Chicago, Illinois
Ethan wasn't your average twenty one year old. His father was a big shot music producer, and his mother was a highly successful lawyer. He had everything a young man would want: a huge house, fast cars, and more money than he knew what to do with. To anyone on the outside, his life was perfect, and he had it all. There was only one thing missing, one thing Ethan wanted more than anything: to lose his virginity. It wasn't entirely his fault. He wasn't bad looking, and he worked out occasionally. Somehow, the son of one of the richest men in Chicago hadn't been able to find a woman willing to sleep with him. That's if you didn't count the gold diggers and the women trying to get with Ethan for the fame that came with dating him. His parents had taught him from an early age to stay away from people like that. But as he got older, he found it harder to keep the secret of his virginity from his friends.
That was around the same time his father came to him with an...unusual proposition. World famous pop star Britney Spears had recently started a second career as an escort and prostitute for those rich enough to afford her. It wasn't a well-known fact, Britney and her 'employer' Cptnstrwrs doing what they can to keep that info from going public. Ethan's father had arranged to have Britney spend the night with Ethan...discretely, of course. They were meeting in a motel at the edge of town, far from the huge mansion Ethan had grown up in. The plan was that he would meet Britney there shortly before midnight and spend the night there with her. Parking his car, Ethan hurries to the motel room, knocking softly on the door. Britney opens the door, wearing only a long red silk robe, leaving Ethan speechless. "Hi. Are you Ethan?" Britney asks, smiling at him. He nods nervously several times as he looks her up and down. "Well, come on in, sweetie!" Britney giggles as she takes him by the hand, leading him into the room.
Britney closes the door before leading him to one of the beds in the tiny motel room. She sits down next to him on the bed, putting her arm on the shoulder. "So I talked to your dad, and he told me all about your...situation. How did you want to do this, honey? I could take charge, or you can tell me what to do and I'll do it. Or we could do a little of both. What were you thinking?" Britney asks, softly stroking his cheek with her hand. "H-how about a little of both?" Ethan replies softly, unable to look her in the eyes. "Sounds good, honey. I'll start us off until you feel comfortable enough to take over," Britney says, standing up.
She takes Ethan's hand, helping him up off the bed. Reaching down by his waist, Britney pulls the young man's shirt up and over his head, tossing it aside. Her eyes go wide for a split second as she takes in Ethan's toned physique but quickly pulls herself together as she reaches for his belt. He can tell Britney's a pro at this, judging by how quickly she not only unbuckles his belt but also removes it and throws it aside. Ethan lets out a soft gasp as Britney immediately moves to his jeans, unbuttoning them before pulling down his zipper. She giggles as she pulls his jeans down, leaving the young man only in his boxers. Taking a step back, Britney grins at him, winking at him as her hands move to the robe's belt, tied tightly around her waist. She gives it a quick yank before sliding the robe completely off. As Ethan looks her up and down again, he really thinks he's dreaming.
Despite being two decades older than Ethan, he still thinks Britney is one of the hottest women he's ever seen. And he's one of the few people to ever see her in her bra and panties in person. Britney's wearing a matching silk black and white bra and panties. His eyes are drawn to Britney's panties, hugging her curvy hips. The only reason he can look away is to admire Britney's large, supple tits, threatening to burst out of her tight bra. He swears he can see the bulge of her nipples pressed hard against the fabric as Britney closes the gap between them, straddling the young man. She kisses him hard, slipping her tongue into his mouth, clearly catching Ethan off guard. He recovers quickly, their tongues wrestling each other in Ethan's mouth as Britney runs her hands all over his body.
After just a few minutes, Britney stands, turning her back to Ethan. " I want you to undo the back of my bra. You'll definitely impress the ladies if you can get their bra off on the first try!" Britney laughs as Ethan reaches for the clasp on her bra. He quickly undoes it, surprising Britney. She turns to face him, holding her bra on her tits with one hand while sliding the straps off her shoulders with the other. "Have you ever seen a pair of tits before?" Britney asks. "No, I've never gotten that far on any of my dates," Ethan says, avoiding eye contact. "Hey. It's alright. Tonight, these are just for you!" Britney says, pulling off her bra and letting him get a full look at her tits. His eyes go wide with shock, but Britney can tell that the longer Ethan stares at her huge, naked tits the hornier he becomes. "Go on. Do whatever you want with them. It's ok," Britney says softly, trying not to overwhelm the young man.
