Stupid Boy - Cover

Stupid Boy

Copyright© 2014 by G Younger

Chapter 20: Girls Confuse Me

Coming of Age Sex Story: Chapter 20: Girls Confuse Me - 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  

Wednesday November 27, 2013 – Freshman Year

Tracy and I had our first fight. It was because I was going out with Beth the night before Thanksgiving. For the past five years, Greg had always taken Beth out. I don't know what started the tradition, but it was our family's reminder that they would like to be joined more tightly than just friends. Each year Greg had gone out with Beth and each year they declared there was no spark and they were just friends. Mrs. Anderson and my Mom decided we couldn't possibly plan a romantic date. So it was planned for us.

Once Tracy got over being mad, she changed tactics. She got it in her mind that I needed to sleep with Beth and do such a good job that she would be jealous of what Tracy had. I can't figure out women. I don't know if it is me attracting the crazy ones or not, but Tracy had me tied up in knots trying to figure out if this was some kind of test.

Tuesday night Mrs. A, Mom, and Tracy picked out my wardrobe. I was surprised when they did not go with the suit. They went with a fitted black t-shirt made out of some kind of silky stretchy material. It was almost like not wearing a shirt because it showed every bump, ridge and ripple. They also chose a pair of slacks I wasn't fond of, because it felt like they were riding up my ass. The women all agreed it made my butt look nice. For some reason they all found a reason to squeeze my ass. Okay, my Mom didn't.

Tracy insisted on coming over to supervise me getting dressed. I was in my boxers heading to the shower.

"Hang on. I have to get you ready for tonight."

I was confused as to what she was talking about. She walked up to me and looked me up and down. Then she dropped to her knees and took my shorts down in one motion. Before I could react, she had my soft cock slurped into her mouth. I had to chuckle when she gagged from me going from soft to instantly hard. She grasped my base and gave me a satisfied smile.

"I couldn't have you going out with a loaded gun. We don't need any mis-fires, because one is in the chamber."

"Tracy, I love you."

She just smiles and sucked just the head in. She didn't move a muscle. She just looked me in the eyes and batted her eyelashes. I felt sweat forming on my upper lip. I couldn't look away from this girl that adored me. This may be the most erotic thing we had ever done and she wasn't doing a thing but holding tip of my cock in her mouth. I was completely surprised when I came. What the hell did she do? I felt like I had been mind-fucked. When I stopped filling her mouth with my seed, she released the head of my dick and I saw the pool of cum sitting on her tongue. When she was sure she had my attention, she swallowed my load. I just groaned.

"Damn that was intense. You haven't cum in a while have you? That was a huge amount even for you."

I helped her up and kissed her. All I could say was, "Thank you."

She spun me around and swatted my butt.

"Get in there and don't forget to shave."

I took care of my shower and shave. I came out of the bathroom nude and I saw Tracy on my bed watching me. I dutifully put on the clothes they had picked out. I put my belt on and I was putting my wallet in my back pocket when Tracy stopped me.

"Let me see that."

I hand her my wallet and she found the condom. She checked it to make sure it wasn't damaged. She then opened my nightstand, got out two more and put all three into the wallet and handed it back. Her meaning was clear. I was to use all three tonight or not come home. I would bet the farm that she would count how many I had left after my date.

I finished dressing and we headed to the house. Mom was driving us because the destination was a surprise. I was holding Tracy's hand as we crossed the drive to the back door. I caught a glimpse that she was sad. She had hidden it well up to that point. I stopped and she was pulled up short. As she turned to see why I had stopped, I kissed her. It was a gentle loving kiss intended to tell her that we were together. When we pulled apart, she smiled and I could see she was blinking back tears.

"Tracy we need to talk about our relationship. Before you freak out it isn't anything bad. I know we have expectations for each other. If we don't know what those expectations are, we will end up disappointing each other. I feel like tonight is disappointing you, and if it is I will not go through with it."

"The funny thing is I am not really worried about tonight. I know you both need to get physical to find out if there is more. I don't know why, but I know you will find out you make better friends than lovers. I know you think I'm nuts sometimes, but in the long run this is best for us. I want you to rock her world. Don't hold back. I don't want you coming home thinking you wished you had done something more."

