Betting for Love

[musicankane]

Jake didn't want to go to parties, he wasn't a very social person. But his friend Matt was, and upon his insistance Jake found himself at Gamma Gamma Gamma house for their monthly bash. The place was packed as usual, GGG house was once of the biggest on campus and why not? The Frat had the hottest chicks and most popular of the student body.

Shortly after they arrived Matt predictably darted to the keg and then out to mingle with whatever ladies would talk to him. Jake was left to find his own entertainment. He had thought about just showing up with Matt, and then leaving as soon as MAtt left him alone. But Matt often drank far too much too quickly and Jake needed to make sure that he stuck around in order to get Matt home should he need it.

Jake got himself a drink and found himself a spot on the back porch in order to watch the people swimming and hanging out around the pool. Little did he know that as he watched people he didn't know, someone else was watching him.

* * * * * *

Michelle nudged her friend Jessica and pointed to the geek standing on the padio. "How about him? He'd be perfect for you."

Jessica shook her head. "Come on, you have to give me something to work with Michelle."

Michelle smiled, "Hey a bet is a bet Jessica. Besides if I gave you a guy that you actually might enjoy yourself with then it wouldn't be fun for me. You can always back out and give me the hundred bucks now. I'll only rub it in your face for the rest of the school year."

Michelle turned and smirked, "God look at those glasses. Come on Jessica back out or go do it." She gave her friend an evil evil grin.

 

[princesssexci]

It all started with a bet. Jessica assumed it would be a simple bet, fuck a nerd and get paid. After all, how hard could it be to get a nerd to have sex with her? After all, what nerdy guy wouldn't want to fuck her? She was the sorority president of Delta Gama Nu and had fucked most of the jocks on campus. Most of them, not all of them. She wasn't a slut but she wasn't pure either.

Her best friend Michelle had suggested that she have sex with someone who wasn't so high on the popularity ladder. In fact, to make it more enjoyable for Jessica; Michelle offered to pay her 100 bucks. Now, here they were at the GGG party surveying the men there. Plenty of jocks to choose from and Jessica had NO problem fucking a jock.

The president of the GGG grinned at her, winking. As if Michelle could sense her thoughts, she nudged Jess and shook her head.

"How about him? He'd be perfect for you."


Jessica sighed and looked over towards the patio. Jake, of all the guys to choose from, Jake had to be Michelle's first choice. He was the most awkward person in the universe. She shuddered, he'd probably slobber all over her body. He probably didn't even have the finesse to fuck her properly.

She groaned out of displeasure, "Come on, you have to give me something to work with Michelle."

"Hey a bet is a bet Jessica. Besides if I gave you a guy that you actually might enjoy yourself with then it wouldn't be fun for me. You can always back out and give me the hundred bucks now. I'll only rub it in your face for the rest of the school year." then she continued, "God look at those glasses. Come on Jessica back out or go do it."


Jessica groaned oonce more and sighed. There was no way in hell she was paying Michelle a penny. "Fine, should be a piece of cake." She pulled her black slinky dress down further so that her breasts popped out. She wasn't wearing a bra that night assuming she'd be fucking someone worth not wearing a bra for. Her nipples lightly poked against the silk fabric. The dress fit her body perfectly, showing off all her curves, her round tight ass.

She went to the kitchen and grabbed a beer for both her and Jake and then made her way outside, hips swaying as she walked.Tapping Jake on the shoulder, she smiled offering the second beer in her hand "Hey there. You looked kinda lonely out here? Mind if I join you? Sometimes, it's nice getting away from the crowd."

 

[musicankane]

Jake was used to being ignored and left to his own thoughts at parties like this. He wasn't a popular guy, maybe a result from too much Magic the Gathering and D&D in high school but he wasn't a complete tard either. Some nerds he had met had absolutely no idea how to act in the world and thus they sheltered themselves. Jake had earned that picture from others because he stayed back, but he was rather articulate when he wanted to be. He had the highest IQ in his high school, he had memorized Shakespear's Romeo and Juliet for drama class.

When he felt a touch on his shoulder he turned, thinking it would be Matt trying to get him to do something. His eyes widened when he saw a beautiful girl holding out a beer for him. She smiled and he fought very hard not to let his eyes drift down to her breasts as they nearly heaved out of her dress.

She asked if she could join him and pushed the beer into his hand. He opened his mouth to speak but the only thing that came out was a croak. He closed his eyes and cleared his throat. Way to fucking blow it Jake. Not even a hello and you're already screwed.

