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Author Topic: Britney Spears: Hollywood Hooker Chapter 4  (Read 3563 times)

Cptnstrwrs

Britney Spears: Hollywood Hooker Chapter 4
« on: April 23, 2026, 09:31:41 PM »
Las Vegas, Nevada 


        It had been over a week since my main girl, Ariana Richards had hooked up for a second time with my friend Dozer. She had told me nonstop how much fun she had with him during their night together. Normally I'd be a little jealous, but with Dozer it's different. Ariana's sex drive is higher than any other woman I've ever met before so anytime I can loan her out to someone else to help take some of the pressure off of me, well, I do just that. I figured Dozer deserved a little reward for his time and I knew just the thing: a weekend trip to Vegas to meet my...business partner, singer turned secret hooker, Britney Spears. Most of her time was devoted to her Vegas show, but any freetime she had was usually spent with high paying clients. It works out great for both of us since I can always use the extra cash Britney brings in, and Britney gets to hook up with as many guys as she wants with no strings attached. Since Britney owed me and I owed Dozer, it seemed like a no brainer to introduce him to Britney.

        We get to the hotel Britney's staying  at a little after eight in the evening and head straight up. The casino she's performing at gave her a penthouse suite that's bigger than most houses I've seen. She gave me a key awhile ago so Dozer and I walk right in after I unlock the door. "Britney, Baby where are you? It's Cptnstrwrs. I brought my new friend Dozer too. He's so excited to meet you!" I say. "Hi. I'm out here! I've been waiting for you two!" Britney calls out from the balcony. We follow her voice outside, Britney sitting in a large hot tub, the water up to her shoulders. "Britney this is Dozer," I say, pointing to my friend. "Hi! It's so nice to finally meet you!" Britney says, standing up. It's almost impossible not to stare at her huge breasts jiggling as she stands, packed tightly into the pink bikini top she has on. I catch Dozer staring...lower at the skimpy pink thong Britney's wearing and I give him a nudge with my elbow. "What? Britney looks good in that bikini," Dozer replies, grinning at Britney and me. "Thanks! You guys want to join me?" Britney giggles, giving us a sly grin. "I don't think either of us have a swimsuit with us," I laugh, trying to make Britney just come out and say what she's thinking. "Don't be silly! You don't need a swimsuit for the hot tub!" Britney giggles, untying the strings on her top, giving us the perfect view of her now naked tits as she undoes the strings on her thong.

        Britney takes a stop back, slowly sitting down in the hot tub, waving us over. I don't know who gets their clothes off faster: Dozer or myself. We climb into the hot tub, Dozer sitting on Britney's left while I sit on her right. She wastes no time, leaning towards Dozer and kissing him. The two of them make out for a few minutes before Britney turns to me and we make out as Dozer slips his hands around her body, playing with her tits as I make out with her. Britney moans softly as he rolls her nipples between his fingers. Not to be left out, I slip my hand between my body and Britney's, alternating between rubbing her clit and finger fucking her, not once stopping our make out session. 

        I could make out with her all night but Britney has other ideas. She pulls away, her lust filled eyes darting between me and Dozer, as if she can't decide who she wants next. "You're a good kisser!" Dozer laughs, inadvertently helping Britney decide. "If you liked my kissing, just wait. I can do a lot of things with this mouth!" Britney growls in a seductive voice. "I can vouch for that!" I laugh. Britney stands up again, motioning to us to do the same. She has Dozer sit on the edge of the hot tub and she bends over in front of him, grabbing his nearly two foot long cock, aiming it towards her open mouth. Moving behind Britney, I wait until she has most of it in her mouth before gently pushing my cock inside her pussy. She moans softly as I enter her, the sound muffled by the huge cock shoved down her throat. Her pussy is just as tight and wet as I remember, and I waste no time, immediately pumping her pussy slowly, fully intending to enjoy every second of it.

        Britney's walls grip my cock tightly as I fuck her from behind, stretching to their limits as I penetrate her as deeply as I can with each thrust. I hear her gag again and again as Dozer slides his massive cock in and out of her mouth, her throat bulging with Dozer's every move. I'm not sure if Britney would have though he night would be going like this, but her muffled cries of pleasure let us know she's still enjoying every second of it. We give it to her good and hard for the better part of ten minutes before I give Dozer a nod, my friend nodding back as I pull my cock from Britney's pussy. I wait until Dozer's fully out of Britney's mouth before speaking. "Ok Baby that was great but we need you to turn around," I say, Britney quickly complying.

