Stupid Boy - Cover

Stupid Boy

Copyright© 2014 by G Younger

Chapter 17: Coin Flip

Coming of Age Sex Story: Chapter 17: Coin Flip - 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  

Monday November 11, 2013 – Freshman Year

Mom woke us up so Angie could feed Kyle. I looked at the clock. It was 3:00 am. I grabbed my pillow and went to my living room to sleep on the couch. My alarm went off at 7:00 a.m., which woke Kyle up. I entertained him while Angie took a shower. She stole a pair of shorts and one of my button-up dress shirts. She looked damn fine with her wet hair. She smirked when she saw my morning wood. I just handed her Kyle and took my shower. When I got out, she was gone.

I went down to the house for breakfast, deciding I was too tired to run. After ten minutes of silence, I decided that having breakfast with Greg and Angie was a mistake. Greg motioned for me to leave with him, and he gave me a ride to school.

"What are you going to say to Cindy?" he asked me, his nervousness quite apparent.

"Nothing," I responded as I looked out the window.

"Aren't you interested in hearing her side?"

"No."

"David, you have to say something to her."

"Greg, as far as I am concerned, what we all did was a onetime thing." I turned from the window to look at him. "I said I was not ready for more. I made it clear how I felt about it. I am a little confused why everyone thought another threesome was a good idea. I'm just glad it wasn't me putting my dick into Angie."

Greg's face went red. I succeeded in pissing him off. He pulled the car over, and I continued before he could tear into me.

"It would suck if the shoe was on the other foot," I said softly. That took the steam out him. "Look, I'm scared to death you're going to force Angie to do something stupid. I would hate to see her move back with her aunt and uncle. That is why I'm not going to confront Cindy. We don't need a side show. You need to focus on putting things right with Angie. In the big picture, Cindy and I don't matter." I sighed and looked him in the eyes. "Greg, think for one minute. If I were to bring Cindy back into our house, how would Angie react?"

"Not good."

"So why are you pushing?" He was unreadable.

"I guess because I feel guilty about what I did to you."

"Want to make it up to me?" He nodded. "Then fix things with Angie. I care more about her and Kyle than I ever will care about Cindy and me. Does it suck that I lost a friend? You bet. Do I want your help with Cindy? HELL NO! We will deal with our own shit, and you and Angie need to butt out."

"Okay," Greg said as he pulled back onto the street, and we headed to school.


I headed to math class and took my seat. I couldn't figure out why everyone was giving me dirty looks until I remembered that I was only supposed to attend on quiz and test days. I gave a little chuckle and let them squirm. The girl who took my quiz sat in front of me. She gave me a shy smile before she sat down. The guy on the swim team that accused me of getting special treatment came up to her and said, "Did you make me a copy of the extra credit?"

She pulled a sheet of paper out and handed it to him. He gave me a dirty look when he saw me watching him. I don't know why he thought he was so tough. I was four inches taller and 20 pounds heavier. I hated bullies. I couldn't tell if the girl in front of me was giving him the answers because she wanted to.

Mrs. Sinclair came in and got ready for class. I just ignored the situation and concentrated on class.


At lunch, the football team seemed to be huddled around a couple of tables. When someone noticed me, they all got quiet. Crap. This couldn't be good. I walked over, and Kevin handed me a fax. It was the All-Conference selections. I scanned the list and saw that Kevin and Luke were first team selections. Magic was a second teamer. I wasn't even honorable mention. First team at quarterback and player of the year was my newest buddy, Mark from Eastside. I smiled to hide the twinge of hurt.

"Congrats, guys. You all deserve it. I'm disappointed to see that Bill didn't make the team. His stats were much better than the guys on first and second team were, but I'm only seeing seniors. I guess he didn't get on because he wasn't a senior."

Everyone seemed to agree and didn't look so sullen. Of course, Mark was a junior, but I wanted to focus on something else. I vowed if I ever got a chance to play against Eastside again that there would be no doubt about who the better quarterback was.