He shook his head and turned back toward the railing. "I'm sorry. I wasn't expecting....I thought you were someone else." He gestured to the railing beside him, "Feel free to join me. I'm watching a game a drunken marco polo in the pool." He told her, still kicking himself for that embarassing noise he had made.

 

[princesssexci]

Jessica had to hide the pure amusement she had for Jake. It was kinda sad. She felt for the guy. He had no confidence whatsoever when it came to girls. This was going to be so easy. She took a sip of her own beer and looked over the railing of the patio to watch the drunken marco polo game.

She was silent for a moment contemplating a way turn this situation around. "How fun!" She said, faking enthusiasm in her voice. "Who do you think is going toi win?" She took another sip of her beer as she listened to what he had to say. Silently she thought to herself how lame this was and how he seriously needed to get with the program.

There was another patch of silence. Jessica wrinkled her nose in thought and then turned to Jake again,"Hey, why don't we go inside? They're playing one of my favorite songs and I've been aching to dance all night." Seeing his hesitation, she forced another smile, "It'll be fun, please?" She pouted.

http://cdn2.screenjunkies.com/wp-content/uploads/2011/03/megan-fox-sexy-cleavage.jpg

 

[musicankane]

Jake turned toward her and glanced at her body up and down. She was being so unusually forward. Girl's didn't talk to him like this, not hot girls, and not wanting to do things with him. He turned and glanced inside, there were plenty of guys just hanging out, cooler than he was and they'd all be willing to dance with this amazing beauty.

So why him?

He swallowed and turned back to her, her eyes looking up at his. Her hauntingly beautiful eyes, as if waiting for him to respond and give her an answer. His heart beat heavy in his chest.

"Dance? Well, I uh..." He didn't know what to say. "Okay." He said, stupid to say no. For some reason she had choosen to talk to him, he would be a fool to toss it away. "I'm Jake." He said holding out his hand.

 

[princesssexci]

Jessica grinned, bingo. What guy could tell her no? None. Yeah, she could easily dance with the jocks or frat guys but where was the fun in that? Plus Mich wasnt paying her to have sex with someone like that cutie Matt.

"Jessica." she said, taking his hand and leading him to the dance floor. The song playing was appropriate, it was Break Your Heart by Taio Cruz feat. Ludacris. Her hips swayed to the fast paced music. Her ass would lightly brush against his. This was a purposeful act but Jess made it seem like it was on accident. It was sn easy task since the dance floor was pretty crowded, anyways.

After the song, Jess turned to Jake with a bright smile," Wow, you're real good." Another song came on it was slower, with a more seductive tone. Her hips swayed to the beat once more, reaching for his hands she brought them to her hips. standing on her tip toes Jess whispered in his ear , " Don't be scared. I won't bite....unless you ask." Her hot breath caressed his ear and hands were placed on his shoulders.

They roamed up and down his chest.

 

[musicankane]

As they began to move to the music, Jake began to relax a little bit. He was embarrassed to dance in front of all these people, but he realized that nobody was going to judge him when he was clearly dancing with such a hottie. She bumped against him as they moved, her hips bumping into his, her ass casually rubbing across his groin. It was very exciting and Jake found it difficult to keep from getting completely hard in his pants.

Then the music changed and they came together in a slow dance. His mother had taught him how to dance when he was just a little kid and it was something he actually remembered how to do. His hands went to her hips and he held her as they swayed. Jessica's hands roamed up and down his chest gently, her perfume began to make him feel wonderful.

It occured to him that this was his first dance with a woman since his high school prom where Becky Larson had taken his virginity. She said it was his reward for being such a nice guy through the years and a pretty decent dancer. She said that, but he knew it was a pitty fuck. Becky was always saying that he couldn't go to college a virgin, she urged him to talk to other girls throughout high school. Nothing ever worked out so she took matters into her own hands.

Now here he was with another chance, but he wondered if she was here because of pity. Maybe Jessica had felt bad for him, being alone at a party and decided to talk to him because she felt sorry for him.

AS they swayed he asked her, "So what made you come out and bring a random guy a beer? Just wanted me to dance with you?" He asked with a gentle smile.

 

[princesssexci]

Jessica was actually kind of surprised that he was a good slow dancer. She hadn't expected that. In fact, she expected him to step on her feet or something. He didn't though. Glancing around the room, she saw Michelle in the corner watching while stuffing her face with potato chips. She normally did that when no one would ask her to dance. She was a binge eater. Jessica kept telling her she'd end up being fat again.

Jake's question slightly startled her because well, she wasn't expecting him to ask her the whys of talking to him. What nerd actually cared why Jessica talked to them. Well, since she rarely talked to nerds, there was no reason to ask that question. Of course, that was the whole point! Why care when you could miss an opportunity of even being associated with Jessica.

