Stupid Boy - Cover

Stupid Boy

Copyright© 2014 by G Younger

Chapter 18: Truth or Dare

Coming of Age Sex Story: Chapter 18: Truth or Dare - 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 17, 2013 – Freshman Year

I woke up Sunday morning stiff. I crawled out of bed and got into a hot shower to help loosen my muscles. I went out into my living room and did the stretching exercises that Jill taught me. The way I felt, I would be surprised if I could practice on Monday.

While I was stretching, I got a text from Tami to get on video chat. I pulled on a t-shirt and got my chat app started. No surprise, it was Jennie. I thought about just turning my connection off. What surprised me was I didn't feel hurt about her leaving yesterday. What was it that my uncle said? The opposite of love is not hate; it is indifference. Until just now, I really did not know what he meant.

"I take it you are hijacking Tami's stuff again. Is she around?"

"No, she went to breakfast. I just wanted to say I'm sorry I bailed out on you yesterday."

"Jennie, don't worry about it. I didn't get out of the hospital until late and I went straight home and went to bed, I couldn't go out with you anyways. So I guess everything worked out for the best."

Jennie was used to guys fawning over her. She was rich, sexy as hell, and had a nice personality. For me, she was too much work. If pressed, I would say she was self-centered.

"When can I see you next?"

I was a little surprised when she asked. I thought about it for a minute, and then I remembered when I would see her.

"I'll see you at the Christmas Dance. I promise to save you a dance."

I could see the wheels turning. I told her I had to go to church and logged off. I got a text two minutes later from Tami saying she missed me. I logged back on, and it was Jennie.

"If Tami has a date, will you go as my date to the Christmas Dance?"

I didn't like the sound of that. With my luck, Jennie would fix Tami up with Mark. She was starting to piss me off.

"Why are you pushing so hard?" I asked.

"What are you talking about? I'm just trying to spend some time with you. If you don't want to see me just say so," she whined.

"I thought we agreed to be friends. You obviously had somewhere better to be last night."

"So that's it? I can't stand to watch you get pummeled, and suddenly I'm the bad guy?"

Did she really just try to turn this around on me?

"Okay, you asked me a couple of questions. I think if I answer them, it will help clarify things. Do I think you are the bad guy? The answer to that one is I don't know. That would depend on what you did last night. Did you go on a date with someone? Did you go to a party?

"The question that irritates me is asking if you find a date for Tami will I go with you. The answer to that one is, if Tami finds someone she would rather go with, I won't be going."

Tami walked into her room.

"Hey, David, I hear you and Jennie had a good time last night."

I could see the guilt on Jennie's face.

"Yeah, we had a great time. I'll let Jennie fill you in on all the details. I'm just a 'stupid boy' and I might miss some of the great things we did. I have to go to church. I'll talk to you later."

"I'm so sorry," Jennie said.

I turned off my link. I went down to the house and grabbed a bowl of cereal. Mom came out in her housecoat, and she looked worse than I felt.

"I vote we go back to bed and skip church this week," she said.

"I agree. Are Angie's parents coming for lunch?"

"No, I think they have washed their hands of their daughter," Mom said.

I finished my cereal, went back to my apartment, and crawled back into bed. I got another text from Tami. I logged into the chat and she was alone.

"David, why is Jennie crying? I thought she came to see you yesterday."

"She just got caught cheating on me."

"Cheating on you? What did she do?"

"Tami, she came to the game, according to my parents. Before the first quarter was over, she took off ... claiming she couldn't watch me get hurt. Apparently, it was to meet someone else. You just confirmed my suspicions."

Tami figured it out.

"She went out with Mark!"

I chuckled.

"If she did, I will never ever see her again. I hate that douche bag. She actually asked me if she found you a date for the Christmas Dance if I would go with her."

"That's an easy one. You wouldn't go because you couldn't stand to see me with another guy."

"You know me too well. I would be happy for you, but I just couldn't watch it."

"Speaking of dating, are you still on hold or do you want me to set you up?"

"I actually got my own date. I'm going out with Peggy on Friday."

It was out before she caught herself.

