The Jerk Off Folder

No one in high school compared to Kelsey. We were good friends but I couldn't deny that I was incredibly attracted to her. She had a cute face, with shoulder-length brown hair, big eyes, and an infectious smile. She was sweet to everybody in a genuine way. But as we got older and approached senior year, she just got hotter. Her shorts got shorter, her shirts got tighter. I couldn't help but stare.

One day at school, she pulled off her sweatshirt, unaware of her tank top clinging tightly to it because of the heat. As both garments were raised up, I remember catching a glimpse of her tight body and the edge of her bra. The waistband of her light blue panties just barely peaked out above her shorts. I couldn't handle it. I stared with my mouth open.

"You okay?" Kelsey asked.

I shook out of my dazed stare. She looked back at me innocently.

"Yeah, it's just hot today," I replied nervously.

"It really is. Come on, let's go to class!"

I couldn't stop thinking about her after that. As soon as I drove home, I got on my computer and looked at her Facebook and Instagram photos. Some of her at the beach, some of her posing in a flannel and yoga pants, which accentuated her slender legs. I desperately wanted to start jerking off to her. I usually couldn't because it made me feel weird. I would just resort to porn or celebrity photos. But this time I couldn't help myself. I barely lasted two minutes with Kelsey's photos. I cleaned up my mess and saved the photos in a folder, naming it "English Projects" as a cover-up.

Things changed when we had an oral presentation to do together in Biology. I was so excited when Kelsey walked up and asked me to be her partner. We arranged to meet at my house after school. Let me tell you, there's nothing better than opening my front door and seeing a pretty girl like her eagerly waiting for me.

We worked in my room. She made note cards while I made us a PowerPoint on my computer. I'll spare you the boring details, but I really did enjoy her company. It was also a major plus to see her lying down on my bed, scribbling on notecards. I did my best not to stare at her ass while it jutted out as she casually swung her legs in the air. Kelsey looked up at me.

"What? Something wrong?" she asked.

"No. Uh, I just find it kind of funny how comfortable you are here."

Kelsey giggled and sat up in the bed. She tossed the notecards at me.

"Get back to work, mister!"

I spun around in my chair and hit save on the PowerPoint.

"Look, I already finished! We just gotta do it tomorrow now."

Kelsey sighed with relief, leaning back into my bed.

"Ok, I'll get out of your hair now," she said.

I didn't want her to leave, so I got ready to make my move.

"Well hey, do you want to go hang out somewh-"

"-Wait, hold that thought. I almost forgot something!" She replied suddenly.

She nudged my chair away from the computer before I could say anything. She took her USB stick out of her pocket and stuck it into my computer.

"I just need to download the PowerPoint," she said innocently.

"I can do that for you!" I started to get nervous. I didn't want her to look through my computer.

She clicked away into my folders.

"Well it's not in your 'Biology' folder. Did it route itself here? 'English Projects'?"

"NO! Don't click-"

I stood up from the chair but I was too late. She opened it.

She stared confusedly at close to 20 photos of herself. I was mortified.

"Kelsey, I can explain!"

"What is this?"

"It's... I'm making... uh... a yearbook since I couldn't afford the school one. I... just needed the best photos of us and all our friends."

Kelsey looked more closely.

"And you decided to go with my bikini photos?" She looked at me for an answer with a smirk on her face.

She looked adorable at that moment but I couldn't be more embarrassed. I decided to fess up.

"Kelsey, you're one of my best friends and I like you a lot—"

"Do you want to fuck me?"

Her response took me completely off-guard. She said it as innocently as she said anything else, but I've never heard her say anything so naughty.

"I... uh..." was all I could muster.

She looked back at the computer folder, even she looked a little embarrassed. One of the adjacent folders was littered with porn.

"All of this is for... masturbating, right?" The word made Kelsey giggle a little bit.

"...Yeah." My face was hot red from admitting.

There was an awkward silence.

"...So do you want to fuck me?" She asked again with a straight face.

This time I couldn't answer. She moved quickly towards me. I expected her to slap me in the face.

But then she kissed me. I couldn't believe it. I wrapped my arms around her waist as we made out. She pulled herself away to look at me again.

"So...?" she asked impatiently.

"Yes. I do." I said in a stupidly eager voice.

"I like you too, dummie." She laughed at me again, but in a way that made me feel comfortable. We made out again as she ushered me towards my bed. She pulled off my shirt and started to unbuckle my pants.

"Are you sure? I'm a virgin." I couldn't help but be honest.

"We're 18, it's time," she replied.

She yanked my pants down to the floor. She pulled off her top, revealing her light blue bra. I put my thumbs into the waistband of her short shorts. I could feel the fabric of her panties.

"Not yet." Kelsey smiled teasingly.

Kelsey grabbed both my hands and slid them up her body, ending them on her petite breasts. I immediately got rock hard. My erection shot upwards, barely grazing against her belly. The slight contact makes Kelsey giggle again.

"Someone's happy!" Kelsey said, staring down at my boxers.

She pushed me further into the bed and put her hands eagerly around my underwear.

