Stupid Boy - Cover

Stupid Boy

Copyright© 2014 by G Younger

Chapter 26: Amelia Island Shoot

Coming of Age Sex Story: Chapter 26: Amelia Island Shoot - 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 December 23, 2013 – Freshman Year

First thing in the morning, I found myself back at the gym. Eve and I made arrangements for her to pick me up and I teach her how to use the equipment. With her singing career, her ex-agent had suggested that she get in shape. It wasn't that Eve was overweight, she was like many teens, and she needed to firm up if she wanted to be in the public eye.

She wore a pair of tights and a loose t-shirt. Eve had always been a tomboy when we were growing up. She was 5'8" with silky dark brown hair that hung to the middle of her back. Up top, she was a nice 'C' cup. Her best feature was her butt. She had a runner's butt (round and firm) and muscular thighs. Her wearing tights caused my shorts to tighten. She saw me staring and she winked at me.

"I see you haven't changed."

"What?" I said defensively.

"You always check my butt out," she said as she gave it an extra wiggle. I groaned and rolled my eyes. She came up and kissed my cheek. "I never said I minded."

Ken, one of the personal trainers, saw me, and came over. Ford had set me up to work with a trainer. I had met with the three main trainers when I signed up. One of them was usually on duty. The plan was that they would all know what I was working on so one of them would be there if I needed help.

"Hey David, glad to see you are finally taking advantage of the facilities. We were worried you would start getting fat," Ken said.

His comments got a chuckle out of Eve. He turned to her.

"I take it you are David's girlfriend."

"Yes, yes I am!" Eve exclaimed, daring me to dispute it.

"Nice to meet you, I'm Ken. If there is anything we can do for you please let us know."

"Actually I'm taking off to do a photo shoot and go skiing with my church, so I won't be back till the first of the year. I'm helping Eve get all her extra weight off so we can be seen together in public," I said as Ken and I looked her over.

I could tell there was going to be hell to pay by the glint in her eyes.

"Can you possibly help her with all her problem areas?"

How I said that without laughing I don't know. Eve and I both looked at Ken for his response. He looked like a deer facing down a semi.

"Ahhh, yeah, that shouldn't be a problem," Ken muttered.

I lifted up her shirt, pinched her waist, and shook my head.

"I mean we can't have her in anything too revealing right now," I complained.

Her eyes were getting bigger. I grabbed her waist, turned her around, and ran my hand over her ass.

"And this ... I mean it is fun and all, but do you have some ideas?"

Ken went bright red and stammered, "Let me get a clip board and take some notes."

When he was out of earshot, Eve turned on me.

"What the hell was that?"

I took my offending hand off her butt and smirked.

"I was just helping my girlfriend," I said in mock sincerity.

She grabbed my hand and put it back on her butt.

"Do you really think my butt is too big?"

I took the opportunity to explore my newest fascination. I pulled her into me so she could feel what I thought of her ass and smirked.

"What does that tell you?"

It was her turn to groan.

"Dawson, if you didn't have such a nice girlfriend, you would have more than your hands full."

Ken came back and I let him show her how to use the machines. I went and ran on the treadmill, did my sit ups and pushups, and then met Eve in the pool and we swam our laps. We finished up and headed to Tom's office so Eve could sign her contract.


When we got to Tom's floor, I split off and found Kendal. She was happy to see me.

"Hey rock star. I hear you are adding a new client to the wall."

In the lobby, they had pictures of all the 'talent'. So far, everyone on the wall was due to me steering him or her to Tom and Kendal. When I came in, I saw they had Ford's logo on the wall and under it said 'partner'.

"Eve is a childhood friend. She made a go of Nashville but it sounds like things didn't work out. I think she just needs a break and she will be big. Think Taylor, but someone that can sing."

Kendal just rolled her eyes at me.

"I need to talk to you about your financials," she said getting serious. "Your Mom's doctors are suggesting she go to a specialty center for cancer. The one they are suggesting is Stanford Cancer Center. They have made great strides in the type of cancer your Mom has."

