Senior Year at Sommerville High

All characters are 18+

CHARACTER GUIDE

Jake - He is the main character. An Italian with olive skin, brown hair, and blue eyes. He's fit with a flat stomach, toned arms, and chest.

Sydney - Blonde and busty, a theatre kid and self-appointed group leader. She loves taking charge and uses her big boobs to her advantage.

Zoe - A near Zendaya clone except curvier, though not by much. She is artistic and generally keeps her walls up.

Ray - Well-mannered and the school's star athlete. He puts others before him whenever he can. He is a black teenager who looks like a pro athlete already.

Danielle(Dani) - Jake's older sister who graduated from college but moved back home, where she works remotely.

Stella Rosati - Jake and Dani's mother.

Andrew Rosati - Jake and Dani's father.

Mrs.Augustyne - Sydney's mother. She looks like a mature version of Sydney with the same dirty blonde hair and a large bust.

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NEW YEAR'S EVE

I woke up early in the morning, and in what had become part of my morning ritual, I took care of my morning wood using the pictures of my mom and sister.

After taking care of that, I headed to the bathroom to finish the rest of my routine.

We planned on leaving at noon, and I wanted to check that I had packed everything I needed for the trip.

As I was checking, someone knocked on my door. I turned around to see that it was Dani.

"Good morning," I wished her as she entered my room.

"Morning. Are you ready for your trip?"

"Yeah, in the middle of doing a last-minute check. I don't want to forget anything important."

"You know you haven't used your favor for the week."

"Oh, yeah. I've relied on the photos so much that I forgot about our deal."

"Are you up for it now?"

"I jerked off already."

"Oh, come on. You're young. You'll be able to get it up again."

"If you say so."

We both got naked, and I lay on the bed. I generously applied lube, not wanting to chafe my dick.

The first few minutes went by quietly. As I stared at my sister, I thought about the picture of her with a face full of cum.

That made me ask, "Whose cum was it?"

"Huh?"

"In the picture you sent me. Who came on your face?"

"It's none of your business. Now, hurry up."

"I told you I already came in the morning. Why won't you tell me who it is?"

"Fuck this! Sometimes, you need to know when to be grateful for what you have and not push for more."

She picked up her clothes from the floor and stormed out of my room naked. I was scared that Mom or Dad may have seen her leaving my room nude. I checked the hallway, and luckily, neither of them was there.

I put my clothes on and was confused about what had just happened. I needed to apologize, but it would be pointless until she calmed down.

I headed downstairs for breakfast, and Mom was at the table. I got myself a plate of food and sat next to her.

"Good morning, Honey. Are you ready for your trip?"

"Yeah."

"Do you have enough warm clothes? I don't want you to get frostbite or hypothermia when you're up there."

"A little extreme, don't you think, Mom?"

"One can never be too safe."

We had some general conversation, but I was focused on Dani's picture the entire time. I had checked the info on the photo and knew it was from when she was in university. I knew she had one boyfriend at university, but it wasn't serious.

I figured Mom would know more than I did and asked, "Hey, Mom? Did Dani ever tell you about her university life?"

"Uhm, yeah. Why do you ask?"

"I want to know what to expect when I go next year."

"Oh, please, don't remind me. You're off to college, and Dani recently told me she plans to move out. Your Dad and I are going to be empty-nesters."

"You're making this a bigger deal than it is. But, back to Dani. Anything interesting she's told you?"

"Not really. It was your standard college student life. Again, why are you asking? I think you have some other intentions."

"No, I don't. I'm genuinely curious."

I could tell she didn't believe me at all.

Luckily, I was saved by Tyler. He called to let me know that instead of leaving at noon, we moved it up an hour to 11.

It was already 9, and I used that as an excuse to get myself out of the conversation.

I headed upstairs, and before going to my room, I went to Dani's first.

I knocked on her door, but there was no reply. I knocked on her door a few more times before she texted me.

Dani: FUCK OFF!!

She was still angry at me, so I went to my room.

With nothing to do, I decided to head to Sydney's house early. Initially, Dani had agreed to drop me off, but that was off the table. I asked Sydney if I could leave my car at her house while we were away, and she said it was fine.

On a piece of paper, I wrote an apology to Dani and slid it under her door. I loaded my bags into the car and said bye to my parents.

Before leaving, Dad handed me his credit card and some cash, saying, "The credit card is only for emergencies. The money is so that you can pay for what you need and not rely on Sydney."