She decided to play on his last question though, "Of course! Think of it as an...initiation. You know like in frats or sororities? When I see someone new I always ask them to dance, just to see if they are good dancers or not." She lied as she grinned at him, "Don't worry, you pass."

 

[musicankane]

Jake gave her a funny look. Initiation? What did that mean? Initiation for what? He was already part of a frat, he had joined up with the Beta Cappa Pi's his first week of school. Mostly because that building had the best Wi'Fi on campus and Jake liked his online video games.

"Initiation?" He asked her with a puzzled tone. He opened his mouth to say something else but finally for the first time in male history his brain and penis cried out for him to shut up at the same time and he did.

Jessica was beautiful, her hips warming his palms. Did it really matter why she was here, she was incredible and way out of his league. If for whatever reason she had an interest in him that could get him a girlfriend then he was down for it. Jessica was the kind of girl he pictured as his girlfriend, though he never thought it would actually happen.

 

[princesssexci]

As he questioned her for a moment, internally Jessica freaked out. Maybe initiation was the wrong kind of word. It made him seem like he was not worthy. Well, he wasn't but she was supposed to be charming the pants off of him...literally! And then ding ding ding, a sudden brilliant idea came to mind. Jake hadn't pushed the question any further but just so it wouldn't look rude, she continued smiling at him.

"Yes, initiation." She said, still trying to think of how to say it without sounding offensive.

Lying seemed to work for her tonight. "Well, you do know that most women judge how good a guy is in bed, by the way he dances right?" One of her hands which had been caressing his chest moved over to his bicep and lightly trailed a finger up and down it.

She licked her lips slowly and seductively at Jake, "So far I think you'd probably be a decent lover." Most girls liked to be subtle about sex, Jessica wasn't the subtle kind of girl. Besides, most guys were really bad at subtle hints (she did alot of that in highschool) so, she figured being straight up and honest worked well for her. She stood on her tip toes again so that her breath would brush against his ear when she said, "Maybe we can find out?"

 

[musicankane]

Jake gasped as her words breathed across his ear. Suddenly the heat of her body against his became intense and his body began to respond. He couldn't believe this was happening. He was actually getting picked up by a beautiful girl for the purpose of sex. He mentally hoped that the condom in his wallet was not beyond the expiration date.

He stepped back from her just enough to look into her eyes, "Are you serious?" He asked with a trembling voice. "This isn't some joke is it? I mean nobody has ever tried to umm, take me to bed I guess." He was stammering and his brain and especially his cock were screaming for him to shut the fuck up.

His fingers tensed slightly on her hips, as if he could hold her against him if she tried to pull away.

 

[princesssexci]

Jessica couldn't help but giggle. His geekiness was kind of cute in a way. It was like talking to a virgin. It made her wonder if he actually was a virgin. She slowly nodded and her smile widened as his hands grasped onto her hips in an almost possessive manner; or maybe it was a 'please don't go manner'. "Very." she said in answer to Jake's question about whether she was serious.

"Well, this girl is.." She said, their bodies still moved in tempo with the slow music. In the corner of her eye, she could see Michelle sulking because it was so obvious that she was going to win this bet. "Besides, I don't need to joke about sex.." the underlying words, 'I can have sex with any guy at this party' was there but trying to stay the charming flirt, she held back that obvious fact.

"Although, if you really don't want to--" she cut off her sentence and faked an alarmed look, "Oh my god! You have a girlfriend, don't you? That's obviously why you're so surprised. I mean, why else would a good looking guy like yourself be shocked that a girl is coming onto you." She sighed, looking rejected. Her eyes lowered in a pitiful look of sadness. Jessica attempted to pull away from him but not because she wanted to look like she was rejecting him, but the other way around.

 

[musicankane]

Good looking? He was good looking? There was no way he was good looking, not to someone like her, or was he? Jake had never been impressed with what he saw in the mirror every morning, but maybe it was because he wasn't a woman. Maybe girls saw him differently.

Could Jessica really find him attractive? It was such a foreign concept to him it caught him off guard. "No I, Jessica, I'm not dating anyone." He told her, urging her back against him. He smiled, "I'm sorry you caught me so off-guard. I've never had someone as beautiful as you show any interest in me."

He smiled and shrugged, "Why don't we get out of here and get to know each other." He suggested, his body on fire with the potential awesomeness of what could happen tonight. He knew he should be here for Matt, but this kind of thing never happened to him, so Matt would understand.

