Larry Higgs awoke with a huge grin on his face. He lay there for a while just reflecting on the week's outcome. Eventually, Larry came to a couple of realizations. First, he had a sudden boost of confidence, literally overnight, due to a case of mistaken identity. He managed to fuck the hottest girl from school, Jessica, who just happen to be his pal's girlfriend as well.
Second, thanks to her propensity for drinking too much, he pushed his luck and got her between the sheets once more, this time right in front of her sleeping boyfriend. Those two events alone would be more than a former virgin nerd like him could ever ask for, but there was more; he nailed two more gorgeous older women as well: Sue, who is a guest at the hotel and the hot wife of a pompous asshole, and his big-breasted school counselor, Keira.
Larry finally learned about compensation; he lacked the appeal, and certainly his dork, pale, skinny looks weren't the sexiest things around. Still, he knew that he packed a huge cock, one that seemed to have quite an effect on all those ladies he met. The naive geek was becoming something else and he could notice the changes.
As he lay there, with his arms above his head, Larry began to think about last night's events. He went further and scored another hot session of raw sex with his pal's hot girlfriend once again, without her even knowing it had happened.
"I just can't believe it. I fucked her! I fucked the shit out of her!" Larry smiled. "Damn! Who will believe me?"
***
Next room, Jessica was coming to herself. Like her boyfriend's scrawny buddy, she also smiled widely. As she stretched, Jess felt a deep soreness between her legs. Last night was the best sex she'd had in a very long while. She glanced over at her boyfriend, Nate, who was still dead to the world.
"Hmmm ... that's odd." Jessica thought noticing that Nate still had his shirt and underwear on. "Nate must have felt cold."
She could've sworn that last night her boyfriend was naked after they'd had sex. After a few minutes Jessica chalked up her foggy memory to the insane amount of alcohol she drank last night. Soon, Jessica was up and showering the night's funk away.
Looking forward to a day with her boyfriend and friends, Jessica sang softly to herself as she washed. She was very satisfied with her vacation so far. The young stud at the pool, who flirted with her, the night out dancing, and some seriously good sex topped off a wonderful week.
Nate finally came too and was thankful that he'd made it to his own bed. He was a bit surprised that he still had on all his clothes but his pants were around his ankles. He was still scratching his head when his girlfriend came out of the shower with a nothing but a towel wrapped around her hair.
"Good morning, stud." Jessica said kissing her boyfriend on the forehead.
"Morning." Nate mumbled.
"Hey, I was thinking that you and I could spend the day together, here. I could really use some cuddling." Jessica asked as she put on her panties. "What do you think?"
"Yeah, I guess so..." Nate yawned. "We'll see..."
Jessica was surprised by her boyfriend's sudden lack of interest in her. Last night was the hottest they've been for each other in years and now he wasn't giving her a second look.
"Maybe he's just hung over..." Jessica thought.
*** 20 hours earlier ***
Larry got dressed and left the locker room. He had created a lame excuse, solely to get in his hot teacher's pants and that actually worked. During the trip's few days, he managed to get more sex than what he got in his entire life, which was none, as a matter of fact.
"Hey, man!" Larry was brought back from his reveries by his friend. "Where the hell have you been?"
"I-I was, uh ... J-Just ... I mean..." Larry tried to think of something to say. Somehow, telling his friend he was shoving his big, fat cock up their counselor's tight little pussy didn't sound very believable.
"Never mind!" Nathan got tired of his friend's babbling. "I am grabbing breakfast for me and Jess, could you tell her I will be right back?"
"Huh, sure." Larry agreed. "I was on my way up, anyway."
"Thanks." Nathan said turning to leave. "You are quite a pal."
"No problem, Nate." A week ago, Larry would really appreciate hearing something like that. Somehow, it didn't make much of a difference at the present time.
Larry needed a shower and some time to rest after the work out session he had with his teacher and proceeded past the pool area to the lobby, then to the elevator; the short trip up was more than enough to bring some fond memories of his first encounter with Sue. The lift arrived at his floor and Larry got out; he couldn't help but smile as he headed towards his bedroom for a deserved break.
***
Jessica was in the bathroom, drying her hair and put on her makeup. She had a good time at the pool with her friend Jill and managed to work on her tan some more. Jessica noticed how Larry kept ogling at her friend's attributes and thought about the possibility of maybe hooking up the two of them. She shook her head no, and immediately realized the funny idea she had; a hot girl like Jill would never fall for someone like Higgs.
As she dried her hair she didn't hear the door to her room opening. Only when the thud of the door closing grabbed her attention did she say anything.
"Hey, Nate!" She called out. "What took you so long, baby? I am starving!"
Unbeknownst to her that her boyfriend was still in the process of getting breakfast; just when Larry was about to get in his room, he remembered he had promised Nate to warn his girlfriend Jess about his whereabouts. Before Larry could let his friend's girl know that it was him and not his Nate, Jessica walked out of the bathroom in nothing but her panties.
"Well, what do you..." Jessica stopped mid sentence as she saw her boyfriend's wide eyed geeky buddy standing before her.
Even though it was only about a moment, Larry did his best to memorize Jess's naked form. She was standing there with her arms above her head brushing her hair. Her breasts were hanging freely and the only bit of clothing she had on was a pair of light pink panties. Knowing he had to do something fast or risk getting screamed at, Larry thought fast.
"Oh, Jess!" Larry yelled covering his eyes reluctantly. "Sorry about that!"
Jessica wasn't mad; it appeared to be an honest mistake, the same one she had done earlier, as a matter of fact. Besides so far no harm was done and her boyfriend wasn't even in the room.
"It's okay, Larry." Jessica said grabbing a towel off the bed. "Next time you should probably knock, though."
"I did." Larry lied as he uncovered his eyes.
"Well, Nate is not here." She informed him. "Now you'd better leave before he comes back. It would be ... awkward, if he found you here."
"Oh, about that." Larry replied as he closed the door on his way out. "Nate told me to tell you that he is getting breakfast and will come back in just a bit."
"Okay, thanks." Jessica acknowledged.
"Damn, what a way to start the day." Larry thought to himself.
***
After about twenty five minutes, Nate made it back with their breakfast. Jessica didn't know what was up with her boyfriend but he wasn't paying her any attention at all. She had put on a little sundress and was nonchalantly posing on the bed when Nate came into the room. He didn't even glance in her direction.
"I'm gonna rinse off." Nate mumbled.
Jessica pouted for a few minutes then got up to look out the window. Below her she could see all the people swimming in the pool. After a while Jessica spotted someone familiar. The young guy, Paul, from yesterday was lounging by the side of the pool. Jessica stared at Paul for a while before realizing that she was smiling and rubbing her shoulders gently.
"I bet he'd pay attention to me." Jessica thought as she stared at Paul.
Jessica's daydream came to an end when she heard the shower cut off. Nate spent the next couple minutes drying off and getting dressed. The shower had done wonders and he felt a lot better. Today he was going to see what kind of sport options L.A. had to offer. After he got dressed he finally made eye contact with his girlfriend.
"Hey, I was thinking I'd..." Nate began, but was interrupted.
"Spend the day with me." Jessica said sarcastically.
Nate knew his girlfriend was slightly perturbed at him so he chose his words wisely. He knew he could check out the courts later. If he had to do a little time and walk around the city with his girlfriend to keep things smooth so be it.
"That's exactly what I was thinking." Nate smiled.
"Smart boy." Jessica smiled back.
They chatted and tried to decide what to do for the day. They agreed to see some of the local sights and if the opportunity presented itself attend to something out of the ordinary.
"Should we call Higgs, baby?" Nathan asked his girlfriend.
"I don't know, I kind of wanted to spend some time alone with you." Jessica hesitated. "Besides, I think I seen too much of the nerd already."
"Give the kid a break, Jess." Nathan was sympathetic. "I feel bad for him, he has no friends and no one wants him around. The boy is a virgin, for Christ's sake."
"Alright, alright." Jessica agreed. "That loser can hang with us, but I don't expect me to babysit him."
"Okay, baby." Nathan kissed his girlfriend. "I will call him out."
