[Group] Family vacation leads to sex with another couple

This is the story of how my wife and I fucked another couple on our family vacation. A great time was had by all and we’ll definitely remember this vacation for years to come. I may not mention it in the flow of the story, but condoms were worm for all PIV sex. And, because I’m still working on my writing and don’t know how to fit it in later, here’s a description of my wife and I. Jessica is nearing 40 years old, 5’3”, 170lbs, long curly blond hair, green eyes, soft white skin, plump ass and thighs, perky C cups, and she absolutely loves pleasing men. I’m Jack, a 42 year old white male, 6’4”, 230lbs, muscular though no six-pack, brown eyes, brown hair, above average endowment and I love to please women. Lastly, there’s some long setup so bare with me, it does get very interesting.

It was the sixth day of a nine day family vacation with our two kids and we were both of pretty revved up. Up until this point, we were enjoying all eye candy from afar and fucking every chance we could get: thank god for the kid’s club…lol. Honestly, finding other people to play with was always on our minds but we weren’t really putting ourselves out there as we knew we’d be at the resort among the same people and didn’t want to risk causing an issue. That would all change without us really expecting it.

It was early afternoon, just after lunch, and we were enjoying the pool with our kids. The lounge chairs we were relaxing in were on a shallow shelf in the pool in about ten inches of water. This will be important later. The kids were both off splashing and playing around when a Filipino family sets up in the lounge chairs next to us. They smiled and said hi as they were setting up, laying out their towels, and slipping out of their cover ups. I was stealing glances at the wife as much as I could without getting caught. She was a smaller BBW, about 5’3”, short brown hair, brown eyes, and though she was wearing a one piece bathing suit, it perfectly showed off her ample chest and plump ass. The husband was fairly fit, probably 5’8”, and definitely caught my wife’s attention when he removed his shirt. The four of them slid into the pool and went off playing around together. My wife and I exchanged looks and smiled, knowing exactly what each other was thinking. Soon enough, the husband and wife return, he taking one of the lounge chairs closer to us and her staying in the water, but up on the shelf, propping herself up on the the further lounge chair. I saw all this out of the corner of my eye and was looking for a chance to look over in their direction and when I finally did, holy shit was I not disappointed. The way she was leaning forward, talking to her husband, allowed for the perfect view of her huge breasts spilling out of her bathing suit. I mean her cleavage was fucking spectacular and I guess I must have been staring for quite awhile because when I looked up, she was staring right back at me. I quickly turn my attention to the pool, not sure what to do but still watching out of the corner of my eye as the wife is saying something to her husband that is too low to hear, and then some movement from her. My wife nudges my elbow and tells me “smooth one, doofus” and we both kind of chuckle but I can’t help but want to look over again. When it seems the husband and wife have turned their attention to their kids, yelling out for them to be careful, I quickly look over, sure it was safe to do so. God damn was I glad I did. The wife was still leaning forward, her arms propping her up on the lounge chair, and also framing her breasts so that others couldn’t get the same view I had, but it seemed she somehow managed to lower her swimsuit even more, her dark arreola making an appearance this time. I look up from her breasts and this time, she’s got a huge beautiful smile. Now the four of us all kind of looked at each other before the husband breaks the ice, introducing themselves. “Hi,” he says, “I’m Edwin, and this is Marie.” “Hello,” I reply, “this is Jessica and I’m Jack.” Edwin starts some small talk, talking about where we’re all from, how long we’re there, etc and then I get sarcastically confronted about liking the view. My heart sank for a moment but he quickly let on that they knew what they were doing and wanted to gauge our reaction. We all have a chuckle and Edwin tells us that based on both of our reactions, they figured we might be in the lifestyle. From that point, the discussion is focused on the lifestyle, as much as it can be with kids and other people all around but before we knew it, we’re setting up some play time before dinner. At that point, we all go our separate ways, agreeing to meet in one hour.

We tell the kids it’s time to go, not without some protesting, but explain they’re going to kid’s club and makeup something about us going to wine tasting. They ask if they’re new friends can go, having befriended the our new friend’s kids and we let them know that as a matter of fact, yes, they’ll be going as well because we’ll be doing the wine tasting with their parents. Jessica heads back to room to take a shower and I rush them over to kid’s club. When I return to the room, I find Jessica shaving in shower. I attempt to join, wanting her right there, but she says we should hurry and get ready so we don’t eat into our time with our new friends. I reluctantly agree and we finish getting ready. Jessica wears a small white summer dress, white heel sandals, with no bra or panties, the perfect resort attire. Nothing special for me, just a blue button down, grey shorts, and nice pair of flips flops.