I shook my head in disbelief, but she seemed sincere. One of my biggest issues with Tracy was trust. I know if we are going to succeed, I need to trust her again. I decide I would trust her. Not the, I trust you but I need to verify. I gave up my doubts, and truly trusted her.


When Beth opened the door, we both looked at each other open mouthed. Our Moms were not playing fair. Beth was dressed in a white dress that showed plenty of cleavage.

I looked her in the eye.

"You take my breath away."

I heard Mrs. A, who is obviously spying, burst out laughing, which got us both laughing too. I grabbed her hand and went to the car.

"You guys are not making this easy are you," I told my Mom.

She didn't say a word and drove us to the Henderson. It was a landmark hotel that had one of the best restaurants in our town. I helped Beth out of the car, and gave her my arm as we went inside. We went through the grand lobby, and found where we were going. The maître d' had our reservations, and we were seated quickly. Dinner was very enjoyable. Beth and I had been friends forever, so there were no awkward moments until dessert was almost finished.

"David, I ... I guess I'm not good at this," Beth said.

"What? You know you can tell me anything."

"I know, but I have never asked a guy to..." Beth blushed.

"Are you asking if we should continue our evening in private?"

"Yes," She said hesitantly. Then she finished in a rush, "I got us a room."

I paid our bill, and Beth handed me a keycard holder with 1111 written on it. We almost ran to the elevator. As we went up, we were in a lip lock and freely exploring each other's bodies. When we got to the 11th floor, we staggered to the room never breaking our kiss. We stumbled into the room and I pushed her up against the wall. I spread her legs and reach under the dress to cup her pussy. I found two things that made me very happy. She was not wearing any panties, and she had shaved her pussy bald. She was so hot her juices were literally running down her thighs.

I squeezed her cunt and she stiffened and came. If I weren't holding her, she would have collapsed. I picked her up as if she were a feather and laid her on the bed to recover. I lost my clothes so quickly that I might enter the Olympics if they ever had the undressing event. I put on a condom and when she came to her senses, she yelped and scrambled off the far side of the bed as I stalked her with my dick leading the way.

She slowly backed up and I had an evil grin on my face.

"David what are you doing. Let's talk about this."

The hotel room had floor to ceiling windows that overlook the downtown area. Beth made a move to dart around me, and I grabbed her around the waist. She struggled to get away so I grabbed both of her wrists and pulled them over her head and walked her back till she was pressed up against the window. I kissed her hard. She bit my lip and I tasted blood. I gave her a huge hickey in the side of her neck in retaliation. We were both now marked. I spun her around and spread her legs. In one fluid motion, I slotted my cock and buried it to the hilt in her personal volcano. Mount Beth erupted around the length of my shaft sending ripples of pleasure all along my rod. "FFFFUUCCKKKK!"

I let my hot breath caress her ear.

"If someone looks up they can see what you are doing."

"You Fucker!"

Oh my, sweet Beth had a potty mouth. I took that as a signal of her desire and started to pound her from behind. You could hear my crotch slap her tight ass with each stroke. 'Clap Clap Clap'. She went into hysterics. "OOOOHHH DAMMMMNNN ... FFFFUUUCKKKK ... Oh God, OH GOD, SHHHIIIIITTTT."

Her pussy caressed my shaft. I reach up and unzipped her dress and let it pool around her hips. I soon had her bra off and I found her hard nipples, pinched, and tugged on them. This sent her through the roof as she made a sexy groan signaling her approval. Her pussy gripped and released me several times. I felt it pumping girl juice all over my balls. It was finally too much for me as I unleashed my load. My release caused my shaft to twitch and jerk causing her orgasm to keep rolling into a new one. She sagged back into me as she collapsed for the second time in the last thirty minutes. I picked her up and gently put her on the bed. She rolled up into a fetal position.

I took care of the used condom and I saw to the mess all over my crotch area and down my legs. I smelled as if I had really a good time. There was a hot tub so I started to fill it. I stepped into the shower to get clean. When I got out the hot tub was full. I turned on the jets and set the temperature. A groggy Beth let me help her out of her dress. I picked her up and carried her to the hot tub and I stepped in and lowered her into it.

