Mr. Nice Guy vs. High School Ch. 02

"Um.... okay." Shyla said slowly. Had she just heard him right? Did he just say he wouldn't mind hooking up with her for real? She immediately thought that she had to have misheard. He had said that far to casually for him to have said what she thought he had said. She focused on the part that made sense, the part where he had needed something from her. She assured him she could get anything he wanted and asked how much she needed to get for him.

"Good. Now I don't know how much I will need, because I do not know how many are coming or how many of the people coming will want to smoke. I would rather error on the side of caution though and buy more than I need. You can always come over the next week and help me smoke off what is left." Jason winked at her. He had not planned on flirting with the girl. He had planned on giving her attitude and demanding she make up for her deciept by hooking him up with smokes for the party, but she seemed so guarded and timid that dominating her seemed to easy, and her reasoning for her lies seemed harmless enough. Besides, it was always more beneficial and fun to flirt with pretty girls than to yell at them.

'WTF?' Shyla thought, 'is he actually flirting with me? Did he just invite me to his place next week?' Nodding, Shyla assured him that she could get him whatever he needed.

"Great. Give me your number and I will keep in touch on how much I am going to need. Here, take mine in case you need to reach me. Now I have to go, I am taking Mary to lunch." No reason not to feed that rumor about he and Mary on his own now. Obviously Mary wanted people to believe that she and Jason were an item. Plus, if Shyla believed the rumors Mary said were true, then that reinforced her impression of him being well equipped sexually. Jason was well equipped, but so far rumors about him were all based off of gossip. Impulsively, Jason kissed Shyla on the cheek before heading out to the school parking lot. As he walked away he was glad that he had kissed her, because the look on her face made it obvious how badly he had confused the troubled pothead. He didn't go back into the school, so he did not notice all of the stoners huddled just inside the entrance staring at he and Shyla.

***** The Lunch with Mary

Mary was waiting for him when he got to his jeep. She was sitting on the passenger side with a completely blank expression. "I am not used to people making demands on my time, or keeping me waiting." She said as he hopped in. She didn't look annoyed, she looked defensive.

"Sorry hot stuff. Let me make it up to you. Where would you like to eat? My treat and anywhere is fine with me." She picked a little Mexican place called Cancun without hesitation. Jason had never been there, since it was pricey, but he heard the food was good. Jason's phone kept buzzing on the drive, but Jason ignored it until he got out of the car. They were all texts from Shyla.

"So what was that remark about regretting that we haven't hooked up? Were you being serious about that?" "Forget I asked, just let me know how much stuff you need." "Hey, did you mean it when you said I could come smoke with you?" "Would Mary be okay with that?"

Jason texted Shyla back before walking Mary to the door, holding it open for her. "Of course I meant it, and Mary would kill you." Jason hedged. "I am pretty busy right now and I have plans after school. How late will you be up tonight?" Jason didn't mind flirting with Shyla through texts, but now was not the time, and after school he had a date with the ever possessive Nicole. He wouldn't really be free to text until around eight or nine.

At the restaurant, Jason and Mary were seated immediately, and Jason had just started looking over the menu when his phone buzzed again. Mary looked pointedly at the phone, apparently she thought it was rude of him to be getting texts while they ate. So did she think of this as a date? Jason picked up the phone and was fairly surprised by the text. Shyla said "I don't have to be home tonight at all really as long as I show up to school tomorrow. How late do you need me to stay out?" That wasn't what he had meant when he asked how late she would be up, but Jason didn't see any reason not to take advantage of her response. He apologized to Mary, telling her the texts were about the party.

Texting Shyla back, he said "You don't have to be home at all? Can you find something to do till around nine thirty to ten then? I can pick you up when I and done with my errands. We can smoke in the hot tub and talk more tonight if you want. Bring something to smoke and a change of cloths for tomorrow and I will just drive you into school in the morning. I have to go right now. Talk to you later." Jason made a show of turning off his phone for Mary's benefit.

The waiter came and took their orders before the two started talking. "So... thanks for not calling me out back at school." She admitted hesitantly. She clearly had not wanted to apologize, since it put the ball openly in Jason's court. Not that it really mattered, Jason had the advantage already.

