Fortune Favors the Bold

Tom had been playing it cool all night long. Throughout dinner, and the movie, and the dessert afterwards, he had been the perfect gentleman. He was sociable, focused, and considerate. He'd held doors, pulled out chairs, and limited his furtive glances at her body to times when he was sure she wasn't looking. So why now, as Sarah was driving him home, did he feel like he had just wasted his shot?

His car was in the shop being repaired and she had driven him around all night. In retrospect, he was glad for it- it allowed him to spend all the time in transit staring at her and her beautiful body. As they drove down the highway and the car was illuminated by the intermittent orange light of the lampposts, Tom took another opportunity to admire her. Sarah was taller than the average woman, but she was still a half a head shorter than him. Her soft cheeks were lightly freckled and the pale skin of her shoulders shone brightly against the darkness. She had fiery red hair that tumbled down to her shoulders, with just a few simple curls to frame her beautiful face. It looked to Tom that she had tried her best that evening to wear clothes to reflect her nonchalant, aloof attitude, but the allure of her body shone through in spite of herself. A casual sweater covered her cleavage but pronounced the outline of her breasts, and followed the hourglass indent of her waist. Dark blue jeans were simple, but they couldn't help but cling tightly to her bouncy, irresistible ass. Sarah's ass was a bit larger than normal, but it swayed seductively with every step. Tom had always had a thing for large behinds, and refraining from staring too hard at Sarah's had been the biggest challenge of the evening. As Tom sat in the passenger seat of Sarah's car, he began to panic that he wouldn't have the chance to undress her with more than just his eyes.

They were old friends from high school who had spent months talking online. They lives in different states, far removed from each other and unable to do much more than casually keep in touch. But in the last few weeks, their conversations had become increasingly flirtatious and stretched late into the night. They never evolved into anything explicitly stated, but a week ago they had reached a fever pitch where the implied sexuality threatened to bubble over into a full-blown episode of carnal and agitated phone sex. The morning after that tense night, Tom had asked Sarah for a date in the upcoming weekend when they would both be in their home state, and she had accepted eagerly. Tom was sure that after so much talking their night would quickly devolve into an explosive outburst of crazed fucking and realized passions, but so far Sarah had seemed almost passive. Tom's mind was racing as the car raced down the freeway towards his home and his time remaining continued to dwindle away. It would be a long time before he saw Sarah again. He had been the perfect gentleman! He spent the evening subtly flirting and attempting to insert opportunities into their conversation for her to turn a comment into a sexual advance, and she had coolly denied them all. Perhaps he had been more passive in his advances than he had thought? He had to think of something quick, before she dumped him in front of his house and sped away.

"Hey! What are you thinking about?" Sarah's call to him snapped him away from his panicked thoughts and back into the moment. "Do you mind if we stop for gas? I'll have to do it on the way back to my house if I don't do it now." Even as Sarah asked she was directing her car onto the exit ramp. As they pulled up to the traffic light below the highway, Tom's mind was racing, desperately searching for some clever way to take advantage of this opportunity. His adrenaline began to rush and he began to psyche himself up to make a move before he even had a plan of action. The car pulled into a gas station, empty but for their car and the attendant in the window of the convenience store. It was past midnight, and it was almost eerily quiet. Sarah hopped out of the car and walked around to his side to begin pumping gas.

As she put the pump into the gas tank and locked the trigger in place, Tom felt himself let go of all conscious thought. It was as if another force moved him- he exited the car and let the door hang open behind him. Sarah gave him a quizzical look that turned to wide-eyed apprehension as Tom suddenly stepped up close to her. Their faces were only inches apart and her face registered surprise and a sudden nervous energy as he looked deep into her brown eyes. Sarah whispered "Hi," and looked back at him for an instant before he rushed forward the last few inches and met his lips with hers. It was not a particularly gentle or tender kiss; after a whole evening of being gentlemanly and courteous to her, Tom had decided to discard his timid approach. The kiss was hurried, and passionate, with an urgency that betrayed his need to know what her lips felt like against his. It was a short kiss, but indescribably electric- Tom broke it with a sudden and great gasp of air as if he had not breathed for several minutes, and in that instant, all barriers between the two of them were broken.