This was the first I had heard of this. If they felt it was necessary, I was willing to spend the money. Tom had set up a line of credit for me to help my Mom out. Dad had tried to get insurance on the government web site. After trying like thirty times, he finally got it to work. The insurance offered was expensive and didn't cover what we needed. They didn't offer any flexibility in doctors or hospitals. There was no way they would ever cover a specialty cancer center. We had made a family decision that we would have to self-insure her. It would give Mom the best chance to survive. I felt sorry for other people in our predicament.

"How much is this going to cost?" I asked.

"I don't know, but it isn't going to be cheap. The good news is you are starting to earn some income from the other talent you found and the Red commercials. You will also make a nice amount doing the Florida shoot," Kendal commented as she looked at her financial reports. "We need to decide how much you want to keep in your personal and business accounts before you dip into your credit line."

"What do you suggest?"

"You need enough to pay taxes and have spending money. I would say you need to have at least $40,000 in your business account to cover your taxes and $5,000 in your personal account."

"Kendal, you know better than I do. Go ahead and set it up. Is there anything else you needed?"

She pulled out a folder with some pictures of my Range Sports shoot.

"Kennedy Images wants to buy the rights to these pictures so they can sell them on their websites. They are offering two deals. One is $5,000 per image or 30% of their sales of each image." She pulled out the one with me chasing the wolves. "Tom and I talked and he suggested that you take the $5,000 now on all the images except this one. He thinks you need to hang onto the rights to it."

I counted the pictures and they were twelve. Kennedy Images was a major source of pictures for advertisers and websites. I was sure that over time, I could make more with the 30% deal, but I needed funds now for Mom's cancer treatment.

"Okay that sounds good."

I had noticed, as I walked back to Kendal's office, that several of my photos from various shoots were on the walls. There was also a couple from the other models. I had a sneaking suspicion these were pirated copies.

"I have a question." Kendal looked up and saw that I was up to something.

"What is it David?"

"I saw my butt hanging in the conference room and several other photos. Did you pay for those?" I could tell from Kendal blushing that she had been caught.

"Ummm ... I would have to look into that," Kendal bluffed.

"You have my financial reports right there."

"Okay, I forgot to ask if we could use the pictures to decorate the office. The partners thought it would help market the talent. I didn't think you would mind."

"Tell you what. You know the main wall in my apartment," I said to Kendal as she nodded in recognition. "If you set up a gallery of my work while I'm gone the next few weeks, you can use any of my photos you want in the office."

I saw her flinch because I knew she was taking pictures home and I was sure she was giving some to her coworkers. I gave her a stern look.

"Kendal fess up. Have you been giving my work product away? You realize this is how I make a living, right?"

She looked ashen when she realized what I was saying. She had access to the original files and some of the better shots were being sold in a high-end gallery and also by a decorator for as much as $5,000. Some of the lesser shots were selling in the $250 range. Exclusivity made up a serious portion of the value. It was one thing to be using the photos in the office. It was another to be giving them away to the staff.

"David, could you excuse me for a minute," Kendal asked as she bolted from her office.

As I waited, I was starting to get pissed. I was taking a reduced fee for my shoots to garner the resale rights on my photos. After waiting a long ten minutes, I had enough and came out of Kendal's office. I found Eve in the conference room alone.

"Hey, where is everyone?"

"It seems that you have stirred something up. They are in a little bit of a panic." She looked at my photo. "Nice butt."

"I'm glad you like it," I chuckled. "I'm just getting used to it being on display. Do you know where they went?"

She pointed to Tom's office. I was greeted by his secretary.

"Hey David, they just asked me to track you down. You can go in."

I walked in to find five other men and Kendal. The suits I assumed were lawyers at the firm. Tom's face was red and looked like he had been dressing down the group before I came in.

"David, first of all I want to apologize personally and for my firm losing control of your photos," Tom said.

"How bad is it?" I asked.

Tom handed me a list and at the bottom and estimated value. It was in the six-figure range. My head snapped up and looked Tom in the eye.