"Oh David, thank you, I needed this."

It was a small hot tub, so I let her lean back on my chest and let the bubble do their magic. I think we both dozed off because we both jerked awake when the bubbles stopped after 30 minutes. Beth got out of the hot tub and helped me out. We dried each other off. Mr. Happy was stretched out so she wouldn't miss a spot. She grabbed him and my body followed as she took me to bed.

She got me flat on my back and she climbed up and stretched out on my chest. She was positioned so she could look me in the eye.

"David you surprised me. I have had fantasies about someone just taking me like that. It was even better than I imagined." She got a sad look, "I know we are not going to be a couple, at least no time soon. But I am putting you on notice. We will be fucking. I have some other fantasies I want to do, and I never found a guy I trusted enough."

"I would love to, but I need to talk to Tracy," I said.

Tracy and I really needed to have a talk soon.

"She already knows about Cindy and Suzanne."

"How does she know about that?" I asked defensively.

She gave me a look that made me realize that my fuck buddy arrangement was not as secret as I thought it was.

"I want you to add me to the list. If you are smart, you will let her know about our arrangement. But if you decide to keep it a secret, I will go along with it."

I shook my head.

"No I've learned my lesson. It is better to be honest and blow up our relationship now than to do it later with a lie. Is Tracy somehow proud I'm with three of the hottest seniors at our school? Does this somehow help her with social status?"

That was something I could never quite figure out.

"You have no idea. She will be the Queen Bee for her Junior and Senior years. She is dating every girl's wet dream."

"I call bullshit on that one."

She gave me a smile when she found I was serious.

"You are the sweetest guy. Thank God you have no idea how you touch us. Just keep believing you are a regular guy, and you can have anyone you ever want. Don't become one of those ego-driven douche bags that think they are God's Gift." She got a strange look and said, "I would actually like to see you tear through the girls at our school. Poor Greg's legend would be an afterthought when you got done."

"Like that is going to happen. Tracy might tolerate some things, but sleeping with every cute girl in school would find me without my balls very quickly."

"Like that would be the only problem with that plan," She laughed. "If Tracy didn't get you, the male population would soon put a stop to it. No one would want to go after you had been with a girl. They would all be afraid they wouldn't be able to cut it. And the sad truth is they wouldn't."

She got sober for a moment.

"I think that is why Ed and Luke turned on you. No one wants to come to the realization that they don't measure up. I always thought Luke was a good guy. It really shocked many people, and you mister, I was so impressed you stayed above it all. I talked to his brother Mike, and Luke is very confused by how and why you saved his scholarship. Mike said he is embarrassed, and never knew you were such a good friend. Tracy called Luke, and let him know how you got him the scholarship in the first place. Can I ask? Are you ever going to forgive him for what he did?"

"Hell you know me. I took Tracy back didn't I? How I feel right now, probably not. Tracy has one huge advantage the Luke never will. She and I fit as a couple. Luke will never be that for me. I suspect after he graduates I will never see him again."

"You may not ever be friends, but I think you need to forgive him. You don't need to carry that burden around. Do it for yourself if you can't do it for him."

I kissed her for her advice. She always knew what was bothering me and how to fix it.

"Can we do one of my fantasies now?" I asked.

"Does it have anything to do with my ass?"

"Hmmm. I may be getting a new one, but not right now."

"Then tell me."

"I want to make love to you. I want to worship your perfect body and make it sing."

"I think I like this fantasy."

I grinned and flipped her over making her squeal in glee. I slowly started to work on finding all her erogenous zones. I found that almost everything turned Beth on. I was able to make her cum by just playing with her neck and ears. Her breasts caused her to cum even harder. By the time I had my face buried between her thighs, she was cumming almost continually. I put on a condom and I made love to her. We locked lips, and we let our passion take us over.

When I came, it set her off and she wrapped her arms and legs around me and wouldn't let go. She bit my shoulder and dug her fingernails into my back as we both shuddered into a post-orgasmic bliss. I rolled off her and went to the bathroom to dispose of the condom. I checked my back and shoulder and found that she had not broken the skin, but there were certainly red marks.