Slowly, his hands shaking, Ethan reaches out, cupping one of Britney's tits in either hand. He gently squeezes them, Britney letting out a low moan of approval. Puting her hands over Ethan's, she moves his hands so they're covering her nipples. The young man gets the hint, pinching, pulling and rolling her small fleshy nubs between his fingers until they become rock hard. Taking his hands off Britney's breasts, Ethan stares intensely into her eyes. Britney nods, and Ethan leans in, flicking his tongue across one of her nipples before he starts to suck on her tit. He goes back and forth, over and over, Britney moaning and groaning as the young man sucks on her tits like a big, hungry baby. She lets him have his fun for a few long minutes before she stops him.
Britney stands up, motioning to Ethan to do the same. Once he's standing in front of her, Britney reaches over and grabs the elastic waist of his boxers, Ethan's eyes going wide. "Don't worry, baby! I'll be gentle!" Britney giggles as she pulls the young man's boxers down his legs. Even though the whole point of tonight was to get him laid, Ethan feels a little embarrassed standing naked in front of Britney. She doesn't give him time to worry about it, however, having Ethan sit back down on the bed as she kneels in front of him. She pushes her tits together, Ethan's average size cock disappearing between them, and Britney begins slowly tit fucking him, staring deep into his eyes the entire time. Britney lets him enjoy the feel of her soft, warm tits against his cock until he's completely hard. Letting go of her tits, Britney notices the look of disappointment on Ethan's face. The shocked look returns, however, as Britney opens her mouth, eyes locked on Ethan's as she leans in towards his cock. He lets out a loud groan as Britney's lips wrap around the head of his cock, the pop star flicking her tongue all over the tip of it. Ethan's groans turn into moans as inch by inch, Britney slides her head down, swallowing his cock. The young man watches in a daze as Britney's head slowly bobs up and down between his legs, her cheeks hollowing out over and over as she gives him his first blowjob.
As if to confirm the fact that Ethan has never been blown before, Britney can feel his cock tensing up in her mouth, quivering in anticipation. "No!" Ethan cries out, but it's too late. He begins to cum, Britney tightening her lips around his cock as he begins to pump his load down her throat. Ethan watches in a mix of embarrassment and arousal as he sees Britney gulp down shot after shot of his cum, her throat bulging each and every single time. She even gives him a couple of quick sucks as he finishes cumming, as if she's making sure he's completely done. Britney slides her head of his cock, staring up at him as she licks her lips clean. "Oh man! That was so fucking embarrassing! I couldn't stop myself from cumming so soon!" Ethan whines. "Oh sweetie! It's ok! There aren't many men who can last long once their cock is in my mouth!" Britney giggles. She stands up, gesturing to Ethan to do the same. "Besides, now that you've cum, you should be able to last a little bit longer now," Britney says, laying down on her back in the center of the bed. "I know tonight is supposed to be about me making sure you don't leave a virgin, but I think it's also important we work on your other skills in the bedroom," Britney says, looking up at him. "Like what?" Ethan asks, confused. "Well, for starters, you should definitely know how to eat pussy," Britney says, spreading her legs wide as she waves him over.
Ethan gets on the bed, slowly crawling to Britney, stopping only once he's between her legs. Still clearly nervous, he slowly lowers his head between her thighs, flicking his tongue lightly against her clit a few times. "Ugh! Just like that, Baby! Don't stop!" Britney moans. Encouraged by her response, Ethan speeds up his tongue, as well as the area between her legs that he's licking. Britney's cries of pleasure, louder than before, let him that she approves of his technique. Considering that Ethan is a virgin, Britney's surprised how great he's doing with eating her out. She reaches down, grabbing his head in both hands and pulls him towards her, as if she can get him even further inside her pussy. As he works his tongue into Britney's every nook and cranny, she realizes that she has to stop him sooner rather than later. If he makes her cum now, Britney knows there's no way he makes it through their fuck fest without cumming before her. "Okay, baby! I hate to do this since you're doing so good, but I'm going to need you to stop. Now that you're hard and you got my pussy all nice and wet I think it's time for you to finally fuck me," Britney says.
