Nerd's Reward Ch. 05

"Hey man, what's going on today?" Larry said.

"Hey, mate! You won't fucking believe this." Paul smiled widely. "That hot ass chick from the pool came back."

Larry quickly surveyed the poolside and finally found Jess. She was lying on her stomach and couldn't see him without turning over. At first, he was a little surprised that Nate's girlfriend would come back down to the pool and seek out Paul.

"Really?" Larry showed interest. "That's gotta make your day."

"Man, if you'd gotten here just a few minutes ago, you'd have seen me with a handful of that ass." Paul bragged.

Larry couldn't believe what he was hearing at first. But Jessica wasn't one to be very shy and with her boyfriend not around she seemed a little flirtier than usual. Quickly, Larry's scheming brain kicked in and he began to realize that if he could get Paul to get Jessica all worked up, maybe that would work to his advantage.

She certainly would turn his offer down, but if he could get Paul to take her out to dinner and get her all excited and then wasted she would fall right into his hands. He didn't think Jessica would cheat on Nate so he decided to go forward with his plan.

"Damn, that's sweet." Larry encouraged the boy. "I bet if you keep working your magic you could get her to go out with you tonight."

"Really? I was kinda planning to try something like that. I just hope she doesn't blow me off." Paul replied.

"Just give it a shot, pal. Nothing ventured, nothing gained. Just work her a bit more then spring the question." Larry said.

"Yeah, I'm gonna give it a shot." Paul said taking a drink.

"Good luck. I'm gonna grab me a drink then head up to my room." Larry said.

Paul grabbed the drinks and made his way back over to where Jessica was laying.

***

"Now where was I?" Paul said putting some lotion into his hands.

Jessica downed about half of her drink and lied her head back down.

"I don't think my behind will burn anytime soon." Jessica laughed.

Paul smiled at her comment and began to rub the lotion onto her legs. He started on Jessica's feet first. The sensation caused her to giggle slightly. She was ticklish after all. Paul continued gently rubbing her feet. Eventually, Jessica got used to it and began to really relax. Soon Paul was working his way up to her calves.

Jessica inhaled sharply once he reached the back of her knees. It was one of her most sensitive spots. Paul knew he had her where he wanted her so he began to firmly massage the back of Jessica's thighs. Before long his thumbs where gently pulling the cheeks of her ass apart.

"Umhh..." Jessica moaned.

Paul did his best to get a view of Jessica's pussy but he had to be very careful not to be too overt. Jessica was getting really turned on. She could feel her pussy getting wet as her toes curled uncontrollably.

She knew she had to stop the young man but she really didn't want to. After a few more seconds Paul felt Jessica's ass tense and he knew he'd gone a bit too far. Before she could say anything to ruin the mood Paul decided to spring the question.

"Hey, what do you think about dinner with me later tonight?" Paul smiled.

Over at the bar, Larry noticed that Paul wasn't rubbing lotion onto Jess anymore. They appeared to be talking. He knew that Jessica was going to turn Paul down because she thought she was going to dinner with her boyfriend. Quickly, Larry grabbed the nearest waiter and whispered something in his ear.

Jessica blushed slightly at the young man's offer. She really like Paul but she was committed and she knew that just by flirting with him she was on thin ice. She decided to be very sweet in turning him down. Besides, she might spend a little more time with him later in the week.

"That's really sweet of you, Paul, but..." Just then Jessica noticed someone approaching them.

"Excuse me?" A waiter interrupted. "Miss Gellar?"

"Yes?" Jessica answered.

"I am sorry to bother you, young lady." The waiter apologized. "But we have a message for you."

"Oh, thanks." Jessica took the note from the waiter and started reading it, as soon as he left.

"Sorry, Jess, I won't be able to make it later, I am winning this tournament and I am celebrating with the guys over here. I will make it up to you, I promise. Love, Nate." The note read.

"What?!?" Jessica said sitting up in her chair doing her best to hold her bikini top on with one arm.

She was fuming mad. All she wanted was to spend a romantic evening with her boyfriend, who made love to her better than she could remember. But if all he cared about was a game then he could play all the stupid game he wanted.

"That's fine." Jessica thought. I think I can find something to keep me busy tonight.

Covertly, Larry made his way back upstairs. He was confident he'd succeeded with his plan.

"On Second thought, Paul, I would love to have dinner with your tonight." Jessica smiled.

"Sweet!" Paul yelled.