"Thanks, Dad."

I reached Sydney's house and rang the doorbell. Sydney opened the door to let me in.

I followed her up to her room, where she was still packing.

Typically, I would run into her mom, but I hadn't seen her yet. That made me ask, "Where is everyone?"

"They didn't reach yet. You're the first one.

"No, I meant your family."

"Oh, since I'm going on a trip with you guys, they decided to take a mini trip to Florida."

I was slightly disappointed since I hoped to talk to Mrs.Augustyne and hear more about her sex life.

I was chilling on the recliner in her room while she modeled different outfits to get my opinion.

Seeing her strip down to her bra and panties each time made me hard. It didn't go unnoticed either as she said, "Aww, someone is excited. I wish we could take care of it, but there isn't enough time. Feel free to use my bathroom, though."

"I'm good. Plus, if we had sex again and Matt found out, he'll be even more mad than he is."

"Why? We decide what we want to do."

"Have you talked to or seen him since I told you about the situation?"

"Nope. Today will be the first time talking to him since the school closed for winter break."

"Do you think he'll make a big deal? Oh shit! What if he tells the others."

"So what? We'll handle it, or I will if you don't think you're up for it. Right now, stop worrying about that. Also, please do something about your boner. I'm getting distracted."

I went to the bathroom, but instead of masturbating, I waited for it to go down.

I came back out, and the doorbell rang. Sydney was half-naked, so she asked me to open the door.

Tyler and Soniya were the ones who rang the doorbell. I let them in, and Tyler asked me, "I thought we would be the first ones here."

"I had nothing better to do, so I came here early."

"Where's Sydney?" asked Soniya.

"She's upstairs packing."

Sydney shouted from upstairs, "Who is it?"

"It's Tyler and me," Soniya shouted back.

"I'll be down in a second."

"I better go help her."

"Why? She said she'll be down in a second."

"Yeah, I know what a second means for girls. If we want to leave on time, I better go."

Soniya went upstairs, leaving Tyler and me alone. We decided to raid her snacks as we waited.

Ray was the next to arrive, followed shortly by Zoe. Zoe went upstairs to help Sydney and Soniya while we loaded the cars.

We were taking Mrs.Augustyne's Escalade and Tyler's F-150. Everyone's luggage had been put away except for Matt, who had yet to arrive.

It was 10:55, and we had agreed to meet at Sydney's by at least 10:45.

I asked, "Someone told him we're leaving at 11, right?"

"Yeah. I texted him, and he gave me a thumbs up. Let me call him."

Ray called him, but he never picked up.

It was past 11, and still no sign of Matt.

I asked Sydney discreetly, "Do you think he bailed because he's mad at us?"

"He's not a little kid, Jake. And if he did bail on us, I wouldn't mind because he would've ruined the mood with his bitchy attitude."

She announced, "If Matt doesn't get his ass here in the next 5 minutes, we're leaving without him."

"We can't leave without him. He probably got stuck in traffic or ran into some last-minute problems," Ray pleaded on Matt's behalf.

"He could've let us know he was going to be late. He didn't even pick up his phone when you called him. It's 10 minutes past 11. There's no reason for us to be late because of someone who doesn't even have the courtesy to let us know."

We were nearing the 5-minute deadline Sydney had set when Matt arrived in an Uber.

Sydney furiously walked towards him, but Soniya and Zoe intervened and calmed her down.

Soniya said, "Ty, why don't you help Matt get his stuff in the car, and we can leave?

Sydney said, "Jake, Matt, and me in the Escalade. The rest of you can come in Tyler's truck."

"Are you sure that's a good idea, Sydney? Why not let Matt come with us, and I'll ride with you instead."

"Nope. Jake, Matt, and me in the Escalade. You guys are in the truck."

There was no point in arguing with Sydney once she had made up her mind,

Sydney and Matt got in the Escalade, and before I got in, Zoe said, "Make sure shit doesn't boil over in there."

"I'll try my best."

I got in the driver's seat, Sydney in the passenger seat, and Matt in the back.

I hadn't even turned on the car when Sydney blasted Matt, saying, "What the fuck is wrong with you, Matt? So what if Jake and I had fucked without you. It was never a deal. I never said if I have sex with one of you, I'll have sex with the other. If the roles were reversed, you wouldn't have given a fuck about Jake. You..."

"Sydney! Calm down."