Slowly, Ethan moves himself from between her thighs, sort of kneeling in front of her. Taking his cock in one hand, he leans in, guiding it towards Britney's pussy, not once breaking eye contact with the pop star. The head of his cock finally brushes up against her pussy lips and Britney nods at him to continue. As nervous as he is, Ethan's excitement gets the better of him, pushing his cock inside her with one hard thrust, rather than enjoy the moment sliding into her inch by inch. "Oh fuck!" Ethan exclaims, eyes wide, as he feels Britney's tight, wet pussy gripping his cock in a deathlock. "Go on, baby! Do it! Fuck that pussy! It's alright!" Britney moans, nodding at him. That's all the encouragement Ethan needs, the young man immediately beginning a slow in and out rhythm of thrusts, never pulling completely out of her pussy. "Ugghhh! Oh yeah, baby! Just like that! Give it to me! Uggghhhh!" Britney groans, grabbing the sheets tightly as he fucks her. His lack of experience is replaced by his eagerness, Ethan speeding up his thrusts, Britney's huge tits bouncing wildly as she's fucked hard. Ethan reaches down, grabs a tit in either hand, and squeezes hard, using them as make shift handles as he fucks the pop star. Britney swears he goes harder and harder with each thrust and decides she needs to regain control of the situation.
"Ugghhhh! Agghhh! Hey, sweetie. How about I get on top and fuck you for a little bit?" Britney asks. She's barely stopped speaking as Ethan pulls out of her, laying on his back on the bed next to her. "Ok. That sounds good!" Ethan replies eagerly. Britney pulls herself up, swinging a leg over Ethan's hips as she straddles him, reaching for his cock. Guiding it to her pussy, Britney pushes her hips onto him, the familiar feeling of the young man's cock inside her quickly returning. She's still surprised that someone so inexperienced could get her so wet, but as Britney begins riding Ethan's cock she's glad he did. "Agghhh! Uggghhhh! Fuck Britney! Your pussy feels so fucking good!" Ethan groans, writhing in pleasure beneath her as she grinds her hips on his cock. Britney's always been able to please the man she's with, so a sex starved twenty year old virgin is no match for her and her pussy.
Determined to make sure Ethan never forgets tonight, Britney speeds up, riding the young man as hard and fast as she can. The sound of their naked bodies slapping against each other turns both of them on, Britney wondering how long it will be before Ethan cums again. He reaches up, grabbing her tits again, massaging and squeezing them as the pop star continues thrashing around on his cock. A few minutes later, he moves his attention to Britney's ass, grabbing and slapping it as she bounces up and down. "Ughh! Agghhh! Oh God! Your cock feels so good inside me Baby!" Britney shrieks, rubbing at her clit as she fucks him. As the seconds pass, Britney feels the pleasure building up inside her, pushing her closer to her limit. Whether by accident or not, one of Ethan's fingers slips into Britney's asshole as the young man is groping her ass, finally causing Britney to succumb to the pleasure inside her. "Oh shit! Oh fuck! FUCK! I'm cumming Ethan! I'm cumming all over your big hard cock!" Britney screams, trembling in ecstasy as her orgasm overwhelms her. It ends up being more than her young lover can handle as well, Britney feeling the telltale sign of the trembling cock inside her, alerting her to what's about to happen.
