Stupid Boy - Cover

Stupid Boy

Copyright© 2014 by G Younger

Chapter 21: Chicago

Coming of Age Sex Story: Chapter 21: Chicago - 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 December 1, 2013 – Freshman Year

Kendal picked me up early because we had a long drive to Chicago. I loaded my bags in her trunk and I had coffee plus cinnamon rolls for the trip.

"Did Tom give you your portfolio?" she asked.

"Nope, I guess we have to go to your office first."

I thought for a moment of what else we might need. "Should we make a CD with all the photos watermarked?"

"That's a good idea. Do you have the CDs from yesterday?"

I shook my head no. I got my phone out and called Tom. He met us at his door and gave us the CDs and the release forms. We got to the office, and thirty minutes later, we were on the road.

The car ride was good for Kendal and me. We talked non-stop while learning about each other. She also explained what her new job was going to be and how happy her firm was with how things were going. Tom was going to adjust his business plan because the early success was not anticipated.

The partners wanted to hire someone with experience. Of course, that set off Kendal's insecurities. I think if she hadn't been driving, she might have slugged me when I started laughing.

"Kendal, settle down, so what if they bring someone in? It actually might be good because you could have a mentor, but you have to stop worrying about your job. I know I do all the work around here, but they still keep you."

"You do know that you have to sleep at some point. You don't want me pissed off. Call my brothers and ask them if you don't believe me."

"I think I'm calling bullshit; give me one of your brothers' numbers."

She gave me Dave's number and I dialed it. I heard a muffled hello.

"Dave?" I asked.

The guy sounded hung over.

"Yeah, who is this?"

"This is David Dawson. Your sister is my manager."

He perked up.

"Yes, the 'boy wonder'." He chuckled, "You know our little sister has a crush on you. You better be careful around her."

"Nice, I'll tell her you said that."

"Dude! She will kill me."

"Speaking of which, your sweet sister told me not to piss her off because I had to sleep at some point. What did she mean?"

Dave broke out laughing.

"Dude, don't piss her off. Jeff tore off all her Barbie doll heads and she flipped out; she was like 10 at the time, and Jeff is six years older, so he wasn't scared. That was when she made the threat that he had to sleep. We all thought it was cute until Jeff woke up to find his balls super glued to his thigh. It was classic watching Jeff have to tell Mom what was wrong. They had to go to the emergency room to set his family jewels free."

"No way!"

I looked at Kendal with a newfound respect.

"Way, Dude. Hey can I talk to her?"

"Sure."

I handed her the phone. They talked for twenty minutes and caught up. By then, we were starting to hit traffic coming into Chicago, so she hung up.

I have been to Chicago a couple of times. The first time was a sixth grade field trip to the Field Museum. The second time my Dad took Greg and me to a Sox game. This time I was going to actually get to see downtown Chicago. Chicago is a beautiful city with all its parks and the waterfront. Even in the mid-40s on a Sunday morning, people were out jogging or walking through the park.

We were staying on Michigan Ave. at the Hard Rock Hotel. Ford put us up in a two-bedroom suite on the 38th floor. From the window, you could see the park to the south and the Chicago River just to the north. I was in awe at how impressive everything was. I felt like I was in a designer model.


The timing couldn't have been better. I had just gotten unpacked and ready for our afternoon appointment when Clare Thomas was knocking on our door. Kendal let in an absolutely stunning older woman that had to be related to Clare. Kendal led them into our suite and Clare made the introductions.

"David, Kendal, this is Deb Thomas our senior vice president in charge of talent development."

We shook hands and got comfortable to talk.

"Are you two related?" Kendal asked, looking between the two women.

Clare looked at Deb and got a nod letting her share.

"Yes. Deb is my aunt."

Deb was looking me up and down.

"You are very young and you have almost no experience," Deb said. "That is both the bad news and good news. With your youth, we can use you on some campaigns we normally would not be considered for; the bad side is some of our more mature things I can't use you on. The good about no experience is I won't have to break any bad habits. The bad is not a big deal because I hear you follow direction well.