***
Throughout the day, the trio passed lots of famous places and gaudily decorated establishments, just the usual L.A. attractions. Larry used every opportunity to stare intently at his pal's girl's ass as they walked.
After a quick lunch, the group was making their way back to the hotel when they passed a large sports complex; from where they stood, they could see young people playing ball, through the fence. Nate was instantly curious.
"Hey, let's check this out for a second." Nate said.
Reluctantly, Jessica and Larry followed Nate around. Larry noticed the twinkle in his friend's eyes and began to see that this might just be what he needed to keep his friend busy.
"That's it!" Larry said as he spotted a sign that said: One-on-One Tournament.
Larry talked to a man sitting by the sign and it turns out that for $35 he could set his friend up in the tournament. He immediately paid the entrance fee and gave it to Nathan, as a gift; actually, only thing running through his mind were visions of his buddy's girlfriend.
"Thanks, Higgs!" Nathan appreciated the gesture. "Do you mind if I play a match, baby?"
"No, honey." Jessica wanted her boyfriend to enjoy himself as well. "Knock yourself out."
***
A few minutes turned into a couple of hours and Jessica and her Larry were becoming bored.
"Hey Jess, I think I'm gonna take a look around." Larry smiled.
"I don't blame you, I won't last much longer either." Jessica replied.
"I'll catch up to you guys later." Larry said as he left.
Jessica waved and went to try and drag her boyfriend out. After a few minutes it became abundantly clear that Nate was mesmerized and wouldn't be leaving anytime soon.
"But what am I supposed to do while you're standing here with your tongue hanging out?" Jessica asked with her arms on her hips.
"Baby, come on! You can..."
"I know, I know. I can do anything I want to." Jessica interrupted.
"Yeah." Nate returned to play. "I am sure you will think of something."
***
Frustrated, Jessica went back to the hotel and flipped through the channels on the television. After a while, she walked into the bathroom to do a quick touch up on her hair and makeup. As she messed with her hair Jessica glanced down at the little folded piece of paper lying on the corner of the cabinet.
As she unfolded the paper Jessica smiled. It was that good looking boy's number. Jessica thought back to the first day at the pool and the young man rubbing lotion her back. A warm fuzzy feeling enveloped her body and she wondered if the young man was still by the pool; she skipped over to the window.
"Hey there." Jessica whispered as she noticed her young admirer still lounging by the pool.
She felt slightly guilty about wanting to go down to the pool again; she was committed and had no business flirting with the young man. But, on the other hand, her boyfriend wasn't around and he didn't seem to be too interested in what she was doing anyway. Besides, it's only flirting she told herself.
Jessica slipped off her dress and searched through her luggage for one of her swimsuits. She pulled out a black string bikini that she'd bought before the trip. She'd planned on showing Nate first, but if all he wanted to see were sweaty players then so be it. After tying the top together Jessica looked herself over in the mirror. The reflection that stared back at her was sure to grab the boy's attention.
"Just right, only slightly slutty..." Jessica laughed putting on her sunglasses.
Larry roamed around, trying to pick women, with no luck. He was thinking on how to go about getting his pal's girlfriend alone again tonight. He decided to make a pit stop by the sports complex his friend was at to tell him to enjoy himself and that he'd keep Jess company for the evening.
Then maybe he could take her out dancing and get her sloshed again. After searching for a few minutes Larry found his friend at one of the courts. He was grinning widely and from his sweaty state Larry could tell he was working hard to win.
"Hey Nate, looks like you're doing pretty good." Larry said.
"You bet. I'm on a hell of a streak." Nate replied.
"Seems like you are really having a good time." Larry smiled.
"Hold on just one sec, Higgs." Nate said as he gestured the other players he would be taking a short break.
Nate grabbed a bottle of water and walked with his friend.
"Damn, those guys are really though!" Nate was excited. "They provide some real challenge!"
"Well, I thought you would get a kick out of this." Larry lied.
Nate smiled broadly. He'd always wanted to practice at a fancy place.
"That was a damn fine present, Higgs." Nate smiled.
"Are you going to hang out here all afternoon?" Larry asked.
"I would love to, but I don't think Jess would like sitting here with me that much time." Nate replied.
"Don't worry about it." Larry assured him. "I'll keep Jess busy and you can have some fun."
"But I'm supposed to take her out to dinner tonight." Nathan declined. "I don't think she'd like me standing her up."
"Just chill." Larry insisted. "I said I'd take care of it."
Nate rubbed his chin for a second and then put his hand on his friend's shoulder.
"That might be the best idea you've ever had, Higgs." Nate smiled.
"Just remember if you keep winning, drink one for me." Larry joked.
"Sure!" Nate replied jokingly. "Which one?"
"Surprise me, just make sure it is a strong one!" Larry said. "I'll see you tomorrow, Nate."
***
Back at the hotel, Paul was soaking up some rays when a shadow covered him. With his eyes closed, he at first thought it was a cloud but after a few seconds he cracked open his eyes slightly.
"I hope I'm not interrupting." Jessica said standing there in her black bikini with her hands on her hips.
Paul sat up so fast he got dizzy headed. With his mouth slightly open he stared intently at the beautiful woman in front of him. Jessica blushed because of the look Paul was giving her.
"You can interrupt me anytime you want." Paul finally said.
Jessica sat down on the chair next to him and stretched out. The two made small talk while Jessica put lotion on her arms and stomach.
"That California sun doesn't mess around." Jessica complained. "It's gotta be 110 degrees out here."
"It got a lot hotter when you came out here." Paul smiled.
"How long did you rehearse that one?" Jessica laughed.
"All morning." Paul confessed. "Hey, I could use a drink, how about you?"
"Sounds good." Jessica smiled.
Paul returned with two Piña Coladas and the two talked for a while. Jessica was really starting loosen up, they talked liked they'd known each other for years. Besides, all she could think about was how good it felt the other day when the boy was rubbing lotion onto her back.
The only problem was that Jessica knew where this train of thought was leading her. She was going to ask Paul to put some lotion on her back, and if she did, she'd be the one opening the door for something she'd have a hard time controlling. After putting lotion on her legs, Jessica handed Paul the bottle and smiled.
"You mind?" Jessica said as she turned over onto her stomach.
"No problem at all." Paul replied.
Jessica figured there was no reason to be shy, besides, with the drink in her system she was really starting to relax. She just wanted to lie in the sun and enjoy herself. What better way was there than to have this young stud rub lotion all over her.
Paul was so horny he almost couldn't control himself. He thanked his lucky stars that he'd decided to come back to the pool today. He gently rubbed the lotion into Jessica's shoulders and began to work his way down her back. Deciding to be daring Paul untied Jessica's top without warning. Before she could react, he continued rubbing the lotion into her skin.
"You'd better be careful back there." Jessica said as she smiled at the young man's cockiness.
"Just don't want you to burn." Paul smiled.
Jessica was almost asleep; she was so comfortable. It was warm, she felt wonderful, and as Paul's hands slid over her body she didn't think it could get any better. Her eyes opened a little wider as his hands began to slide down to her sides. Jessica softly gasped as Paul's fingers rubbed along the outer swells of her breasts.
"Oh, man!" Paul thought to himself as his fingers slide along the edge of Jessica's tits.
Jessica debated stopping him but she decided against it. He wasn't being overly inappropriate and he eventually moved on. However, it wasn't before she began to feel a tingle between her legs. Paul continued his gentle assault and worked his way down to Jessica's lower back.
"Umm..." Jessica moaned as Paul began massaging the lotion into the small of her back.
Paul remembered she loved having the small of her back rubbed. He was more than happy to comply. After a few minutes, slowly but surely, Paul began to run his fingers under Jessica's bikini bottom ever so slightly. At first Jessica didn't think too much about it but as time went on she could feel Paul' fingers going ever lower.
Paul was breathing very fast by now. He knew he was treading on dangerous ground but he couldn't resist. Eventually, he felt his middle finger slip in between Jessica's cheeks. Paul barely moved. He was waiting to see if she would react and stop him like the day before.
"Oh my," Jessica thought.