"It's okay, Baby! Cum! Cum inside me!" Britney exclaims, weathering the last few bits of her own orgasm. She senses no hesitation from Ethan, as the young man cums inside for the second time tonight. Too exhausted to get off of his cock, Britney feels his cock explode inside her like a volcano, filling her pussy with his load. He seems to cum forever, Britney feeling trails of his semen leaking out of her, running down her thighs. "Oh sweetie! Look at the mess you made!" Britney giggles as she climbs off of him. Ethan is so physically and emotionally drained that the only response he can give her is a low groan, still recovering from his own orgasm. "I'm going to go clean up in the bathroom real quick. I'll be right back!" Britney says, kissing him on the cheek before she runs to the bathroom. As the daze begins to fade away, Ethan still can't believe all this is really happening to him. He's been titfucked and blown by the legendary Britney Spears, fucking her stupid, and had her ride him in return. And if all THAT wasn't enough, now he's came in not one, but TWO of her holes. He feels like one of the luckiest men alive. As if to emphasize that fact, Britney walks back into the bedroom in all her naked glory.
She stares at Ethan for a moment before finally speaking. "So I was thinking about what just happened while I was in the other room, especially when your finger ended up my ass. I think the next thing we should do is have you fuck me in the ass. Sooner or later one of your girlfriends will want to do anal, so why not get some practice in tonight?" Britney asks, giving him a sly grin. "O-okay. That sounds good..." Ethan replies nervously. Britney climbs onto the bed, crawling on all fours to him. "It's not too different from what we've already done. Just get behind and push your dick into my asshole," Britney says, wiggling her ass in his face. Ethan springs up, moving behind Britney, kneeling down so his cock is lined up perfectly with her waiting asshole. He puts a hand on either of Britney's asscheeks, spreading her wide. Spitting on her asshole, Ethan decides he's ready and begins slowly pushing himself into Britney's ass. "Ugghhhh!" Britney and Ethan groan as he enters her, inch by inch. As slow as he entered her, well, once he's fully inside, that's a completely different story. Ethan begins pounding Britney's asshole as hard as he can, holding her tightly by the hips as he fucks her.
As the young man annihilates her asshole, Britney starts to winder if she's enjoying this more than Ethan. True, he's moaning and groaning as loud as she is as he takes her from behind, but no one has ever fucked her ass this good before. And considering how many times Britney's been fucked in the ass, that's saying something. Faster and faster, Ethan rams her from behind, Britney grabbing the bedsheets tightly in her hands as she wails in pleasure. "Oh yeah, baby! Fuck that ass! You're fucking my ass so good!" Britney whines, encouraging Ethan even more. He reaches around, grabbing Britney's tits and squeezes them hard as he fucks her. In all the chaos, Britney slips a hand between her legs, alternating between rubbing her clit and fingering her pussy as Ethan focuses on her asshole. Just as she feels herself about to orgasm, Ethan begins her to the punch, his hard cock quivering in her asshole. "Ugghhh! Cum for me baby! I want you to fill my ass with your hot load!" Britney growls. Ethan does as he's told, pumping her ass full of his cum as Britney cums beneath him. He's completely oblivious as he shoots shot after shot of his load deep inside her.
It only takes Ethan a couple of minutes to finish cumming, but to Britney it feels like hours. He pulls out of her ass, Britney rolling over before she sits up, wrapping her lips around his cock. She quickly sucks him clean before collapsing onto her back on the bed. Ethan stares down at her naked body, smiling at her. "You made another mess! But, hey, how many guys can say they've cum in all three of my holes in the same night?" Britney giggles, Ethan staring at her confused. "Not a lot, sweetie! That's my point. Tonight, you joined a very exclusive club, that's for sure. I probably shouldn't tell you this, but your father didn't pay for anal. I decided to throw that in for free after you fucked me so good!" Britney laughs. "But don't worry about all that! We still have the rest of the night. Although...I really do need to take a shower. Did you want to join me?" Britney asks with a smile. "Totally!" Ethan exclaims. "Ok. I'll race you!" Britney giggles as she runs naked for the bathroom. Ethan just smiles as she passes him by, knowing the even though he lost the race, he's still the big winner tonight....
The end...
Topic: Britney Spears: Hollywood Hooker Chapter 2 (Read 7679 times)