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Chapter 6
Continue the game?
Yes
You: "Okay...but just for the minute, ok?"
Rick: "Yeah, of course." He says, visibly happy as he pulls back and lines his cock with the entrance of your girlfriend's tight pussy, and pushes in.
Jen is so tiny compared to Rick, his cock looks like it wouldn't even fit, and if it did, it would split her in half.
To your surprise, Rick is able to push half of himself inside her without much resistance. Jen takes a deep breath and puts her hands on Rick's shoulders. She must be completely ready for him, after all the foreplay and teasing from the board game. You can tell from here her labia is fully engorged, accepting Rick's cock inside her with ease, even though she's a virgin.
Rick: "wow, I've never been able to push in like that. You really are the perfect woman..."
Jen chuckles: "hahh...thanks...nnn....I....do a lot of horseback riding..." That must be why her hymen hasn't torn during this, she's already torn it as a teenager during horseback riding.
Rick: "Ffffff....uuuuckk....I can tell....that's tight pussy....shit..." he grunts while supporting himself up with one hand, and grabbing on one of Jen's naked breast.
Jen: "uuuhhhggmmmmm.....god.... you're.....so.... big....."
Rick: "We fit perfectly together, girl.....your pussy was made for me" Jen just moans in response.
You can't help but agree. Even though it's disturbing to watch your girlfriend with another man, there's a certain kind of beauty here. Nature is taking course, right in front of you. Man and woman, joined at the hips, no protection, not a singular thought in their heads besides giving and receiving carnal pleasure using their slightly sweaty, very naked, bodies.
It's impressive, really. Just a week after seeing a picture of Jen, Rick has his bare naked cock buried balls deep in her young, unprotected, pink pussy. The thought that he might not get Jen to sleep with him probably hadn't even crossed his mind, he just....takes what he wants. A part of you should be outraged, but your need to impress your uncle, and the desire not to be rude, keeps you silent, albeit left with a mix of anger, embarrassment, and arousal. Perhaps one feeling fuels the others, it certainly seems the further Rick goes with Jen, the more you get embarrassed, therefore angry, and therefore more aroused.
By the time you sit back down after turning the hourglass, Rick and Jen are locked in a deep kiss, while he just keeps his cock buried at the hilt. Your hand inadvertently starts jerking off your dick, with slight remnants of Jen's pussy juices still on there. Meanwhile, Rick gets to enjoy the wetness and warmth of her pussy freely, and to the fullest. Jen seems lost in the moment, dressed in nothing but her catholic cross necklace, she seems to thoroughly enjoy the feeling of Rick's big veiny cock stretching out her tight, virgin, pussy.
While Rick is exploring Jen´s mouth again with his tongue, he starts pulling out, slowly, all the way until he´s almost completely out of her, before pushing back in, almost as slowly. Jennifer can do nothing but wrap her hands around his neck, and moan into his mouth. Then he does the same move again, and again, and again. Jen´s moans get more intense, and her ability to hold the kiss wains, causing their combined drool to leak onto her naked breasts, just begging to be grabbed.
You can´t help but jerk off faster at this incredibly arousing sight. All your life since you´ve been a teenager, you´ve jerked off to porn, never really getting anywhere with the real girls. But this, this is better than any porn. There´s a sick sense of depravity about this that makes you feel like you have a lead ball in your stomach, but you don´t really want to remove it, even though it hurts.
After a few more moments, and full strokes of Rick´s cock in and out of her pussy, Jen is seemingly at her breaking point. The sweat perspiring on her chest is beading down, all the way to her naval. You follow a droplet of combined sweat, and drool, down her heaving breasts, to her belly button, where the sight of Rick´s big veiny cock invading your girlfriend´s unprotected pussy is unavoidable. His movements seem very deliberate, like a master artist, Rick is using his cock as a brush, rubbing her on her G-spot, with a eerie consistency in his movement and speed. Your virgin girlfriend seems to stand no chance against him, it's just a matter of time now....
While jerking off, you look over to the table with the hourglass, it's halfway down already. What happens if Jen manages to hold her orgasm back? Another round? It feels like it would be weird to sit back at the table, now that Rick and Jen have joined completely at the hip, with no protection. You look back, determined not to miss a single detail, even though it disgusts you.
