Stupid Boy
Chapter 11: Stranded

Copyright© 2014 by G Younger

Coming of Age Sex Story: Chapter 11: Stranded - 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  

Saturday October 26, 2013 – Freshman Year

Tonight was my first date setup by Tami. I dressed in my Dockers, dark blue sports coat, and one of my fitted shirts with boat shoes. Of course, Tami picked the whole wardrobe, down to the silk boxers. I played fashion show trying on several outfits until I heard a giggle that was not Tami's. It turns out that she had half the dorm watching me on a big screen TV in their lounge. I didn't let on that I knew what was going on. It was payback time.

"That one doesn't work. It doesn't bring the color of your eyes out. Show me the other one I picked out," Tami commented on my current shirt.

"How many more shirts do I need to try on?"

"Quit your whining. You want to look good for your date, don't you?"

"I really do. I have been looking forward to this. I had to beat off like five times so far today just to keep this guy down." I cupped my package. "God, I'm getting hard again."

"TMI, David." I saw her squirm in her seat.

"Man, I wish you were here. I get so hot thinking about the face you make when you orgasm."

I scrunched up my face, bit my lower lip, and rubbed my chest moaning.

"SHUT THE FUCK UP! I've never made that face in my life!"

"Tami, you're making me hard again. You want to watch me jerk off, and we can talk dirty to each other?"

"NO! You fucker ... when did you figure it out?"

I gave her my perfect little angel face, which we both knew was a bunch of crap. "What are you talking about?"

"Crap." She knew I caught her and decided to fess up. "Uhmmm ... Okay, promise not to get mad?"

"No need, you set me up for a fashion show," I laughed. "If you gave me a heads up, the girls might have gotten a better show than listening to me whine. What do you want me to wear tonight?"

I was dismissing her little prank. She knew it was game on and our little video chat war was just heating up.

"The second outfit. We all think your butt looks cute in those pants." She gave me a sheepish grin.

"Nice. You only made me try on six other outfits until I caught on. Who is my date tonight and what are we doing?"

"Your date tonight is one, Ms. Jennie Wesleyan." She saw the look on my face. "Yes that Wesleyan. I believe you met her uncle when you were at the University of Kentucky. She is picking you up at 4:30 p.m. It's an hour's drive to the country club. You'll be escorting Jennie to some family function."

"You're killing me. Please tell me it isn't some tweener's thirteenth birthday with a crush on Double D."

She cracked up. I told her about some of the weird requests I was getting. This sounded too much like a setup. Tami knew I would track her down if this whole thing were some sick fan's fantasy date.

"No, Jennie's older sister is introducing her most recent boyfriend, and she needs some serious eye candy. I also think you and Jennie will hit it off. She is a lot of fun but is stuck here so she doesn't have a boyfriend. Apparently, her mom wanted to set her up with some twit."

"Does she have a sense of humor, or do I have to be on my best behavior?"

Tami shook her head.

"She would string us both up if you embarrass her. All you have to do is survive dinner, and then she has some plans afterward that sound fun."

"Alright, I trust you. I'll call you on Sunday and give you a report."

We logged off, and I had three hours to get ready so I kicked back and took a nap.


When I got up from my nap, I was ready for whatever tonight might hold. I was actually looking forward to going out with someone new. It felt good not to worry about a relationship. I planned to just take what comes and have a good time though there was some pressure going out with a Wesleyan. I trusted Tami not to get me into something that might end up biting her in the ass if I messed up.

Right at 4:30, a black Lincoln Town Car pulled up and the driver got out.

"Mr. Dawson?"

"Yes."

"Ms. Wesleyan apologizes, but she will have to meet you at the Country Club."

He opened the back door for me to get in.

"How long is the drive?"

"An hour and fifteen minutes."

"Okay, I'm not riding in the back for that long. I'll make you a deal. When we get about five minutes out, we can stop and I will ride in the back."

He just raised his eyebrows but did not object. When we hit the highway, I could see the driver had something to say. It turned out his son was the quarterback for Eastside High, Mark. We talked football for the majority of the ride. When we got close, I asked him about my date.

"You seriously have never met Jennie?"

"No, this is a blind date."