"Everybody out, David and I need to talk," Tom ordered.

I could tell that Kendal had been crying but right now, I didn't want to deal with that.

When the door closed Tom started, "I think of you as a son. What Kendal did was huge mistake. I haven't decided if I am going to terminate her or not, but she wasn't the only one. All I can say is I am sorry. I have ordered all, and I mean all, prints brought back to the office."

Tom and I both knew that his staff and their friends could not afford to pay me for the prints taken. I was in a tough spot, and he had played the family card. We both knew that I was getting a hell of a rate on the fees they were charging me. I was also critical to the division's future. A prime example was sitting in their conference room as we spoke.

"Tom if this gets out, it will kill your business, but you are right; we are family. Here is my concern. I don't need to see these pictures on EBay. The ones that went to employees I'm okay with as long as you can get assurances in place that they can't gift or sell the prints. Were any given to people other than employees?"

He went through the list and found five that went to clients as holiday gifts.

"What do you want to do about these?" I asked.

"I guess I'm going to have to write you a check," Tom said not looking too happy.

I knew with any startup, cash flow was tight. Tom was staking his reputation at the firm by starting their new entertainment division. He and the partners would have to pony up the funds.

"No you're not," I said as he looked up with hope in his eyes. "I need write offs for taxes."

"David, I really appreciate you doing that. I assume you don't want to me to fire anyone either."

"You assume right, my friend. I trust you will get control over this and I think people have learned their lesson. My main concern is hurting Mrs. Hill and Mrs. Wesleyan's businesses," I reminded him.

"I think we need to get out front on this. I'll call them both today and let them know what happened," Tom offered.

"Please do. Work it out. If I have to give them back some money or give them first looks on pictures, do it. They took a chance, and we have a good thing going now."

Tom just nodded.

"Do me a favor and keep me in the loop on Eve," I said, changing the subject. "If there is anything I can do to help her call me."

We shook hands and he went back to finish up with Eve and I went to find Kendal. She was sitting in her office with the other lawyers. I walked in and smiled. That was all Kendal needed to jump up and hug me.

"I didn't even think. It won't happen again," Kendal promised.

"I know it won't. We just need to think of Mrs. Hill and Mrs. Wesleyan's business. They pay us good money to sell those prints. I assume you are picking up Tracy and me for our trip to Florida."

"I will meet you at Tracy's for the party and we will leave at 5:00 to make our flight. I'll see you in a little bit. I need to make amends with Tom before I leave," Kendal told me.

I went out to the lobby and found Eve smiling.

"Congratulations on getting new management," I said as I hugged and kissed her on the cheek.

"Mom and Dad will be in later to sign to make it official, but we are good to go. Thank you for helping. Now Tracy said I was supposed to take you to lunch and then we are to go to the party at her house. I'm buying, and just got back, so we are going to Monical's."

Hey, it's not just me. Their pizza is addicting. I just smiled and went along for the ride.


Eve got me to the Dole's home in time for everyone to open their Christmas gifts. When I saw what I gave everyone it reminded me I needed to take my debit card back from Tracy. I even paid for airline tickets so my grandparents could come and stay through the holiday season. That and having Angie's family come, excluding her Mom and Dad, were the best gifts I gave.

Selfishly, I was most excited about what Devin and Sandy Range sent me. They sent a snowboard, snowboard carrier (for the plane) and complete ski outfit. They also sent me a company credit card with instructions to buy a wardrobe from any of their company stores. They wanted me to be seen in their clothes on a daily basis. Kendal had filled them in on my Florida trip so they were having clothes delivered to my hotel.

Mary outdid herself. Her gift to me was cooking lessons. I looked forward to spending time with her and really learning how to cook. I could get by, but Mary had learned from her Dad who was a master chef.

Tom and I took Mom and Dad into his office and we told them about getting her into Stanford Cancer Center. I could tell by her reaction that everyone was keeping how bad this cancer was from me. She broke down in Dad's arms. I basically lost it when I saw my parents' reaction. Tom held me while my parents recovered from the news. Then Mom and Dad came over and hugged me as we all cried. Tom's office opens up to the pool area so I snuck out to get some air while Mom told everyone at the party.