Suddenly, Jen grabs Rick´s upper back, burying her nails in his hairy skin, leaving her fingernails white with pressure, her naked, slightly muscular, and toned thighs press against his sides, making sure he´s not going anywhere. She bites Rick´s lower lip what looks like quite hard, while screaming with her teeth closed. In a volcanic orgasm, her lower belly convulses, like she's having a small seizure, massaging Rick´s cock with her tight pussy while she orgasms all over him and his naked, hairy, mass of a body.
Jen: "mmmmmmfffffffffffffttraaaaaaaaaaaaAAAAAAhhhhhhh!" she bellows like a wounded animal. You'd never expect your nice, petite, catholic girlfriend making such primal sounds. Finally, her pent up sexual frustration, accumulating over the years since she was 16, are released. Shame it wasn't with you, and not with your uncles naked cock buried to the hilt in her pussy.
Could you even have given her an orgasm like that? Rick has a much bigger cock than you.....and he's obviously a master at this....can you even compare?
Jen's primal orgasm sends you over the edge as well, erupting semen all over yourself. You've never cum so hard in your life, your own semen shoots upward towards your chest, hitting yourself in the chin. You feel almost instantly completely embarrassed, as you have nothing to clean yourself up with. So you sit there, covered in your own cum, while Rick keeps his cock lodged balls deep in Jen's unprotected pussy.
Rick: "hahhh.....looks like I won....."
Jen: "Ffffuuuuck......yeah....dammit...."
The two lovers are breathing quite heavily, now, although Jen's breathing has become quite ragged as she comes down from her very first vaginal orgasm.
Rick: "Jake scored a own-goal, it seems...."
You: "I...."
Jen: "It's okay, baby. I'm glad you enjoyed this so much....." She says, through her heavy breathing, and gives Rick another deep kiss.
Then, as Rick is pulling out, you assume he's standing up. To your surprise, he pushes his cock inside her again, now fucking her in faster strokes than before. He's now moaning a little, or you could call them slight grunts, his voice is so deep. Jen only responds by relaxing again after her monumental orgasm, letting him take her however he wants.
You: "uhhh.....games over....right?"
Rick: "ffuu....yeah, so....? I haven't cum....yet...." he says, not skipping a beat in pounding Jen's pussy.
Rick is slamming his body down on Jen's petite form so hard now, their hips make these extremely lewd slapping sounds as Rick goes balls deep yet again in your girlfriend's pussy. Jen's silver catholic cross necklace, now covered in sweat and their combined drool, is now sliding up and down her sweaty breasts in rhythm with Rick's thrusts that bottom out in her pussy every time. You never would have thought your petite little catholic girlfriend could take a pounding like that, never in a million years. The slapping sounds of Rick's flesh against Jen's is almost deafening, yet tantalizing in the same stroke.
You: "But...."
Rick: "You two....came.....why...can't I? That's only...fuck...fair...." He manages to grunt the words out between strokes.
Jen: "YeAh! That's.....fair!" Jen manages to eke out those words in the middle of Rick's pounding, holding on to his large body for dear life.
Fuck....are they right? It's your fault for taking this so far....why should Rick need to suffer for that? But it's Jen, your girlfriend! Only you should be having sex with her, not your 45 year old Uncle Rick.....
You decide not to say anything, as they are sort of right, it makes sense....doesn't it? If you stop them now, Rick's gonna be super pissed, he just paid for this whole yacht trip, and it's the first day! You can't help but think the rest of the two weeks would be super awkward if you did that.
But why does he get to use Jen's pussy to cum, again? Just because he's had a vasectomy? He should just jerk off, like you did!
While you contemplate, conflicted in anger, embarrassment, and arousal, Rick has begun slamming his hips down, driving his cock harder than ever inside Jen's definitely no longer virgin pussy. It's too late to stop them now. Rick's cock is white with their combined juices from their coupling, and you can tell Jen's pussy has turned from a sensual shade of pink to a sexually aggressive shade of red. Your own dick has decided to wake up again, causing you to start jerking off again, using your own cum from previously as lube. Jen, sensitive from her previous orgasm, is now practically screaming through Rick's fucking. It's not like anyone can hear her, in the middle of the ocean, but it's unmistakable the effect Rick has on Jen.