"Nope, bad idea."

She could see the hurt look on my face.

"I can't really say I didn't mean it, but I can say I shouldn't have said it."

"So are you saying I should cancel my date with my dream girl?" I sighed.

"The short answer is yes. The problem is I know you. You are going out with her no matter how bad of an idea it is. David, answer me one question. Do I love you enough to tell you things that you don't want to hear?"

"Yes."

I didn't even have to think about that one.

"I know you don't want to hear this, but don't go out with Peggy right now."

She had tears in her eyes and I knew this was costing her to tell me this. The two women that know me the best had both told me not to date her right now.

What a shitty morning. I had this crush forever, and I was about to turn down a date with her. If Tami had not shed some tears, I would be ignoring my Mom and her. I could tell when Tami was faking, and she was not beyond crying to get her way, but these tears were real. She knew how much this meant to me and it was killing her to tell me. I only had one option.

"Okay, how do I break our date without her deciding to never go out with me again?" I asked. "If that happens, I'll not be a happy boy."

She took a deep breath.

"I'll take care of it. You just did the hard part. She will wait. She has as big a crush on you as you have on her and she has had it for a very long time."

My eyebrows went up.

"And you are just now telling me that."

"We both know you weren't ready for Peggy. That is why you got Greg to help you in the first place. For Peggy, it was different. She knew you didn't have enough social status for her to be able to go out with you until now, and don't give me any crap lines about it not mattering. This is high school. A junior girl can't go out with just any freshman. Well, unless you are at the top of the heap like Cindy and Suzanne. Peggy is popular, but she could never pull it off."

"Someday your looking out for me is going to backfire," I said while shaking my head.

"I'm sure it will, but you will love me anyways."

"There is that. So back to you setting up dates. Your track record sucks. I think I'm out for right now."

"I had no idea Jennie would turn into a cheating bitch. I just thought she had some insecurity and lack of maturity issues. You have the confidence to hold it together, and I figured your maturity levels matched. If what she told me is true, the sex was unreal. Did you really make her cum for almost an hour straight?"

"Come home for Thanksgiving and I'll show you."

She saw my evil grin and her eyes got big.

"Hell no, I would die if I came that much!" Tami shivered.

"What is it with you women? I prove I can make one of you cum over and over again so hard that you worship me as your sex god, and the rest of you are scared I might ruin you for every other man you might be with."

"Oh my, I'm going to have to talk to someone's Mom. She needs to beat some humility into your tiny little brain 'stupid boy'."

I gave her a stern look.

"If someone's Mom is talked to, the talker will end up over my knee. I know this might surprise you but I can actually do it now. So I would be careful when talking to parental units."

"You would spank my bottom?" She giggled and asked in a little girl's voice.

"Tami, you bad girl, I may have to think of something else because I think you would like it too much."

What I loved about her was that she could give it as good as she got it. That was why she always fit in when we played little league. The guys always accepted her as one of our own. She then suddenly had an idea. I could tell because whenever she gets that look on her face, I get nervous. It usually means one or both of us were about to get in trouble. She was smarter than I was, so it was usually me.

"David, you want to get even with Jennie?"

Oh, this couldn't be good. I gave a slight nod not wanting to commit.

"This Sunday we are having a mixer. Parents and alumni will be here. I overheard Jennie saying that her sister, Carol, had to come and her boyfriend Tom wasn't able to escort her. Jennie is trying to find someone to take her. What if I set you up with her?"

"Okay, this sounds like a disaster. The big issue is that I'm 15 and not planning on relying on the Wesleyan's to provide transportation."

"My Mom is coming up. She will give you a ride."

"Wouldn't this be better if I took you?"

"No, Jennie could make my life a living hell."

"How will we keep your involvement secret?"

"Easy, you will call her and set the date up," Tami smiled.

I thought about it for a minute, and I suddenly realized that Carol put her number in my phone. I got my phone out, and called Carol.

I heard her answer.

"Hello."

"Carol, it's David, I need to ask you a favor."

"Hey good looking, what can I do for you?"

