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Author Topic: Sydney's Extreme Threesome (A Sydney Sweeney story)  (Read 9566 times)

Cptnstrwrs

Sydney's Extreme Threesome (A Sydney Sweeney story)
« on: October 31, 2025, 12:09:02 AM »

Los Angeles, California 


        I couldn't believe I finally had a day to myself. Between work, wedding planning, and all the other normal life stuff, I could just relax and take it easy. Ariana and Demi Rose were out doing who knew what, so it was just Sydney and I in the house. Normally, I'd be excited for any one on one time I can get with her. I mean, who wouldn't love to spend a day with Sydney Sweeney? But lately, Sydney hadn't been herself, like something was bothering her. At first, I thought it would be better to wait until she was ready to talk about what was bothering her, but after a few days, I decided to step in. "Hey Sydney, Baby. Are you ok? You've seemed a little off lately," I ask her softly. "Are you seriously asking me that!? Of course you wouldn't notice! You've been too busy wedding planning and fucking other women in front of Ariana to pay any attention to me!" Sydney exclaims, her eyes filling with tears. I feel horrible, mostly because she's right. I've been so busy lately that I haven't had as much time for her or Demi Rose. I know I need to make it up to her and I know just the way. "You're right. I'm sorry Sydney! Come here!" I say, hugging her tightly, Sydney's enormous tits crushed between our bodies as she lets it all out. I wait until she's stopped crying to tell her my awesome plan.

        "I think we need to make up for lost time, starting right here, right now," I say to her. "What if I invited another guy over to join us? You'd be getting double the attention in half the time!" I say, grinning at her. "Wait. Do you mean the two of you would take turns with me or you'd both fuck me at the same time?" Sydney asks, a hint of nervousness on her face. "I was thinking a little of both. What if I invite the Extreme One over to join us as the other guy?" I ask. Any of her previous nervousness melts away. "That sounds incredible! Call him right now!" Sydney exclaims, grinning at me. I make the call, and almost an hour later, the Extreme One is ringing the doorbell. "Hey man. Good to see you again!" I say, letting him in. "Thanks for inviting. Although I'm not sure how anyone could say no to this!" Extreme laughs as we shake hands. "This is Sydney," I say, stepping aside so Extreme can get a good look at her. "Hi. You can call me the Extreme One," Extreme says, shaking her hand. "Nice to meet you!" Sydney says, blushing as she shakes his hand. I can tell she's still nervous, but also turned on at the thought of being fucked by the Extreme One and myself at the same time.

        "How about we get changed and head out to the pool?" I ask. "Sounds good," Extreme says, Sydney nodding in agreement and a huge grin on her face. Several minutes later and the three of us are hanging out in the pool. Sydney decided to go with a light pink bikini and matching bottom. Seeing her in the tiny bikini, you can almost hear the fabric straining to keep her massive tits contained. I can tell Extreme notices it too, judging by the grin he gives me when Sydney swims between the two of us. She swims to the edge of the pool, pulling herself up and out of the water, her tits bouncing in the confines of the bikini top. "You guys mind if I work on my tan for a while?" Sydney asks, walking to one of the patio chairs. "Fine by me," I reply. "Ok. I'll just be a little bit," Sydney giggles, taking off her top, her tits flopping out. She reaches down, untying the string on her bottoms before laying on her back on the chair completely naked. "You know how much I hate tan lines!" Sydney giggles, winking at me and Extreme. 

        The Extreme One and I exchange shocked looks as Sidney just giggles at us. "Oh my God! Do you two need a special invitation or something? Get over here!" Sydney laughs, waving us over. I walk up to Sydney, leaning down so we can make out. Extreme stops near her feet, gently spreading her legs before bending down face first between Sydney's thighs. Of course I don't realize any of this until Sydney pulls away from me, moaning and groaning. "Ugghhh! Oh fuck! He's eating my pussy so good Baby! Ugghhhh!" Sydney whines, writhing in pleasure on the chair. The Extreme One does his thing for several minutes, stopping only once Sydney's close to cumming. He stands up, walking over to Sydney. She sits up kissing him several times before he backs away. He gives me a look and we bend down, Extreme licking, biting and sucking on Sydney's right tit while I do the same with the left one. "Fuck! I love having two guys all to myself! You're making me feel so fucking good!" Sydney moans. "How about you do the same for us now?" I say, grinning down at her.

