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Stories Of My Life: Chapter One

"My first time enjoying cock..."

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Buzz... buzz...

I glanced over at my phone on the bedside table. It was him again. It was late enough, he must be finally drunk and away from his girlfriend. 

This had kind of become a routine for us.

Mark was a guy I worked with over the summer at the local country club. It was the second summer we were working together, though we hadn't spoken much until the end of last season, and even that didn't include too much. One time he basically thought I was a girl from behind, then for the final three weeks of the season, he'd made discreet comments to me along those lines. He was the first person to call me pretty, even though he used to only do it in a 'joking' sort of way.

I was always too shy to do anything but blush or laugh along with him. Plus, I was always just so excited he was talking to me. He was older than me, starting his third year of college, he smoked cigarettes and weed, partied, and drove an awesome suped-up Jeep Wrangler. He was the coolest person I knew. He also had a girlfriend, who was super hot, and a bitch. They had been dating for three years, and I had seen her lots of times, but never spoken to her.

I definitely did not have a girlfriend and I had never done anything sexual, even a kiss, with anyone. I was in high school and had never touched alcohol, weed or cigarettes before. And I knew Mark was right: I did look like a girl from behind. I kept my hair long, it was past my shoulders at that time, a light brown that could occasionally curl up a bit. Being 5'4 didn’t help either. The women of the world were not all over me, but I had started to notice glances from men. And having explored many internet chat rooms, well... I wasn’t as naive as I seemed.

Buzz... buzz...

I reached for my phone and read his message. This part was always so exciting.

“Aaww, man. I can’t believe Jackie!” He texted, referring to his girlfriend.

“Oh, now! What happened?” I asked him.

“She bailed on me again!!!” And went on to explain how she had left him hard again.

He normally complained about this to me, normally after he's been drinking, that is. He had fingered her to an orgasm in his Jeep, but she had stopped mid blowjob because she had to get home. He had pleaded with her, his cock out, hard and wavering. 

“She hadn't realized it was so late! She, of course, promised to make it up to me again,” he texted.

Which she always did, and it always meant they'd have missionary sex sometime soon.

He “loved her pussy,” he went on, but the “blue balls are killing me.”

“I can’t believe she left you like that again. That is incredible,” I texted back.

“I was close too. Five more minutes and I would've been cumming. She did save me having to clean up a mess in my Jeep at least.”

“How did she save you that?” I asked.

“I would’ve cummed all over my steering wheel and seats. She hates cum.”

Just reading him mention himself cumming had me heating up a bit.

“Oh wow... sorry,” I texted again. “Wish I could help”.

I didn’t realize what I had sent until after. Wish I could help? Oh god, what did I mean? What did he think I meant?

He replied right away, “Oh, really?”

I blushed, alone in my room, reading the text on the phone screen, blushing with a hard on. What should I say? 

“Hmm... Yes...” seemed the right thing to say.

I took a deep breath. What did I even mean? What did he think I meant? …Ah, he’s going to think I’m so weird!

“Well, you’re gonna have to prove it,” he wrote.

I could feel my heart pounding in my chest. This was so exciting. I wasn’t sure what he wanted, but I knew I would be willing.

“Ah well... and how?”

“You know you really are very pretty. How about I give you a ride home from work tomorrow?”

I blushed to myself, and excitedly told him I'd love that. He told me there was one thing: if I still wished I could help, then tomorrow after work, before I got to his Jeep, I was to change into a plain white shirt. Then he would know I was still willing. I agreed.

“Sounds good, cutie. I’ll see you tomorrow at work. Sweet dreams,” he texted eventually.

“Yes,” I replied. “Good night.” 

My cock was throbbing; it was the first time he called me 'cutie.' I tried to fall asleep, and finally did after a wonderful and very quick jerk off session.

I was so excited that I slept very little. In the morning I packed a backpack with my lunch and a plain white shirt to change into after work. Work was normal but went by painfully slowly. Mark didn't say a word to me all day, and every time I saw him looking at me, I’d blush and quickly look away. Then finally it was after work, and I was standing outside his jeep in a white shirt and my black work pants.

"Hey, hop on it," he said opening the door from the inside.

I stepped up and climbed into his Jeep.

"Thanks," I quietly said.

"Cute shirt." He smiled at me and looked me up and down quickly, leaving me beet red.

"Thank you," I replied as he pulled out of the parking lot. He turned the music on and lit a cigarette without saying anything. I just sat there incredibly nervous and silent.

After about five minutes of driving, he broke the silence. "I know a great spot, it’s right up here."

"Oh, okay..." I stammered, still looking down. He lit another cigarette.

He turned into a dirt road, and after a couple minutes, we came upon a little dock area for dropping boats in the water. He parked the jeep beside a small shack.

"Don't worry,” he told me. “No one comes down around here this time of day."

"Um cool... yes, it’s a good spot," I said, not entirely sure what it was a good spot for.

He reached into the glovebox and pulled out a joint.

"So, what did you mean by wish you could help?" he asked leaning back and looking at me while lighting the joint.

"Oh, ehm... I don’t know. I mean, I’ll do whatever I can to help."

"I had a feeling you'd say that." He smiled at me. “You know my girlfriend hates giving head..." he said, sliding a hand down to his crotch.