"We are excited to have you join us at Ford. Today I want to introduce you to all the right people. We will make an impression with you. I want every model working at Ford to be successful. I think we can do something special together. The one thing that sealed the deal with us was how competitive you are. You succeed where better men fail. If you will let me, I want to make something special happen. That journey begins today.

"To that end, we have scheduled your afternoon to be spent with our artists. That is what we call the people that will make you even better looking than you already are. We at Ford have a high standard and always want to put our best foot forward.

"After we have you looking fabulous, Clare will sit down with you and go over everyone that will be at the party tonight. I'm sure you would agree that preparation is the key to success. Clare will point out key people for you to meet and give you background on each. You will also meet the representatives from Range Sports."

My stomach growled. Clare shook her head.

"Deb, I think we better feed him first."

She instructed Kendal to order room service and bill it to the room. She also wanted something for the artist to nosh on; I ordered the cheapest thing on the menu, which was a turkey burger. I almost fell out of my chair when I saw it was $28. Clare wouldn't allow me to get it on a bun or with fries. I got a steamed vegetable medley and wild rice. Being a model is going to suck.

The afternoon started with Kendal and Clare going off somewhere and working out who would do what. I was impressed that Ford had not tried to force the issue of my being represented by two companies. What they did was similar, but very different in some ways.

My first appointment was with a personal trainer. He explained that there would be times when I did not have the access to the equipment I was used to or didn't have the time. He gave me what amounted to a bungee cord with handles on the end. He showed me several exercises that I could do in a hotel room. I hadn't been running much since football was out. He made running a priority. He laid out a plan where my ideal workout would be to run 5 miles, swim for a mile, do 100 pushups and 100 sit-ups each morning before my day started.

The next person I met was a dietician. She gave me a food journal and told me to fill it out religiously for one month. She explained many models have food issues and she wanted to see what I liked and was used to before she tinkered with my diet. She did recommend I make a point of drinking more water. She told me to have a water bottle with me whenever practical. She took some blood and promised that tomorrow she would have suggestions for food supplements.

It was time for the first artist to arrive. Jesse was my wardrobe stylist. She took up almost half of the suite with wardrobe racks. She divided the room with the racks to give us privacy. Much like my experience with the tailor, she took my measurements and pictures of my body. Range Sports was looking for an athletic rugged outdoors type. Jesse talked to me about their styling ideas for my look. I stopped her when she said that and went to get my iPad.

I called Tracy. She and I connected on video chat. I asked Jesse to start over; the girls talked about my current wardrobe. I had no idea Tracy knew the contents of my closet so well. They actually made arrangements for Tracy to go to my place and show Jesse via video what she had to work with. I explained that Jesse would need to give me instructions or guidelines until I learned what went with what.

Deb, Clare, and Kendal were brought over and Jesse presented her ideas. Deb signed off on it and we spent the next hour putting together three outfits. One for tonight's party, the second for tomorrow's meeting with Range Sports, and a third for meeting the executives at Ford Monday afternoon.

The next artist arrived and she was hair and makeup. Deb came over and explained the look they wanted to Maggie. She started on my hair. I was ordered into the bathroom where she washed, and then did several treatments to my hair. I got Tracy back on video chat, and she explained what would be needed to maintain the look, and health of my hair. She was dismayed at my haircut. She made several minor changes and, when she was done, I was amazed at how much better my hair laid and held its shape. My hair was now going to require less maintenance. Always a winner with me!

This was when we had our first disagreement. Maggie made the weird assumption I would be willing to wear makeup every day. She patiently explained the benefits to my skin with certain products. She then showed me how I could even out my skin tones. She even showed me how eyeliner would make my eyes look sexier and a touch of lipstick enhanced the color of my lips. I agreed I looked better. I agreed that I would wear it for shoots and even events. Where I disagreed was wearing it every day.

Deb came over and wasn't happy.

"I am a freshman in high school," I finally said. "If word gets out that I am wearing makeup at school, I will be killed. Do any of you remember what happened to boys in high school that wore makeup?"

