Stupid Boy - Freshman Year - Part II - Cover

Stupid Boy - Freshman Year - Part II

Copyright© 2014 - 2015 by G Younger

Chapter 18: San Francisco

Coming of Age Sex Story: Chapter 18: San Francisco - Part II of a 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. 2015 Clitorides Awards as the Best Epic Story (1st) / Best Humorous Story (1st) / Best Romantic Story (2nd)/ Best Author (2nd).

Caution: This Coming of Age Sex Story contains strong sexual content, including mt/ft   mt/Fa   ft/ft   Mult   Teenagers   School   Sports   Rags To Riches   Group Sex   Anal Sex   Oral Sex   Safe Sex   Slow  

Sunday May 18, 2014 – Freshman Year

Kendal came and picked me up after church and brunch. We were meeting Tami, Missy, and Harper at the airport. Tami had gone home with Harper over the weekend. They had stayed for graduation at Wesleyan. The girls were excited about their big adventure. It turned out that they were seated with Kendal and Clare. Did I really want all of them comparing notes?

I boarded first class to find a kid a little older than I was, was sitting in my seat. I hate it when that happens.

"Hey, I think you're in my seat," I told him.

He pulled out his boarding pass, and sure enough, we both had the same seat number. The new security protocols and scanned tickets were supposed to insure that this couldn't occur. The stewardess came over, saw the boarding passes and cringed. I'm sure she also hates it when this happens, especially in first class. They made me stand in the galley while they tried to figure it out. Looking around, I could tell that the flight was completely full.

They tried to offer me some deal to wait for another fight.

"Look, I have a job! I've got to be in San Francisco. I have five other people who are traveling with me on this flight. My reservations were made weeks ago. When was this guy's reservation made?"

They sent a gate person to talk to me.

"Mr. Dawson there has been a mistake. We're sorry, but you'll have to exit the plane."

"I have a modeling job I have to get to. I have five people with me on this flight," I said repeating myself. "I have a reservation. Why are you not talking to the other gentleman? When was his reservation made?"

"It doesn't matter," said the gate agent, who looked younger than me. "I'm going to have to ask you to exit the plane."

"If that happens, I'll be forced to talk to my lawyer."

"Yeah, right, come on kid."

"Hang on. My lawyer and agent are on the flight. I think you need to talk to them before you do anything rash," I said as I started back to coach.

The idiot tried to grab me as I stuck my head through the curtains and yelled, "Kendal, Clare? Can you come up here for a moment?"

They could see I was pissed. They came up and talked to the gate person. Next thing I knew, we had several managers, and then a US Marshal. I guess holding up a flight got everybody's attention. It turned out that the kid was an employee's son, and the gate agent had overridden the system to give him the seat. The little shit knew it, too.

Once that was uncovered, he was quickly taken off the plane. The Marshal was not happy because this wasn't supposed to happen. I figured the airline could figure it out from there, and I took my seat. The stewardess tried to make nice, but I was in no mood to reciprocate. I put my headphones on and tuned everybody out.


When we landed I got a text from Chuck, my security guy. He had gotten a big SUV and would meet us out front once we got our bags. Devin had reserved an apartment for Tami, Harper, Missy and me. Kendal, Chuck and Clare were staying at the Hilton. Chuck dropped us off at the Fairmont Heritage Place, at Ghirardelli Square. The hotel where we were staying was pricy, hence the reason Kendal, Chuck, and Clare were staying elsewhere. We made plans to all meet at our apartment and then go to one of the piers and do some exploring before dinner.

The girls were impressed with the three bedroom apartment. It was very modern and had a huge window overlooking the bay. The facilities were fantastic. They had a game room with a pool table and outside there was a deck with plenty of seating and a huge fireplace. I could see snuggling by the fire overlooking the bay as the sun went down. I also needed to thank Devin and Sandy for taking such good care of me.

The girls wanted to go to Pier 39 to do some shopping, and then find a nice seafood place for dinner. Chuck and Kendal showed up. Clare had to prepare for tomorrow and had begged off. We walked down to the pier and saw the sea lions. They were a noisy bunch. They had floating docks for them to get a little sun. It was funny to see them knock each other off the dock. The girls left Chuck and me to fend for ourselves while they hit the gift shops.