"You are absolutely gorgeous Mary. If you want people to think we are sleeping together, who am I to disagree?" Mary really was gorgeous. You kind of had to be to be popular. Mary had raven dark hair that fell down past her shoulders, and the body of a model. Literally....the body of a model! It was common knowledge that Mary and a few of the other popular girls did some modeling. Mary was tall and slim, with long legs and curves in all the right places and a very pretty face. If Jason pulled off sleeping with Mary, she would easily be the hottest girl he had slept with to date, and probably for quite some time.

"If you think I am gorgeous, why did you turn me down when I asked you out?"

Jason looked at her apologetically for a moment. "Their were like fifty people watching and giggling. At the time I thought it was some weird gag at my expense."

Mary looked down at the table. "It was." Jason was actually surprised. With everything that had happened this year and everything he had learned he had started to think her asking him out may have been legitimate. "Bridgette and Bambi were making fun of me for breaking up with this guy for having a tiny pecker. At the time, everyone kind of made fun of you for sleeping with some skanky pothead. Everyone knew you had a decent... you know, so they said I should go and save you from the skank and make your day by asking you out, since size was apparently a big deal for me. I really was up for going out with you, kinda, but the situation was kind of at your expense. It was at my expense, too, I guess, although I didn't get that until later. 'The size queen gets shut down.' That is what they said when you turned me down."

"Ouch." Jason said sincerely. "Okay, so why the rumor about the two of us hooking up?"

Mary looked surprised. "I always thought you made that up." she said. "At least I didn't make it up, I just heard about the rumor about you and I and decided to run with it. You turned me down pretty harshly. I am not used to getting made fun of as the girl who isn't good enough for someone. So I told a few people that we were sleeping together, that I had seduced you after you and I were alone. I meant to imply that it was a one time hook up, but the rumor got out of hand and..." Mary trailed off.

The food arrived, but before they ate Jason wanted to finish up what he saw as important. He was about to ask out one of the most popular girls in the school, after all. "That is what rumors do, they get out of hand. Listen, I was flattered when you asked me out, but it felt like a gag to me so I got kind of defensive and overreacted. I am sorry. Any guy would be lucky to go out with you. Your secret really is safe with me. I would love for you to come to my party, as long as it isn't too awkward for you. If you come though, you are not allowed to bring a date. You are more than welcome to be my date, but that is up to you. You can sleep in my room with me if you want to keep the rumor going but you do not have to have sex with me of course." Jason added hastily when Mary looked affronted. "I can sleep on the floor. I would rather not..." Jason winked, "but that will be your call that night. Sound good?"

Mary looked at him for a moment. Thinking to herself, she started eating, clearly lost in thought. Jason waited and watched her eat. Finally she smiled and said "I look forward to our second date, Jason Lakes."

"Second date?" Jason asked. Mary motioned around the restaurant they were in and Jason couldn't help but laugh. Apparently asking Mary out had actually been so easy they were already out. Jason realized that he had never been on a real date before, and he tried not to let it show on his face. "Maybe the party could be a third date," Mary continued, "if you wanna go to dinner and a movie sometime next week?" Mary asked, "I mean, if you and I are going to act like we have been screwing for years, we should probably know a little about each other first."

Jason smiled. "Sounds good, what day?"

The two enjoyed their meal as they made their plans and chatted. Mary told him all about what her life was like. Jason was vague about his, since his mostly involved having sex with as many women as possible he did not think it was appropriate to talk too much about the details. Some things should generally go unsaid. Jason not only got the restaurant door for Mary as well as the door to his jeep, but also put the seat belt on her as an excuse to lean across her flirtatiously. They held hands as he drove them back to school and once there they sat in the jeep and talked until third period ended. When he got out she waited for him to open her door. He kissed her on the cheek, slipping an arm around her waist before walking her inside. Taking a chance, he made a show of smacking her ass as she left him to go to class. People noticed, and they also noticed Mary's smile as she turned to flip him off flirtatiously.

