Mr. Nice Guy vs. High School Ch. 02

Susan had had an idle fantasy about her stepson, if only because her husband was overweight and Jason was one of the most attractive men that Susan interacted with on a regular basis. She never considered making an actual pass at her husbands only son, but seeing the size of the cock in the video... maybe she should?

Then it dawned on her that her daughter had downloaded this footage and might be having the exact same thoughts. Lust quickly turned into anger as her maternal instincts kicked in, and she became furious that Jason would have sex in front of the cameras without thinking about who could be watching. Impulsively, Susan deleted the footage from the hard drive and making sure no other similar files had been downloaded, then turned off the computer. Storming up to the computer room where she and her husbands computers sat, Susan booted hers up and signed onto the security system's website. Since this was her house originally, Susan was the master user on the server, while Amy, Jason, and her husband were all guests. Susan revoked everyone's access but her own. After she had a moment to calm down, she accessed the video's login/logout reports that only she could see. Amy had accessed the video four times and downloaded it twice! This meant there would probably be a copy on her laptop. More interestingly, Jason had logged in and watched the footage and downloaded it once as well. So that is why he had sex in front of the cameras. Not wanting Jason to know Susan had seen what was going on, she reinstated Jason's access to the website. This way Jason might feel comfortable enough to make a few more home movies... what a wicked stepmother I am, Susan chided herself with a smile. Susan pulled up the footage again and started watching from the beginning. She still hadn't watched the whole thing, after all.

The more she thought about it, the more she felt she did need to find a way to tell Jason that Amy had seen the footage. She was not about to risk her marriage and her standing amongst everyone they both knew on making a pass at her husband's son, but maybe she could at least use this as an opportunity to bridge the gap between the two of them. Maybe open up their comfort zone a little, maybe open the way for a little more direct flirting, and with time... well... the cock in the video did look pretty big.

Jason frequently used the hot tub down by the boathouse at night, or went swimming in the pool. Next time Susan saw an opportunity, she would join him and try to work what she found on Amy's computer into the conversation. Susan slipped a hand between her thighs as she imagined how that conversation might go. She told him that she knew how men his age were, and that they had needs, but threaten him to keep his needs away from her baby girl. She would offer to help relieve him whenever his libido got the better of him if it helped him from taking advantage of her daughter. He would confess being a sex addict, and say that he would need Susan's assistance quite regularly. Then he would pull down his trunks and walk up to her slowly....

Removing her fingers from herself. She was going to far. She would be flirtatious at most, not a desperate whore. Even if Jason made a pass at her, she would have to say no. She couldn't risk her marriage on sex, no matter how hot the taboo. After Jason and the two girls left on the video, Susan walked over to where she kept her swimwear. She had swimsuits that would be more than adequate to draw the young man's eye, but this was to be a turning point one way or another, and that was as good an excuse as any to go shopping.

Susan logged off of the website and hopped in her SUV, and spent a good portion of the day buying clothes. She argued with the devil on her shoulder on how sexy bikini she should buy, and the scandalous little imp won out. Just because she was not going to make the first move, did not mean she could not be absurdly attractive bait. She would probably turn the kid down if he made a pass at her, but she would still welcome the attempt. Probably? Susan smiled at her complete lack of shame.

Susan went to the gym after her little shopping spree, and did what she could to work her frustrations out on the work out equipment at the gym. She really wished she was one of the lucky women who could bring themselves to climax when masturbating. It wasn't fair that she only got off while in bed with a man, and even then only a small percentage of the time. Once she got home she took a long shower and tried to get herself off by her own hand, but she didn't have any luck. Only after her shower water went cold did Susan step out to dry off. Peaking out the window, she saw her stepson was down at the boathouse, home from school. This meant Amy was home, and Susan had some parenting to do. She slipped on a thick woolen robe and sought out her daughter.

To her surprise, Amy was not alone when she opened her daughters bedroom door. Stacy and Becky were both present, huddled around the computer. Luckily, the theatre website was what they had pulled up. "Hi mom. We are only here for a minute, we are going to go watch a movie. Is that cool?"

"Of course dear. Have fun. I need to talk to you later, but it can wait. Nothing important."

"Okay mom. Love you!"