 

[princesssexci]

Hook, line, sinker! Did people really call nerds the smart ones? Really? Cause she just totally fooled one into thinking she was actually into him. She was 90 percent towards winning this bet and it didn't even take her an hour. Obviously, he'd never had someone of Jessica's beauty show any interest. In Jessie's world, she was the personification of beauty. Again, she feigned a look of shock and then blushed, lowering her eyes demurely.

"I..gee thanks. I mean, I'm flattered. I'm not that pretty." And now came her act of humbleness. Her eyes brightened and she smiled, "I'd love to go somewhere to...get to know you." She smiled. Instead of taking the lead this time, she allowed him to take her wherever he saw fit. She hoped that would be his bedroom.

She just wanted to get this over with, so she could get paid. Most girls would probably feel bad about what they were doing, but honestly..those feelings only happened in those cheesy romance movies or crappy romance novels. "Lead the way.."

 

[musicankane]

Jake was lost in his sexual desire to care about anything else. It had been too long since he had gotten laid and that was only the one time. She would be his second if he played his cards right. The question was, could he seal the deal?

He took her back to his dormroom and shut the door behind them. He clicked his desktop lamp on a low setting so it would cast a semi somatic light across the room. He turned to her and smiled, "I have dreamt of bringing a girl as incredibly beautiful as you here one day. I can't believe it is actually happening."

He didn't know quite what to do next. He stepped up to her and put his hands on her hips. "Now that I got you here, what should I do with you?" He teased.

 

[princesssexci]

Making it to Jake's dorm room didn't take too long. In fact, they got there a lot quicker than she had anticipated. She glanced around his dorm thinking that she was about 95% to the point of winning this bet. All she needed to do was get him naked and...

His words cut off her thoughts, she had to fight the urge to roll her eyes as once more told her he wasn't used to having girls as pretty as her. Well, duh! Slowly she walked towards him, like a cougar preparing to capture her prey. "Hm, what to do, what to do." She murmured, slowly smiling at Jake.

Her arms wrapped around his neck, "I can think of a few things to start off with." Jessica pulled Jake in for a long kiss while pushing him towards his bed until he collapsed there. Straddling him, Jess leaned down and began kissing him once more. Her tongue intermingled with his, gently caressing the inside of his mouth and brushing against his tongue. Her hands roamed down his biceps, moved towards his chest, then down a bit lower until they found the hem of his shirt.

 

[musicankane]

Jake now had no doubt that he was going to have sex tonight. The way she grabbed him and kissed him, her mouth seemed to invade his with a sweet taste. Her tongue probbed him and it was wonderful. He grunted as he bounced onto his back on the bed, only to have Jessica climb on top of him and kiss him again.

Her hips worked on his crotch, her body rubbing his cock through his pants. He tried to keep his cool, kissing her back as her hands roamed his body. She found the hem of his shirt and tugged it over his head. He grunted and threw the shirt into the corner.

His eyes met hers and he wondered if she could see the hunger within him. The hunger that had built up so much that it was scary to be let loose all at once. He sat up, forcing her to sit in his lap. His fingers grabbed the shoulder straps of her dress and yanked them to the side to tug her top down enough to free her firm, pert, breasts.

 

[princesssexci]

For the rest of the time here, instead of allowing herself to think; she let her body take over. Her eyes roamed over his chest as he pushed her black dress straps down. Her perky breasts bounced with the sudden force. Jessica only stood for a second to push her dress all the way down until there was nothing on her body except a black, sparkly thong.

She didn't wear a bra to the party because in instances like these where she was with a guy and didn't need a bra to get in the way. Since he was already sitting up, she undid his pants and pushed them down, along with his boxers. "I'm gonna rock your world, tonight." she said, before flicking her tongue over the head of his cock.

Her tongue glided along the base of his cock, then swirled around it. She did this a couple of times, before taking the tip in her mouth and sucking gently. Jessica began taking more and more in her mouth, inch by inch. Her hands reached lower to play with his balls and massage them.

 

[musicankane]

Jake had only a minute to admire her body as she dropped her dress. Jessica seemed to want to get to the action as quickly as he did. She jerked his pants down and his semi-hard cock sprang free. He wondered what she thought of him, his size was nothing impressive, but maybe it might be nice to her.

She dropped to her knees and took his cock into her mouth with the claim of rocking his world. Her tongue flicked around his tip and his cock throbbed to full mast in her mouth. He gasped as she sunk him into her mouth, playing with him and rubbing him with her tongue.

He sighed and let her give him wonderful sensations. Jake reached down and ran a hand through her soft hair, caressing her. "That's amazing." He told her, "I can't believe this is happening you are so incredible."

* * * *

Michelle watched Jessica leave with that geek and pulled out her phone. She had to stop her before she actually went through with it. She never thought Jessica would actually go through with fucking a geek just for a bet.