Shortly after Kendal showed up and the three of us headed to the airport.


We arrived at the Ritz-Carlton on Amelia Island just before midnight. Kendal was staying with Kara and Tracy and I had a suite. We were loaded down because we were going straight to the ski resort from the photo shoot. We had both winter and summer clothes with us.

Tracy was like a kid in a candy store when we finally made it to our room.

"David, come look at this. There are boxes from Range Sports. One is addressed to you and the other to me."

"Open it," I said.

She grabbed a letter opener and opened her box. It had several sporting outfits from swimsuits and pullovers to a ski suit. She opened mine to find board shorts and t-shirts plus an assortment of casual wear.

There was also an envelope from the photographer for the diamond photo shoot. Inside was a rider to my contract for confidentiality as to who the client was. The note said that TMZ and Entertainment Tonight had been stalking the hotel trying to figure out what Kara was doing and whom she was meeting. I called Kendal and she stopped by our room and read the rider. I called Kara and talked to her about her feelings and she said it was no big deal. She had signed off on it so I followed her lead and did too. Before she got off the phone, we made arrangements to run in the morning.

Tracy was treating this trip like a honeymoon, so I was not getting to sleep until we made love at least once. She finally left me alone when I explained what time I needed to get up at to exercise. She actually threatened me if I woke her up then I might not make it to Christmas day.


Tuesday December 24, 2013 – Freshman Year

Kara met me in the lobby at six in the morning. She wanted to go run on the beach. When we got the sand, she stopped me before we went any further.

"I don't know how used to media you are. I would suggest you get a publicist. Part of the game is they try to catch me with a guy. I'm going to ask you for a huge favor. I need you to be my boyfriend."

"Okay, explain this to me," I inquired.

Why were girls always talking me into things?

"It helps keep unwanted advances and it will help both our careers. My publicist has TMZ waiting on us at the beach. They will lead with this tonight in exchange for an exclusive."

I looked at her and sighed. I would need to do some damage control, but Kara was a friend.

"Okay, I will help as long as I get a real workout this morning."

"Okay lover, I can arrange that," Kara flirted.

I shook my head. The assumption was that Kara, Tracy and I would end up in the sack. The two of them had been plotting this. Tracy thought Kara was hot and since she let me out to play, how was I going to say no.

"You are so bad. Tracy will claw your eyes out if she can't be there with us."

"I wouldn't have it any other way for the first time, but hear me lover, you and I are going to have some alone time this week," she purred as she swatted my butt.

We jogged north towards the nearest small town. I quickly found running in sand is tiring. We made it a half mile up the beach when we were stopped by TMZ.

"KARA, KARA! Who are you with?"

A guy in his early twenties and a cameraman were setup on the beach. We were both sweating so she requested a towel before we answered any questions. The reporter must have figured what was coming because he had a duffel bag with towels and bottled water waiting for us. We dried off, got drinks and then posed for the camera.

The reporter repeated his question.

"This is David Dawson my boyfriend. He is with me shooting a commercial..."

The interview went on for ten minutes. I was glad I put on my Range Sports garb because they were about to get some free national advertising. When we were done, they staged us running on the beach.

Kara and I didn't make it back to the hotel until seven and Entertainment Tonight caught us coming in from our run. We brushed past them and went into the hotel. When I got back to my room Kendal and Tracy were eating breakfast. They had ordered for me so I took a shower and came out and joined them. I figured I had better come clean with the whole Kara is my girlfriend for the week. Tracy was patient with me, but it would not be fair to her to have her find out from someone else.

"Okay, Kara has more than a photo-shoot on her mind," I said getting both women's attention. Tracy just smirked. "We are now going out, sorry babe, I had to break up with you for a few days," I announced, trying to be funny. "She announced it to TMZ this morning and it will be on national TV tonight."

Tracy, God love her, just laughed.

"I swear David, if I didn't love you, I would have to kill you."

