Vacation in Mexico years back. My wife, myself, my best friend and her best friend. We'd been drinking all afternoon. And multiple drinking games had turned into truth or dare which turned into just dare. Started off innocent enough. Our room was about four stories up and we had a balcony overlooking a pool and a bar. The bar was pretty full. Maybe fifteen people. It was about 8pm. I started a string of dares by making my buddy stuff a pillow up his shirt and go down to the pool/bar area and scream "hello everyone!" We all watched him do it from the balcony. Again. It was stupid. But fun when you've been drinking and you're in your 20s. We all dared each other to do similar things and my mind starts turning trying to find a way to spice things up. I can't just dare my wife's friend to do something sexual or my wife will kill me so I try to start the ball rolling that way by daring her to do something. I tell my wife she has to take the elevator down bottomless. No pants. She's like "like bikini bottoms?" And I'm like "nope." Kinda thinking she'll say fuck off and I'll have to come up with something else. But she's considering it. So I say she can obviously pull her shirt down and it's not that big of a deal. So she agrees. The full dare is to go out by the pool, so like fifty feet from the bar area and pull her shirt up and expose her butt and smack it then come back up. She agrees. My wife is curvy. Not fat. Big round ass. So she goes to the front door and takes her shorts and bikini bottoms off and tugs down her tank top and exits. I look through he eyehole in the door and see her hustling to the elevator. Pulling her shirt down, but her butt is so round and the shirt isn't very long. Her sweet ass cheeks are fully visible. So we hit the balcony to watch it go down. We finally see her head towards the pool. She gets to the edge, and turns away from the bar. She yells "hey everyone" and lifts it up and smacks her ass cheeks a few times. The bar erupts with cheers and laughter and she runs back into the hotel. I'm stoked. My buddy is checking out my wife's ass. Which is hot. And I feel like I've opened the game up for some fun stuff. The next dare is for my buddy to do the same thing. Yawn. Man ass. No thanks. Then he gets back up and dares my wife's friend to do it. I'm trying to hide it but I'm so stoked. My wife's friend is pretty hot. Thin, small tits but thick in the ass and thighs. So she strips to her top only and I'm trying to see as much as I can without my wife thinking anything of it. She runs to the pool and does it. Same applause and laughter. The people down at the pool bar are all onto us now. They just keep waiting for the next dare. Her friend gets back to the room and dresses. She dares me to do the same totally naked. I'm a little nervous to do it but I feel like I have to because 1) we've opened up the dares beyond me daring my wife, and 2) if I go fully nude, that's the new bar. So I strip. I don't even try to hide anything. I'm drunk and hoping if I'm open they will be too. I take the elevator down and get to the edge of the pool. Everyone is already cheering and laughing. So I'm like fuck it and I jump in the pool. I hop out and start heading back to the hotel. And there's a security guard there. He says something like "hey man, you guys gotta stop. This has to be the the last thing ok?" And I'm standing there naked feeling as awkward as anyone has ever felt.
I get back to the room and put on a robe. I tell them about the security guard. But I don't want the game to die. We have plenty of beer so I suggest we head to the beach. So we do. The first dare after we get there was super tame so I know I have to up the ante again. I dare my friend and my wife's friend to wade into the water at waist high and exchange his trunks with her bikini bottoms. They do. Then immediately dare me and my wife to do the same. We do. So we're on the beach and both us guys are wearing bikini bottoms and nothing else. My buddy says we gotta get back into our trunks so we agree to exchange back. Reservations have lifted at this point. We all just trade swimsuits back. My wife pulls my trunks off so she's wearing nothing but a bikini top. Her pussy is fully shaved and fully visible. And it's dark enough that I'm just sneaking peeks at her friends pussy. Also shaved. Luckily I'm wet and cold so yeah, I'm naked but my dick didn't get hard.
So I'm horny as fuck. Brain working hard to find ways to keep this going. I dare my wife to close her eyes and touch all of our asses and guess who's ass is who's. So my buddy, her friend and myself have our trunks and her Bottoms around our knees and my wife one at a time comes behind us and cups our ass cheeks. She's got a t shirt over her head so she can't see so I'm just standing there watching her grope my buddy's ass and better yet, her friends ass. She of course was able to guess. It's pretty obvious haha. In my head I'm like "please return the dare! Do it do it do it!" And she does. Passes it onto her friend. So we all do it again. Her friend grabs my ass and doesn't just grip it real quick but squeezes it and kind of cups it and runs her hands under. She's into it. I think. Then she squeezes my wife's thick ass and my buddy is just staring. Then they dare us guys to do it. So I have to touch my buddy's hairy ass but I get to grip and squeeze my wife's friend's ass. I'm blindfolded but I can tell it's not my wife's. So I grab it and squeeze it run my fingers under the cheeks fighting every urge to slide my fingers under and touch her pussy. Then my buddy goes and that's cool too. He's gripping my wife's ass and she seems to dig it.
So we keep playing. Mostly just daring each other to run to the water and jump in naked and goofy stuff like that. I'm racking my brain to find a way to up the ante but we kind of peaked there. And the beer was hitting us. We went back to the room and I tried to keep it going. But my wife was too busy daring things to try to get our friends to hook up. Like kiss each other. Sit on each other's lap. Etc. The night winded down and we crashed. But every time we see her friend I think about how her ass felt in my hands. And I have all this regret because I wanted to dare my wife to touch our dicks and guess who's was who's. Gotta play your cards right in those moments.
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