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.

Madison - The school's 'IT' girl. She looks like a model and does small modeling jobs. She has long brunette hair, perfectly tanned skin, and piercing grey eyes. She has above-average gravity-defying boobs with a cute butt.

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.

Felicity - A senior of 3 years to Jake. She is not shy about her sexuality and is well-known for her ass.

Mr.Grayson - The new teacher at the school. He is Jake's and Zoe's homeroom teacher. He looks to be in his late twenties.

Stella Rosati - Jake and Dani's mother.

Andrew Rosati - Jake and Dani's father.

Nurse Mapleton - The busty, redheaded school nurse who is close friends with Ms.Santiago.

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

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MONDAY

It was the first day back after Thanksgiving break, and the first two periods went by in a blur. I was in Chemistry class with Madison as Mr.Wojcik conducted a quick review class.

Discreetly, I asked Madison, "Did they choose your photos for the Thanksgiving promo?"

"No, they went with other models instead."

"Oh, I'm sorry. There'll be more opportunities down the road, right?"

"Of course, there will be. I'm still hot."

I chuckled, saying, "Yes, you are."

"And I'm glad I didn't have my photos selected."

"Why? Is this motivation for a model revenge tour?"

"You're so dorky. No, the photographer and campaign managers were pervs."

"What do you mean?"

"After my photo session, we looked over all the photos, and they raved about how good my photos were and how my photos were better than the other models."

"Ok, then why didn't they choose you?"

"That's the thing. After they said that, they asked me to sleep with them."

"What?" I shouted, enough to earn a scolding from Mr.Wojcik and have everyone in class look at us.

Madison waited till everyone went back to doing their own thing before continuing.

She hit me on the arm, saying, "Can you keep it down?"

"Sorry, I was surprised."

"Yeah, so was I when they asked me, but I didn't yell at the top of my lungs."

"My bad. What did you say to them?"

"What do you think? My photos aren't up anywhere, so I said no."

"Oh. So you're saying the models who got their photos selected slept with them?"

"Not sure. I didn't ask anyone else."

"Is this the first time this has happened to you?"

"I've heard of it before from other models, but yeah, first for me."

The bell rang a few minutes later, and after saying bye, I went to Ms.Santiago's class.

She knew everyone was still in the holiday spirit, so after taking class for the first half, she let us do whatever for the second half.

When the bell rang, I stopped at Ms.Santiago's desk to see when our next meetup would be.

"Is today the day we finally check out this new place of yours?"

"Yes, it is."

"Really?" I asked ecstatically. Since she had told me that we had to move from her house, I had been waiting.

"Yup. This is the best way to welcome you back after Thanksgiving. Do you have the address? I believe I texted it to you."

"Yeah, I have it saved. What time?"

"Does 7, 7:30 work?"

"Hell yeah. And if it doesn't, I'll make it work."

She smiled and said, "I'll see you then, Jake."

I left her classroom with the biggest smile ever on my face. I was so oblivious to my surroundings that I didn't notice Ray until he grabbed my shoulder.

I snapped back to reality and asked, "Hey, Ray. How's it going? How was Thanksgiving?"

"Thanksgiving was great. Both my parents were at home, and I saw Felicity yesterday."

"You did? Congrats, my man. What for? Or is this another one of those gentlemen can't tell moments?"

"Nothing like that. I got the courage to text her, and we met before she left."

"That's cool. Are you guys dating?"

"No, no, nothing like that. We're still relative strangers, and I don't think I'm ready to ask her out yet."

"Yeah, I understand, but still, small steps in the right direction."

We gave each other a fist bump and joined the others for lunch.

Sydney was the only one not there as she had just arrived from her vacation.

We spent the entire break catching each other up on how our Thanksgiving went, with me leaving out the orgy part.

Due to my anticipation of meeting Ms.Santiago after school, the rest of the day went by fast. I still had a few hours to burn, so I asked anyone if they wanted to hang out. In the end, only Zoe took up my offer.

We went to Stella's and ordered some fries and shakes.

Right after we placed the order, Zoe said, "I did it again."

"Did what again?" I asked, having no clue what she was talking about.

"Slept with Grayson."