Deb and I compromised. I agreed to use the cleansers, creams and Chap Stick to keep my skin and lips healthy, but I did not have to wear makeup in my day-to-day activities. I was already dreading Clare using me as her personal Ken doll to dress up every day.

Clare finished off the afternoon. She showed me the guest list. They had a portfolio on all their clients complete with photos. She emphasized who was in the market for talent and what their preferences were. After she finished, I felt confident I knew whom to talk with.

We then broke for a quick dinner. If you can believe this, Jesse and Maggie did not trust me not to mess up their work. After dinner, Clare quizzed me and when she was confident I was ready, she turned me back over to Jesse and Maggie.

At six p.m., I was instructed to shower and shave. Maggie wanted a clean slate so she could do her magic. After Maggie was done, Jesse made sure I could dress myself. Everyone else must have left for a while, because they started to trickle back in chic outfits. When Deb came back, I was presented to her for final approval.

Clare ordered a bar and food for a pre-party in our suite. There were seven models that showed up, four girls and three guys and I was introduced. Deb explained that they wanted us to interact and get to know each other. We were to be observed together and they would set us into couples for the party.

The girls were all about the same height and body type. They all were around 5'10" with small breasts and tremendous legs and butts. I was happy to see that Ava from my first shoot was one of the girls. The other three were Allison, Allie and Lindsey. I will give them credit; I had a blond, a brunette, a red head and black girl.

The guys were all the same also. They were at least 6' tall, brown hair and in their early 20's. They were clearly older than the girls and I was surprised when they showed more interest in talking to each other than with the girls. Their names were Tyler, Andrew and Louis.

When Ava got a chance, she pulled me aside so we could talk.

"I have been getting great feedback from the pictures we took for my portfolio. I just wanted to thank you because according to my agent I was one step from being out the door."

"I have some news for you ... hang on because I need to have Kendal tell you."

I motioned to Kendal and she joined us. I had noticed that she was doing a good job of keeping me in sight at all times. Tom had insisted because of my age.

"You remember Ava?" I asked Kendal.

"How could I forget? How have you been?"

"Great, I was telling David that, with my portfolio reworked, I'm starting to get some calls. What I need is some actual work," Ava complained.

I was trying hard to keep a straight face. I winked at Kendal to let her know she could give her the good news.

"Well I think David may have found a solution for you."

Ava gave me an intense look. I could tell this is very important to her. There is a hint of desperation in her eyes.

"Kendal, did you bring a check for Ava?" I asked.

"I did, I'll go get it."

Ava was very serious when she asked, "What have you done?"

I just kept quiet. Kendal handed Ava an envelope. She ripped it open and her knees buckled when she saw that amount. Luckily, Kendal grabbed her elbow to steady her. She had tears running down her face.

"Next week my parents were coming to get me and move me back to Springfield. I can now pay my rent and everyone I owe. Thank you."

Everyone was staring at us wondering what I had done to make Ava cry. I put on a goofy grin.

"Makeup! I think we need a touch up," I said.

"I'll give you a touch up," Ava said as she grabbed the back of my neck and pulled me into a steamy kiss.

Maggie came over shaking her head.

"I told you I was going to kick your ass if you messed up your makeup." She looked at Ava. "Come on before he does more damage to you."

She led Ava to my bedroom so she could touch her up. As soon as Ava was safely in the other room, the other models suddenly surrounded me wanting to know what happened.

"Kendal found a creative way to make a few bucks from a shoot Ava and I did. I don't know all the details or how Kendal does it. If you're interested, you should talk to her about it."

Suddenly I was no longer the center of attention and I went to mingle. I was talking to another Ford agent when Clare slid up next to me.

"Deb wants to talk to you before we go down."

I said my goodbyes to the other agent and we found Deb in my bedroom with Maggie finishing up. They had me sit down so Maggie could work while we talked.

