Stupid Boy - Cover

Stupid Boy

Copyright© 2014 by G Younger

Chapter 14: Math Troubles

Coming of Age Sex Story: Chapter 14: Math Troubles - Teenage boy growing up in the Midwest learns about relationships, sex and sports. Join this 'stupid boy' as the girls in his life guide him through the highs and lows as he tries to navigate freshman year of high school. Winner of the 2014 Clitorides Awards as the Best Erotic Story by a New Author / 2nd place Epic Erotic Story of the Year / Best Author / Best New Author

Caution: This Coming of Age Sex Story contains strong sexual content, including mt/ft   mt/Fa   Teenagers   School   Sports   Rags To Riches   First   Masturbation   Oral Sex   Safe Sex   Squirting   Slow  

Sunday November 3, 2013 – Freshman Year

After Kara left for her trip, I got a text from Tami to see if I was around. I jumped onto the video chat and saw Jennie Wesleyan's smiling face.

"Hey good looking."

"Jennie! This is a surprise. Where is Tami?"

"I sort of hijacked her phone and PC. I wanted to talk to you."

"Well, I see someone is a little devious. You do know Tami will have your hide."

Jennie shrugged it off. She was used to getting her way.

"Don't worry. I'll take care of it." She was acting nervous.

"Jennie what's up? I can tell you have something to ask."

She gave me a quick smile.

"I'm just worried that I might not be very popular in your eyes."

"Jennie, I like you fine. Heck, my Mom likes you. What happened was a misunderstanding. I think we both learned a lesson. Unless you plan on stranding me somewhere, I might be open to whatever it is you are asking."

"I promise not to leave you again." She took a deep breath and let it out slowly. "I need a date." She waited a moment to see my reaction. When it wasn't negative, she hurried on. "My cousin is having an engagement party, and my Mom is trying to fix me up with Alistair Wilson."

"You're shitting me, right? His name is really Alistair."

"It is better than that. He insists that we call him Alistair, not Al, but Alistair. He is a pompous windbag, exactly what you would think of when you picture an aristocrat. He is a spoiled trust fund baby and makes my skin crawl when he tries to paw me."

"Why not go stag?"

"No, Alistair will be there. My Mother has matched us, and, if she can get Alistair and me together, she will be pushing for an engagement. Mother doesn't care if there is no love. She is more concerned about the match and what it looks like, as well as what Alistair's family brings to the table, than about whether we are even compatible. It is all very Victorian, and my sister and I have worked very hard to thwart my Mother's matchmaking plans."

"So why me? I don't fit into what your Mother would consider an acceptable alternative. If she is as determined as you say she is, I won't be able to slow her down."

Jennie bit her lip and wrinkled her nose.

"Please don't think less of me for what I'm about to say. I really do think of you as a friend, and I don't mean this as a slight. I just need to be honest with you. You're right. We both know you don't fit into what is an acceptable match for me. You come from a small town and don't have any money. God that sounds terrible, but the reality is that with money comes privilege and responsibility that is hard to understand if you don't have it. I've grown up in this environment, and I don't plan on leaving it.

"What makes you acceptable are a couple of things. The most important is that you are not after my money. You wouldn't believe the number of guys that have chased my sister and me just for our bank balance. The next is that you are a star athlete. With your talent, good looks, and charm, you have a tremendous earning potential," she said.

"Both of those together make you barely acceptable, but what puts you over the top is my Uncle Teddy's opinion of you. He has been your biggest advocate since we went out. He told our family about you charming Ashley Judd. She has been working on him for months to help with one of her charity projects. He said she rolled over with your help. He talked to the coaching staff about you and why they made you an offer. They liked your raw talent, but it was your leadership that sold them. Did you know that because of that weekend they have their best recruiting class possibly ever? It is ranked in the top 15 in the nation right now. Uncle Teddy is impressed, and that does not happen often. My Mother cannot ignore that kind of endorsement."

"Jennie, I thought a lot about you and your lifestyle after we went to the country club. I don't fit in. The other problem I have is that I may have met someone this weekend."

I could see the spirit go out of her. I saw a friend in need that I was letting down.

