Senior Year at Sommerville High

For those who were waiting for this chapter, I'm sorry. I went through a period of writer's block and then lost the motivation to write. I've been going through this chapter for a while now, confused about what direction to take. Feedback is welcome.

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All characters are 18+

CHARACTER GUIDE

Jake - The main character of the story. He has olive skin, messy brown hair, and an average body.

Tyler - Jake's best friend, a member of the group. He's tall and skinny.

Soniya - Tyler's Indian girlfriend, a member of the group. She has long black hair with a fair complexion. She has a curvy figure she keeps hidden under baggy clothes.

Sydney - Jake's friend, a member of the group. She's a busty blonde who is the self-appointed leader of the group.

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 himself whenever he can. He is a black teenager who looks like a pro athlete already.

Madison - The school's IT girl. She looks like a model with a shapely figure and piercing grey eyes.

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.

Ms.Santiago - Jake's teacher who is the crush of every student in school. Her ass is her best feature, but not lacking in the chest department.

Nurse Mapleton - The curvy red-headed nurse at the school.

Courtney - A busty blonde who has a crush on Jake.

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It was the first day of school after winter break. I had slept in and was late to school. Fortunately, since it was the first day back, Mr.Morrison would spend most of the homeroom period giving his welcome speech.

I walked downstairs, and my parents had left for work. Dani was downstairs getting herself a bowl of cereal. She looked at me and said, "You seem calm for someone late for school."

"Opening day, Morrison will talk everyone's ear off." I put a couple of slices of bread in the toaster and poured myself a glass of orange juice.

"Mom didn't make breakfast today?"

"Nope, she got called in for work early. Someone didn't do their job over the break, and now she and a few others are making up for it. That also means she didn't make lunch. She did leave you lunch money, though."

After searching the kitchen for the money, I asked, "Where is it? I can't find it."

Dani reached into her pockets and pulled out the money. She waved it before me as I tried to grab it from her but was unsuccessful.

"Give me it. I'm already late for school."

"One condition. We renegotiate the terms of our deal."

"What? Why? You're the one who came up with the idea in the first place."

"I know, and I feel it's time to change it a little."

When she had let her guard down, I managed to take the money from her. She tried to get it back from me, but I warded her off using my strength advantage. She made a swift move, and I reacted just as quickly. In the process, I accidentally touched her tits. This allowed her to get the money back from me. She didn't seem fazed by it.

"Sorry, I didn't mean to..." I began to apologize.

"What? Touch my tits? It's okay, Jake. You've already seen them. Touching them isn't a big deal."

Unknowing to me, my penis began to grow in my pants. She pointed it out to me by saying, "How much time do you have before you're late for school? Do you think we have time to take care of that?"

I checked the time on the oven clock and said, "If I don't leave now, I'll miss the start of the first period."

Slightly disappointed, she said, "Maybe after you come from school." She held out the money to me that I took from her. I hurried to school, hoping to make it before the morning assembly ended.

Luck was on my side as I didn't catch a red light on the way to school. I parked my car and snuck into the school without being seen by any faculty. I met the gang in the hallways as they left the auditorium.

"Where were you?" asked Tyler.

"Slept in. How did you guys wake up? I'm still sleep-deprived from the weekend."

Everyone's face shifted to an uncomfortable look. No one said anything for the longest time. The final bell for homeroom rang, and before we all left, Sydney asked, "We have to talk about it. My house after school?"

I was the first to respond and backed Sydney. "She's right. We have to talk about it if we're feeling uncomfortable. Meet at Sydney's after school?"

The hallways were now empty except for us. Mrs.Knox, the vice principal, was doing her rounds and asked us, "Shouldn't you be in class? Or are you debating whether to ditch class on the first day back?"

"We're on our way, Mrs.Knox," Sydney replied.

"Hurry up then. Wait any longer, and I'll have to write you guys up."

We split up and went to our respective homerooms. When Zoe walked in, I noticed relief across Mr.Grayson's face.

Zoe and I sat together, and I wanted to know how she felt about the ski trip.

"Mind if I ask you a question?" I asked.

"Let me guess. It's about the ski trip."

"Right on. How do you feel about it? Weird? Uneasy? Perfectly fine?"