Well if Amy was going to be gone, maybe she could confront Jason then? Stepping back into the computer room, she pulled up the security cam to see if her son was alone. She would wait until Amy was gone, then go for a swim in her knew two piece and see if she could lure her stepson out of the boathouse. Only when the page loaded and she linked into the direct feed, Jason was not alone. The blonde from the day before laid on her back on the kitchen counter and Jason had his lips buried between her legs. Okay, she knew eighteen year old boys liked a lot of sex but this was ridiculous. People ate off of that counter for crying out loud!.

Still, there wasn't much else to do but watch. After she heard her daughter and her friends leave the house, Susan couldn't help but open her robe and explore her body with her hands. Today was different than the day before, Jason didn't seem to have sex with the slim blonde once. The two merely went down on each other repeatedly and made out for a bit. Eventually Jason made the girl what looked like spaghetti, and they ate dinner while watching a movie. After the meal her stepson and the blonde made out some more, then they got up and left. Susan heard the jeep pull away and she knew Jason was driving the girl home. She watched Jason get the little stick off at least four times with his tongue, and Susan hadn't been able to cum once all month!

***** A Date with the Pothead

After dropping Nicole off, Jason had to turn on the speed as he took off towards the mall. It was almost ten, and Shyla had been waiting for almost an hour for him since the mall closed. Turning his phone back on, Jason was shocked that Shyla had only sent him three text messages. The first one from eight o'clock read "I am at the mall, are we still on?" The next read "I am freezing." This came through at nine thirty. The second came at nine forty and read "Are you still coming?" It was now nine fifty five.

Not wanting to get stuck in a long texting conversation, Jason called her.

"I am on the way gorgeous. Are you still at the mall?"

"Y-y-yes. I am fr-fr-fr-fr-freezing." Shyla said.

"I am like five minutes away. We can hop in the hot tub first thing."

"Okay. I br-br-brought a change of clothes, a bowl, and a swim suit l-l-l-like you asked." Jason couldn't help but smile at how pitiful the petite girl sounded. Hanging up on her, he sped up a little more. Realistically he was fifteen minutes out, but he would try to shave some time off of that. When he pulled up to the mall parking garage he did not see Shyla at first, but when she came out of the stairwell Jason couldn't help but laugh out loud. She was wearing the clothes she had worn at school as well as what he guessed was the outfit for tomorrow. Suddenly her skimpy tops didn't look like such a bright idea. Before Jason let her into the jeep he made her take off the extra shirt and untie the jeans from around her waist, telling her that she looked kind of ridiculous. Feeling kind of like an asshole for making her strip in the cold (which was exactly why he had done it), Jason pulled her over to him and wrapped his arm around her to keep her warm, turning up the heat in his jeep to a comfortably high level. Jason didn't feel the girl up, but he did leave his hand on her bare stomach. Her skin was ice cold! The eighteen year old girl did have a little six pack going on, which Jason had noticed once or twice before at school.

Shyla told Jason just how bad her day had been, which lead to her telling him how bad her week had been, which lead to her telling him how much she was looking forward to hanging out with a descent guy. Like Nicole, Shyla talked a lot. Jason thought about taking his cock out and giving her mouth something better to do, but he liked the idea of Shyla not knowing that he wanted to sleep with her. It was obvious she wanted to sleep with him or she wouldn't have hung out in an empty parking garage for an hour. Once they got to Jason's neighborhood, Shyla was blown away by the houses. Apparently she had not ever been to this side of town before. It had already been dark and had been for a good four hours by the time Jason pulled up to the boathouse, so their was not really a lot to see as Jason walked Shyla up to the door and lead her inside. She smelled the left over spaghetti immediately and asked what it was. Jason told her she could feel free to heat up a bowl if she was hungry. He told her he would be waiting in the hot tub, and reminded her to bring the weed.

Jason was patient while he waited in the hot tub. The second floor of the boathouse was largely floor to ceiling windows, so he saw the upstairs lights come on while Shyla explored the building. Plenty of time passed for Shyla to reheat and eat a bowl of spaghetti, explore the house, and change. She must be taking some extra time to get warm before coming out side, that or seeing if she can get away with stealing anything, Jason reasoned. Eventually he heard the door open and Shyla came running around the corner with the bowl wearing a skimpy little yellow bikini. She all but fell into the hot water, settling down across from Jason. Jason turned on the jets and Shyla sat the bowl down and submerged herself in the water to get warm. The two started chatting about nothing; the approaching winter, school, Jason's cool boathouse, how good the spaghetti was. Once they started smoking Shyla came closer at Jason's insistence if only to make passing the bowl back and forth more convenient.