"Look, as long as we both know that we are just friends, I'll help you anyway I can. When is this party?" I asked.

"Next Sunday. I know you have a game down south Saturday. Would you mind if we sent a driver down and brought you up Saturday night, and you could stay with us? The party will go late, so you will miss your morning classes on Monday. Is that okay?"

"That should be okay. I need to ask my Mom, but she should be okay with it. What do I need to wear?"

"Okay, now don't get mad. This is where you have to accept that being my friend means that there are some benefits. Tami suggested that I get in touch with your friend Cindy to help with a shopping trip."

I just shook my head and then said, "I am pretty sure Cindy would love to do that. I'm her personal Ken doll to dress up. Am I to assume you are buying?"

"Yep, and I hope you will accept gracefully."

I thought about it for a moment and figured what the hell.

"Okay."

She was bouncing up and down, "Oh goody. Cindy knows what I want so don't fight her. I promise that you'll look good. Can you go tomorrow night?"

"That will work. I need to get a haircut also."

"Already taken care of. Just let Cindy pamper you and don't be afraid to get a few extras. Cindy has final say, but this is my way of saying thank you."

"Jennie, please don't think that you have to buy me things."

She got serious.

"I really don't, David, but this is something I can and want to do for you. Plus if you are going to be my date, you have to look the part, and it is not fair to ask you to buy the clothes you need."

Tami's door opened and she saw me.

"Okay, Dawson, what are you up to?"

I acted as if I was caught in the act. I gave a big sigh, like I was confessing.

"I was planning your Thanksgiving trip and asking Jennie for some suggestions when I go to Buddies." Buddies, is a local porn shop that sells adult toys. "Did you know there is such a thing as edible panties?"

Tami and Jennie both went bright red. Tami looked at both of us.

"He won't tell me what is going on, but you will."

She tackled Jennie on the bed and started tickling her. Jennie was shrieking and trying to fight her off.

"I give!" Tami let her up and they were both panting. I found I had suddenly gotten hard watching the two of them roll around on the bed. "I asked him out on a date."

Tami looked pissed.

"You did that without asking me first?"

Wait a minute. This was my life she was talking about.

"Hey..." She gave me a look that left the rest on the tip of my tongue.

"You gave me control of your dating. Let me hear her out before this goes any further."

Jennie explained what was happening. Tami asked several very good questions that I had neglected to ask. I found out that Jennie was not opposed to 'fucking my brains out' as she eloquently put it. She also hinted that her sister might join us. I really liked the sound of that. Tami could see that she had me over a barrel.

"Jennie, give me a few minutes with David."

Jennie winked at me, and I realized that Tami had set this up. She didn't hold as many cards as she thought she did.

She started her opening gambit.

"David, I don't think this is a good idea for you to go out with Jennie again."

I played along.

"Come on, Tami, what is wrong with me seeing Jennie?"

"Were you not the one that was not looking to date until after football? I think that is still a valid reason for you not to date."

I looked dejected.

"Okay, you know best."

She was caught completely off guard. I could see the wheels turning.

"I will go get her so you can tell her. Just let her down gently."

Tami knew I was the biggest pussy when it came to hurting girls' feelings. She opened the door and asked Jennie back in.

Jennie looked at me and saw my dejected face and Tami was unreadable. I decided to put her out of her misery.

"Tami and I have talked, and she has some good points about me waiting to date until after football is over. So we decided that it would be okay if I took you as a friend. I will even make it look good so that your Mother and Alistair think it is a real date."

Tami rolled her eyes when Jennie gave her a big hug. She beat a hasty retreat before Tami could change her mind.

"Okay you little shit. Now you have to help me out," Tami said after Jennie left.

"Let me guess, Thanksgiving."

"You got it on the first try. That and I need more guys for the Christmas Dance. Can you get Luke's brother Mike and Tim Foresee to come also?"

"Of course, I'll talk to them at lunch and send you a text to confirm. Can I also ask Jeff?"

Her face lit up.

"That is a great idea. I have the perfect girl for him."

I changed the subject.

"How are you doing?"