We arrive at their room and they invite us in. Right away, Edwin is complementing Jessica on her dress and I do the same for Marie. She is wearing a black babydoll dress which is fairly low cut, perfectly framing her breasts and showing an ample amount of that cleavage that I’ve come to love, while complimenting the rest of her body perfectly. They have the same room as us, two double beds separated by a small table, keeping them about 3 feet apart. Edwin offers us drinks from the fully stocked mini-fridge and we all place our orders. There’s not much for seating, so Edwin guides us to between the beds, ladies first, sitting opposite each other and the guys next but Edwin takes a seat next to Jessica and I sit next to Marie. There’s the usual awkwardness so I decide to break the ice, asking two questions; what’s your favorite thing about sex and least favorite thing? I tell Edwin to go first and we’ll circle around clockwise. Edwin says that one of his favorite things are wet, sloppy blowjobs and his least fovorite is teeth during blowjobs. We all laugh and then it’s Jessica’s turn. She says that Edwin is in luck because her favorite thing is giving blowjobs, to which we all have a laugh again. She continues saying that her least favorite thing is when men don’t ask if the backdoor is open before trying to enter it. Agreeing nods all around and we all take sips from our drinks. Marie gets into how she loves to straddle a man’s face while he services her and she despises when men just assume they can cum wherever they want. I exclaim ‘duly noted’ before getting into how contrary to my earlier reaction to Marie’s amazing breasts, I’m actually an ass man and I absolutely love playing with a woman while she’s face down ass up and going along with Edwin, I’m definitely not a fan of teeth during blowjobs. Another round of laughter from the four of us.

Not wanting the momentum to die down, I reach across Marie to put my drink down on the table, being sure to brush against her ample chest. I pause while leaning across her and we’re soon embracing in our first kiss before making out like a couple of teenagers. Edwin takes this cue and goes for a kiss as well and soon enough, they’re making out, his hands running up her naked thigh. While exploring Marie’s mouth, my hands go right for her breasts, squeezing them through her dress, more impressed by their size. We all make out for from quite some time, my hands all over Marie’s body. I start feeling her legs under her dress, slowly rubbing up her thighs, about to reach to reach their final destination when she stops them and whispers to me. I do as she says and lay on my back, across the bed so my head is closer to the gap between the two beds. Marie promptly climbs on top of me, facing Edwin and my wife, and straddles my face, hiding it with her dress. There’s just enough light to see her beautifully shaved pussy. I start to tease her, licking and kissing her thighs, kissing her outer lips, while my hands cup her ass. Having enough teasing, she lowers herself, forcing my mouth onto her pussy. I hear Edwin and my wife ask Marie to her lift her dress nearly in unison and she pulls it up and over her head, completely removing it. Looking up, I get a beautiful view of her tummy and the underside of her breasts. They laughingly thank Marie and asks us to continue. Marie spreads her legs further, smothering my face with her sopping wet pussy and starts vigorously grinding on my face, Rocking her hips, she grinds back and forth, using my whole face, rubbing her cunt from my chin to mouth to nose, and back. I think she surprised all of us when she moved her ass to my mouth, grinding it into my mouth as well. Marie’s moans start getting louder and she returns her pussy to my face, and just lets go, fucking my face vigorously and in no time, she begins to cum. As Marie starts to come down from her orgasm, Edwin and my wife applause and we all laugh.

I hear Jessica excuse herself for a second and I strain to turn my head and watch her head towards the restroom. She quickly returns with a towel and then proceeds to undress Edwin before asking him to sit on the towel. He pauses and asks Jessica to remove her dress and she quickly pulls it off, revealing her naked body, much to Edwin’s pleasure. I’m the only dressed at this point but Marie quickly takes care of that, pulling my clothes off me. Jessica then has Edwin lay back and she takes her place between his legs, taking his stiff cock in her hands before lowering her mouth onto him. Marie gets comfortable, laying on her side to watch my wife please her husband and I snuggle up right behind her, pressing my hard cock against her ass while my hands reach around and fondle her breasts and tummy while we watch the show. Fully aware of Edwin’s early statement about his favorite thing, Jessica works Edwin’s cock like a pro, saliva and pre-cum dripping from her mouth with each thrust of his cock into her mouth. Every so often, she pulls away and a string of gooey mess connects the tip of his cock to her tongue. She continues her assault on his dick, taking it as deep down her throat as she can, in and out, in and out. Not forgetting his balls either, she goes down and take them in her mouth, rolling them around, licking them, sucking them, using her hands to cup them into her mouth. Watching from behind Marie, I start wondering how in the world Edwin is not exploding in my wife’s mouth. “Damn Edwin, I can’t believe you haven’t let go yet.” We all chuckle and Marie tells us how Edwin has the most incredible stamina. Sometimes not even needing to come. Wow, is all I can say and Jessica continues working his cock.