"He made us 15 minutes late because he's childish and can't deal with problems like an adult."

"Relax! Give him a chance to explain. Maybe there was a different reason why he was late."

I waited for Matt to talk, but he sat there with the same stoic expression since he arrived.

Sydney looked at me and said, "Ok, now let me go at him."

Half the car ride was filled with Sydney raging at Matt. But he didn't respond or react at all.

Once she realized she was wasting her breath, she gave up, saying, "This is pointless. I hope you're happy with how immature you are, Matt."

A few minutes of silence later, Matt spoke for the first time. "I'm sorry. I know I was being selfish and immature."

I looked at him through the rearview mirror. He was still expressionless, making me doubt whether he meant it.

The rest of the drive was nothing but awkward silence. I tried making conversation to brighten the mood, but it went nowhere.

The painful car ride ended when we pulled into the cabin.

I got out and looked at where we would stay for the weekend. Zoe came to me and asked, "How bad was it?"

"It was hell. Sydney went psycho the first half of the ride, but Matt didn't respond. He then calmly apologized, and neither said a word since."

She side-hugged me and half-jokingly and half-seriously said, "It's okay. It's all over now."

It was a 3-hour drive, and everyone was starving as we didn't even stop for snacks. After unloading the luggage, we got in the car to find a spot for lunch.

We found a place that had good reviews and placed our order.

Sydney and Matt remained silent the entire time.

Ray had enough of this and said, "Okay, this has gone far enough. This trip cannot be ruined because you two are in bad moods. Do whatever to solve this issue right here, right now."

Sydney and Matt looked at each other. She held out her hand for a handshake, which Matt agreed to.

"I agree to put this behind us while we're here."

"Not just while you're here," said Ray. "For good."

Sydney rolled her eyes and said, "Fine. Let's put this behind us for good."

"Deal," said Matt.

Sydney started talking more, but Matt was still quiet.

After lunch, we debated between going to the cabin or exploring the town. Everyone was tired and wanted to take a nap. But if we took a nap, we might lose a whole day.

We decided to power through the sleepiness and see what the town had to offer.

We planned to find things to do for the rest of our trip when we weren't skiing. There was a Korean restaurant that we all found interesting. There was an arcade with retro games and a hot chocolate cafe. We found other things, too, but these were atop our list.

Not wanting to come to town for dinner, we placed a delivery order at a pizza spot before heading to the cabin.

At the cabin, we needed to decide where everyone would sleep. Sydney took charge of that.

"There are five bedrooms here. Tyler and Soniya have a room. Zoe and I will each have our rooms." She looked at Ray, Matt, and me and said, "Two of you will have to share. How about Jake and Matt?"

Sydney looked at me and mouthed, "Say yes."

"Yeah, I think that's a good idea."

Everyone took their luggage to their rooms to shower and relax.

I unpacked my luggage and waited for my turn in the bathroom that we shared with Zoe.

While waiting, I tried to get Matt to talk.

"Hey, Matt. Are you going to talk at all during this trip? How many times do Sydney and I need to apologize?"

"I'll talk when I feel like it. And for the apologizing, it doesn't change what happened."

I'm a patient guy, but I was getting fed up with how Matt behaved. He acted as if Sydney and he were dating, and she cheated on him with me.

Till now, I felt sorry for him, but it was becoming difficult.

There was a knock on the door, and I thought it was Zoe letting us know she was done with the bathroom.

I opened the door, but instead of Zoe, it was Sydney.

She walked in, closing the door behind her.

"Listen here, Matt," she said. "Your shit mood is ruining the trip for everyone. They don't know what's wrong, but we do. So, I'm here to take care of it."

"What do you mean?" asked Matt.

"You're upset because Jake and I had sex. If I have sex with you, will that even things and make everything better?"

"Uh, uhm, I guess."

"No, I need a definitive yes or no. I'm not going to fuck you if you're still going to be an ass."

"Uh, yes."

"Yes, what?"

"Yes, I won't be an ass."

"Good," as she got on the bed with her knees on either side of him.

"I think I'm going to leave you two alone," I said.

"No, you're not. You're sitting, watching, and not having sex with me. I think that'll make things better for Matt. Right, Matt?"

"Whatever you think is right."

She took off her sweater to reveal a hot pink bra. She leaned down and started to kiss Matt. As they kissed, her hand drifted down to his crotch, rubbing his penis.

