Oh Britney

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Guy gets a shot with his fantasy.
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I have a thing for Britney Spears, what can a guy say? You can call her washed up, knocked up, whatever you like, but there's just something about her.

December 15, 2003:

A posting to New York was supposed to be good for Jimmy. More money (American dollars at that), a leadership opportunity, and a guaranteed raise on his next performance appraisal. But, as it turned out, things weren't quite that great where the "rubber hits the road," as they say. Here it was, 11:59 pm and he was just getting onto the elevator from the hotel's underground parking.

ISO 9000 auditing was turning out to be a lot more boring than he thought it would be when he took the job right out of college. The only Canadian graduating from Harvard near the top of his MBA class, the job offers had been plentiful on both sides of the border. The consulting firm he signed with offered him a $20,000 signing bonus up front. How could he resist that?

New York, the city that never sleeps. He'd seen all the shows, including the occasional episode of "Sex in the City." Models were supposed to be everywhere. Gorgeous women were plentiful and should have been easy pickings for a single guy like him. Helped if you knew someone, New Yorkers could be pretty cold to outsiders. He certainly wasn't making any friends at the client, forcing them to document all these processes and procedures; he was a pain in the ass to them. They didn't want him around 9 to 5, let alone like him enough to hang out with him after work.

He couldn't even enjoy everything the swank "W" hotel had to offer. Massages, room service, spa, gym, pool. By the time he got home all he was ready for was bed. The beds were really nice; at least he could enjoy those. He had room service deliver his breakfast bright and early then he was gone before the sun even came up.

Hitting the button for the 21st floor, Jimmy smirked. When he first got to town he thought things would be different. He wasn't a model or anything, but he'd gotten his fair share of girls. With a high-class address like the "W" to drop into conversations, he thought he'd score for sure. No such luck, he'd struck out with the cool and confident New York women and had given up after the first couple weeks of getting shot down.

The elevator rose to the ground floor, the level with the front lobby, and stopped.

"Ah fuck," Jimmy cursed. Just what he needed, a delay on his way to bed.

As the doors opened, an extremely large black man in a tailored suit grabbed the door and stared at him intently. A minute of silence passed and Jimmy started to wonder what the hell was going on. The man looked over his shoulder and ushered someone in. Another large guy, this one white, entered the elevator with a petite blonde held firmly to him. She was quickly ushered into the far corner of the elevator and the two men turned on Jimmy.

"Who's this guy?" the white guy asked the black one, who was now allowing the door to close and facing Jimmy. The petite blonde was hidden behind these two giants and Jimmy began to feel like the criminal about to get the good-cop, bad-cop routine.

"He was on the elevator, looks harmless enough," They were talking at him, not to him, but Jimmy felt he should answer.

"Look, I'm a guest here, I'm staying on the 21st floor. It's been a long fucking day so just leave me alone okay, I don't want any trouble." He showed them his electronic room key.

"Boys, lay off the man would you?" the girl piped up from the corner. She was leaning against the far wall of the elevator facing Jimmy. When the large white bouncer turned to talk to her, Jimmy thought she looked familiar.

"Britney, you can't be too careful you know, there's a lot of wacko's out there."

"Are you a wacko?" she asked Jimmy pointedly. Removing her sunglasses she brushed the hair out of her Bambi-like, brown eyes.

"Me? No, I'm in town on business. I..... Britney, Britney Spears?" Jimmy's stomach almost came thundering up his throat. Taking her gorgeous visage in, he began to get a hard on. Barely six-feet away stood the woman he'd fantasized about, literally, hundreds of times. He once started masturbating to "I'm a Slave for You," and had blown his load before the video was even over. More than a few times he conjured up visuals of Britney to get off when one of his uptight girlfriends was giving him an inept blowjob or a lousy lay.

"Are you okay, you look a little pale," she approached him placing her hand on his cheek. The soft skin of her hand caressed his chin, rough with a 5 o'clock (and then some) shadow. Moving her fingers slowly along his chin, she gently scratched his lips with the long fingernail of her middle finger. Jimmy had gone completely blank and just stood there grinning like a moron.

"What's your name?" She raised his chin with the same finger, lifting his gaze from her chest. She wore one of those cheeky T-shirts, seemingly for the media, and it barely contained her ample breasts. What are you looking at? It read directly across her chest. Her nipples were clearly showing through the thin material, especially if one had been staring as intently as Jimmy had done.