She knew she should stop Paul but it felt so good. Glancing over the top of her sunglasses, she surveyed the scene. No one seemed to be paying them any attention. Jessica smiled and decided to be naughty and let Paul have his fun, as long as he didn't go too far.
Paul was surprised that Jessica didn't seem to care where his hands were. He took a deep breath and began to run his hands farther under Jessica's bottoms. Before long he was rubbing lotion all over Jessica's ass. Ever so gently Paul squeezed the firm globes of flesh. Becoming even more mesmerized, Paul slightly pulled Jessica's cheeks apart and firmly squeezed her ass.
"Ohhh, God." Jessica moaned as she bit her bottom lip.
She knew she had to do something but she didn't want to scare the boy off.
"Hey babe, I could use a refill." Jessica quietly said.
"Oh ... um ... sure." Paul mumbled. "I guess I could use one myself."
Reluctantly, Paul removed his hands from Jessica's ass and he grabbed their glasses and made his way over to the bar. About this time, Larry was coming back to the hotel. He noticed Paul at the bar and decided to say hello.
"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.
"I think I'm going to go back to my room and call it a night." Jessica said.
"Can I call you tomorrow?" Paul asked.
"Sure." Jessica said.
With that, Jessica leaned down and kissed Paul on the forehead and called a cab to take her back to the hotel. On the ride, Jessica began to feel very bad for what had happened. She couldn't believe she'd let things get so out of hand. If only her boyfriend would've been the one with her. But no, he had to play a stupid game.
Back at the hotel, Larry was lying in Nate's bed, naked under the covers. He patiently waited as he gently tugged on his cock. He knew Jess would be home sooner or later, and knowing her, she would be sloshed. As an extra precaution, Larry had turned the air conditioner on full blast. It was loud enough he thought, to help disguise his voice if she asked him any questions.
As Jessica's cab pulled up at the hotel, her head was still spinning. She didn't know if it was the alcohol or Paul getting her so worked up, but she was very light headed. On her way to the elevators, she spotted the hotel bar and decided that just one more drink would help her pass on out quietly in her room, or at least that's what she thought. After about an hour, and three glasses of Piña Colada, Jessica finally stumbled into the elevator and made her way to her room.
"Ha! I might just have to sleep in the hall." Jessica laughed as she tried four times to get her keycard into the slot.
Inside the room, Larry heard the commotion and quickly turned off the television. The door slowly opened and Jessica stumbled inside. Larry could tell from her movements that she was drunk; he smiled knowing his planned had worked like a charm. Jessica stumbled into the room and closed the door. She was surprised that her boyfriend had made it home before her.
"Honey, are you awake?" She asked.
Not knowing what to do Larry rolled over and grunted something to the effect of, "Uh Huh."
Jessica dropped her purse on the floor and slipped off her shoes before sitting down on the bed. She felt terrible about what she'd done but that was hopefully behind her now. All she wanted to do was cuddle up next to her boyfriend and go to bed.
"Did you have fun tonight?" Jessica asked.
"Uh Huh." Larry mumbled.
"That's good, I had a pretty good night myself but I'm glad you're here, baby." Jessica said as she laid down beside who she thought was her boyfriend.
Jessica cuddled up next to Larry and laid her head on his chest. Larry was in heaven as his cock began to tent the sheets. Slowly, Larry let his hand slide down Jessica's back and slip under her dress. He rubbed his fingertips slowly up and down trying to spark a reaction from his buddy's girlfriend.
"Ummmm..." Jessica said. "That feels great, Nate."
Jessica ran her hand over Larry's stomach and accidentally bumped something with her hand. Not knowing for sure what it was Jessica reached further down and slowly a smile crept across her lips.
"I guess you really are awake." Jessica said as she rubbed Larry's cock through the blanket.
"UmHmmm." Larry groaned with his Jess's hand on his cock.
"Well, since we're both still up..." Jessica said as she sat up in the bed.
Larry watched breathlessly as his friend's girl pulled down the sheets leaving him completely naked. Jessica was still very turned on from earlier. Besides, in her mind, the thought of fucking her boyfriend senseless could possibly make up for what she did earlier. Jessica grabbed Larry's cock and slowly stroked it up and down; it felt so big she had to use both hands. Larry grinned broadly in the darkness. Jessica licked her lips and then lowered her head to his crotch.
"Ohhhhh, shit!" Larry hissed as the wonderful feeling of Jess' warm, wet mouth enveloped his hard cock.
Jessica moaned as Larry's cock passed her tongue and bumped the back of her throat. Expertly her pink lips slid up and down the geek's hard shaft. As she sucked, Jessica could feel Larry's cock pulse with his heartbeat. She held a steady pace before popping the head of Larry's cock out of her mouth and running her tongue over his balls. The salty taste on her tongue and the musky smell in her nostrils had Jessica's pussy absolutely dripping wet.
"Oh, God baby..." Jessica moaned as she swirled her tongue around the huge head of his cock. "I'm so fucking wet!"
Larry was very close to cumming. He was slightly relieved when his friend's girl removed his cock from her mouth and began planting little kisses up his abdomen. Jessica swung one leg over him and sat atop him breathing heavily. Very slowly, she pulled her dress over her head. Even in the darkness Larry could slightly make out the sight of Jess sitting on top of him.
"C'mere, stud!" Jessica said as she leaned down and unknowingly kissed the nerd.
Their tongues danced as the room went silent. Larry grabbed one of his friend's girl's tits and squeezed very firmly as his other hand squeezed her ass.
"Fuck yeah, baby!" Jessica moaned as Larry took her nipple in his mouth.
Jessica groaned and moaned as unbeknownst to her, Larry's expert mouth had both her nipples standing at attention. After working on her tits for a while Larry pulled Jess' head back to his and they kissed passionately for minute after minute. The taste of Jessica's soft lips was driving him crazy.
Larry flipped over on top of her, never breaking their kiss. He slowly made his was down Jessica's neck. He ventured even lower, dragging his tongue down between her tits, and then to her stomach. Jessica's toes curled in ecstasy. Eventually, Larry arrived at his destination.
"Oh, God!" Larry moaned with his face right over her panty covered pussy. "Yes!"
He'd waited a long time for this moment. Like a conquering king, Larry pulled his pal's girlfriend's panties down her long legs. He then brought them to his face and inhaled deeply. Jessica cooed with delight as she felt her legs being spread; she was ready.
"Oh, God, baby..." Jessica moaned in anticipation. "Please..."
Larry didn't wait around for long. He spread Jess' pussy lips and in one long, slow lick, coated her wet pussy with his tongue. He slowly sucked at her clit while massaging her inner thigh with his free hand.
"Oh, my God!" Jessica moaned. "Fuck!"
Larry was like a fat guy at an all you can eat buffet. He hungrily sucked and licked her pussy for all he was worth. The sweet taste of her pussy coated his tongue. After a few minutes, he could feel her starting to shake. Just a little at first but then she started to really thrash.
"Oh God, baby..." Jessica moaned. "Don't stop! Fuck, yeah!"
Caught up in the moment Jessica grabbed the nerd by the head with both hands and pulled his face tightly against her pussy. Larry's tongue never missed a beat.
"Oh, fuck! Fuck!" Jessica screamed as her pussy exploded into the dork's sucking mouth. "I'm cumming!"
Larry's tongue was covered in her love juice but he never relented. He kept up his pace as Jessica convulsed in absolute pleasure.
"Gawd, that feels so fucking good!" Jessica screamed as she slowly regained control of her body.
After a few minutes Larry removed his tongue from her pussy and crawled up between her legs. He stared down at his friend's girl, almost completely obscured by shadow. He leaned forward slightly until the tip of his cock touched Jessica's soaking pussy.
"Give it to me, baby." Jessica said. "Hard!"
Larry's mouth hung open and he slowly eased his cock into his pal's girlfriend's warm, smooth pussy. The feeling was like no other, pure sexual pleasure. Jessica gritted her teeth as the nerd's enormous hard cock spread her sensitive pussy wide. Eventually, Larry came to rest, his cock buried all the way inside Jess' pussy.