I brought Beth a warm wash cloth so she could clean herself up and I crawled into bed with her and we were both were asleep almost before our heads hit the pillow.


Thursday November 28, 2013 – Freshman Year

I woke with a jerk as I found Mr. Happy trying his best to work his way down Beth's throat. She grinned around my cock and let it slide out of her mouth.

"Good, you're up. Grab a condom I want a quick one before we have to leave."

I handed her the last condom and she rolled it on like an expert. She straddled my waist and slowly sank down. She got it about half way in on the first try. Beth kept working at it until she was sitting on my crotch.

"God that feels good."

I had to agree. She sets a slow steady pace. I was stroking her just under her breasts where I had found one of her more intense erogenous zones. I suddenly found myself cumming. I could tell she didn't get there yet so I rolled her off and inserted two fingers into her aroused vagina. I quickly located her G-spot and started massaging. "OH GOD!"

It works every time. Another satisfied customer served. I needed to get a sign like McDonalds. Beth had been such a good girl that I continue to massage her G-spot as I latched onto her clit and started tapping it with my tongue. I swear to God she tried to tear my hair out to get me to stop. Suddenly it was as if I hooked her up to an electrical outlet. She went stiff, arched her back, and just froze. She finally collapsed taking huge breaths of air as she began to breathe again.

When her eyes cleared, and she was breathing normally again, she said.

"Let me give you a tip. Sometimes a girl just wants a nice cum, you don't have to see if you can make them pass out each time. That said, I'm not complaining."

I called Mom and told her we needed a ride home. Twenty minutes later Mrs. A and my Mom were at the door. They told me to go to the car. Was I six years old again? I knew better than to argue so I went down to the car.

Of course, it was locked. I took several deep breaths and calmed down. Nearly 30 minutes later, Beth came out wearing jeans and a t-shirt and looked freshly showered. I was leaning back against the car patiently waiting. No one thought it was a problem that the temperature was dropping and it was starting to snow. I was wearing a light t-shirt and no coat.

Mom dropped Beth and Mrs. A off and then took me home. She told me to come over to the Andersons when I was cleaned up. They were hosting this year's Thanksgiving dinner.


A long hot shower caused me to get drowsy so I stretched out for just a second. I fell asleep and the next thing I heard was my phone going off. Tami sent me a text wanting to know when I was going to the Andersons. I looked at the clock and it showed it was noon. I sent her a text to tell her that I would be there in about 30 minutes. I looked outside, there was at least four inches of snow on the ground, and the wind was picking up.

I put on my Kentucky sweatshirt and jeans. I grabbed my new leather coat and headed over to Beth's house. I about killed myself coming out the back door of my apartment. A thin layer of ice was under everything. Beth's house was four blocks away. The wind was picking up the snow and making it almost impossible to see. By the time I got to the Anderson house, I was wet and miserable. I came in the back door where the mudroom was so I could leave my boots and dripping coat. I grabbed a hand towel and dried my coat and hair.

I was about to come out of the coat room, but I saw Tami with a guy. Something made me stop and take notice. She was leaning towards him and touching his elbow. All signs of a girl interested in a guy. Her eyes were also watching everything he did. On Sunday she was warning me she had met someone. I suddenly couldn't breathe and my stomach was threating to do something horrible.

When I felt saliva start to pool in my mouth I stepped back outside and dry heaved over the railing. Luckily, I hadn't eaten since last night. I had always known that when Tami started dating it would be hard for me. I needed to lie down. I stepped back in the house and just slid down the back door. Tami sent me another text wanting to know where I was. I sent a text back wanting to know when she planned to tell me about her new boyfriend. She sent back a smiley face.

I put on my boots and coat and whipped my phone into the kitchen. It hit a wall and exploded about the same time I walked out the back door, and slammed the door. I walked the ten blocks to get to a diner that was open. I ordered a bowl of soup because I couldn't hold anything else down right now. After eating, I didn't feel quite so shaky. I called Kendal using the diner payphone, and she answered on the first ring.

