***warning this is a long one full of steamy details***
Back when i was 24 my long time bff “Molly” and her fiancé “Brad” got a pool suite at a fancy “couples only” hotel and invited me and my long time bf Keith to sneak over to party and hang out in the pool with them.
Ill set the scene for you, Molly is 23, 5’3, like 180 lbs of volleyball and softball toned thick, wearing a skimpy blue 2 piece bikini showing off all her sexy athletic curves, 36 C tits and nice round ass. Her fiancé Brad is 29, 6’2 around 200 lbs of fairly athletic build, wearing his red surfer trunks. My bf Keith is 5’8 like 210 more on the “dad bod” side even tho he was only 26, wearing dark blue trunks. I was 24 at the time, 5’5 around 190 lbs, also softball toned and thick as well, with 38 DDD’s busting out of my purple bikini top.
After playing some marco polo in the fairly large private pool that was like 5 feet deep, we all hopped over in to the connected hot tub to throw back a few of the margaritas that we had mixed in a giant thermos prior to showing up. After getting a lil tipsy on fairly potent margarita’s, Molly suggests a game of couples truth or dare. So we hop back into the larger pool, and start with a few truth’s(could tell both couples were hesitant to “get crazy” with any dares). Finally my now drunk bf says “i dare you to show us who has bigger boobs”…i look at Molly smiled and she smiled back(we had seen each other naked plenty of times over the yrs so this was no big deal for us…plus i already knew mine were bigger and so did Keith, he just wanted to finally get a good look at Molly’s tits the lil hound)
So Molly and I swam next to each other and then quickly we yanked each others tops off. Both our giant tits flopping out and floating nicely on top of the water for our men to see. I immediately noticed both Keith and Brad now trying to hide what they got going on in their trunks after seeing the titty bonanza. We each playfully grab each others boobs and Molly says, well i think we can see who won this one. The two just awkwardly but confidentially express agreement, with Brad saying dam Keith she has a great giant rack, you’re a lucky guy.
We go to put our tops back on, and the guys joke and say there is no need for those. Molly and i look at each other and quickly agree to leave them off. At this point the margarita buzz must be really kicking in for all 4 of us, bc we are topless floating around in front of each others bf/fiancé and dont seem to care one bit. After watching the guys continue to hide whats clearly two raging boners in their trunks, i have the idea to say, “now its your turn fella’s, lets see who is bigger”…you can tell they were both stunned, not expecting that i guess. I looked at Molly and she was laughing egging them on saying lets go boys, dont be shy now.
After a few mins of back and forth listening to both of them try and riggle out of it, they both agree to it. They are on opposite sides of the pool from each other and me and molly are floating in the middle of the pool ,4 giant tits still floating on the water, i notice both our nipples were rock hard too. I also quickly noticed maybe by coincidence maybe not, but i couldnt help but fixate my attention on Brad as i noticed Molly was staring at Keith too. They started to count down from 5, 4, 3, 2, 1…and boom, both yanked off their trunks and tossed them aside.
I instantly noticed how big and thick Brad was(probably close to 8’ and thick like a water bottle) he was already rock hard with a giant mushroom head that looked so delicious, i was immediately jealous of Molly. I looked back and saw Molly staring intently at Keith who was also rock hard(a lot smaller at like 5 1/2’ but very thick like a shampoo bottle) i was surprised despite his lack of measuring up to Brad he stood there confident and proud of what he had, i give him credit for that and it really turned me on seeing his confidence even as he can clearly see he isnt in the same league as Brad. Molly reeling from her titty defeat apparently rapidly points out Brad is the clear winner. But throws in but Keith looks like he wins the thickness part of the competition, which i could tell made him feel good to hear from somebody other than me compliment his cock.
Brad then says, “ ok now that we are all naked, what now”. I couldnt tell what was about yo happen but i decided to roll with it and glanced over at Keith and he gave me the reassuring “im good too” look. I look at Molly and she gives me the nod of approval with things too. We start to grope each other’s tits now, playfully rubbing our nipples together while giggling in our inebriated state(not the first time we have touched each others tits over the yrs)
I look over and both Keith and Brad are standing on opposite ends of the pool watching us while stroking their cocks slowly. Molly signals for them to come join us in the center of the pool, and they both quickly walk over, rock hard cocks still firmly in hand as they approach, we turn our attention from our tit groping and each start kissing and making out with our men. I tell them to both sit on the edge of the hot tub and they both hop up on the edge, two delicious cocks on full display, so Molly and i swim over between our mens legs and we both start sucking or mens cocks. Molly quickly shows off by going all the way down balls deep on Brad’s huge cock over and over as he pushes her head down making her gag. Not to be out done i start furiously deep throating Keith’s super thick cock til i find myself gagging on it bc of how turned on he is apparently. After like 4-5 mins of both of us going to town on our mens manhood with our mouths, i look at Molly and i already see in her eyes what she is thinking. So she jokingly says “switch”, and i immediately look at Keith to see his reaction, but i can already tell the drunken horn dog can only think about having his gf’s long time bff sucking his cock, not thinking about the flip side of that coin obviously.
So with one of our hands each, Molly reaches out and grabs Keith’s cock as i reach out and grab Brad’s. So each of us now have one hand on our mans and the other hand on the others cocks. We start playfully stroking each other’s mans cock together for like a min. Both guys appear to be in total ecstasy. Getting what amounts to double hand jobs from us. The amount of intense throbbing reverberating up both of their shafts to two nice round pink mushroom heads was a slutty site for the ages and made me so wet. Molly and I had played around before but nothing ever as intense as what this had escalated into. Before you knew it i was stroking Brad with both hands all by myself as Molly was doing the same for Keith.