I went over to our usual table. Suzanne and Cindy had their heads together. I listened to Alan and Jeff talk about playing a new Grand Theft Auto video game. I hoped it would end up under my Christmas tree this year. Gina sat down, listened for about two seconds, and turned to me.

"I see you are a celebrity."

"I take it my interview from last night is on TV."

Now everyone was curious, so I pulled out my phone and played it for them.

"You are going to be swimming in pussy when they see you in that suit," Alan said laughing.

Thwack...

"OW!"

Jeff did us all the favor of smacking his forehead.

Luke decided to chime in.

"First we have Superman. He even dresses up for Halloween in tights. Then he works it so he rides with all the cheerleaders to the game. He gets off the bus and within two minutes he has this really hot, and when I say really hot, I mean smoking hot, girl wrapped around him.

"Then on Sunday night, he becomes the 'Mystery Man' at some socialite's party, and he looks like a male model. What's next? He shows up for Prom with Kate Upton?" Luke said, unable to contain himself.

"I'll get my people working on that," I said with a straight face.

The serious look on Luke's face caused everyone to crack-up.

"If there is anyone who can get a supermodel as a prom date, it is David. So you all can laugh, but I have confidence in my boy," Luke said, looking around the table.

"Luke, I can't go to Prom. It is for juniors and seniors."

"You get Kate Upton to say yes, and every junior and senior guy will make sure you get in."

"And some of the girls," Suzanne said, smirking.

That got a few eyebrows raised.

"Okay, let me get it set up." I pulled out my cell phone. "Kendal ... David."

"Good morning 'Mystery Man'. I like the sound of that. I'm going to work on some marketing around your new handle. I need to get a copy of the video."

"I have it. I'll email it to you," I said. Everyone at the table had a deer in the headlights look. "I need you to work on something for me. I want to go to Prom with Kate Upton."

I heard the phone hit the floor and Kendal laughing. I turned to everyone waiting to hear what she said so I put her on speaker.

She picked the phone up.

"I LOVE that idea. I can see it now. Fifteen-year-old 'Mystery Man' aka 'Superman' gets the hottest woman on the planet to be his Prom date. If you're serious, I will get Lily to start a twitter campaign," Kendal said.

"No way," Luke said, hitting his head on the table.

"This sounds like fun. Get Lily started," I chuckled. "I want to see Luke's head explode when she walks through the door. Thanks, Kendal, you're the best."

I hung up.

Gina turned to Alan. She had a weird look on her face.

"Sorry, but your best friend makes me hot. Either you give me a free pass, or we are breaking up."

Our eyes got very big. I held up my hands.

"Whoa there, not happening. Alan is my best friend."

"Alan is right. You are going to be swimming in pussy," Gina pouted.

Alan for once kept his mouth shut. I think he realized that Gina was semi-serious. The rest of lunch was taken up with people teasing Luke about who I would get as his second date. The reasoning went that if I had two dates to Homecoming I would have at least two for Prom.


During fifth period, it was announced that Eastside won the coin flip and would be going to State. Representatives from all three teams had met at a local restaurant with an official from the High School Association. It was decided that each one would flip a coin at the same time. If there were two matching coin, they would go to a head-to-head coin flip.

The first round, all three had heads. On the second round, both Eastside and Lincoln had tails. Since they beat us they were allowed to call the final coin flip. The association representative flipped the coin and Eastside called heads. It came up heads to send them to the state football playoffs as our conference representative.

There was still the outside chance that we could get into the playoffs as an at-large selection. The committee would be choosing the final teams later in the day.

I had mixed feelings if we did not make it in because I felt our team was much better than Eastside. We might have a chance to win it all. Then I thought about having my body feel normal again. There was always a silver lining.

In my last period, I got a text letting me know that we were all to report to football practice tonight. Coach Lambert had us meet in street clothes in the gym.

"I just wanted to let you all know that I am proud of how you all played this year." He started things off. "Would Bill and David come down please?"

"I was embarrassed when the All-Conference list came out today. You both should have been first team. I just wanted to acknowledge my appreciation of how well you both played this year. The good news is that you will get some revenge. Our first State playoff game will be Wednesday against Eastside!"