A part of you would like to see Jen covered in cum, like in the pornos. You only wish you had has the chance to do that. You expect Rick to pull out in a few moments and do it himself, which both angers and excites you. No such thing happened, as after only a few more strokes, Rick bottoms out in Jen's pussy, groans loudly, and deeply, while his legs spasm, his face turns red, and his butt clenches.
It's unmistakable, he's ejaculating ropes of his sticky white cum inside of Jen's pussy, inside of your girlfriend. He'd only met her a few hours before, not counting texting, and now he's giving her her first creampie ever. And she let him, willingly, easily, she almost welcomed it. Right now her fertile womb is opening up to your uncles flood of cum, something he's been storing just for her for over a week, deliberately holding back his orgasm just for this very moment. His big balls contract up, to deliver all the cum they have to offer, and her pussy convulses in another mini-orgasm, squeezing his cock, milking it for all it's worth.
When Jen talked about going a little wild on this yacht trip, you had thought that involved wearing the new bikini, and fooling around in the cabin at night, once Rick had gone to bed after a day of sunbathing. You certainly didn't think the very first night would entail Rick taking Jen's virginity in front of you, and then creampie-ing her.
Rick is pumping so much cum inside of Jen, after a week of "saving up", that her tiny pussy can't even hold all of it, so some of it leaks down the walls of her pussy, even though they're impossibly stretched by Rick's thick cock.
Jen: "OH GOOOOOD......!!! I can feel.....you....cumming.....hnnn...." she squeezes out the words through what looks like another mini orgasm, although she could just be enjoying the moment of cum flooding her pussy.
Rick: "HNGRRrrraaaa.....yeah, girl...milk that cock.....take all my cum....just for you..."
Jen: "ughhhh.....such a good feeling....." your girlfriend says with her eyes closed, and her mouth open, holding Rick's mouth near hers, kissing intermittently in the throes of their orgasm.
You sit there, with your painfully hard dick in your hands, stunned, and covered in your own cum. Next to you, your girlfriend Jennifer, who has your Uncle Rick's cum deep inside of her pussy. Her beautiful auburn hair is now slightly soaked in sweat at the edges, evidence of the level of magnitude of the sex she just had with Rick. There's a weird kind of silence in the air now, while the two lovers come down from their high. You can hear Rick's excess cum drip down from their joined genitals, onto the floor, a sick reminder of what just happened.
Amusingly, Rick has goosebumps from cumming inside of Jen, causing his many hairs on his body to rise up, giving you and Jean a clear signals he has thoroughly enjoyed his time here. Who wouldn't? He's a 45 year old man, who just creampied his nephew's stunningly beautiful, 19 year old virgin girlfriend.
This must be what dad was warning you about, Rick obviously has some quality that women are drawn to. But how did dad know something like this would happen? Why didn't he just tell you? You're not sure you would have ever told Jen about the yacht trip if dad had just told you straight. You thought he was just being spiteful to his brother, by being against you going on a cool yacht trip.
After a few more moments, which felt like an eternity as time seemed to stand still, Rick starts to stand up again, slowly removing his cock from Jen's pussy. A small splash of cum hits the floor as he pulls out.
Rick: "Fuck. I think that was the best sex I've ever had! But....aaahh....my knees are killing me, after fucking in that position...." he says, standing up completely, and stretching out in front of Jen. His cock, still shiny from Jen's pussy, is semi hard at this point, but still dwarfs your own rock hard dick.
Jen: "mmmm.....yeah, my back isn't the greatest either after that..." she and Rick chuckle slightly.
You decide to stand up as well, partly to clean up, but mostly to see Jen from Rick's perspective. Her legs are still lewdly splayed apart, her pussy is seemingly bright red, except for the small river of cum leaking from her onto the floor. Her pussy is still dilated slightly from Rick´s cock, it´s strange. Her body is all slightly wet from their combined sweat and drool. Even some of Rick's disgusting body hair jostled loose and glued to her sweaty body. As you stand there, gawking wide-eyed at her post-sex form, she looks back at you, and bites her lower lip while massaging her breasts.