She pulled off my boxers, revealing my hard cock. She smirked at it. I started to get defensive.

"I know it's not that big—"

"It's not that bad," Kelsey replied, nodding honestly. She smiled and put the tips of her fingers on my erection. She stroked it up and down twice. My dick twitched just from her slight contact. I groaned. Kelsey giggled as she pulled off her short shorts, revealing her matching light blue panties. All I could do was stare at how her panties clung tightly to her crotch, revealing a hint of cameltoe. I was mesmerized with my mouth wide open. Before I could think about how this could get any better, she mounted on top of me.

The sensation of her body grinding against mine felt incredible. I could feel her boobs press against my chest as she gyrated back and forth. My erection slid continuously against the contours of her panties. I could feel myself against the slight crease of her pussy. It took everything in me not to cum at that moment. I then realized just how terrified I was. I desperately wanted to fuck her, but I wanted to satisfy her, too. She took notice of how anxious I was getting.

"Are you okay?"

"I don't want to disappoint you."

"You won't. I want you." I couldn't believe her words, yet here she was, right on top of me. Kelsey guided my hands from her slim waist to her hips. I could feel the shape of her ass as she moved my hands into her panties. Together, we pulled off her panties as I felt every inch of her perfect legs on the way down. I took in the sight of her tight shaved pussy.

"I can't believe this is actually happening," I said.

"Are you ready?" She asked with a cute and seductive smile.

Kelsey gently guided my dick with her hand. Again, her grip made me twitch and I was afraid of cumming immediately. I tried to think of other things, but I ended up watching it all happen. She was already slightly wet, so my dick slipped inside her with ease. She moaned upon insertion. It had to be the sexiest sound I've ever heard. Our bodies pressed against each other again, but this time I felt the warm tightness of her pussy. The feeling was a thousand times better than I could've imagined while jerking off to her.

We both moaned together. I felt up the rest of her tight body while she unhooked her bra, revealing her petite breasts. I squeezed them, causing her to moan quietly. Kelsey arched herself downward, our mouths breathing heavily against each other. We kissed again. I couldn't stop thinking about how I was having sex with my high school crush. I could feel her pussy tighten around my cock. It felt so good that I knew I was going to cum in the next ten seconds.

I could feel my orgasm climbing. I didn't have much longer. I knew I was going to disappoint her, so I ashamedly began to pull out. Kelsey stopped kissing me after taking notice. She watched as I slid myself out of her. I looked at her apologetically, seconds from orgasm.

But then Kelsey gave me her classic smirk once again. She grabbed my dick and slid it as far into her pussy as she could. I couldn't handle it anymore. Spasm after spasm shook through my whole body until I finally came inside her. It was unlike anything I've ever felt. I gave out my orgasm moan, a sound no one else has heard until now. Kelsey smiled as she felt my warm cum shoot up inside her. She collapsed her body on top of mine, my dick still in her pussy. I could feel it slowly getting softer.

"Oh my god," I sighed exasperatedly.

"You're welcome," Kelsey replied, giggling. She climbed off and laid down beside me.

"I'm sorry I didn't last very long... I'll make it up to you" I said, getting up.

"No, don't. It was nice. I really enjoyed—"

Kelsey suddenly gasped. I had stuck my fingers into her still wet pussy. I rubbed it in a circular motion, finding her clit.

"mmmmhmmmmm."

She moaned in a quiet reserved way that felt real. She was getting wetter so I dove in with my tongue and started to eat her out. Her moaning started to speed up, she had her hands in her hair. I kept going until finally she let out a soft high-pitched yelp. She immediately cupped her mouth with her hand, as if embarrassed by the noise. Her legs shook around as she continued to orgasm. I kept licking away at her juices, prolonging her orgasm as long as I could. After a few more seconds, her body finally rested down. Kelsey took deep breaths until she finally began to calm down.

"I've never made that noise before," she whispered, her face a little red.

"I was just returning the favor."

We laid down there together for a while, my arm around her until we were both completely relaxed.

"I should go home now."

We both got up and started to get dressed. While she put on her shirt, I picked up her panties. She started to reach for them but I interrupted.

"Uhh, could I actually keep these?" I asked nervously.

"Okay..." Kelsey giggled.

I watched her slide on her short shorts, her bare ass clinging to them as she tried to slip it on. The denim of her shorts must've been pushing right into her pussy. I could already feel myself getting hard again.

Kelsey was tying on her shoes when she looked up at my crotch.

"Already?" She asked with a smirk.

"I can't help it!"

"Well... I'll help you get started then."

She set me down in my chair and yanked off my boxers again. My erection flung out again. She kissed the tip of my dick, then put it inside her mouth, looping her tongue in a circle around the head. I rolled my eyes with pleasure. I let out another moan. She slid her mouth off my penis with a slight popping noise. She smiled as she got up to leave.

"Kelsey... please..." was all I could muster.

She spun my chair around, making me face my computer. She opened up one of the photos of herself.

"Have fun!" She laughed adorably, then kissed me on the cheek. She closed the door behind her as I started to jerk off.