Stupid Boy - Sophomore Year - Cover

Stupid Boy - Sophomore Year

Copyright© 2015 by G Younger

Chapter 16: Holidays

Coming of Age Sex Story: Chapter 16: Holidays - David Dawson is living the high school dream -- brilliant student, captain of the football team, beautiful girlfriends -- when his world is turned inside out when his best friends leave for college and a new football coach wants his son to now lead the team. Find out how David overcomes new challenges and makes new acquaintances as he strives to make it through his Sophomore Year. This is the third in the continuing award winning series Stupid Boy. Nominated for 2016 Clitoride Award.

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   Slow  

Wednesday December 23

I was kissed awake.

"You're so cute when you sleep," Nancy said as she ran her fingers through my hair.

I looked at the clock. There was an hour before my alarm was to go off. I grinned, having an idea why she had awakened me.

"Good morning, Sunshine. Why are you so happy this morning?"

"Because my man was so good to me last night I couldn't see sending him off to the salt mines without a little loving," she almost purred.

I rewarded her by giving her a deep soulful kiss. Nancy grasped my member and saw I was nearly ready. When she was satisfied, she grabbed a condom and put it on me. I looked into Nancy's eyes as she straddled my waist, and slowly sank down. She kept eye contact as she lowered herself and a wicked little smile lit up her face. I let her ride me as I wet two fingers and then reached down and stimulated her clit. She raised her eyebrows as I played with her pussy. Nancy's body started to give me clues of her increasing arousal. Her nipples started to extend, her breathing got deeper, and her neck and upper chest became flushed.

I watched as Nancy's first orgasm found her biting her lower lip accompanied with a sharp intake of breath. Then she held it. I could feel her whole body quiver as her eyes snapped shut, and she let out a long moan. When she started to come down, she opened her eyes and gave me a predatory grin. Nancy and I seemed to take turns as to who was dominant. This morning was her turn.

She pinned my hands above my head, and leaned down and kissed me. Her hips were starting to turn so we weren't at the greatest angle. I solved the problem by scooting my feet back, so I could fuck her better. I grasped her hips and guided them, so we could enjoy our coupling to its fullest. Nancy was kissing my neck and pecs.

The only thing that distracted me ... was that damned clock! I didn't want our morning session to interfere with my work. I finally had to call it quits and run for the shower. When I came out, Nancy had a satisfied look on her face as she was lightly snoring. I envied her being able to go back to sleep. I thought about smacking her butt. I was surprised when Mr. Happy rejected the idea, because he felt we could have more fun, later.

I quietly made my exit, to find Kendal and Tiffany sitting in the kitchen smiling at me. I ignored them and grabbed some poached chicken Devin's chef had left for me, so I nuked it in the microwave. I found a head of lettuce to make a salad for breakfast. While the chicken was finishing up, I made my protein shake, and readied my supplements. I planned on taking full advantage of Devin's gym, once I was done with my shoot later.

We would be working at the ranch, today. When I was done with breakfast, Tiffany led me over to the barn, while Kendal went to the house. I found Bev and saw that they had a makeup/wardrobe trailer. Bev sent me in to get ready. I was surprised when Dad and Uncle John walked in.

"What are you guys doing here?" I asked.

"Devin talked us into being in the shoot," Uncle John said.

Greg came in a moment later, carrying Kyle. It looked like all the boys were going to be rugged outdoorsmen today. The shoot was supposed to be camping/hunting gear. Range Sports was big on families and outdoor activities. It made sense a family would make good ad copy.

When we were done, I couldn't help smile when I saw Kyle and Greg in matching camo gear. Dad, Uncle John, and I, all had different patterns. I came out of the trailer to find all our women had joined us. They had been made up in the house.

"Notice anything," Bev teased me.

It took me a minute, but then I saw each family group was in matching camo gear including Nancy matching me. Bev took all of us out behind the barn, and I saw they had a camp scene setup. The whole group got together to take the first shots. I wasn't surprised when Devin and Sandy joined us. Then they took pictures of just my family. I was planning on adding this one to my photo wall, in my apartment.

