Getting in with my best friend – The Tutor p.1 – Short Sex Story

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I wasn’t expecting this. As a matter of fact, I would’ve never wondered I would be experiencing this to start with. I felt her press her warm body against mine and thought if I had been dreaming.

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This story takes place as the result of an encounter. An unexpected, but highly enjoyable one. To give you some context, let’s begin with me. My name is Isaiah. I’m 18 years old, and just a couple of weeks from finishing senior year. Now before I go ahead, let me preface: I’ve never been trendy – at least for the things you want to be trendy for. I’m kinda nerdy, and one could say it isn’t hard to tell.

Keeping this in mind, you could probably guess one facet of teenage life it didn’t help me with: dating. Growing up, I never really had friends. More so acquaintances. It was an crucial distinction I had to make.

I got to know them a little, though. I had seen some of them go from extremely shy to extremely confident dudes, and get girlfriends the moment they started looking. Others were at all times confident and could pick up any girl they wanted.

Not me though. Pretty much never even a pick. I had only one person in my life who I would consider a real friend though. Kayla. She just so happened to be a girl. We were the same age. We had met in middle college and had been friends ever since.

She was so clever, one of the smartest people I’ve ever met. She’s my best friend. She’s been with me through thick and thin. At all times there when I needed help. Made me feel like I wasn’t alone. We would talk for hours and hours over the phone.

It seemed like forever, having long, deep conversations about the meaning of life and existence and all that philosophical stuff. I felt I had really connected with her all these years and planned on asking her out, but decided against it. I didn’t want to ruin our friendship. Before you say anything, no, nothing ever went on between us. Anyway, apart from her, I had other interactions.

Casual conversations. Small talk.

“Got plans for the weekend?”

“What’d you get on Mr. Emerson’s math final?”

“Going to see that new movie?”

Stuff like that. The only thing I really did outside of college was the tutoring I did every weekend. Yeah, I’ve had a real knack for math since I was a kid. Signed up to become a tutor at my college freshman year.

Word got around that I was really good in Trigonometry and Calculus, even better than the other tutors grades above me. Stuck with me ever since. For better or for worse.

This was the only real one on one time I’d spend with people, especially girls, both in college and out of college other than Kayla. Everybody knew me as that guy you want to go to. It’s a gift, I guess. So I tutored. I was basically never free for any social event on the weekends because of my tutoring. I took appointments. Made a company out of it. Had an app I used that let me keep track of appointments I had. In any case, it was gonna look really good on my school apps.
This particular day was a Thursday. I was free today. I would call it strange, but that day was our championship football game. It was highly anticipated, of course. Everybody and their mom was planning on being there. Homework could wait. And here I was, walking home with no plans. Once I did arrive, I got undressed, and got settled in my bed.

My parents were both at work. It was early. Only 3 pm. I was planning on just calling it a day. Bored out of my mind, I went downstairs and turned on the tv. Put on FX, and just sat there for what was only minutes. I nearly fell asleep before I was jolted awake by an alert from my watch. I was booked for an appointment. Why on such short notice? I wondered to myself.

I looked at the details of the notification. Kayla Tomlin. 12th Grade. Trigonometry Help. 6 pm. I recognized that name. Why didn’t she just text me? It was 5 pm now. Sun was already starting to set. We hadn’t hung out in a while because of my schedule.

I at all times made time for her, but this semester was really difficult. I was free though. I got dressed and called an Uber. I waited about 10 minutes. We drove past the college where the crowds were already gathering for that night’s oncoming event. Bright white lights illuminated a rich green turf and silver bleachers.

We passed by the Kwiki-Mart where Kayla and I would hang out after college most days after college when I wasn’t tutoring. I arrived at Kayla’s house a little after 5:30. We parked at the address on my GPS. 464 Henderson Lane. I almost forgot how nice her parents’ place was. It had a perfectly trimmed lawn and sculpted shrubs. Little ground lights lined the walkway leading up to her house. After I left the car, I walked down the path and hopped up the steps and gave a quick knock on the door, and after about a minute, Kayla opened it.

“Kayla?” I said.

“You look kinda different.”

She was wearing a silky white, plunging neck lace dress. Something she would never wear. She gave me a quick smile and nod and let me in the house.

“Hold on, I have to go upstairs to grab my stuff.”
I sat on the couch in the living room and waited for a couple minutes. I noticed the pictures of Kayla and her parents along the living room wall. I knew Kayla’s parents very well. Back in in day, they would take me on camping trips with Kayla. My parents knew them too so it was all good.

Kayla’s mom, Mrs. Tomlin didn’t like me so much when we first met about 6 years ago. It took some time, but she came around, eventually. As I was lost in wondered, my stomach reminded me of its presence.