Marie then turns towards me, our bodies facing each other and pressed together. Her beautiful tits pressed against my chest, our tummies touching, our legs intertwined and we go for another make out session. Our tongues dance together wonderfully and she tastes so fucking good. I reach behind her and grab her ass pulling her in tight to me and I can feel her starting to get worked up again. She breaks away from our kiss and asks if I’d like to play with her ass. I’m no fucking idiot, so I tell her hell yeah. She gets up on her hands and knees and lowers her head to the bed, arching her back, presenting that gloriously plump ass to me. Grabbing both her cheeks I spread her wide and go in and lick of her puckered asshole. I lick and suck, lick and suck, while my hands makes their way from her ass to her fiery cunt. I work my thumb in a circular motion on her inner lips before plunging it deep inside of her, fucking her wet pussy, in and out, in and out while eating her ass. Marie bucks her hips back against my mouth and I continue sucking her ass and fingering her pussy with my thumb. I nearly can’t take it anymore and I decided I’ve got to get inside of her. I grab a condom out of my shorts on the floor, roll it on my dick, and take my place back behind her. Grabbing onto her wide hips, I line my dick up to her love hole and press inside of her. Marie lets out a moan as her pussy takes every inch of my cock until I’m pressed into her as far as possible. I then slowly start to build up a rhythm, fucking her in and out, in and out while keeping a firm grasp of her hips The view I’m getting is incredible, seeing her wide ass swallow my dick, time after time. I look over and it seems we have an audience, Edwin and my wife watching me plowing Marie from behind.
This must have got Jessica really worked up because before I knew it she was on her back, legs spread, asking Edwin to have her way with her. He rushed for a condom, slipped it on and took his place between her legs before plunging into her with sopping wet pussy. She pulled her legs back and wrap them around his waist as he took what he wanted. He was soon fucking her with no abandon, just as I was fucking his wife. It was definitely one of the hotter moments. All this intensity, fucking this hot woman while watching my wife taking Edwin’s cock, had me right at the edge and I pretty much couldn’t last any longer. I took a few deep thrusts, deeper than any before. And started nutting into the condom.

I pulled out of Marie and lay on the bed exhausted, Marie doing the same, both of us laying naked watching Edwin fuck my wife. Jessica’s moans got louder and louder and though I knew she probably wouldn’t be coming from this position I could tell that she was very close. She also knew this, apparently, and told Edwin to let her get on top of him. There certainly were no protests from him and he pulled out and laid on his back across the bed, his legs hanging off the bed. Jessica stood in front of Edwin, facing Marie and I and lowers herself onto his cock, grinding her ass into his lap. She locks eye with me as she slowly raises her hips up and down, up and down. She slowly picks up the pace, never losing eye contact, her ass slapping down onto his lap. The look in her eyes says she getting close and she soon turns around facing him, giving Marie and I a view of her beautiful ass. Taking him back inside her, Edwin grabs her ass, spreading her wide as she starts to grind her clit on him. Marie notices my cock hardening again and slowly strokes me as we watch them go it. It doesn’t take long for Jessica to start cumming and she tenses on Edwin’s cock when her orgasm hits her. Edwin gives her some time to come down from her orgasm before he starts fucking her from the bottom, thrusting his hips into her repeatedly. Apparently, Jessica cumming while fucking him was enough to get him to the edge because he yells out he’s getting close. Jessica jumps up and tells him to cum on her tits as she gets down on her knees. Edwin quickly positions himself in front of her and Jessica jerks his cock to completion and he does not disappoint, spraying a huge load all over her tits, chest, and some on her neck. It was our turn to applaud and we had another chuckle.