"Not perfectly fine. Honestly, I'm ok with it. But I can tell some of the others aren't. I'm just playing along with the group."

"What does that mean?"

"It means I'm ready to go with the majority. I don't know what discussing this will lead to. Whatever it is, I'm ok with it. It felt weird at first, but it felt normal the longer it went on. That felt like a bonding moment as a group. Something to solidify our friendship when we all move on to college."

"That's one less person that needs convincing."

"Convincing? What are you trying to convince us about?"

I didn't say anything, but my expression told her what I thought. She asked, "You enjoyed it, didn't you?"

"Duh. Don't act like you didn't, too. You just told me you enjoyed it."

"I am not denying it. But you enjoyed it more than I did. I'm okay with it happening or not happening again. You want it to happen again?"

"Can you blame me? I saw four ladies nude at once."

She blushed a little at my comment. The bell rang for the first period, and we got up. As we walked out of class, Mr.Grayson called Zoe aside. Intrigued, I left the classroom but stayed around the corner where I could hear what they talked about.

He started the conversation by asking, "How was your vacation?"

"It was good. Quick, I have to get to my class."

After a sigh, he said, "I'm sorry, okay. I was stupid and horny. Can we go back to what we had? Forget about what I asked."

About what he asked? This was getting interesting, and I wondered what had happened between them.

"I'm still going to need time. We'll talk about this later," she replied.

That was my cue to leave. I quickly and quietly walked away from the spot and went toward my class. My mind was hung up on what could be up between Grayson and Zoe. Madison and third-period chemistry helped me take my mind off it.

"It's nice seeing you after a long time. How was Christmas?" I asked.

"Yeah, it was alright. Listen, I need your help."

"Thanks for asking how I am."

"Oh, shut up. Can you help me or not?"

"It depends. What do you need help with?"

"A photoshoot."

"A photoshoot? I have never held a camera other than the one on my phone before. I've actually been demoted from family photographer because my photos are so bad."

"When you're taking photos of me, the photos can't be bad."

"Ok, but why do you need me to take photos of you?"

"Remember how I told you I didn't get the Thanksgiving gig because I refused to sleep with the disgusting pig that was the campaign manager? I've lost a few other gigs to worse models. So, I've decided to level up and aim for the big jobs. I'm creating a portfolio to send to New York and LA."

"Portfolio? That sounds like you need someone who knows what they're doing."

"I don't trust anyone else to not perv on me while taking the pictures."

"Wait, what pictures are we taking exactly?"

"A little risque."

At that moment, the teacher called us out, "Madison, Jake, if you're not going to pay attention, at least don't disturb the class."

We apologized and kept quiet for the rest of the class. After class, while in the hallway, she said, "Meet up after school today?"

"I can't. I'm heading over to Sydney's house with the gang."

"Text me whenever works for you then."

"Will do."

I continued to walk toward Ms.Santiago's classroom. I hadn't seen or talked to her since school had closed for winter break. I was nervous seeing her again because it felt like we had to start all over.

As I entered her class, she smiled but didn't say anything. The class went by fast as I was ogling at her, as was every other guy. She gave us the last 10 minutes of class to relax since she knew we were still in the holiday mood.

She slipped me a note as she walked past me. I opened it and read, 'Meet me in Nurse Mapleton's office after class. We need to talk.'

I wondered what she meant by talk. Did she want to talk or recreate what we did on opening day? The bell couldn't ring soon enough.

After an eternity, it finally did, and I bolted to the nurse's office. I busted through the door and was surprised when Nurse Mapleton was there.

"Oh, uhm, sorry. I wasn't expecting you here."

"You weren't expecting the nurse in the nurse's office?"

"I mean..."

"Ms.Santiago sent you here, didn't she?"

"Uh, eh, uh..."

She smiled and said, "I already know. She asked me ahead of time. Don't worry. I'll get out of here and leave you two to it." She gathered her stuff and left me alone in the room as I waited for Ms.Santiago.

Ms.Santiago finally joined me in the nurse's office.

"Took you long enough. I thought I got stood up there for a second."

"You know I would never do that to you. How was your winter break? I didn't get a chance to talk to you. My family was over, and I got pretty occupied."

