Senior Year at Sommerville High Ch. 04

"Ok. Are you sure you can walk though?"

She pushed my hands away in an attempt to prove me wrong but stumbled her first few steps. I quickly put my arm around her hip and her hand around my shoulder. I said, "I'll take you there."

"I can walk but I'll let you be a good friend."

"Thanks, Z."

We found a place to sit and she rested her head on my shoulder. She mostly talked non-sense to which I gave generic responses every now and then to make it sound like I was listening. Instead, I was scrolling on my Insta feed.

My feed was full of Halloween posts. The school had posted a picture of the faculty Halloween party and I spent some time checking the photo out, mostly because Ms.Santiago was in it. She was wearing a cute cat costume that she made look sexy.

As I was looking at the photos, Zoe said, "I fucked him."

I was confused and assumed she was talking about some guy who had walked past us.

She added, "I told him to wear that. Looks good doesn't it."

"Z, I have no idea who you're talking about."

"Grayson."

I turned abruptly which caused her to tumble sideways. I then asked, "Grayson? Like Mr.Grayson? Our homeroom teacher?"

She sat back up straight with some effort and said, "Yeah. What other Grayson do we know?"

"Are you messing with me?"

"No, I had sex with Mr.Grayson. Why are you so surprised? You're the one who's been pestering me to admit I had a crush on him."

"A crush. Not that you wanted to have sex."

"Well, don't most people want to have sex with their crushes."

"Fair point. Are you messing with me?"

"Nope. I've been wanting to tell someone for the longest time but I didn't have the courage. Now that I got a few drinks in me, I felt free enough to say it."

"When exactly did this happen?"

"First time happened end of last month, second time was last week and third time was this past Sunday."

"Three times!"

"Yup, he's good. He's made me cum more than Travis has ever had. I guess it comes with the age."

"Z, you know you guys are playing a dangerous game. He could get in a whole lot of trouble. So could you."

I knew it was hypocritical coming out of my mouth but she didn't know I was fooling around with Ms.Santiago. Plus, we've only gone as far as oral, not full blown sex.

"Wait, are you doing this because you miss Travis?" I asked.

"I don't know. All I know is that when Travis and I broke up, a big gaping hole appeared that I needed to fill. Mr.Grayson happened to be the one to help me fill it."

"Is this romantic? Like you're dating?"

"We haven't been on a date. I don't know if feelings are involved. It's just been good companionship mixed with meaningless sex. Both of us are happy."

"I hope you know what you're doing." Zoe's a smart person and always made the right decision. I hope this was also one of those decisions.

Months of me clawing at her to get some information and she told me everything I wanted to know and then some. I sat there overwhelmed with what she had told me.

She interrupted my thinking by saying, "Listen, Jake. I haven't told anyone else and I don't think I will. Like I said, I needed to get it off my chest and you happened to be the one to hear it. Please, please keep this to yourself."

"Yeah, of course. This is purely curiosity but how did it go down?"

"You want to know what we did?"

I sheepishly nodded.

"Why? So you can go home and jerk off thinking about it."

"No. Never. Not at all. I would never do that."

"Really? Good because I would totally be disgusted with you if you did that," she said with the most sarcastic tone I had ever heard.

She continued, "Hmm, I guess I'll tell you what happened on Sunday. I think that's the best."

"Ok."

"Like you said, it's risky, so we found this motel a couple of towns over which is notorious for being a hook up place. We get to our room and since this is our third time, there's no awkwardness, we get straight into it."

I repositioned myself so I was facing her.

She then continued, "We're kissing while we walk towards the bed and I lay on it with him on top of me, without taking our tongues out of each other's mouths. My hands move to his jeans where I unbutton and unzip it and he helps me pull them down. I slide my hands into his briefs to play with his cock. He takes off my jeans and panties so he can slide a finger into me and then another one before he starts fingering me. He fingers me till I'm wet and leaking out of my vagina. I'm ready to get fucked and he know it. So, he pulls his cock out, and teases me by tracing my vagina with it before he slides in and starts fucking me."

My cock was aching so bad and got into an uncomfortable position in my boxers. I didn't care that I was in public, I had to readjust it and I did just that. I tried to do it over my pants but that wasn't working, so I quickly snuck my hand into my pants to get more comfy.