I found a place selling mini-donuts, and bought a bucket to share. That was a good call. We found a bar with outside seating so we could people watch. This gave me a chance to talk to Chuck about the coming week.

"My best friend and two of our good friends want to check out colleges this week. I want you to go with them and keep an eye on them. They don't know their way around and I would just feel better if you were with there. I know that I'm your #1 responsibility but, once I'm on the shoots, we should be safe."

"I went to school at San Diego State. I have friends that went to both USC and UCLA. Do you know where they want to go?" Chuck asked me.

"I know for sure that they want to visit Stanford and USC. I've seen Stanford and I'm going to football camp at USC. I'm sure they will want to have some fun too. I brought Tami and her friends as a birthday gift to her. So I guess, we just go with the flow and keep them out of jail."

"Don't put that on me. You just jinxed it," he suggested.

"Dude, have another donut and lighten up," I ordered him.

"You do know that LA is almost six hours away," Chuck told me.

"It looked closer than that on the map. I'll let Tami know. She and the girls can work it out."


When the girls came back, they had bags and big smiles on their faces. Tami jumped in my lap and showed me all the crap, I mean bargains, she bought. Harper noticed Chuck was drinking a beer. She gave him an innocent look. Oh, no.

"Chuck, you look so manly in those sunglasses," Harper started in.

I always teased him about wearing his security sun glasses. He looked like a bad characterization of a Secret Service guy trying to be under cover. He looked at me. I shook my head to let him know I hadn't put her up to it.

"I was wondering if you could stop by the liquor store and get us some things. It seems the apartment doesn't have any wine or beer."

He looked at me again and I just shrugged. As long as they didn't go wild, I didn't see the harm in it.

"I'll pick up some stuff for you on the way back," he told her.

We all thanked Chuck and then the conversation turned to eating. Tami got her phone out and tapped the Yelp app. I had seen a crab place, but she informed me that it didn't have enough stars. The girls decided on a historic seafood place. They had been in business since 1936 and, best of all, we could walk there.

Chuck suggested I get the clam chowder in the sourdough bread bowl. The girls ordered a variety of appetizers. The crab cakes were so good that I ordered a whole cracked Dungeness crab that had been oven roasted in garlic butter sauce. It was to die for. The girls all wanted to order dessert but I reminded them that Ghirardelli Chocolate was just down the street.

On the way back, we stopped at a grocery store so I could get a couple of things. I needed fresh fruit, eggs, bacon ... and purchased sour dough bread, it was an impulse buy. They had a bakery that had just made a fresh batch, and we were drooling from the fresh bread smell. We then went to the liquor store. Harper and Missy knew which wines they wanted. Tami wanted a six pack of beer. She just ignored my look.

We then went to Ghirardelli. Kendal talked me into splitting a chocolate shake with her. The three girls got a big sundae and split it. Chuck went with a hot chocolate. Kendal made a good call on splitting the shake. If I continued to eat like this, I was going to completely blow my diet!

When we got back, Chuck and Kendal went back to their hotel. The girls were going to Stanford tomorrow and made arrangement for Chuck to pick them up. I told them about the travel time issue to LA. We all changed into comfortable clothes, and Missy opened a bottle of wine. Tami and Missy went to the living room, when Harper took my hand and led me to the deck by the fireplace.

"How did things turn out for Ray?" I asked her.

The last time I had seen Harper's friend, he and his roommate Lou were being taken back to school by faculty. Harper had told me that he might not being asked back to Wesleyan.

"It's official. He won't be back next semester. I hate to say it but I'm relieved. It was getting too painful to see his life spiral out of control. The worst part is that his parents had no idea what all was going on. He came home and told them that he was gay and had been kicked out because of underage drinking and drugs. You have to know his family. They are very straight laced. They aren't taking it very well.

"Then my parents flipped out. I guess I was supposed to tell them about it. I had to bring Tami home to help talk them off the ledge. They thought Wesleyan was letting us throw wild parties. I should have told them about the weekend I spent with you. That would have freaked them out."

"So is Ray going to public school next year?"