Jessica didn't know if it was something in L.A. or what but her boyfriend's cock seemed to be bigger and harder than ever. Larry leaned down and kissed Jessica passionately with her juices still on his lips. Jessica swirled her tongue around his mouth. They were connected in every way in that moment.
"Fuck me baby..." Jessica quietly begged. "Pound that fat cock all the way in and out!"
Larry began to rhythmically slide his cock in and out of his friend's girl. He fucked her slowly at first, but then hard and fast. Soon, the room was filled with the sound of flesh slapping flesh. Larry's cock slammed deep into his Jess' pussy. Jessica couldn't remember the last time her boyfriend had fucked her so hard but she loved it.
"Yeah! That's it!" Jessica groaned as she wrapped her legs around the pale boy's back. "I'm such a slut for your big cock!"
Larry was doing his best to hold out, but he knew he was about to blow. Wanting Jessica to remember this fucking, even if she didn't know it was him, Larry pulled out all the stops. He wrapped his arms around her back and lifted her off the bed. He was on his knees on the bed with Jess wrapped around him.
He began bouncing Jessica up and down on his long, fat cock violently. Jessica didn't know what had gotten into her boyfriend and she didn't care. She moaned loudly as the hard cock between her legs seemed to go even deeper into her hot, wet cunt.
"Oh, fuck!" Larry hissed as his climax neared. "Your pussy is so fucking tight!"
Larry slammed his friend's girl back onto the bed and with three mighty thrusts his cock exploded into her waiting pussy.
"Uuggghhhh..." Larry groaned as his cock emptied volley after volley of his seed into her abused snatch. "Fuck, yeah!"
Jessica's hands uncontrollably clenched the sheets as the geek's hot cum coated the inside of her pussy. Larry came for what seemed like forever. Jessica felt cum dripping from her pussy and knew that her boyfriend was filling her up like he hadn't done in a long while.
After several minutes, Larry stopped cumming and, as his cock softened inside her, he leaned down and sucked her tongue into his mouth once more. Jessica's tongue wrestled his as she felt his cock slip from her pussy. Larry rolled to the side and the two just laid there in a sweaty heap as their breathing returned to normal.
After twenty minutes or so, Jessica got up and went to the bathroom. Larry laid on the bed thinking about what'd just happened again. He was really getting addicted to Jess' pussy. As he lay there thinking of her, his cock began to come back to life.
In the bathroom, Jessica looked at herself in the mirror. She smiled at her reflection. Her hair was a mess and her lipstick was smeared slightly. She had the look of a well fucked woman. After she turned off the light, she closed the door and climbed back into bed. She snuggled up to Larry and laid her hand on his stomach.
"That was amazing." Jessica said rubbing his abdomen.
Feeling daring, Larry grabbed her hand and guided it down to his hard cock.
"Damn Nate, what's gotten into you?" Jessica asked amazed at her boyfriend's new found endurance.
Larry smiled when she called him by her boyfriend's name. He ran his fingers tenderly through her hair and gently pushed her head down toward his cock. Jessica didn't fight his insistence to suck his cock at all. In fact, she was all for round two.
"Oh, baby..." Jessica asked as she stroked the monster cock in front of her. "Is this for me?"
Larry didn't reply; he just gently pushed her head down onto his cock. His mouth opened and he exhaled loudly as Jessica's lips slipped over the head of his hard cock. Jessica took about half his cock into her mouth and sucked hard on the way back up. Larry's cock escaped her mouth with a loud pop.
Jessica rubbed her pussy as she took dork's cock back into her warm mouth. After what had happened with Paul, Jessica felt like she owed her boyfriend some tender loving care. Jessica released the hard cock from her mouth and licked her way down to his balls. One after the other she sucked them into her mouth.
Larry was in heaven with his Jessica's head between his legs but he wasn't about to just lay there. He sat up slightly and slapped his friend's girl on the ass trying to make her lift her rear end off the bed because he had something special in mind.
Jessica momentarily stopped her assault on her boyfriend's unusually immense cock when he slapped her on the ass. Not knowing what he wanted she went back to sucking his dick. Larry was tempted to tell her what to do but he didn't want to risk it. Instead, he laid back down and grabbed her by the waist and pulled her on top of him while she was still giving him head.
"Whoa, baby!" Jessica said as Larry's cock popped out of her mouth.
With her feet up by his head, Larry forcibly spread her legs apart, and pulled her up until her ass was right over his mouth. He had to taste her again. Larry spread Jessica's butt cheeks and stuck his tongue in as far as it would go.
"Oh, Gawd!" Jessica screamed.
Never before had her boyfriend had her this turned on. In between moans of pleasure, Jessica sucked his cock, all the while not knowing that her boyfriend was miles away. Jessica clenched her thighs around the nerd's head, put her hands on his abdomen and pushed herself up until she was literally sitting on his face.
"Oh, fuck! Yeah! Keep going!" Jessica screamed. "God, don't stop!"
Larry's tongue went into overdrive as his friend's girl's pussy began to quiver in his mouth. Jessica pinched her nipples hard and began running her hands through her hair like a woman possessed. Her pussy was on fire. She couldn't control her breathing and was becoming very light headed.
She surely would have passed out if she knew it was some scrawny geek's tongue doing this to her. Larry ran his hands over her ass as he ate her for all he was worth. In an act of daring, Larry slipped the tip of his index finger into her ass. That was all Jessica could handle.
"Ohhhhh ... OhhhhMyGod..." Jessica screamed as she came like she'd never came before. "OhhMyGodOhhMyGod!"
Jessica lost all muscle control as she came in his mouth. Jessica's whole body shook and quivered uncontrollably. She was out of control as she sat there, on the dork's face, with her mouth open wide. Never before had she came three times in one night.
After almost two solid minutes, Jessica finally collapsed to his side. In the position she fell, her head was right next to the edge of the bed. Jessica was literally in a trance. She couldn't talk or move. She just lay there silently.
Larry was ecstatic that he'd made his friend's girl cum so hard but he still needed release. He put his hand on her hip and pulled to see if she was still game but it was like pulling a dead body. Undaunted, Larry got off the bed and went around to where Jessica's head was.
Jessica was still in a fog when she felt what could only be a cock pushing into her mouth. Trying her best to suck her boyfriend's cock she opened her mouth. Larry slid his cock deep into her mouth. He didn't need long he just need a few seconds and he'd be satisfied.
"Oh, Fuck!" Larry hissed as he neared his climax. "Yeah!"
Even in her current stated Jessica knew what was coming. Wanting to give her boyfriend as much pleasure as he'd given her, she used what little strength she had left to grab his cock with both hands and suck as hard as she could.
"Fuck!" Larry groaned as his cum erupted into Jess' mouth.
Jessica moaned in delight as hot cum coated her tongue. Her hand milked the hard cock in her mouth relentlessly. Larry's hips bucked wildly as he filled her mouth. Jessica swallowed hard and kept jerking his mammoth cock, but as violently as Larry's hips were bucking, his cock popped out of her mouth and a long rope of cum landed on her face. Then another landed in her hair and finally, one right across her lips.
Larry collapsed onto the floor in a heap. Jessica rolled over onto her back and licked the cum from her lips. As she lay there, utterly exhausted, with cum on her and inside her, she'd never felt so dirty. She'd also never felt so satisfied. In minutes, Larry had recovered and climbed back into the bed with his friend's girl.
He managed to fuck her six more times that night. Eventually, Jessica got under the covers and before Larry knew it she was out cold. Larry smiled as he got up and put his clothes back on. If he died tomorrow he'd die a happy man he thought as he closed the door behind him.
Much later, Nate made it back to the hotel room, totally wasted as well. He'd had a great night with his new friends and one hell of a streak of luck at the game. As happy as he was, he just didn't know how he was going to tell is girlfriend that he was a finalist in the tournament.
*** Present time ***
Larry was still thinking about his encounter with Jess when he noticed someone dropped a note under his bedroom door, he imagined it could be room service. Strangely enough, the person wouldn't even knock, and that got him a bit intrigued. He decided to check on the sender's identity and rushed to the door.
