Senior Year at Sommerville High Ch. 03

All characters are 18+

MAIN CAST

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

Tyler - Jake's best friend, pale and skinny with slightly chubby cheeks. He has bleached hair.

Soniya - Tyler's girlfriend, of South Indian descent and extremely pretty with long black hair and brown eyes. Average boobs and ass.

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.

Matt - is Irish with fiery red hair and is average in every way imaginable. Nothing stands out about him. He gets along with everyone.

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. 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.

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MONDAY

It was the Monday after Autumn Fair, and my heart and head were racing at a million miles per hour. I hadn't talked to either Sydney or Matt since what had happened on the Ferris Wheel on Saturday. I felt ok, but when Sydney was a no-show at church, I felt something was wrong.

I got ready and was heading downstairs when my phone notified me of a message. I looked at it, and it was from Sydney. She had created a group with Matt, her, and me.

Sydney: Morning, boys!!

Sydney: I think you know where this is headed

Matt: We have homework you wanted to remind us about. ¯_(ツ)_/¯

Sydney: The 3 of us don't even have a class together

Sydney: We have to talk about the Ferris Wheel

Matt: Do we have to?

Sydney: Yes

Sydney: How about an incentive for showing up?

Jake: What's the incentive?

Sydney: Why hello there Jake

Sydney: Decided to partake in the conversation now, huh? XD

Matt: Back to the incentive part

Sydney: *Picture of a pair of panties*

Jake: Are those yours?

Sydney: How did you forget so quickly?

Sydney: They're Amanda's, I'll let you boys have fun with it ;-)

Jake: Deal. Time and place?

Sydney: My place, after school

I walked downstairs, and my mom asked me, "You're later than usual. Overslept your alarm?"

"Not really. I just got hung up on something. What's for breakfast?"

"Banana Nut Waffles with turkey and pork sausages, veggie omelets, fresh fruit, orange juice, and I even went out and got Starbucks for you guys."

"Wow, Mom! You went all out today morning. Must've taken you forever to make all of this." It looked like the breakfast you get at a hotel.

"I couldn't sleep much last night, so I woke up early and made breakfast. It is the most important meal of the day after all."

My dad got up and said, "Yes, it is. And thank you, honey, for this delicious breakfast. I'm going to get a head start on my day." He kissed Mom and headed towards the door.

My mom said, "I'll walk you out, dear," and walked alongside him.

I was confused and looked toward my sister. I asked, "What was all that about? This is way more lovey-dovey than usual."

Dani asked, "Did you not see that glow on Mom's face?" I shook my head, she continued, "That's the glow you get when you have phenomenal sex." She emphasized each syllable in the word phenomenal as she said it. "Dad was going so hard, I heard the bed creaking from the hallway."

"Please, let me enjoy this breakfast." Dani was about to open her mouth again, but I was saved as Mom re-entered the kitchen and joined us at the table. Mom started talking about random things and didn't stop till I got up to go to school.

I arrived a few minutes before the bell. I rushed straight to homeroom not wanting to get a tardy.

In Chemistry class, I wanted to ask Madison what was going on between us, but she kept shutting down the topic. She finally gave in and said we would talk about it later. I didn't know if she was lying or being serious, but I didn't want to push it any further.

Next was Home Ec, and I was still waiting for Ms.Santiago to make the first move. I felt the awkwardness had faded, and she was comfortable with me again. During class and after, we talked with each other asking about our lives outside of school.

I told her I was off to lunch and walked out of her class to see Matt waiting for me.

"Hey Matt. What's up?"

"Yeah, yeah, I'm alright. You think Sydney is mad at us?"

"Why would she be mad at us?"

"Cause, you know? The Ferris Wheel."

"No, I don't think she's mad at us. She just wants to talk about it and make sure it's not awkward between all of us. It was only a game."

"Yeah, but still..."

"Matt, relax. She's not mad. She only wants to talk. Anyway, we'll find out after school."

I was sure Sydney wasn't mad, but seeing Matt being worried did make me think there was a possibility she was.

Matt and I headed to our lunch spot, and Sydney gave no hints. She behaved like she always did, and that made me feel better.