Hell, yes, the team went nuts, rushing the basketball court. When we finally calmed down, the coaches broke us up into offense and defense, and we went to watch film of Eastside. The first time we played Eastside, I only had Luke and Bill as weapons. Now I also had Wolf and Ed. I was going to run up the score if Coach Lambert would let me.

Coach Engels ran the offensive session. He gave us an overview as he saw it.

"This is going to be a close game. Eastside's defense plays against a passing offense every day in practice." He looked around the room to make sure he had our attention. "Our biggest advantage is that they are used to the West Coast Offense. They will try to keep everything in front of them because they are used to that style of short passing game. We are going to stretch them and force them to make plays. The other advantage we have is Wolf. Their defensive backs are small and fast. Wolf's size will cause them problems. If we can get them to switch a linebacker to him, we will have a huge advantage."

After practice, I was not as confident as I was going in. The long passing game was high risk, high reward. If things went our way, we could blow them out. If not, well, I didn't want to think about that.


I walked out of practice to find Cindy waiting on me. I had time today to think about what I wanted to say. I planned out the conversation. She just never gave me a chance. She grabbed me, and next thing I knew our lips were locked in a death match. She made me forget that we were not supposed to be doing this. That was the disadvantage of being a fifteen year old boy. A hot willing girl was very hard to resist. When she was Cindy Lewis, I had no friken chance.

It didn't help that she was wearing her naughty catholic school girl outfit. Something about knee high socks, a plaid skirt, and a white button up blouse got me hard instantly. I ground my dick into her stomach and showed her my need. She grabbed my hand and dragged me behind the shop building. We had more privacy, but we were still exposed. I put my hand on her shoulder, and she got the idea. She kneeled before me and pulls my sweats down. I didn't have anything else on so my cock was free. She took advantage and sucked the head into her mouth.

I grabbed the back of her head and started to fuck her face. I could tell this was going to be quick. I saw in her eyes that she knew I was going to cum fast. I tried not to push too deep because her gag reflex was pretty strong. I used short fast strokes to bring myself off. I felt my balls tighten, and I sprayed her tonsils with cum. I painted her mouth with the next few offerings. Cindy was a champ, and swallowed it all.

"You are a walking wet dream," I gasped as I tried to catch my breath.

She looked up at me with cum shining on her lips. She made sure I was watching as she licked it off. Damn, was that hot. She smiled when she saw the look of lust on my face.

"I take it you are not mad at me."

"You have every advantage. Queen of the hot chick clique, wearing my kryptonite, a school girl uniform, and you just sucked my dick. I would be insane to be mad at you."

She stood up and kissed me. I could taste myself on her tongue, which was what I think she intended.

"Will you help me fix things with Angie?" She asked.

"Are you going to fuck me stupid?"

She turned around and put her hands on the wall. I shuffled forward because my sweats were at me knees. I flipped her skirt up, and the site of her ass brought me back to full hardness. Her brown rosebud was inviting, but I wasn't experienced enough to know what to do. I did know how to fuck her. I rubbed the head of my dick up and down her slit. I ground it against her clit until I heard her moaning.

She was dripping by the time I slotted my dick. I took her with one powerful thrust and then just pounded her. She had the body that could take a hard fuck, and she went nuts.

"Oh, David, give me that cock!"

I felt the walls of her pussy clamp down hard and hold me in place. It was then that I realized that I did not have a condom on, but it was too late. I came with her.

"I am so sorry. I forgot to wear a condom," I said, pulling out of Cindy.

She smiled at me.

"Don't be. Suzanne told me you had been checked, and I'm protected. She and I talked, and she is fine if you go bareback with me."

"Cindy, this has nothing to do with you personally. However, would you get tested? I'm more worried about where Greg and your exes have been than you."

Cindy froze for just a second but she took it well. Thank God for small favors.

"I see what you mean. My ex is almost as big a slut as Greg. If we are going to do this, you and Suzanne have a right to protect yourselves. I'll go get a test tonight after I drop you off."

