Mr. Nice Guy vs. High School Ch. 02

Shyla nodded, but her nervousness was clearly visible in her eyes. Taking Jason's cock in both hands, Shyla slipped Jason's head through her entrance easily enough, but after that every inch that Jason's cock slid into her was slow in coming, and understandably so. Shyla was incredibly tight. About five or six inches in the girl was obviously in pain. "Are you sure you are not a virgin?" Jason asked, suddenly suspicious. Shyla nodded without really opening her eyes. They were closed tight from the effort.

"Dad.. uh.. my ex, this is as deep as he usually goes."

"I am deep enough for now. Try sliding up and down to get used to my width a little before you take any more in." Shyla nodded and wrapped her arms around Jason's neck while slowly lifting herself back up so that only the head of Jason's steel hard cock was inside of her before she started to lower herself again, taking him no further than she already had before starting to lift up again. As she worked on taking him in, her breathing began to come more regularly and Jason supposed pain was being replaced by pleasure. "Whenever you are ready go ahead and take another inch in, and then start fucking just that much. Then take in the next inch whenever you are ready and so on." It was an agonizingly slow process for Jason who was accustomed to shoving his large cock into women forcefully, but the affect on Shyla was definitely worth the effort. Not that Jason was the one putting in any work, unless you counted sitting in a hot tub and coaxing the little pothead to try to take in just a little more, just a little more as too trying of a task.

Once Shyla was certain that their wasn't much cock left to take in she dropped herself the rest of the way onto his lap and bit down on Jason's shoulder really hard. Jason slid his hands up her legs and squeezed her tight little ass and whispered how proud he was that she was able to take his entire cock considering how tight she was. He thought she was crying, and the thought oddly turned Jason on even more. He was probably going to have to be as gentle with fucking Gretchen as small as that girl was, though at least she had a little weight on her. Mary would probably expect the courtesy of a gentle fuck as her do if Jason managed to get into her pants. Jason was annoyed at the prospect of having to take so much time before the fucking even really started with so many girls, and decided that was one of the benefits sleeping with older women provided. Shyla sat up and started kissing Jason frantically, tears really running down her cheeks. She certainly was acting like a virgin, Jason thought to himself as he played with her ass with his hands. At some point in time the Jacuzzi jets died off so Jason reached over and turned them back on.

Shyla was the one who said she wasn't a virgin, and Jason was certain he wouldn't have taken her virginity if he thought she was. With the amount of texts she had sent him after only flirting with her, she could easily turn obsessive if Jason was not careful. Jason decided to be a little mean just in case. "Shyla, I am letting you set the pace because of how tight you are," Jason said in a moderating tone, "but if you do not start working that little twat of yours I am going to take over and I will not be gentle with how hard I fuck you." Bringing her lips back to his, Shyla's hips again began to raise and lower themselves over his cock. As she rode him, a car drove up to the main house and and Jason spotted his stepsister and one of her friends got out of the car. Luckily, it looked like they were going inside. Shyla froze at the noise and looked over her shoulder to see if their outdoor activities had been discovered. Leaning in Jason whispered "I am not going to warn you again hot stuff." Shyla turned looking shocked, but Jason calmed her down with a winning smile. Again Jason's cock started sliding in and out of Shyla's pussy while both she and Jason watched the girls disappear into the main house.

Soon after they disappeared, Shyla asked if they could go back into the boathouse. Agreeing, Jason stood, and Shyla was forced to sink back down on to his cock and hold him with both arms and legs tightly to keep from falling. Buried as deeply as he was in Shyla's cunt, it wasn't hard to stay inside of her as he carried the tiny girl indoors.

As soon as they came in through the front door, Jason turned and pressed Shyla up against the wall. Holding her tight little ass, Jason picked up a pace only slightly faster than the one Shyla had set. Shyla's lips sought his and she kissed him with a hungry passion. Jason was turned on by her passion, but found the kissing kind of a distraction.

Once she seemed comfortable with his cock's size and girth, Jason carried her over to the kitchen counter and laid her down across it, like he had done with Nicole. Only Jason had no intention of wasting anytime on foreplay with Shyla. Jason only had to bend a little to keep his cock buried inside of the smaller girl. With his hands on her six pack, Jason supported his weight on the girls stomach as he began to fuck her slightly harder than before. Held down as she was, she could no longer kiss him, and she began to make funny noises as Jason pushed in and out of her. "Aw, ow, oh, eh, uh, oh, ah!" Amused, Jason picked up the pace a bit and the pitch and volume of the girls exertions picked up as well. The girl cried out as she came, switching from the random noises to an obscene list of curse words, all of which were incredibly amusing and arousing from a girl so petite.

"Fuck that was incredible," said the little blonde pothead, "you can do anything you want with me until you cum." And that was music to his ears. Jason pulled out of Shyla's cunt, picked the girl up and laid her face down on the floor in a location that placed her front a center for the living room's hidden camera, the same spot where he had positioned Nicole. Jason had not been able to enjoy much of what the home security system had recorded yet, but he did plan on spending any lonely nights looking everything over. Pulling Shyla's hips up into a doggy style position, Jason slid his cock back inside of her. Giving only a few short thrusts to make sure his cock was well lubricated, Jason leaned in and took hold of Shyla's arms by her elbows. Standing on his knees and buried inside of her, he pulled her up by her arms until her torso stuck out parallel to the ground, perpendicular from Jason's waist. "Don't drop me." She had time to say before Jason slid most of his cock out of her vagina and slammed it back home. The force of his thrust pushed Shyla away from him, but not off of him, and he hauled her roughly back against him by pulling on her arms, meeting her again with another hard thrust. "FUCK!" she yelled as Jason used the leverage he had on her to build up momentum with each hard thrust. Her already tight pussy clamped down on his cock from fear of being dropped, arousal, and her own sexual tension, and after a moment Jason found himself quickly approaching an orgasm of his own.

