The Jerk Off Folder Ch. 02

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My high school crush shares the news with her friends.
3.1k words
4.59
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Part 2 of the 3 part series

Updated 06/08/2023
Created 06/02/2017
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Despite having found out that I masturbate to her, and despite the fact that we had sex just a couple days ago, my friendship with Kelsey felt just the same as it was before. I was lucky she didn't think I was a freak for jacking off to her. But nonetheless, two days had passed and I desperately wanted her again. When the weekend finally came, Kelsey was ready to address what happened. She sent me a text: "My family's gone this Saturday. Having a party. Wanna come? I told my friends about us!"

I quickly said yes, incredibly excited. I wanted us to be official and I was glad she was willing to tell her friends about us. On Saturday, I walked over to her house and rang the doorbell. Kelsey answered the door. She was dressed in a girly-fit Disney t-shirt with blue skinny jeans that cuffed several inches above her ankles. It was a stunning combination of both cute and sexy. Although she wasn't showing too much skin, the outfit accentuated her tight body.

"Hi! How are you?" she asked with an eager smile.

"Much better now," I said while eyeing her up and down. I couldn't resist. Kelsey laughed, noticing that I was checking her out.

"Come on in. Carly and Kate are here."

We went straight through the house and into the backyard. It was modest-sized with a patio and a fairly large pool.

Carly was lying down on the outdoor couch. She had short auburn hair that went down just to her chin. She was wearing sunglasses and was already sporting a black bikini. She had unreservedly propped her legs against the armrest of the couch, not even bothering to cross them. I did my best not to stare for too long.

"Hi Carly," I greeted casually.

"Hey. Like what you see?" Carly asked. She stretched her arms in the air, then slowly brought them down, sliding her hands along her slim body, and brushing against her small but perky boobs. I must've stared a little too long because Kelsey nudged for me to move along. Carly adjusted her sunglasses with a sly smirk on her face. She knew she was hot.

Kate sat with her feet twiddling in the shallow end of the pool. She was dressed in a white tank top with dropped armholes. Her red bikini bra shown through the sides. She was a bit taller than Kelsey, with long golden blonde hair and a soft smile. Kate was a bit older than us and was already in her second year of college. She looked over at us approaching. She looked down at my t-shirt and jeans with a frown.

"You didn't bring trunks, did you?" Kate asked. I looked over to Kelsey.

"Sorry, was I supposed to?" I asked nervously.

"Typical Kelsey. You forget literally everything!" Kate exclaimed jokingly. That got me to laugh a little bit. It was a regular thing for people to tease Kelsey.

"I wanted to watch a movie today. You guys are the ones that went straight for the pool!" Kelsey replied, defending herself. Her voice adorably got a little higher whenever she argued.

"It's hot. It's nearly summer. There's no way I'm NOT going to the pool. Even if I have to hang out with you losers," Kate joked again.

"Well at least I'm not the college kid that still spends time with high schoolers," Kelsey retorted. That prompted me to give her a high five. Kate got up and pulled off her tank top, revealing her red bikini in its entirety. The C cup bra held her boobs with slight cleavage on top. She unbuttoned her shorts and dropped them to the floor, revealing the bikini's tight bottom half. Her bottoms were held together only by two small knots strung beside her hips. I tried my best to maintain eye contact and not stare at her, too.

"Well, I'm going in," Kate said, and jumped straight into the pool. Some of her splash got into Kelsey's eyes, temporarily disorienting her. Kate seized the opportunity and grabbed Kelsey's leg. Before Kelsey could realize what was happening, she was yanked into the pool, fully clothed. Kelsey let out a high-pitched scream.

Kelsey emerged from the water, pulling back the wet hair from her eyes. I expected her to be mad, but she was laughing.

"You're lucky I don't have my phone," she remarked to Kate.

"Get those jeans off before you ruin them, girl!" Kate replied.

Kelsey shimmied around in the pool, trying to pry off her skinny jeans. As she splashed around, I could see her light green cotton panties peeking out. I wanted a better look but she kept squirming around, her jeans stuck around her knees. Kelsey looked over to me with an innocent smile.