Rick: "Hey Jake, I gotta hand it to you, you've got yourself a really wonderful girlfriend there, I think you two have a bright future ahead...." You've got no words yet, it's like the lead ball in your stomach jumped up to your throat, leaving you unable to speak even if you wanted to.
Jane: "Aw, you're so sweet, Rick...." she fawns, closing her legs as Rick turns away, denying you a longer look.
Rick opens up a nearby drawer, pulling out a small folded towel, pressing it up to your chest, and says: "Here, nephew, you should get cleaned up. You can also help Jen."
Finally, you're able to speak: "Wh....did you have to cum....inside of her....?" You say, wiping your own cum off your body, and handing it to Jen, who starts wiping herself down, mostly catching the cum dripping out of her still.
Rick raises an eyebrow: "Why not? It's not like she can get pregnant from my cum, it's your cum we need to worry about. Vasectomy, remember?" He says as he shakes his cock up and down, still glistening with his and Jen's combined juices. "Shooting blanks over here, buddy...."
You: "Yeah...but you...she...was a virgin...." you say meekly. A part of you wanted to "claim" Jen as your own in this way, by taking her virginity. But Rick got there first. Technically, you had half your dick inside her before he did, but you got almost none of the benefits that Rick did.
Rick: "I´m disappointed in you, nephew, you should be more open minded. It doesn't really matter who takes the "virginity". You just have sex, it's not that complicated, or dramatic." While he says this, you get the distinct feeling from his expression that, despite his words, he's incredibly proud, and satisfied, that he just took Jen's virginity, your bombshell girlfriend who you were bragging to him about at your party.
Jen: "I...think he´s right baby. I mean, I just lost my virginity, and I can see now it´s a lot less of a deal now that it´s done." she says, now stood up next to you, and gives you a small hug and a kiss on the cheek, before continuing: "I'm glad my virginity is gone, finally."
Rick: "Although, I really didn't expect to just be fucking her in front of you. It's a real shame you can't have sex with her too." Rick puts his large hand on your scrawny shoulder, emphasizing the sort of sick dominance he's clearly displaying over you, and reveling in.
Jen: "I'm SO sorry about that, Jake. I guess I didn't really think this whole thing through....I don't know if a baby is the right move for us now...."
You: "No...yeah...I agree....I just wish we could use condoms instead...."
Jen: "Me too, but the church says condoms in place of abstinence is sin, an affront to the lord. I can't do that to Him, I hope you understand."
So, instead, it's better to have your boyfriends uncle fuck you in front of him, without protection? The Lord's okay with that? You dismiss your thoughts, not wanting to have an outburst of anger, rather choosing a cooler head.
You: "Yeah, I understand...."
Jen: "Thanks for being so understanding, you're the best boyfriend. I'm gonna go take a shower." She says and kisses you on the cheek, before walking like the naked supermodel that she is, with her perky butt and shapely thighs, to the shower that Rick pointed out.
This leaves you and Rick in the room together, alone. Suddenly, things are way more awkward than when Jen was in the room. Now it's just two naked men, one clearly physically superior to the other. You somehow feel a foot smaller than before, as Rick comes closer to you, towering over your scrawny form. He brings you in for a weird, naked embrace, giving you a taste of what Jen was feeling earlier. His thick body hair tickles you, but you can't help but focus on his still semi-erect cock poking you in the stomach. You instinctually open up your arms to greet the hug, but can't help but feel awkward and angry at Rick at the same time.
Rick: "Hey man, I really want to thank you for being so cool about everything so far. I know I was a little pushy, but I was just so horny from seeing that first picture you showed me, and from texting with Jen for the past week. You know what I mean? I'm so glad you guys came on this trip, I am so lucky to have you as my nephew, you know that?"
You: "I...can't believe that just happened..." You open up to Rick a little bit in this tender moment, which is slightly tainted by the fact he just finished fucking the soul out of your girlfriend.