Jason turned on his phone as he walked to his final class and the texts Shyla had been sending him while he was out with Mary came pouring in. "You have a hot tub?" "Should I bring a swimsuit?" "Sorry that was a really dumb question." "You have no idea how good this sounds, I have had a horrible week." "The mall closes at nine, but I don't mind waiting around the parking garage, just text me if you change your mind and I will head home". "It gets cold, so don't forget about me!" "Hello?"

"I won't forget! Calm down, be cool. Bring a swimsuit and clothes for tomorrow and some weed. I will see you later tonight okay?"

"Yeah" she texted back. "Whatever. See you later."

Whatever? Had he offended her? Well he couldn't really ask if he had without starting another tirade of texts, so Jason put his phone back in his pocket as he slipped into fourth period.

Bambi was in his fourth period class. Part of the reason he had wanted to skip fourth was so that Bambi would see he was missing and later piece together that Mary had skipped her class as well, but it worked out better for Jason that he made it to fourth. As soon as he sat down Bambi bounced over to sit by him, which she had never done before, and started talking to him about the party. In under four hours her guest list was already thirty-four people long and still growing. She hadn't invited everyone she planned on inviting yet, but several girls had either already confirmed plus ones or given Bambi and Julia a list of what they wanted Jason to buy. Jason didn't recognize all of the names, but the ones he did recognize were all some of the most attractive guys and girls at the school. Better yet, the guys offered to chip in, offering to bring a keg, steaks and hot dogs, chips... Jason told Bambi that if she wanted to organize what people brought that would be fine but he wanted to stay in the loop. It seemed like it was exactly what she wanted to hear, and she didn't mind at all when Jason's hand found its way to the small of her back as he leaned over to review the list peek down at her impressive rack. Bambi was certainly another one of the hottest girls in his school.

***** Jason and Nicole's First Solo Date

School ended with the fourth period bell, and after exchanging numbers with Bambi (for party preparation purposes of course) Jason waited in his jeep until most of the other students had gone before Nicole came out of the building. Smiling brightly and looking incredibly innocent in her Sunday best. Both she and Jason knew perfectly well that they would be spending the rest of the day trying to see how many times they could make each other cum. Nicole hopped in and, looking over her shoulder at the school, said "I don't think anybody saw me, but maybe I should keep my head down until we get to your place?" Looking out the window as she was, she did not acknowledge the fact that her hand was rubbing Jason's cock through his jeans. Looking at him innocently, she added "My oral fixation is really bugging me today, do you have anything I can suck on while you drive?"

Jason smirked as he pulled his cock out through his fly, and his smile broadened when his cock disappeared slowly between the pretty blonde's lips. Starting the car, Jason made no illusions towards being in a hurry to get home. After all of the flirting with Shyla, Mary, and finally Bambi, Jason was grateful to have his hard-on taken care of. Running his hand through her waist-length blonde hair, Jason forced himself to drive slowly, if not so slow that he actually might cum. What was the point in cumming quickly? They had hours before either of them had to be anywhere.

Parking down by the boathouse, Jason tucked himself in before circling the car to open Nicole's door for her and held her hand as he walked her inside. As soon as the door was shut, Jason pressed Nicole against the interior wall and slowly kissed his way down her neck with his hands pressed firmly against the wall on either side of her. He didn't stop kissing his way down her body until he was on his knees in front of her. "My goal today is to see how many times I can get you to cum while only using my lips, remember? Care to take off that dress for me?" Nicole shivered as she pulled the dress over her head and hung it on the front door. Jason stood and waited as she took off her bra and panties for him as well. Resuming his oral attention, Jason kissed his way back down her body, starting once again with her neck, but this time proceeded more slowly. Jason paid special attention to her nipples, knowing from experience that Nicole's were specifically sensitive. He took his time kissing his way down to her pussy, going slower the lower his lips traveled. He licked the outside of her pussy with two sensuously slow licks before dragging the tip of his tongue along her outer labia.

