Mr. Nice Guy vs. High School Ch. 01

(For those of you who would like to read the first three Mr. Nice Guy installments, the first story is Mr. Nice Guy vs the Mall Rat, followed by the Mr. Nice Guy vs Concert Milf and the Mr. Nice Guy vs the First Interview. Those stories may give a little back story, but it will not be needed for this series revolving around Jason's senior year of high school.)

*

For an 18-year-old with no previous girlfriends, Jason was getting a decent lay quite often. Between fucking the busty, young mallrat Kat senseless anytime he felt like calling her up, and fucking his boss Mrs. Donna Rhea anytime she could get him alone, Jason wanted to seduce someone new. Like, maybe one of the many gorgeous girls from his school. The problem was that he wasn't sure how to start.

High school is different than just picking someone up at the mall or at a concert. If you make a pass at someone openly, then everyone knows about it by the end of the day. If you are rejected by one girl, then the next will hear about it and feel like a consolation prize. If you get laid with one girl, then other girls may not want to sleep with you because of who you slept with. At least, that is how Jason saw it, and it was why he never stuck his neck out and asked someone from school out on a date. Well, one of the reasons.

Jason also had no idea how girls at his school rated him. He had heard rumors going around that he and Mary were hooking up - Mary being one of the most popular girls in the school. He also heard that he and Shyla, a hot little pothead with an easy reputation, had fucked several times, but neither rumor was true.

He was certain that if the girls knew, they would probably blame him for the rumor and kick his ass. Girls flirted with him sometimes, but he always felt deep down that he didn't fit in. The guys at school made that abundantly clear. He had been in far more fist fights growing up than he had been invited to parties. If he actually hit on someone who was flirting with him, and it turned out to be some weird gag, then he would be a laughing stock.

Basically, he needed advice on where he stood with the fairer sex of Rock Bridge High. His mind wandered to Gretchen Greene. Gretchen was named after her grandmother by her mom, who could obviously care less that her daughter was doomed to be made fun of her entire life. Jason and Gretchen had been friends until the age of seven, when her mom decided that Jason and every other kid was a bad influence and started homeschooling the girl. By the time she was old enough to attend high school, Gretchen finally started coming back to Rock Bridge.

Over the years, she had apparently stayed friends with Laura and Nicole Frost, two churchy sisters who were a year apart. Laura, Nicole, and therefore Gretchen by association had a reputation for being extremely religious. Jason had spoken to Gretchen a couple of times at Rock Bridge High. It was nothing deep, but enough to pass for polite banter between two old friends. She seemed the perfect girl to let him know where he stood in the high school hierarchy, since she was most likely to be unbiased herself.

As it happened, Gretchen lived just up the street from Jason's grandmother. That Monday after school, Jason drove over to his grandmother's to do some recon.

"Oh Gretchen? Yes, she still lives in the house at the end of the road with that mother of hers. You two always were cute together. You should go up and pay her a visit. That mother of hers never gets home til after six, working god knows where."

Jason was surprised his grandmother spoke so disparagingly about Mrs Greene. He had never heard his grandmother say an ill word about anyone. Shrugging it off, he accepted her suggestion and strolled up the street on foot to the Greene residence.

He knocked, but he did not get an answer. Gretchen did not own a car, and with no car in the lot Jason almost gave up until he realized he heard a shower running. Amused, he started belligerently ringing the door bell. Soon he could hear Gretchen running up to the door. "Okay okay okay okay I'm coming." Her head popped up in the window beside the door. Her hair was wet. "Jason Lakes? What are you doing at my house?"

"I need some advice. I was hoping you could help. Can I come in?" Jason smirked, knowing she couldn't be wearing more than a towel.

"Give me a minute?" Jason nodded, and Gretchen disappeared into her home. She really was gone only a minute before the door opened to reveal Gretchen in a loose sweater and sweats. Gretchen always wore loose, unflattering clothes, as well as outdated clothes, like shawls. Her favorite accessory looked like she stuck her head through an oversized doily. Jason could easily see how she was unpopular and saw ways to fix it. Maybe she could do the same with him?