"You know I miss you like crazy," She sighed. "It's just not the same without being there to see you every day. It broke my heart when I wasn't there for you when Tracy lost her shit. If it wasn't for our video chats, I think I would go nuts."

"In a strange way you going off to Wesleyan has been good for me."

"How's that?" She asked cocking an eyebrow.

"I've been learning to look out for my best interest. When things got hard, I was so used to going to you to decide what I should do, I never learned to stand up for myself. One of Tracy's friends set me straight the day she 'lost her shit.' Hell, I'm still terrible at it. Tracy acts like nothing happened. She even got me to take her to the Halloween Dance. Suzanne had me in the sack less than 24 hours after she cheated on me. The one that surprised me was Cindy. I have been able to hold firm with her."

"What makes her different?"

"I think it is because she was sleeping with Greg while Angie was pregnant. I understand they were just doing the friends with benefits thing, but Kyle would be a game changer for me. If I were dating someone who got pregnant, I would not be hooking up with someone else just to relieve some stress. I would be exploring what the next step is."

Tami bit her lip.

"Do you think Greg and Angie are going to get married?"

I thought about this for a moment before responding.

"When Angie first had Kyle, I could see Greg was deeply in love with both of them. Earlier today Kara came over. Granted, Kara is beyond gorgeous. He couldn't resist hitting on her."

She smirked at me.

"We will talk about Kara before we sign off, but tell me more about Greg and Angie."

"I'm wondering if Greg being a serial dater is going to ruin it for a meaningful relationship with Angie. One of my brother's rules is- if you are dating someone, you do not date someone else. I mean, he has pounded that into me. From what I understand, he lasted a little over a month when Angie was shipped off to her aunt and uncle's before he hooked up with Cindy. Now Angie is actually back for exactly a week, and he is hitting on another girl." I felt my shoulders sag. "I lost a lot of respect for Greg today. I've never known him to cheat. Not even a whisper, and we both know if he ever did word would have gotten out."

"Let me ask you something, David? Are you worried about yourself becoming like Greg?"

That set me back on my heels. I got up and paced around the room. My mind was racing. Was it possible that I couldn't be with just one girl? If I wanted a quick roll in the hay, I could call any number of women. Was I any better than Greg? When I was dating Tracy, I spent time with Alice Phillips and my chaperone. Even though Tracy gave me a free pass for the weekend, it was up to me to decide if I used it. Then there is Cindy and Suzanne. I know for a fact, that if either asked I would sleep with them regardless if I were with Tracy.

Finally, there was Tami. If she ever asked, I would drop everything to be with her. The question was would I still sleep around on her?

"Tami, do you consider me a bad guy?"

Tami knew me well enough to help talk me through this.

"Define bad guy."

"I hold Greg to a higher standard than I do myself. I've had sex with Suzanne while I was with Tracy, but I have a problem with Greg having sex with Cindy while his pregnant girlfriend was exiled. If I think Greg is a bad guy for what he did, doesn't it hold that I'm a bad guy also?"

"You need to answer a critical question before you pass judgment. Were you in a committed relationship with Tracy when you had sex with Suzanne?"

"Yes."

"David, search your heart. Were you and Tracy in a committed relationship?"

We were right back to the Tracy's 'not together' mantra. I remember thinking that she could go out with someone else, and it would not be a problem with me, but was I being honest with myself. Did I feel committed to Tracy? The answer was yes, I was committed to Tracy.

"Yes. I felt a commitment to Tracy." "Good, so far you are not a bad guy. Now let me ask you the second part of the question. What were the expectations for the relationship?"

"You lost me with that one."

"Did you agree to a monogamous, open, or some kind of blended relationship?"

It was as if a light came on. I had no idea what kind of relationship Greg and Angie have. Angie and Greg may have given each other permission to sleep with others. If that were the case, then Greg being with Cindy would be okay. I might not agree with their decision, but it was theirs to make.

The problem was Tracy pretty much told me that we had an open relationship. What else does 'not together' mean?

"We never talked about it in those terms. I guess the 'not together' comments she made would lead me to believe that we had an open relationship. It was the whole 'not together' thing that was driving me nuts."