        Sydney sits up and we close in on her. The Extreme One and I slide our swim trunks down and off, moving our hips towards her. Taking Extreme's cock in her right hand and mine in her left, Sydney begins jerking us off at the same time. Quickly getting us hard, Sydney throws in a blowjob, alternating between sucking off Extreme while jerking me off, then switching to sucking my cock while stroking Extreme's cock. We exchange glances, Extreme giving me a nod. "You're doing great as usual baby. But we're going to need you to get on all fours on the chair here," I say. Sydney quickly gets into position, sticking her ass towards Extreme. I rub my cock across her cheeks and lips before sticking it in her face. "Suck it Sydney!" I growl, giving her a sly smile. She gives me one of her own before she opens her mouth. I slide myself down her throat as Extreme crouches down behind Sydney, licking her clit and  pussy a few more times before standing again. "Mmmmph!" Sydney, still sucking on my cock moans, as Extreme pushes inside her pussy, gripping her hips tightly. The two of us guys quickly get a rhythm going, one of us thrusting into Sydney while the other almost pulls out of her. We pump either end of her like pistons in some kind of sex machine, Sydney moaning and groaning her approval the whole time.

        As incredible as this feels, I know we need to switch positions. "Alright, Sydney. You did great, but now I need you to lie down on your back for us," I say, pulling out of her mouth. Extreme gives her a final couple of thrusts before pulling out of her. Sydney does as she's told, laying down on her back and I climb onto her, aiming my cock towards her pussy. "Hey, Baby. Tilt your head back and open wide for me," Extreme says, Sydney obeying. I push into her pussy as Extreme slides his cock into her mouth, deep throating her as I begin to fuck Sydney's pussy. "Mmmmmm," Sydney moans, once again enjoying having two cocks inside her. We definitely don't fuck her slowly, but at the same time we don't go too hard or fast, wanting Sydney to remember this for a long time. I grab her tits as I fuck her, Sydney's groans of pleasure increasing in volume. As I watch the Extreme One facefuck Sydney I try not to laugh as his balls slap against her forehead after his every thrust. 

        After a few more thrusts, Extreme slips out of Sydney's mouth for a second. "I need more! You call this extreme?!" Sydney exclaims, Extreme and I exchanging grins. He backs away from the chair as I gesture to Sydney to hold on to me. I maneuver our bodies so we end up with Sydney on top of me, my cock still inside her. She immediately starts riding me cowgirl, but I grab her hips, stopping her as Sydney gives me a confused look. "Do you trust me?" I ask her. "Of course I do. You know that Captain," Sydney replies, still confused. "Lean down towards me," I tell her, and she obeys. Reaching back, I grab one of her asscheeks and spread them as Extreme moves into position, Sydney's eyes going wide as she finally realizes what's about to happen. If she's scared, she doesn't show it as Extreme slowly pushes his cock into her ass. "Oh fuck! He's so big! His cock is stretching out my asshole!" Sydney shrieks. "Do you want to stop?" I ask. "Fuck no! Don't stop! Either one of you!" Sydney growls, getting into it. "Ugghhh! Oh yeah! I have two big hard cocks inside me! I fucking love it! Fuck both my holes! Give it to me! Aggghhhh!" Sydney moans as we double penetrate her. "You ever have two cocks before?" Extreme asks, pumping away in Sydney's ass. ""Never! And now I regret not doing this sooner!" Sydney wails. We speed up at the same time, Sydney's cries of pleasure increasing in volume. "Ugghhhh! Fuck! Right there! Don't stop! I'm so close! Ugghhhh!" Sydney shrieks as she starts to cum, pinned in place by Extreme and myself.