Jason stepped inside. Gretchen was also short, coming up just a little above Jason's waist. Gretchen waited for Jason to ask his question, and stalling for time Jason looked around the house. He had been a child when he had last been here, and he experienced a little bit of vertigo realizing how small everything looked now that he was 6' 5''. Not only that, but Gretchen was kind of short, and her mom, according to the pictures, was shorter still, so everything was sized for a small person, and none of the furniture came above Jason's waist.

Feeling dizzy, Jason wondered down the hall to Gretchen's room, where they would sit and hang out as kids when her mom was not home. He took a seat on the bed, still feeling dizzy. Looking up at her, she looked freaked out at his assumption that entering her bedroom and sitting on her bed would be okay.

*** "I uh... got really dizzy..." Jason said as he explained how weird it was being so big in a home sized so little. Gretchen burst out laughing and took a seat beside him, explaining it was his fault for being freakishly tall. Their friendship picked up as smoothly as if they had never put it down. She talked about home school and how awesome it was to be back in regular classes again with other people. She complained about how controlling her mother had been for the seven years that she had been homeschooled, and how much she was looking enjoyed trying to catch up on the normal experiences that she had missed while being stuck at home. Her only social interactions for seven years had been her two friends Laura and Nicole. She had only been allowed to maintain her friendship with them because their family went to the same church as she and her mom. While he tried to look interested Jason couldn't stay completely focused. While she talked, Jason's eyes slowly explored the bedroom, and eventually locked onto a bra that seemed out of place hanging from the back of the computer chair because of its size. Jason pointed it out, interrupting Gretchen's life story with a laugh. "Maybe you are not as small as I thought you were."***

Gretchen turned beet red and jumped up to hide the bra. Jason took a closer look at her sweater. Did she wear baggy clothes to hide a rack?

"So what did you come here for?" Gretchen asked defensively, crossing her arms over her chest. Jason sighed and explained his insecurities. He told Gretchen about the women he had slept with this past summer, about his confusion over the rumors going around about him sleeping with girls he hadn't slept with, and his general discomfort with "the cool kids" at school. This time it was Gretchen's turn to laugh. For having been isolated from other people up until four years ago, Gretchen had a good deal of knowledge on the rumors surrounding Jason.

***"You are one of the most popular guys in school."

"How can I be popular? I never hang out with anyone."

"People just assume that is because you choose not to. People assume you have an active social life, and that no one else is cool enough to be a part of it. Maybe rumors follow you around because everyone wants to know what your life is really like. Your stepsister always answers any questions people ask with vague answers that never really reveal any details. She wouldn't be anywhere near as popular as she is if she wasn't good at implying to know your secrets but never quite revealing anything. Trust me I know, she was the person I went to when I started coming to Rock Bridge High. You were one of my only friends in elementary school and I wanted to see how you were doing. Do remember how you used to beat up the bullies to defend the smaller kids back then?"

"That was not really what I was doing. I enjoyed fighting, and the tougher kids were always more fun to throw down with."***

"Well whatever." Gretchen shrugged. "The tough kids picked on the nerds to try and impress the girls. How do you think the girls felt about the guy who could beat up the tough kids?"

"Mad that he beat up their men, if I remember right."

Gretchen looked at Jason as though he were an idiot. "Maybe some did, but others saw you as both a tough guy and as a good guy, for beating up the bullies. From what I hear, that hasn't changed. Is it true you beat up six kids in middle school at the same time?"

Jason shrugged. "Technically, but I am surprised you heard about it. I was in a mostly black school, and some girl told everyone I was racist, so six kids came up talking trash. I don't think they were really going to jump me, I think they were trying to intimidate me, but one kid pulled out a knife and I kind of spazzed out and went ape shit on them. I didn't exactly make friends there either. How the hell did you hear about that?"

"I heard about it because it is part of your...your fame. You beat up six guys, Jason. You're smart, which is obvious to anyone who has a class with you. You're funny, you're hot, you're fit, you're tough as balls, and a good guy. When Cheerleader Bambi's heel broke last year by the coke machine and she fell backwards, I heard you spun from the machine and caught her head before she hit the ground! It is no wonder I.... er, every girl at school has kind of a crush on you." Jason did not see himself as a good guy, just big and fast, but he saw no need to correct her.