"David, where are you? My phone has been ringing off the hook."

"Kendal, I don't want to be found right now. Can you come get me and put me up in a hotel?"

"No. You are a minor and I can't help you run away."

"Okay, I understand. Let everyone know you talked to me. I will see you tomorrow."

"Where should I pick you up?"

"I'll call you in the morning and let you know."

I wasn't thinking clearly. I really wanted a drink. Everyone knew Tami had brought a guy to Thanksgiving, and no one let me know. If I wanted a straight answer, I could get it from Angie. She was the only one I could think of that wouldn't betray me. I called her.

"If you say my name I will hang up."

"Okay."

"Go somewhere where we can talk."

She went to the bathroom.

"Tell me."

"Tami brought Bryan home because he didn't have anywhere to go for Thanksgiving. They are not officially dating but it is obvious she is interested. She is a mess. Can I get her, and you talk to her?"

"Yeah, let's get this over with."

Tami came on the line.

"Damn you! I wanted you to meet him before I went out with him."

"Tami, how would I react to a surprise like this?"

"Not well," she mumbled.

"Then why did you not prepare me for this?"

"You were already mad at me. I thought this would be the best way."

"How long do I stay mad?"

"The longest was about a day," she laughed.

"Well, this is different. I was physically ill when I saw the way you looked at him. I feel like I'm having a panic attack. I haven't felt this way since this summer. Tami, I just can't do this right now. I'll call you." I said as I hung up.

I walked home to my apartment. I didn't turn on any lights. I took a hot shower, crawled in bed, and collapsed ... I woke to find my Mom and Dad glaring at me.

"David Allen Dawson, what is wrong with you?" my Mom asked.

The fog in my brain cleared enough to realize what a little shit I had been. Once again I was showing my immaturity by only thinking of myself. Thanksgiving was a family event and I had bailed on everyone.

"I'm sorry, I wasn't thinking. Tami's new boyfriend caught me by surprise."

"I want you to answer me something," my Dad told me. "Why is it okay for you to date and not Tami? Do you think it is any easier on her to see you dating Tracy? That girl loves you to death, and you can't find it in your heart to allow her to find the same joy you are experiencing. I thought we raised you better than that."

I looked at my Dad in shock. He was right, I was being a hypocrite.

"David, we love you," my Dad said. "But sometimes you infuriate us. I know it has been a while since you pulled a stunt like this. But we can't have you acting like this and giving you adult privileges. We are going to give you a pass on this one. The next time you pull something like this you will be losing the apartment. Are we clear?"

"Yes sir."

My Mom has stayed quiet, letting my Dad handle this. He only stepped in when you had done something really bad. I could see both the caring and disappointment in their eyes. I never wanted to disappoint them. That was the worst punishment I could receive. They got up and left me to think about what I had done.


Friday November 29, 2013 – Freshman Year

When I woke, Tracy was lying on the bed with me. She smiled at me.

"Good morning sleepy head. I was about to wake you because you have to get to your photo shoot. Kendal will be here in thirty minutes. Go take a shower."

When I came out, she had what I was to wear laid out. I just put it on. Sleep was what I needed. Tami, of all people, should know I don't take surprises well. When I was twelve, my parents threw a surprise birthday party for me. I ran away for a couple of hours before I came back. If she had told me Sunday, I would have been fine. Well not fine, but I would have sucked it up for her. I really would have been happy for her.

I took Tracy's phone and called Tami.

"Hey, I'm sorry for yesterday."

"I know you are. I'm sorry too. I should have told you. I still want you to meet him."

"Can I call you when I get done today?"

"Yes, maybe you and Tracy can go to dinner with us."

"I'm sure that would be okay. I have to go."

"Okay David, please focus and do well today. Janet said her dad is excited. This could be steady money for you. Don't let yesterday ruin anything."

"Tracy and Kendal will smack me around and get my game face on. Talk to you later." I turned to Tracy. "Thanks. I need to get to a phone store and get a new one."

"Kendal is taking care of that. Now tell me, when was the last time you ate?"

"I had a bowl of soup yesterday and before that dinner with Beth on Wednesday."