"I know, but she has been having problems with people hitting on her. She needs a public boyfriend to ward them off," I said. I thought for a moment. "We better start calling people and explaining before everyone sees it tonight. Kendal, please call all the people I work for and let them know. Tracy you call friends and family and tell them. Probably the quickest is to call Tami and let her handle it. She would enjoy having some scoop to share with everyone."

"We will need to make sure you are on Kara's arm while we are here. Kendal and I will hang back so the press doesn't get confused," Tracy announced as if it was the most logical thing in the world.

"You know David this is good for you. I talked to Clare at Ford and they suggested you start having a public girlfriend. She said a lot of up and coming entertainers do it for the very reason Kara is. It keeps the stalkers away. She also told me that it will boost your fees if you become a household name," Kendal told us.

"I'm game as long as you clear it with the boss first," I said as I leaned in and kissed Tracy.


Can I just say that the first day of the diamond commercial was one of the worst experiences I have ever had? The director seemed to be a major sexual predator, specifically he was stalking me! I had to keep Kendal, Kara or Tracy near me at all times, or I was fighting him off. When Kara said some nudity, I think she meant for herself. For me it was nudity all the time.

The only good news was that one of the photographers was Kim from the Hill Advertising shoot. I was glad to see a friendly face.

My day started off in makeup when they saw my pasty-white Midwestern body. What were they expecting in December? Their solution was I needed a spray tan. I thought the girls were going to pee themselves when I came out looking like an Oompa Loompa after the first round of makeup. All I needed was white eyebrows and a wig and I could sign up. Thank God, they could wash it off. I never want to look that orange again.

Once they got the color right, they had me put on a black speedo and go out for test shots. The director's name was Rafael. Kara came out in a black bikini. When our first shots came up on the screen, we looked good together. Rafael was reviewing Kim's work.

"Kara, David, I think this looks fabulous. David, I need you to lose the suit so we can make sure your skin tones work."

I was getting to the point that stripping in front of a crowd was not a problem. There must have been twenty people on the set. I just dropped my suit and Kara and I did a couple of test shots. She was smirking when she saw that Mr. Happy was being a little bit of an exhibitionist and rising to the occasion. Rafael ran out on stage and grabbed my unit.

I froze like a deer staring down the lights on a school bus. Kara was trying not to laugh as this freak held my manhood.

"Makeup! Makeup!" Rafael shouted getting everyone on the sets attention that he was holding me.

I was in such shock that I let him. The makeup girl came running out.

"You need to shave him. I am looking for a clean young look and this mass of hair just will not do."

I broke free and ran to makeup and Mr. Happy went limp in horror. Kara came sashaying her pretty ass back into makeup with a big smirk. I put two and two together and remembered she had full control on this gig. She picked the director who had just fondled me. When I turned on her, I saw her eyebrows go up and I just sighed.

"Kara, that was not a nice thing you did to me. At the very least you could have warned me," I said trying to stay calm.

It wasn't working. I felt violated and betrayed that my supposed friend would allow that to happen. Kara saw I was mad and apologized.

I could see her side of it. She was constantly being hit on by people on photo shoots. It only made sense she would pick someone who would not be interested in her.

I asked, "Just tell me he is good. Because I'm not putting up with several days of this if the final product isn't worth the hassle."

"Sorry I didn't warn you, but I have never seen him get hands on before. This will be worth it. He has won a lot of awards for his work and every time I have worked with him it has turned out fantastic."

The makeup girl was ready for me so I went and got an allover shave. Tracy and Kendal choose that moment to come and find me.

"Wow that is sexy. I can't wait to try it out," Tracy volunteered. Kendal just nodded not trusting herself to comment.

Rafael had me nude the rest of the day. The production company blocked off a section of the beach where they set up a cabana with everything in white. Basically it was an open platform with a king size bed in the center. There were plenty of white silk looking curtains blowing in the breeze.