"You have a crush on me?" Jason asked.

"No, I said girls have crushes on you..."

"That isn't what you were going to say."

"But it's what I said! Leave it alone!" Gretchen turned red again. From embarrassment or anger Jason couldn't tell, but he figured it was a combination of both.

"If you have such a crush on me, why are we not making out?"

"Asshole!" Gretchen squealed, grabbing a pair of jeans off of the floor and throwing them at him. Jason caught them out of the air and tossed them into her laundry basket. "You do not want to make out with me!" she said incredulously.

Jason met Gretchen's eyes and answered honestly. "I am more than willing to make out with you, Gretchen Greene."

"Why?"

"Because I am lying here alone with you in your bedroom, and I am more than a little turned on by you having a crush on me. Because this isn't the first time I have thought about kissing you," Technically true, though he had imagined making out with nearly anygirl he spent any time with. "Because we have been friends for years, so we are comfortable together. Because since we haven't spoken in forever there isn't some huge friendship to risk. Because I would like a chance at those bad girls hiding under that sweater. Because --"

"You can't just make out with people because you want too."

"Why not?" Jason returned.

***Gretchen had no answer. She didn't really look like she was trying to think of one either. Finally she spoke. "Okay, here is the deal. I want to, I really kind of do, but it is not that easy." Gretchen came and sat down on the bed. It took her a moment to gather her thoughts. "I used to hang out with this girl at school who had an older brother. He would squeeze my ass and stomach and tell me I was his girlfriend. I wasn't, but when I didn't argue it he started being...more free with his hands and stuff. He was really gross. I told my mom, and she freaked out and pulled me out of public schools. So without being aloud to see any guys I eventually started kind of seeing a girl. Do not ask me who and I am not a lesbian! At least I don't think. She really gets me and lately I have been wanting to try things with a guy again. So... understand?"

Jason's mind was doing laps. That is why Gretchen dropped out of school? That at least made sense. Who was the other girl? It had to be Laura or Nicole Frost, one of the girls known as the churchy sisters. One was a lesbian? Since neither sister had been home schooled Jason had kind of known both of them all of his life. Which one was a lesbo? He tried to picture Gretchen in bed with one and then the other, and decided it had to be Laura. Laura was meek like Gretchen. Nicole was tall, blonde, and beautiful enough so that guys who had to know they couldn't round too many bases with her would still fumble over her trying to stay in her good graces. "Yeah, I understand. You want to make out with me, so long as I understand that I am mankind's last hope for keeping you on the straight and not so narrow." Jason smiled and winked at her. "Now get your ass over here and kiss me!"***

"No pressure." Gretchen laughed out loud but eventually slid over as Jason kept patting a spot beside him. She leaned into him. Jason kissed her lips gently at first, but with each kiss slowly introduced his tongue as his hands lifted up to her hips and then around her back to pull her into him. Once she was comfortably melted against him with her arms around his neck, Jason lifted her and laid her down on the bed, and then crawled up to lay beside her, again taking her lips with his.

Jason's hand innocently drifted across her body and rested on her shoulder, positioned so that when he rubbed her arm, his arm happened to rub across her chest. She was not wearing a bra, and what she had was definitely more than Jason would have expected Gretchen writhed against his lips and against his casual touch, so it was not too much of a shock when his hand slipped from her shoulder and got a descent squeeze of her tits. She cooed when he pinched her nipple, hinting that she might like that kind of sharp pain, so Jason cupped one boob in his hand and bent down to bite it through the sweater, bringing about a gasp.

All the while, Jason had been thinking ahead. He propped himself up on one arm and addressed Gretchen directly. "Okay," he said, "if I am mankind's last hope, then there are going to be rules." Even as he spoke, one of his hands had drifted down to the bottom of her sweater and slipped underneath, rubbing her stomach. She started to ask what he meant by that, but his fingers found a bare nipple and pinched down hard, causing her mouth to open in a very enticing way, which Jason just had to meet with a kiss. The way her hands pulled his head down onto hers meant she clearly liked the pinching, so Jason's hand switched back and forth between the nipples, pinching, pulling, and flicking each in turn.