Since it was chilly out, they did Greg and his family next. They had them put Kyle and Mac down on the ground, and Greg and Angie kneeled behind them. As if on cue, a litter of lab puppies came bounding out of the barn. Kyle and Mac were bowled over by the excited pups and there was some squawking which quickly became peals of giggles as the puppies licked them. Bev was working hard to capture the chaos which ensued. Kyle lost his hat and two proud puppies pranced off with their prize. Mac had a wiggling bundle in a death grip, but Angie was quick to the rescue and saved the puppy.

I was nudged, and looked down to find a big guy wagging his tail and wanting some attention. The mother checked her pups, and then came over for some loving, too. Nancy and I loved on the big dogs, and then the puppies came bounding over and wanted to play with their mom and dad. Greg and Angie brought over Kyle and Mac. I lay down so they could drop them on me. I soon had squirming babies and puppies crawling all over me.

Angie decided since I was defenseless, I should get snow in my face. Mom and Bonnie grabbed babies and a giant snowball fight erupted. I had to laugh when Greg stuffed snow down Dad's back. Devin and Sandy joined in on the fun. I noticed Bev had a big grin on her face as she was getting the action captured. I nudged Greg and we both threw snowballs at her at the same time. The picture turned out to be a great shot as she caught both snowballs flying at her and us grinning like idiots.

Bev said she had enough pictures. I noticed Mom, Bonnie, Kendal and Tiffany had managed to stay out of the snowball fight. I guess they were just smarter than us. Everyone except me got to go and have fun the rest of the day. Bev made me ride several different snowmobiles. I was surprisingly okay with the turn of events.

I was happy when Bev finally said I was done. I was wet, cold and tired when the day finally ended. I went back to the bunkhouse, and got into the hot tub to warm up. I put on some music and took a nap, as the jets and hot water did their magic.


I was startled awake when Nancy found me, and gave me a kiss.

"You need to get out. You've turned into a prune," she advised me.

She took me back to our room and sent me to the shower. When I came out, she was relaxing by the fire in the great room. She patted the seat next to her on the couch. I joined her and she snuggled up to me.

"Did Kendal and Tiffany already leave?" I asked.

"Yeah, they wanted to get home to spend Christmas with their families. You just missed them."

"Dang it, I wanted to thank them for helping me out the last few days."

We let the conversation lull. We were both in our own thoughts. I was wondering what to do about Devin and Nancy. I was trying very hard not to get mad, but I was a losing proposition. I was surprised I wasn't really mad at Nancy. We had never made any kind of official commitment to each other, but I had flown her out so we could get to know each other, to see if there was something between us. When I had decided to date Peggy, I'd made a point to call Nancy and tell her. She'd told me it was okay, because we were just friends. My problem was if she and I were exploring our possible compatibility, why was she letting Devin hit on her. I guess I was a little mad at Nancy. I felt she should at least tell me if she really did have feelings for Devin.

If it wasn't for Devin, I would absolutely say I liked Nancy a lot. The only thing holding me back was the four years age difference. I know it doesn't sound like a lot, but at this point in our lives it might as well have been twenty years.

Devin was another matter. He knew I would not try and snake his girlfriend. If I were that kind of guy, I would have bedded Lana in either the UK or San Francisco. He trusted me enough to put me right in the middle of his little sting operation to prove Lana wasn't going to be faithful to him. I was very uncomfortable when it happened, because of my strong beliefs regarding my feelings concerning dating someone else's girlfriend. Tracy, in two of her bat crazy moments, had deliberately hurt me by jumping in bed with another guy. I knew how much cheating hurt.

If Devin was honorable he wouldn't have put on his little display last night. Dancing with Nancy all night had even made his longtime friend, who agreed to be his date, mad. If her talking to him didn't make him back off ... then he wasn't the friend I thought he was. He should at least be man enough to talk to me about it. I was a little sad Mom had pointed out what was going on. I'd lost a lot of respect for Devin over the last day. I wondered if I should initiate the conversation with Devin before we damaged our relationship so much I couldn't work with him anymore.

I decided to talk to Nancy about it when she interrupted my thoughts.

"Can just the two of us go out tonight? I would like some alone time with you," she said.

"Of course we can."