Tom's body crushed against Sarah's and pushed her back against the car. His hands began to wrap around her and pull her tight as she draped her arms around his neck. She drove her tongue deeply into his mouth, aggressively tasting him for the first time, and Tom's erection- so valiantly held in check for most of the evening- pressed hard against Sarah's stomach. They pulled each other more tightly together, as if trying to make their bodies one, only breaking their kiss long enough to breath before diving back into one another. As the gas pump clicked off and the gas station radio drifted down from the fuzzy speaker above them, Tom and Sarah began to run their hands all over each other. After what seemed like an eternity, Sarah pushed Tom away with a hunger in her eyes and hurriedly removed the gas pump and raced around to the driver's seat of the car. Tom hopped in the passenger seat and Sarah peeled out of the gas station, taking off with a screech. She drove only a short ways down the road before she ducked into the parking lot of a department store, directing the car to the darkest corner of the parking lot before turning off the car and turning back to Tom.

Tom kissed her for just a moment before pulling her into the backseat of her car. Within moments she was straddling him, cramped but perched atop him so that she was grinding down against his crotch. Sarah made little moans into Tom's mouth as she bore down on him and ground her hips into his. Their tongues danced and she would intermittently bit Tom's lower lip. Every time she did, she would feel his strong grip on her get a little tighter and feel his sudden, sharp intake of breath. Then, as she ground her hips extra hard down against him and sucked his bottom lip into her mouth, she broke through another barrier of his cautiousness and self control. She was suddenly thrown down along the backseat of her car and Tom was upon her, running his hands all over her body and grinding against her however he could. There wasn't much room in the car, but he still found a way to remove her jeans and he was quickly beginning to run his hands over her exposed ass and across her hips. Tom could feel the heat coming from Sarah's crotch and he ran her hand over her still-covered clit.

Even given the sexual frenzy they found themselves in, he was still shocked to feel how wet Sarah was even through her panties. Tom longed to taste her juices and feel them gush around his tongue as he ate her pussy to orgasm, but there was no room in the car to get between her legs and at any rate, he was entirely too desperate to feel this sexy woman's pussy wrapped around his dick. He looked into Sarah's eyes and saw the same burning desire within her, and that was all he needed to lose the last of his consideration and courteous attentiveness to her needs. With an impatient growl he rose from atop of her to undo his belt and remove his pants. While Tom kicked off his boxers, Sarah had removed her panties, exposing her pussy to him for the first time. Even in the semi darkness, it was beautiful and maddeningly alluring- it appeared so aroused that it was almost literally dripping fluids as Sarah quickly returned to straddling Tom. She was facing him and they kissed deeply for just a moment, eliciting a small whimper from Sarah, before she reached down between her legs and wrapped her fingers around Tom's cock. It wasn't extra large- just shy of 8 inches in length, but it was thicker than average, and at the moment every inch of it positively throbbed with a need to be buried inside of her. Sarah could see the angry red color of the engorged head even in the dark, and she heard Tom gasp as she lined the very tip up to the entrance of her pussy.

Suddenly, steadily, Sarah sank all the way down on Tom's cock, taking the entire length into her pussy in one smooth motion. The air rushed out both of them as she did so, and for a moment, the car and the world were utterly silent. Their hips were smashed together, and Tom could feel his cock pulsing as it was forced into Sarah's wet pussy. She was incredibly tight- his dick felt as if it was being squeezed in all directions, and as her pussy adjusted to his girth he felt her inner muscles ripple and convulse around his cock. For just a moment, there was silence, and then Tom and Sarah both exploded into a frantic pace of fucking. Sarah began to whimper as she bounced down upon Tom's cock. It was spearing deeply into her, forcing her pussy open and apart. Below her, Tom was thrusting hard upwards, matching her strokes and forcing every last inch of his throbbing dick into her before their hips slammed together. His hands were on his hips, pulling her down harder onto him, while her hands struggled to find a purchase on his shoulders or chest to stabilize herself while she continued to ride him.

Tom was becoming even more aggressive in his handling of her as he continued to thrust up into her. He moaned and began to grope at her tits through her sweater as she slammed down onto him. As he caught hold of one of her nipples and began to twist roughly through the fabric, Sarah's moans became progressively louder and her pussy began to convulse and spasm around his cock. Suddenly, she sat down heavily on him and her mouth formed an O. Her eyes shot open in wide surprise as an orgasm ripped through her. Her pussy convulsed around his cock as he flexed himself while buried within her. At that moment, it was Sarah's turn to lose control of herself; as she came down from her orgasm, she rose herself up off of Tom's soaked dick and turned around to face away from him. Now leaning forward so she was in the console section between the two front seats, She dropped her pussy back over Tom's throbbing cock and again felt it force her pussy wide open. Sarah was bent over nearly double as she began to bounce her hips up and down off of Tom's lap, swallowing his cock whole each time. Her sexy, voluptuous ass was now on full display for Tom, and he took full advantage as she rode him hard. With one hard smack of her ass, she began to scream in pleasure.