Zoe saw this and just smiled as she watched me. After I pulled my hand out, she asked, "Feel better? Can I continue?"

I nodded eagerly.

"Hmmm, so where was I."

"He just started fucking you."

"Ahh, that's right. So he's doing it real slow. Pulling all the way out and pushing all the way in. It's painfully teasing but I love it. He does it for I don't know how long before I decide I can't take it anymore and I want to get on top, take control. Quick maneuvering and I'm on top of him. I put my hands on his chest and break out every trick in the book when riding a guy. Grinding, bouncing, gyrating, whatever you can think of, I did it. I then leaned back and rested my hands on his thighs and started bouncing on his cock. I kept on going till I felt him cum in me. I felt each and every one of his spurts shooting deep inside me. But I didn't stop. I kept on going because I wanted to cum too. I was almost there when he grabbed me by the hips and flipped us so that he was on top. He grabbed my face and drilled me hard. Fucked me with no restraints, pounding into me. I then felt an orgasm starting to build in me. My toes started to curl, my legs hugged him, my body started to twitch, my nails dug into his back, my head shot back and I was on the brink of an orgasm. I took one last gasp as he thrusted into me one more time and I came so...fucking...hard. My eyes rolled back into my head and body twitched as my climax took over."

I stared at her, mouth hanging open, going crazy imaging what she said.

She smirked and said, "But we weren't done. He pulled out of me and then led me to kneel on the floor with my head resting against the bed. I knew what was going to happen and so do you. I opened my mouth, but he started drawing circles on face with his cock covered in both of our cum till the circle kept getting smaller and smaller before it ended up in my mouth. He fucked my mouth just like he fucked my pussy. I felt him in my throat and could tell he was about to cum. I opened up to my max to swallow as much as I could. It didn't matter that he came in me a few minutes ago, there was still so much cum that it oozed out of the sides of my mouth. He took out his cock and rubbed it and beat it on my face. I got up, we made out and that's what happened on Sunday."

I swallowed my spit and asked "Did that actually happen? Or were you just playing it up?"

"All of that happened, I just added my creative touch to make it even sexier."

I was still in awe of what I heard when Sydney found us and said, "Guys, party is dying out. How about we head home?"

"Sounds good," Zoe said.

Zoe and I got up and followed Sydney to where the rest of our friends were. Matt had sobered up while Tyler and Soniya looked pretty decent despite downing their fair share of drinks. Ray was in the worst condition.

I didn't know if it was because this was his first time or he had way too many drinks, but he was gone. Tyler and Matt were supporting him from both sides while Soniya was making him drink water.

My brain was still overloaded from what Zoe said that I zoned out from the conversation and didn't hear anything till Tyler flicked me in the arm, saying, "Let's go? What world are you in?"

We eventually got to the car though Ray did not make it easy. It wasn't as much as Ray doing anything to make it difficult but more like him doing nothing at all. We basically had to drag him to the car and make a couple of stops to catch our breath.

Along the way, Sydney said, "Note to self, never trust Tyler with drinks."

"Hey!" he responded. "At least, now we know what his limit is and what he likes."

I texted my sister Ray's address and told her I was leaving before I set off to drop everyone.

Zoe's house was first and Soniya had to help her to the doorstep. We called Zoe's little sister from her phone so she could help Zoe up to her room. Once we got the 'all ok' text from Zoe, I drove to the next house.

We didn't have to worry about anyone else except for Ray but I told the group that I would manage on my own.

Sydney was the last one I had to drop off. She got out of the car and said goodbye to Ray which she got no response from. She walked over to my window and asked, "Are you sure you can handle him by yourself?"

"Yup, or I'll find a way somehow. Good night, Sydney."

"Good night, Jake." She leaned in through the window and kissed me on the lips. She smiled and walked into her house.

I pulled into Ray's driveway and saw that my sister had already reached. I ran up to her window and told her, "Give me 5 minutes to get him inside."

I went back to the minivan and was thinking of the best way to get Ray inside. It wasn't easy getting him out of the car but I managed. It was even more difficult to walk him to the door.

I only made it halfway when I heard my sister say, "Gosh, as funny as it is watching you struggle, I don't have the patience for it." She got Ray's other side and it made it a whole lot easier.