He was the Wesleyan's driver so he was aware of most everything going on.

"She has been talking about you all week. Mark is jealous because he has a crush on her."

"So I take it she is cute."

"Cute, smart, and she has a wicked sense of humor. Let me give you a tip. If you fawn all over her, and I wouldn't blame you if you did, she will take advantage of it. Don't let her boss you around. She likes strong guys. Don't be a jerk though. She won't tolerate that."

"Sounds like I'm going to have a good time tonight."

Mark's father smiled, but then his face clouded over.

"I almost forgot. There is a dance after dinner. Mark and some of his buddies are going to be there. If they try to dance with Jennie, let her handle it. She knows everyone, and they know her. She has dealt with this group all her life."


When we got close, I jumped out, put on my sports jacket, and got in the back. As we pulled up to the country club, the driver said, "Jennie is waiting for you. She is the blond."

Damn. I could see why Mark had a crush on her. Jennie Wesleyan was a fox. She was tall. I would guess about 5'10", with long blond hair that was naturally curly. She had a slim figure and what looked like a 'D' cup. She was wearing her school uniform, which was a short plaid skirt with a white button up blouse and blue blazer. I saw her coming to the door to open it so I pulled out a five and folded it in my palm.

When we came to a stop, she opened the door, and I stepped out. I handed her the tip and walked into the country club. Out of the corner of my eye, I saw her driver double over laughing as she showed him the tip. She stormed into the Country Club and got into my face.

"Who do you think you are?"

I gave her the same look I gave Tami earlier. It didn't work with her either.

"Was I not supposed to tip you for getting the door?" I couldn't help myself, and I grinned. "Jennie, David Dawson, nice to meet you."

"You jerk."

Luckily, there was no heat in her words. I could see a twinkle in her eyes that made me wonder what kind of payback was in store for me.

"So give me the lowdown on what you have planned for me tonight."

She took my arm and guided me through the country club. Wherever we went, all eyes were on her. She led me out to a patio. It was glassed in and gave a view of the golf course. A waiter brought us hot tea and finger sandwiches. She suddenly seemed shy.

"I was trying to impress you with tea. I can see now that it comes off a little snobbish. I mean seriously, who has tea anymore?"

I liked a girl who could make fun of herself.

"Jennie, I'm all about experiencing new things. I have never had afternoon tea, so let's spend some time and get to know each other. Tell me what the family dinner is about so I don't embarrass you."

"Shit, I owe Tami lunch. I bet her you would just talk to my tits, and I would have you wrapped around my finger in the first fifteen minutes. You looked me right in the eye when talking to me, and you have me so flustered that I feel like a naïve school girl."

"Tami set you up. I have a super power that only a handful of people are aware of. Can I trust you with my secret?"

"She did say you were a 'stupid boy'. I'll bite. What is your super power?"

"Beautiful girls don't make me nervous."

"I call bullshit."

"No, it's true. My older brother is a legend at my school for dating the best looking girls. He would bring them home, and I would talk to them while he went off and did whatever. If you don't believe me, ask your uncle to tell you about the time I met Ashley Judd."

"Okay, my uncle isn't going to be here tonight. Give me your phone. I'm definitely calling bullshit now."

I handed her my phone, and she called her uncle.

"Hey it's Jennie..." I couldn't hear what he was saying. "I am sitting here with David Dawson. He told me you would remember him meeting Ashley Judd."

She listened for a while and then gave me a shocked look.

"He did not!"

There was a pause as she listened.

"Did he really?"

Her uncle was clearly on a roll.

"He got all of them to accept..."

They said their goodbyes, and she gave me back my phone.

"Okay, so you have a superpower. My uncle also likes you. It is rare that someone impresses him, especially someone our age. Did you really get everyone to accept offers from Kentucky that weekend?"

"I guess I did. They all wanted to but didn't know how to ask. So I gave them a little nudge."

"What is this story about condoms?"

"Tell you what. That is a story I only tell close friends. Let's see how the night goes, and I might tell you later."

"Can you hit on my sister, tonight?"

Both my eyebrows went up on that one. This conversation had taken a sudden turn.

"What!"