"Thanks," I said. "Greg and Angie told me about this weekend. Out of respect to Angie, I can't take you home right now."

"I understand. Do you want to talk about it?"

"Actually no, I don't."

We walked around the shop to the parking lot. There were about ten guys standing around. Our appearance left no question where we had been. My first thought was that I would need to defend Cindy. I underestimated the power of the Queen of our school. She gave them a withering look and said in a voice that left no room not to obey.

"If I hear one negative thing about me or David, I will make it my life mission to see that you are dateless for the rest of the year."

She made eye contact with each one of them, and Kevin stepped forward. He added his weight behind her words by saying, "And I will kick each of your asses."

I had no doubt that it would be all over school come morning. These were horny teenagers that had juicy gossip. The only way to keep them from talking would be to put a bullet in their heads. I just hoped I got home before Angie found out. I needed to tell her to her face instead of letting the gossip mill distort what happened. I let Cindy lead me to her car, and she dropped me off at home.


I went up the stairs of my apartment with a heavy heart. I didn't want to face Angie but took a deep breath and found her sitting with Kyle on the floor. She saw me come in and the look on my face.

"Are you not going to State?" She asked.

"Yes, we play Eastside this Wednesday." I straightened my back and faced her. "I have something to tell you."

"Oh hell, let me guess. Greg banged his math teacher."

"Pam Lowden?" I asked.

Her eyes got big and before she stroked out I said, "I already did her." Crud, I wasn't supposed to say that.

"YOU DID NOT!" She screamed. She looked at me closely and then yelled, "OH MY GOD YOU DID!"

"Angie, cool it," I said, making hushing motions. "Teacher/student sex is a big no-no. She could go to jail!"

I collapsed on the couch.

"I'm so messed up. I can't believe I told you."

She got up.

"You wait right here. I'll be right back."

She thrust Kyle into my arms.

"Hang on, I still need to apologize."

That stopped her.

"What did you do?"

Wow, she had the Mom voice down already. Kyle was so screwed.

"I don't know how to say this so I will just tell you. I was with Cindy today."

She made a circle with her thumb and index finger with one hand and slid another finger into the circle in a fucking motion.

"You mean..."

I dropped my head. She half turned from me and bit her lower lip. Her shoulders started to shake. This was my worst nightmare. Then she broke out laughing. "David, you are not my boyfriend. I could care less who you are sleeping with. As a matter of fact, I think you should sleep with Cindy. She has a great body. Now wait here."

What was she up to? After several minutes, she came back with Greg. He looked at me in confusion, and she had a pissed off look on her face.

"Tell him what you did," she said, turning to me.

My face went beet red as he glared at me. I looked at her panicked.

"Which thing?" I asked.

"There is more than one thing?" Greg turned to her and asked.

She patted him on the arm as if he was an idiot.

"He's a Dawson. I want you to tell him the first thing."

I shook my head.

"No, I absolutely cannot talk about that and you know why. I can't believe I told you."

She crossed her arms and tapped her foot.

"David, either you tell Greg now, or he will hear it when I tell your mother."

Greg had been watching this like a tennis match.

"Tell me what?"

We stared at each other to see who would blink first. I caved, which was nothing new, and I was not proud of it.

"If I say, you both have to promise not to say a word to anyone."

Angie looked at Greg.

"Okay, the one thing he is good at is keeping his mouth shut. Now tell him."

I thought about it for a minute.

"I slept with Pam Lowden Friday night."

Greg's eyes got big.

"NO! Fuck ... Fuck ... Fuck ... You suck so bad David!" He cried.

Angie had a huge shit eating grin on her face.

"Pam is one of the three names Greg has on his list for a free pass. He has been working for almost a year on her."

Angie was almost in tears, she was laughing so hard.

Greg pouted big time.

"How did you manage it?" He asked.

"I took my shirt off."

"No fair," Greg said.

"I can see that working," Angie said.

I looked at Angie.

"Who else is on his list?"

She looked at him, and he nodded giving her permission to tell me.

"One will make sense and one is a complete fantasy. Cindy and the other one is Kate Upton."