"FUCK! Tom that feels so fucking good!" Sarah yelled back to him as she continued to force her pussy down on his cock. "Give me every inch of that big beautiful dick! Pound my fucking pussy until I cum all over you! UNH! YES!" Sarah screamed and cried out each time Tom's hand made contact with her ass. "FUCK! Slap my fucking ass while you fuck that pussy! Stuff that whole thick cock into my dirty cunt! GOD, FUCK, YES, FUCKING, GOD YES!" Sarah screamed and came again. Tom could feel as her juices began to saturate his balls beneath her tight pussy. She continued to ride him through this orgasm, chanting the whole time. "Fuck that pussy, fuck that pussy, slam that dirty fucking pussy, give it to me, ah, give me that whole, ah, big cock up in my slutty fucking cunt! AHH!"

Tom began slamming into Sarah as fast as possible. The whole car rocked as they came together, and the car was filled with the sounds of their groans and the sound of impact as Tom's cock repeatedly filled Sarah completely. Sarah's juicy ass bounced off his lap and rippled just a bit as it rebounded- every time Tom slapped her ass, Sarah would groan and fuck herself down on his cock just a little harder. Her pussy was constantly convulsing around Tom's dick as she tried to impale herself even further with every thrust. Sarah was quickly ascending towards a massive orgasm, and her moans turned to screams as her pussy began to clamp down like a vise around Tom's cock. Suddenly she felt a new sensation from Tom's work on her ass, and it made her entire body wind even tighter as she approached her orgasm.

As Tom had stared at the beautiful sight of Sarah's round ass bouncing off of his cock, he had made another bold decision. He slapped his hand down on her ass so that where it rested, his thumb landed directly against her asshole. He pressed gently against her sphincter and felt its tight resistance, but it began to give way to his insistent pressure. He raised his free hand and brought it down hard across her bouncing ass, and as she moaned and slammed down extra hard against his cock, Tom's thumb popped into her ass and slid an inch deeper into her. The new invasion only made Sarah's pussy clamp tighter around him. Tom began working his thumb in and out of her ass while Sarah continued to ride his dick. The pressure of Sarah's tightening pussy, combined with the sound of her frenzied moans as she repeatedly took his cock deep inside her, was quickly making Tom approach his own orgasm. By the way his balls were tightening and beginning to churn, he could tell his impending climax was going to be a big one.

"UNH, Sarah, I'm going to cum!" Tom cried out as he continued to buck his hips upward to collide against her. His breathing became ragged as he felt every muscle in his body begin to tense. Sarah continued to bounce up and down on his cock, making the whole car shake. He continued to slide his thumb in and out of her ass while he stared at her. The sight of this pale beauty, with her back arched and her red hair bouncing across her shoulders with every thrust, was quickly becoming too much for Tom. "Sarah!" He called urgently as her pussy continued to engulf his cock. "What should I do? Where should I-"

"IN ME!" Sarah screamed as she continued to moan loudly. "FUCKING CUM IN ME! Fill me up with your- UNH- fucking cum! Ooooh Tom, I'm going, uh, to cum so fucking hard, just don't stop fucking me!" Sarah's whimpers and moans became even wilder and more animalistic as she rode hard towards her orgasm. She was throwing herself down upon Tom's cock now, fucking like a woman possessed. As Tom's cock began to swell even fuller, she felt her orgasm finally arise and she settled hard onto Tom's lap, feeling every bump and ridge of his cock as it slammed all the way into her.

With a loud, primal groan, Tom finally came hard. While buried inside of Sarah's tight pussy and feeling the slick walls spasm around his cock, Tom felt the beginnings of his sperm rocketing up his shaft. They came hard and together, bucking and spasming involuntarily while their hips were locked against one another. Over their orgasmic groans they could hear the sound of their combined juices overflowing from Sarah's pussy and saturating both of them. Tom's cock continued to pulse in orgasm and fill her full of his cum. She wouldn't typically have allowed that so impulsively, but now as she felt fuller than ever she felt a series of smaller orgasmic ripples emanate from her well fucked pussy.

Tom and Sarah remained locked together as they caught their breath. Tom's cock slowly began to soften inside Sarah as she remained bent forward over the center console. She turned to look behind her at Tom's exhausted expression and gave him a devilish grin. "Drive me back to your place, stud." She said, grinding her hips along Tom's and feeling his cock begin to stiffen inside her.

"You have a long night ahead of you."