Senior Year at Sommerville High Ch. 06

"I thought it was a week from when we made the deal, so I have time till next Tuesday."

"No. Sunday to Saturday, any one time."

I didn't know when I would get back and if I did get back early, how much more tired I would be than I already was. So I asked, "Does now work?"

"It's up to you."

"Where's mom and dad?"

"Probably upstairs. Why?"

"Let's go to the basement."

She followed me down the steps and into the spare bedroom.

"You want to do it here?"

"They're all the way upstairs and we're all the way downstairs. Has to be the safest spot."

"What are you going to clean yourself with?"

I went to the basement pantry and found a packet of open napkins and returned to the room with them, saying, "Problem solved. Now strip for me."

"Ew, don't make it sound weirder than it already is."

"Yeah, I didn't think it sounded that weird in my head."

Dani took off her sweater and said, "It's way too cold down here."

I agreed with her. Being in the basement during winter was not pleasant but I said, "A deal is a deal."

The rest of her clothes came off and she stood before me nude. It was without a doubt cold in the basement, but if anyone had any doubt, one look at her nipples would've cleared them. They were perked up and looked like they could cut through anything.

She said, "Whip out your cock and hurry up. I'm freezing."

Not wanting to be cold myself, I slipped down my pants and boxers just enough to take out my penis. My body started rushing blood to my exposed member to keep it warm and at the sight of my naked sister.

"Hurry up!" Dani said.

"Hold on. I can't jerk off if I'm not hard. Let me get there," as I stroked myself till I got fully hard.

As I was about to start masturbating, Dani asked, "Aren't you going to use lube?"

"I don't have any on me, it's upstairs in my bedroom."

"Spit on it. You don't want to get a burn."

"Me spitting on it is weird."

"Let me guess, you want me to spit on it."

"I won't object."

She rolled her eyes and walked towards me. She bent down and let out a strand of spit fall onto my cock. After she did that a couple of times, I rubbed it thoroughly and started masturbating.

It was too cold and I was too focused on jerking off before Sydney and Zoe came that I didn't talk much. Due to the lack of time and the taboo situation, I was sure I would cum quick.

I felt the orgasm building up when I heard our mom calling for us from top of the stairs.

Dani replied, "Yeah, Mom. We're down here."

"What are you two doing in the basement?"

"I'm looking for something and Jake is helping me."

"Did you guys find it?"

"Nope, still looking." She looked me and gestured for me to hurry up.

"I'll come down to help you."

"NO! We got it. We'll be up in a minute."

I reached for the napkins and covered the head as I blasted cum into it. I needed a few more napkins to contain the mess. Once I had cleaned up, I tucked my penis away and looked at Dani.

She reached for her clothes on the ground and seeing her boobs hang made my cock twitch. She noticed the movement and looked up and said, "You only get one a week."

"I know."

After she put on all her clothes, we headed upstairs.

Mom asked, "Where's the thing you were looking for?"

"Oh, uhm, it wasn't what I had in mind."

"What were you looking for exactly?"

"Some Christmas decor to put in my room."

"Hmm," my mom said with a skeptical look on her face.

Not wanting to risk anything but staying longer than necessary, I said, "I got to get ready. Sydney and Zoe will be here in half an hour."

I rushed up the stairs and into my bathroom. I threw away the napkins and took a quick shower before going to my room to change into something casual.

I waited in my bedroom till I got a text from Sydney saying they were outside. I got up and walked downstairs. Dani was in the living room and when she saw me, she said, "Nice going, doofus."

"What?"

"Because you acted all nervous and ran upstairs, Mom thought something was going on."

"Oh, shit. What did she ask?"

"Luckily, a mom won't think that her daughter was posing naked for her son to masturbate. She asked me if we were smoking weed or doing drugs."

"That's a relief."

"Yeah, we got to be more careful next time and more relaxed. afterwards."

"Will do. I'm in a rush, see you later," as I ran out.

Zoe was in the driver's seat with Sydney in the passenger seat of her Benz. I sat in middle seat of the back row and asked Sydney, "Why aren't you driving your own car?"

"Because I don't want to look tired when I see Julian."

"Tired?"

Zoe interrupted, saying, "The girl said she'll get tired from driving. Now, don't take away this opportunity from me. This is miles better than my Corolla."

We set off on the long drive to the state university.

Not far into the journey, Sydney turned around to face me, and asked, "What do you think of Zoe and Mr.Grayson? Don't you think they'd make a cute couple?"

