Senior Year at Sommerville High Ch. 07

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.

Ms.Santiago - Latina Home Ec teacher. She looks innocent and is easy to get along with. She has a shapely figure, but her big, round ass is her best feature.

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.

Linda - An air hostess whom Jake and Dani meet through their friend Hannah.

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CHRISTMAS EVE

My mom woke me up in the morning by knocking on my door, saying, "Jake, your Dad and I are heading out for some last-minute Christmas shopping. Breakfast is on the table."

I mumbled and tried going back to sleep but couldn't. My morning wood was causing me discomfort, and I was about to take care of it. Then I remembered that I hadn't used my weekly 'Dani' card yet and my parents weren't home.

The whole deal was still new to me despite being a month old. Dani had to remind me the first two weeks while I couldn't bring myself to ask her last week.

With this being the first time I asked her, I had trouble calming my nerves. I walked over to her bedroom and knocked on her door.

"What?" she said from inside.

"It's me."

"Ok. What do you want?"

"Mom and Dad aren't home, so I wondered if you could get naked while I jerked off?"

"Come in."

I let myself in and saw she was tightly bundled under her sheets.

"I'm way too comfortable on the bed, so I'll get naked, but you'll have to do it standing up."

"Yeah, no problem." I let my morning wood out while she removed the sheets and got undressed.

She rested against the headboard and said, "Hurry up! It's cold. And I can see you didn't bring lube." She rummaged in her nightstand and tossed me a bottle of lube.

"Don't make a mess on my floor."

I carefully poured a dollop onto my hand and applied it to my penis. Once I was ready, I started to masturbate.

We had never talked the previous two times, but she started a conversation this time. "Do you only masturbate when I'm naked?"

"Yeah. Ms.Santiago and I have been having sex once or twice a week. That's enough sexual release, but I don't want to waste this."

"Then why didn't you ask me last week?"

"Honestly, I was scared to ask."

"Scared?"

"Yeah. I know you agreed to this deal, but I get nervous. Plus, with Mom and Dad home, it's not exactly safe. Mom knows we were lying, and you have no idea how close I've come to blurting it out."

"Don't you dare tell Mom. They'll kick us both out of the house."

"At least you'll have money to get a place. That reminds me, what is the update on you moving out?"

"I've decided on the building, and now I'm deciding between the units. One of my co-workers' lease ends in April. If she doesn't extend her lease, she'll move in with me, and we'll get a two-bedroom. If she extends her lease, I'll get a one-bedroom."

I somehow had forgotten I was masturbating till I started to shoot cum everywhere.

Dani shouted, "Don't let any fall on the carpet!" But the damage had already been done.

"Shit, I'm sorry. I'll grab some paper towels." I ran to the bathroom and grabbed wet tissue paper, and dabbed on the cum stains. Dani also helped, and I lost my concentration as I watched her boobs move as she rubbed the carpet.

"Stop staring at me and get your cum out of my carpet," Dani instructed me.

We scrubbed for several minutes, and the carpet was wet from our cleaning. There was no way to tell if we were successful until it dried.

Sitting on the floor, she looked at me and said, "Next time, we do it where there is no carpet or bring tissues."

"Yeah. Sorry again."

"Whatever. I'm going to the bathroom, don't disturb me."

We walked out of her room and went our ways.

As I waited for my turn in the bathroom, I checked my text messages. Sydney had texted in the group chat.

Sydney: Good morning, everybody :)

Sydney: I know everyone is busy with Christmas and their family, but can we meet up and talk sometime today?

Sydney: Even a FaceTime would do. It's about our trip.

With this being our last winter break together, we had planned a trip. Sydney took charge and convinced her dad to pay for the whole thing. We decided to go to a small ski town for New Year's weekend. The most important things, like the cabin, transportation, and food, had been sorted out. But Sydney liked being extra meticulous with her plans.

Jake: I don't think I'll be able to get out of the house today. FaceTime works best.

Everyone else said the same thing, and we agreed to FaceTime at night.

Dani knocked on my door to let me know she was done with the bathroom. I brushed my teeth and got ready for the day.

Dani and I were eating breakfast when our parents returned from shopping. They had their hands full of grocery bags and gift bags.