"Oh, it gets better. He gets to go to some religious boy's school where they can cure him. Even my mom and dad think that is a terrible idea. They assured me that they will get that stopped. When his parents calm down, they'll find a nice out-of-the-way school to ship him off to."

"That sounds much better."

"At least he isn't going to go to some public school," she said, meaning every word of it.

I sometimes forget what a social difference there is between Wesleyan girls with money and what my life is like. I should have learned my lesson with Jennie. Harper and Missy came from the same background. I was never going to be the boy they brought home. Harper didn't even notice I had gone quiet. She was lost in thoughts of her best friend.

I got up and she just smiled at me. She needed to be alone. I went back to the apartment to find that the girls each had chosen a bedroom. My bags were in the hall. I went into the living room to find out what was going on.

"What is with my bags in the hall?" I asked Missy and Tami.

"We were going to let you choose which room you wanted to stay in."

I just stared at them. I wasn't in the mood to play games. Tami could see their little ploy was not going over well. I thought about it for a moment. The original plan was for four bedrooms. I think I assumed some things and I shouldn't have. This was Tami's birthday present, a girl's week.

My phone dinged and I had a text message. It was from Sandy Range. Both she and Devin had arrived. I sent her one back telling I would call her later.

I went and sat down with Tami and Missy.

"We talked about it and we decided that this week was not going to be about sex. Missy and Harper agreed that they have the same issue I have. If we're with you and then you leave, we'll miss you too much," Tami told me.

I could read between the lines. Tami didn't want me having sex with her friends. I knew I needed to find somewhere else to stay or I wouldn't be a happy boy all week. Harper was worried about Ray so she wasn't going to be good company. Missy was not going to go against Tami.

"So do you even want me to stay here? Should I get another room for the week?"

"No, it's not like that," Missy said getting worried.

"You know what? I'm sorry," I told them as I got up.

I grabbed my bags, put my key on the kitchen table, and walked out. I sent a text to Sandy to find out what room she was in. I found it and knocked on the door.

"What are you doing here?" she asked seeing me with my bags.

"Could you use a roommate for tonight?"

She looked confused but let me in.

"What's going on?" she asked me.

"I really don't know, but I need to get some sleep before tomorrow."

"Well, I have an extra bedroom and you're welcome to. If you need to talk, I'm here."

"Thanks, but I just need to get some sleep."

She showed me where to go and I unpacked and was getting ready for bed when my phone rang. It was Tami. I just turned off my phone and went to bed.


I barely woke up when I felt the bed move. Someone got in bed with me and laid their head on my shoulder. By the size and hair style it had to either be Tami or Sandy. I went back to sleep.


Monday May 19, 2014 – Freshman Year

My internal alarm clock went off at seven, but it was on central time, so it was just five in the morning. I had to pee and I didn't want to wake up my bed mate. I was a little nervous of what Devin would say if he found Sandy in bed with me. That, plus the mess with Tami & Company ... I needed to go run to clear my head. I put on running clothes and headed out. I realized on the elevator down, that I didn't have a key to get back into Sandy's room.

I headed north until I found the bay and then I headed east until I ran into the Presidio. It was a former military base that was now a park. I found a group of runners and followed them. We came out of wooded area and I could see the Golden Gate Bridge. After about an hour, I was getting hungry. I headed back and found a restaurant that was busy with a breakfast crowd.

I turned my phone on and I had just one message. It was from Tami, from shortly after I left to run.

'Hey, I take it you went running since you weren't here when I woke up. I moved your clothes back to my room in the apartment, and left your key at the desk. When you're ready to talk, call me.

'Missy and Harper straightened me out and I need to apologize. I bet you're getting sick of me having to do that. Anyways, just come home.'

That solved the mystery of who was in my bed last night. The waitress came and I ordered hot tea, steak, eggs and sliced tomatoes. I quickly ate and headed back to the apartment. I grabbed the key at the front desk and went to the weight room and lifted. I was scheduled to meet Devin at nine am. It was now 8:30. I went upstairs and came into the apartment to find girls eating breakfast.