I looked at the rearview mirror and caught Zoe's expressionless eyes. Panicked, I said, "Nothing."

"Ahh, come on. They'd definitely make a cute couple. They're already banging buddies."

My eyes went wide and Sydney noticed it. "Oh, I get it now. You didn't know that I know Zoe and Grayson have been fucking."

Zoe started to laugh and said, "Thanks for acting like you didn't know, Jake. But I told her as you can probably tell."

"Phew, I had no clue what to say."

"Yeah, I think I may need to reconsider telling you secrets," Sydney said.

"Speaking of secrets," Zoe intervened, "Jake knows a couple of our secrets but he hasn't been telling us anything. Surely, you have to have some secrets, right Jake?"

I once again was stumbling for words. At the end, I managed to spit out, "No, not really. I don't really like secrets. Leads to unwanted drama and stress and all that. I mean, you see me trying to keep your secrets, imagine how much worse I would be trying to keep my own."

Telling Dani was not an issue for me. She didn't go to my school and she also would have been affected if word of me sleeping with my teacher got out. Even though, I trusted Zoe and Sydney, I didn't feel comfortable enough to tell them.

We pulled up to a red light, and Zoe turned around to look at me. Even after the light turned green, she kept staring, not moving the car despite the cars behind us honking.

I was about to break down and tell them but she swiveled her head around and started to drive. I took a deep breath to calm myself and reached for my phone to text Ms.Santiago.

Jake: Hey

Ms.Santiago: Hi :)

Ms.Santiago: Aching to meet up again? XD

Jake: Yes, but this is about something else

Ms.Santiago: Ok?

Jake: I told someone

Ms.Santiago: WHAT?!?!?

Jake: My sister, but she won't tell anyone. I promise

Ms.Santiago: Are you sure? Why would you do that?

Jake: I'm sure Nurse Mapleton knows and if you trust her to keep a secret, then you can trust my sister to keep a secret

Ms.Santiago: How do you know she knows?

Jake: She knew from the minute you took me to her office on the first day

Ms.Santiago: Ok, fine. She does know and I have been keeping her up to date. But we tell no one else

Jake: That's another thing I wanted to talk about

Ms.Santiago: NO. NO ONE ELSE

Jake: I know they won't tell anyone either

Ms.Santiago: They? How many people do you want to tell?

Jake: Two. I can assure you they won't tell anyone else. I've kept their big secrets and they would do the same for me

Ms.Santiago: That's not a guarantee, Jake

Jake: I know it's not like an actual guarantee but it is

Ms.Santiago: Why do you want to tell them so bad?

Jake: Because it's killing me inside. So much pressure trying to keep this a secret

Ms.Santiago: One. You can tell one person.

Jake: You sure?

Ms.Santiago: Yes but hurry before I change my mind

Jake: Thank you.

Ms.Santiago: Only thing I ask is that you fuck my brains out the next time we meet

Jake: That can be done

A huge weight had been lifted off my shoulder. I could only tell one person but I was certain I wanted that person to be Zoe. I had wanted to tell Sydney too but that was more because she happened to be in the car. Not being able to tell Tyler hurt but Zoe was the right choice.

I tuned back into the conversation in the car and Sydney was in the middle of talking about Julian.

"He's a converted vegan. He even made his parents and sister become vegans. He bikes or walks everywhere unless it's long distance. Then he does one of those things where you offset the emission by planting trees. He even made my dad return his BMW rental to get a Tesla."

Zoe said, "Uhm, Sydney, he kinda sounds...controlling. And no offense Sydney, but so are you. You think you guys can coexist?"

"We may both be a little controlling but we can make it work."

"If you say so."

When we were 10 minutes away, Sydney asked Zoe to pull over.

"I'll drive rest of the way and do you mind hopping in the back?"

Zoe joined me in the backseat and Sydney drove to outside an apartment. She texted Julian and a couple of minutes later, a guy with shaggy blonde hair walked up to the car.

Sydney rolled down the passenger window, asking, "Aren't you getting in?"

There was no response for him. She got out of the car and the two of them walked away from the car to talk. The conversation got animated fast and looked like they were arguing.

We didn't want to intervene knowing knowing anyone who would argue with Sydney would be just as unpleasant to deal with as an angry Sydney.

They were still going at 10 minutes later, so Zoe and I stepped out of the car to try remedy the situation but ended up getting sent back to the car like little kids.

