Mr. Nice Guy Vs. the Mall Rat

For some reason in high school Jason had never really been popular, and as such he always assumed people or "popular people" thought he was a looser.

He was a big guy after all, at 6'5" he was tall for any age, and he worked out a fair amount, having played soccer his whole life, but that wasn't exactly a "jock sport" like football or basket ball. He wasn't even on the school team. His father was wealthy, and in his youth had been voted the most popular kid in his school, as had his step-mother. Likely, some day, his young step-sister would as well, since she had recently made the cheer team as a freshman.

Logistically, Jason should have been a pretty popular guy.

So why wasn't Jason popular? He was unreasonably shy. People would invite him to parties, and he would freeze, and over-analyze the invitation, worry weather it was a trick, why would the person want him there, would he enjoy it? People took his silence as intentional, and before Jason would muster up the courage to respond who ever had invited him would have given up and walked away.

Another problem was that Jason was naturally intelligent. He never studied, and rarely did any homework. In class he would never take notes, instead preferring to zone out and fill his notepads with art. Regardless of how hard he would try to slack off, he almost always aced his tests. His teacher's loved him, and would try to motivate him by bragging about him to the other students, or volunteer him to explain difficult concepts to the class. Jason hated feeling like a nerd, and he hated the attention.

He was also seen as too nice. Growing up, he had always stood up for the nerds against the jocks and bullies. This wasn't actually anything to do with caring about who was in the right or wrong, the bigger kids were just more fun to fight. No one else really knew about his real motivations though.

So all through high school Jason felt like a socially awkward nerd, and as such believed everyone else did too. So one year the most popular girl in the school, Mary, said he was REALLY cute and that she had wanted him to ask her out all semester. Over her shoulder, he literally saw her popular friends laughing at them. He may have been socially awkward, but he was no bodies fool. "Good luck with that." he told her sarcastically, shaking his head and walking away. Jason may not be cool, he reasoned to himself, but he was uncool on his own terms at least, no reason for him to fall for such embarrassing and obvious trickery.

So just before he turned 18, Jason went alone to watch this movie about becoming a spy. None of his friends had wanted to see it. The lead was challenged to get information from strangers, or get invited into their homes, while revealing nothing about himself. Jason was a self proclaimed student of psychology. While he had always been awkward about assuming what others thought of him, he had grown up watching others interact, and was pretty good at understanding how others thought or felt.

Jason reasoned that with enough planning and/or practice, he should be able to be like the guy in the movie, getting into peoples heads, saying the right things, earning trust, and all the while work himself passed his own mild agoraphobia. He would never have to fear what other people thought of him if he gained some control of that opinion.

Everyday that summer after seeing the movie Jason drove to the mall. He would sit against a wall and pick someone, a married man, an older woman, a family of three, a kid his own age, and watch them as they shopped or spoke to shopkeepers, maybe listen in on a phone conversation, and once he was ready he would "run into them" and just start up a conversation. For 90 days, 3 to 8 hours a day, Jason taught himself how to speak to people. He learned how to fake confidence at first, but as his successes mounted and his failures decreased, he grew to have legitimate confidence in himself. And he started making friends. A lot of them.

By his 18th birthday, Jason felt he was finally popular. At least at the mall.

He knew almost all of the mall-rats, and everything about them, who had dated who, who used what drug, who was a virgin, who was easy, who had a rough home life, and all they knew of him was his name, and Jason loved that they didnt seem to notice that they didn't know anything about him.

When they asked why he spent so much time talking to strangers he said he was learning to be social, which they took as a joke. The mall-rats never asked more than that. He even went to several parties by the end of that summer. By that point, people he didn't even know knew him by name.

****** The Mall Rat

One such party was held in an empty vacant apartment. Someone had jimmied the door and stayed a few nights, and decided it would be a great place for a party. There wasn't any power, so there wasn't any light either. He spent an hour talking to one guy, learning every detail about the guys life, when someone asked "Is that Jason I hear." The guy Jason had been talking to said "Who the fuck is Jason?" Jason, he decided about himself, was as skilled at being social as the guy in the spy movie. He hadn't even told this guy Kyle his name, and he knew more about him than most of Kyle's personal friends.