"Alright, I can't say I'm surprised by that. I am surprised that you told me. You haven't been able to look me in the face since Halloween."

"I know, but I told you, and you're one of my best friends, meaning I can't avoid you. Now, don't expect me to give you a play-by-play anymore."

"Hey, the first and only time more than made up for it."

"You think about it often?"

"Would it affect our friendship if I say 'yes'?"

She smiled while saying, "No, it will not."

The waiter gave us our order, and we began to eat.

I asked her, "This is still purely for the sex, right?"

"It is. At least, for me, it is."

"Ooo, shouldn't you be sure you're both on the same wavelength? We have no clue how this dude is. If things go bad between you two, your grades are in his hands, literally."

Zoe let out a deep sigh before saying, "I know. But I'll deal with it when it happens. I want to enjoy some good sex while I can."

"I see you adopted my strategy."

"What strategy?"

"Dealing with stuff when it happens."

"Ah, it is a good strategy."

I was slurping up the last drops of my shake when I got a text. I quickly checked to see if it was Ms.Santiago, but it was Sydney in the group chat.

Sydney: Brought back souvenirs for everyone. Come to my house when you're free.

I looked at Zoe and asked, "Should we head to Sydney's?"

"Why not? Let me finish my shake."

We paid and got in our cars to head to Sydney's house. When I got in my car, I texted Ms.Santiago to make sure we were still on for 7:30. Unfortunately, she replied that something came up last minute, and we had to postpone for tomorrow.

No one else's cars were in the driveway when we got there.

Zoe rang the doorbell, and Mrs.Augustyne opened the door to let us in. She was wearing a long-sleeved, striped shirt with track pants. Her clothes hugged her figure, showing off her large breasts and toned ass.

"Hi, Zoe. Hi, Jake. Sydney's in the shower. Mind joining me for a coffee while you wait?"

"We just came from Stella's, but we'll give you company," Zoe replied.

"Perfect."

Mrs.Augustyne led us to the kitchen, where she had a cup of coffee waiting for her.

"How was your Thanksgiving?"

Zoe answered first, saying, "It was okay. The family came over, had Thanksgiving lunch, and watched football."

"I went to Boston to visit my grandparents. My cousins came from Florida, and I hadn't seen them in a year. So, it was nice seeing everyone and spending time with them. How about the Augustyne Thanksgiving?"

"We went to Cancun. I assume Sydney has already told you. It was nice getting a break from the cold."

"Not a big fan of the cold?" I asked.

"Nope, and neither is Mr.Augustyne. We're just here because Sydney refuses to leave Sommerville and you guys. We've been looking at houses in Florida, California, and Texas. Once Sydney moves out, we'll be able to move without objection."

"What about the family business?"

"Chance is waiting to take over, and Sydney is keen on proving she can run it too. Honestly, I don't stay updated on the business. The furthest my involvement goes is planning charity fundraisers and galas."

"You do a great job of that. My mom still talks about the gala you threw during our sophomore year," Zoe said.

Mrs.Augustyne blushed at Zoe's comment. "Oh, stop it. It was nothing."

At that moment, Sydney entered the kitchen in a sweatsuit and wet hair.

"Hey, guys," giving us both hugs.

"Zoe, want to come up to my room? I bought you the cutest dress. You have to try it on. I even bought some accessories that I think will match it."

Zoe stood up and said, "It was nice talking to you, Mrs.Augustyne."

"It was nice talking to you too. Aren't you taking Jake with you?"

Sydney replied, "Not yet. We don't want him to see us change." They went upstairs, leaving me with Mrs.Augustyne.

"I take it that Zoe doesn't know you and Sydney have had sex."

"Yeah, we haven't told anyone yet."

"Have you guys discussed telling the rest of your friends?"

"Can't say we've done that either. If we keep our mouths shut, it won't be that big of a problem, right?"

"Honey, you know your friends better than I do."

"Do you mind if I ask what happened between you and your friends?"

She smiled and said, "Do you want to know about the drama that happened or about the sex that led to the drama?"

I blushed knowing that she realized my intentions. I replied, "We're close enough where we can talk about our sex lives, right?"

"Are we now? I feel like I can count the number of actual conversations we've had on my hands," she said in a serious but also playful manner.

"That's all it takes to be good friends."