        We keep pounding her holes until a minute or two after Sydney finishes cumming. Extreme pulls out of her ass first, then I pull out of her pussy, Sydney groaning with both pleasure and exhaustion. "Uh-uh! Don't get too comfortable, Babe! We're just getting started with you!" I laugh, turning her around so Sydney's back is facing me. I spread her legs, getting Sydney into the reverse cowgirl position as I push my cock up and into her ass. "Ugghhh! It's been too long since you've fucked my ass, Captain!" Sydney moans. "I know. I'm sorry, Baby," I reply. Sydney rubs her clit and pussy, giving Extreme a sexy stare. "Are you just going to stand there and watch? I'm waiting for you!" Sydney purrs, spreading her legs as wide as she can. Extreme walks up, cock in hand, and pushes himself into Sydney. "Oh fuck yeah! Ugghhhh! I've got two dicks inside me again! Agghhh!" Sydney moans as the two of us once again start double fucking her. As I thrust in and out of her ass I realize that I don't fuck Sydney's ass as often as I should. I get so distracted by her tits and her pussy that I all but forget about her ass. I decided right then and there that I won't make that mistake again.   We give it to her hard and fast, Sydney going limp between us, her body overwhelmed by the massive amounts of pleasure flowing through her body. I reach around, grabbing a tit in either hand and squeeze them tightly, Sydney moaning her approval.   We hammer her holes hard for another few moments before Extreme and I both pull out of Sydney.

        The three of us walk into the pool, the water up to Sydney's shoulders while only reaching Extreme and my lower chest. Sydney is facing me so I lean in and kiss her several times before picking her up. I slide her down onto my cock as Extreme comes up behind us, slipping into Sydney's asshole. Once again, we double penetrate Sydney's holes, the water making it a million times easier to slide her up and down our cocks. We're only a few minutes in when Sydney closes her eyes tightly, arching her neck back as she moans loudly, cumming again on our cocks. Extreme and I just keep fucking her until her orgasm subsides, Extreme pulling out of Sydney's ass. I carry her, my cock still inside her, out of the pool and back to the chair. Lifting her up and off my cock, I set her gently on the chair. "Sydney I think it's only right that you let our new friend fuck those big beautiful tits of yours," I say, grinning at her. "The Captain's right, as usual. Come here baby!" Sydney giggles, pushing her tits together. Extreme pushes his cock between her tits with ease, Sydney's body still wet from the pool. They alternate between Sydney rubbing her tits all over Extreme's cock while he stands there, and Sydney holding her tits still while Extreme rubs his cock between them.

        He lasts only a little bit longer than I did the first time I titfucked Sydney. With a grunt, Extreme finally cums, spraying his load all over Sydney's huge tits. She watches, mesmerized as his cum runs down her chest in thin, white trails. While all of this is going on, I'm stroking myself waiting for Extreme to finish. As he steps away from Sydney I feel that familiar aching in my cock. "Come here baby! I'm going to cum all over your pretty little face!" I growl. Sydney closes her eyes, tilting her head up to face me. Within seconds I shoot my load all over her face, covering her in my cum. "So do you feel any better than you did before Baby?" I ask Sydney. "Hell yeah! This more than made up for all the attention I've been wanting lately. In fact, Captain, I think I want to spend as much time as possible with you and your friends going forward. The more the merrier!" Sydney giggles. "We can definitely make that happen Baby! But you know what they say: be careful what you wish for. You did pretty good with two cocks today, but I don't know if you're ready for a full on gangbang yet!" I laugh. "Well I guess there's only one way to find out!" Sydney replies, giving Extreme and I a sly grin as she heads inside the house....

The end


(If you'd like to be included in a future Sydney gangbang story message me)
       



extreme1

Re: Sydney's Extreme Threesome (A Sydney Sweeney story)
« Reply #1 on: October 31, 2025, 08:08:17 PM »
That was incredible, my brain has melted from the heat coming off this story!
 
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