"I was just talking to my best friend Tami. I guess Wesleyan is having some kind of dance on Sunday. I want to come up and surprise her. I can get a ride from her Mom, but I was wondering if you knew of anyone I could take as my date?"

"Wouldn't she want to be your date?"

"No, Tami and I are friends. I hear this is a mixer, and I don't want to look like the boyfriend from home. I'm just looking for some cover so I can go and have some fun."

She thought about it, and then threw up one last objection.

"Why not take Jennie?"

"I guess you haven't talked to your sister. She came up to my game yesterday and left early so she could go out with someone else. I don't think she's interested in me anymore."

"Oh, in that case, I know who you can go with, me."

I paused to make it look like I was considering it. I had the hook set. Now, I just didn't want to spook her.

"Carol, are you sure that is a good idea? Jennie is your sister and I'm not looking to cause trouble."

She actually laughed.

"That little bitch has pulled this kind of stuff all her life. I'm going to help you get a little payback?"

"I know that sounds like fun, but I like Tom also. I don't want to see him hurt."

"Hang on a second," she said.

I heard her talking to someone and I was surprised when I heard Tom laughing on the other end. Tom was Carol's new boyfriend.

"Hey David, I hear you are taking my gal out? Actually, you are doing me a big favor. I made the mistake of making plans without checking with the boss. You just saved me from a week of her working on me until I canceled my plans. To answer your question, you are doing both Carol and I a favor."

I heard more muffled talking and Carol was back on the line.

"David, do me two favors. First, please wear that suit you wore at my cousin's engagement party. I want every girl jealous that you are my date, and second please don't tell Jennie. I want to see her face when you walk in on my arm."

"I can do both. Actually, I'm pretty sure she isn't going to be talking to me. She knows I found her out."

"Hey, I'm sorry. Jennie will someday make a man very happy. She just needs to grow up and realize that the world doesn't revolve around her. I'll make you one promise. We will have a good time. I also can't wait to meet your best friend."

"Carol, you'll love her. Tami is a great gal. I think you girls will hit it off."

"I look forward to seeing you, David. Tom and I like you a lot. I'll call you later in the week. Have a great weekend."

"Carol, it's better already. I'll talk to you later."

I hung up and smiled at Tami. I could see she was pleased. Her evil plan was coming together, and she was excited. Something more was getting her worked up.

"Tami, tell me why are you are so excited?"

"Think about it David. There are about 50 girls in my dorm alone that will flip out when you show up. After your video chats, and everything, Jennie told them you might not be safe. I can't wait to see their reaction. It's going to be so hard not to tell anyone that I know you are coming."

"This could be so good, especially if Jennie brings Mark," I said. Then I shook my head. "Tami, are you sure this is a good idea? I mean, it makes my skin crawl to think of Jennie with Mark, but she could really be a problem for you. I want you to think about this."

"Don't worry about me. I can handle Jennie. She made this personal when she pushed her way into dating you. Then she treated you like shit every time she turned around. I know you're not mad at her, but you forget. I'm a woman and she messed with my man. I will have my pound of flesh."

I know better than to cross Tami when she gets like this. We firmed things up, and I hung up.


I was starting to hurt from all the abuse my body took yesterday. I got a Dixie cup of ice out of the freezer. I put water in the cup and then peeled them down so I could rub the ice on problem spots. My left elbow and my knees had some swelling, so I worked on them. I got out the massage cream that the trainers gave me, and I headed to the house.

I was hoping Mom was around, but she was still in bed. Greg and Dad were watching the pre-game show for football.

"I suppose you must really be hurting if you are looking for us to help you out," Greg smiled.

"I know, you would think I could find a female, but I think I'm losing my touch."

"Get your skinny ass over here and I will do it. This comes with a price, you know?"

Greg was still worried about Angie saying she wanted me as all three of her free passes. I was sure he knew we were just giving him a hard time, but he was not taking any chances.

I gave a fake sigh.

"I will give up one of my free passes if I have too, but you have to tell Angie."

He quickly agreed. I gave it a 50 – 50 shot he had the balls to tell her. He had me lay on the floor so he could watch the game on TV. I stripped down to my shorts.