She sent the message only to hear Jessica's phone beep in her bag that had been left on a table. Michelle took out Jessica's phone and deleted the message. She frowned and wished she knew that guy's name, if she could get there she could stop Jessica from making a mistake.

 

[princesssexci]

Jessica had seen bigger cocks before, but his wasn't so bad. It was actually the perfect size. It wasn't so big that it couldn't fit all the way in her mouth, but it wasn't so small that it would only take a few seconds to get it all the way in. She groaned against him as his hands brushed through her hair as she took another two inches in her mouth.

She could feel it throbbing in her mouth and god did she love that sensation. As she took it a bit further, it sliding down her throat. Her throat constricted around the cock. Jessica pulled back and then slid her mouth forward, she did this several times.

His moans of encouragement only spurned her on to keep going. She pulled back from his cock with a loud resounding 'pop' and moved her head down to suck on his balls. Just as Jessica had done with his length, her tongue circled around the balls and then she began sucking gently.

Meanwhile, her hands stroked it, enjoying the girthy feel of it.

 

[musicankane]

Jake felt her throat around him, her soft warm flesh surrounding him, her spit running down his balls. She moaned for him, savioring his shaft in her mouth. It was like she was worshipping him, the way she took such care with how she moved her mouth around him.

Then she moved her focus to his balls, taking them very gently into her mouth, while her fist pumped his shaft. It felt wonderful, everything she did was wonderful. His shaft throbbing in her hand and his tip began to ooze his pre-cum.

HE remembered the condom in his wallet, he should try and get it. Even if it had expired from age, he should try for it. He grunted as she gave his balls a solid suck. "Jessica, I have a condom.....In my wallet." He panted, his body trembling with further need.

 

[princesssexci]

So caught up in her own lust, it was almost as if she didn't hear him. Her finger swiped against the head and Jessica's mouth released his balls as she licked the pre cum off her finger. Jessica had heard his request though. Shaking her head, she slowly stood up and straddled him once more.

"I don't like using condoms. Don't worry, I'm on the pill." Jessica said, attempting to relax him. She grabbed his cock again and gently guided it to the soft opening of her pussy. "I want to fuck you, now" She rubbed the tip against the opening before slowly lowering herself down on his cock with a loud moan.

Slowly, she began bouncing up and down in his lap. Her breasts bounced in rhythm. God, he felt so good inside of her. "Oh god...so..good.." she whimpered as her pussy tightened around his cock while also sucking him in deeper with every bounce that she made.

 

[musicankane]

Jake couldn't believe she was letting him inside of her bareback. Pill or no pill she didn't know him, but yet she was letting him have her in the most intimate of ways. When she sank down on his cock his eyes watched her face contort in pleasure as she filled herself with him.

He had forgotten what it felt like inside of a girl. She walls, hot, tight and soft all seemed like a caressing sleeve as he pushed up into her. Jessica didn't wait for her body to adjust to him, no sooner than her hips pressed against his did she rise up and down, fucking him with soft moans.

Jake put his arms around her and held her body against his, feeling her breasts rub against his chest as she pumped her hips up and down his cock. His cock throbbed and pulsed inside of her, and he gritted his teeth to keep from cumming. He wasn't about to let this end early because he couldn't hold his eruption back. But when he popped he could feel that it was going to be epic.

 

[princesssexci]

Wow. He felt really good. Jess was surprised. The fact that he was putting in some effort and that he was actually touchig her helped too. Most guys liked to just lay there and llet her do all the work. Her back arched in pleasure. The deeper his cock pushed into her, the better it felt.

Her body tingled with pleasure.She began bouncing faster then feeling his cock pulse even ore so inside of her, she bit her lip and forced herself to calm down. Jessica slowed down some, keeping their speed at a moderate pace.

As she rode him, Jess leaned forward and kissed him. Her nipples grew hard from the stimulation of rubbing against his chest. She was trying to keep herself from coming because she found herself enjoying it more when she and her lover for the night came together.

 

[musicankane]

Suddenly they were really into it. Letting themselves enjoy the sex, the feel of their bodies together. His shaft so deep inside of her even as she rocked in his lap. Jake was in heaven, the way her body rubbed against him. Her breath against his lips, it was all he had imagined it could be.

After a moment he pushed her back up on him. He lifted her off of him and gently flipped her onto her back on the bed. He stood over here and smiled, "My turn."

He climbed over her on the bed looking into her eyes as he got back into position. His lips met hers as he once again slid into her. Her body had gotten tighter from his absence. But it was wonderful to open her up again.