"Give me an hour to get ready and I'll give you a call." Jessica said standing up.

"Will do, I'll see you in a bit, babe." Paul said standing up as well.

Paul wrapped his arms around Jessica and gave her a tight hug. Jessica was still holding her top on with one arm. Instinctively she wrapped both arms around Paul. After a few seconds the two separated slightly and when they did Jessica noticed Paul' eyes getting wider. Follow his eyes Jessica realized that her breasts were almost completely exposed.

"Whoops!" Jessica giggled.

As Jessica quickly tied her top back together something caught her eye. Paul had a sizable bulge in his shorts. Jessica felt flush and a grin formed on her lips.

"My, my, my." Jessica whispered to herself.

Eventually, she gathered her things and made her way back upstairs. When she got into her room, she stripped off her swimsuit and got into the shower. As she washed off, she began to get really pissed that her boyfriend had blatantly blown her off so he could play some damn game. She thought about calling him but she didn't want to get into a big fight on their vacation.

"I can't believe him." Jessica pouted.

Eventually, her anger disappeared and she began to realize that she didn't need her boyfriend to have a fun night on the town. Paul seemed to be more than willing to accompany her. After her shower, Jessica took her time getting ready to go out. She carefully did her hair and makeup. She knew she didn't have to try very hard to get Paul' attention, but he was such a nice boy that she thought she'd go the extra mile to make sure he had a hot date tonight.

After digging through her luggage for a while, Jessica decided on a very tight, strapless, sky blue dress that she'd worn several times before. It was one of her favorites because although it was tight, the material stretched enough so she could really move on the dance floor.

The only thing that gave her pause was the length of the dress. It was rather short. The bottom only came down just below her butt. She'd only worn the dress when she was out with her boyfriend, but tonight she'd have to be careful.

"I hope you are having fun, Nate." Jessica said to herself as she pulled her panties up under her dress.

After one last glance in the mirror Jessica picked up her cell and dialed Paul' number. She'd be lying to herself if she said she wasn't nervous. She was calling a younger man to take her out on the town. The naughtiness did give her a slight thrill but she knew she could keep things under control.

"Hello?" A voice said after a couple rings.

"Paul? Hey this is Jessica. I'm ready whenever you are." Jessica said.

"Cool. I'll be there in five minutes. Meet me out front." Paul replied.

Jessica hung up and grabbed her purse. Across the hall, Larry was waiting by his door. He was waiting to hear her door close so he would know about when to put his plan into motion. After hearing his buddy's girlfriend's door open, Larry looked through his peephole.

He was treated to the vision of his friend's beautiful girl, all dolled up, as she walked away. Larry took notice of Jess' choice of what to wear out with Paul. She didn't look overly slutty, but she'd be sure to get a few glances. Satisfied that everything was going according to plan, Larry laid back down to watch a movie. The way Jess partied, he knew he had plenty of time.

Paul was pulling up to the front of the hotel when he saw his date for the evening. He shook his head with a huge grin on his face. Jessica was standing patiently by the curb and she looked great to the young man.

"No turning back now." Jessica thought to herself as she spotted Paul in an old Taurus.

"Need a lift pretty lady?" Paul smiled.

"My hero." Jessica replied as she got into Paul' car.

As they drove, Paul kept staring at Jessica's legs. He could hardly keep his mind on the road. Jessica thought the way he was acting was so cute.

"I'm not just saying this, but you look beautiful." Paul said.

"Why thank you." Jessica replied blushing heavily.

Without really thinking, Jessica covertly stole a glance at Paul' lap, but quickly scolded herself for even thinking about it. She wasn't even at the club yet but the sexual tension was high already. Tonight she was going to have to be very careful or she could easily do something she would regret.

When they eventually got to the club they saw that there was quite a long line at the front door. After parking, Paul and Jessica made their way to the back of the line.

"Well, we might be here a while." Paul smiled.

"Oh well, I'm patient." Jessica said.

"Good thing I brought something to pass the time." Paul said reaching into his pocket.

Jessica smile as Paul pulled a flask out of his pocket and took a drink. Jessica took a drink as well and the two began talking to pass the time. After a while, the flask was bone dry and Jessica was giggling uncontrollably as she talked to her young friend. Her resolve was starting to fade as the night went on. Combined with the alcohol, Paul's charm was starting to weaken Jessica's restraint.