She started crawling down, taking his jeans with her as she went down.

Sydney took Matt's cock out of his boxers and gently began to play with it. A strand of spit fell from her lips onto his cock, followed by her licking it from the base to the head. Her tongue circled his mushroom head before entering her mouth.

It got sloppy pretty quick, and she was gagging on his penis. As she was sucking him off, her free hand caressed his balls.

Her attention then shifted to his balls. She started sucking on them one by one while stroking his penis.

He started twitching, and I could tell he was close to cumming. Sydney didn't let him get off that easy. She stopped pleasing him with her mouth, took off her bra, and tossed it in my direction.

They exchanged looks, and Matt mounted her in a flash. He started sucking on her tits and playing with them.

My erection started to feel uncomfortable in my jeans, and I needed to take it out. I was getting myself off to live porn.

Sydney made Matt stop, saying, "Let me get back to giving you head." Her nipples glistened from all the spit. She resumed giving him a blowjob and let him finish in her mouth.

After swallowing the mouthful of cum, she asked, "How do you want to fuck me?"

"Doggy," he answered instantly.

She removed the rest of her clothes and got in doggy style. Matt positioned himself behind her. Before he put his penis in her vagina, he looked at me. He smirked and started fucking her.

It was like he was bragging about having sex with her while I wasn't. I didn't care as I was getting off, and I felt an orgasm coming.

He fucked her hard as if he was getting out all the anger, spite, and fury he had at us. Sydney had lost her grip and had her head buried in the bed.

I was getting close to cumming, so I grabbed the nearest thing to me and came into it. I didn't realize that I came in Sydney's bra till I came down from the high of the orgasm.

They were still going hard, and I was surprised Matt hadn't cum yet.

At that moment, there was a knock on the door. I looked at them, but neither of them cared.

I wasn't sure what to do, but the knocking happened again.

This time, I opened the door, careful not to open it too much to reveal Matt and Sydney having sex.

It was Zoe who had come out of the shower.

She said, "The bathroom is all yours."

"Oh, thanks."

"Are you guys watching porn together?"

"No! I mean, I was trying to play music, but I had a porn video loaded up that played instead."

She rolled her eyes and went back to her room.

I closed the door, relieved we weren't caught.

When I looked at them, they had changed their position. She was now on top of him, riding him reverse cowgirl style.

Despite just having cum a few minutes ago, seeing her boobs bounce started the blood flow to my cock again.

I was lost in that sight till a loud clap sound broke my concentration.

"Fuck, yeah! Slap my ass!" Sydney said through gritted teeth.

Matt obeyed and followed through with a few more thunderous smacks on her ass. He then grabbed her hair and yanked her head back.

He was thrusting into her just as she was bouncing on his cock. They both stopped and let out loud moans.

They stayed in the position they were in for a while until Sydney got off his cock and lay next to him, both of them breathing hard.

After getting her breath, Sydney asked, "Will you be an ass?"

Matt shook his head.

"Is everything fine between the three of us now?"

He nodded.

"My work here is done."

She got out of bed and started to get dressed.

She put on her panties, but when she put on her bra, she paused and asked, "Why is my bra sticky?"

That's when I remembered I came in her bra.

She looked at me without taking off her bra and said, "You came in my bra, didn't you?"

"I grabbed the closest thing to me. I didn't realize it was your bra until after I came. Sorry," I said sheepishly.

She sighed but still wore her bra and put on the rest of her clothes.

After she went back to her room, Matt said, "Dude, you came on her boobs."

"No, I didn't."

"Technically, you did. Your cum is on her tits. So, you came on her boobs." He went for a hi-5, which I declined.

"I wish you'd go back to not talking," I joked.

I gathered my clothes and shower supplies and headed to the bathroom. On the way, I ran into Zoe, who was going downstairs.

"Done with the porno?"

"Uh, yeah."

Zoe and whoever else had showered had used up all the hot water. That made me take one of the quickest showers of my life.

When I got to the room, I told Matt there was no hot water, and he opted to wait for it to fill up again.

We headed downstairs, where everyone except Sydney was sitting in front of the TV.

Ray was working on the fire, Zoe was finding something to watch on TV, and Tyler and Soniya cuddled together tightly under a blanket.

Tyler asked, "Zoe, how have you not found anything to watch? You've been looking forever."

"There's nothing good. And, if I don't find anything, we could watch the porn video Jake was watching."