I just gave them a tight smile and went and took a shower and got ready. I got on my iPad and sent Mom an email to let her know I made it okay. I sent one to Eve telling her I missed her. I grabbed my chargers since both my iPhone and iPad were getting low. I would charge them sometime today.

I braced myself and walked out to the kitchen. Chuck had arrived and Missy and Harper must be in their rooms getting ready. Tami could tell I wasn't ready to talk, but that didn't mean she wouldn't. She took me into the living room. I looked out at the San Francisco Bay and just stared out into space. She touched my cheek to get my attention.

"I wasn't a very good friend yesterday. I talked both Missy and Harper into backing off. It was stupid. I was jealous because they seemed more excited about spending time with you, than with me. We had a long talk last night about our feelings about you. They both said they would not stand between you and me being together. But while we were talking, I realized two things. The first is: I'm not ready to claim you. The second is that I need to get over being jealous when you are with someone else.

"I honestly don't know where it came from. I think all of us being together at the Formal triggered it. Knowing that you were with someone else, in the next room, kind of made me crazy."

This sounded like another conversation I'd had ... with myself!

"Look, this trip is for you. I don't want to come between you and your friends. It is probably best if I find somewhere else to stay."

She shook her head.

"No, part of this trip is to be with you. I love you so much it hurts. I'm not wasting this trip with you not being here with me. I don't get to see you enough. I also know that Harper is going through a rough patch. It seems she is comfortable talking to you about it. And Missy adores you. We all want you to stay with us, and I want you to also spend time with them.

"David, I messed up. Can we put this trip on a restart and just forget about what I said and did?" she pleaded with me.

"You know I won't abandon you. If you want me to stay, I will. I'll even be friends with Missy and Harper, but I will respect your wishes and that is all I will be."

"I don't know if that is what I really want. I know you have to go. Would it be okay if we spend the evening alone and talked – to each other?"

"Yeah, that's a great idea. I'll see you when I get back. I think we should be done by seven o'clock."

She kissed me and I left to find Devin.


Devin, Sandy and Lana were waiting for me. Sandy gave me a knowing look that had a hint of sadness. She knew that I was having troubles with Tami. I didn't want to talk about it in front of others, so I just smiled at her.

"Let's get this show on the road," Devin announced and led us to the car that was waiting.

We were headed to Redwood City to a fitness center. They had tennis courts, pools, a weight room and rooms for yoga and the like. Sandy handed me a model's card.

"This is who you are working with today. Her name is Rose. She has worked for us before so we aren't going to have the same issues we did in England," Sandy informed me.

I read the card. Rose was five foot and eight and a half inches tall, had a 34B bust with brown hair and brown eyes. She looked Latin, with a dark complexion and full kissable lips. Oops, where did that come from? Based on what I saw, I was looking forward to meeting her.

The fitness center was unbelievable. It sat on ten acres and looked like a resort. Devin hurried us in, and I met our photographer for the week, Trish. She was all business and I liked her from the start. She looked me over and called the makeup gal over.

"We need to tan him. Do it so it will last, because I don't want to have to do it every day."

"All over?" the makeup gal asked.

"I need to see his body first. David, go slip on a swimsuit and come back."

I came back to find Lana had joined them. I thought we had gotten past this with her, but she was eyeing me like the last piece of pizza at Monical's. Trish had me turn bend and twist while she checked my skin tones. She then came up and pulled my suit down to expose my left butt cheek.

"Do all of him and I want him shaved. He is in fantastic shape and I don't want anything distracting from his form. I also want his hair trimmed. We want a consistent look," she said as she pulled my England photos for the makeup gal to use as a reference.

I remembered that Ford calls them artists. I spent the next hour getting hair removed, a haircut, tanned and makeup applied. Next, they put me into a tennis outfit and sent me to the court. Rose was running late because of an accident on the 101.

When I got to the courts I was introduced to the tennis pro, Pam. Trish had her hit me balls.

"I want you to move him from side-to-side and have him work up a sweat," Trish instructed Pam.

"David, try to hit the ball, but don't worry if you don't. We are just getting warmed up," Trish reassured me.

By the time Rose got there, I was soaked. Pam had run me ragged and I was gasping for air. Trish didn't even give us time to say hi. She sent Rose out so it looked like she was my doubles partner. She had me run around and hit all the balls while Rose would bend over and distract me with her cute butt.