I hadn’t eaten yet, so I made my way to the fridge to grab myself something to eat. I was finishing a bowl of cereal when Kayla came down with her Trig books, her homework and a notebook. She had on makeup. I knew she hated wearing makeup because, years ago, she said to me one day:

“it reinforces society’s fixation on girl’s appearances instead of their intellect.”

I loved playing devil’s advocate, and so I challenged her belief. We debated the topic for hours and we never noticed. Good times. I had also noticed she had straightened her hair, a stark difference from her characteristically wild hair.

“Hey um, why didn’t you just text me?” I said.

“Well I could’ve, but I felt like being quirky today and checking out the scheduling app. You responded, didn’t you?”

“I did. You wanna get started then?”

“Ready when you are, Izzy.”

It was pretty early. The appointment was for 6 and it was 5:45. I took a look at her problems and asked her questions, and we worked through each and every one. I guided her and had her rewrite some notes she misinterpreted. It was tedious, and she wondered it was unnecessary. I assured her this would help her in the long run. By 8, we were on the last row of questions on her second homework assignment.
“So you take the cosine and multiply it by the hypotenuse to get the input for X. Take the input and substitute it into the other equation for the final solution.”

“Dude, I thought you were good at this!”

I frowned. “Relax, I’m just busting your balls!” She took a moment and sighed.

“I hate sitting around the table, but it has the best lighting in the house.” Kayla said. “Let’s go up to my room, it’s way more comfortable.”
Thinking nothing of it, I followed Kayla up the steps and to her room. We worked at her desk underneath a bright lamp and spent some more time on the last of her Trigonometry homework.

“I think I got it now,” she said.

I was pretty tired at that point. Barely having slept and only eating a bowl of cereal since I got home from college hours before. I sat up from the chair beside her and rose to stretch.

“Damn, Kayla. You could’ve just asked me for help normally you know. I’m so beat right now it’s not even funny. Glad I could help though.”

I turned to leave when Kayla stopped me.. She said she didn’t just ask me here for homework help. She pointed to the bed.

“I want to talk to you about something.”

My brow furrowed. This was very unusual. She never let me on her bed before. I was worried. I wasn’t sure if something was wrong. She knows she can tell me anything. I gently laid on her bed.

“What’s going on?” I said. The expression on my face made her laugh.

“Calm down, Isaiah. Nothing’s wrong. She inched a little closer to me.

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“There’s just something really important I’ve been meaning to tell you.”

I turned my body completely to face her.
At that moment I felt a sensation but I wasn’t sure what.
“I’ve felt something about us for the longest time now, but I just haven’t been able to find the right words to describe it…until now. We’ve known each other for so long now, and I feel so comfortable with you.”

I noticed her shifting even closer to me, so our faces were inches aside. She continued to speak gently:

“I just feel like I don’t have to put up a wall when I’m around you. You make it feel so…natural…I don’t know how else to describe it. All those years ago, I never knew you liked me. I never knew you wanted to be with me.”
I stared intensely in Kayla’s deep, dark, brown eyes. I couldn’t believe what I was hearing.
“But I understand now. I didn’t see the signs then but I do now. I feel the same way.” She said softly.

She moved and started to get on top of me.

“Kayla…”

She shushed me. “Don’t say anything, Isaiah. I want you.”

She looked at me, I slowly nodded my head. She started kissing my neck softly. I began to feel hot. She started caressing my face as she was kissing me. I felt her touch tingling all over. She made her way over to my cheek, and then to my lips.

“I’ve wanted this for so long, baby.”

She kissed me deeply and passionately. I wanted this too. Her lips felt so good on mine. Soon, our spit started mixing and making our lips wet. She slowly pushed her tongue in mouth. My eyes rolled into the back of my head. My tongue entered her mouth and it danced with hers. She pulled away from the kiss, and a long stared of saliva extended from her lips to mine. She began slowly pulling on the shoulder ends of her dress. She pulled them all the way down to reveal her plump, round breasts. They had little freckles on them, and her nipples were hard and erect in the middle of her pale brown areolas.

“I don’t usually wear something like this, or even put on makeup like this, but I wanted to look good for you…do you like it?”

“I love it, Kayla.”

She pulled up my shirt to reveal my bare chest, while I pulled off the rest of her silky white dress. She was in matching satin white panties. She lifted up her legs, and slowly pulled them off to reveal her beautiful pussy. I felt my member throbbing. Kayla looked at me and said:

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“I can tell that you like what you see…” I nodded my head slowly.

She took her hand and started rubbing my crotch.
“I can feel you getting hard for me,” Kayla said with a smile on her face.