Nicole was tall and thin, and Jason easily lifted her pretty legs up onto his shoulders as he explored her sweet little pussy. He stayed on his knees until she came. Nicole was full of sweet and encouraging comments, which were a stark contrast to her normally controlling demeanor. "Oh thats it baby, of yes right there! Oh shit how do you know how to do that? Good boy good boy right there for mama yes!" After her climax subsided Jason carried her over to the kitchen, lying her back on the elevated counter before starting in on her pussy again. Nicole had been having lesbian sex with Gretchen for sometime, and Jason did not want to be outdone, even if it was by a woman. Jason kept her on the counter until she came twice more, and even then kept her there while he went to grab some ice from the freezer. He rubbed a piece of ice slowly and sensuously across his naked girlfriend's body, lapping the water trails up with his much warmer mouth. Once the ice was mostly melted, Jason trailed the shrinking piece down to Nicole's pussy, circling her clit several times before slipping it inside. Nicole's body writhed from the intense cold, and Jason obliged her protests by warming her clit with his lips and slipping two fingers inside of her until she came again.

Picking her up and carrying her to the couch, Jason positioned her so that she was standing up, bending over the couch at the waist. Standing behind her, Jason started to remove his pants and was surprised when Nicole quickly spun around into a sitting position. "You were way to rough with me with that giant cock yesterday, so it is going to be a few days before you can fuck me with it again. We are just going to have to stick to oral today." As always, Nicole spoke in a way that left no room for argument. Jason had been looking forward to fucking Nicole again almost as soon as she slipped off of his cock the night before, and he had been looking forward to this all day.

Frustrated, Jason grabbed his girlfriend's head and almost as soon as his cock slipped between her lips and forced his cock as deep as he could manage. Nicole gagged, and Jason instinctively pulled back out so that she could breathe, but Nicole held his ass from sliding away with her hands. Accepting her willingness to let Jason forcefully deep-throat her as an apology for the lack of sex Jason would be getting, Jason took full advantage of the situation and fucked her mouth as roughly as he felt she could handle, pulling out only when her gagging forced him to do so, then picking right back up where he left off. As frustrated as he was with her, he let himself imagine it was Mary's face he was fucking, then Shyla's, Gretchen's, and finally as he came he pictured himself shoving his cock down Bambi's throat. The little christian girl who was actually sucking Jason's cock managed to swallow his entire load, which had been building up for hours.

Nicole fell back against the couch with a smile on her face and Jason couldn't help but smile over her beautiful body. It was amazing to think of how different his life was now compared to a few months ago. This time last year he would have spent the afternoon working out or playing video games, probably both. To show his appreciation to the beautiful blond, Jason retrieved a bottled water for his secret girlfriend and offered to cook her a Spaghetti dinner. She agreed whole-heartedly, expressing her surprise that Jason could cook. They ate in the in their underwear, and after the meal Jason could not resist going down on the pretty blonde right in front of the hidden security camera, planning on coming back later to watch the footage. Jason still had no idea that he was not the only one to watch the recordings.

***** The Stepmother's Day

Jason's stepmother, formally Mrs Susan Fitz-Lakes, had had a very crazy and upsetting day. Do to her newest husband's financial expertise, she did not even have to pretend to pursue a career, and so she was free to spend the early portion of the day doing what she always did best, nosing into her daughters private life. Booting up her daughters computer, Susan spent some time nosing through emails and web history before noticing that Amy had accessed the IP address of the home security camera system the night before. Thinking nothing of it, Susan moved on in her prying which eventually lead her to check on her daughter's recent downloads, one of which was a large video file from the security website. Curiosity peaked, it only took the click of a button to open up the file. What she saw shocked her, and she liked to think of herself as experienced in the ways of the world.

Apparently her stepson was not only sexually active, but quite the lady's man. The video showed him having sex with not one, but two of his fellow classmates, neither of which looked unattractive in the video. Her stepson had always been an attractive and well built young man, and he never seemed uncomfortable with the innocent flirting she had done with him, always seeming to be unsure as to whether or not her teasing was intentional. Was the naive innocence an act? He certainly looked like he knew what he was doing with these two girls. Was his playing naive part of his game, and if so, did that mean he was actually running game on Susan? She had only been teasing for fun.