"Get in!" she called over, playfully.

I took off my shirt and jeans. My plaid red boxers would have to do as swimming trunks. Carly passed me on her way to the pool. She glanced at my boxers with a smirk before diving in. I tried not to think anything of it, then jumped in as well.

Kelsey finally propped herself up onto the edge of the pool. She kicked until her wet jeans finally shook off. I could now get a better view of her. Her drenched grey shirt was sealed tightly against her body, not leaving much to the imagination. It fastened itself to the slight curves of her slender waist. The pool was cold, so I could just barely see her hard nipples peeking out of the fabric of her shirt. I didn't know she wasn't wearing a bra. I could feel my erection starting to grow. My eyes continued to trail down her body.

Her bright green cotton panties were still soaking wet, with her butt creating a cute puddle on the warm pavement. The panties clung tightly to her crotch, providing a perfect outline of her lower body. The panties had little black butterflies printed all over. Carly whistled at Kelsey.

"Cute panties, Kelsey!" Carly yelled.

Kelsey blushed and covered her panties with her hands. Her embarrassed pose made me even harder. I started to think about her pussy and wanted to be inside her again. Kelsey finally dropped back into the pool and swam towards me.

"How you doin'?" Kelsey asked, smiling. The red in her face started to fade.

"I'm good. Pool's a little chilly though," I said, trying not to stare at how her shirt was shaping itself around her boobs.

"I'll warm you up," Kelsey replied, giggling. She swam over and put her arms around my neck. Water splashed around as Kelsey swung her legs and wrapped them around my waist. As the water around us began to settle, her butt slid against the tip of my erection. She gave a cute and light gasp, surprised by the sudden contact. Her quiet gasp coupled with her crotch against mine was enough to make me leak some pre-cum. I tried to hide my moan and hoped the other girls didn't notice what was happening.

"Whoa, don't get him too excited!" Kate called over to Kelsey. Carly started to laugh.

"He's probably getting so hard right now," Carly said.

Kelsey smirked teasingly and swam backwards and away from me. She spun around and faced one of the ladders behind her.

"I'm gonna go get a towel," Kelsey said, giggling.

She climbed up slowly, the back of her light green cotton panties clinging to her ass as it emerged from the surface of the water. After that, came her shiny legs. Water droplets from her panties cascaded all the way down her long legs with every step up. She finally got out and walked along the edge of the pool, dripping wet. I could only stare with my mouth open. I wanted her so badly. But then suddenly, I felt something feel my penis. I gasped.

"Ooh! He is hard!" Carly teased.

I spun around to find Carly right behind me. Startled, I nudged her away and started to swim towards the other end of the pool.

"Hey, come back! I didn't get a good look at it yet!" Carly called over. I didn't know why she was being so handsy. I looked around for Kelsey to help, but she had already disappeared into the house. Carly chased after me as we essentially did laps around the pool.

I had to rest my arms against the edge of the pool, tired from all the swimming. Suddenly, Kate grabbed onto my shoulders from outside of the pool.

"I got him! Take off his boxers!" Kate yelled to Carly.

Carly finally reached me and put her thumbs into the waistband of my boxers. I struggled but together they held me back. Carly yanked off my boxers and tossed them into the grass. I couldn't believe this was happening. I swerved over to the center of the pool, maintaining my distance and hoping the water distorted their vision.

"Oh come on, why so shy?" Kate teased.

"Yeah. Don't you jerk off to us, too?" Carly asked. The two girls erupted into laughter. I could feel my face starting to turn red.

"Kelsey told you about-?"

"-She told us EVERYTHING. You didn't know?" Kate answered, still laughing.

I couldn't believe her. But then I thought about Kelsey's text again: "I told my friends about us!" She didn't mean us being together, she told them about the whole jerk off folder incident. I was mortified.

"Come on, let us see it!" Carly shouted.

I had no choice. I faced my back to them and climbed the ladder as fast as possible. They made whistling noises at the sight of my ass. I quickly turned around and covered my still hard cock with my hands. The girls had both emerged from the pool and moved towards me, cornering me against the wall.