Unfortunately, by the time he opened it, the hallway was empty. He picked up the note, it wasn't even folded and it read "I know what you did, Higgs!"
Second, thanks to her propensity for drinking too much, he pushed his luck and got her between the sheets once more, this time right in front of her sleeping boyfriend. Those two events alone would be more than a former virgin nerd like him could ever ask for, but there was more; he nailed two more gorgeous older women as well: Sue, who is a guest at the hotel and the hot wife of a pompous asshole, and his big-breasted school counselor, Keira.
Larry finally learned about compensation; he lacked the appeal, and certainly his dork, pale, skinny looks weren't the sexiest things around. Still, he knew that he packed a huge cock, one that seemed to have quite an effect on all those ladies he met. The naive geek was becoming something else and he could notice the changes.
As he lay there, with his arms above his head, Larry began to think about last night's events. He went further and scored another hot session of raw sex with his pal's hot girlfriend once again, without her even knowing it had happened.
"I just can't believe it. I fucked her! I fucked the shit out of her!" Larry smiled. "Damn! Who will believe me?"
***
Next room, Jessica was coming to herself. Like her boyfriend's scrawny buddy, she also smiled widely. As she stretched, Jess felt a deep soreness between her legs. Last night was the best sex she'd had in a very long while. She glanced over at her boyfriend, Nate, who was still dead to the world.
"Hmmm ... that's odd." Jessica thought noticing that Nate still had his shirt and underwear on. "Nate must have felt cold."
She could've sworn that last night her boyfriend was naked after they'd had sex. After a few minutes Jessica chalked up her foggy memory to the insane amount of alcohol she drank last night. Soon, Jessica was up and showering the night's funk away.
Looking forward to a day with her boyfriend and friends, Jessica sang softly to herself as she washed. She was very satisfied with her vacation so far. The young stud at the pool, who flirted with her, the night out dancing, and some seriously good sex topped off a wonderful week.
Nate finally came too and was thankful that he'd made it to his own bed. He was a bit surprised that he still had on all his clothes but his pants were around his ankles. He was still scratching his head when his girlfriend came out of the shower with a nothing but a towel wrapped around her hair.
"Good morning, stud." Jessica said kissing her boyfriend on the forehead.
"Morning." Nate mumbled.
"Hey, I was thinking that you and I could spend the day together, here. I could really use some cuddling." Jessica asked as she put on her panties. "What do you think?"
"Yeah, I guess so..." Nate yawned. "We'll see..."
Jessica was surprised by her boyfriend's sudden lack of interest in her. Last night was the hottest they've been for each other in years and now he wasn't giving her a second look.
"Maybe he's just hung over..." Jessica thought.
*** 20 hours earlier ***
Larry got dressed and left the locker room. He had created a lame excuse, solely to get in his hot teacher's pants and that actually worked. During the trip's few days, he managed to get more sex than what he got in his entire life, which was none, as a matter of fact.
"Hey, man!" Larry was brought back from his reveries by his friend. "Where the hell have you been?"
"I-I was, uh ... J-Just ... I mean..." Larry tried to think of something to say. Somehow, telling his friend he was shoving his big, fat cock up their counselor's tight little pussy didn't sound very believable.
"Never mind!" Nathan got tired of his friend's babbling. "I am grabbing breakfast for me and Jess, could you tell her I will be right back?"
"Huh, sure." Larry agreed. "I was on my way up, anyway."
"Thanks." Nathan said turning to leave. "You are quite a pal."
"No problem, Nate." A week ago, Larry would really appreciate hearing something like that. Somehow, it didn't make much of a difference at the present time.
Larry needed a shower and some time to rest after the work out session he had with his teacher and proceeded past the pool area to the lobby, then to the elevator; the short trip up was more than enough to bring some fond memories of his first encounter with Sue. The lift arrived at his floor and Larry got out; he couldn't help but smile as he headed towards his bedroom for a deserved break.
***
Jessica was in the bathroom, drying her hair and put on her makeup. She had a good time at the pool with her friend Jill and managed to work on her tan some more. Jessica noticed how Larry kept ogling at her friend's attributes and thought about the possibility of maybe hooking up the two of them. She shook her head no, and immediately realized the funny idea she had; a hot girl like Jill would never fall for someone like Higgs.
As she dried her hair she didn't hear the door to her room opening. Only when the thud of the door closing grabbed her attention did she say anything.
"Hey, Nate!" She called out. "What took you so long, baby? I am starving!"
Unbeknownst to her that her boyfriend was still in the process of getting breakfast; just when Larry was about to get in his room, he remembered he had promised Nate to warn his girlfriend Jess about his whereabouts. Before Larry could let his friend's girl know that it was him and not his Nate, Jessica walked out of the bathroom in nothing but her panties.
"Well, what do you..." Jessica stopped mid sentence as she saw her boyfriend's wide eyed geeky buddy standing before her.
Even though it was only about a moment, Larry did his best to memorize Jess's naked form. She was standing there with her arms above her head brushing her hair. Her breasts were hanging freely and the only bit of clothing she had on was a pair of light pink panties. Knowing he had to do something fast or risk getting screamed at, Larry thought fast.
"Oh, Jess!" Larry yelled covering his eyes reluctantly. "Sorry about that!"
Jessica wasn't mad; it appeared to be an honest mistake, the same one she had done earlier, as a matter of fact. Besides so far no harm was done and her boyfriend wasn't even in the room.
"It's okay, Larry." Jessica said grabbing a towel off the bed. "Next time you should probably knock, though."
"I did." Larry lied as he uncovered his eyes.
"Well, Nate is not here." She informed him. "Now you'd better leave before he comes back. It would be ... awkward, if he found you here."
"Oh, about that." Larry replied as he closed the door on his way out. "Nate told me to tell you that he is getting breakfast and will come back in just a bit."
"Okay, thanks." Jessica acknowledged.
"Damn, what a way to start the day." Larry thought to himself.
***
After about twenty five minutes, Nate made it back with their breakfast. Jessica didn't know what was up with her boyfriend but he wasn't paying her any attention at all. She had put on a little sundress and was nonchalantly posing on the bed when Nate came into the room. He didn't even glance in her direction.
"I'm gonna rinse off." Nate mumbled.
Jessica pouted for a few minutes then got up to look out the window. Below her she could see all the people swimming in the pool. After a while Jessica spotted someone familiar. The young guy, Paul, from yesterday was lounging by the side of the pool. Jessica stared at Paul for a while before realizing that she was smiling and rubbing her shoulders gently.
"I bet he'd pay attention to me." Jessica thought as she stared at Paul.
Jessica's daydream came to an end when she heard the shower cut off. Nate spent the next couple minutes drying off and getting dressed. The shower had done wonders and he felt a lot better. Today he was going to see what kind of sport options L.A. had to offer. After he got dressed he finally made eye contact with his girlfriend.
"Hey, I was thinking I'd..." Nate began, but was interrupted.
"Spend the day with me." Jessica said sarcastically.
Nate knew his girlfriend was slightly perturbed at him so he chose his words wisely. He knew he could check out the courts later. If he had to do a little time and walk around the city with his girlfriend to keep things smooth so be it.
"That's exactly what I was thinking." Nate smiled.
"Smart boy." Jessica smiled back.
They chatted and tried to decide what to do for the day. They agreed to see some of the local sights and if the opportunity presented itself attend to something out of the ordinary.
"Should we call Higgs, baby?" Nathan asked his girlfriend.
"I don't know, I kind of wanted to spend some time alone with you." Jessica hesitated. "Besides, I think I seen too much of the nerd already."
"Give the kid a break, Jess." Nathan was sympathetic. "I feel bad for him, he has no friends and no one wants him around. The boy is a virgin, for Christ's sake."
"Alright, alright." Jessica agreed. "That loser can hang with us, but I don't expect me to babysit him."
"Okay, baby." Nathan kissed his girlfriend. "I will call him out."
***
Throughout the day, the trio passed lots of famous places and gaudily decorated establishments, just the usual L.A. attractions. Larry used every opportunity to stare intently at his pal's girl's ass as they walked.
