks you
You: "You're....beautiful....of course I...."
Rick: "Ok, ready? Go!" Rick says as he quickly flips the 1 minute hourglass.
You were not ready yet, but you dive in anyway, until your mouth meets Jen's sweet, pink, pussy. The taste and smell was not exactly what you were picturing, and what Rick had just described. After he just finished licking up her juices, initially it just tastes like Rick's breath, like coffee and whisky, and old man breath. Fighting through that, you start licking her pussy...somehow.
It dawns on you, despite your initial confidence, that you have no idea what you're doing. You've seen this in porn, a thousand times, but doing it is so much more difficult. Your jaw is already tired, and how are you supposed to be using your tongue? Up and down? To the side? You decide on doing some sort of semicircle movement with your tongue, but you can't really get into it, since you're **** to crane your neck so much it hurts. Jen is not responding much to your efforts, even though she is clearly very aroused. It must be because she's trying hard not to cum, of course, otherwise she would lose the game. Weirdly, you seem to be losing your erection slowly as this goes on.
Rick: "Alright, times up! Doesn't look like you had any luck, nephew."
Jen: "Sorry baby, I was trying not to cum...It was really good though!"
You: "Yeah...good job..." You say, wiping her juices from your mouth.
Rick: "My turn, move over."
Rick quickly replaces you between Jen's legs, eager to taste her young pussy again. He wastes no time waiting for you to turn the hourglass, before diving head first into your girlfriends pussy. You stand up slowly, and you notice your erection has fully returned, almost instantly after Rick touched Jen again. Jen responds almost immediately, with a much stronger reaction than what she displayed with your performance. You can't really blame her, he's clearly a pro. He's displaying moves you never would have thought of, and he grabs her butt and just lifts her to give him better access. He uses his tongue wide, narrow, he knows when to suck, when to pause, and when to attack. Jennifer grabs his hair in desperation, and squeezes. Her breathing has become really ragged, and sweat has started to bead on her voluptuous tits.
The way she's reaching down to Rick's hair causes her breasts to push up lewdly, you stare at them, mesmerized by the way your girlfriend looks, and how her pussy sounds when Rick sucks it. You start jerking off in front of them, which Jen notices, giving you a darting glance and smiles in the corner of her mouth.
You don't really realize how much time has passed, but it dawns on you: You never turned the hourglass! They must have gone over the minute already....
You: "Guys? Times up..."
Rick: "aaah....damn..." he says as he pulls his mouth off Jen's pussy.
Jen: "huhhhh...I was so close...."
Rick: "Man, you are seriously good at this game, girl..."
Jen: "mmm....thank you!" she giggles
Rick: "My turn, then!"
Rick stands up, draws another card, and reads it aloud.
Card: "FINISHER: Males take turns fucking the Female. Vaginal, 2 minutes each. Starting with the Male to the left of the female."
Rick: "Oh boy, here we go!"
Jen: "...oh my god..." Jen says as she lies there on the sofa, naked, legs splayed with her virgin pussy on full display, seemingly no longer shy at all.
You: "We can't do that....that's too much, Uncle Rick!"
Jen: "You....don't want to have sex with me?"
Rick: "What? How can you not want to have sex with this beautiful, sexual goddess with her pussy right in front of you?"
You: "What? No! I do!"
Rick: "Then what's the problem?"
You! You shouldn't even be here! Can you just go? You say in your head as you stare at Rick, both of you buck naked, but dare not say, inciting Rick's anger is not something you're particularly keen on doing. Not after all the nice things he's done for you, and Jen. And still, despite all he's done tonight, with your girlfriend, he's still someone you really want to impress. If your cool uncle Rick thinks you're cool, then maybe you're not such a loser after all, despite what the bullies in school always said.
You take a deep breath, and calm yourself, despite all your anger towards Rick right now, you need to calm down to not seem crazy right now.
You: "It's just, a little much, isn't it? I mean, you're my uncle, Rick, you shouldn't be fucking my girlfriend, it's not right. Anything that happened until now, that was exciting, but this is too much for me."
Rick: "I completely understand, buddy."
You: "You do?" Wow, you really didn't expect him to say that.
Rick: "Yeah. Society has fooled you into thinking monogamy is the only way to have a healthy relationship. And it's just not true! Plenty of couples have multiple sexual partners, with no problems! Hell, I shared in a relationship with some very good friends of mine, and they're happy and healthy with a child right now. A normal family like any other."
Jen: "That's beautiful...."
You: "No, that's not what I mea...." Rick cuts you off with his hand on your shoulder.
Rick: "Trust me buddy, this is the right move. We're gonna have a lot of fun on this yacht trip, and it starts right here. I know you want to have sex with Jennifer, go ahead. You're first, I don't mind waiting...."
Jen: "We've been waiting a long time, baby....I never could have done it at my place, and your place wasn't good either. This is the best we're gonna get."