"Here is what I think. You are too young to be in a committed relationship. Greg and Angie are too, but they have something that overrides being young and not ready, Kyle. Almost never does a high school relationship last the test of time. That doesn't mean that you shouldn't be in them. I strongly encourage you to date, but don't think that just because you love someone now that it will last. People change. It's called 'growing up'.

The other thing you have to get through your thick head was you are not currently built for a monogamous, one girl type of relationship. I also know that you could not tolerate a girl that was with other guys and with you," Tami informed me.

I thought about that for a moment. Was the real reason I was able to forgive Suzanne and not Cindy because I suspected that Cindy slept with her ex? Deep down it wasn't so much the trust but that I couldn't stand the idea of sharing her.

"How can I be so self-centered to have one standard for me and another standard for the women I date?"

"David, it is not self-centered, it is being honest. As a 15 year old male, to ask you to be in a committed monogamous relationship is ludicrous."

"Could you use any more $10 words? Wesleyan is starting to make you too smart. The average person is not going to be able to understand you in another year," I snorted.

"Listen 'stupid boy', if you don't understand a word go look it up."

"I need to talk to Greg and Angie before I pass judgment."

"That is a good start. You also need to decide what is right for you. I expect you will find that as you grow older and you gain experience you will have different views on thing. Now let's talk about Kara."

I groaned. Tami loved to get the dirt on all my girls. I also knew it was easier just to tell her.

"What do you want to know?"

"Is she as beautiful as everyone says?"

"Holy crap yes! Tracy is close, but there is something about her that turns me on."

"Here is the deal. You can't date her."

"What?"

"I repeat. Here is the deal. Be friends with her, fuck her brains out, but under no circumstances are you to date her."

"Okay you lost me."

"Do you trust me?"

"Yes."

"Have I ever done anything that was not in your best interest?"

"Yes."

"Oh shut up, giving you a wedgie in third grade was just fun. Get over it."

"Okay, then no."

"Do I know you better than you know yourself?"

"Yes."

"Then why are you fighting me?"

"Just explain it to me."

"You my friend are not ready for Kara, just like you were not ready for Tracy. I know you are not ready for me. Kara is a potential long-term relationship. You need to be her friend; not her one and only."

"Why are you worried about her and not Jennie?"

"Because Jennie is just rebelling. She is not a potential girlfriend."

"So you are saying I can't have a girlfriend?"

"No, I actually want you to have a girlfriend. My objection is you getting into a serious relationship."

"Is that why you are having me date the Wesleyan girls?"

"Yes and no. Yes because the distance factor and no because of selfish reasons. Because of your antics and the glowing report Jennie gave them, they will not leave me alone. It is either set them up on dates or they will lynch me."

"Hmmm, I like a good lynching. So why are they so interested in me?"

"Are we really going there? Okay, I'll play along and stroke your ego. You have a fantastic body with a rather large wiener, which gets bigger with each retelling of naked dance party. They have all decided that you are some kind of sports' god. In addition, a girl that will remain nameless, Jennie, has reported that you could talk anyone out of their panties, and you are a great guy. Oh and I almost forgot, you are a good kisser. What boarding school girl would not be interested in that? You forget our only contact with guys is prep school boys. They want a real man; even a young one and they have decided that you are it."

"So would I be safe to come visit you some weekend."

"Probably not."

"Sounds like what I need."

"If you come for a weekend, it is not so you can bang every girl in my dorm. You are coming to see me."

"Sure, that's what I meant." Why does everyone roll their eyes at me? "Before I get off here, I need you to help me with one more thing."

"What's that?"

"After the football season, I need a job."

"I'll start working on that. I assume you are looking for something that does not eat up all your free time and pays well."

"I am not going to be a male stripper."

"Damn it, my best idea already rejected. I can get you to do it for free anyways."

"Probably, I have no shame. Speaking of which, did you hear about my Halloween costume."

"I ordered the poster."

From the look on her face she wasn't lying.

"I am going to regret asking this, but what are you talking about?"

"It is on your website. Nice idea to give all the profits for a scholarship for a teen Mom. I would bet that means that Angie is getting some funds to continue her education."

"I really wish people would clue me into things."