She unzipped my pants and my member sprung free from my pants.

“Wow…” Kayla said. “It’s even bigger than I thought.” She stroked me slowly.

I never wondered I’d hear that before.

“You like that baby?”

“Yes…” I said, with increasing exasperation.

“Can I…suck your dick?” Kayla said.

I looked her dead in her eyes and a enormous smile grew on her face. She slowly lowered her mouth on my thumping member.

“Oh God…” I whispered.

Kayla started sucking on me faster and deeper. Waves of pleasure flew over me with every motion. I moaned.

“Oh Kayla!”

Kayla made increasingly noisier sounds. Slurping. Sucking. She lubricated me. I knew something I really wanted, though.

“Wait, baby!” She took me out of her mouth with a pop noise.

“I wanna eat you out.”

Kayla grinned. I moved and she laid on the bed.

“I’m ready, baby.”

“I can’t wait to see how you taste,” I said.

I licked her labia, and then I thrust my tongue inside of her. I worked my tongue all around her pussy. I made sure to pay special attention to her culture. I licked it. Kayla writhed in pleasure.

“It’s so sensitive, Izzy,” Kayla said.

I started to suck her clit. It got harder and harder for me. Kayla was moaning so loud. It made my member throb even harder. I didn’t wanna make her cum yet. She had the same idea.

“Wait, baby. Don’t make me cum yet,” She said in between breaths. “I want you underneath me.”
We switched. Kayla stopped and slid her body on me. I could feel her breasts as they made their way closer to my chest. Her hard nipples dragged across my skin. I felt her face right beside mine, and her pussy adjacent to my member. This wasn’t what I was expecting. As a matter of fact, I would’ve never wondered I would be experiencing this to start with. I felt her press her warm body against mine and thought if I had been dreaming. Kayla moved her mouth next to my ear and whispered carefully:

“I want you inside of me.”

I quickly exhaled.

I felt Kayla gently grab my member and position it. She lowered down on my member and exhaled. I was fully inside.
“Isaiah…I feel you pulsating inside me…”

Kayla rose up and slammed back down on my dick. I moaned. As she rose up again, I moved my hips upwards as she came down to me her halfway, and it made a telling smack sound. I could feel her wetness on the base of my member. We started moving faster and faster, and moaned louder and louder. Her breasts swayed rhythmically with each penetration.

“YOUR PUSSY FEELS SO GOOD, KAYLA!” I screamed.

She was riding me cowgirl style. I couldn’t contain my pleasure. She stopped and grated her hips on my throbbing member, causing me to tingle all the way down to my toes. I didn’t want her to stop.

“Kay, I want to see your ass bounce,” I said sensually.

Kayla stopped and smiled. Spinning around on my dick to face backward.
We started back up again. Kayla’s gorgeous ass bounced up and down on me.

“How does my dick feel, baby?”

“FEELS…SO…GOOD! I WANT YOU ON TOP OF ME ISAIAH!” Kayla screamed.

She stood up and my member flopped out of her. I rose from the bed and stood on the side while she laid flat on her back for missionary style. She looked at me with a giddy expression.
I got on top of her and looked at her knowingly.

“Do it, baby.”

I could feel the sweat rolling down my back, and beads of sweat all over Kayla.
I slowly inserted my member inside of Kayla. She let out a deep moan.
We started fucking harder and faster than ever before. I could feel her pussy tightening more and more with each thrust. Kayla was crying out for me.

“OH GOD ISAIAH YOU’RE FUCKING ME SO GOOD!”

Her moans motivated me to thrust even harder inside of her tight, wet pussy. I turned to look behind me, I could see her toes curling.I smiled.Kayla couldn’t take it. She was shaking her head from side to side. Going crazy from the pleasure. Her hands were on my head, squeezing my hair. I went in to kiss her. She kissed me back with longing. I slipped my tongue deep inside her mouth as we had done before. I continued thrusting deeper inside her as we kissed. We pulled away from the kiss. I looked deep into her eyes as I pounded her. She held my face as my member moved in and out of her, making Kayla spray more of her juices onto me.
“I want you to do something for me, babe,” Kayla said as I held her soft breasts in my hand.

“I want you to cum inside of me.”

“Do you really want me to?” I whispered excitedly.

“Yes, baby,” Kayla said. “Please babe, I just want you to explode inside me. I want every last drop baby!”

I sped up my thrusts and pushed as hard as I could. Kayla moaned even harder and was even louder than before. I was getting close.

“YES, ISAIAH! KEEP FUCKING ME! PLEASE BABY DON’T STOP!” Kayla screamed.
I squeezed on her breast and fondled her nipples more intensely. At that moment, all the feelings I had, all the sexual tension, was about to be released. I couldn’t contain it any longer.