Jason was surprised and alarmed when the back door to the main house opened and someone started making their way down to the hot tub. While the hot tub was mostly enclosed, it was easy to see out do to the spacing of the slats that made up the walls. The person coming down the walk was too tall to be his sister, which only left his dad or step-mom. Jason had Shyla hide the bowl and they both made an effort to waive the smoke away, but there was no hiding the smell or the fact that they were both stoned. To his relief, it was his stepmother who stepped up to the tub's entrance. His dad would have been furious at the smell. His stepmother was twice a trophy wife, which was ironic since she had more money than Jason's dad. Her first husband had been elderly and left her with a fortune, as well as a pretty little daughter. Jason's dad had earned his own riches, and was considered kind of some financial genius. From what Jason understood the widow Mrs. Fitz had been concerned that she would blow through her dead husbands fortune, so she agreed to marry Jason's dad so long as he kept care of their finances and insured that she never wanted for anything. Thus the young widow Fitz became Mrs Fitz-Lakes, Jason's stepmother. She was not so much younger than Jason's dad that there was anything odd about the relationship; Jason's dad was 48 and his stepmother turned thirty seven in a few months. Their major difference was that where she spent her free days jogging, dancing, and working out at the gym, going to beauty salons, etc, Jason's dad spent his days sitting in an office and eating expensive meals. Jason's dad was getting kind of fat since the two had tied the knot, at least he looked fat compared to his stunning wife and his athletic son.

One of the first things Susan Fitz-Lakes did when her first husband had passed away was she bought herself a new pair of boobs, and Jason did not think the woman owned an outfit that did not show her new boobs off. She had caught Jason looking at them more than once, and if she ever acknowledged it at all it was just with a smile or a wink. Not that Jason would ever try to sleep with his father's new wife, but with some women you can not help but to look, no matter who they are married to. Jason kind of wanted a peak at what she was wearing under the white robe. Clearly she had planned on making some use of the often neglected hot tub. Jason's stepmom looked surprised to see that Jason had company. "Oh I am sorry, I really didn't mean to intrude. I saw my stepson down in the hot tub for once and I thought I should come down and have a word with him."

"Oh I can wait inside..." Shyla started. Jason's stepmother looked surprised by the offer, but not as surprised and irritated as Jason felt It was an odd response. Clearly Shyla had self esteem issues. Jason was also surprised that his stepmother had come down to join him at all, but was annoyed with the interruption. If she chose to join them, it might keep Jason from getting laid, at least for another hour or so.

"Don't be silly!" Both Jason and his Susan said on top of each other. Jason made introductions. "Shyla, this is my Dad's wife Susan, Susan this is Shyla, a friend from school."

"Nice to meet you." Susan said. "You know you can introduce me as your stepmother don't you. I wouldn't be offended."

"I feel uncomfortable calling someone who looks twenty five my mom." Jason said with a wink. He was clearly thinking with the wrong head, and needed to get it together. Still if he made her uncomfortable, maybe she would leave.

It took Susan a moment to recover. "Would this be one of the two young girls you have had over these passed two nights?" she asked.

How awkward a question was that? Jason smiled in spite of himself. In for a penny, in for a pound. "No actually, I just picked Shyla up an hour ago, and I have never really spoken to her before today. She offered to smoke me up if I let her spend the night. Wanna join us?" Jason reached behind him and grabbed the bowl from where it was hidden and offered it to his stepmother. He knew for a fact that she and her club friends smoked on occasion. On some of the nights when they would take over the boathouse the entire place would smell like weed. Susan declined, clearly offended.

"No thanks lover boy. Listen, if you two are planning on doing more than smoke, just make sure you use protection." Susan snapped. Without saying any goodbyes she turned and walked back up to the house. Maybe Jason had pushed her to hard.

"Awkward much?" Jason asked. Shyla nodded. "Look Shyla, about what Susan said, I don't want you to get the wrong idea. I don't want you to think that I rushed out and bought a bunch of condoms or anything." Jason said, as if to imply he had no intention of having sex with the little pothead beside him.