"Wow, I know you get hit hard, but are you sure it is worth it?"

I just shrugged and he got started. If he were a girl, I would marry him. Greg had magic hands. I was moaning as if I were his bitch. Dad actually sounded like a schoolgirl when he started to giggle. Angie came down stairs and had to poke her head into the TV room. I think she thought I was having sex with someone. She disappeared and a minute later, she and Mom came strolling in. I didn't care. I just kept moaning every time he worked a knot out of my back.

When he was done, I couldn't move. I just lay on the floor enjoying the effects of his massage. Angie soon joined me on the floor, and he gave her a treatment. Her eyes locked with mine, and she began moaning. I just smirked knowing exactly what she was feeling.

"What is he using?" She asked.

"That is something I get from the trainers. It feels like heaven."

"Yes baby, you keep that up and you are getting special sex tonight," Angie moaned.

"No he won't. You won't be able to get off the floor when he is done," I snorted.

Twenty minutes later Mom joined us. Greg had us all half-naked and in relaxed puddles. Greg offered Dad, but he wanted to watch the football game, his loss. Mom said something that changed Greg's life.

"You should do this for a living."

Angie popped up and smiled at Greg.

"I would pay to learn to do that. If I could give a massage like you just gave me I would never lose a girlfriend," I rolled onto my back and said.

"Your Mom is right. You can do this part-time and make more than you do working at the hardware store. You can also teach David, and he can work for you. Do you guys know how many women would pay a premium to have one of the Dawson boys put their hands on them? I can do your bookings. Baby this could be our answer to our prayers for paying for school and having time to do it."

Angie and Greg left the room to plan their new business venture.


My favorite team, the Bears, were playing a night game. So I didn't feel like watching football with my Dad. I talked my Mom into taking me to the arcade. I was actually surprised it was still open. Most everyone played games on their computer now. They got smart and setup group games, like Black Ops, in small rooms with a four-player setup. Everyone had his or her own monitor. I loved it because, unlike sitting at home with a headset on, I could actually reach over and smack Jeff or Alan when they shot me in the back. We rented the rooms for $20 per hour.

For me, the main reason I liked the arcade was pinball. I confess, I was addicted. I loved the lights and dings as the ball bounced around. The trick was shaking the machine, but not too hard, or it would go on tilt. I just finished a game when I noticed the smart girl from math class come in. If girls ever figured out that 90% of the customers were horny teen boys, it would be the next pickup place. I was deciding what game to play next when I noticed four guys had the girl cornered. I eased over to see what was going on.

"Listen, Sun, we will buy you lunch, but you have to be nice to us."

I guess math girl's name was Sun. Why would he be offering her a lunch for sex deal?

"I would rather go hungry, besides I'm meeting someone. So leave me alone," Sun said.

The guys didn't look happy. The ringleader was looking pissed.

"Come on, we can have some privacy in the bathroom," He said, grabbing her arm and starting to pull her to the men's room.

To my surprise, she didn't say anything as he started to drag her off. He had to go by me to get to the bathroom so I stepped in front of them and smiled.

"There you are. I was wondering when you were getting here."

Sun looked up at me confused and then she smiled.

"Sorry, David, I got sidetracked."

She turned to the guy holding her arm, and he looked up at me and let her arm go. Being 6 foot 2, I towered over most other freshman. I recognized John from one of my classes. He was a bully, but at 5'5", he was not going to take me on. I reached out my hand, and she took it.

"Sun let's go get a bite to eat and then we can plan our afternoon."

I led her out of the arcade, and we walked over to Monical's. I admit it. I can eat Monical's pizza seven days a week. I was planning to get a pizza anyways. What surprised me was on the walk over Sun never let go of my hand. We didn't say anything. She was deep in thought so I didn't bother her. We got a booth and the waitress took out drink orders. Sun was giving me a strange look.

"What do you want on your pizza?"

"Pepperoni."