She giggled and said, "Someone is persistent. Hmm, I'll tell you on one condition."

"Name it."

"You have to tell me one of your sex escapades."

It was a fair deal but I the question was if I had something that I could tell her. The only time I had sex with my ex was when I lost my virginity and isn't something I wanted to share. Anything with Ms.Santiago was off the table, the Truth or Dare game on the Ferris Wheel doesn't count as a sexual escapade. The Thanksgiving orgy was also not an option. That left me with the blowjob Madison gave me in the girl's locker or the time Matt and I had sex with Sydney, and only one of those was actual sex.

I said, "The only thing I can think of is the time I had sex with Sydney."

"Is that the only time you've had sex?"

"No, but it's the only one I can tell you about."

Following some thinking, she said, "I guess that will have to do."

Aware that Sydney and Zoe could come down at any minute, I told her the story quickly, yet thoroughly. I started from the Ferris Wheel and the Truth or Dare game that took a sexual turn. That led to us playing a quicker Truth or Dare game which resulted in us having sex.

At the end of my story, she asked, "How was Sydney? Do you think she was good in bed?"

"First of all, we did it on the sofa, not the bed."

"Don't get smart with me. Remember, I still haven't told you anything yet." She had said that with a cheerful expression, so I knew she was just joking.

"Sydney was great. I will admit I don't have an abundance of experience, but she was great. Definitely will fuck again," I said with a grin.

Mrs.Augustyne slapped my hand, "Careful now, you're talking about my daughter."

"Sorry, have sex with again. Better?"

This time, she smirked before asking, "How much experience do you have? What is your body count as you kids say nowadays?"

I chuckled and replied, "Four. That's the number of people I have gone the distance with. There's a couple of ladies who I have done sexual things but not sex."

"Four at 18 years old isn't bad."

"What was your body count when you were my age?"

"More than four," she said with a smirk. "Shall we get back on track?"

"Of course. Whenever you're ready."

"Back when I was in high school, I used to be part of a group like you were. Except, my group only had five of us in it. Me, my best friend at the time Rachel, her cousin Alfie, Tony, and Steven. Rachel and I were co-captains of the cheerleaders, Tony was the star quarterback, Steven was the guy every girl wanted, and Alfie was the guy who could charm any girl into his bed."

"Why does this sound like you stole it from a high school movie?"

"Oh, shush. Believe me if you want."

"I'm just joking. What happens to you and your group of popular kids?"

"You can imagine that a group with so many 'popular' kids have their fair share of drama, and we were no exception. Rachel and Alfie are both only children, so even though they were cousins, they were more like brother and sister. Steven was her guy best friend and she had a crush on Tony. During a party in senior year, I ended up having sex with them."

"By them you mean all three of the guys?"

"Yup."

"One after the other?"

"Uhm, more like at the same time."

"WHAT!" I asked bewildered. Was she joking to mess with me? Was she teasing me? I had no clue if she was being serious or not. So I had to ask, "You were gangbanged?"

She tried to hold in laughter but she failed to do so. Once she had stopped, she answered, "No, I was not gangbanged. But I did have sex with all of them on the same night. I wanted to see your reaction and it was worth it."

I clearly didn't share the same amusement she did. "Not funny. Not funny at all."

"It was fun for me. Getting back to the story, Rachel found out, and things got ugly. She stopped talking to us, even Alfie. Tom, Steve, Alfie and I decided it would be best for us to distance ourselves till things cooled down."

"How long did that take?"

"20 years. We had our 20 year high school reunion and that was the first time Rachel and I had talked since she found out. Our group got back together and we still keep in contact."

"Was the sex worth it?"

"Yes and no. We thought Rachel would never find out and when she didn't know, it was worth it. But once she found out, not even sex with George Clooney or Pierce Brosnan would have been worth it."

"Were the two guys you weren't having sex with in the room watching?"

She exhaled sharply, then replied, "You're missing the point. I didn't tell you this to fantasize or give you an erection, I told you this as a warning. But yes, they were watching."

"I get what you're saying. Sydney said she's not sure if or when we'll have sex again. It could have been a one time thing."

"Really? She slept like a rock that night and when she woke up the next morning, she was the most cheerful I had ever seen her. Those are signs of great sex."