"If I had been thinking, I would have just invited Ava here tonight." Deb turned her attention to Ava. "Your job tonight is to stay with David as much as possible. The party is open to people in the business and clients. We are going to introduce David and announce Range Sports as a new client. These parties always bring in a certain number of predators that pass themselves off as producers, photographers or something like that. They all try to sell young naïve talent on how they can help them."

"Be extra careful if they invite you to an after-party. I'm very serious about this, never accept a drink from someone you don't know and trust. We just had a model in LA run into some trouble. We are sending out a memo reminding everyone to be safe. Now I don't expect this to happen. To help prevent that, we are making sure that everyone has a buddy tonight," Deb advised us.

"We will be going down to the party in a few minutes. Ava, could you give us a moment, we need to talk to David," Clare said.

When Ava left, Deb asked me to help some other models.

"While you are here, we would like to do a couple of shoots with you and some of our younger talent. They need some pictures for their portfolios."

"Who, when and where?"

"I like you already," Deb said. "You actually met them. Allison, Lindsey and Allie show promise, and the photos of you and Ava are testing out very well, and are beginning to cause a stir. Modeling is a very competitive business. Many girls only last a couple of months. We try to do everything we can to give them an edge. That is why we are so picky about who we sign and we have a reputation as the best.

"The when and where is we would do it first thing in the morning here in the suite."

"Have you talked to Kendal about this?"

"I wanted to talk to you about that tomorrow, but now is a good time. I would advise you to only have us represent you," Clare said.

"Slow down, I want us to have a long relationship so I will tell you a few things. First of all, I am dating one of the managing partner's daughters. While this is not a business reason to retain them, you have to understand that Tracy is special. She and I are a team and when we are together I feel like we can accomplish just about anything.

"Through getting to know her, I met Tom Dole. He has helped me in ways he will never know. When I was in a bind, he introduced me to Kendal. At the time, she was an intern. She helped organize and direct my recruiting and anything to do with the public. Things like press conferences, web sites, and social media.

"When you approached me about the modeling, they jumped in and helped with contracts and support. I know Ford has much more access to potential jobs for me, but don't sell them short. To date Ford has offered me future bookings in the $40,000 range. With the assistance of Tom, Kendal and Tracy, I have secured a shoot at the end of December that will pay me close to $50,000. I also have worked out a deal to work with an advertising firm and Kendal estimates that we will make upwards of $150,000 over the next 12 months.

"I guess my point is ... why would I ever leave them?"

The room was silent for a minute as what I said sunk in. Deb looked at Clare and smiled, "Slacker."

"Aunt Deb!"

"We will drop the exclusive talk ... for now," Deb said. "Could we get a discount on the shoot since we are doing three for one?"

"I tell you what. I'll do them for free. Just give me full resale rights to the pictures and Ford can use them to promote the girls as they see fit."

"Deal," Clare said. "Would you be willing to do this again in the future with other models?"

I thought about it for a moment.

"But not always for free. I would do it if you come to me. Somewhere within an hour's drive would be fine. It also can't conflict with anything that makes me money or my personal life. Things like my nephew's birthday or football camps. Just call Kendal to set it up."


The party was in one of the Hard Rock Ballrooms. Kendal told me it could hold 300 people. There were two bars set up at each end and a buffet along the back wall. I remembered Kara's advice, 'watch what the other models do and do just the opposite.'

I scanned the room and saw them all talking to each other. They were also hitting the free bars and buffet. I took Ava and Kendal in tow and I started to mingle. I made a special effort to meet people Clare had prepped me on.

One of the cool things Kendal had was an app that scanned business cards. It picks out their contact info and puts it in your contacts in your phone. It also date stamps it and you can add comments like where and why you have the contact. Kendal takes it a step further and adds them to groups. This way, if we need a photographer, all we have to do is look at the group. Whenever she added a contact, we all got the same contact. Each time she added one my phone would 'ding'. After the fifth one, I turned my sound off. While making the adjustment to my phone, I saw I had a text. It was from Tom and it said 'Great Job and Good Luck!'

