Mr. Nice Guy vs. High School Ch. 03

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Mar 9, 2023 // By:analsex // No Comment

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*****The Recap*****

Jason didn’t really consider himself a good person, but he still tried to be a nice guy. He was friendly after all, and seldom rude. He would often go out of his way for others, even going so far as to getting into fist fights to defend people he barely knew. The truth of the matter was that he had done those things because helping people out seemed like a reasonable path to being liked and fighting was always fun for Jason, win or lose. In truth, as long as he was happy, Jason usually couldn’t care less about anything at all. Having been uncomfortably shy around girls growing up, Jason had largely abstained from the rest of the world, focusing entirely on his grades and staying in shape, and even that was do to pressure from his father.

Being a young, eighteen year old male, Jason had a strong fixation on the fairer sex, and a strong desire to have sex as often as possible. Now that fortune seemed to be smiling on him and he had suddenly learned how many women were willing to find their way into his bed, he saw no reason not to take full advantage of each opportunity.

To recap, the opportunity to sleep with Kat had pretty much fallen into his lap, a side affect of casual flirtation that the girl seemed to take to heart, and, like any single, young male, he took advantage of the willing virgin. Over the next few months he was essentially picked up by a cougar named Connie at a concert, and later seduced Donna, the married mother of one of his stepsister’s friends.

For quite some time he had maintained sexual relationships with Donna and Kat, but this week his luck seemed to be really picking up. He had sought out his long neglected friend Gretchen for advice about some rumors he had heard and to try and find out what girls at school really thought of him. Gretchen expressed a certain attraction for Jason, and over the following twenty four hours Jason somehow ended up in a polyamorous relationship with Gretchen and her amoral and bisexual friend Nicole. His relationship with the two girls was meant to be secret, the girls not wanting his bad boy reputation to sully their good Christian reps. The following day Jason made a pass at Mary, one of the prettiest and most popular girls at his school, and in passing flirted with Shyla, a skinny little pothead. By the end of the day he had a date scheduled with Mary and had ended up luring Shyla back to his place.

Shyla had gotten the chance to find out how well hung Jason truly was just last night, and was in the middle of finding out again this morning. Shyla has been a surprisingly heavy sleeper. Jason’s alarm hadn’t woken her up, nor had the oral attentions he had given to her smallish tits and tiny trimmed cunt. She had moaned, signed and cursed, but that Jason could tell she had stayed asleep through his patient ministrations. She hadn’t even woken up when Jason lifted her legs in the air and held them in place above her head while he lined his cock up with her extremely wet little cunt, but she sure as hell woke up when he pressed himself deep inside of her already overworked pussy. “Fuck!” she cried, “Give a girl a little warning will you?”

Jason apologized with a shrug before taking his morning hard-on out on the tiny blond. For the first time in his limited sexual career, he truly did not try to do anything fancy, he didn’t try to overwhelm the girl with over-stimulation or impress her with his sexual ability. He just fucked her as hard and as fast as he could manage. Pride forced him to wait until she came before filling her pussy with his cum. With a smile he kissed her deeply as their heart rates settled down. Shyla wanted to go back to sleep, but he kicked her out of bed and told her to take a shower, all with the same self-satisfied smile on his face. The girl had an unfortunate habit of not showering before school, and it was in her best interest to get cleaned up after the sex she’d had this morning and the night before. Jason had showered sometime after dropping Shyla’s half-conscious little body into his room last night, and while he wouldn’t mind one again this morning there just wouldn’t be time. As such, he had been careful this morning not to break a sweat.

As Jason got dressed, his mind wondered about his recent success with women. Part of it was surely due to the stories Shyla and then Mary had invented about how great he was in the sack, and part of it would be due to his physical attractiveness, maybe another decent percentage based off of his recently developed people skills, but he supposed part of it was his willingness to jump at the opportunities that presented themselves. Would anyone have invited Shyla, the skinny little pot head, back to their place for a shag the second they realized that she was interested? She was pretty enough that he was certain plenty of guys would have thought about it, and realistically several probably had, but he wondered how many people differentiated between can and should. Jason didn’t really have a specific type of girl that he was attracted to. He took just as Ankara bayan escort much pleasure from fucking a sexy cougar as he did fucking a needy pot head, an outwardly uptight Christian, or an average looking housewife; some girls just required more work to get naked than others. In just the few short months since Jason had lost his virginity, he had fucked tall women and short women, thick women and thin women, girls with large boobs and small ones, blonds and brunettes…. It suddenly occurred to Jason that he had never had sex with a red head.