"I wanna know if Kelsey was right!" Kate teased.

"Yeah, she must've exaggerated the size if you're so nervous about showing us," Carly said with a smirk.

"If you can show it to Kelsey, you can show it to us. You were confident enough to jack off to her, weren't you?" Kate reasoned, trying to hold back her laughter.

"Ooooh Kelsey... mhhmmmm... You're so hot... ughhh," Carly tried to imitate my voice while stroking the air in front of her crotch. My face was burning red. I didn't know what to do. I resorted to removing one hand so I could move Carly out of the way. They could see a little bit of my dick as I pushed past her and ran towards the house. They started to whistle at me again but didn't chase.

"How big was it?" Carly asked Kate.

"Hard to tell. It's in the average range for sure," Kate laughed.

I was able to grab my shirt off the edge of the couch, but my jeans were too far away.

"What's going on, guys?" Kelsey had just emerged from the house with a towel. She took in the sight of me running naked towards her. She looked shocked, but then started to giggle. I was so embarrassed so I just sprinted right past her and looked for a room to hide in.

"What happened?" I could hear Kelsey ask the girls. There was still laughter but I could hear a hint of concern in Kelsey's voice. I heard her walk back inside and look for me.

Kelsey quickly found me in her room, with nothing but my shirt on to hide my erection. She smirked as she walked towards me.

"This isn't funny," I said, annoyed with her.

"From the looks of it, I'd think you're enjoying this," Kelsey said, smiling at my erection. I pulled my shirt a little further down to cover it better.

"Why would you tell them that I jerk off to you?" I asked, still mad.

"It's part of our story. I couldn't leave it out. And I needed someone to confirm I wasn't crazy for thinking it was sweet that you masturbate to me," Kelsey answered honestly.

I started to loosen up. It was hard to stay mad at a girl like her.

"Can I make it up to you?" she asked.

"I don't know. Maybe I should just go home and I'll see you another—" I suddenly gasped. She had her hands around my dick.

"You're so hard down there... Maybe I could calm you down... Then you'd be willing to still hang out with us?" Kelsey asked with her signature smile. She stroked lightly along my shaft in a spiral motion. I shivered with pleasure.

"...yeah," was all I could say. Kelsey giggled at my response. She knew I was crazy for her.

We started to make out. I ran my hands through her hair which was still wet from the pool. She didn't have time to change either. I rested my hands on her ass, which made her jump a little with excitement. I hooked my thumbs into her panties. They were still a little damp and pressed tightly to her skin. It was just one thin layer away from her perfect pussy. I could see the fabric of her panties clasping tightly into her slit. It was begging me to shove my dick inside. Kelsey suddenly grabbed my hands and stopped me.

"Let's not straight-up fuck while we have company here," Kelsey decided.

"Please... I want you," I begged her.

"Don't worry, silly. I'll still give you something," Kelsey replied seductively. She walked to the end of the room to close the door. As she leaned in to swing the door shut, her ass protruded towards me, putting a full view of her wet panties on display. I couldn't take it anymore.

I walked over and pushed her against the now closed door, and started to grind my dick against her panties. She gave an adorable startled yelp at my surprise contact, but then immediately got into it. She started to moan playfully, swaying her ass in a circular motion around my erection. She grabbed my hands and slid them under her shirt, positioning them on her waist. Her entire body was still wet. I'd never been so turned on. I slowly and desperately thrusted my dick against the underside of her panties.

"Mhhhmmm I bet seeing me like this in the pool drove you crazy," she teased quietly.

"Yes..." was all I could say between my moans.

She raised my hands further up her shirt and placed them on her petite breasts. My dick twitched with sensation.

"I bet it was even better than if I just wore a bikini," she teased.

"Ughhh god, yes..." I whimpered back.

I was harder than ever now. I groped one of her tits while using the other hand to feel up the rest of her tight body. Her moans started to sound more real rather than just to tease me.

"Mhhhmmm I could see you staring at my panties the whole time. How tight they were after getting so wet," she kept on.