As I was meeting people, a guy caught my eye. He didn't seem to fit in. He was young, I would guess in his early twenties. He was too short to be a model, maybe 5'10", and he was wearing a suit that did not fit him right. His face showed signs of him being outside a lot. He didn't look like one of the predators that Deb had warned me about since he seemed to be hanging back and watching everything. My gut told me to go talk to him, but he seemed a little skittish. So I sent the girls off to grab a drink and get something to eat. It was almost time for the presentation so I promised to meet them in a few minutes.

I walked up to the guy and he jumped when I said, "Hi, I'm David."

He shook my hand.

"Devin."

Then he got a big smile on his face.

"You're David Dawson right?"

"Yes."

Now I was even more curious. How did this guy know who I was? Then he showed me the program with my picture in it.

"My sister has a huge crush on you."

What do you say to that? You don't want to come off as a horn dog to a brother.

"I don't suppose your sister is here tonight?" I asked

"Actually she is. Would you be willing to talk to her? I know it would make her day."

"What's your sister's name? I'll get her a signed photo."

I was hoping it would show that I wasn't going to hit on his sister.

"Her name is Sandy."

"So what brings you here tonight?" I asked Devin.

"Business ... I don't normally come to these things. I hate getting dressed in a suit and tie."

Something about Devin, I liked.

"Come with me. I think you need to meet some cute girls that will make your wearing a suit worthwhile."

Ava and Kendal had secured us a table. I introduced Devin to both of them and he joined us. Kendal had a couple of my photos and a Sharpie with her. She gave me one and I made it out to Sandy and signed it.

It soon became apparent that Kendal and Devin had hit it off. He had a firm grasp on business and they were soon in a discussion about marketing. Ava and I just sat back, watched them, and enjoyed some people watching. We were playing a game: are they gay or not? Ava had clued me in that Tyler, Louis and Andrew were all gay. That explained why they were more interested in each other than in the girls when we were in my suite.

Then the music stopped and I saw Deb Thomas on the small stage. She welcomed everyone and talked about the merits of using Ford Modeling. She ran a slide show of many of the recent things their models had done either in runway work, print or TV. With each presentation, the models involved would come up and be introduced. She then introduced their newest client, Range Sports.

They ran a video showing all the sporting equipment and clothing they sold. The video then introduced their new youth line. It was well presented and when the video ended, Deb introduced the head of marketing for Range Sports. He gave a quick speech telling everyone about their plans and how they felt Ford was the right company to collaborate with.

"We have the rare treat of having our founder and CEO with us tonight. I would like to introduce Devin Range."

Devin had the decency to blush when he got up from our group to talk. He gave a short speech and then he went off script for the evening.

"Ford has been great to work with. Tonight, I've met the new face of Range Sports youth line, and I am stealing Deb's thunder, because she found us a great fit who happens to be a nice guy. Play the intro please."

It showed shots from my portfolio. When it finished Devin said, "Let me introduce David Dawson."

I got up and made my way to the stage. Clare had written me a speech so I gave it and then I said, "Can I have Sandy Range come to the stage?"

I saw a cute girl that was my age or a little older come up and join Devin and me. He had a big grin on his face watching his sister's embarrassment.

"Devin tells me that you are a big fan." She grinned and nodded. "He asked me give you this signed picture."

She had a big grin on her face, she hugged her brother, and then I got one too. Deb came back up and Devin, Sandy and I went back to our table.

Deb had one other person to introduce. I was in complete astonishment when she introduced Adrienne. I had grown up fantasizing about her. She had been a Victoria's Secret and Sports Illustrated model. The thing that sets her apart was she had DD breasts that seemed to defy gravity. She was also more toned than most models. That was why she was still going strong at 26.

To be honest, I had no idea what she was saying. I was just drinking in her beauty. She was the classic California girl with blond hair and sun-kissed skin. Rumor was she was in a relationship with a woman, but that there were guys in her past. That at least gave me some hope. Never mind the 11-year age difference. Every guy could hope couldn't they?