"No worries, I was busy too. Uhm, winter break was fun. I went on a skiing trip with the gang. Had a good Christmas with the family."

"That's nice."

Neither of us said anything for the longest time. I ended the silence by asking, "What did you want to discuss? Or did you have something else on your mind?" I didn't know why I said that, but I liked my chances. She was usually the one who always took charge.

"Oh, God. I rehearsed this many times in my head, but I'm nervous."

That made me a little unsettled. This was what my ex-girlfriend told me word for word before she broke up with me. Was Ms.Santiago ending things? There was no chance she was. Was she? A million other thoughts flooded my head, and none were good.

"Ok, well, as you know, I'm getting up there in age. My friends and cousins are married and have kids. And my family is very traditional. At my age, every single woman in my family had at least two kids."

Stupidly, I asked, "Are you asking me to marry you?"

"What! No! Not at all! I want to settle down. And my parents want me to settle down as well."

The second those words came out of her mouth, my heart dropped. This was even more painful when I got broken up with. I couldn't remember the last time I cried, but now I was holding back tears.

She waved her hand in my face, asking, "Jake? You here?"

I snapped back and replied, "Yeah, yeah. You were saying you want to settle down?"

"Yeah. My parents introduced me to their friend's son, and we hit it off. And as much as I love what we've been doing, I can't carry that on."

"So it's over. Just like that."

She looked at me with sympathy and said, "It's over, but not necessarily yet. I want us to end things on good terms. If you're up for it, that is."

I was still too distracted to respond and just mumbled.

"I'll give you some time to think about it." She caressed my face and said, "Whenever you decide, let me know. And sorry it had to end." She parted with a quick kiss on the cheeks, leaving me alone again.

After taking a few minutes to collect myself, I slowly walked to join the gang for lunch.

Zoe noticed my sullen expression and asked, "What's up with you? You look like you're down in the dumps."

"Still sleepy, and now I'm getting a headache," I lied.

She didn't buy it as she gave me a side-eye. I didn't contribute much to the conversation. Most of it was about meeting at Sydney's house after school. The rest of the day dragged by.

The final bell rang, and I was walking to the parking lot. Before I stepped outside, I heard my name being called. I turned around and saw that it was Nurse Mapleton.

She jogged to catch up to me, and I couldn't help but get distracted by her boobs. I wasn't discreet about it either, but she acted as if she didn't see anything.

"What's up?" I asked.

"Ms.Santiago told me what happened. I wanted to check on you."

"I'm doing fine."

"You don't look like you're doing fine."

"You can understand why I'm not."

"I can, but maybe this opens up new doors," she said suggestively.

I looked at her to see if her facial expression matched her tone. I couldn't tell for sure, but it did seem like she was flirting with me.

We stopped at the door, and to test her, I asked, "What kind of doors are you talking about?"

She shrugged and mischievously said, "That's for you to find out." She left as I stood at the door, mulling over her words.

My phone buzzed with a text from Zoe.

Zoe: Where are you? I'm waiting outside your car.

Jake: Omw.

I spotted her sitting on the hood of my car, and I asked, "What are you doing here?"

"Waiting to hitch a ride with you."

"Where's your car?"

"My mom dropped me off in the morning."

"Why didn't you hitch a ride with one of the others?"

"Didn't feel like it."

"Was waiting in the cold worth it?"

"Yup."

I unlocked my car, and we both got in the front seats. Immediately after we settled, she asked, "What's wrong with you?"

"Like I said before, just sleepy and have a headache."

"You're not fooling me with that excuse. Now tell me what's wrong before I annoy the hell out of you."

I was torn on whether to tell her what was wrong. Initially, I had planned to let her in about Ms.Santiago and me, but I opted to tell Dani instead. Ms.Santiago was strict about keeping the people who knew about it to the minimum. But with the things over between us, I felt like that was no longer the case.

After taking a deep breath, I looked at her and said, "Before I tell you anything, I need you to promise me that no one else will know about this."

"Geez. This sounds super serious. I swear on my life that I will not tell anyone."

I took a moment to confirm I wanted to go through with it before saying anything. "Do you know how you and Mr.Grayson had a little thing going on?'

Her face reacted immediately as she knew where I was going with this. Instead of interrupting, she waited for me to continue.