Kayla was about to cum.
I was about to cum.
Kayla’s legs and arms wrapped around me tightly.
“I’M GOING TO LET IT ALL INSIDE YOU BABY! EVERY LAST DROP!”
I had the greatest orgasm of my life inside of Kayla.
We were both groaning from the pure intensity of it all – the exhaustion.
We both breathed heavily as we gazed into each other’s eyes.
“I’m so in love with you, Isaiah.” Kayla sighed.

I kissed her passionately and said: “I love you too, Kayla.”
As I was moving to pull out my aching member from Kayla’s soaked pussy, she stopped me.

“I want you to stay inside me. I want this moment to last forever.”

I smiled and pushed my dick into her. She let out a soft moan.
Just then we heard the clacking of keys against a door.
Her parents were home from work. I checked my watch. 1 am. I became worried and swiveled my head to Kayla’s bedroom door.

“Don’t worry babe,” Kayla said. “They’re probably really tired. They’ll head straight to bed.”
I turned my head back towards Kayla.
“Ok,” I said in a hushed tone.

I still had the wondered of them bursting in the room, seeing me fully inserted in their daughter. I rested my head in the nook of her shoulder. Our bodies clinged to each other because of the sweat. It was perfect.
We fell deeply asleep together that night, with my member nestled deep inside her, coating her womb with my cum.
7 am. Friday.
The morning rays guided us out of our slumber.

As I rose, Kayla said: “Morning, babe. Sleep well?”

“Best sleep of my life,” I said.
Kayla suggested I sneak out of the house then knock on the door, asking the Tomlins’ for a ride to college. We ended up taking the bus. I knocked on the front door and Kayla’s dad opened the door.
“Hey, Isaiah! Pretty early in the morning, you live all the way across town!”

“HI, Mr. Tomlin. I was just wondering if I could have breakfast with you guys until the bus comes for us.”

“Yeah, come on in Isaiah. You know you’re always welcome here!”

Mr. Tomlin was already making breakfast in the kitchen when I joined him. Mrs. Tomlins came downstairs a few minutes later with a warm “Hey, how ya doing sweetie? School going okay?”
Kayla came down to join us around the kitchen table. Her hair was frizzy and wild again.
“Hey honey, Isaiah’s here to join you on the school bus!”
Kayla gave me a knowing smile.
We ate a delicious breakfast for the bus.The bus arrived at 7:45. We sat next to each other of course, and held hands on the way there. We got to college at 8.Walking into college, people were in bright spirits. Spring break was next week, and we won this season’s championship 56 – 15. Some students had our mascot’s colors painted on their bodies. Blue and white – the Scintillating Sharks. The college day started, and Kayla and I parted methods for the time being. I progressed through the day, but all I could think about was her. I know she was walking through the halls with pieces of me swimming inside her. In biology class, I talked to an acquaintance of mine.
“Did you go to the game last night? It was wild!”

“No, I was kinda busy, Ryan. You know, tutoring again”

“How could you have possibly missed that shit bro? You’re tweaking for real for real!”

I simply shrugged. Ryan turned to another classmate.

“This dude seriously missed the game to TUTOR.”

He turned back to me.

“I hope that shit was worth it bro!’
I looked down and smiled.
After college, Kayla and I walked to our local park, the Town Greene. We sat on a swing bench, held by a thick tree limb attached to a massive, great oak. I held Kayla in my arms. We didn’t say anything.
After a while, Kayla goes: “Isaiah, what are we?”

“Do you want to be my girlfriend?” I ask.

“Aren’t you a tutor? You should already know the answer to that,” she replies.
I smiled, and we embraced each other with a deep kiss. We started dating. And as the days passed our love for each other only grew stronger. We had our fights. But our bond developed deeper, both physically and emotionally. Spring break passed. Finals passed. And then we graduated. We both planned on gonna the same school so we could day together. We could make long distance work, but we could never stay away from each other for long.

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One day, a couple weeks later, Kayla told me she had missed her period. We quickly went to the Kwiki-Mart and picked up a pregnancy test. We got back to her house, and I waited outside the bathroom in front of her room. When Kayla came out, she had tears in her eyes. Happy tears. She was pregnant. I wasn’t shocked. She had decided not to take the morning-after pill, and I agreed with her decision. I was in love with her. Maybe not the best timing. We were fresh out of high college. About to enter school.

But it didn’t matter.
We could do it.
We were young, and I wasn’t sure if I was prepared to be a father.

With Kayla by my side though, I knew I had the strength.
I’m so glad I didn’t have any plans that night. Just my regular.
The Tutor

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btw, my first post on this subreddit!

NSFW: yes


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