"Ye—" I was about to answer but suddenly groaned. Kelsey had brought my hands down to the front of her panties. I started to rub around the front of her crotch and along her inner thighs. She let out a soft yelp. I was starting to leak pre-cum again. I wanted to cum so badly, but I really wanted her to keep going.

"Mhhhmmm... I want you... Mhhmmm... -ah..." Kelsey moaned on. She timed each pleasuring noise with every slow thrust against her panties. I wished I could pull them off and feel her pussy. As if on command, Kelsey guided my hands and slid them over her soft cotton panties and down to where they covered the crease of her pussy. Once. Twice. Then on the third slide, she slid my hands into her panties and let me feel the inside of her tight pussy. She felt incredible. She was wet inside from all the grinding. Her pussy was nice and warm compared to the cold temperature of the pool. I could feel her start to tighten around my fingers.

"Mhhhmmm -ah... -ah... You feel so good..." She whispered sensually.

I could only moan in response. I was too breathless to speak. I started to grind more forcefully against her, my dick sliding along her ass and to the edge of her pussy. There was nothing but cotton fabric between us. I could feel my orgasm climb at a rapidly fast rate. I didn't know how much longer I could take.

"Mmmhhhmmm... I want your cum. Cum for me. Cum. Please..." Kelsey pleaded quietly.

I climaxed immediately with my last thrust. Spurt after spurt shot out of my dick.

"Ohhhh my GOD!" I tried my best to yell under my breath so the others wouldn't hear me. The first portion of my load coated the back of her panties, some landing on the door. The rest trickled down her perfect legs and worked their way to the carpet. Kelsey giggled with satisfaction. She turned around to face me and leaned her head against mine.

"That was sooo good," Kelsey sighed, smiling. I couldn't agree more, but I was too exasperated to say anything. Kelsey laughed and took my heavy breathing as an affirmation. She gave me a quick kiss, playfully biting my lip. It all felt like a perfect moment.

Then suddenly, Kelsey dropped to the ground, running her hands down my sides and ending by my hips. She looked me in the eyes with her classic smirk once again and licked the last of the cum off my dick. The sensation was enough for all the leftover cum in me to shoot out. Even Kelsey was surprised by the extra load, giggling quietly as the last of it dripped onto her tongue. I gave one last sigh of pleasure.

"One day I'll give you the perfect blowjob," Kelsey promised.

"Please let that be soon," I pleaded.

"You'll just have to wait. I love watching you be so desperate," Kelsie replied, laughing.

Kelsey wiped my cum off of her with the towel. The time came to address what we do from here. Carly and Kate were still waiting outside with the bottom half of my clothes.

"I'm sure they'll give you your clothes back if you just play their game," Kelsey reasoned.

"But I don't want to play their game," I argued.

"Look, they just want to hear about the jerk off folder. It's a part of our relationship so you gotta own up to it. Just let them tease you enough and I'm sure they'll give you your clothes back."

I thought about Kelsey's words for a moment. She was right. I knew I had to do it. Any embarrassment was worth it for her, anyway.

"Okay," I said. "Let's get this over with."

TO BE CONTINUED

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6 Comments
maddictmaddictalmost 3 years ago

Dude, your the only guy at the pool party, did you scream like a girl when you ran into the house.

Man up. As in, you want to see this well I need to see those.....

AnonymousAnonymousover 6 years ago
Good story, but...

you misused the word exacerbate. "I couldn't agree more, but I was too exasperated to say anything." I think you meant exhausted or something. Exacerbated means annoyed or angry. It doesn't make any sense for him to be angry after comming.

EdwinSixplusEdwinSixplusalmost 7 years ago
Looking forward to Chapter 3

..where I hope he jacks off for all three of them. Any story involving masturbating in front of women put me in an absolute trance.

LonesomesoulLonesomesoulalmost 7 years ago
Good start-

Hope chap 3 comes soon!

jimmcdonald609jimmcdonald609almost 7 years ago
Well done

Great follow up story.

I hope you will continue

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