"Sorry." She gathered her courage. "My sister's new boyfriend is a complete snob. He treats her like shit, but I know her. She wants what she can't have. I need her to become interested in you, and you have to resist her. She'll dump the jerk."

"So your big plan for tonight is for me to be your date so your sister will hit on me and dump her boyfriend?"

"NO ... well, okay, yes. I don't know. When you put it that way, it sounds kind of like a sucky plan."

"You're a fricken nut ... I think I'm going to like you."

She looked up with some hope.

"Really?"

"Yes, really. You keep me entertained with your half-baked plans for the rest of the night, and I'll tell you the condom story."

"Really?"

"You're a dork. Can we go do something before dinner besides have tea?"

"You can't call me a dork, dork. Shit, why do you get me so flustered? That was the worst comeback ever." She got a serious look. "You tell anyone about tonight and you die."

I stood up and put my hand out to her.

"Come here. Your brain is just short circuited. I know how to fix that."

I pulled her into my arms and kissed her. At first, she stood very still and barely kissed me back, but as I ramped up the kiss, she became a willing participant and wow. Just wow! Jennie Wesleyan was no novice to kissing. I could hardly keep up with some of her moves. When we finally broke the kiss, she looked me in the eye and said, "That was your plan?"

"Ah, it was worth a shot. I actually just wanted to kiss you."

"Now, I know why Tami calls you 'stupid boy'."

"Come on, let's go outside and let the cool air clear your mind. I need you coherent if I am going to seduce you and your sister at the same time."

She didn't even respond. She took my hand and led me outside. We walked the grounds and talked. She cornered me a couple of times and reminded me that she knew how to kiss. I think kissing was a great way to get to know someone.


By the time we got back for our reservation, Jennie was herself. When we get to the main dining room, we found that it was just going to be Jennie's sister Carol and her boyfriend Tom. Carol was a freshman in college where she met Tom. She could be Jennie's twin except her hips were a little bigger.

Tom was a skinny guy who clearly had to be the center of everything. He was a junior studying pre-law. He took an instant dislike to me when he caught Carol eyeing me as we walked to our table. Jennie also caught the look, and we glanced at each other as if to say, 'game on'. When we sat down, Tom tried to assert his dominance.

"Let's get a bottle of champagne and get the sampler appetizer. Then we will get the cowboy rib eye with creamed spinach and garlic mashed potatoes."

The girls looked at him as if he was insane, but neither said anything. When the waiter came over I said, "I think we will be adventurous tonight. Tell the chef to plan a meal for the table. Let him know that Carol and Jennie Wesleyan always love his cooking and are looking for him to surprise us."

Tom's face went scarlet.

"But I thought we agreed."

Carol put her hand on his arm to get his attention.

"David has it right. That sounds like fun." She turned to the waiter. "Two of us are under age. Please get them some sparkling cider, and we will have some champagne."

Tom was sulking so Jennie launched the next attack. Unfortunately, it was directed at me. She was just evil enough to turn me on.

"So David, my sister is a huge Kentucky fan. Tell her the story about your recruiting visit and the funny thing with the condoms."

I gave her a look for just a second. I could see her satisfaction in trapping me into telling her what she wanted to know. If she kept it up, I would have to punish her later. I was not sure who would enjoy that more.

"Wait! Are you being recruited by Kentucky? What position do you play?" Carol asked, totally ignoring Tom.

"I received an offer to play quarterback on my visit in September. I originally was there to do a workout for the University of Florida, but when Kentucky found out, they wanted to watch it also."

"What is your last name?" Carol asked.

"Dawson."

"Do you know who this is?" she asked, turning to Jennie.

Jennie gave her a blank look.

"What are you talking about?"

"This is Superman."

I shrugged when Jennie gave me a look.

"I told you I had super powers. I even had your uncle confirm it. Yet, you still doubt me."

I gave her a dramatic sigh. She gave me a look that would have me keeping my guard up all night.

"Bullshit. You're just a kid. There is no way Kentucky would waste a scholarship on the likes of you," Tom said, getting his wind back.

I think it was about time he and I headed out to the parking lot. Instead, I decided to shut him up - without punching him. I pulled out my cell phone and opened my Dropbox app. I scrolled down until I found the scan of the offer letter and brought it up. I handed the phone to Carol.