"Well, I had something similar going on...with Ms.Santiago."

"You sneaky little bastard! Ms.Santiago! How? She's so innocent. Do you realize how lucky you are? Every guy in school would kill to be in your spot."

"Yeah, well, there's nothing to kill for now. She ended it. She found somebody else and has no time for me anymore."

"Ah, that's why you're sad. I don't mean to pile on, but you can't blame her. How long did you expect her to fool around with you? You guys still had a teacher-student relationship that could have ended badly."

"That hasn't stopped you and Grayson," I snapped back.

Her face turned for a bit before she responded. "For your information, we ended it as well."

"What?" I asked in shock.

"We ended it. Trust me, I would've loved to keep it going, but it was the right thing to do."

"When?"

"During winter break."

Before we could discuss it any further, Tyler called. I picked up, and he asked, "Where are you? We're all waiting for you and Zoe."

"Sorry, I got tied up with something. We're on the way."

I hung up the call and started driving to Sydney's house. On the drive there, I wanted to ask her more about the Grayson situation, but she didn't seem open to conversation. Instead, we let the radio fill in the silence.

We pulled into Sydney's driveway and let ourselves in. I hoped to see Mrs.Augustyne, but she wasn't there. We took the stairs to the basement, where the rest of the gang was watching TV as they waited for us.

"About damn time!" Sydney said as she saw us. "We all agreed to meet at my house after school."

Not in a good mood, I replied, "You said after school, we're here. You didn't say a specific time."

Zoe punched me in the arm, knowing Sydney could blow up at me. Fortunately, Sydney let the comment slide and carried on. "Alright, we all know why we're here. So let's rip the bandaid off and get right to it."

Even though Sydney mentioned why we were here, she didn't address the issue. Tyler stepped up and said, "Alright, I'll start. We saw each other naked, watched each other orgasm, and watched Soniya blow me..."

Soniya's face turned bright red as Tyler said that.

"That probably doesn't happen in most friend groups, but it happened in ours. Now, this should only strengthen us instead of driving us apart. What do you guys think?"

Zoe responded, "Not relevant to the topic, but I'm impressed with you. I never knew you could be so smart and mature. Very well said, Tyler."

"Yeah, I can be when I want to be. I leave it to you guys, though. Someone has to be the funny one."

Sydney brought us back to the topic, saying, "Can we discuss what we're here to discuss?"

"I don't know what there's to say," Soniya said. "It was awkward while it was happening, but I'm feeling comfortable with what happened as the time passes."

"Comfortable?"

"Ok, comfortable may not be the right word, but it felt less awkward."

Matt made his first contribution as he asked, "Where is everyone now? Comfortable enough to the point it could happen again?"

That last question hung in the air as no one wanted to be the first to answer. I was on board, and I could tell Matt was, too. Based on our conversation in the morning, Zoe was also ok with the idea. I assumed Tyler and Sydney would also be ok with it. That just left Soniya and Ray.

With no one answering his question, Matt repeated it. This time, he got a response from Zoe. "I could see it happening again, but it has to happen naturally."

"Oh, come on," Sydney said. "If we wait for it to happen naturally, it'll never happen."

"What are you saying?" Matt asked eagerly.

"I'm saying that if we want it to happen again, we do it. Not wait for things to align."

"Do we want it to happen again?" Soniya asked.

"Yes!" both Sydney and Matt exclaimed.

Ray spoke for the first time, "Hold on. It's clear not everyone is 100% on board with this. Why don't we let it sit?"

The group decided that Ray was right, though some were more reluctant than others to agree. We hung out for a while longer before going back to our homes.

Upon reaching home, I went straight to my bed, where I caught up on some much-needed sleep. I woke up in the middle of the night and checked my phone to see the time. It was past 3 AM, and I had missed a text from Dani.

Dani: Text me when you wake up.

I figured she would be asleep and didn't bother texting her back. I spent some time awake before trying to go back to sleep. Despite my best efforts, I couldn't fall back asleep. Instead, I was thinking of the situation with Ms.Santiago.

I fell asleep eventually but ended up sleeping through my alarm. When I woke up, I had already missed the first period. With no need to hurry, I casually made my way to the bathroom.