"It's not because the sex was bad, it's because the scenario has to be right. She said she wanted to have sex because it felt taboo. If she feels that way again, it could happen."

We heard Sydney and Zoe coming down the stairs causing a premature ending to our conversation. Sydney raided the snack pantry while Zoe modeled her dress for us.

"You look beautiful, Zoe. Ohhh, and these earrings compliment the whole look," said Mrs.Augustyne.

They began discussing about dresses and other stuff out of my realm of knowledge. Instead of standing there awkwardly, I went to the snack pantry to help out Sydney.

"Got any Hershey bars?" I asked from the entrance of the pantry.

She turned around with a her arms forming a basket full of snacks and drinks. "No, but we do have Ghirardelli."

"Too expensive for my taste. I thought you were dieting for an audition next month."

"I am, this is for you guys," as she dumped the snacks into my arms.

Sydney pulled Zoe away from talking to her mom and led us both upstairs to her room. She closed the door behind her and said, "I'm glad that only you two came."

Zoe and I looked at each other, before asking her why.

"I met a guy in Cancun."

"Again? How do you always find someone when you go on vacation?" Zoe asked.

I asked Zoe, "You know about the Greece guy?"

"You mean the guy who works for her dad? Of course, I do."

"I thought I was the only one that knew," I said looking at Sydney for clarification.

"You were, till I told Zoe. Did you think I wouldn't tell her? Zoe and you are my bestest friends. We've been together since kindergarten."

"Ok, forget about that. Who did you meet in Cancun and does he know you're the boss's daughter?" Zoe asked.

"Very funny," Sydney said with a straight face. "He's not an employee at the company. He's a junior at the state university."

"What are the odds?" I said.

"I know right! He's a few hours away and we don't have to worry about my dad firing him. He's tall, handsome, smart, a true gentleman, basically everything I want in a guy." Sydney went on to ramble about how perfect he was for a solid 10 minutes.

Zoe interrupted Sydney's rambling, "And so was the last guy. Mind telling me how this is different? You felt the same way about Greek guy too."

"Greek guy was for the sex. I wanted to have sex with him and then I found out he was a great guy. This is the opposite. We had 3 dates in 5 days, and none of them ended in sex."

"You do you, girl. We're here to support you."

"Great. I was planning on asking one of you to drive up with me to visit him but now I'm asking both of you."

Zoe and I knew we didn't have a choice so agreed to drive up with her.

I said, "My souvenir better be great if I'm gonna waste an entire day just so you can see a guy."

"I am the queen of gift giving," Sydney said as she dramatically flipped her hair over shoulder.

She had gotten me a few things. She got me homemade Mexican chocolate, a Nacho Libre mask and at the end, she lifted up a bottle filled with a clear liquid. She said, "This is for our next group hang out. This is local tequila, not the mass marketed stuff. My brother said it's 100 times better than the ones they sell in stores."

We spend rest of the evening hearing about Sydney's Cancun adventures and her boasting about the guy she met.

Mrs.Augustyne insisted that Zoe and I stay for dinner and we did. Mr.Augustyne was at the office meaning it would be us four. Dinner talk led to nothing interesting and Zoe and I left soon afterwards.

TUESDAY

As I was walking from the student parking lot into school, I spotted Ms.Santiago. I ran to her and asked, "What happened yesterday?"

I had startled her but she replied, "Good morning to you too, Jake."

"Good morning, Ms.Santiago. What happened yesterday? Why did you bail?"

"My nerves got the best of me but I promise you I will not bail tonight."

"We're on for tonight?"

"Yup. Same time, same place."

"And you for sure will be there. I won't get a last minute text saying you're going to chicken out."

"I promise you I'll be there. Now stop walking with me, I don't want people to start rumors."

Even though we had met up on several occasions, she was still paranoid about being caught. I couldn't fault her knowing that her career was on the line but I did think she took it overboard at times.

Due to my anticipation of meeting her in the evening, the school day went by in a blur. I didn't even get out of the school when I received a text from her.

Ms.Santiago: I'm heading there now. Don't take too long ;)

I rushed to my car and floored the gas pedal. I was lucky I didn't get pulled over or crash with how fast I was going.