"Tom, you need to apologize to David."

She showed him the offer. He got up and stormed out. Jennie had a hard time containing her joy, but I gave her a look to cool it. Carol was not exactly happy that her date walked out on her.

"Here, give me the phone, and I'll show you what Carol is talking about."

I brought up the YouTube video and played it. Jennie's eyes were wide when it was done.

"I thought you played quarterback?" She said.

"I do, but I started the season at fullback."

Carol snatched my phone out of my hand. She pulled up the quarterback rankings on Scouts. Even with a week off, I was still the number nine freshman prospect.

"Look at this, Sis. Your date tonight could play in the NFL someday. Click on the link and look at who is recruiting him."

She read the list and then asked, "Are you seriously considering Kentucky?"

"Look at the list and see who has actually offered," I told her.

"I see Kentucky and State, but are these other schools interested?"

"Yes, but I'm just a freshman. The big boys are not about to take a flyer on me. Scholarships are usually too valuable to be handing out offers to freshman but Kentucky has actually made an offer. I want to play football at the next level, so I'm taking their offer very seriously. They were the ones that made the first offer. I have to respect them for that."

The waiter came to the table with our drinks. Carol explained that there would only be the three of us. The food was out of this world. For an appetizer, the chef did tuna three ways. The only tuna I had ever had was out of a can. It melted in my mouth. For the main course, the chef did a rack of lamb with glazed baby carrots, roasted Brussels sprouts, and au gratin potatoes. For dessert, we had a hot vanilla soufflé that was amazing. It was the best meal I had ever had and the girls both loved it.

After dinner, we sat around and talked. People at the club came by and spent time talking to Carol and Jennie. You could tell people genuinely liked them. The girls enjoyed embarrassing me in front of the Kentucky fans that stopped by.

After dinner, we all went to the ballroom where a band was playing. They had a table reserved for their family. Carol saw some of her college friends and invited them to sit with us. I found myself sitting with seven girls. I was happy that Jennie laid claim to me, keeping Carol's friends at bay. A slow song came on, and I asked Jennie to dance.

I slid my hands under her jacket and rested them on her back right above her skirt. She put her hands around my neck.

"Thank you for tonight. I appreciate you being a gentleman."

"I was told that I had to be on my best behavior."

"I hope that wasn't on my account."

"No, I have gone through some girl related issues over the last few weeks. Tami wants me to go out and have fun without the pressure of a relationship."

"Are you saying you are not interested in me?"

That one took me by surprise.

"To be honest, I hadn't thought about it." I could tell that was the wrong thing to say so I tried to recover. "It is not you ... that came out wrong and sounds horrible. Let's just tell it like it is. I am a 'stupid boy' at times and as such, I act like a jerk. Jennie, if I took two seconds to think about it, I would want to go out with you. As a matter of fact, I would love to see you again."

"Nice save. I ... shit."

I felt someone tap me on the shoulder.

"Do you mind if I cut in?"

I turned to find Mr. California, Mark. I remembered his dad's advice and looked at Jennie. She gave me a slight nod, and I allowed Mark to take her in his arms. I walked back to the table and sat down. I was trying to decide if I was pissed or not. I watched their body language, and Jennie did not look comfortable. Mark tried to move closer a couple of times, and she moved back keeping her distance. She was not saying a word to him, and I could see that Mark was talking and glancing over at me.

It looked like Mark said something that pissed Jennie off. She stormed off of the dance floor and went to the women's bathroom. After a while, I looked around and Mark was also missing. At midnight, the band quit playing and everyone was leaving. It was starting to look like I had been stood up. Carol and her friends left earlier so I didn't know anyone, and I was an hour from home. I walked out front to see if the driver was there. I was truly stranded. It was now 12:30.

I didn't have Jennie's cell number. I then called Tami, but she wasn't picking up so I left her a voice mail letting her know what was going on. Crap!

I finally gave up and called Greg. Of course, he had been drinking and I could tell he was in no shape to come and get me. I talked to one of the valets, and he agreed to take me to a motel not far from the club. Luckily, I had enough cash to get a room for the night.