It made for some great shots. It looked like I was killing myself to win while Rose flirted with me. The best one was when Rose dropped her racket and bent over with straight legs. Oh my. Pam drilled me with a tennis ball and Trish caught the moment perfectly.

It seemed that Trish didn't want me to get to know Rose, because she made sure we were separated at all times. I went back to wardrobe and got dressed for the gym. Trish had Rose and me act like we were working out next to each other. I had another reminder for Devin and Sandy: Range Sports needs to be commended on their fine line of spandex shorts for women.

When we were done, both Rose and I were blushing because it was obvious we had been checking each other out when we thought the other wasn't looking. Devin loved Trish's approach. By keeping us apart, it had created an air of mystery. The sexual tension didn't lessen at the pool.

They had me model everything from board shorts to a Speedo. Rose was in a one piece, then a modest two piece and finally in a bikini that had Mr. Happy very interested. Unfortunately, that is when Lana decided to get involved.

"David, I think you are getting too much sun. Come over here and I will put some sun block on you," she said as she grabbed my arm.

Trish slowed her down.

"I'm sorry, but I don't want him oiled up, yet. I need the natural skin so there are no reflection problems."

"Well, let me know when he needs to be oiled up, and I'll get him ready for you," Lana offered.

Trish just gave me a helpless look and Rose smirked.

Half an hour later, Kendal announced they were going for snacks. That sounded like a good idea to me.

Trish was to the point she wanted us oiled up to give the pictures a different texture. She wanted the light to reflect off of us.

So I went back to makeup, only to find Lana with a bottle of oil. Oh, crap, and everyone else was getting snacks. I would have to talk my way out of this one, alone.

"Lana, this isn't a good idea," I warned her. "I don't think Devin would like it if he found you putting oil on me. Frankly, I am quite uncomfortable with this."

"Let me worry about Devin. We need to get you ready for your next shoot," she said as she put oil on her hands.

"No!" I said as I put my hand up to keep her away.

I could see her resolve falter, and then she took a deep breath.

"If you ever want to work for Range Sports again, you'll do as I say," she ordered me.

"That would be sexual harassment," Devin said as he stepped from behind a dressing screen with a grim expression on his face.

I made a hasty retreat to find Kendal, Clare and Sandy waiting on me. I was pissed.

"Where were you guys? That was a very bad scene."

"That was my fault," Sandy told me. "Devin wouldn't believe that Lana was not as ... committed as he was. I convinced him that he needed to see it for himself. I knew that with you running around in a Speedo she would soon be after you."

"So I was bait?" I said, worried. "I feel so bad for him, and I was involved. He must hate me,"

"No, he was hard to convince. He wouldn't agree to do this with anyone else. So don't worry," Sandy told me.

Yeah, right. I wouldn't care who my fiancée was hitting on, I would have a problem with the guy involved!

Trish saved me by telling me that I was on the clock and to get my skinny ass in gear. That made me chuckle, and put me in a better frame of mind. The makeup gal oiled me up, and I found Rose sitting on a lounge chair without any oil on.

"David, you have been a good boy all day and not hit on Rose. I'm going to reward you. I want you to put oil on Rose, and do it in as erotic a fashion as you can, without making it X rated," Trish told me.

I smiled and looked at Rose.

"Are you okay with this? I don't know you very well and I don't want you to be uncomfortable," I asked her.

"Oh, yes. I've seen the looks you've been giving me. The attraction is mutual," she purred at me. "Let's see what you can do, big boy."

"You have no idea," Kendal warned her.

I had her sit in front of me and I began by giving her a scalp massage. Rose was moaning by the time I had worked the knots out of her neck and shoulders. Rose was enjoying my massage. I found she had multiple sore spots on her back, and not the normal tension tightness.

"Did you hurt yourself?" I asked in concern.

"It was stupid. I was doing runway work in LA last week and I fell off my high heels. When I tried to catch myself I felt a twinge in my back."

"Lie down, let me see if I can help."