"Uh, I'm Jimmy. Jimmy McLean, I went to Harvard!" He blurted out, finally making eye contact. I went to Harvard? What the fuck was that? He though to himself. That's going to impress Britney Spears?

Smiling broadly with that perfect, angelic smile she stifled a laugh. "Well Jimmy McLean that went to Harvard, you smell awful and you look eve worse."

He suddenly became conscious of how he must look, tie undone, pants and shirt all wrinkled. He hadn't shaved for practically a day, hadn't washed all day, God even his breath must stink. Damn, why didn't' he meet her in the morning when he looked and smelt (and felt) like a million bucks!

The elevator made a slight "bing" and it came to the 21st floor. The black bodyguard got out of Jimmy's way and pointed out. "Your floor sir."

"Yes, yes it is. Listen, Britney, I know this is corny, but, my little sister, she's a huge fan. Could I maybe get an autograph? I'm sorry to ask, but if I tell her I met you and didn't get it for her she'd be crushed. I'd win the brother of the year award for sure, please? If it's not too much trouble?"

"Ah that's so sweet," Britney said in that All-American, down home girl voice. She actually made Jimmy blush. He had no little sister; he just needed an excuse to talk to her some more. He never wanted to get off that elevator. "Look, I don't have a pen or anything on me and we have some promotional stuff in my room. Why don't you get cleaned up and come on up in a little while?" she was fixing his hair as she said this and Jimmy was completely transfixed.

"Yes....," was all Jimmy could say. He stood there dumbly until one of the bodyguards literally yanked him out of elevator. As the door began closing, Jimmy lunged back into the elevator. One guard grabbed him as the doors tried to close shut on the struggling pair.

"WAIT, Wait, what room are you in? What room?"

"Just go to the top floor, I'm in the penthouse, you'll find it. Let him go Jack."

With that the doors closed gently and Jimmy stood staring at them. Then he burst into action, running down the long hall to his room, he was so excited he fumbled with the key for what seemed like forever. Hurtling himself into the room, he became a human whirlwind with clothes flying off in all directions. Throwing himself into the bathroom he quickly washed his face and gave himself a Mexican shower above the sink. Slapping on deodorant with one hand and brushing his teeth with the other his mind was racing.

Britney Spears had just invited him back to her room! Okay, maybe he lied a little bit, but still. No one back home was going to believe this. He had to fight the urge to call his buddy Mike at home to brag before heading up. Sorting through the drawers for clean clothes to wear, he threw on his favourite shirt and best suit. He had to slow down, he was sweating again. Looking at himself in the mirror, Jimmy gave himself a little pep talk before leaving.

Finding the penthouse was, indeed, no problem. Heading to the top floor, it was the entire top floor. The doors opened and Jimmy was greeted by the same two bodyguards with indifference. One escorted him into the room and sat on the couch opposite Jimmy, informing him that Britney was in the washroom and would be out shortly.

Jimmy rose and walked to the large windows with a beautiful view of the city and Central Park. He could see the bodyguard's eyes glued to him from the reflection in the window. Glancing around briefly he turned to take in the penthouse suite. Lavish wasn't the word, even his boss's house wasn't this nice and he was a millionaire.

"What do these rooms go for?" Jimmy asked the guy, trying to make small talk. He didn't answer, just sat staring at him.

"Okay, not one for the small talk, eh?" Jimmy turned nervously back to the window. He heard a solid door shut and could see Britney approaching him from behind. Fighting the urge to spin around, he played it cool and kept looking outside.

"Ah Jimmy, you clean up nice. Do you like the view?" she stood next to him, wrapped in a terry cloth robe and drying her hair with a white towel.

"Yeah, it's beautiful. The sunrise must be awesome." He turned to her as she wrapped the towel around her amazing blonde locks "Aunt Jemima" style. She snuggled up to him like a horny slut on the Axe Body Spray commercials and audibly took in his aroma.

"Mmmmmm, you do clean up nice. Much better." She whispered seductively. Quickly, she turned to the bodyguard and walked to the couch. Jimmy had to think hard, the moment passed so quickly. Did he just imagine that or did Britney Spears just hit on him?

"Jack, take off will you, get some sleep. We have a lot of travelling to do tomorrow. Go!" Britney commanded and the guard obeyed.

"Come, sit," she said motioning to the chair across from her.

"What?" Said Jimmy, then clued in. His mind had been racing in a dirtier direction, but he understood and took a seat across from her.