Sydney then walked to the car and got in the driver's seat and slammed the gas pedal without warning. She drove like a madwoman till she pulled into a gas station. She then let out all her anger as she screamed.

Having no clue what to do, I turned towards Zoe who had already gotten out of the car to console Sydney. After Sydney had cooled down, Zoe asked, "What's wrong? What happened back there?"

"He's a big fucking jerk. You were right, Zoe. We can't coexist. Stupid idiot wants me to change my lifestyle and everything about me that makes me me."

"Better now than later, right?"

"Yeah. Ughh, get in there and let's go home."

"You want one of us to drive?"

"No, I got it. Don't have to worry about looking stressed anymore."

Zoe got back in the car so we could head back home.

Sydney went straight past the turn to my house and I said, "Uhm, you were supposed to take a right there."

"Oops, looks like we'll have to drop off Zoe first."

The tone in which she said that made me think she missed the turn on purpose.

We pulled in front of Zoe's house and Zoe asked, "You sure you don't want me to hang out a bit to make sure you're all good."

"Thanks for the offer, Zoe, but I just need some time on my own. Sorry for wasting your Saturday."

"None of that now. You know I'd do anything for you. Now give me a hug before I go."

Zoe walked into her home, and I took her place in the passenger seat. As I buckling my seatbelt, I asked Sydney, "Did you miss the turn on purpose?"

She looked at me with a smile, saying, "Smart boy. The only thing that can help me get over today is a good hard fuck and I know you're more than capable."

She shifted the car into drive and headed to her house.

We parked the car in the driveway and went inside. Mrs.Augustyne was in the living room when we came in.

Sydney said, "My rooms a mess right now, give me some time to clean it up. Ok?"

"Yeah, that sounds good."

I joined Mrs.Augustyne and the couch and she said, "I thought your hookups with my daughter were over?"

"Who said we're going to hookup?"

"No one has to."

Sydney called for me from top of the stairs and I said, "See you later."

"Ok, make sure you give my daughter a good time."

"Will do."

I went up to Sydney's room and she was already waiting for me naked.

Her bed looked like it had just been made and I asked, "Did you have to make up your bed if we're going to ruin it?"

"Yes, because having sex on a made up bed is better than a messy bed."

"Ok, but I have to tell you something."

She kissed me on the mouth and pulled me down onto the bed on top of her. She stopped kissing for a second to say, "Can the talking please wait? I really need a dick in me right now."

"But..."

Her tongue stopped me from continuing as we started making out. She pushed me down to her breasts and I realized I wouldn't be able say what I wanted to say, so I took her nipple into my mouth and started sucking on them.

Out of all the boobs I had seen, Sydney's were the best by a mile and I made sure I made the most of it. I didn't get enough of her tits as she made me go down on her.

Since Ms.Santiago and I stayed away from penetration till our last meetup, I had learned to become really skilled with my tongue.

I made sure to pull out all the tricks and Sydney sure did appreciate it. "Oh my God! You are fucking amazing at this."

Her legs started to curl and her back arched telling me that an orgasm was coming. She put a pillow over face to muffle her scream and her pussy started to leak from pleasure.

She removed the pillow from her face and looked at me to ask, "Why the fuck did you not eat me out last time? Matt was good but you're way better."

I thanked her for the compliment and got up and placed my dick at the entrance of her vagina.

She asked, "Don't you want a blowjob?"

"A blowjob would be nice, but right now I want to fuck you. You have condoms?"

"They're in the nightstand but I'm on the pill. Your choice."

"I think I'll pass on the condoms then," as I slid into her pussy. I solidified my base and started hammering away.

I was once again mesmerized by her tits moving each time I thrusted into her. My concentration was slipping and Sydney said, "Remember the priority is to fuck me, not stare at my tits."

"Roger that," as I picked up my pace.

I went hard for 5 minutes before I felt like I was about to cum. Knowing she needed a good fucking, I slowed down again and she asked what I was doing. I replied, "Do you want me to cum this quick? You need to be fucked good and I'm going to do that."

The pace had slowed down a lot to let me reset. Once I felt confident that I could last longer, I started fucking her hard again.

My penis started twitching in her letting both us know that I was about to cum. I didn't hold back as I ended with one final thrust as I shot my seed deep in her. She couldn't handle it all as semen started to ooze out of her vagina.

She used tissues to clean up the mess and asked, "Do you want that blowjob now?"