As the line gradually moved, Paul started to slowly make body contact with Jessica. A gently touch here and there, just testing the waters. Jessica was all too aware of what Paul was doing and thought it was very sweet that he was being such a gentleman. Wanting to let him know she was ok with what he was doing Jessica grabbed Paul's arm and put it around her waist.

Paul smiled and the two continued talking as they inched closer to the door. Jessica was in mid-sentence when she felt Paul' hand slip down from her hip to her ass. She just smiled and continued talking. Soon though she couldn't really ignore what Paul was doing.

He was gently squeezing her ass. She didn't know if it was the alcohol or not but she didn't think there was anything terribly wrong with what he was doing. After all, they were on a date. It was almost standard procedure.

"You're the hottest woman here." Paul said half drunkenly.

"Flattery will get you everywhere." Jessica giggled.

Just as they were getting close to the front of the line Jessica gasped as she felt Paul's hand drop to the back of her exposed thigh. The short length of her dress made it easy access for her daring date. Before she could say anything Paul's hand was massaging her inner thigh with his thumb just inches away from her pussy. As Jessica turned her head to say something, Paul leaned in and kissed her.

Jessica's eyes opened wide and she inhaled sharply as Paul's lips touched hers. This kiss wasn't rushed or rough, it was gentle and if she was going to be honest, it was perfect. As they kissed, Jessica was relieved that Paul's hands were now around her waist. She knew she'd crossed a line but she was still convinced she could control the situation.

Paul broke the kiss and stared into Jessica's eyes.

"I'm sorry." Paul said. "I just couldn't wait any longer."

"It's okay." Jessica said not believing what she'd allowed to happen. "It's just that I have a boyfriend and I am upset with him right now."

"Good, because I think you're just about the most beautiful woman I've ever seen and I wouldn't want to do anything you didn't want me to." Paul said.

"Paul, I really like you to but you've got to..."

Before Jessica could reply Paul kissed her again. This time, in the heat of the moment, Jessica didn't fight at all. In fact, she did something she didn't expect herself to. Her lips parted slightly and her tongue quickly darted into Paul's mouth. Jessica's heart was racing and she could feel Paul's hard cock pressing into her abdomen. Just as she was about to lose control a deep voice interrupted their moment.

"Alright you two, break it up and get inside or get to the back of the line." A particularly large bouncer said.

Jessica smiled at Paul and they made their way inside. Before she did something, she knew she'd regret Jessica excused herself to the bathroom to calm down a bit.

"Oh, my god!" Jessica said looking at herself in the mirror. "What in the hell was I thinking?"

She knew she had to slow herself down a bit. It was one thing to have some fun but she wasn't about to cheat on her boyfriend, no matter how ticked off at him she was. Jessica looked around to make sure she was alone in the bathroom before pulling up the front of her dress.

"No surprise there." Jessica said as she looked at her completely soaked panties.

Eventually, Jessica convinced herself that as long as all that she let Paul do was feel her up a bit and occasionally kiss her, she wasn't cheating, she was just having fun.

Back at the hotel, Larry had already managed to hack the lock device and get into Nate's room. He casually pulled the sheets down on the bed and sat down. His mind was really starting to wonder. He knew that in a few hours there was a very good chance that he'd be fucking Jess again. Tonight, he was going to take his time though. He was going to enjoy what might be his final opportunity.

At the club, Jessica and Paul were on the dance floor having a great time. They danced for almost an hour straight and Jessica was glad to see that her date was a very good dancer. They danced close and grinded each other like they'd known each other for years. Finally they went to the bar to rest and cool off a bit. They were both covered in sweat.

"You're a very good dancer." Jessica said to Paul.

"Thanks." Paul smiled. "You are not bad yourself."

As the minutes wore on the two went through quite a few drinks. Before long, both Jessica and Paul were, to put it lightly, trashed.

"Hey lets go sit down at a table, my feet hurt." Jessica said thinking of an excuse before she fell off her bar stool.

Jessica spotted a table in a back corner and dragged her stumbling date behind her. Once they got to the table, Jessica helped Paul sit down. But, before she could get to her chair, Paul grabbed Jessica by the arm and pulled her onto his lap. Jessica smiled and wrapped her arms around Paul's neck to steady herself.

"God, you look so good." Paul slurred with a grin.

Jessica smiled, both at Paul's comment, and the trouble he had getting the words out.

"Thank you baby, you're not too bad looking yourself." Jessica replied.