After a quick lunch, the group was making their way back to the hotel when they passed a large sports complex; from where they stood, they could see young people playing ball, through the fence. Nate was instantly curious.
"Hey, let's check this out for a second." Nate said.
Reluctantly, Jessica and Larry followed Nate around. Larry noticed the twinkle in his friend's eyes and began to see that this might just be what he needed to keep his friend busy.
"That's it!" Larry said as he spotted a sign that said: One-on-One Tournament.
Larry talked to a man sitting by the sign and it turns out that for $35 he could set his friend up in the tournament. He immediately paid the entrance fee and gave it to Nathan, as a gift; actually, only thing running through his mind were visions of his buddy's girlfriend.
"Thanks, Higgs!" Nathan appreciated the gesture. "Do you mind if I play a match, baby?"
"No, honey." Jessica wanted her boyfriend to enjoy himself as well. "Knock yourself out."
***
A few minutes turned into a couple of hours and Jessica and her Larry were becoming bored.
"Hey Jess, I think I'm gonna take a look around." Larry smiled.
"I don't blame you, I won't last much longer either." Jessica replied.
"I'll catch up to you guys later." Larry said as he left.
Jessica waved and went to try and drag her boyfriend out. After a few minutes it became abundantly clear that Nate was mesmerized and wouldn't be leaving anytime soon.
"But what am I supposed to do while you're standing here with your tongue hanging out?" Jessica asked with her arms on her hips.
"Baby, come on! You can..."
"I know, I know. I can do anything I want to." Jessica interrupted.
"Yeah." Nate returned to play. "I am sure you will think of something."
***
Frustrated, Jessica went back to the hotel and flipped through the channels on the television. After a while, she walked into the bathroom to do a quick touch up on her hair and makeup. As she messed with her hair Jessica glanced down at the little folded piece of paper lying on the corner of the cabinet.
As she unfolded the paper Jessica smiled. It was that good looking boy's number. Jessica thought back to the first day at the pool and the young man rubbing lotion her back. A warm fuzzy feeling enveloped her body and she wondered if the young man was still by the pool; she skipped over to the window.
"Hey there." Jessica whispered as she noticed her young admirer still lounging by the pool.
She felt slightly guilty about wanting to go down to the pool again; she was committed and had no business flirting with the young man. But, on the other hand, her boyfriend wasn't around and he didn't seem to be too interested in what she was doing anyway. Besides, it's only flirting she told herself.
Jessica slipped off her dress and searched through her luggage for one of her swimsuits. She pulled out a black string bikini that she'd bought before the trip. She'd planned on showing Nate first, but if all he wanted to see were sweaty players then so be it. After tying the top together Jessica looked herself over in the mirror. The reflection that stared back at her was sure to grab the boy's attention.
"Just right, only slightly slutty..." Jessica laughed putting on her sunglasses.
Larry roamed around, trying to pick women, with no luck. He was thinking on how to go about getting his pal's girlfriend alone again tonight. He decided to make a pit stop by the sports complex his friend was at to tell him to enjoy himself and that he'd keep Jess company for the evening.
Then maybe he could take her out dancing and get her sloshed again. After searching for a few minutes Larry found his friend at one of the courts. He was grinning widely and from his sweaty state Larry could tell he was working hard to win.
"Hey Nate, looks like you're doing pretty good." Larry said.
"You bet. I'm on a hell of a streak." Nate replied.
"Seems like you are really having a good time." Larry smiled.
"Hold on just one sec, Higgs." Nate said as he gestured the other players he would be taking a short break.
Nate grabbed a bottle of water and walked with his friend.
"Damn, those guys are really though!" Nate was excited. "They provide some real challenge!"
"Well, I thought you would get a kick out of this." Larry lied.
Nate smiled broadly. He'd always wanted to practice at a fancy place.
"That was a damn fine present, Higgs." Nate smiled.
"Are you going to hang out here all afternoon?" Larry asked.
"I would love to, but I don't think Jess would like sitting here with me that much time." Nate replied.
"Don't worry about it." Larry assured him. "I'll keep Jess busy and you can have some fun."
"But I'm supposed to take her out to dinner tonight." Nathan declined. "I don't think she'd like me standing her up."
"Just chill." Larry insisted. "I said I'd take care of it."
Nate rubbed his chin for a second and then put his hand on his friend's shoulder.
"That might be the best idea you've ever had, Higgs." Nate smiled.
"Just remember if you keep winning, drink one for me." Larry joked.
"Sure!" Nate replied jokingly. "Which one?"
"Surprise me, just make sure it is a strong one!" Larry said. "I'll see you tomorrow, Nate."
***
Back at the hotel, Paul was soaking up some rays when a shadow covered him. With his eyes closed, he at first thought it was a cloud but after a few seconds he cracked open his eyes slightly.
"I hope I'm not interrupting." Jessica said standing there in her black bikini with her hands on her hips.
Paul sat up so fast he got dizzy headed. With his mouth slightly open he stared intently at the beautiful woman in front of him. Jessica blushed because of the look Paul was giving her.
"You can interrupt me anytime you want." Paul finally said.
Jessica sat down on the chair next to him and stretched out. The two made small talk while Jessica put lotion on her arms and stomach.
"That California sun doesn't mess around." Jessica complained. "It's gotta be 110 degrees out here."
"It got a lot hotter when you came out here." Paul smiled.
"How long did you rehearse that one?" Jessica laughed.
"All morning." Paul confessed. "Hey, I could use a drink, how about you?"
"Sounds good." Jessica smiled.
Paul returned with two Piña Coladas and the two talked for a while. Jessica was really starting loosen up, they talked liked they'd known each other for years. Besides, all she could think about was how good it felt the other day when the boy was rubbing lotion onto her back.
The only problem was that Jessica knew where this train of thought was leading her. She was going to ask Paul to put some lotion on her back, and if she did, she'd be the one opening the door for something she'd have a hard time controlling. After putting lotion on her legs, Jessica handed Paul the bottle and smiled.
"You mind?" Jessica said as she turned over onto her stomach.
"No problem at all." Paul replied.
Jessica figured there was no reason to be shy, besides, with the drink in her system she was really starting to relax. She just wanted to lie in the sun and enjoy herself. What better way was there than to have this young stud rub lotion all over her.
Paul was so horny he almost couldn't control himself. He thanked his lucky stars that he'd decided to come back to the pool today. He gently rubbed the lotion into Jessica's shoulders and began to work his way down her back. Deciding to be daring Paul untied Jessica's top without warning. Before she could react, he continued rubbing the lotion into her skin.
"You'd better be careful back there." Jessica said as she smiled at the young man's cockiness.
"Just don't want you to burn." Paul smiled.
Jessica was almost asleep; she was so comfortable. It was warm, she felt wonderful, and as Paul's hands slid over her body she didn't think it could get any better. Her eyes opened a little wider as his hands began to slide down to her sides. Jessica softly gasped as Paul's fingers rubbed along the outer swells of her breasts.
"Oh, man!" Paul thought to himself as his fingers slide along the edge of Jessica's tits.
Jessica debated stopping him but she decided against it. He wasn't being overly inappropriate and he eventually moved on. However, it wasn't before she began to feel a tingle between her legs. Paul continued his gentle assault and worked his way down to Jessica's lower back.
"Umm..." Jessica moaned as Paul began massaging the lotion into the small of her back.
Paul remembered she loved having the small of her back rubbed. He was more than happy to comply. After a few minutes, slowly but surely, Paul began to run his fingers under Jessica's bikini bottom ever so slightly. At first Jessica didn't think too much about it but as time went on she could feel Paul' fingers going ever lower.
Paul was breathing very fast by now. He knew he was treading on dangerous ground but he couldn't resist. Eventually, he felt his middle finger slip in between Jessica's cheeks. Paul barely moved. He was waiting to see if she would react and stop him like the day before.
"Oh my," Jessica thought.
She knew she should stop Paul but it felt so good. Glancing over the top of her sunglasses, she surveyed the scene. No one seemed to be paying them any attention. Jessica smiled and decided to be naughty and let Paul have his fun, as long as he didn't go too far.