"Are you satisfied or do you want to go for round 2?"

"I'm satisfied enough to suck your dick." She crawled toward the end of the bed and took my dick in her mouth without using hands.

She sucked my dick good taking it deep and giving extra attention to the more sensitive zones. After 5 minutes of giving me head, she let my cock out of her mouth and said, "Face fuck me."

"What?"

"Grab me by the hair and fuck my face."

"If you say so."

She took my penis back in her mouth and I grabbed a handful of her hair and rammed her mouth. Her gagging was music to my ears but I was careful not to overdo it and give her time to catch her breath.

During one of her breathing breaks, she said, "Don't cum in my mouth. Save that for when you fuck me again."

I facefucked her one more time to the brink of an orgasm before stopping. She turned around so her ass was facing me. I was tempted to stick it in her ass and see what she would say, but today was a good day and I didn't want to ruin it.

My cock was already lubed up from her spit, and she was still plenty wet from the last fucking, so I slid in with no resistance.

I fucked her hard just like I did in missionary and my hand gravitated to her hair. I pulled her by the hair and it made the whole thing better. She was clearly enjoying it as she was moaning and screaming yes with each pump.

With a loud grunt, I let out my second load into her. We were both tired and laid in the bed for a while to catch our breath.

I remembered that I wanted to tell her something but she had already fallen asleep. Despite wanting to tell Zoe about Ms.Santiago, I thought that Sydney should know that I was sleeping with another person.

It wasn't worth waking her up to tell her, so I quietly got dressed and made my way downstairs. Mrs.Augustyne was still seated on the sofa, and upon seeing me, asked, "How did it go?"

"As good as it could have gone."

"I could tell by the sounds but I wanted to make sure."

"Were we that loud?"

"Not that loud, but I did stand outside the door for a bit."

"I don't know if that's weird or not?"

She smiled and asked, "Where's Sydney?"

"Asleep."

"Oh, so it must've been really good if you put her to sleep."

I shrugged my shoulders and said, "I'm not going to brag or anything but I yeah, I did fuck her really good."

"How are you going to go home then? Didn't you ride with her here?"

"Yeah, I did. I'll just get an Uber."

Mrs.Augustyne checked her phone and said, "I can drop you off. Mr.Augustyne won't be back for a while anyway and there's no need for you to waste money on an Uber."

"Thanks, but no thanks. I can get an Uber. Don't want to bother you."

"I offered you so you're not bothering me. Give me a second to get my keys."

After getting her keys, she put on a light jacket and we both got in the car. As she was backing out of the driveway, she asked me to tell her the directions.

We had just started driving when she said, "Oh shoot, I didn't even offer you water. You must thirsty after sex."

"No, I'm good. It's only 10, 15 minutes to my house anyway."

"Are you sure?"

"Positive. Uhm, since we're alone, do you think I could hear another one of your sex stories?"

She laughed and said, "Let's see. What do you want to hear?"

"Are you faithful to Mr.Augustyne?"

"Are you asking if I've cheated on him?"

"Maybe," I said not confident at all.

"Since we've been married, he has been the only I've slept with."

I clocked her answered and asked, "Does that mean you've cheated on him when you were dating?"

"Technically, it's not cheating when he knows about it and is fine with it."

"What? Why was he ok with it?"

"Because he was fucking someone else."

"You mean swinging?"

"If that's the term, yes, we were swinging."

"That's hot. How many times did you do that?"

"Not that many times. When he started the business, he needed some help launching it off the ground. It happened that the people who could help him were swingers. So, it was good deal for everyone involved. There was good sex and the business started to grow."

"How come you guys stopped?"

"He eventually reached a point where he didn't need help from anyone else. Once that ended, the swinging also ended. This happened the first 2 years we were dating."

"If you don't mind, how many guys did you sleep with during those 2 years?"

"I don't have an exact number but I will say that there are a lot of people involved in getting a business up and running."

The thought of her sleeping with lots of men made me horny. I subtly tried to adjust my boner but she noticed it and said, "Oh, I love how you young men recover so quickly."

"Perks of being young. I'm asking out of curiously, but what's the youngest you'll ever sleep with? Assuming your husband is fine and there's no other consequences."

She pulled over to the side of the road to look at me, and said, "Listen, Jake, I don't think we'll ever have sex. This is all fun for me without feeling guilty. Makes me feel like I'm doing something wrong without actually doing anything wrong."