She let out a long breath and smiled at me. Maybe I had been reading too much into this. I sure hoped so.


I was getting ready to take Nancy out when my phone rang. I could tell it was Tami by the ring tone, Cryin by Aerosmith.

I was cryin' when I met you
Now I'm tryin' to forget you
Your love is sweet misery

"I am so mad at my mom," Tami launched right in.

"Why would you be mad at your mom?" I asked.

I thought it was a reasonable question. Apparently it was not.

"Don't give me any of your crap. You know good and well what is going on. You can't tell me Alan or someone else is not keeping you in the loop," she accused me.

"Okay," I said cautiously.

"What should I do about it?" she asked.

I froze trying to think what Tami and her mom could be fighting about. Then it hit me. It had to be Simon. This was the last fight I wanted to get into the middle of. Anything I said would end up being wrong and only drive a wedge deeper between us. If I sided with her mom I was trying to break her and Simon up. If I sided with her I was being spineless and just agreeing with her. I had seen this played out before in different variations.

"Can I ask a couple of questions?"

"If they're not stupid," she shot back.

"I don't know if they are stupid or not. If they are can we keep the name calling to a minimum?"

"Go ahead."

I could imagine her fuming and tapping her foot with impatience. I tried not to chuckle. I found it was one of the top three worst responses. It ranked up there with telling her what I really thought and the absolute worst ... telling her she was wrong. I found the Dawson Cone of Silence was usually my best fallback position. I have no idea why I tried to be reasonable.

"Do you understand where your mother is coming from?"

"Yes."

"Does she understand where you are coming from?"

"Yes."

"Do you see where there might be a chance for a compromise?"

"No."

"Okay, this sounds serious. Is anyone else involved?"

"You know there is."

"Are they willing to let this damage your relationship with your mom?"

I was hoping this had to do with Simon staying at the hotel.

"Yes."

"Really?" I asked surprised.

"Yes."

"Are you willing to damage your relationship with your mom over this?"

"Yes."

"There you have it then. Do whatever you want then. If you don't care what your mom thinks, then have at it. Don't be surprised when you get grounded," I offered.

"But..."

"Tami, you just said it. You don't care if you hurt your mom. It actually makes me sad to hear you would allow this to happen, but I know you and only you can make up your mind."

"You haven't helped with this at all," she complained.

"What did you expect me to do?" I asked.

"Call my mom and talk some sense into her," she answered.

"Hell no! I am not getting in the middle of this with your mom. Besides I have no idea what is going on."

"You seriously haven't talked to your mom?"

"Tami, Mom doesn't tell me what is happening in your life."

"Oh. Simon..."

"Stop! Do not make me get involved in this. I'll make one observation before I hang up. If he is willing to push an issue so far it damages your relationship with your mom, I don't think he is a very nice guy. I would look at this very hard. I personally would never allow someone, I was just dating, to get between me and my family. You need to think about how this will hurt your mom. I bet if you really thought about it you would agree with me."

"You just don't like Simon, no one does."

Again, I almost chuckled. She sounded like she was ten years old throwing a tantrum.

"I don't even know him, so I don't know where you get off passing judgment about how much I like or dislike Simon. And if no one likes him ... you might want to figure out why. Your friends would never tell you they didn't like your guy unless they felt strongly about it. We all love and support you. I think if you are not careful you might end up damaging more than just your relationship with your mom over this."

She hung up on me. I counted that as a victory. This went way better than I expected.


Nancy and I went to an upscale restaurant for dinner. It gave her a chance to dress up and wear the earrings Devin had given her. The earrings irritated me, but she looked good in them. I had brought some nice clothes in anticipation of my trip to LA. They sat us in a dark corner, in a wraparound booth. Nancy was in a playful mood and snuggled up next to me. I felt her hand teasing my thigh.

"So now that you're done working, what's the plan?" Nancy asked me.

"Tomorrow is Christmas Eve. I've talked with the chef, and he is letting me cook the meal. If you'd like to help, I would enjoy the company."

"What are you making?"

"Tracy's grandfather used to own restaurants. Her mother has been using his recipes and teaching me to cook. She gave me an idea for a rib roast. Mom and Angie are going to make desserts, and Bonnie is baking bread."