Later that night, Kyle's girlfriend, who was one of the mall-rats Jason kind of recognized walked off down the street from the party, and Jason soon caught up to her to ask what was wrong. Since Jason knew about their relationship problems from Kyle, it was easy to get her to open up. It didn't take too much encouragement before she told him all about how her 24 year old boyfriend wanted her to give up her virginity, especially now that she was 18, and how she really loved him but was scared to do so.

So Jason told her all sorts of generic B.S., if he loves you, he will wait, don't do it until it feels right, tell him to slow down or hit the road. That kind of thing. It was certainly the opposite of what his new friend Kyle would have wanted. He was ready to dump Kat if he didn't get some ass. But that was not appropriate advise for Jason to tell the girl. Plus, she was not exactly ugly and had a great rack, so Jason as a guy was not strongly motivated to help Kyle get some ass. Jason had the 'maybe if he dumps her I can hit it' mentality.

Eventually they got back to the party, and she left with her boyfriend. Kyle seemed none to pleased that she had walked off with another guy. Jason had a "sucks for you" attitude about it. The chic had been short, had a decent rack, and a revealing top. Jason, being 6'5" had had a great view walking beside her.

Then one day the following week, out of the blue, Kat brings in a batch of homemade brownies to the mall for Jason. Jason hadn't expected that at all. To the best of his knowledge she still had a boyfriend. Still, moving on instinct, he accepted the brownies and offered her a ride home. He had learned on their walk the week before that she usually walked home, because Kyle had wrecked her car and her dad worked second shift until passed midnight.

She agreed, and they exchanged numbers. He then returned to the conversation at hand while enjoying his brownies, sharing with no one, but completely blowing Kat off at the same time. This wasn't to be mean, but he had never "made a move before" and was worried that if he kept talking to her he would start being goofy about it and ruin his chances. Kat wasn't hot, but she was cute. She had dirty blonde hair that maybe could be washed more often, and was one of those girls who tried to hard to hide behind he rack. In fact her T shirt said squeezable across said chest.

Eventually the mall closed, and after texting Kat he spotted her standing patiently by a wall where she could see him. He said his goodbyes, then walked up and took her hand wordlessly leading her through the mall and to his car. Once inside, the silence was palpable, broken only by his questions about directions and her warmly spoken answers. He pulled up to her house and parked on the street.

***** The Flirting

"Thanks for the ride, that was really sweet of you." She said to him, looking at him with a blush.

Jason had never really had a girl look at him quite like that, but played it off as if he had been there a thousand times. "Thankful enough for a kiss?" She blushed deeply, and he turned his head and pointed towards his cheek patiently. Eventually, slowly, she leaned over and gave him a peck, followed by another thanks. He said "Wait here." as he hopped out of the car and walked around to her side opening the door and helping her out. "I'm going to walk you to the door."

She smiled and looked to the ground as he helped her out of the car, but didn't release his hand once she was out. 'Was it really this easy?' he thought to himself, amused by how much she seemed to be into him. "You don't have to do that." she said.

"Its only fair. You kissed me on the cheek as thanks for the ride, and I haven't gotten to thank you yet for the brownies. I think I will have to thank you the same way when I walk you to the door..." She seemed keen on that idea, and followed him willingly. He could tell by the way she smiled so broadly at the ground that she wanted Jason to kiss her.

Jason's mind was calculating what to say next, wondering how far he could take this...

On the porch, he waited for her to unlock the door, then he opened it for her and let her take a step inside. There she turned and presented her cheek to him and asked him for her 'thanks'. He smiled and shook his head. "You kissed my cheek for simply giving you a ride, and that was nothing. The brownies you made me were amazing! I think I can give you a better reward than that." He took her hands in his and pulled her against him, they made eye contact briefly, before he let his eyes trail down to her lips and waited.

Her lips parted for him, and her breathing picked up. Enjoying the feeling of her chest pressed against him, he teased her, leaning in for the kiss but pulling back every time she went for it, until finally he confidently said "Those brownies really were spectacular. I think I should come inside to give you this kiss." Her eyes went wide looking at him, and she looked over his shoulder as if checking to see if they were being watched. He didn't wait for her consent, but gently pushed her back into the hall and shut the door behind him.