I was a mid-western boy, and I liked sausage on my pizza. When the waitress came back, I ordered a large half pepperoni, half sausage pizza, and their family style salad. It comes in a big bowl, and everyone at the table serves themselves. I watched in amazement when this little girl ate as much as I did. We had the salad gone by the time the pizza came. The first thing she did was grab a sausage slice. She saw my look and giggled.

"So you are a pizza thief."

She just shoved half a slice in her mouth and grinned at me. I guess she figured if her mouth was full, she didn't have to talk. I crossed my arms and waited. When she finally swallowed, she got a glint in her eye, and snatched another one of my slices. She shoved that one in her mouth also. I must have looked funny because she almost choked while trying not to laugh at me. I grabbed a couple of slices in self-defense. We ate in silence with me keeping an eye on my last slice. Sure enough, she snatched it and took a huge bite.

When I finished my two slices, I went to grab a peperoni slice. She smacked my hand.

"Hey bub, what do you think you're doing? I ordered the peperoni."

"Okay, we can play this game. I will wait and eat whatever you can't finish."

I figured that was a safe bet. Sun couldn't weigh a 100 lbs. soaking wet. I watched in amazement over the next fifteen minutes as she finished off the pizza. When she ate the last piece, she leaned back and burped. We both broke out laughing.

"You are such a lady."

She got tears in her eyes and looked like she was totally going to break down. I got up, slid into the booth next to her, and pulled her into my arms. She buried her face into my chest, and I could feel her shaking. I just stroked her back and gently rocked her. The waitress came and saw what was going on and gave me a tight smile of understanding and left us alone.

"Do you want to tell me what is going on?"

"No."

After being around her, I knew she needed a shower. I looked at my watch. Mom was picking me up in a few minutes. Something was not right.

"Would you like to come to my house and hang out?"

I think if I hadn't been blocking her escape she would have run.

"Look, I think you have guessed that I'm pretty smart," I sighed. "I know something is wrong. I know you don't want to tell me. I'm fine with that. What I am offering is for you to come back to my place and just hang out. Contrary to my reputation, I am not going to hit on you."

"We don't know each other. I don't think we have said two words to each other before today. Why are you being nice to me?" she asked.

"To be honest, I don't know. I saw what was going on in the arcade, and I was scared for you. When I saw you meekly being led, I knew you had given up. In that moment, I knew I couldn't let you go."

Sun was giving me an intense look.

"Before you think I am going all white knight on you, I'm not. Whatever is going on is beyond me. I'm not going to try to save you from it. I'm only offering you some time to just hang out."

"You're serious, aren't you?"

I nodded.

"I would like that."

I paid our bill, and we walked back to the arcade. To my surprise, she took my hand. I think she just needed the human contact because there did not seem to be any flirting going on. When we got to the arcade, she went in and grabbed a duffle bag. Mom was waiting on us when we got outside. Greg had trained her, so she didn't even comment when I had a girl with me. I got in the front seat, which did surprise Mom. I got the look that said 'we will talk later'. Mom and I ignored Sun and talked about my football game coming up. I also told her about going to Tami's mixer next Sunday.

When we got back to our place, I led Sun to my apartment over the garage. She was looking at my bachelor pad in awe.

"You live here?"

"I picked this over getting a car. My brother about had kittens because he didn't think of it first."

I gave her the grand tour. Okay, that took all of thirty seconds.

"Feel free to take a shower, and if you want the sheets are clean, you can take a nap."

"Are you trying to say I need a shower?"

"Yes, I am. Now go in there and get presentable. We will have dinner at six, and I don't want to have to explain why you smell."

She stuck her tongue out at me, grabbed her duffle, and closed my bedroom door. I went down stairs to talk to my Mom. She was in the kitchen talking to Angie.

"Just like your brother showing up with a new girl every week. Is she staying for dinner?" Mom asked.

"Yes, Sun is staying for dinner, and no this is not like Greg. I think she needs help. I suspect that she may be homeless."

"What makes you think that?" Angie asked.

I told them about what happened at the arcade, how she acted with the other boys, and about lunch and how much she ate. Then I told them about her need for a shower, and the duffle bag. My guess was that she was couch-surfing. That was where you go from friend-to-friend sleeping on their couch.