"Could I make my mom's broccoli casserole?" Nancy asked.

"That sounds good. I was thinking about doing mushrooms as a side dish, because I know Greg and Dad love them. I need to figure out some kind of potato."

"I like horseradish sauce with rib roast."

"Do you know how to make it?" I asked.

"No, but I'll bet we can find a recipe online."

I could see her getting excited about working together on making the meal. I was a little nervous about making the rib roast, but Mary Dole had promised me her recipe was foolproof. I hoped so, because a rib roast wasn't cheap. I had asked Mary for an idea to wow my family and she immediately suggested it. She said for a special occasion it was perfect.

The restaurant featured French Cuisine. For an appetizer we had a cheese/fruit/nut tray and Nancy ordered a tasting flight of different French wines. For the main course we had lamb chops with baby carrots. I had never tried lamb before, and really enjoyed it. For dessert, we had crème brûlée.

Over dessert and coffee, Nancy got a serious look on her face.

"I don't know if you've noticed anything ... I know your mom has ... I ... ah," Nancy said hesitantly.

I reached over and took her hand.

"I can tell you're uncomfortable. I find it best to just to say it," I suggested.

"Your family loves you very much. Your mom and I had a long talk yesterday. She actually told me if I didn't stop acting like a lawyer she was going to put me over her knee," Nancy said with a smile.

I knew my mom well enough to know she would do just that.

"That would be my mom. I take it she grilled you."

"More like, she knocked some sense into me. I need to start from the beginning."

For some reason, I wasn't nervous about our talk. She wasn't giving off the vibe she was going to dump me. I was getting more of a nervous vibe, like she needed to confess.

"Devin has been showing me around while you were working. I have to say he is a wonderful guy, and he thinks the world of you. At times, I think he wishes he was you. He has been a perfect gentleman, but... ," she paused and looked me in the eye. "Something changed, the other day. You know being in a sorority, I get hit on a lot. I recognize when a guy likes me more than just friends."

She let it sink in before continuing.

"I totally missed that Devin was interested. He is a really nice guy who has many things I'm looking for in a long-term relationship. He is driven and successful. I understand he inherited the business, but he has taken it to a whole different level. I'm attracted to men who are self-assured and know what they want in life. I think that is why I'm not interested in most college guys.

"I look at his lifestyle and see what the trappings of wealth bring. This ranch is the ideal setting for raising a family. If I were to get into a long-term commitment with him, we would have to get a winter place where it's warm. I don't think I could handle the winters here."

"So you're thinking of marrying the guy?" I teased.

"If you don't treat me right, I might," she shot back.

I just raised my eyebrows.

"Quit interrupting me. I think Devin would be the perfect guy for me except for one thing," she said.

I waited for her to finish, but I could see she wanted to say it correctly.

"I think I have gotten to know you. My talk with your mom helped me understand you better. My concern is I don't want to be the reason you and Devin are no longer friends. Your mom suggested I tell you, because if we allow this to continue, it will only get worse. Devin has made inappropriate advances on me."

It didn't sound like she was falling for Devin, but I was not happy to hear her confirm he was interested in her. She rushed on before I could comment.

"Devin is someone I could never date. The reason I say that, is because he has gotten serious in pursuing me. The night we went dancing he actually propositioned me. I think his problem is, he has very little experience dating. College may have done him a world of good.

"However, I also absolutely can't stand a guy who goes after someone he knows is taken. You and I are just good friends, but Devin knew I was here to be with you. To be honest, if Devin hadn't pushed me to sleep with him, I might have fallen for him in the long run if we had a chance to be friends."

"You said Mom knocked some sense into you?" I asked.

"We had a long talk. I didn't want her to see that Devin was making a fool of me. I knew as soon as I felt guilty talking to your mom, I was jeopardizing our friendship. Devin Range is not worth me losing you as a friend. What your mom did was help me focus on what mattered."

I sat quietly taking in Nancy's comments. Dad always said it wasn't that a person made a mistake, because they will. It was how they handled it. Did they blame others and not accept responsibility, or did they man up? Nancy had just admitted she misread Devin's friendship. He had made direct advances. I was happy to see she was handling this well.