We were hosting the family Christmas this year, and everyone had spent the past few days preparing. With it being Christmas Eve, everyone was on overdrive to make sure Christmas was perfect.

Mom started assigning everyone duties. Dad and I were in charge of getting the basement ready, Dani had to wrap gifts and prep food, and Mom was cleaning.

Dad and I went down to the basement and started tidying up. Since we rarely used the basement during winter, the cleanup was minimal. We spent most of the time bringing out extra tables and chairs and filling the bar.

We had been working in silence, and to break that, I said, "Thanks again for letting me go on that trip. I know it must've been hard to convince Mom."

"Not as much as you think. You taking her out every week made it easy. The hardest part was trying to make her understand why you're going to a ski resort when you've never skied."

"Sydney's dad is paying for it, and she wanted to go skiing. Matt is interested in snowboarding, and everyone wants to try it out."

"I hope you don't expect Sydney's Dad to pay for everything. I'll give you money for expenses at the resort."

"No, of course, we're going to split the extra expenses."

We were hanging up some lights when my dad realized the batteries were dead. He asked, "Can you run upstairs to my bedroom and get batteries? It should be in the nightstand drawer on my side of the bed."

"Got it."

I ran upstairs and walked past my mom, who had finished cleaning Dani's room.

"All done, Mom?"

"Yeah. Dani's room took me a while. There was a stain on the carpet that I couldn't make out what it was."

I immediately knew she was referring to the cum stain. To avoid questions from her, I ran to the master bedroom to get batteries.

After getting the batteries, I found Dani in the kitchen and said, "Mom, found the cum stain."

"What? How?"

"She was cleaning your room."

What did she say?"

"She doesn't know if it's cum. At least, I don't think she does. I ran before she could ask me anything."

"Nice going, you idiot. You made it look like there was something to hide."

"Where is she now? She wasn't upstairs when I came down."

"She's in the guest bedroom down the hall. We can convince her that the stain can be from anything. Just don't be a complete idiot and act sus."

I brought the batteries back to the basement, and Dad said, "Were they hard to find?"

"No, I stopped to talk to Dani."

"You guys have gotten closer recently. It's nice not seeing you guys go at each other's necks."

Fuck was he starting to suspect something also. There was no way, right? As Dani said, I tried not to act sus.

I replied, "We never really hated each other. It was just your usual sibling stuff. Guess we both outgrew the fighting."

"Whatever it was, I'm happy it's over."

The work in the basement finished within an hour, and to celebrate, my dad walked over to the bar.

He looked at me and said, "I know you've had your first drink already, but care to have your first drink with your old man?"

"Pour one up!"

As he poured me a drink, he warned me, "I know you teenagers prefer seltzers, beer, and gimmicky drinks, but this right here, this is a real man's drink."

I checked the bottle out. It was a Glenlivet 18-year Scotch Whiskey.

"I've never had whiskey before."

"Better prepare yourself. This is nothing like what you've had before."

I took a small sip, and it burned down to my stomach.

"Holy shit! How do you drink this?"

My dad laughed and said, "It's an acquired taste. Something you break out for special occasions." He casually sipped it like he was drinking water.

I went for another sip, but that was all I could do. I gave the rest to my dad and said, "I'll stick with the lighter stuff."

He downed both drinks and before heading upstairs, he said, "Do not tell your mother that I gave you a drink."

"I think Mom knows I've had alcohol before."

"She does, but there's only so much she can do with your friends. If I'm the one who gave you a drink, I'm in the doghouse for a long time."

"Don't worry, Dad. She won't know a thing."

Mom was preparing dinner, and Dad gave her company while I went upstairs to shower.

Dani was in the bathroom doing her skin routine. I asked, "Did Mom ask you about the stain?"

"Yeah, I told her it was coffee or something."

"White coffee?"

"The stain wasn't white. Anyway, she didn't ask me anything else. We're in the clear. But we have to be more careful."

"Yeah, I know."

I showered, and we had a family dinner. Mom asked, "I hope everyone has their clothes ready for midnight mass. The church will be packed, and if we don't get there early, we won't be able to sit together."

During dinner, I got a FaceTime call. It was the group calling about the trip. I excused myself from the table to pick up the call.