Rick: "I know, isn't it great? She's an amazing woman, and you're an amazing nephew. We go great together, and you obviously enjoyed yourself too, despite the unfortunate abstinence."
You can't help but think he might be right, was there a part of you that always wanted to see them together? To see Rick invade Jen's pussy with his monster cock? No....but why did you agree to send Rick those pictures in the first place?
Wasn't it to brag? Maybe it was bragging at first, but you also wanted to impress Rick. Make him jealous of your smoking hot girlfriend. Mission accomplished there, at least.
You: "I just.....don't know where to take it from here...."
Rick squeezes you in a little harder. His body is so warm.
Rick: "Hey man, don't worry, the first time is always a little awkward, the next few times will be way better. And after a while, it will stop being weird altogether. Don't worry about having to jerk off all the time, since you can't have sex with Jennifer. I think I have an old flesh light for you here somewhere you can use instead of Jen, okay?"
You: "Next...time....? No, this was a one time thing, ok?" You say with slightly more steel in your voice than you expected. Rick moves away from your weird, naked hug, leaving a slight sheen of his sweat on you.
Rick: "Hmm....I don't know about that, Jake. Jennifer and I are ridiculously sexually compatible, you saw it. It's something I've never experienced before in my 45 years of age. Our bodies fit together like two puzzle pieces. The attraction we have towards each other, is like gravity, it's unavoidable."
You: "I just want to forget about this night, ok? This never happened."
Rick: "Oh, it happened, alright." He chuckles, and continues: "Listen nephew, I'll give you some advice."
You: "....what?"
Rick: "Statistically, a high percentage of young couples, like the two of you, break up within the first two years of the relationship. The reasons could be multiple, but one stands out; cheating."
You: "Like what happened tonight?" You ask, angrily...
Rick: "No, nothing like that. What we just did was completely consensual, it wasn't cheating. Remember, you agreed to everything every step of the way."
You: "But..."
Rick: "And that's a good thing! The reason most women cheat on their partners, is that they're sexually repressed. So many relationships could be saved with a simple...release, like tonight."
You: "I...I don't think our relationship is in trouble."
Rick: "Few people ever realize that in time. While we were texting, Jennifer told me how she has been holding herself back from experimenting, sexually. This is a huge risk for you, nephew. You never know when she has enough and....cheats on you." Rick puts his hand on your shoulder again.
You: "This is so fucked up, Uncle Rick...." you sob slightly, and Rick starts hugging you again. You can hear the shower running now, Jen must have used the toilet first.
Rick: "Listen, buddy. What's fucked up is that society has programmed you to believe Jennifer should restrict herself to one man for the rest of her life. It's not fair to her, and it's not fair to you. Give it a couple of years, and Jennifer's curiosity will have gotten the better of her, and she'll start seeking sexual pleasures outside of your relationship. You don't want that, do you? To lose Jennifer?"
You: "...no..."
Rick: "You love her, right? I heard you say it before...."
You: "Yes..."
Rick: "Then I'll help you. Just let Jennifer explore her new self on this trip. And who knows? Maybe she's had enough after tonight.
You: "...yeah maybe...."
Rick: "But if she hasn't....you should share your girlfriend with me. It's a big change, and change is hard, but I promise it's going to be fun. Okay?"
With Rick's big body surrounding you in this weird, sweaty, naked hug; and his logic being seemingly infallible at the time, you feel trapped, backed into a corner. According to what he's saying, you say yes now, or you eventually lose Jennifer.
The choice seems obvious, but one choice leads to Rick fucking Jen again, and the other leads to her fucking some stranger. As fucked up as it is, you'd rather see Jen fucking Rick than her cheating on you with just some college frat dude.
You: "....I´ll think about it, Uncle Rick."
Rick: "That's a good boy...good choice."
He strokes your hair lovingly, giving you some fatherly affection you didn't know you appreciated. Despite realizing the depravity of the situation, your naked uncle, who just finished ejaculating inside your girlfriend, coaxing you to allow him to do it again, you hug him back harder, which, given his size, presses his cock up against your stomach.
At least Rick's a good guy. And this will let Jennifer release her....tension. You think, trying to convince yourself this is a good idea.
What's next?
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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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