Paul was surprised that Jessica didn't seem to care where his hands were. He took a deep breath and began to run his hands farther under Jessica's bottoms. Before long he was rubbing lotion all over Jessica's ass. Ever so gently Paul squeezed the firm globes of flesh. Becoming even more mesmerized, Paul slightly pulled Jessica's cheeks apart and firmly squeezed her ass.
"Ohhh, God." Jessica moaned as she bit her bottom lip.
She knew she had to do something but she didn't want to scare the boy off.
"Hey babe, I could use a refill." Jessica quietly said.
"Oh ... um ... sure." Paul mumbled. "I guess I could use one myself."
Reluctantly, Paul removed his hands from Jessica's ass and he grabbed their glasses and made his way over to the bar. About this time, Larry was coming back to the hotel. He noticed Paul at the bar and decided to say hello.
"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.
"I think I'm going to go back to my room and call it a night." Jessica said.
"Can I call you tomorrow?" Paul asked.
"Sure." Jessica said.
With that, Jessica leaned down and kissed Paul on the forehead and called a cab to take her back to the hotel. On the ride, Jessica began to feel very bad for what had happened. She couldn't believe she'd let things get so out of hand. If only her boyfriend would've been the one with her. But no, he had to play a stupid game.
Back at the hotel, Larry was lying in Nate's bed, naked under the covers. He patiently waited as he gently tugged on his cock. He knew Jess would be home sooner or later, and knowing her, she would be sloshed. As an extra precaution, Larry had turned the air conditioner on full blast. It was loud enough he thought, to help disguise his voice if she asked him any questions.
As Jessica's cab pulled up at the hotel, her head was still spinning. She didn't know if it was the alcohol or Paul getting her so worked up, but she was very light headed. On her way to the elevators, she spotted the hotel bar and decided that just one more drink would help her pass on out quietly in her room, or at least that's what she thought. After about an hour, and three glasses of Piña Colada, Jessica finally stumbled into the elevator and made her way to her room.
"Ha! I might just have to sleep in the hall." Jessica laughed as she tried four times to get her keycard into the slot.
Inside the room, Larry heard the commotion and quickly turned off the television. The door slowly opened and Jessica stumbled inside. Larry could tell from her movements that she was drunk; he smiled knowing his planned had worked like a charm. Jessica stumbled into the room and closed the door. She was surprised that her boyfriend had made it home before her.
"Honey, are you awake?" She asked.
Not knowing what to do Larry rolled over and grunted something to the effect of, "Uh Huh."
Jessica dropped her purse on the floor and slipped off her shoes before sitting down on the bed. She felt terrible about what she'd done but that was hopefully behind her now. All she wanted to do was cuddle up next to her boyfriend and go to bed.
"Did you have fun tonight?" Jessica asked.
"Uh Huh." Larry mumbled.
"That's good, I had a pretty good night myself but I'm glad you're here, baby." Jessica said as she laid down beside who she thought was her boyfriend.
Jessica cuddled up next to Larry and laid her head on his chest. Larry was in heaven as his cock began to tent the sheets. Slowly, Larry let his hand slide down Jessica's back and slip under her dress. He rubbed his fingertips slowly up and down trying to spark a reaction from his buddy's girlfriend.
"Ummmm..." Jessica said. "That feels great, Nate."
Jessica ran her hand over Larry's stomach and accidentally bumped something with her hand. Not knowing for sure what it was Jessica reached further down and slowly a smile crept across her lips.
"I guess you really are awake." Jessica said as she rubbed Larry's cock through the blanket.
"UmHmmm." Larry groaned with his Jess's hand on his cock.
"Well, since we're both still up..." Jessica said as she sat up in the bed.
Larry watched breathlessly as his friend's girl pulled down the sheets leaving him completely naked. Jessica was still very turned on from earlier. Besides, in her mind, the thought of fucking her boyfriend senseless could possibly make up for what she did earlier. Jessica grabbed Larry's cock and slowly stroked it up and down; it felt so big she had to use both hands. Larry grinned broadly in the darkness. Jessica licked her lips and then lowered her head to his crotch.
"Ohhhhh, shit!" Larry hissed as the wonderful feeling of Jess' warm, wet mouth enveloped his hard cock.
Jessica moaned as Larry's cock passed her tongue and bumped the back of her throat. Expertly her pink lips slid up and down the geek's hard shaft. As she sucked, Jessica could feel Larry's cock pulse with his heartbeat. She held a steady pace before popping the head of Larry's cock out of her mouth and running her tongue over his balls. The salty taste on her tongue and the musky smell in her nostrils had Jessica's pussy absolutely dripping wet.
"Oh, God baby..." Jessica moaned as she swirled her tongue around the huge head of his cock. "I'm so fucking wet!"
Larry was very close to cumming. He was slightly relieved when his friend's girl removed his cock from her mouth and began planting little kisses up his abdomen. Jessica swung one leg over him and sat atop him breathing heavily. Very slowly, she pulled her dress over her head. Even in the darkness Larry could slightly make out the sight of Jess sitting on top of him.
"C'mere, stud!" Jessica said as she leaned down and unknowingly kissed the nerd.
Their tongues danced as the room went silent. Larry grabbed one of his friend's girl's tits and squeezed very firmly as his other hand squeezed her ass.
"Fuck yeah, baby!" Jessica moaned as Larry took her nipple in his mouth.
Jessica groaned and moaned as unbeknownst to her, Larry's expert mouth had both her nipples standing at attention. After working on her tits for a while Larry pulled Jess' head back to his and they kissed passionately for minute after minute. The taste of Jessica's soft lips was driving him crazy.
Larry flipped over on top of her, never breaking their kiss. He slowly made his was down Jessica's neck. He ventured even lower, dragging his tongue down between her tits, and then to her stomach. Jessica's toes curled in ecstasy. Eventually, Larry arrived at his destination.
"Oh, God!" Larry moaned with his face right over her panty covered pussy. "Yes!"
He'd waited a long time for this moment. Like a conquering king, Larry pulled his pal's girlfriend's panties down her long legs. He then brought them to his face and inhaled deeply. Jessica cooed with delight as she felt her legs being spread; she was ready.
"Oh, God, baby..." Jessica moaned in anticipation. "Please..."
Larry didn't wait around for long. He spread Jess' pussy lips and in one long, slow lick, coated her wet pussy with his tongue. He slowly sucked at her clit while massaging her inner thigh with his free hand.
"Oh, my God!" Jessica moaned. "Fuck!"
Larry was like a fat guy at an all you can eat buffet. He hungrily sucked and licked her pussy for all he was worth. The sweet taste of her pussy coated his tongue. After a few minutes, he could feel her starting to shake. Just a little at first but then she started to really thrash.
"Oh God, baby..." Jessica moaned. "Don't stop! Fuck, yeah!"
Caught up in the moment Jessica grabbed the nerd by the head with both hands and pulled his face tightly against her pussy. Larry's tongue never missed a beat.
"Oh, fuck! Fuck!" Jessica screamed as her pussy exploded into the dork's sucking mouth. "I'm cumming!"
Larry's tongue was covered in her love juice but he never relented. He kept up his pace as Jessica convulsed in absolute pleasure.
"Gawd, that feels so fucking good!" Jessica screamed as she slowly regained control of her body.
After a few minutes Larry removed his tongue from her pussy and crawled up between her legs. He stared down at his friend's girl, almost completely obscured by shadow. He leaned forward slightly until the tip of his cock touched Jessica's soaking pussy.
"Give it to me, baby." Jessica said. "Hard!"
Larry's mouth hung open and he slowly eased his cock into his pal's girlfriend's warm, smooth pussy. The feeling was like no other, pure sexual pleasure. Jessica gritted her teeth as the nerd's enormous hard cock spread her sensitive pussy wide. Eventually, Larry came to rest, his cock buried all the way inside Jess' pussy.
Jessica didn't know if it was something in L.A. or what but her boyfriend's cock seemed to be bigger and harder than ever. Larry leaned down and kissed Jessica passionately with her juices still on his lips. Jessica swirled her tongue around his mouth. They were connected in every way in that moment.