"Great minds think alike. I'm taking her to Prom," I smiled at Greg and said.

"I'm sure you will have a great time with Cindy," Greg shrugged.

"No, Kate Upton."

"Get out of town. You are just messing with me aren't you? David did not sleep with Pam."

I held up one finger to slow him down, and I pulled out my phone.

"Hey Kendal, is it okay if I put you on speaker?"

She agreed so I switched the settings.

"I'm here with my brother and his girlfriend. Can you tell them who you are working to get as my Prom date and what progress has been made."

"We are working to get Kate Upton as David's date," she didn't hesitate in saying.

There was a big thump as Greg faked a heart attack. Kendal went on.

"Lily put it on your website and sent a couple of twitters to Kate's account. One tweet had your 'Mystery Man' TV interview. Lily said that we have received three offers to be your Prom date so far."

"Any of them cute?"

"Let me just say that one of them is a little aggressive. She sent pictures, and before you ask, I deleted them. She must be a porn star."

"KENDAL! You forget you are working for a fifteen year old walking hormone."

"Buddy, you hired me to look out for your best interest. Trust me, if she was cute, I would gladly send those pictures on. Can we just say I did you a favor?"

"I trust your judgment. Hey, it looks like my brother is getting off the floor. I'll talk to you later."

"If you think of anything else fun like this, let me know. Tom and the other partners want to worship the ground you walk on after I told them your idea at our meeting today. My guess is that they will all be going to Prom if you get her to say yes."

"Yeah, Tom is a dirty old man."

I heard her bark with laughter as she disconnected, so I turned back to Angie.

"Cindy huh? I guess that gets him off the hook for Saturday."

She nodded.

"Who is on your list?" I asked.

They both looked at each other. Greg nodded.

"I only have one name on my list. You." She said.

I was stunned. I had made it clear that I was not going there.

"We know what you said. But when it happens, it is not going to destroy our relationship," Angie said.

"What do you mean, when it happens?"

"We both know that you and I are attracted to each other. So don't even try and deny it. Over the next 20 or 30 years, I'm going to catch you at a moment of weakness and have my way with you. When it happens, I don't want you freaking out like I know you will. And just so you know, these passes are a one-time thing."

That made sense. Cindy was now off the table for Greg. I really can't see me allowing her pass with me, but that didn't mean I couldn't tease them about it.

"So what counts as one time?" I asked.

"Any time you stick you dick into my girlfriend," Greg said, giving me a look.

"So is there a difference between a quick blow job after school or a long dicking over a three day weekend."

If looks could kill, I would have been struck dead. Angie got into the spirit of things.

"Good point. I think a long weekend would count as one pass."

"Would I need a pass for each place I put my dick?"

"If you are not careful, I am going to kick your ass," Greg growled.

I gave him a weak smile.

"I think the days of you being able to take me are over."

"You want to go outside and find out?"

"Boys," Angie said, stepping in between us with arms outstretched.

I laughed, and she said. "What's so funny?"

"I'm just thinking how screwed Kyle is. Your mom routine is perfect. You have both of us backing down with just the tone of your voice. Talk to mom, she can give you some tips on being really scary."

"Shut the hell up. She uses that on me," Greg whined.

I hit my forehead.

"Sorry Bro. You're screwed, too."

She turned and looked at Greg.

"I want all three of my passes for David."

"NO!" we both said.

She just grinned and took Kyle back to the house. Greg shook his head and followed her. I don't think either one of us knew if I had all three free passes or not. I would let them sort it out.


Wednesday November 13, 2013 – Freshman Year

The state playoffs were finally here. This was our first appearance in many years so the community was excited. Tuesday I went to Jerry's for some ice cream with Cindy, Suzanne, and Jim. My ice cream melted because I ended up talking to everyone about the upcoming game. The playoff news was slowing down the gossip about Cindy and my public display on Monday, which was good news for her. A few of the braver guys asked her out. We went to Jerry's to be seen in public. Cindy could now have some cover and slow down the advances.

We got lucky and Eastside had to come to us to play. At first, the school board wanted to play the game at a bigger stadium to handle the crowd. The community made its feelings on that loud and clear. They wanted the game played at home.

