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.