The rest of the school day went by in a blur, and I was in the parking lot ready to go to Sydney's. Tyler came to me and asked, "Yo! Want to help me pick out a suit?"

"A suit? Why do you need a suit? And don't you already have one?"

"Soniya's cousin's wedding is on Saturday. I don't know how to wear a traditional Indian dress so I'm wearing a suit. I want a new one to make a good impression."

Tyler did not care about clothes and often bought his clothes from GoodWill and Salvation Army, not because he couldn't afford other places, but because he didn't care. If it fits him, he would buy it and wear it till his parents told him it was too worn out. "Since when do you care about dressing nice and making a good impression," I said with a smile.

Tyler laughed sarcastically and flipped me off. He said, "Soniya's parents have always given me the cold shoulder whenever I've seen them. Can't do anything about that. Just want to control what I can."

"Damn, Tyler. You almost sound like an adult. What is up with you? Soniya must be doing something."

"Fuck off. You coming or not?"

"Sorry, man. Sydney asked Matt and me to come to her house."

"Is it about what happened at the fair?"

"Yup. Matt's freaking out, but I'm relatively calm. Anyway, you should ask Ray to come with you. If you want to impress Soniya's family, Ray can give you pointers and help you pick a badass suit. Everyone loves Ray."

"Yeah, you're right. I don't know why I asked you."

I gave him a backhanded slap. I walked to my car and waved goodbye. I started my car and was about to leave when I got a text message from Sydney in the group with Matt, her, and me.

Sydney: Got to make a quick stop. I'll be home in 10 min

Sydney: Come straight to the basement. I'll leave the front door unlocked

I left and headed to Sydney's house. I parked on the road, and Matt had already reached. He was waiting in his car, and I knocked on his window. He was still nervous, so I reassured him before we entered her house and went to the basement.

Sydney was relaxing on a recliner chair. She saw us, got up, and said, "Welcome, make yourselves at home. You know where the drinks and snacks are. Grab whatever you want and take a seat."

I grabbed a couple of water bottles and bags of chips and tossed one of each to Matt. He was sitting on one end of the sofa, and I sat next to him. Sydney, however, made me move so she could sit in the middle.

The first few minutes were us talking like usual. Matt's nerves got the better of him, and he blurted out, "Sydney, I am so sorry for what I said on the Ferris Wheel. I didn't mean any of it. I swear I was just playing the game. I have never thought of you sexually and will never think of you sexually. Please don't be mad at me." He said all of it in one breath that he spent the next few seconds catching his breath.

Sydney looked at him with a smile and said, "I'm not sure I got everything you said, but you got to relax, Matt. I'm not mad or anything. I had a feeling you were overthinking the whole situation. So, that's why I wanted to meet with you guys today. It is all good."

"Are you sure?" Matt asked.

"Yes, I am sure. I actually want to continue the game but with just the 3 of us. If that is ok with you guys."

I was caught off guard by what she said. I could tell Matt was too. He was staring at Sydney with his mouth slightly open.

I asked, "Are you serious? Or are you messing with us?"

"I'm serious. Playing truth or dare that day was one of the most exciting things I have ever done. I want to feel that excitement again. What do you guys say? We play and it stays between us," she raised her pinky finger in the air prompting us for a pinky promise.

Matt and I interlocked our pinkies with hers. She said, "Since this is my house, I'll go first. I already have a coin ready." She reached into her jeans and pulled out a coin. She tossed it and landed on tails. She said, "That means truth. Who's going to ask?"

I was going to ask, but Matt stopped me by saying, "No! Not you. You wasted your first question last time. Let me ask."

Sydney said, "Ok, then ask."

"What is the craziest sex thing you have ever done?"

I looked at him and said, "It's not that much better than 'Are you a virgin?'" I was salty I couldn't ask but didn't want to admit my question sucked.

She thought about it for a while before answering. "It comes down to two things. This past summer, I had sex on the beach. Maybe someone saw but I'm not sure. The other thing is, I've come to school with a butt plug before."

I asked, "Like, you mean a butt plug..."

"Yes, the butt plug was in my ass."

I could feel my cock starting to get hard. Luckily, I was wearing jeans, so, if I did get a boner, it wouldn't be that visible.