"Fuck me baby..." Jessica quietly begged. "Pound that fat cock all the way in and out!"
Larry began to rhythmically slide his cock in and out of his friend's girl. He fucked her slowly at first, but then hard and fast. Soon, the room was filled with the sound of flesh slapping flesh. Larry's cock slammed deep into his Jess' pussy. Jessica couldn't remember the last time her boyfriend had fucked her so hard but she loved it.
"Yeah! That's it!" Jessica groaned as she wrapped her legs around the pale boy's back. "I'm such a slut for your big cock!"
Larry was doing his best to hold out, but he knew he was about to blow. Wanting Jessica to remember this fucking, even if she didn't know it was him, Larry pulled out all the stops. He wrapped his arms around her back and lifted her off the bed. He was on his knees on the bed with Jess wrapped around him.
He began bouncing Jessica up and down on his long, fat cock violently. Jessica didn't know what had gotten into her boyfriend and she didn't care. She moaned loudly as the hard cock between her legs seemed to go even deeper into her hot, wet cunt.
"Oh, fuck!" Larry hissed as his climax neared. "Your pussy is so fucking tight!"
Larry slammed his friend's girl back onto the bed and with three mighty thrusts his cock exploded into her waiting pussy.
"Uuggghhhh..." Larry groaned as his cock emptied volley after volley of his seed into her abused snatch. "Fuck, yeah!"
Jessica's hands uncontrollably clenched the sheets as the geek's hot cum coated the inside of her pussy. Larry came for what seemed like forever. Jessica felt cum dripping from her pussy and knew that her boyfriend was filling her up like he hadn't done in a long while.
After several minutes, Larry stopped cumming and, as his cock softened inside her, he leaned down and sucked her tongue into his mouth once more. Jessica's tongue wrestled his as she felt his cock slip from her pussy. Larry rolled to the side and the two just laid there in a sweaty heap as their breathing returned to normal.
After twenty minutes or so, Jessica got up and went to the bathroom. Larry laid on the bed thinking about what'd just happened again. He was really getting addicted to Jess' pussy. As he lay there thinking of her, his cock began to come back to life.
In the bathroom, Jessica looked at herself in the mirror. She smiled at her reflection. Her hair was a mess and her lipstick was smeared slightly. She had the look of a well fucked woman. After she turned off the light, she closed the door and climbed back into bed. She snuggled up to Larry and laid her hand on his stomach.
"That was amazing." Jessica said rubbing his abdomen.
Feeling daring, Larry grabbed her hand and guided it down to his hard cock.
"Damn Nate, what's gotten into you?" Jessica asked amazed at her boyfriend's new found endurance.
Larry smiled when she called him by her boyfriend's name. He ran his fingers tenderly through her hair and gently pushed her head down toward his cock. Jessica didn't fight his insistence to suck his cock at all. In fact, she was all for round two.
"Oh, baby..." Jessica asked as she stroked the monster cock in front of her. "Is this for me?"
Larry didn't reply; he just gently pushed her head down onto his cock. His mouth opened and he exhaled loudly as Jessica's lips slipped over the head of his hard cock. Jessica took about half his cock into her mouth and sucked hard on the way back up. Larry's cock escaped her mouth with a loud pop.
Jessica rubbed her pussy as she took dork's cock back into her warm mouth. After what had happened with Paul, Jessica felt like she owed her boyfriend some tender loving care. Jessica released the hard cock from her mouth and licked her way down to his balls. One after the other she sucked them into her mouth.
Larry was in heaven with his Jessica's head between his legs but he wasn't about to just lay there. He sat up slightly and slapped his friend's girl on the ass trying to make her lift her rear end off the bed because he had something special in mind.
Jessica momentarily stopped her assault on her boyfriend's unusually immense cock when he slapped her on the ass. Not knowing what he wanted she went back to sucking his dick. Larry was tempted to tell her what to do but he didn't want to risk it. Instead, he laid back down and grabbed her by the waist and pulled her on top of him while she was still giving him head.
"Whoa, baby!" Jessica said as Larry's cock popped out of her mouth.
With her feet up by his head, Larry forcibly spread her legs apart, and pulled her up until her ass was right over his mouth. He had to taste her again. Larry spread Jessica's butt cheeks and stuck his tongue in as far as it would go.
"Oh, Gawd!" Jessica screamed.
Never before had her boyfriend had her this turned on. In between moans of pleasure, Jessica sucked his cock, all the while not knowing that her boyfriend was miles away. Jessica clenched her thighs around the nerd's head, put her hands on his abdomen and pushed herself up until she was literally sitting on his face.
"Oh, fuck! Yeah! Keep going!" Jessica screamed. "God, don't stop!"
Larry's tongue went into overdrive as his friend's girl's pussy began to quiver in his mouth. Jessica pinched her nipples hard and began running her hands through her hair like a woman possessed. Her pussy was on fire. She couldn't control her breathing and was becoming very light headed.
She surely would have passed out if she knew it was some scrawny geek's tongue doing this to her. Larry ran his hands over her ass as he ate her for all he was worth. In an act of daring, Larry slipped the tip of his index finger into her ass. That was all Jessica could handle.
"Ohhhhh ... OhhhhMyGod..." Jessica screamed as she came like she'd never came before. "OhhMyGodOhhMyGod!"
Jessica lost all muscle control as she came in his mouth. Jessica's whole body shook and quivered uncontrollably. She was out of control as she sat there, on the dork's face, with her mouth open wide. Never before had she came three times in one night.
After almost two solid minutes, Jessica finally collapsed to his side. In the position she fell, her head was right next to the edge of the bed. Jessica was literally in a trance. She couldn't talk or move. She just lay there silently.
Larry was ecstatic that he'd made his friend's girl cum so hard but he still needed release. He put his hand on her hip and pulled to see if she was still game but it was like pulling a dead body. Undaunted, Larry got off the bed and went around to where Jessica's head was.
Jessica was still in a fog when she felt what could only be a cock pushing into her mouth. Trying her best to suck her boyfriend's cock she opened her mouth. Larry slid his cock deep into her mouth. He didn't need long he just need a few seconds and he'd be satisfied.
"Oh, Fuck!" Larry hissed as he neared his climax. "Yeah!"
Even in her current stated Jessica knew what was coming. Wanting to give her boyfriend as much pleasure as he'd given her, she used what little strength she had left to grab his cock with both hands and suck as hard as she could.
"Fuck!" Larry groaned as his cum erupted into Jess' mouth.
Jessica moaned in delight as hot cum coated her tongue. Her hand milked the hard cock in her mouth relentlessly. Larry's hips bucked wildly as he filled her mouth. Jessica swallowed hard and kept jerking his mammoth cock, but as violently as Larry's hips were bucking, his cock popped out of her mouth and a long rope of cum landed on her face. Then another landed in her hair and finally, one right across her lips.
Larry collapsed onto the floor in a heap. Jessica rolled over onto her back and licked the cum from her lips. As she lay there, utterly exhausted, with cum on her and inside her, she'd never felt so dirty. She'd also never felt so satisfied. In minutes, Larry had recovered and climbed back into the bed with his friend's girl.
He managed to fuck her six more times that night. Eventually, Jessica got under the covers and before Larry knew it she was out cold. Larry smiled as he got up and put his clothes back on. If he died tomorrow he'd die a happy man he thought as he closed the door behind him.
Much later, Nate made it back to the hotel room, totally wasted as well. He'd had a great night with his new friends and one hell of a streak of luck at the game. As happy as he was, he just didn't know how he was going to tell is girlfriend that he was a finalist in the tournament.
*** Present time ***
Larry was still thinking about his encounter with Jess when he noticed someone dropped a note under his bedroom door, he imagined it could be room service. Strangely enough, the person wouldn't even knock, and that got him a bit intrigued. He decided to check on the sender's identity and rushed to the door.
Unfortunately, by the time he opened it, the hallway was empty. He picked up the note, it wasn't even folded and it read "I know what you did, Higgs!"