        "Oh God! His cock is going to stretch out my pussy!" Britney exclaims as Dozer approaches from behind her. I give him a nod and he nods back at me. "I bet he would...if he was going to be fucking your pussy," I say, giving Britney a moment to process everything. "Oh! OH! Really! I've never had a cock that huge in my ass before!" Britney exclaims, a panicked look on her face. "Well there's a first time for everything. Besides, if Ariana could take it up the ass so can you. I promised Dozer the VIP experience with the world famous Britney Spears as a reward for fucking Ariana nice and hard for me a few days ago. Please don't leave me hanging babe!" I say. With a sigh, Britney reaches back, spreading her asscheeks wide as Dozer presses the head of his cock against her puckered asshole. 

        "Hold on! It's not a party without some music. Alexa! Play Slave For You by Britney Spears!" I laugh, Britney rolling her eyes as the music starts. "Open up," I say, Britney opening her mouth and sticking out her tongue. Dozer pushes into her ass as I slip my cock down her throat. As we pump our cocks in and out of Britney's holes I think we're both trying to move in time with the music and it takes every ounce of will I have to not laugh out loud. Britney moans and groans her approval,  accepting the fact that Dozer and I are going to use her as our personal sex toy all night long. Her lips feel so soft and warm on my cock, and the way she's running her tongue up and down my shaft is nothing short of amazing. "Damn! Britney's ass is tight! Probably one of the tightest I've ever fucked!" Dozer exclaims. "Well it's not like there's been a lot of women willing to let you put that monster cock up their asses!" I laugh. "Ha! I guess you're right!" Dozer laughs back as we speed up our thrusts. Britney takes her hands, grabs her tits and begins squeezing and playing with them as Dozer and I do our thing.

        As I look over at Dozer, I can tell he's not goong to last much longer. But then, with an ass like Britney's is involved, I can't blame him. "Ughh! I'm going to cum soon! I can't hold it much longer!" Dozer growls. "Then don't man! You think Britney hasn't ever had a guy blow their load up her ass before!" I chuckle. Apparently that was all the motivation my friend needed, Dozer grabbing Britney's hips tightly as he shoots his cum deep inside her ass. It definitely catches Britney offguard, the sensation of cum being pumped up her ass causes the popstar to jerk in response, her tongue dragging across my cock at just the right angle. It causes ME to cum next, grabbing Britney's head and holding her in place as I cum. She doesn't fight it, the popstar turned prostitute, gulping down my load happily. I swear I can even hear her groan softly as I finish cumming, almost as if she's disappointed that I have no more cum for her at the moment.

        "Damn Britney! We're only just getting started and you've already taken two huge loads!" I laugh. "Let's take this to the shower and get our dirty cum filled girl cleaned up!" I say. Britney takes us by the hand and leads us to the bathroom. She turns on the shower and steps inside. Dozer and I follow close behind her, Dozer standing in front of her as I get behind her. He begins kissing her as I pull Britney's hair aside and begin kissing and nipping her neck. The two of us run our hands all over Britney's curves, causing her to moan loudly in pleasure.  Slipping his hands under Britney, Dozer lifts her up, then lowers her onto his cock, Britney squealing loudly as the first foot of his cock enters her. Moving closer, I push my cock into her ass as Dozer starts sliding the pop star up and down on our cocks. "Ugghhhh! Agghhhh! I forgot how good it feels to have two big hard cocks inside me! Fuck me guys! Fuck me until I cum all over your cocks!" Britney shrieks, her body going limp between us as we fuck her silly. 