Should he cum inside of her? She said she was on the pill, but he already knew her for a liar. If what Jason guessed about her dear old dad was true, being on the pill would be likely, and he didn't think he was wrong. She had clearly said Dad earlier when she was talking about a cock, and she had told Jason earlier at school that she didn't want people to find out who had taken her virginity. Still, he might have been wrong. She certainly felt like a virgin to Jason. Annoyed that he couldn't trust the girl, he pulled her elbows together increasing the pain she felt in her arms as he continued to pull her roughly against him, and came deep down inside of her. She did have a boyfriend until recently, she had said. Maybe she was on the pill. As Jason's cock erupted into Shyla's tiny cunt she screamed, but not from pain. Her back bent at an odd angle as her orgasm quickly followed his. Angry that he had given into temptation and cum inside of her when he had no clue if she was really on the pill Jason released her arms and let her fall on her face.

Suppressing a laugh, Jason left her in a heap on the floor as he went to the boathouse shower to wash up. He was pleased to see that he didn't have any blood on his cock at least. He supposed he shouldn't care if Shyla had been a virgin or not. It was her business, and if she was a virgin and wanted him to know she could have told him. Once he was done washing up, he was pleased to see Shyla in the same position he had left her, totally spent. Jason picked the girl up and carried her upstairs to his bed and gently tucked her in. Getting dressed, he explained that he had some homework to do on the computer and would be turning in shortly. He told her to sleep well, because he would be fucking her again in the morning before she took her shower. She objected to needing a shower, which annoyed Jason a bit. He stressed that she would need a shower before school, but that it could wait until the morning.

***** The Stepmother's Night

Susan got dressed and spent about an hour cleaning the house. She heard Jason's jeep pull in, but she didn't let herself log on to check on him. She did log on to her daughter's laptop now that it was in the home and she quickly deleted what she hoped was the last downloaded recording that her daughter had of her stepson's threesome. She stood and happened to glance out the window and saw who she thought was her stepson stepping into the enclosed hot tub. The wood slats were on the enclosed hot tub were positioned so that you could see out much better than you could see in. Susan steadied her breathing. Now or never. Back in her room she put on the new skimpy little two piece bikini. It had just enough material to push her boobs together and cover her aureole and nothing more. She was fairly confident she would need to readjust the thing continuously to keep her nipple from peeping out. Then again, maybe she wouldn't bother. Slipping on the matching thong, she slipped on her new skimpy white silk robe and made her way down to the hot tub.

As it turned out not only was Jason not alone, but he had a completely different girl with him! And he was clearly stoned, so was the girl of course. This one looked completely embarrassed at being walked in on. What had they been doing before she came down? Completely embarrassed and unwilling to let Jason's female guest see what she had chosen to wear under her robe, Susan made her polite introductions and walked back up to the main hose empty handed. Embarrassment lead to frustration, which lead to irritation. So Jason was choosing quantity over quality was he? Rookie mistake. Did he know what he was missing out on? Back in her bedroom, Susan took a moment to look at herself naked in the mirror while she changed. That young man should be begging to spend alone time with Susan, regardless of who she was married to. Well Susan was an experienced predator, and she knew how to bide her time. This new short haired blonde wouldn't be there all night after all. Back at the computer Susan watched Jason carry this new girl inside and have sex with her all over the house. When Jason laid the girl down on the kitchen counter, Susan realized that he was intentionally fucking the little hood rat in every location that he and the longer haired blonde had fooled around just a couple of hours ago, though Susan was surprised at how aggressive and rough her stepson was being with such a small girl. After he was done with her he left her in a pile on the floor as he went to take a shower. Instead of taking this one home though, Jason carried her exhausted little form up to his bedroom, exiting only long enough to lock up the hot tub and turn the lights off in the house and grab his backpack from where it lay by the door downstairs. Susan was incredibly turned on and frustrated.

Susan's daughter came home, but unfortunately Becky would be spending the night, and this was not going to be the kind of confrontation which should be done with witnesses. Susan decided to put the confrontation off another day. Yet another thing to be frustrated about. Hadn't she married a financial wiz so that she could live a stress free life? She should have married a man with an ugly son.

From Amy's point of view, she had invited Becky to come over for a minute so they could watch the video again and see if her brother had anymore company. The girls had to stay behind after school for cheerleader practice, and Becky was fairly sure she had seen Nicole slip into Jason's jeep after most of the school had cleared out. The two girls were surprised and confused when the video was deleted from the desktop, and even more surprised when it was no longer on the laptop. When she tried to sign into the website, she was denied access. That's when Amy figured it all out. Mom knows! She had to. Explaining the situation to Becky, Amy convinced her friend to stay the night just before her mom came in looking red in the face and wanting to talk. "It can wait until tomorrow. We need to talk alone though, so no company and come home straight after school.

Susan logged back onto the security website and hadn't even noticed her husband had come home. She was certainly glad that she hadn't been masturbating or naked when he sat down at his computer. As seductively as she could, she lured her husband up to their marital bed. Susan had a lot on her mind, and she desperately needed to climax before she made any decisions she would regret.

Unfortunately for her, this was one of the many nights her husband fell asleep leaving her wanting for release.