The more I heard, the madder I got at Devin. If he wasn't my boss, I would kick his ass. In high school a good ass kicking would get the bad blood out of the way, and maybe we could be friends again. In the real world, it was frowned upon. What a pity that was the current attitude. I was afraid I couldn't work with him anymore. The other problem was I had my whole family here staying in his house for a vacation. If I kicked his ass, we might have to find other accommodations. I would bet my family would be fine, but I didn't want them to have to deal with this on vacation.

"David, nothing is going to happen with me and Devin. I want you to know, though, that someday I might find the right guy. For now, I really like what we have. You are a good guy who is going places. After meeting your mom and spending some time around her, I understand how you stood up to me this summer. I could learn a lot from your mom."

I laughed.

"Please don't," I begged.

"I want to make a suggestion, talk to Sandy. I think the two of you can make things work; at least from a business standpoint. If I know you, you will have a problem working with Devin after this. I would also like to not be left alone with him the rest of the trip. I came here to spend time with you, and to get to know your family. I would very much like to do that."

"My family and I would like to get to know you better, also."

I was going to have to give my mom a hug when I saw her next. I was feeling much better about Nancy. Devin, not so much...


We came back to the bunkhouse, to find the lights low in the great room. There was a fire and mood music. I caught some movement by the fireplace and I saw Greg and Angie had just finished having sex. They hadn't heard us. I grabbed Nancy's hand and led her in. She made a little gasp that gave us away.

"Looks like you wore him out," I teased Angie.

I hadn't seen her naked in a while. She had gotten her figure back and was looking very hot.

"David, give them their privacy," Nancy said acting concerned.

"Honey, these boys are not shy. I have seen that one naked more times than I can count," Angie said pointing at me.

"Join us," Greg offered as he put his boxers back on.

We went to our bedroom.

"I don't know about this... ," Nancy protested.

"It's your call. I know there isn't going to be anything weird. My guess is we will just hang out. If anything sexy happens, we can come back to the room."

"I trust you and your family, and your brother is cute," she said, and dodged me as I tried to swat her butt.

We put on shorts and t-shirts and joined Greg and Angie. Angie had found a robe and the liquor cabinet. She made drinks for everyone. I was sticking with Coke. We had a nice evening. The three of them had a nice buzz by the time we decided to call it a night. Mom had volunteered to watch Kyle and Mac to give Greg and Angie a night of fun.

When we hit the bedroom, I think Nancy felt like she owed me something. She started out by blowing me to take the edge off. Then she shocked me.

"David, I want you to take my last virginity," she said with a smile.

Mr. Happy seemed to know what she meant, as he was a good soldier and came to attention.

"Are you sure?" I asked to make sure.

"Yeah, I have always wanted to, but I was waiting for the right guy. Be gentle," she ordered.

I went down on her to get her ready. I wanted her to have an orgasm and then bring her right to the edge of another one before we tried this. I worked her over bringing up the level of her passion. I reached over to the night stand and found my bottle of lube. I covered my fingers and then began playing with her rosebud as I used my tongue to pleasure her.

When Nancy began to cum, I worked my finger into her. That caused her to have a bigger orgasm than I expected.

"Yes! Do me!" she demanded.

I just kept eating her and getting her ready. It didn't take long for me to get her right to the edge of another orgasm. I grabbed a condom and added lubricant. The last thing I wanted to do was to hurt her. Extra lubricant is a good idea if you are going to do anal. I was surprised when I was able to enter her without any problems.

She took to it like a fish to water. I had always enjoyed it, but it was much more fun with someone who delighted in it as much as I did. She liked it best when I grabbed her hips, and did long, fast strokes. She was screaming my name before too long. You know you're doing something right when a woman does that. I was surprised Angie didn't try to peek in our room while we were going at it. I guessed Greg must have had her occupied.

Nancy had a huge orgasm and collapsed onto the bed. I followed her down, and continued to pound her ass. I was close and she kept cumming until I finally emptied my balls. After we had rested, she was game for more, but I wasn't surprised when she told me her ass was off limits for now.