When the presentation was done, they started to play music again and I noticed they had a dance floor that a few couples were using. I asked Sandy if she would dance with me. I'm not sure who was more surprised, Devin or Sandy.

It was a slow dance so I took her in my arms. She looked up at me shyly.

"Do you have a girlfriend?"

"Yes, I do. Her name is Tracy and she is special. I would love for you to meet her."

"Really?"

"Yes, why wouldn't I want her to meet my new friend?"

"Really?"

"Yes, I think you two would hit it off."

"Really?"

"Uh Sandy, are you brain damaged?"

"Shut up! I'm trying to decide if this is a dream or if it is really happening."

I leaned down and kissed her. If she was off balance before, that completely messed her up. I took her back to her brother and he saw the zoned-out look in her eyes.

"Is she always like this? I think she is brain damaged."

She hit my shoulder.

"David kissed me," she said as if that explained everything.

I looked at Devin and just shrugged. He lost it, which got him a slug in the arm from Sandy.

Clare stepped up to our table.

"Mr. Range, David, and Miss Range, would you mind having some pictures taken and meeting some people?"

They had setup a room for photos to be taken. I saw Adrienne getting her picture taken and I had a stupid grin on my face.

"Who is brain damaged now?" Sandy whispered.

I turned and gave her the arched eyebrow.

"Listen smarty pants. If you aren't careful, I will spank your cute little butt."

I heard, "I might pay to see that."

I turned in horror to see Adrienne grinning at us.

I recovered quickly.

"For you there is no charge. I have a suite upstairs. We could go up there and handle this problem, and anything else you might want to do."

Devin choked as he asked Kendal, "Are there any women safe when he is around?"

Kendal shook her head sagely.

"No, not really?"

Adrienne was trying not to laugh at me, but just barely.

"Clare. I like this one," Adrienne said. "He is fearless and that should be rewarded. Set something up that he and I can do together."

She grabbed my hand.

"Come on handsome. Let's get our picture taken."

We went up and took a couple of pictures together and then she messed up my hair. I looked at her in surprise. She had a gleam in her eye.

"Let's give them something that will make the paper," she said.

She gave me a sweet kiss on the lips. I don't know what came over me but I put a lip lock on her and gave her a serious kiss. I found her huge tits pressed against me and I grabbed her ass to pull her in tight. She had her fingers in my hair holding me in place as she finished what I started. If my knees had not locked, I would have collapsed when she broke our kiss. We were both trying to catch our breath.

"You are a naughty boy. If I was younger, I would make a serious run at you."

With that, she was out the door.

I had no idea how I got into the makeup chair with Maggie looking at me with disgust.

"What did I tell you about you dying if you messed up my work?"

Kendal came over shaking her head.

"You always say go big or stay home. At least you live by what you preach."

"You have to get me copies of those pictures. One of them is going to be my Christmas Card picture this year."

Kendal laughed.

"You are bad, bad, bad ... and your friends will shit when they see that card."

Maggie had me presentable again and I joined Devin, Deb and the head of marketing for Range Sports for a few shots. Devin then got his sister to take a few with the three of us. He then smirked and left us alone for a couple of shots.

"You put your hand on my sister's ass and we will have words," he said as he walked away.

Everyone laughed. They laughed harder when Sandy grabbed my hand, put it on her ass and dared me to take it off; I just shrugged and kissed her forehead. We then got a shot of Devin trying to strangle me.

Devin and Sandy joined Kendal and me as we went back to our suite. I didn't know we were hosting an after-hours party. When we walked in, the other models all started clapping. I saw the photo room had a live feed in our suite. Allison filled me in. For years, there has been a pool to see which guy could get to first base with Adrienne.

They had recorded the whole thing. Kendal provided commentary as it unfolded in the replay.

"Here the unsuspecting female rewards our hero with a chaste kiss." She looked around the room. "Girls never ever let David get his lips on you. You are about to witness what happens. Your brain goes blank and all you can think about is the two of you. The whole world fades as you realize you are no longer in control. I swear that Adrienne could not tell you her own name.

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