By the time Jason came up for air, Gretchen was out of breath and breathing heavily to compensate. Jason started in on his rules.

"Rule one is, don't be embarrassed or ashamed by any question or anything you want to try. Since I may be the last guy you ever do anything with, I want you to do anything with me that you want, and I am more than willing to do it all with you and to you, believe me. Second, I don't like thinking that this is my only shot to show you that guys are not all gross, so anytime in the future you want to do anything with me, or to me, or have me do to you, just say the word and I will be right there."

Gretchen laughed. "How selfless of you!" But she smiled in a way that said she would take him up on it.

"It is also a good rule so that you do not feel rushed to try something new, because there is always something I can do to you next time." Jason didn't want to have to rush to take her virginity. There was no way she would let a guy near her if he rushed to take her before her mom came home, and Jason would never pass up an excuse to come back for more.

He expected to slip back into the make out session they had been in, especially since he had removed the pressure to rush, but Gretchen surprised him by saying, "I want to see your cock."

Jason smiled. She looked at him as if worried he would not agree! Had she heard him offer to give her full access, anytime and anywhere? "Okay," Jason said easily, and took her lips again with his. Dragging his free hand away from her surprisingly full tits, Jason undid his zipper and fished his cock out while they kissed. Reaching up and grabbing her hand in his, he pulled it down to his shaft. She was hesitant at first, but once the cock was firmly in her tiny hand, her other hand joined it and she started exploring its length and girth. She broke the kiss and smiled.

"I said see your cock. See it." Jason smiled and laid back as Gretchen propped herself up on her arm to get a look at it. "It is a really big, pretty cock. Are you sure Mary and Shyla have not seen this?" She never looked at his face, her eyes on his cock as her hands pulled and tugged it this way and that. Jason said again that they had not. "Lucky guess then, both rumors said you had a big cock." Gretchen said absently. After a moment she asked "Can I suck it?"

***Jason wanted to laugh. What a question! "You can do anything you want with it." With no other hesitation Gretchen's pretty little head lowered itself onto his cock. Losing sight of Gretchen's face through her wet hair, Jason closed his eyes and enjoyed the feel of his cock sliding between her lips into her wet and oh-so-warm mouth. She was being hesitant, taking it in her mouth for a second and then just looking at it for a bit, then doing the cycle again. Jason lost track of time, lost in the feeling of his dick sliding in and out of Gretchen's mouth. Jason told her things to try, and answered any questions she had. Jason told her that she was a natural with her tongue, and told her he was looking forward to tutoring her anytime she wanted to experiment.

She sat up with a big smile on her face. "Thanks! This is so hot, I love that there is no pressure at all, and I am really turned on..." Before Jason could coax her back to the task at hand, they could hear the front door open and Gretchen's mom call for help with the groceries. Jason swiftly shoved his cock back into his pants and buckled up. "I'm coming!" Gretchen yelled back. "She cannot find you here!" she said in a rushed whisper. "Wait till we are at the car and sneak out the back!"***

Jason agreed, and in no time he was running across several back yards until he got back to his grandmother's house. Not wanting to talk to his grandmother with a girl's saliva all over his hard cock, Jason hopped in his jeep and headed home.

*****

The next day at school Jason tried several times to get Gretchen alone, but she would not make eye contact with him. When he would approach her she would look away and rush off into the crowded halls. Was she embarrassed, or was she cutting things off? Worried that his escape had been noticed by Gretchen's mom, he was determined to find out what was wrong. Before the last period of the day, he finally took a chance and offered her a ride home in front of several people in the hall. She sighed and said "sure," before slipping past him and out of sight. Jason had a strong feeling that she was going to call things off.

Waiting by his jeep, Jason imagined all of the different ways the conversation would go. Sometimes he pictured scoring one last blow job on the drive to her house, sometimes he pictured her refusing to get in his car, and simply telling him it was a mistake and then leaving. He regretted not getting to suck her bare tits, considering he likely would not get another chance. Finally, just as he was about to give up and go, and when most of the lot was empty, Gretchen came out of the building. Eyes downcast, she walked purposefully to his jeep, but she was not alone. Nicole held her hand, and was all but dragging Gretchen forward.