I opened the front door with his keys and we only took a few steps when we heard Ray's grandma. "Ray, is that you? Why were you out so late?"

We froze as his grandma entered the room to the sight of a drunk grandson being helped by 2 people.

We thought we were busted. Ray was too drunk and I thought my sister and I would get an earful from his grandma for getting him drunk. To my surprise, that wasn't what happened.

She said, "Oh, boy. You have no idea how long I've waited to see this."

My sister and I looked at each other wondering if we heard right.

Ray's grandma continued, "I wished he wasn't this drunk but not everything is perfect."

She saw the confused looks on our faces and said, "You must think I'm some crazy ol' lady. You're the boy who went with him to the track meet, right?" as she pointed at me. I nodded and she then asked, "Who is this pretty lady then?"

"I'm his sister."

"Ah, ok. I thought my Ray went and got himself a girl. Anyway, you know how tight and wound up my baby is. Can't blame him, my daughter and her husband got him living a life more strict than they do in the military. I've been asking him to let loose a little and boy did he."

I replied, "Uh, yeah. He may have gone a little overboard. But it's a learning lesson, right?"

"Yes, it is. Thank you for making sure he got home safe. His room is down the hall, last door on the left. I'll get him some water and Advil for that morning hangover."

After Ray's grandma left, the three of us lumbered our way to Ray's bedroom.

We got inside and I heard Ray mumble, "Hmmm, feels nice. They're bigger than the other ones. I like it."

I assumed he was talking to himself but then my sister said, "Thank you, Ray but I'm going to move your hand now."

I looked over and saw Ray had a handful of my sister's tit. He wasn't just grabbing it either, he was squeezing and playing with it too. She took his hand off her tit and we laid Ray down on his bed.

His grandma came in with a bottle of water and Advil and put it on the nightstand. "Oh, would you guys also take him out of his uniform? He'll be uncomfortable all night."

"Uhm, sure."

His grandma thanked us and left the room.

We had a hard time getting the jersey off. Ray went full out and put on his pads like he would before a game.

My sister asked, "How do you take this off?

"I don't know. I've never put on pads before."

It took us a while but we got off his shoulder pads and stripped him till he only had an undershirt on top.

Next was the bottom half and neither of us wanted to do it. We both saw the bulge and didn't know if it was protective cup or his actual dick. We argued back and forth about who would do it.

Then my sister said, "Only one way to decide it then." She got her hands ready for a game of rock, paper, scissors and I followed. The first 2 games were a draw but I won the 3rd game when my rock beat her scissors.

"Best two out of three?" she begged.

"Fuck no. We always do best of one."

"Please. He's your friend. You should do it. I'll make it up to you later. Please."

"I don't want to touch another guy's dick. And you'll say you'll make it up to me now but when I come asking you'll pretend like you don't know what I'm talking up about. This is all you, Dani." I stepped back to let her do it.

As soon as she started tugging on his pants, I turned around not wanting to catch an unwanted sight.

I heard her struggling and I joked, "C'mon Dani, you should be an expert at getting a guys pants off."

"Shut up. I bet your pervy ass would enjoy seeing that."

The struggle went on for a few more minutes when I heard a gasp. A minute or two later, she said, "Done."

"You're not pranking me are you. I'm not going to turn around and see his dick."

"No."

I turned around and saw she had tucked Ray in to bed. We said goodbye to his grandma and left the house.

"I'll drive, I haven't had a drink at all. No reason to take a risk."

She tossed me the keys and we got in the car. She said, "Are you hungry?"

"Yeah, I really didn't have anything to eat. Stella's?"

"You read my mind. But will mom make dinner for us?"

"Nah, she probably spent all her time handing out candy."

The diner was filled with others who stopped by to get some food after the party. We found seats at the end of the counter and ordered a burger, shake and fries each.

"Sorry that my friend groped you."

"That's fine. Only because it was Ray. If it was Tyler I would've question whether he was actually drunk and smacked him across the face."

I chuckled and said, "Actually, I think Matt should be the one to be afraid of, not Tyler."

"Why?"

"When he's drunk, he is super horny."

"Thanks for the heads up," she said as she let out a little laugh.

We may argue a lot but like almost every sibling, we do have moments where we have good, long conversations. This was one of those moments.