Instead of a discussion, Sydney just wanted to get our approval for her ideas. We had no problems because that meant less work for us. The only thing we had to worry about was getting ski gear.

We talked about random stuff for a while before ending the call. There were still a couple of hours before we had to go to church. Dad and Mom went to take a quick nap while Dani watched TV.

I decided to stay in my room and watch skiing tutorials on YouTube. As I watched the tutorials, I got a text from Courtney.

Courtney: Will I see you at Church tonight?

Jake: If you can spot me in the crowds. The church is going to be packed tonight.

Courtney: As it is every Christmas. What are your plans for tomorrow?

Jake: Family is coming over. What about you?

Courtney: Driving to my uncle's place right after mass.

Jake: That should be fun.

Courtney: Not really. I'm the only one my age there. Everyone is either way older or way younger.

Jake: Bummer.

Courtney: What were you doing?

Jake: Watching skiing tutorials.

Courtney: Oh, right. Soniya told me you guys were going to a ski resort.

Jake: Yup, we leave New Year's Eve morning.

Courtney: You'll miss out on the party. I was hoping you'd be my New Year's kiss.

I didn't know how to respond. This wasn't a friend asking to be their New Year's kiss. This was a girl almost certainly interested in you asking for a kiss.

While I was thinking of a reply, she deleted the message. I had my read receipts turned off, so she had no idea I had already seen it.

She sent another text.

Courtney: You'll miss out on the party.

I lied and texted back to make it seem like I didn't see the message.

Jake: I got caught up with something.

Jake: Yeah, it sucks missing out on a party in senior year.

Courtney: Couldn't you guys push the trip back one day?

Jake: Everything is already booked, and these were the only days that worked for everyone

Courtney: Oh.

Courtney: I have to pack for my uncle's house. See you at Church :)

Jake: I'll be on the lookout for you.

I sat back in my bed and thought about Courtney. I liked Courtney but didn't want to make a move due to Ms.Santiago. At that time, I wasn't having sex with her, but now sex had become a weekly thing.

Trying to make a decision had become even more difficult. My feelings for Courtney had slowly begun to grow. At the same time, my time with Ms.Santiago was getting equally better. I knew it would become tougher if I decided to put it off and make a decision later.

Not knowing what to do, I went to Dani's room to ask for advice.

I knocked on her door, and from the other side, she asked, "Are we leaving already? It's so early."

"No, we're not. I want to ask you something."

She opened the door and said, "What could you possibly want? You used your pass this morning."

"It's not that. I need advice."

She moved aside to let me in and closed the door behind her.

"Ok, little brother. How can I advise you?"

"You remember Courtney?"

"Busty blonde from church? The one that's into you, but you couldn't see it."

"Yeah. I don't know what to do about her."

"What about her?"

"I like her, and I like her more as time passes."

"Then it's simple. Ask her out."

"That's the thing, it's not that simple."

"Why?"

"Because of Ms.Santiago. I don't know if I like Courtney enough to stop having sex with Ms.Santiago."

Dani took some time before saying, "This is out there, but have you thought of telling Courtney about the sex? Maybe she's into an open relationship."

"No, that is out of the question. Ms.Santiago wants to keep the people who know to the minimum."

"Then I think you already have your answer. Till you like Courtney more than having sex with Ms.Santiago, you can't ask her out. Or if Ms.Santiago decides to end it with you."

I threw a pillow at her and said, "Don't jinx it!"

"That good, huh?"

"It's fantastic. The sex is great, and her being my teacher makes it 100 times better."

"You're making me regret not fucking a teacher when I was a student. There were some college professors I found hot."

Our mom started hollering that it was time to get ready. I went back to my room to change.

I was the first one downstairs, ready to go, followed by my dad, mom, and Dani.

Mom was pressuring Dad to go to the church as soon as possible. Even though we arrived half an hour before mass started, we couldn't find good seats.

Church was packed, but Mom found a spot on a bench big enough for three people. We tried our best to make it work, but it wasn't comfortable for anyone.

Before the mass started, I was on the lookout for Courtney. I saw her and her family walk in and told my mom, "Mom, this is too tight. I think I'm going to find somewhere else to sit."