"There is supposed to be breakfast at the shoot. I have a bag of grapes to hold you until then."

I finished getting dressed and I saw Kendal had pulled up. Tracy got me to the car and kissed me good luck. I had hoped she was going with me. I waved as we pulled away. I think I said three words to Kendal on the ride to the shoot. I was still pissed that she wouldn't help me yesterday. I knew that what I wanted was childish, but at the time, that was what I wanted. We were early, so I found Mr. Hill to let him know I was ready. The photographer and wardrobe were not there yet. I went to the break room to find what they considered breakfast was a yogurt and mixed fruit. I found a vending machine and bought a candy bar. It was going to be a long morning without some real food.

I went to makeup to get started. She explained the first shoot was for coats so I would only need to do my hair and face. We were done after a quick touchup. I found Mr. Hill and asked if he wanted to do a test shot, to make sure the makeup was right. He had one of his assistants take the shot, and put it up on the monitor. Mr. Hill and the makeup girl made some adjustments and I was ready. The wardrobe came and I changed for the first set of shots. We didn't have a photographer though.

After we waited an hour and no one could track the lady down, I suggest that Mr. Hill's assistant take the shots. We had a storyboard of what was needed. After each section, they would download the shots to the client and get them approved.

Mr. Hill's assistant was trying to break into the business, so it wasn't as if he was a complete amateur. We took the first set, and sent them off. The client had us reshoot a couple and we were on to the next coat. Two hours later and we were done.

While we were finishing up the second photographer and wardrobe arrived. This was sweaters and jeans. We were three quarters of the way through the second shoot when the first photographer arrived. Mr. Hill told her that we went ahead and did the shoot without her. She demanded that we redo the shoot. She wanted to talk to me.

"You, boy, who told you to do the shoot without me," she demanded.

"Lady, I'm busy. Have some respect and let us finish this."

The other photographer smirked at her, and she knew she was about to cross a line. She stormed out and let us finish. Mr. Hill came to me.

"I know this is unusual, but would you be willing to redo the first shoot?"

"I will if you feed me first. Actually, get some pizzas for everyone and I will get started with the photographer. If she is not ready, we could get Kendal in here, and go over the last shoot so we can sign the release."

Of course, she needed to move all the lights. Kendal was very professional and we went through all the photos. There were a half dozen that were not good. Things like my eyes were closed or I had a dorky look on my face. We signed off on the rest, and Mr. Hill paid Kendal for that shoot."

Pizzas came and everyone took a break. Everyone watched in amazement as I ate a large pizza by myself. I just gave them a look.

"Guys, have you never seen a teenage boy eat?"

I went and put on my first coat on again and met the photographer. Her name was Kim and when I didn't give her any attitude, she lost the bitch persona. She took a couple of test shots and adjusted the lighting. When we got started, she knew exactly what she wanted. I listened carefully, and we worked well together.

Kim, Kendal and Mr. Hill went through each set of photos when we were done. To her credit, Kim pointed out a couple by Mr. Hill's assistant that she said were better, but overall she had a much better eye. There were no shadows in her pictures. Mr. Hill could have gotten away with just using the first set, but he was happy we took the time for the second.

He and I sat down after the shoot.

"Kim only had good things to say about you. She was impressed you kicked her out of your shoot. Then, you were professional during her shoot. Kim has a lot of pull with several of our clients. I just wanted you to know she is a big fan and so am I. I know this is short notice, but we would like to have you come back tomorrow and do two more shoots."

"I have a problem. My best friend is back from Wesleyan, and the only time I have seen her for quite a while, was Sunday at the mixer. She has a new boyfriend I haven't met, and my girlfriend is new, so I need to make time for her. On Sunday, I'm off to Chicago to meet my new agent. So if you don't mind me bringing three extra people, I can do it."

He laughed shaking his head.

"I thought you were going to turn me down. Of course you can bring them."

"As long as you are in a giving mood, could you have some real food here? Either that or I need to be able to leave to eat."

"I forgot you are an athlete. Most of the models we have in here eat like birds. We have a grill on the back patio. How about I bring in Janet and my wife and we do a cookout of hamburgers and hotdogs?"

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