We all got up and got cleaned up before heading back to the beds, Edwin snuggling up with Jessica and I with Marie. We made some more small talk, discussing how hot everything was that just happened, while we stroked and rubbed our respective partners. Noticing that I was hard again ever since watching Edwin and my wife go at it, Jessica asks Marie if she could help her blow me, as she knows it’s right up there with my love of ass. Marie enthusiastically accepts her invitation and Jessica joins us on the bed. Jessica gets down between my legs and Marie lays beside me, her pussy towards my head. Jessica immediately goes to work licking and suck my balls while Maries takes the head of my cock in her mouth, teasing with her tongue and lips, before taking me as deep as she could. While the two girls work my cock, I play with Marie’s pussy and Edwin stays on other bed and watches, admitting that it takes him a while before he’s ready to go again and that he’d love to just enjoy the show for now. Both girls are working my cock big time, alternating between my balls and tip. It was definitely one of the hotter events of the day for me and it took everything I had not to come again. Nearing that point, I decide to change things up.I tell Jessica she needs to come again. I get her on her back and dive into her pussy, licking and sucking and fingering while Marie moves in and kisses her and plays with her breasts. It was incredibly sexy looking up from my wife’s pussy, watching this voluptuous woman kissing and playing with her. It doesn’t take long before she starts cumming, her body tensing as she lets a series of loud moans. Jessica needs a breather so she moves over to the bed with Edwin and they snuggle up just as Marie and I before.

As Jessica and Edwin laid there, Edwin asked Marie if she would put on a show for the two of them. Marie eagerly obliges and she has me lay across the bed again, my legs hanging off the edge in the space between the two beds. Marie took her place standing between my legs facing my wife and Edwin. She wiggled and lowered her ass towards my hard hardening cock and began to grind in my lap, my precum giving just enough lube for my cock to easily slide between her ass cheeks.. I prop myself up on my elbows and watched my dick slide between her ass cheeks, as she grounded into my lap. Soon, she lifted her ass, and reach between her legs to guide the tip of my dick to her hot cunt. As she lowered herself onto me I got the wonderful view of my cock disappearing between her ass cheeks again, my hands made their way to her hips and guided her up and down as she slowly started to bounce on top of me.

Just as Jessica early did to Edwin, Marie turns around to face me, mounts me, and my hands immediately find her plump ass, spreading them for all to see. Jessica and Edwin voice their approval and Marie moans in her ear. Jessica exclaimed this must be doing something for Edwin judging by his hardening cock. Despite that, I hear him exclaim he wants to taste her beautiful pussy. She moans her approval and judging by her moans, she got really into it. Marie continues working me, grinding her clit against my pubic mound. I can tells she’s getting close and soon she comes again. I can also hear Jessica getting really into things, Edwin apparently really knows what he’s doing but we should’ve guessed that when Marie exclaimed how having her pussy licked was one of her favorite things. Jessica is soon coming herself, for the third time, and impressively, quicker than with me.

After a while, Marie rolls off me and I mount her missionary, finding that she’s rather flexible, as her feet nearly reach her ears. Apparently enjoying what he sees, Edwin does the same to Jessica, though she’s not nearly as flexible, but still spreads wide. All four of us are now in our own little worlds, purely focused on the person we’re with. I kiss Marie while fucking her, her pussy squeezing my hard cock so well. Moans and sounds of sex fill the room, both guys clearly going for the gold, subconsciously aware that things will need to end soon. I nuzzle and kiss Maries neck, her mouth nibbling my neck and ear. She can tell I’m getting close and she tells me she wants my cum all over her face. That does it and I quickly jump off her and straddled her stomach. She strokes my cock and it doesn’t take long for me to spray her tits, with a few ropes making it up to her face.

Coming down, I relax next to Marie again while watching my wife, it obviously taking Edwin much longer, he’s fucking Jessica for all he’s worth. He must have pounded my wife’s cunt steadily for at least ten minutes but we could tell it wasn’t going to happen for him. Satisfied that Jessica got all the pleasure she can, he rolls off her. Marie reassures us that all is good, that it’s not uncommon for him not to be able to come a second time so no worries. Jessica and I were completely fine with it and let them know that there are definitely some pluses to having a guy with such lasting power.

We all take a few minutes to clean up before making plans for the next day, which was a whole different kind of excitement.

Source: reddit.com/r/gonewildstories/comments/6m5uqa/group_family_vacation_leads_to_sex_with_another