"Oh, okay then. I mean it is cool if you did, but I am cool just hanging out too."

"Don't get me wrong, I have every intention of fucking you tonight, I was just planning on fucking you bareback if that's cool?" Jason smiled at Shyla and she smiled just as brightly nodding.

"My dad makes sure that I am on the pill, so we can do whatever." She shrugged, struggling to seem nonchalant. Earlier, Jason had his cock in and out of a very different blonde's pretty little mouth, and not once had he been able to get into her tight little cunt. Pumping the little pothead full of his seed seemed like a great way to end a pretty descent day. 'You can do whatever' did not sound as enthusiastic as Jason could have hoped, but consent is consent after all. Besides, both new good and well that Shyla wanted Jason's cock inside of her.

"Take off your bottoms and come sit on my lap. We can finish off this weed and make out for a bit. Just hang them over the side there." Shyla slid the bottoms down her legs and hung the bottoms over the edge as she had been told. Doing so brought her bare ass out of the water and Jason reached over and gave it a squeeze. Shyla had an undeniably great ass. Once back under the water Shyla crawled over onto Jason's lap without once lifting her waist above the water line. She sat straddling Jason and he slid his hand behind her and squeezed her bare ass again, enjoying how it felt in his hand. She had an amazingly tight little ass, and it felt firm in his hands. She declined the bowl when he tried to hand it to her, so Jason sat it back down and pulled the girl in for their first kiss.

Shyla was an eager kisser, and very enthusiastic. What she lacked in skill she made up for with her obvious willingness to do anything Jason asked her to do, and then some. As they kissed Jason guided Shyla's hands to his rigid cock over top of his trunks and she eagerly started a gentle and teasing massage. Jason slid one of his hands down to free his cock and started rubbing her bare pussy with the back of one of his knuckles. Shyla's little hands wrapped around Jason's now bare cock under the heated water and started working his shaft up and down, squeezing it tightly. Shyla was having trouble multitasking between masturbating Jason, kissing him, and enjoying his finger against her clit, so Jason pressed her by sliding two fingers into her and devouring her lips with his, forcing her to surrender completely to the moment, and to Jason. Shyla was incredibly tight, even to Jason's fingers. His cock grew even harder in anticipation of sliding into such a tight little pussy. With his free hand, Jason pulled Shyla's bikini top free and pulled her tits up to his lips. She was small chested, though maybe a little bigger than Nicole, and as with Nicole her tits seemed all the more sensitive because of their smaller size. "Fuck fuck fuck fuck fuck fuck." Shyla whispered as she wrapped her arms around Jason and her hole body went tense. Jason was relatively new to bringing girls to orgasm, but it was always interesting to see how different girls would climax differently.

Jason stood up in the hot tub and stepped out of his trunks. This put his cock above the water line, and Shyla's eyes were definitely glued to it. Sitting back on the rim of the hot tub, Jason motioned Shyla forward for a closer look. Shyla didn't need any other direction to know what Jason was after. Gripping his big cock in her two little hands, Shyla took the head of his cock into her mouth for a french kiss. Where she seemed inexperienced with kissing, she certainly seemed to know how to give a good blowjob. Unlike most of the other blowjobs Jason had had, Shyla seemed to focus more on what she could do with her tongue. Jason picked up the bowl from where it sat beside the hot tub and took another long hit, and then another. Shyla looked up at him as she made out with his cock, never breaking eye contact as she alternated between giving his cock long licks or taking his head between her lips and massaging it with her tongue.

"The way I see it," Jason said, "for every single time you lied about whether or not we had sex, you owe me one night of doing letting me fuck you anyway I want." Jason bullshitted flirtatiously. Shyla nodded her consent, unable to talk do to the massive cock that slid in and out of her mouth. Pulling out of her mouth and slipping under the water, Jason pulled Shyla forward onto his lap, poised to take his cock into her tight little cunt. Learning from his mistake of taking Nicole roughly, Jason instructed Shyla to take him slowly. "Now I am bigger than most, and you seem tighter than most, so I want you to take your time. You have all night and all year to impress me, so feel free to go slow. Keep in mind you are going to have to fuck me again before school tomorrow, so don't get to sore."