"Would you have said no?" Tami asked.

"No, but they could ask."

"I'll tell them, but we both know you would just mess it up."

"Whatever. I better get off. I have a math test tomorrow, and I need to study."

"David, sometimes I don't tell you, but thank you for being my friend."

She dropped her end of the conversation before I could respond. I suspected that going to Wesleyan was harder than she let on. I just hoped that her involvement in my life and our chats helped. It would be tough being the lone scholarship kid at an exclusive school. She has a lot to prove, but I knew she was up to the task. Becoming a doctor had always been her dream, and I didn't know anyone smarter or more determined than her. I was lucky to call Tami Glades my friend.


Monday November 4, 2013 – Freshman Year

It was a glorious Monday morning. Since Coach Harrington had left, there was no morning practice. Instead I could just go running. It was a crisp fall day, and I could see my breath as I started. I had on sweats and a hooded sweatshirt. I was in my zone and working through life's problems when I noticed I had come up on a group of girls running. As I came closer to them, they speeded up to stay ahead of me. Their pace was now matching mine. I decided to run with them.

The weather was perfect and I was loose. I felt like I could run forever. I was not paying attention to where we were going, trusting they had a route worked out. They seemed to be winding through subdivisions and finally started heading back to the school. When we started to get close, I noticed they were laboring hard. We got near the school, and I could see there were three police cars with their lights flashing. My street was right before the school, so I turned and headed home.

I had my ear buds in and grooving to my favorite song when I saw a flash of someone at my side as they tackled me. Luckily, I landed in the grass, and I found two police officers on top of me. I was quickly cuffed. By the time I was apprehended, the other two squad cars and the cross country team with their coach were all on the scene. When they pulled back my hood, Peggy Pratt was screaming at the police to let me go. I finally shook my ear buds loose so I could hear.

Peggy was pissed.

"You idiots!. You said some guy was chasing you. Do you not recognize who this is? This is David Dawson!"

"Did he try to do anything to you other than follow you?" The officer that tackled me asked.

None of the cross country team would look me in the eye. The coach got in their faces.

"Answer the man!"

They all shook their heads no. The policeman took the cuffs off of me.

"Son, what were you doing?"

"I was running, sir. I play football, and I didn't have practice this morning so I decided to run. When I saw the girls, I noticed that they were running at my pace. I let them lead. It is more enjoyable to run with someone than alone. When they got back to the school, I turned to head home. That was when you tackled me."

I noticed that Peggy was in street clothes.

"I used to run with him, but he is too fast for me," She added. "David is our starting quarterback and these air heads should have recognized him."

She chuckled.

"You realize how fast you were running? These girls will be sore for a week."

"How come you weren't running?"

"I have two tests today. I was coming in early when our coach grabbed me and told me that the girls were being chased."

"I have a first period math test. Do you need me for anything else?" I asked, looking at the policeman.

I jogged home and got into the shower. I was running late so I sent a text to Greg to see if he was still home. He sent me one back saying he was already at school. I ran down, grabbed my bike, and rode it to school. I was five minutes late. I ran into my algebra class to find everyone taking the test. I sat down in my seat, and Mrs. Sinclair motioned for me to come out into the hall with her.

"David you were late for class so I will be giving you a zero on the test. I don't care how big a star you think you are. You will not slide by in my class."

I was stunned. I currently had a B+ in this class and a zero could pull my grade down to a D or even F.

"Mrs. Sinclair, I'm not sure what I have done to make you mad at me, but this will kill my grade in this class."

"You jocks are all the same. You think you will get a pass in life just because you are popular. Well, today you are learning a valuable life lesson."

I thought of several comments I wanted to make. All of which would not help the situation. Some might actually get me kicked out of school. I decided this was too big for me to take on by myself. I needed advice.

"Mrs. Sinclair, would it be okay if I made a phone call on how to handle this?"

"If I let you leave class to make a call I will have to let everyone. Sit quietly until class is done."

I was feeling pretty sorry for myself. This was so unfair. Why was she singling me out? There had to be a way for me to makeup the test. I am sure I wasn't the first one to ever miss a test or be late. They surely did not get zeros.