You feel cornered, with no way out. Maybe they're right, this sinking feeling in your stomach will all go away after this. So you just nod.
You: "O...okay....of course I want to have sex with you Jen, you're the most beautiful girl I've ever met in my life." Jen smiles back, her pussy inviting you in between her legs.
This is it, you're finally going to have sex with Jen. It feels weird that you're not even going to put a condom on, but Jen insisted. You're not really sure you want to have children yet, but you're too horny to think about that right now. You retake your place between Jen's legs, and line your hard dick up with her pink pussy.
You: "I....I think I love you, Jen....."
Jen: "Oh baby.....I think I love you, too...."
You: "You ready...?"
Jen nods slowly, you push your dick slowly inside of her pussy. It's the best feeling in the world, the way her velvety canal envelops your hard dick makes you feel like heaven. She's so wet, there's hardly any resistance to you pushing your dick halfway in. This feels so good, you don't ever want to leave.
Rick: "Woah, slow down, what about a condom?" He says as he holds up a couple of magnum condoms, as if they'd ever fit you.
You stop with your dick only about halfway in: "Uhm...Jen is a devout catholic..."
Jen: "Yeah, we're not allowed to use condoms...."
Rick: "Well, well....so, you guys are ready to have a baby....?"
You and Jen look each other in the eyes, your dick lodged halfway into her tight love canal.
You: "uhh..."
Jen: "I...hadn't really thought about it...."
Rick: "So, put them on...?"
Jen: "No, I couldn't. Sorry....maybe it's best we just stop here then...." She says, with obvious sadness in her voice.
Rick: "Better pull out, then, nephew....rotten luck."
You can't believe this, how could she not have thought about that? You brought it up back home, you offered to bring contraception, but she said no! Jennifer seems awfully sad, though, maybe she is feeling conflicted about her faith. God, she's sexy, but....you want this too bad, you've come this far, you're not pulling out now. The only thing keeping you from going crazy right now is that Rick also can't fuck her now. Maybe this trip can be salvaged after all, and things can go back to normal.
Then, Rick places his big hand on your shoulder, snapping you back to reality, and you stand up, leaving your halfway wet dick sensitive to the air. Sitting down on the sofa next to Jen, still with her legs up, and pussy on full display, you want nothing more now than to fuck Jen again. But, it can't be done. You draw a deep breath, then sigh.
You: "We should just....huuhhhhh.....go back to drinking....play another game, huh?"
Surprisingly, Rick just takes your place in front of Jen, and starts slapping his hard, veiny cock on her pussy. Jen starts moaning softly, and bites her lower lip. You could swear you could visibly see her pink nipples get harder.
You: "Wh...what are you doing, Uncle Rick? You can't fuck her either...."
Rick: "Sure I can. See, I never wanted any children, so I've had a vasectomy done years ago...."
Jen: "nnn....what's that?"
You: "It's a procedure where the production of semen gets cut off from the rest of the cum." You answer before Rick gets a chance, proud of your knowledge of biology.
Rick: "That's exactly right...." He says while slowly rubbing your girlfriends wet pussy with his veiny, old man cock, coating it's underside in her love juices. "So, that means, even if we have unprotected sex, you won´t get pregnant, no matter what."
Jen: "hnn...oh wow....that´s amazing...." she says while slowly rubbing her breasts, and playing with her rock hard nipples.
You: "Wait....I'm not sure this is a good idea...."
Rick: "Look at her, Jake, look at your girlfriend. After all the foreplay tonight, she needs a proper release. And so do I, I haven't cum in a week, remember! If you deny us this pleasure right now, I guarantee she'll hold it against you in the future, tainting your relationship."
Jen: "Pleeeaase, baby? I....really wanted to finally have sex....I just wish it was with you first. But, the condoms...."
You: "I wish we could, too! Maybe we can just use condoms this one time?"
Jen: "I...can't....I'm so sorry....."
Rick: "Like I said, no need for me to use a condom. This is like a free pass to have unprotected sex, something that's not a sin, right?"
Jen: "Right...."
Rick: "Besides, you got to stick your dick in her. It's only fair I get to try the same, right?"
At this point, Rick has started grinding the length of his shaft against her wet pussy, generating some disgustingly arousing sounds.
Jen: "I...guess it's only fair...right? And It's in the rules...." she doesn't even look at you, her eyes are fixed on the giant one eyed trouser snake rubbing up against her pink pussy.
Rick: "Yeah, man, it's the rules...."
You: "I...uh..."
Continue the game?
The Summer Sailing Trip
With your Uncle Rick and your Girlfriend Jennifer
Older man takes a young couple on a two week sailing trip, and expands their horizons.
Updated on Sep 21, 2023
Created on Nov 13, 2022
With every decision at the end of a chapter your score changes. Here are your current variables.
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