Sydney handed the coin to me and I flipped it. It landed on heads, meaning I had to do a dare. Sydney then suggested, "I think it'll be more fun if I ask you guys questions and you take turns asking me. Unless you want to ask each other." Matt and I agreed and Sydney thought up of a dare for me.

She then looked at me with a mischievous smile and said, "I dare you to show me your dick behind the bar counter." She got up and walked behind the bar. She used her finger to tell me to come to her. I got up and joined her behind the bar. She looked into my eyes and said, "Drop 'em and show me your cock." My hands went towards my belt and next thing I know, I'm standing in front of her in my boxers. My erection was straining against the fabric.

She noticed the erection and said, "Hmmm, you're hard. That makes it better. I hate to see a cock that isn't hard." There was a pause before she asked, "Do you want me to take it out?" and her hands moved towards my groin area. Her fingers clasped the waistband of my boxers and she slowly started to pull them down. Once, she got the boxers below my cock, it bounced and she dropped my boxers to the floor.

Her hand started to move toward my cock. I thought she was going to touch it and my penis flinched at the thought of it, but all she did was hold her hand for comparison. "Nice cock, Jake. Looks like it can fill a girl up and then some."

I was proud of my cock but in an attempt to be humble, said, "It's decent, but it's no 10-inch monster."

"Trust me, girls would prefer yours over a 10-inch monster. At least, I would."

"You're talking like you've had one that big before." She didn't say anything but she winked at me and went back to the sofa. I pulled up my boxers and jeans and joined them on the sofa.

Sydney asked, "Should I go again? Or should Matt go? We could do you guys ask me, then I ask one of you. Feels like it'll be more fun if I have more turns." We agreed and Sydney flipped and got truth again.

Since, Matt asked last time, it was my turn to ask. After some thinking, I asked, "Have you ever taken it up the ass?"

"You mean, have I done anal?" I nodded my head and she answered, "Nope, I haven't. I used the butt plug for fun. To see how it would feel."

Matt went next and got truth. Sydney wasted no time asking the question, "On the Ferris Wheel, you said what you would do to me in 15 minutes. But when you got here, you said you never thought of me sexually. My question is, have you ever jerked off to me?"

Matt hesitated to answer and Sydney said, "Remember, you cannot lie. Have you stroked that dick of yours while thinking of me?"

He looked at the floor as he answered, "I have."

Sydney smiled and asked a follow up question, "How many times?"

"You only get to ask one question."

"Answer this and I'll make it up to you."

"How?" Matt asked as his face lighted up.

"You'll see. Now, how many times have I made you cum?"

"I don't have an exact number, but I would say around 10."

Sydney was up again, and she got her first dare of the game. I could see in Matt's eyes that he knew what he wanted to say but wasn't sure about saying it. After a little encouragement from Sydney, he gave his dare. "I dare you to play rest of the game with your tits out."

I wanted to give Matt a hi-5 right then and there, but I played it cool, though I wasn't sure how well I did that.

Sydney looked at us, and stood up to face us both. She was wearing a light brown cardigan with a white tank top underneath. She unbuttoned the cardigan to reveal the tank top that was being stretched out by her boobs. She slipped off the tank top, and stood before us in a lime green bra. Her hands reached to the back clasp and asked, "Are you boys ready?" After we both nodded, she undid the clasp and let the bra drop.

They were marvelous. They were just as big as you would expect with perfectly sized nipples. They had a little sag to them because of how heavy they were, but that just made it better. She moved her hair so we had a clear view of her tits and she sat back down.

I tossed the coin and I got truth. Sydney turned towards me and her tits jiggled from the movement. "Out of Soniya, Zoe and me, who all would you fuck? Of course, there are no consequences."

I had never thought about having sex with any of them before, but after the question, I was finding it difficult to come up with reasons not to have sex with them. I moved my stare from her boobs to her eyes and said, "All of you." She had a suggestive smile and reached for the coin in my hand. As she did, her boobs touched my arm, which sent a jolt of electricity down my body.

She got dare and looked at me and said, "I am at your command."

Without thinking, I blurted out, "I want to have sex with you."