Once Shyla was dressed, Jason walked her out to his jeep and the two set out for school. On the way, he prattled on to Shyla about the importance of keeping their new found sexual relationship a secret. He didn’t mind legitimizing the rumor that the two had had sex at one point, but he said he didn’t want their current affair to ruin what he had going on with Mary. Shyla believed that Jason and Mary had been an physical item for years, thanks to a rumor that Mary had started, but the reality was Jason had only built up the nerve to ask her out the day before. Their second date was planned for the upcoming Saturday night. A date that would follow up a day spent with his other girlfriends Nicole and Gretchen. Today was Thursday, and in all likelihood was destined to be an uneventful day.

***** Thursday at School *****

Before getting out of the car, Shyla offered Jason the rest of her weed, for him to smoke while she made arrangements to get enough for Jason’s big party. Jason rewarded the generosity with a kiss, a deep one that took her by surprise. She got out of his car with a warm blush coloring her face, and Jason wondered at how beautiful the blonde suddenly looked to him. Writing it off as post-coital afterglow, Jason hopped out of his jeep and headed inside. This time at least, his sister and company were not hiding in wait by his preferred door. Jason’s classes were, for the most part, predictably uneventful, and he spent a good part of the day trying to think of a way to get any of the redheads in his life into bed. Jason spent his time between his first and second period class talking to Mary, Julia, and Bambi about the upcoming party, parties they had been to, and what he should expect to occur at his place.

During the break between second and third Jason was able to get Mary alone, and he held her hand as they stood and chatted about when and where Jason would be picking her up Saturday night. Between third and fourth periods, Jason left Mary alone for fear of seeming clingy and, with nothing better to do, he ducked in to his fourth period class early. He was surprised when Bambi came in early as well and even more so when she took a seat beside him for the second day in a row.

The class was a Biology class, and as such, the tables were large enough for three students to sit side by side on stools with their work out in front of them. Each table had its own sink and drawers which held beakers, slides, and microscopes, none of which had been used in class as of yet. Bambi was a blond, blue eyed, busty cheerleader, and anyone in class would have competed to sit beside her any day of the week. The same could be said for Amber, the other cheerleader in the class. She was tall, with long, beautiful and natural red hair, with a firm set of tits and long legs, and Jason was pleasantly surprised when she came to join Jason and Bambi in the back of the class.

“Hi Jason, I’m Amber.” the redhead said, sitting down on the other side of him.

“Amber has a lot of experience in putting our parties together, so I asked her to help get everything organized?” While not technically worded as a question, Bambi’s tone asked Jason if he minded that Amber had been brought in. Jason assured them both that he didn’t mind at all.

Amber smiled, clearly pleased. “I am looking forward to helping out, plus I have always wanted to get to know Mary’s mystery boy-toy.”

“Amber!” Bambi said in a mockingly shocked voice, putting both hands on her face like the little boy from Home Alone.

“Mary’s boy-toy?” Jason said in a jokingly defensive tone. Bambi herself had called him that yesterday. Maybe he should ask Mary about the details surrounding the rumors she had spread about him. Making the most out of the opportunity, Jason slid his hand around Bambi’s waist and pulled her massive boobs against him in a hug. “I am my own man, thank you very much.” Jason winked at Amber conspiratorially.

Amber laughed and made a whipping motion and noise. “The way I hear it, Mary has you on a short leash. If I am to believe she exaggerated about that, I wonder what else she has exaggerated.” Amber mockingly raised an eyebrow and glanced down at Jason’s slacks. She meant for the gesture to be a tease, but her eyes locked on the erection that was outlined through the thin material of his dress pants. It hadn’t been there a minute ago, but Jason’s mind was exploring all sorts of the possible things he would like to do to the two cheerleaders.