I went to sleep vowing to take a break from dating. I was really having a good time tonight until Jennie disappeared.


Sunday October 27, 2013 – Freshman Year

Tami made the mistake of waking me up Sunday morning.

"David, I just got your message. Are you pulling my leg?"

"Fuck you, Tami. Why would I lie about this?" I hung up.

Okay, it wasn't the smartest thing to do, but I was mad. I looked at the time, and it was 8:00 am. I called home and Mom answered.

"Hey Mom, we may need to skip church today. I'm over an hour from home, and I need a ride."

"Do I even want to know?"

"It's not that bad. Tami set me up on a date, and the girl got pissed at someone else. She stormed out, leaving me to fend for myself. I called Greg last night, but he had been drinking so I didn't even tell him I needed a ride. I got a motel room and waited till this morning to call you."

I saw that Tami was trying to call. I just ignored it. I gave Mom my address, and she said she and Dad would come get me. I hated that they were going to kill their Sunday morning bailing me out. I couldn't wait till my sixteenth birthday when I would be able to drive myself.

I cooled down and listened to Tami's voice mail. It asked me to call her. She knew me well enough that when I got mad, I got over it pretty quickly. So she learned to let me work through it and not to bother me. I dialed her number.

"Hey."

"David, I'm sorry. I thought you were joking around. I have a call into Jennie to find out what happened. So how did you get home?"

"Who said I was home?"

"Oh crap! Where did you spend the night?"

"You know what, Tami? Can we drop it? The more I talk about it, the madder I get."

"Sorry."

"Look, it's not your fault. I think I learned my lesson last night. I've been treated like a fucking afterthought by the last four girls I've gone out with. I'm done. Don't set me up on any more dates, and don't bother bringing anyone home for Thanksgiving."

It wasn't up to me to decide if she brought friends home.

"Well you can bring friends home, but don't expect me to go on a date with them."

"I don't blame you. What do you want me to do about Jennie?"

"Nothing! Your scholarship is in place because of her uncle. I have seen how much her family's wealth influences people around here. I imagine it is ten times worse at Wesleyan. I don't want you to be hurt by any of this. If anyone asks, I had a great time."

"What should I tell everyone about you not dating? You do know that they are lining up wanting to go out with you, many for the wrong reasons. I thought Jennie had it together and was self-confident enough to be a good match, but I need to tell them something."

"I figured. Tell them I'm slammed with football and need to focus on that right now. I know that not everyone is a self-centered bitch at your school, and I would hate to ruin it for everyone else, but I can't handle this right now. Maybe by Christmas, I'll be in a better frame of mind."

"David, I'm still shocked that Jennie stranded you. It's just not like her. I actually like her a lot. It's going to be hard for me not to say anything. But if you say I can't, I won't."

"Tami, I trust your judgment. I also don't want you losing a friend over this. I know you have worked hard to fit in. You know that I love you and only want what is best for you. You decide."

"I will make this up to you."

I could tell that Tami was shaken. She obviously liked and trusted Jennie.

"Hey, you know me better than that. No make-up is required. I know you didn't do this to be mean. I'm either having the worst run of luck with girls, or I have a kick me sign on my back."

We spent the next few minutes talking, but she needed to go to breakfast with her suite mates so we hung up. Thirty minutes later Mom and Dad showed up, and we hit a local diner for breakfast. When we took our seats, I noticed Jennie and Mark were at a table near the back. She saw me and looked confused. She got up and came to our table.

"Where did you go last night?"

What was she talking about? I just ignored her question.

"Jennie, I would like you to meet my Mom and Dad. They drove up to get me this morning after you left me stranded."

"Mark said..." Something dawned on her. I saw her go from confused to beet red as she stormed over to their table. We could hear her screaming at him. I saw his dad come from the bathroom, and she was screaming at him too. She put her hand out and Mark's dad gave her his keys. I heard Mark yell, "How are we supposed to get home!"

"You didn't seem to mind stranding my date last night! You told me he left with that slut, Kelly! You can walk back to California for all I care!"

My Mom looked at me with a straight face and said, "I think I like her."