When class ended I waited for everyone to leave. Mrs. Sinclair did not look happy that I was still there.

"Ma'am there has to be a process for students missing an exam. How can I make this test up?"

"As I said earlier, you were late for the test to start, so you get no credit for it."

I was stunned. Students were streaming in for the next period so I just left. I knew Coach Lambert had a free period now so I went to his office. His door was open so I knocked.

"What can I do for you?" Coach Lambert asked.

"I am having a problem with my math teacher. We had a test this morning, which I was late for, and she is not letting me make it up. If I get a zero on this test I am afraid it will really hurt my grade. Can you help me, or give me some advice?"

"Can you think of anything that would have made this teacher mad at you?"

"Well two things actually. The first is I have missed some class time, but all of that was excused. The second is a comment she made. She said she didn't care how big a star I was, she was going to make an example of me. I think she thinks that I am treated differently because I am an athlete."

"Well get used to it. People will always think you are getting special treatment. Let me give you some advice. Work this out with her. Your best approach is that she is treating you different because you are an athlete and you want to be treated like everyone else. If that doesn't work, come back and talk to me."

"Thanks Coach."

I looked at my phone and it told me that World History was almost over. So I figured I would just go back to Mrs. Sinclair's room and wait for the period to end. When the bell rang there was a rush of students exiting the class. I waited for the majority to leave before trying to enter the room. Mrs. Sinclair did not look happy to see me.

"Ma'am, could I have a moment of your time?"

"Since you have been polite I will give you a couple of minutes."

"I just have one question. What would have happened if I wasn't an athlete? Would I have been able to take a makeup test?"

Her body language told me she wasn't happy with the question. She gave me a stern look.

"This is going against my better judgment, but I will give you one chance to prove me wrong. When is your study hall?"

"Last period."

"I will give you a makeup test then. Don't bother asking what was on this morning's test because it will be different."

"Thank you, I will see you then."


At lunch, I pulled Luke, Mike, Tim and Jeff aside to talk to them about the Wesleyan Christmas Dance.

"Tami needs a favor. Wesleyan is having a Christmas Dance, and she wanted me to ask you guys if you would be willing to be dates for some of her friends."

They all smiled.

"Okay, what's the catch? Are all these gals unfortunate looking and have great personalities?" Jeff asked.

"No, they are all good looking, well except for yours, Jeff. She has a bit of a mustache. But according to the other girls, she is a good kisser."

"They kiss each other?" Luke groaned.

"Well, of course, what do you think boarding school girls do when they are lonely? I'm sure that if you go, there will be plenty of girl-on-girl action." I had them hooked. "The dance is on December 19 which is a Thursday. We will go up Thursday afternoon and stay till Sunday. So come prepared, Jeff. That means bring condoms, and we will have a fun weekend."

"I don't think I can go," Tim said dejectedly. "My family is flying to Florida for Christmas. I need to check the dates with my Mom."

I handed him my phone.

"Call and find out. I need to tell Tami today."

Tim went off to ask. Of course, the other three went and told everyone that would listen. Tim came back and told me that he couldn't go. As soon as everyone knew that there was an extra slot, Jim pulled me aside.

"David, buddy, friend of mine..."

"I don't know, Jim. What's in it for me?"

He thought for a moment.

"I won't tell my Mom what you are doing to my sister."

"Jim, I'll go with you, and we can tell your Mom together if you are worried. Just be prepared to live with your sister until she goes off to college. After a few weeks, she will be cranky. After a month, you will be losing body parts."

Jim went a little pale.

"Fuck! She would castrate me. Okay how about this ... I will be a loving and supportive brother until she leaves."

"Deal, you're in." I should have been a little further away. He grabbed me, put me in bear hug, and swung me around like a doll.

"You snooze! You lose suckers!" Jim yelled.

Not the most gracious winner, but he was happy. I sent Tami a text confirming the list.

I had some happy boys on my hands. I also had an unhappy girl, Gina. Now that I knew her better, I knew what the problem was. In her eyes, things were either black or white. Either I was with Kara or I wasn't. I got up and walked over to her end of the table.

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