"But we have to sit together for Christmas mass."

"It's a matter of one or two hours. It's fine, Mom."

"Oh, alright. Come back here if you can't find a seat."

"Will do."

I walked over to Courtney. She was still near the entrance, looking for seats.

"Hi, Jake!" Courtney said.

"Hey! If you're looking for seats, you're half an hour late."

"Yeah. My mom wanted to come early, but we got delayed packing. Oh, let me introduce you to my parents. This is Thomas and Marianne Reed. Mom, Dad, this is Jake. We go to school together."

Her mom asked, "Rosati? Are you Stella's son?"

"Yes, I am."

"I can see the resemblance. Is she here?"

"Yeah, they're sitting over there," pointing to their general direction.

"Tell your mom I said hi. I haven't spoken to her in ages. Oo, Honey, I see a couple of seats on the side. Let's go. Courtney, honey, we'll keep a seat for you, too."

Courtney's mom dragged her dad along, leaving Courtney and me alone.

"I take it you found a seat with your family."

"It's cramped. I was looking for somewhere else to sit."

"Mind if I sit with you?"

"Not at all."

The priest and the altar servers were about to make their entrance procession, so we decided to skip mass and go to the garden.

A few others had the same plan, but we were able to find a spot for ourselves.

The conversation was casual but lengthy. Even though we were outside, we could still hear the mass and kept track of time using that. When the recessional hymn played, I got up to leave. Courtney stopped me by saying she had something to say.

My heart beat faster, thinking she would ask me out or confess she liked me. I started to calm my nerves and think of lies to tell her.

"Jake, I don't want to make it any more difficult than it already is, so I'm just going to say it. I like you. I don't know if you like me, but I needed to let you know."

She looked at me with her eyes, waiting for a response. Everything that I had planned in my head vanished, and I was left speechless.

Courtney got up to leave, clearly sad that I didn't say anything. My body reacted without me telling it to. I grabbed a hold of her hand to stop her from leaving.

"I like you, but I don't think I'm ready for anything serious yet."

"Oh," she said dejectedly.

"We're in senior year, and I think it would be dumb to start a relationship now. We may go to different universities, and long-distance early in a relationship would be a death blow."

"I understand. Knowing that you like me makes me feel better."

People started leaving the church, so we went to the exit to make it look like we attended mass.

Once she spotted her family, she said bye, kissed me on my cheek, and left.

A huge weight had been lifted off my shoulder. I no longer had to worry about Courtney. And it felt like I left the door open for down the road.

My family walked towards me, and we got in the car.

After reaching home, we went straight to the Christmas tree. We had a tradition of opening presents right after midnight mass.

Mom opened her presents first. The first present was mine, and I gave her a bracelet with lockets. Each locket had a picture of one of us in it.

"Aww, Jake. This is so sweet. How did you make this?"

"The idea of a bracelet was mine. Zoe suggested the lockets and added the lockets and pictures."

"Tell her a thank you from me." She hugged me tightly until I asked her to let go.

I handed Dad his gift and asked him to open it.

He unwrapped it, and after examining it, he shouted, "NO WAY! How did you get this?"

"Dani lent me some money..."

"Which you better pay back soon," she interrupted.

"Wait till I get a summer job. Anyway, I was on the auction sites for the past few months. His retirement did not help, but I got one."

My mom cluelessly asked, "What are you talking about? It's just a football."

"No, hon. This isn't just a football. This is a football signed by TOM BRADY."

"Oh, that's great," she said, still not sure of the importance of it.

Dani then gave Dad an envelope, saying, "I know you don't like the Celtics as much as the Patriots, but I think you'll like this gift."

He opened the envelope and immediately exclaimed, "I have the best kids in the world."

Mom once again had no idea what was going on. She asked, "What's in the envelope?"

Dani replied, "I got Dad courtside tickets to a Celtics-Lakers game. I was thinking he could take Grandpa. And this is for you, Mom."

Mom unwrapped her gift to reveal a designer dress.

"Oh, Dani! You shouldn't have. This must've cost you a fortune."

"I bought it with the money I'm saving by living here."

They hugged, and it was Dani's turn to open gifts.

She got an outfit and a check for 250 dollars from Mom and Dad.