        Seeing as how Dozer is more than able to hold up Britney by himself, I slip my hands around her body, grabbing a tit in each hand and squeezing them tightly. Pinching Britney's rock hard nipples between my thumb and forefinger, I roll the small nubs between them several times. The longer we go at it, the tenser Britney's body gets between us and I know she'll be getting her wish soon, as I'm not sure how she's lasting this long already. She suddenly lets out a loud cry, wrapping her arms tightly around Dozer's neck and shoulders. "Oh fuck! I'm cumming! I...Ugghhh!" Britney wails, her body trembling between us as she climaxes. I don't think I've ever seen Britney cum this hard before, but hey, I'll take at least partial credit for it. She finally finishes and we set her down on her feet in the shower. Dozer and I pull out of her and turn off the water. Britney's still a little dazed and confused so we help her dry off before taking her back to the bedroom.

        We sit here down on the edge of the bed, Britney falling backwards onto her back groaning, her legs hanging off the edge of the bed. "I'm still good to go, you guys. I'll just lie here and you guys can do what you want, okay?" Britney groans, the exhaustion still clear in her voice. I give Dozer a look, shrug my shoulders and walk over to Britney. Grabbing her by the ankles, I put her legs up on my shoulders as I aim my cock for her asshole. I push inside her ass gently, trying to take it easy on Britney, while also allowing myself to enjoy the feel of her asshole gripping ny cock tightly as I enter her. She grabs the bedsheets tightly as I slide inside, moaning softly. I give her ass a couple of slow thrusts as Dozer climbs onto the bed, kneeling over Britney's head. He gently slaps the head of his cock on her forehead and Britney tilts her head back, mouth open and tongue out. Dozer slides the first foot of his cock down her throat and begins facefucking her as I continue pounding Britney's asshole. 

        As Dozer speeds up his thrusts, Britney seems to catch her second wind, using one hand to stroke the part of the cock not in her mouth while rubbing Dozer's balls with her other hand. It's pretty hot and I wish I was in his place right now. Hearing Britney's cries of pleasure increasing in volume turns me on even more, and I start fucking her asshole as hard as I can. The pop star writhes and wriggles between us, pinned in place by our cocks buried deep in either end of her body. We go faster and faster, Britney getting louder and louder, until her cries push me over the edge. "Oh fuck Babe! I'm going to cum!" I growl, shooting my load deep in her ass. "Fuck! Me too!" Dozer says. I watch as he cums in Britney's mouth, his huge cock so far down her throat that Britney's only option is gulp down the nearly gallon sized load. She doesn't resist or panic, swallow every last drop like a pro.

        I pull out of her ass as Dozer pulls his cock out of her mouth, Britney coughing and gasping for air. "You okay Baby?" I ask. Britney nods her head, the corners of her mouth curled into a smile as she finishes coughing. "Are you good to go again?" I ask. "I'm sorry Captain, but you two have tired me out. I can't believe I'm this exhausted already!" Britney exclaims. I look at Dozer, laughing. "Well, seeing as how Dozer was involved, I'm actually surprised you lasted as long as you did!" I say. "The night's still young. You want to go back to the club and see if there are any other lonely ladies out on the town tonight?" I ask Dozer. "Sounds like a plan," he replies. "You good with that?" I ask Britney. "Yeah, don't worry. I'm not mad. Like I said, I need a break anyway," Britney says.

        We dress quickly and are about to head out the door when Britney stops us, a strange look on her face. "What's wrong?" I ask. "Nothings wrong, I just... Remember that party you had a while back? It was basically a small orgy at your house?" Britney asks softly. "Yeah. Cptnstrwrs' Cock A Polooza. How could I forget THAT night!" I laugh. "Could we do that again? I can't stop thinking about how much fun I had that night!" Britney exclaims. "Sure! Let me make a few calls. We'll make the next one even better than the original!" I say as Dozer and I head out the door...


The End


I've been wanting to do another Cptnstrwrs Cock A Polooza story for a while now and I think now's the time. If you have any celebrities you'd like me to include or if you wanted to be written into the story let me know.

NakedLoser

Re: Britney Spears: Hollywood Hooker Chapter 4
« Reply #1 on: April 24, 2026, 01:30:46 AM »
There is something about imagining Britney as a hooker. It is so easy to see
 
The following users thanked this post: Cptnstrwrs

Cptnstrwrs

Re: Britney Spears: Hollywood Hooker Chapter 4
« Reply #2 on: April 24, 2026, 01:32:43 AM »
There is something about imagining Britney as a hooker. It is so easy to see

You should check out the previous chapters  :)

 

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