Kendal turned over the running of the pre-game party tent to the newly formed booster club. They were the same group that arranged for Bo. There was some serious money there. Kendal told me that they were reserving busses for fans in case we won and were on the road Saturday.


After warm-ups, we got our final instructions from the coaches. As we lined up ready to run onto the field, I looked at the seniors and recognized that this may be the last time they played in front of their home fans. I was proud to be on their team. As we ran out, the marching band played our school song, and we ran through a banner held up by the cheerleaders. The place rocked and I could see it was standing room only. This was what high school football was all about.

Once we were settled in on our sideline, the Eastside team ran out to the loud support of their fans. I took the time before Kevin and I had to go out for the coin toss to look for my mom and dad. I found them and was surprised to see that Greg and Angie were there also. They must have found a sitter for Kyle. They all had on Double D Fan t-shirts. They all saw me and waved. I pushed them out of my mind and focused on my pre-game ritual of visualizing plays. One play just seemed right.

"I want to run Quarterback Draw on the first play," I said, going up to Coach Engels.

"Normally we need to set that up, but I think they are going to blitz you from the very first play. I think this will slow that down. Go ahead and call it," coach said.

Coach Engels sent me out to the coin flip. Four Eastside players were waiting for Kevin and me. As I expected, Mark was there. Before he could be a jackass, I shook his hand and said, "Congratulations on making All-Conference."

That pissed him off because his face went red. They won the coin flip and deferred to the second half. When they kicked off, the sun was just setting on a perfect evening. Eastside had a good kicker so we downed it in the end zone and got the ball on the twenty yard line. I called two plays on the sidelines before we ran out and lined up. Eastside took their time and the referee blew the whistle to make the play live. I made the call for the snap to be on first sound.

"BLUE!"

There was a large gap on their side of the field where their safety and cornerbacks had not gotten into position yet. I took a two-step drop and then tucked the ball. The play was designed to go up the middle, but I took off around the right end. I outran their defensive end and outside linebacker. Their cornerback on the open side of the field had blazing speed and caught me after I crossed the 50 yard line. I saw that he was breathing hard and decided to take advantage.

The next play was a hook to Wolf intended to keep the chains moving. We practiced the no huddle for the past two weeks, but had not used it in a game. I yelled, "ON THE BALL ... ON THE BALL..."

I then changed the play, "CHECK ... CHECK... 52... 52..."

I flipped the formation so that Bill was lined up with the corner that chased me down. I called double move that would freeze the corner for a moment giving Bill the chance to run by him.

"BLUE ... SET ... HUT HUT!"

On the snap, I saw the backside defensive end make a move on our left tackle. A couple of weeks ago, he would have had a free run at me. Luke was paying attention, stepped up, and slowed him down enough so the left tackle could reengage. Confident I wasn't going to be blindsided, I pump faked when Bill made his cut. The corner bit on the fake and closed on Bill. Bill planted his foot to change direction and sprinted up the sideline. I lofted the ball 30 yards in the air and Bill caught it in stride. Their corner simply did not have enough to catch Bill.

I could feel it from the very beginning that I was in the zone. Unfortunately, so was Mark. On their first series, one of our defensive backs slipped on an easy tackle and they scored. Less than 3 minutes into the game, we were tied 7-7.

On the next series, we switched to our read option running game. Our goal was to get Luke and me into their secondary and pound on their small defensive backs. Coach Engels plan was to work them as you would a fighter. Enough body blows and it would become easier to knock them out in the later rounds. We made a point to fight for every yard and to put a hit on anything in the way. By the sixth play of the drive, their defensive backs were losing form and trying to take our legs out instead of meeting us head on.

That was when I let Wolf loose. I ran three short pass plays to him and let his 6'5" 240 pound body work on them. On the third pass, he had two of them hanging on him as he powered into the end zone. Mark led Eastside back to another quick score when Magic went for an interception and missed. Kevin was taking it better than I expected. The first touchdown someone slipped and the second was an aggressive play.

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