I think Greg was trying to show me he still had it. I could hear Angie making a racket in the other bedroom. I waited for things to quiet down before I started on Nancy again. We traded off pleasing our women well into the night. It wasn't like I was keeping score or anything, but I won.


Thursday December 24

We went to the main house for breakfast. Angie and Greg had beaten us there. Mom and Bonnie gave me funny looks. It looked like Angie had been talking. The chef was serving just about anything you wanted. I had a huge plate of scrambled eggs, with a side of smoked ham. Sandy and Devin joined us, and I noticed Devin wouldn't look me in the eye.

He announced he was going in to work, to give out bonuses. The rest of us were free to go do what we wanted. We decided we would go snowboarding in the morning and then come back and start preparing for Christmas Eve.

Sandy drove one of the vans, and Dad drove the SUV I rented. We ended up at a resort I had not been to yet. Sandy promised they had great snowboarding runs. This was one of the older resorts and had a more intimate feel than the new super resorts. Sandy had lift passes waiting for everyone. Range Sports had a block of passes for when people came into town on business, or as rewards for their employees. Angie and Greg took Kyle and Mac to the daycare. Soon everyone was on the slopes.

I had just finished my first run when Sandy cornered me.

"Come with me," she ordered.

I followed her into the resort and we went and got hot chocolate. The view of the hill was fantastic, as we relaxed.

"Okay, spill it, what is going on with you and Devin?" Sandy asked.

I wasn't sure what I should say. I didn't think I should complain about him trying to steal my girl when she wasn't technically my girl. I decided to play dumb.

"What are you talking about?" I asked.

I don't know how they do it, but girls can always tell when you are bullshitting them. She gave me an exasperated sigh.

"Something's up? Hell, Devin wouldn't even look you in the eye this morning. I know he did something, because it's how he acts. So just tell me, because I can tell you're not happy with him," she ordered.

"I'm not sure I should tell you this," I confessed. "I think everyone would be better off, just letting it go."

"Except neither of you will recover from this, if it continues."

She was giving me a hard look.

"If I tell you something, will you keep it to yourself?" I asked.

"Only if it makes sense," she told me. "Now tell me."

"Devin has made unwanted advances on Nancy."

Sandy sat forward in her chair. I could tell she was getting mad, and I didn't need her going off on her brother in this kind of mood.

"What do you think of all this?" was her opening question.

"I'm pissed at Devin, obviously. Nancy came to me and explained what was going on. My mom clued me in, the other day, and she also talked to Nancy. Nancy doesn't want to be left alone with him, but she is also worried this will ruin Devin's and my friendship."

"He has really put everyone in a bad position. I suspect he'll try and deny it," Sandy said.

"If he does, you need to have a serious heart-to-heart with him. If Devin starts lying about things, eventually everyone will know that is what he is. I would hate to think of him as not being someone I could trust," I said.

"Doesn't everyone tell lies?" Sandy asked.

"Maybe, but it is a character issue. Are you a man of your word or not? I've never known Devin to lie, but I never expected he would try and get into my guest's pants either."

Sandy pondered what I had said. She got up and grabbed my hand.

"Come on, we need to talk to Devin," she said making it clear I had no choice in the matter.


When we pulled into the Range Sports parking lot, Sandy could see the confusion on my face.

"Thought it would be bigger?" she asked

I just nodded. I was looking at a nice three story office building.

"Park City makes a great place for a corporate headquarters, but it is a terrible location to manufacture anything. The shipping logistics out here would be a nightmare," she said as I began to understand. "We do have Marketing, Accounting, our phone banks, the IT Department and then Upper Management all in this building. About a half mile from here, we have our Research and Development team."

She was explaining this as we walked in. She led me towards the back of the building to the cafeteria. It was all decked out for the holidays. There was a large group of women in goofy Christmas sweaters. I think they were trying to see who had the worst one. Sandy walked over and she was suddenly in the center of the conversation they were having. She introduced me to the group and I turned on the Dawson charm and talked to all of them.

After fifteen minutes, Sandy saved me. She then led me through the building. It seemed none of the departments were working very hard. I was confused how everyone seemed to know me, so I finally asked Sandy about it. She then pointed at one of the walls. Sure enough, there was my picture. It seemed they had my pictures throughout the building.

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