"Mom, this is beyond me. She doesn't want to talk to me. Can you talk to her after dinner?"

Mom may say whatever was on her mind, and it sometimes came across as uncaring. She was not like that at all. If Sun needed help, she would move mountains to help her.

"Just so I am clear, you are not interested in her as more than a friend?" Mom asked me.

"He's a teenage boy," Angie laughed.

"Yes there is that, but I actually think me not hitting on her will help more."

"I just wanted to make sure you were doing this for the right reasons. I'm glad you made the effort. Most people would have either not noticed or not gotten involved. I'll do what I can."

"Thanks Mom, I need to get back."

I headed back upstairs and I could hear the shower still going. I pulled out my iPad and opened the book I was reading, 'Beautiful Creatures'. Ridley was messing with Ethan and I was engrossed in the story. I came to the end of a chapter and looked at the time. It was 5:45. Sun must have taken me up on my offer of a nap since almost two hours had gone by. I gently knocked on the bedroom door. I heard a muffled, "Yes."

"Sun it is almost six. We need to get downstairs for dinner."

She opened my door wearing one of my t-shirts and shorts.

"My clothes are dirty, is it okay if I wear this to dinner?"

"Sure. I have to do laundry. Why don't we sort it and you can throw your things in with mine."

I walked past her, pulled out my laundry basket, and started sorting clothes. Sun opened her duffle bag, and added to my piles. When we were done, I dumped a pile into the basket, and we headed to the house. Sun watched as I pulled a load out of the washer, and put it on the dryer. It was a load of Kyle's things. I put my load in, and started the washing machine.

As we came out of the laundry room, Sun grabbed my hand. I acted as if I didn't notice, but she seemed to need the security of being close to me. Angie and my Mom noticed when we walked in, but neither commented. Greg and Dad just acted as if it was normal for me to bring a strange girl home. I introduced everyone to Sun, and she seemed to relax when they didn't give her the third degree.

We had a nice dinner, and this time Sun didn't eat as much. I think three-quarters of a pizza had filled her up earlier. After dinner, Mom led her off to the office to talk. I busied myself with doing another load of laundry. By the time Mom and Sun came out of the office, I had done all the laundry. When Angie figured out what I was doing, she had me do her and Greg's too. I had put all of Sun's laundry into her duffle bag. I was sure I didn't pack it right, what guy ever does, but I figured that she had about two weeks' worth of clothes.

When I got back, Angie told me to join Mom and Sun in the office. I knocked and Mom opened the door. She indicated that I was to sit in the chair behind the desk. She sat down next to Sun, and it was obvious that both of them had been crying. I just sat silently and waited. Sun finally smiled after several minutes and looked at Mom.

"You win. He really has been trained well."

"I can take no credit for that. He learned that from his Dad and brother. It is the most infuriating thing when they go stone quiet on you. The good news for you is that you can trust them to keep their mouths shut. It is your choice if you want to tell him or not. He will not treat you any different if you are not ready."

Sun got a sad look on her face.

"No, I'm sorry David. I am not ready to share this with you."

Mom patted her hand.

"Don't worry about it." She turned to me. "Sun is going to be staying with us for a while. We agreed that she could stay with you in your apartment. I only ask two things. Please do not bring any guest home while she is here, and don't share with anyone that she is staying here."

I didn't have anything to add, so I got up, and Sun followed me to my apartment. I made up the couch for her, and went into my room closing the door. I got undressed and went to bed. After I turned off my light, I heard a soft knock on the door.

"Yes," I answered.

"I need to use the bathroom."

"Come on in."

She did her thing, then came over, and sat on the edge of the bed.

"I want to thank you for not being nosy. It means a lot to me."

She leaned down and gave me a kiss on the cheek. I just smiled and she went back to the couch.


Monday November 18, 2013 – Freshman Year

I woke up to find Sun in my bed. She wasn't touching me, but I do sleep nude. My queen size bed had enough room that she wasn't on top of me. I slipped out of bed to take my shower. I came back into the bedroom and put on my underwear. I heard Sun chuckle.

I looked over and she gave me a silly grin.

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