Today's commercial had me walking out of the surf with water glistening off my body. I walked up to the staged bedroom to find Kara waiting on me with a Champagne glass. We had several little scenes flirting. Every time I got aroused, Rafael would stop and flirt with me. The effect was my arousal fled me. Towards the end of the day, I figured out what he was doing.

The end shot looked like Kara and I had just finished having mad passionate sex, and I reached under the pillow and pulled out a jewelry box. We did this scene twenty times, with her opening a different piece of jewelry.

When Rafael finally stopped for the day, I was exhausted. At that very moment, I could have used a beer. Rafael was all smiles.

"Kara you were spectacular as always. David, Kara made an excellent choice. The camera loves you two. I sent some of the raw footage to the client and they love it. If you want, come in at eight tomorrow morning and I will show you a rough cut of today's commercial and photos."

Kara and I agreed to come in early. I went and washed off the spray-on tan and changed into my Range Sports gear. We gathered everyone up and headed back to the Ritz-Carlton.


After the days shoot, we came back to the hotel to relax before dinner. The Ritz-Carlton is shaped like a big 'U' with the two long ends pointed toward the ocean giving each room a view. In the cup of the 'U' is a patio with tables overlooking a large sunken grass courtyard, which can be used for open-air events. Currently using the courtyard was a college football team who was in town for a Christmas Day Bowl Game in Jacksonville.

Things were going well until a few of the players saw the women I was with; Kara was a budding super model, Tracy was drop dead gorgeous and Kendal was hot by anyone's standard. I was pretty sure that all of them were out of my league, so when three of the football players came up to hit on them, I think they saw a kid. What they didn't know was I had a long day and was in no mood.

"Hey ladies, you're in luck that real men showed up to show you a good time. Why don't you come back to our room and we have a little fun," said jock number one.

I had to say, that was about the dumbest come on line I had ever heard. What girl in her right mind would fall for that?

Before my three ladies could say anything, I jumped in. I know they could take care of themselves. I had seen them do it many times. They had even put me in my place a number of times, and the smart move would have been to allow them to take care of it, but I was looking for a confrontation.

I laughed.

"Are you kidding me? Don't you see that the ladies are with me?"

"Listen little man, it is obvious you are not man enough to handle these three. We are doing you a favor by offering to satisfy them," said jock number two.

Again... ? Seriously? Best result was going to be you get a kick in the nuts.

Kara was ready to come out of her seat, but Tracy touched her arm and gave her head a little shake. She knew I could handle this. Out of the corner of my eye, I saw TMZ and Entertainment Tonight capturing this. I wanted to knock these guys into next week but I knew that would not play well on national TV. I could see it now, 'crazed boyfriend of super model... '

"Now you did it. You called my manhood into question. I think we need to have a little contest of skills to see who the better man is. Since going back and proving who has the biggest swinging dick wouldn't be fair to you, stubby, why don't we see who the better quarterback is?"

"How are we going to determine that?" asked jock number three.

Okay, I play football. These guys gave us 'dumb jocks' a bad name.

"I'm a fifteen-year-old freshmen quarterback from a small Midwestern town. You bring out whoever you want and we will throw fifteen footballs and see who the best is," I offered as they got smirks on their faces. "We can setup three trash cans and whoever can put more balls in the cans wins."

"What are the stakes, tough guy?" asked jock number two.

"If you win, you get a date with these women," I said and all three nodded their assent. "If you can talk them out of their panties so be it. If I win, you set me up with three of your cheerleaders."

"You are so on. Your smart mouth just wrote a check your little butt can't pay," said jock number one.

They led the way down to where the team was eating. Kara, Tracy and Kendal followed me along with the film crews. I chuckled when I recognized the recruiting coordinator, Tyler Seng; he sent me stuff and attended three of my games. Tracy also recognized him since she handled this stuff for me. She pointed him out confirming who I thought he was. The jocks explained the bet to their coach and he thought it sounded like a team building exercise.

Before I go any further, the staff at the Ritz-Carlton is the best in the world. If you have never been, you need to. They will pamper you like nowhere else. When they heard what we wanted to do, they did not hesitate in setting it up.

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