I took my time and worked on her. At some point I forgot about Trish and just focused on Rose. About half way through I straddled her waist so that I could get the right angle at a particularly troublesome spot. Rose was grunting and moaning as I worked on her.

When I finished her back I suddenly realized where we were. I had been rubbing Mr. Happy on her delectable bottom and he knew exactly where he was. I had to get up and take a quick break to readjust things. The problem with a Speedo is that readjustments really don't make much difference.

I went back and worked on oiling up Rose's legs and feet. Her feet were sore also from wearing the shoes she needed for modeling. Rose was a limp noodle when I finally told her to roll over. I started on her face and neck. Trish told me she wanted me to sit behind Rose and reach over her shoulders. We got the chair adjusted and I sat down with Rose wiggling her butt at me as she sat between my legs.

I reached over and did her chest above her breasts. Rose leaned back on me, and my hands accidentally slipped under her suit and I found my hands cupping her breasts. I heard the camera going off and no one stopping me so I teased her nipples.

Rose reached back and grasped my dick through my Speedo. Oh crud. We had just crossed a line. I let go of her breasts and reached down and pulled her hand off of Mr. Happy.

"We have to slow down," I warned her.

"I don't want to," she responded.

Kendal stepped in.

"Enough. David has clauses in his contract that we are very close to breaking. I have to insist that we take a break at this point, and discuss the direction of this shoot."

The effect was like throwing a bucket of cold water on us. Trish snapped out of it and said she had what she needed. She took Clare and Kendal to look at the photos leaving Sandy with Rose and me. I guess we needed supervision.

Trish came out and asked for Sandy. Kendal and Clare came out while Sandy went in to look at pictures. Clare pulled Rose aside and I got Kendal.

"I'm disappointed in you. You need to remember that on a shoot you cannot be doing things like that."

"I'm sorry, it wasn't planned. She leaned back and my hands slipped."

"I know that, but you didn't have to leave them there."

I looked at her like she was crazy.

"Really?" I asked.

She shook her head.

"I'll give you some credit for remembering to draw the line when she grabbed you," she teased me as she looked down and saw I was still aroused.

I decided now would be a good time and go take a shower and fix the problem. When I was done, I came out in a robe. The gal from wardrobe told me we were done for the day, so I got dressed. By the time I was done, Rose had left. Kendal handed me a piece of paper that had her number and a request to call her.


I got back to an empty apartment and I decided to go do my afternoon workout. I went to the exercise room to find several people working out. I went over to the open section and began my 30-minutes-of-hell routine that Cassidy had taught me. When I was done, I collapsed on the floor trying to catch my breath.

"That was intense," a male voice said.

I looked up and a good looking guy in his late thirties and a girl who was about my age looking down at me. I stood up and realized how tall they were. She was just a few inches shorter than I am and he was at least 6'6".

"How often do you do that?" the girl asked.

"I do that five to six times to week ... when I can. I run about every day and lift at least three times per week. I'm trying to get in shape."

"When do you run and lift?" the girl asked.

"I try to get up early and run. I have to get it done before I go to work. Then I work out in the early evening ... if I get off early enough."

"Where do you work?" the guy asked, who I was assuming was her dad.

I decided not to tell them I was a model. That usually got weird reactions from fathers.

"I work for Range Sports."

"What are you getting in shape for?" the girl asked me.

"I play football. I'm going to some camps this summer, and I need to be able to perform for the recruiters."

"What..."

"Hang on, I'm David Dawson."

"I'm Tara, and this is my dad."

"Jack Quaid."

"What's up with the twenty questions?" I asked.

Tara looked at her dad.

"Tara plays volleyball. We're on vacation and she has been bugging me about needing to work out. She saw you trying to kill yourself, and wanted to know if you would work out with her."

"I need someone that might be able to keep up with me. I think you might have a shot," she bragged.

My phone beeped. The girls must be back. I liked to run with someone, maybe she could keep up.

"Meet me at the entrance at six tomorrow morning, and we'll go running. If you can keep up, I'll work out with you in the afternoon. I've got to go."

"That is awful early," she complained.

"Only time I can do it. Take it or leave it," I said as I headed back to the room.


The text was actually from Sandy. I stopped at her room.

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