And maybe it was the tequila, or maybe it was the cant pass up the opportunity of having such a glorious giant cock in my hands, i took the risk that Molly would mind if I crossed over to the next level of sluttiness and started full throating Brad’s 8’ cock over and over again, it felt so amazing hitting the back of my throat almost making me gag each time while rubbing his balls with my hand. Next thing you know i look over and Molly had Keith fucking her face while he reached down and groped her fat perky tits. It was at this point that i realized all bets were off. It was a lil bit jealousy maybe of seeing Keith enjoying Molly the way he was, and how turned on i was having Brad’s monster dick in my throat, but made the move to pull Brad into the hot tub as i hopped up on the edge now, bikini bottom still on but dripping wet pussy right in his face behind it. He swiftly yanked my bottoms to the side and and buried his face and tongue deep in my pussy, i let out a loud moan, breaking Keith and Mollys’s attention of her slowly going up and down on his fat cock.
It was then that Molly hopped up on the edge of the pool and took off her bikini bottoms as Keith swam over and also began diving into her tight freshly waxed pussy while reaching up and continuing to grope her tits and nipples, she then let out an equally hot moan which just made Brad start to eat my pussy like he was getting paid for it, and i began to press his face against my clit as he licked like a maniac, it felt sooooooo good as he was now also firmly playing with my tits and nipples. Between that and seeing my man’s face buried in my best friends snatch right across the pool from me was a thrill like i cant even describe.
But now i couldnt help but think about how badly i wanted to feel Brads enormous hammer inside me, but i wasnt sure in my drunken state if this was a final step that required some conversation about between Molly and myself or maybe Keith and me should at least come to an agreement on taking it any further than we already stunningly had.
But him and Molly appeared in there own lil world on the other side of the pool with his face still planted between her legs as she moaned like crazy(keith was really good at using his mouth), so i decided to be the aggressor with Brad, i pulled his head up out of my pussy and reached down for his cock and guided it towards my pulsating soaked pussy. I teased my clit with his giant mushroom head tip rubbing all over my pussy as i stroked it for him, i could tell he really liked how it felt, after like 2 mins of letting me tease myself with his cock, he grabbed it out if my hand and rammed it all the way balls deep into my cervix. It hurt so much but in an amazing type of way. I let out a loud gasp and leaned in and he said “i hope you’re ready im about to rock your world”, he then began to slowly but forcefully pull all the way out and then slide all the way in over and over and over. I literally never had a cock that big before(except one other guy)and it felt even better than i imagined it would.
As Brad pounds the bejesus out of my tight unprepared pussy, i notice Keith and Molly have moved to the bed now, and Molly is riding him while smothering him with her tits, its such a turn on for me to see my man and my bff getting it on while i have a telephone pole sized cock inside me tearing up my guts. I take advantage of the distance as Keith cant hear me now and the alcohol fueling my lust, and i tell Brad he is so much bigger and better than Keith and i want him to make me his lil fuckdoll. He spins me around and forces me against the ladder to climb out of the pool and starts fucking me from behind while smacking my ass and making it echo across the entire suite and pulling my hair firmly too.
I look over and Keith is now jackhammering molly on the edge of the bed like a lunatic, she is moaning so loudly now. I can tell it is fueling Brad’s pace as he starts to go even deeper and harder into me as my tits flop off the top of the water splashing everywhere. I hear Keith say he is about to cum and Molly tells him to shoot it on her tits, as she is sprawled on her back on the bed, i see Keith jerking his cock so hard and fast until he blasts the hugest load i think id ever seen him have all over Molly’s tits and splashes in her face, she starts cleaning him up by sucking the cum off his cock for him.
I can tell Brad is on the brink of cumming now too after witnessing Molly getting sprayed with Keith’s cum shower. He asks if he can cum in my mouth, i tell him sure, as i can barely speak he is pounding me so hard from behind for what seems like 15 mins straight now, but before we can settle on where he is gonna cum, i feel his third leg size cock getting even firmer and starting to quiver a bit so i can tell he is about to blow, so lean back into it and force him as deep inside me as he can get and i feel him unload his warm pool of cum as it floods my entire pussy, he keeps thrusting into me for at least 2 mins after he cums while firmly groping my nipples. And then slides himself out and i feel his load spill out of me into the pool as i climb up the ladder.
I look over and Keith is on the bed now, Molly had come back by the pool to witness first hand up close her man’s triumphant pussy smashing. And she hops back into the pool and starts kissing Brad, so i head to the bedroom to make sure everything with Keith is good. I see he is still stroking his semi hard cock and He pulls me on top of him and forces his cock inside my pussy still lubed up and dripping with Brads cum. I begin to bounce up and down on him faster and harder than i think i had ever done. I was trying to get his cock to go as deep as Brad’s was but i quickly realized it wasnt gonna happen so i allowed myself to just enjoy the pounding from my man as my pussy still throbbed from being destroyed by a superior cock. And it wasnt long before i felt him grip on to my hips and force himself as deep as he was capable of as he unloaded his seed in my pussy now, it felt so warm and relaxing.
At the same time Brad had been letting Molly bounce up and down on his chiseled baseball bat til she was also cumming louder than i had thought possible(made me regret not getting on top and feeling what that felt like to ride for a while), Molly then hopped off and started stroking Brad a million mile a minute until he shot his second load up in the air like a geyser and Molly went down and licked up every last drop.
It was one of the hottest nights of my sexual life and i was glad to share it with my bff. Molly and I never really spoke about that night, but im sure she enjoyed as much as i did, and maybe even as much as Keith did
Source: reddit.com/r/gonewildstories/comments/uxaoh3/two_bffs_and_their_so_others_have_fun_in_a_hotel