Class Escort bayan Ankara started, and even though Jason released his hold on Bambi, she did not scoot away. When the class started, the teacher turned the lights off and put a slide show onto the overhead projector. Sitting in the back of the class with the lights out, Jason was able to spend the entire period whispering with the two hottest girls in class about the details of his would-be party and trying to describe what his place looked like to them. All through class Jason would discretely sneak peeks down Bambi’s generous top and at Amber’s figure, and when conversation provided he would find one excuse or another to touch the girls in some way. He would lay his hand on the small of their backs as he whispered to them, or put his hand on their waists if they leaned across him to whisper to each other. He tried to do so casually, as if to get them used to him touching them, to make them comfortable and to act as if they were all close friends. In return, both Amber and Bambi would casually place their hands on his arms or legs when they spoke, and Bambi’s hand remained on his leg for a good deal of the class period.

After class, Amber asked if she and Bambi could just swing by sometime or if Mary would need to chaperone. Jason flirtatiously replied that the two girls were welcome at his place anytime, unless they needed Mary to protect them, making sure to wink at Bambi. He was pleased when the busty cheerleader blushed. He had been expecting a smile and a head shake at best.

***** A Long Day at Work *****

Jason realized he was probably going to go without sex that day. Unless his boss Mrs. Rhea got him alone at work, he hadn’t made any plans, definite or otherwise, with any of the women in his life. Shyla had sent him a thousand texts at school asking if she could spend another night with him, but Jason didn’t want to get her accustomed to the idea staying with him on a regular basis.

He tried calling Kat to see if she would be up for something when he got off from work, but she told him her dad would be home that night and he would never let her out of the house that late. He had plans with Nicole, Gretchen, and Mary that Saturday, so he didn’t want to seem needy by asking them to hang out either, so Jason resigned himself to a lonely night.

Fortunately for him, his boss turned out to be in one of her moods. The first time Jason had gotten into Donna’s pants, she had been pretty reluctant about committing to the affair. Jason had had to take a dominant role in order for her to feel comfortable enough to give way to her more base sexual needs.

Once she had become his employer however, all of that had changed. In the first two months that he had worked at the grocery store, Donna had been outwardly hard on him. She had all but cut him off sexually so he could not even work his frustration out on her. To everyone else Jason had gotten the job by being friends with the boss’s daughter, as that was Donna’s excuse for insisting that Jason be hired above all others and on a fluffed up income at that.

It was because of that potential favoritism that Donna assigned all the crap jobs to Jason during his first few months of employment, and outwardly distanced herself from him. Jason proved to the other mangers that he had potential in spite of the extra workload, which made Jason fast track material, and as soon as he had proven himself an asset to the rest of the management team he was promoted to book keeper, which was sort of a supervisor oriented position. Book keepers handled money pulls and the front desk which would free up whichever manager was on duty to supervise the entire store. On most weeknights, there was one book keeper and one manager. That night he and Donna were closing together.

Donna often kept herself sequestered in the manager’s office during the bulk of her shifts. The manager’s office was a small room near the front of the store with a large two way mirror facing the registers, so you could work on more important things while watching the floor staff handle customers without you. “More important things”, Jason found out, might mean counting money or doing office work, but more often meant surfing the web, watching TV, and when Donna was working, she often pulled her book keepers in with her to chat or relax under the guise of helping with some paperwork.

It was a slow night, and Jason had spent more than a little time leaning over the counter and flirting with the cashiers, knowing for a fact that Donna was watching from behind the large mirror behind him. One of the night’s employees was April, a twenty-two year old girl with red hair, and Jason couldn’t resist hitting on her a little. She was super thin, like Shyla, though not in the almost unhealthy way that Shyla was, and April was a little taller as well. Her boobs were somewhat big for her small frame, maybe a large B cup, but they stood out on her diminutive figure. The other girl was a rather petite blond with a pretty smile, probably Bayan escort Ankara only just eighteen like Jason. Both girls were incredibly pale, their light skin even more attention grabbing with the dark maroon of their matching uniforms. Jason was telling the girls about his upcoming party and asking if they had any interest in coming.