I asked, "Why don't you move out? I mean I'll miss fighting with you and I know you don't have to go into the office everyday. But don't you want that freedom of living alone."

"I have been thinking about it. I even started looking at apartments in the city. Don't tell mom and dad though. With you leaving for college next year, they'll never let me leave."

"But you got to do you. Just bring it up casually and it's not like they can actually stop you. You're going to pay with your own money and you're an adult."

"Yeah, maybe in the spring. Don't want to deal with moving in the winter. Going back to Ray for a sec. Do you know who he meant by other ones?"

"Huh?"

"When he grabbed my boob, he said he liked mine better than the other ones. Whose boobs did he touch before?"

"Why do you want to know?"

"I want to know who he was comparing me with. Give me a little confidence boost. After all, no one is more truthful than a drunk person."

"I don't know if I can tell you."

"C'mon. You know I won't tell anyone. We've shared other secrets before."

"Fine, I'm not sure if he actually did touch them but he saw Felicity Jones' boobs."

"Eh, doesn't make me feel that good."

"What?"

"Her boobs aren't great. At least, the last time I saw her, they weren't."

"Still the same story. Meh boobs, phenomenal ass."

"Yeah, I can't compete with her ass."

Once we got our food, we polished it off quick. We didn't say a word to each other as we were both starved.

On the drive home, she asked, "What's that cute girl from church saying?"

"Sydney?"

"No, not Sydney. The other one. I don't know her name."

"Courtney?"

"Is she the blonde with the killer body? Little bit of a tan?"

"Yup, that's her. Why are you asking about her?"

"Because she's obviously into you."

"She is?" I knew that we were getting closer but I assumed that she just wanted to be good friends. Now that the though was in my head, I started wondering if I had a crush on her.

"You are so clueless. Pay attention next time you talk to her. She'll drop a million hints. It's no surprise you haven't seen it already. You are dumb."

"You had to ruin it. We were having a friendly brother-sister conversation and you had to call me dumb."

She smiled and said, "In an affectionate way."

"You can never call someone dumb in an affectionate way. It's impossible."

We went back and forth on that for a while till I put a stop to it.

I asked her, "You crushing on anyone?"

"Haven't been meeting enough people. That's part of why I want to move to the city. Go out more, meet more guys."

"Dating apps?"

"Tried it. Not my thing."

"Why? There's lots of people who meet their partners on dating apps."

"I know but I didn't have that kind of luck. All I met were horny guys looking to get off."

"Luckily for me, we just turned on to our street. So, I don't have to hear about my sister's sex life."

"I don't mind continuing the conversation once we get home."

"But I do."

We pulled into the driveway and got into the house. Our parents had already gone to sleep. We both felt disgusting and needed to take a shower. I let her go first since she got Ray out of his bottoms.

We tip-toed upstairs where I went to my room and she went to shower.

My cock had been aching since Zoe told me about her and Mr.Grayson. I had never jerked off thinking of a girl I knew personally before but my mind was going wild imagining it.

I stripped to my boxers, got the lube from my drawer and started masturbating. I didn't even last 2 minutes before I started cumming. It was easily the best masturbation session I had ever had. My cock shot cum in a high arch and it made a mess.

I basked in the feeling for a few minutes as I tried to fight off sleep. I ended up taking a very quick nap but I woke up when I heard creaking in the hallway. I figured Dani was done with her shower.

I carefully made my way to my bedroom door and popped it open just enough so I could peek. I saw no light coming from under the bathroom door, so I grabbed clean pair of boxers and slowly walked to the bathroom making sure I didn't leave a cum trail.

I took a quick shower and brushed my teeth. As I was about to leave, I noticed there was a bra on the floor. It was a white strapless bra that had to be Dani's. No one else except for the two of us used this bathroom.

I picked it up and examined it, mainly looking for a size tag that I couldn't find. I was still feeling a little bit horny from thinking of Zoe, so against my better judgement, I wrapped the bra around my cock and used it jerk off.

Since I had just did it not even an hour ago, it took some time but I eventually came. I did a quick inspection of the bra to make sure I didn't get cum on it and placed it back just like I found it. I hopped in the shower again to clean up and went to my bedroom.

Feeling great after ejaculating twice, I fell asleep as soon as my head hit the pillow.