What I said was slowly starting to set in and I began to panic. I was going to apologize but she stopped me before I could. "Do you want to have sex with me or do you dare me to have sex with you?"

"I'm sorry. I just shouted that out. I..."

"I'm down. But I have one condition. Matt also gets a chance."

Matt asked, "You mean a 3some?"

She laughed and replied, "Maybe some time in the future. But, right now, Jake can go first and then you after. Now the question is, does Matt wanna watch? Because I want him too."

Matt shifted over to the recliner chair and Sydney and me stripped till we were naked. When I took my cock out, Sydney said, "I wanted to see your dick again, but I never thought it would happen so soon."

Sydney laid on the sofa inviting me to fuck her. Before I did, I asked, "Do you have condoms?"

"I do but I have a question for you. Do you trust your pull out game?"

As much as I would have loved to fuck her raw, I was not willing to take the risk. So I asked her for the condoms. She told me it was in her bag and I grabbed a handful and put them on the table. I put on a condom and got ready to fuck her.

I put one knee on the sofa and took her leg and placed it on the top of the sofa. I looked at her and asked, "Are you ready?"

"Give it to me." I grabbed my cock and guided it into her vagina. I started off slow and after a minute, she said, "You can surely go faster than that. Or I think I'm just gonna let Matt fuck me instead."

I readjusted myself and grabbed her hips to pull her closer to me. I said, "Matt will get his chance later. Now is about me showing you what I can do." I started drilling her hard and fast. The room was filled with the sounds of our bodies hitting each other and her short moans that coincided which each thrust.

Her boobs had a mind of their own as they were bouncing and moving all over her chest. Using my free hand, I grabbed one of her boobs and gave it a tight squeeze. Her hand went down to her vagina and she started to finger her clit as I fucked her.

We had been going for almost 10 minutes when I started to tire, so I leaned down so my body weight was on her and continued to fuck her. She brought her head up, and started to nibble on my ears, which gave me a second wind. It didn't even take 5 more minutes, till I came and she did shortly after. Her hand went to cover her mouth to mute her moan as much as possible.

I got off of her and sat at the end of the sofa. I looked at her to see what the aftermath was. Her vaginal area was a bright red and you could see my handprint on her boob. Her hair was a mess and sticking to her face as a thin layer of sweat had formed on her body.

Even though I had just came a few seconds before, my dick started to get hard again from the sight. I got off the sofa and pulled off the condom. I asked Sydney, "What should I do with the condom?"

She was still catching her breath and in between breaths, she said, "Just leave it on the table. I'll take care of it later."

Matt asked, "When do I get a turn?"

I had forgot about Matt, and when I saw him, he had his dick in his hand. I didn't know if when he took it out, but I suddenly felt shy and put my boxers back on.

Sydney sat up on the sofa, leaving a sweat mark on it, and said, "Give me a minute to catch my breath. Can I get on top? I think I made a mistake asking Jake to go harder."

Matt seemed to be happy with whatever as long as he got to fuck Sydney. He put on a condom and took a seat on the sofa waiting for Sydney to mount him.

Sydney went to the bar to get a drink of water. She then walked over to Matt, sat on his lap and held his cock so she could slide down on it. Once it was fully in, she went to work. And I meant, she WENT TO WORK.

She knew exactly what she was doing and rode Matt like a pornstar. She was grinding on him, and Matt was in heaven, trying his best not to cum quickly. About 5 minutes into fucking him, Sydney slowed down to almost a stop. I guess she could tell he was about to cum and decided to give him a chance to last longer. She smothered his face with her boobs before picking up the pace.

This time, she bounced on his cock and kept a quick pace till he came. Matt grunted as he let out his load and she kept going for a minute longer.

Still on his lap, and with his cock in her, she asked, "Are you happy? Is this what you imagined when you jerked off to me? Me riding you while my tits are in your face." All he did was nod with a stupid smile on his face.

She got off and sat next to him on the sofa. Now, not only was her vaginal area red, but it was wet and glistening from her pussy juice that leaked down her legs.

There was a few moments of silence that was broken up by Sydney. "I think the game is over, but you guys are more than welcome to stay."

"What do you want to do?" hoping she would see have sex again.