Spying the kitchen down the hall he pulled her by the hand to the island counter and leaned himself against it, then he took her hands again and wrapped her arms around his neck and pulled her to him. He started teasing her again, keeping his lips just an inch from hers. He was teasing himself as much as he was teasing her. He had never kissed a girl before, all though she clearly didn't know that.

To her, he was the experienced lead. Really, he still hadn't really decided to kiss her at all. He liked knowing he could, and seeing how much he could make her want it, but he could still easily turn and walk away. She wasn't the hottest mall-rat, after all. He wasn't interested in her personality at all either, but she clearly dug him, and had such an appealingly large rack....

Inspired, he picked her up and spun in place sitting her ass on the island counter top. Her legs parted to either side of him simply because he was close enough to the counter that they had to. She was breathing heavily now. He brought his lips back towards hers, and rubbed the back of her head and neck before whispering "Can I kiss you?" That coy innocence broke her restraint, and she pulled him into her, wrapping and squeezing her legs around him and forcing her tongue down his throat. This was Jason's first kiss, although Kat still would have sworn he was more than experienced.

Kyle had never teased her like that, nor could she ever remember her heart beating faster. Jason's hands slid smoothly from her neck to her ass, ass to her jeans, and then slowly back up her shirt to squeeze her bra clad tits. Eventually Jason broke the kiss with a funny smile on his face, shaking his head.

"Whats so funny?" she asked breathlessly, hugging him to her.

"You didn't let me finish." He replied. "I wasn't asking to kiss your lips." His hands were still caressing her tits. He pinched them hard and held them firmly through her bra and she lost all the air in her lungs. Opening her mouth in shock, he began kissing her again, and as he released the grip on her tits, she got lost in the kiss once again, forgetting or forgiving the pain she had just felt.

She knew as soon as he unhooked her bra that she was in trouble, but she also wanted it off. Soon her shirt was on the floor next to it. His lips were very suddenly pulled from hers, only to latch onto her exposed nipples, sucking and licking them like there was no tomorrow.

Kyle had played with her tits before, but had never made her feel anything like what Jason was doing to her now. She leaned back on her arms, paralyzed with pleasure, and was overcome with a jolt of electricity when his hand suddenly pinched her pussy through her denim jeans. She sat upright to protest, but was met with his lips on hers again. Her hand grabbed his wrist with the intent of pulling it away from her pussy, but she could apply no pressure. The way his fingers rubbed her pussy through her shorts stole every ounce of strength she had.

'I can't let him take this further while I am still with Kyle. I want soooo badly to cum, and I think Jason could make me cum very easily, but I don't want my first time to be an affair! I can break up with Kyle tomorrow and invite Jason back, but I cant let Jason take my pants off!' Kat thought to herself.

As if reading her mind Jason whispered in her ear "I don't want to fuck you, I know your still a virgin, but this is how I want to thank you for the brownies. I want to kiss you right here." His hands continued to rub her crotch, and he could feel how hot and damp she was. "I want to lick this and kiss this and I want to taste you as you cum. Is it ok for me to take your pants off?"

Kat fell all the way back on the island. That wasn't fair! She had told Jason that first night about how Kyle never returned the oral favor when she went down on him, and Jason went on and on about how pleasurable it was to go down on a girl for both him and his women! She was mad at herself as she lifted her hips and undid her jeans. Kyle had never offered to go down on her, and she wanted to cum sooo bad!

She knew Jason would know what he was doing, and she wanted to climax right then more than anything! Soon she was naked on the island counter top in the kitchen, staring at the ceiling waiting to see what Mr.Perfect was going to do to her. She closed her eyes as she felt his hot breath on her pussy. He was an inch away, teasing her as he had with his kiss. She wanted to cry she wanted it so bad!

She was almost to the point of doing so when out of nowhere his fingertips started flicking quickly across her nipples, sending tiny jolts of electricity all across her body. She moaned and stretched her arms and legs. She rested her legs on Jason's back and as they pressed down on Jason's shoulders he ran his tongue firmly across her cunt.