"So what is your sister's name?" Britney asked, looking up from the coffee table. Her breasts hung low and were clearly visible even with the robe on. She was leaning over a poster of her gorgeous, sweaty body in a tight stage outfit with a pink pen in hand awaiting Jimmy's reply.

"Who?" Jimmy asked, intoxicated by the sight of her, knowing she was so close to being naked before him. He completely forgot his story.

"Your sister, the one you wanted the autograph for? You don't have a sister do you?" She rose to sit back in the chair and crossed her arms.

"Well, I....."

"You don't! You just wanted to sell my stuff on eBay, is that it? Make a few bucks."

"No Britney, I just wanted to meet you. You're so hot."

"Oh, that's original. Is that the best you can come up with? What kind of pick up line is that? Why shouldn't I call the boys in here to beat the crap out of you, huh?"

"Come on, give me a minute, please? I've had the hots for you since your first video. I'm sorry I lied, I just didn't know how to ask you out, right there in front of your goons. I couldn't just say hey, Britney Spears, want to go out with me, Mr. Nobody? You wouldn't have said yes."

"Oh, so now I'm a snob?" Britney stood up with hands on hips. She did not look impressed. However, with her robe now opened wider her chest was exposed from her sexy cleavage to her belly button.

"Aw come on, you're not a snob. You're gorgeous. You're sexy. Your smile is breath taking. God, when you touched my cheek I thought was going to pass out." Jimmy moved closer to her, speaking more softly.

"Well...," Britney blushed a little and looked down as Jimmy approached. Strands of her blonde hair fell over her eyes. Seeing his chance, Jimmy reached up and brushed the hair out of her face. Holding her head firmly in his hand he pulled her to him and kissed her.

Excitement and adrenaline rushed through his body as he cupped Britney's terry cloth-clad ass in his left hand and pulled her groin to his. Just as he started to plunge his tongue into her mouth, Britney pulled away and slapped him hard across the face.

"That's for lying to me. Jerk!" Then Britney embraced him once more, kissing him this time. She roughly pushed off his sport coat and tore open Jimmy's favourite red shirt. Buttons bounced on the floor.

"Jesus!" Jimmy was shocked. The slap he expected, but he also expected to have the shit kicked out of him right after. Instead, Britney had started to tear off his clothes.

"I'm so horny," Britney murmured as she began undoing his belt. Jimmy wore boxers and his arousal quickly became apparent as the belt buckle clanked on the floor. "Ohhhhh," she cooed as Jimmy's cock bounced up just as she pulled his boxers down.

"Oh my God, oh God," Jimmy moaned as she took his raging hard on into her mouth. Gazing down at her, he pulled the towel from her head, freeing her wet blonde hair to fall on her shoulders.

Glancing up at him as she sucked hard on his cock, she thought he was going to cum right there. Slowly squeezing the base of his cock and his balls with her hands, she said "Don't you dare cum in my mouth! Do you hear me?"

"Yes, yes Britney," Jimmy was overwhelmed with excitement. Britney Spears had his cock in her mouth. Oh man, how sweet would it be to cum in her mouth? Maybe she would have sex with him? He couldn't believe his luck.

Britney returned to his cock, taking him into her mouth. The pre-cum was already flowing steadily, filling her mouth with its salty taste. His cock wasn't huge, but it would do. It'd been ages since she had gotten laid and this lucky guy had played his cards right. Cute, but no one would believe he'd slept with her.

Running his fingers through the matted wet hair of his fantasy girl, Jimmy closed his eyes and focused on the sensation. She was forcefully deep-throating him. He could feel the gentle touch of her teeth along his shaft as the head pushed through her soft lips, along her tongue, and into the back of her throat.

"Gulp, gulp, gulp," Jimmy was getting the blowjob of his life and his knees were getting weak. Just as he thought they would give out, she stopped fucking his cock with her mouth and grew more gentle. She began stroking his slick shaft with her hand while lightly sucking and licking the head.

"Ohhhhhhh yeeesssss," Jimmy moaned as he could feel the cum rising from his balls. "Oh God Britney, I'm going to cum, I'm going to cum!"

Just as Britney suspected, Jimmy was so horny and excited he barely lasted 3 minutes. While best known for "singing," her other oral talent surpassed that ability ten fold. Good, she thought, he'll blow his load then he should be able to fuck me for more than 10 seconds.

"Ohhh good boy, cum for me Jimmy. Cum for me!" Britney stroked his cock with her left hand and cupped the head with her right. Within seconds, Jimmy blew a hard and heavy squirt of cum into her palm, followed by another, then another.