It was against the rules for one level of staff to fraternize with another, so they would have to keep it a secret, he explained. Before they could agree or disagree Donna opened the door from the office and asked Jason to step inside. Jason was slightly worried that she had heard him invite the employees back to his place, but he shouldn’t have been. He should know better than most that it is hard to hear anything that didn’t sound muffled through the office walls. When he came in, Donna was facing away from him and looking out the window at the girls.

“I think we will start with a back massage tonight, Jason.” Donna instructed, not even turning to look at him. Jason wasn’t sure when it was that their dynamic had shifted so completely, but Donna seemed to be turned on by the illusion of having complete control over her young lover, so Jason didn’t mind. Donna was in her mid to late thirties, with short cropped hair that was currently died brown to match her seasonal attire.

Jason came up behind her and helped her out of her suit jacket so he could have better access to her shoulders. She wore a white, sleeveless top underneath which was designed to show no cleavage when fully buttoned, but somehow a few buttons had come undone before Donna had called Jason in. As he worked her shoulders, Jason had a clear view down the quasi-open top to Donna’s full tits. For a curvy woman in her thirties Donna, wasn’t specifically busty, but her boobs were certainly big enough to draw the eye, especially from Jason’s elevated angle. They were held up by a bra that looked far more expensive and sexual than he would have thought Donna owned. Jason guessed that it was new, and was turned on knowing that he was likely the reason that she had purchased it.

“I have been looking forward to closing with you tonight.” Donna purred. “The morning people were all the kinds of managers who compete over who can get the most done, and I am afraid they have not left too much for us to do tonight. I am sure you and I can think of something to do in the meantime.” Jason remained silent while he worked on a particular knot she always had trouble with. “While you work my shoulders, honey, why don’t you let that cock of yours out of those slacks? For the life of me I don’t see how you fit that thing in there in the first place; it simply can’t be comfortable.” More than willing to comply, Jason unzipped his fly and pulled out his large cock. Resuming his massage of her shoulders, Jason shifted his hips so that his cock slid over Donna Rhea’s shoulder and brushed against her cheek.

“Oh my, someone really is excited to be set free.” Without turning to look at it, Donna lightly caressed Jason’s cock with her fingernails like a favorite pet as it slid back and forth across her cheek. When Jason’s fingers found a sweet spot in her muscles she squeezed his cock somewhat roughly, but when he moved on she turned and gave it a wet but shallow kiss in thanks. “It is such a turn on being so naughty in front of a window like this, don’t you agree?”

“Absolutely.” And Jason was turned on, watching the two pretty cashiers ring up the only customer in line, they kept glancing up at the two way mirror, no doubt talking about the party Jason had invited them to. Jason gripped his cock and turned Donna’s head so that he could press the tip against her lips. She raised her eyebrows at him, as if to discourage such aggressive behavior, but she still opened her lips for him.

The girls couldn’t see in, but as Jason’s engorged cock slipped between his married boss’s lips, it was easy to be turned on whenever their eyes glanced up at the window. With one hand on the back of Donna’s head, Jason tried to slip the other down the front of her top to get a quick feel of her very tempting tits. Donna slapped his hand, stopping him.

Pushing his cock back out of her mouth she chided him. “No, no.” She said. “Today we are going slow.” She turned to face Jason and leaned back in her chair. “I want you to kiss me here,” she said, pointing to her lips, “then here,” pointing to her neck, “and then kiss your was further down here. ” sliding a long nail down between her tits. “You can only use your lips, I will handle the buttons. Once I am satisfied and ready you can start from my knees and work your way back up. Slowly of course. Understood?”

“Yes Mrs. Rhea.” Jason said as he leaned in to kiss her. He couldn’t resist hesitating, teasing her with his lips. He knew how much she wanted him, and liked teasing her with the threat of retaking control. It always seemed to make her more aggressive by the time she mounted him. He kissed her lips lightly, barely sliding his tongue across her open lips before shifting over to gently kiss her neck. Her nails dug into his forearms in frustration, and an involuntary moan escaped his lips from the pain. Taking his time, he had only made his way to the tops of her tits when someone called on the radio for a manager’s assistance.

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