Kat cussed! Jason smiled to himself as his hands continued to play with her nipples. He had, after all, just tasted his first cunt. And sucked on his first set of tits. And made out for the first time. 'How many firsts can I pull off tonight?' he wondered, as he carefully stimulated the outside of her left labia with his tongue.

He may not have experience, but he had grown up reading stories in magazines and online, and he never forgot anything he read. Now it was simply a matter of testing every trick he learned, and figuring out which ones worked best on Kat. He knew she liked to be teased, so he wasn't going to touch her clit until he knew it would make her cum. His tongue moved slowly in and around her slit while his fingers moved swiftly across her large nipples. Then at times, he would squeeze her tits firmly and work his tongue as swiftly as he could manage. It wasn't until her hands were trying to squeeze blood from his scalp that he clamped his hands hard onto her tits and put all the speed and skill he could into working her clit. She cried out, very audibly, kicking Jason in the back with both legs and he could feel his chin become very moist, very fast.

Once it was over, and he had lapped up his fill of her soaking wet pussy, he stood and pulled her up to a sitting position. He wiped the cum from his lips and chin, and pulled her in for a tender kiss. She melted into him. "Thank you." She whispered to him shyly, turning beat read. Jason felt very powerful just then, being completely clothed in a strangers home, while she blushed naked in front of him.

"You mean your welcome." Jason corrected. "That was my way of thanking you for the brownies after all, they were incredible."

She smiled at the idea of continuing the ruse. "No, what you just did to me was much more than incredible."

Jason looked off to the side as if deep in thought "If only there was some incredible way you could thank me then...." She smiled broadly as she began to unbutton his shirt.

"I am sure I can think of something." She smiled at him, and he kissed her passionately. But when he broke the kiss she stayed silent and looked to the floor...

"I just got you off with my lips and tongue and now you are shy? You told me you have gone down on guys before...." She had mentioned oral was the compromise for sex with Kyle. A frequent one, and all ways one way. Why was she shy now? She blushed. He said "No pressure, but I would REALLY appreciate the favor." He gently leaned her back with his hands and took her tits into his mouth again. It wasn't long before her breathing had picked back up and he could tell she was ready to do what he asked.

Jason picked her up off the table, and she wrapped her naked legs around his abs. He had her lifted high enough to keep his lips on her sensitive and overgrown tits, and his hands supported her ass as he carried her to the living room. She had to watch her head to keep it from hitting the ceiling. He sat down on the couch, and slid her down his chest to sit in his lap.

She was uncomfortable with straddling him since she was so turned on, so she quickly shifted down to the floor. He placed her hands on his lap, and they obediently started unsnapping his jeans and sliding down his zipper. She was extremely nervous, and even though she put her hands into his jeans and rubbed his cock, they stayed on the outside of his boxers. This was the second cock she had ever touched.

Jason didn't wait long before moving his hands from her chest to his own cock, pulling it free. She pulled her hands back from it on reflex, but he placed them back on his cock and held them there before she built up the courage to grip it on her own.

'Why am I so nervous?' she wondered to herself. It was because he had made her cum like she had never imagined, and she was worried she would do a bad job and that he would loose interest. Plus there was no question that this was more than innocent kissing, something that "just happened", with her hands stroking his cock and his hands needing her naked tits, she was officially cheating on her boyfriend. Not to mention he was soooo much bigger!

Once again, he seemed to read her mind and said "There is nothing to be nervous about. Have confidence, because I am looking forward to this, so I will enjoy it. If you are worried about it I can teach you what I like."

"What should i do?" she asked. She looked so insecure pumping his massive cock, almost like she feared it. Somehow, this only turned Jason on even more.

"Kiss it." he told her. His cock throbbed in her hands. Slowly, she lowered her lips and kissed the tip of his cock. It throbbed happily in response. "No, kiss it like this." He lifted her head to his and he kissed her passionately, yet teasingly. He sucked her lips into his mouth, one by one, and nibbled each. He swirled his tongue around hers before pulling back and pressing her head back down to his cock. She obeyed beautifully.