"Ooooohhh God!!!" Jimmy moaned, "Oh God, oh Britney. Yes, ahhhhh." The first explosion of cum released a torrent of sexual frustration. That was phenomenal! He thought, leaning back against the cool glass of the window as the eruptions from his dick spewed less and less semen into Britney's soft hand.

"So much cum, you naughty, naughty boy." Britney milked that last of his load and used his boxers to wipe her hands clean. Rising to face Jimmy, who was still leaning back and staring at her, she took his hand in hers.

"Come with me...." The pair walked hand in hand towards the bedroom. In it Jimmy saw the largest bed he'd ever seen in his entire life.

Turning to him as they reached the bed, Britney undid her robe and allowed it to fall to her feet. Her gorgeous body made Jimmy grin from ear to ear. Still wet hair clung to her cheeks and shoulders. Firm and full breasts topped a chiselled stomach. Her pussy was completely shaved and her thighs looked soft and inviting.

Sitting on the edge of the bed, Britney spread her legs opening her sex to him. "Please, taste me Jimmy?" She said in the sexiest innocent voice he'd ever heard in his life. Flashing her million-dollar smile at him, Britney rested her hands on her beautiful breasts and began massaging them.

Despite the fact he'd blown the biggest load of his life only seconds before, Jimmy could feel his erection growing once more. Falling to his knees, he began to worship her sex. Running his cool, rough fingers along the soft, delicate skin of her thighs made her giggle. Her skin was still warm and moist from the shower.

Not wanting Jimmy to waste any more time, she ran her fingers through his hair and pulled his mouth to her pussy. Jimmy gladly began to kiss and lick it. She must have just shaved in the shower, because she was so soft with no hint of stubble to grind his face like sandpaper. She's going to let me fuck her! Jimmy could barely contain his excitement as he ran his tongue up and down her lips.

"Ooooohhhhhh," Britney moaned and she squeezed her nipples. "Oh yes Jimmy, kiss me there! Kiss me there! Yes!" Throwing her hair back in a motion not unlike her stage performances, Britney was thoroughly enjoying the tongue-lashing this guy was delivering.

For his part, Jimmy's mind was racing. I'm going to fuck Britney Spears, I'm going to fuck Britney Spears! He made sure to get her nice and wet. Licking and slobbering like a dog at a bowl, he was too happy to be there. He stroked his hard cock slowly, not wanting to get too excited, but too excited to stop touching himself.

Jimmy ran his free hand along Britney's tight stomach and up to her breasts. Taking his hand in hers, she let him squeeze and explore her body. Her breasts felt fantastic and he couldn't wait to worship them, but Britney had other ideas. As he tried to rise she wrapped her shapely legs around his shoulders and halted his advance. Pushing him down and into her groin she laughed.

"Tisk, tisk, get back to work you naughty boy. You came, now suck me. Lick me 'til I cum!"

Not wanting to disappoint her, Jimmy allowed her to guide his mouth back to her pussy. He was strong enough to force her on her back and take her right there, but he didn't want to push his luck. He wasn't that forgone with lust to risk stopping this. He planned to give Britney what she wanted until he could take what he came for.

Her clean-shaven pussy was getting wetter with her juices as he got back into the task at hand. Jimmy's tongue played up one lip, then down the other over, and over, and over. Britney was whimpering and running her fingers through his hair. Then, when he thought he'd teased her enough, he thrust his tongue as deep into her pussy as he could.

"Ohhh yes, yes Jimmy. Eat me, EAT ME!" She moaned.

Judging this response to be positive, he plunged his tongue past her lips and into her again and again. His nose was rubbing against the top of her sex as he strove to get his tongue as deep as he could.

"Yes, yes. Fuck that pussy with your tongue. Good boy, good boy!"

Britney was wetter than any woman he'd ever had before. His face was covered with her cum as she ground herself onto his face. Releasing his cock, Jimmy thrust his finger into the top of her pussy and began to stroke her G-spot with a repetitive, "come here" motion with his middle finger. This got exactly the reaction he was hoping for.

"Oh god, yes! You fucker! You fucking great pussy licker! Oh yeah, your finger, yes, yes, that's so good right there, YES, OOOOHHHH YES!!!!"

Britney came hard and fast. Jimmy couldn't believe the mouth on her, shy, demure Britney was cursing up a storm. Then, her cum gushed from her pussy and squirted him hard in the face.

"Unnghhh, god," his eyes searing with pain at this unexpected outburst, Jimmy backed away slightly.

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