As Jessica sat there on Paul's lap she looked around the club at all the people dancing and having a good time. Although she was having a great time with Paul, part of her wished her boyfriend was there with her. Her thoughts were interrupted when she felt Paul's hand on her bare thigh. She decided not to do anything; Paul could have his fun for now.

Minutes later Jessica realized that her sitting on Paul' lap was having another effect that she should've seen coming. She could feel Paul' cock starting to grow under her ass. Jessica couldn't really blame the poor kid.

"Hey babe, I could use a refill, how about you?" Jessica asked trying to think of a way of getting off Paul's lap.

"I could use a refill of this..." Paul said as he pulled Jessica's head towards his.

They kissed for a few seconds and Jessica was alright with it as long as nothing else happened. Paul sucked Jessica's tongue into his mouth and really started going to town. After a minute or so Jessica was breathing really heavily and she was almost lost in the moment. She could feel the warm tingle between her legs that let her know she was very turned on.

"Paul ... Uhhh..." Jessica tried to stop herself unsuccessfully. "Ohhh ... Ummmmm..."

Alarmingly, Jessica felt Paul' hand slide up her thigh. Thankfully her legs were crossed because Jessica didn't think Paul would've stopped.

Paul started to kiss his way down Jessica's neck as he squeezed her thigh. Jessica stared at the lights on the ceiling as Paul's head went ever lower until his tongue tasted the flesh between her tits.

"Ohhh ... Fuck!" Jessica groaned as Paul nibbled on her cleavage.

In her drunken state, Jessica's resolve had greatly weakened. Thoughts of her boyfriend were nowhere to be found. Paul wrapped his arm around Jessica's back and he used his free hand to cup one of Jessica's tits tightly. Jessica leaned in and kissed Paul as he fondled her breasts. She knew she was in dangerous territory but she didn't care at the moment.

The two made out heavily for a few minutes until Jessica shifted her position on Paul's lap a little. When she did, she unknowingly uncrossed her legs. It didn't take Paul long at all to seize the opportunity. He quickly slid his hand under Jessica's dress.

"Ummmmmm..." Jessica moaned as Paul' index finger made contact with her panty covered pussy. "Ohhh! Hmmmmmmm..."

Jessica's mind was screaming at her to stop what was happening but her body was on fire. She hungrily bit Paul's bottom lip as her fingernails dug into his back.

"Oh, God!" Jessica moaned as Paul pulled the front of her panties to the side.

Jessica was lost in her desire as her tongue hungrily explored Paul's mouth. Paul slowly rubbed Jessica's soaking pussy before slipping his middle finger inside.

"Ohhhhhhh..." Jessica groaned. "Fuck!"

Jessica knew she'd crossed the line by letting Paul finger her but she was too caught up in the moment to stop. She clenched her thighs around Paul's hand as his fingers explored her. He began using his thumb to rub Jessica's clit while his index and middle finger dug as deep as they could. Jessica's ass ground into Paul' lap as the young man brought her closer to her goal.

"God, that feels so good!." Jessica hissed as she bit her bottom lip.

Jessica began to breathe very quickly and the warmth coming from her pussy let her know she was almost there.

"Oh ... Oh, fuck!" Jessica groaned as her pussy clenched around Paul' fingers. "Gawd, I'm cumming!"

Jessica shook uncontrollably on Paul's lap as she came. She smiled as the euphoric feeling washed over her. She was sitting on a young man's lap in the middle of a crowed club and had just came very hard. The line Jessica feared she'd cross was very far behind her now.

"Ohhhhh!" Jessica yelped as Paul removed his fingers from her sensitive pussy.

"Well, I think it's my turn now." Paul smiled.

Jessica didn't know what to say at all. She'd just for all intents and purposes cheated on her boyfriend. Now Paul wanted her to return the favor he'd just given her. Jessica's mind was full of all kinds of thoughts and she didn't know what she should do next.

"Paul ... what you did felt ... it was ... wonderful but..." Jessica trailed off.

Paul stared at the woman sitting on his lap he'd just finger fucked. He didn't know why she seemed so reluctant to go any farther but he didn't' want to ruin his chances of fucking her.

"It's alright, babe. Hey look ... If things are moving a little too fast for you we can chill for tonight." Paul said.

Jessica felt very relieved that Paul seemed to be letting her off the hook. She felt guilty that he'd gotten her off and now she was leaving him holding his dick so to speak, but she couldn't have sex with him. She was committed and she'd crossed a line she didn't think she ever would.