"Careful, David, if your Mom starts to approve of your girlfriends, something is wrong," Dad chuckled.

"Dad, Mom only has my best interest at heart."

Both of my parents were laughing at that.

I saw all three of them heading our way. Mark's Dad was the first to speak.

"Mr. and Mrs. Dawson, I'm so sorry you had to come get your son this morning. David, may I ask where you stayed last night?"

"I got one of the valets to take me to a motel. Luckily, I had enough cash on me to get a room."

I could see all three of them go stiff at the news. Mark looked like he was going to be sick. Mark's dad put his hand out, and Mark gave him his wallet. There was a wad of cash inside it. I never saw a high school kid with that much money.

His Dad counted out stacks of money. Mark had about $500 on him.

"Okay, David, will a $100 cover the room cost?" his Dad asked.

I just nodded. It actually cost me $60, but I wasn't arguing.

"Mr. Dawson, you have gas, food and you and your wife's time. Here is $250."

He turned to his son.

"That leaves $150 for bus fare back to your Mom's."

I could see tears forming in Mark's eyes. He ran out of the diner before he really started to cry. His Dad followed him out. Jennie pulled up a seat and joined us. Our waitress hurried up and served us. She looked nervous, and I'm sure she was waiting on Jennie to erupt. She also had Jennie's tab, which she slid onto the table and then made herself scarce.

My Mom was not fazed.

"So, Tami suckered you into going on a date with David."

My mother caught Jennie off guard, and she laughed. She soon had tears running down her face and was having trouble catching her breath. It was what we all needed. You could feel the tension leaving the diner.

"Actually, I think David was the one who got suckered. The first thing I asked him to do was to hit on my sister."

Mom arched her eyebrows.

"Really? I bet he did it too."

"You would win that bet. He was smooth. He had her now ex-boyfriend so flustered he didn't even make it to appetizers. Hell, he had me so flustered that he told me that kissing him would clear my head and I believed him."

It was my Dad's turn to lose it.

"Oh God, he did not."

"Oh yeah, he did. Then he said something like 'Well it was worth a try'. When I see Tami, I'm going to have to tell her he is not a 'stupid boy'. He makes the girls around him stupid. I can't believe I fell for it."

"Quit your whining. I didn't hear any complaints," I said, needing to defend myself.

"I'm not complaining about the kissing. I'm kicking myself for falling for your charm."

"Your charm was always safe with me."

My Mom smacked me.

"Quit hitting on her. I like this one. You will be nice, or you will answer to me."

It was Jennie's turn to pop her eyebrows.

"I don't know if you realize what high praise you just received. I can't remember my Mom ever saying she liked one of my or my brother's girlfriends. And just so you know, my brother is a slut, so we are talking about a lot of girls," I smirked.

My Dad nodded. Jennie took it in stride.

"So, you're not mad at me?"

I thought about what I learned about Mark and decided I was not mad at her, but that didn't mean I was dating for a while.

"No, but you did get me to swear off dating for now."

Both my Mom and Dad rolled their eyes. Jennie got pensive and we took a break in the conversation to eat.

"Would it be okay if I took David home?" Jennie asked when we were done and ready to go.

My Mom broke out in a huge smile.

"I was hoping you were going to offer. I didn't want to be around him while he pouted. He can be such a baby."

For whatever reason, Mom liked her. I stood up and took Jennie's hand in mine. We went to the cashier, and she paid her bill. Dad followed suit. When we got outside, Mark and his Dad were sitting on a bench. I walked up and said, "Come on. We'll give you a ride home."

Jennie looked like she was going to object but deferred to my judgment. When we got into the Lincoln, I told Jennie, "I better call Tami. I told her not to lynch you, but she doesn't always listen to me."

Jennie eyes got big.

"Thanks. She likes you a lot, and I would be dead meat if she thought I hurt you."

I dialed and she picked up on the first ring.

"Hey, I'm with Jennie. You can call off the dogs."

"Did she know you were stranded?"

"No, her driver's son thought it would be a good idea to tell her that I had gone off with the town slut. He also thought it was perfectly fine to leave a fifteen year old boy to the elements in 40 degree weather."

"That is not true!" Mark yelled.

 
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