My eyes immediately followed his hand and I didn’t respond.

"So…” he went on, “that’s what I really need help with; I can’t handle all the blue balls..." He looked at me, but I couldn’t look up from his crotch where he was rubbing his hand slowly over an increasing bulge.

I didn’t move.

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I was sitting in the Jeep of the coolest guy I knew, and he was openly rubbing his hard on through his pants. I was mesmerized. Then I felt him take my hand and move it to his bulge. Before I knew it, I was rubbing his hard on through his pants. All of a sudden it was my hand slowly rubbing back and forth over the large bulge in the front of his pants. It was like having an out of body experience, until he spoke and brought me back.

"Mmmm, good, that’s it..." he moaned. Whilst smoking the joint with one hand, he undid his pants with the other. "Keep going, take it out."

The actions felt automatic, like I wasn’t even the one doing it. I glanced up at his face, to see him smirking; I blushed and looked back down to his crotch as I reached into his pants; I slid my hand in, encircling his already hard cock with my fingers, and pulled it out of the hole in the front of his boxers. 

Once I had it pulled out I just stared for a moment while gripping his shaft. It was so much bigger than mine. It wasn’t huge, just slightly above average, but still dwarfing my small cock. I just kept staring at it, in awe, as I slowly began stroking it up and down.

"Mmm… yes… do you like my cock?" He asked in a cocky manner that I found incredibly sexy.

I was too into the moment for words, so I just nodded my head slowly while sliding my hand up and down his cock. I shifted in my seat to get a better view. And right after I had settled into my new spot, I felt his hand on the back of my neck, pulling my head down to his crotch. I had watched enough porn and chatted enough online to know what this meant. I was very excited and nervous while I allowed him to guide my head to his cock.

He stopped just inches from his cock, my mouth already open with anticipation. He moved his hand up to behind his head.

"Suck my cock," he urged.

So I did. I looked up at him, into his eyes as I slowly took his cock head into my mouth. He moaned softly and leaned back into his seat. I started slow, having nothing to go on but porn, but having a real cock in the mouth for the first time was nothing I could prepare for.

I swirled my tongue around his head slowly while I kept just the tip in my mouth. Somehow his cock seemed even bigger than before.

"Fuck yes, that’s it… just watch your teeth." Rule one of cock-sucking, watch your teeth!

While I licked the tip of his cock, sucking gently on the head, I felt his hand slide up my back into my long hair. I felt him grip it, not too hard, but enough to make me moan around his cock.

I moved my tongue and now just focused on sucking on his cock. His hand started guiding me by the hair, up and down, going a little deeper each time. I heard him moan again, which caused me to moan in turn; then he pushed my head further down.

I gagged when I felt his cock hit the back of my throat, and I pulled up. My eyes were a bit watery and I took a couple of deep breaths.

He rubbed the top of my head, saying "Don’t worry, you’ll get better."

He then gripped my hair and pushed me down again, though not enough to make me gag this time. His cock was covered in my drool, as I tried to practice relaxing my throat. I bobbed up and down on his shaft, sucking as I went up and down.

"Oh fuck, that’s it… ffuuuck yes," he moaned as his cock was pulsing in my mouth; I was speeding up on his cock, his hand pushing me up and down faster.

'Fuck yes … oohh, fuck … next time we'll have more time..." he mumbled as I bobbed faster up and down on his cock, with no fancy cock tricks, just keeping my lips tight around his shaft and sucking as I went up and down in shallow strokes.

"Fuuucckk, yyessss, ffuuuuck!!" He groaned as I felt him grip my hair tight. This time he didn’t push my head down, but held it steady, as he started cumming in my mouth. He held my head so just the tip of his cock was in the mouth, covering my tongue while he filled my mouth.

I was definitely startled. I was expecting some kind of warning and, having not picked up the signs yet, I had no idea he was about to start cumming.

He must have spurted ten times into my mouth; I had to start swallowing midway through and some still leaked out. It was the most amazing feeling I had ever experienced. Making someone cum, bringing them to orgasm, not being warned and swallowing his cum made me feel so slutty ... so submissive. I loved it.

He finally let go of my hair and slumped back in his seat, saying "Fuck, that was amazing, but don’t forget to get any that might have leaked out, cannot have my girl see cum stains on my seats."

I quickly licked down his shaft, licking up the cum that had pooled at the base; it wasn’t much, considering the huge load he had just shot. I felt some pride in knowing I could handle that.

Once I finished swallowing, I sat up, while he lit a cigarette. Nothing much was said on the way home, except for him asking me for directions to my house. There he pulled up out front, stopped the car and looked at me.

"Think you'll need a ride home tomorrow too?" He grinned. 

I blushed. "Yes Please... I mean, if you want to..."

"You can keep a secret, can't you?" He asked looking at me, my eyes a little red.

"Oh yes, I can, absolutely...I promise," I said as I looked up at him, then back down to the ground.

"Good," he smirked. "Wear a pink shirt tomorrow and meet me at my jeep after work."

"Okay! See you tomorrow," I said maybe too excitedly, to which he grinned, as I blushed and got out. "Thanks for the ride."

"No problem, it’s the first of many, babe," he said as he smiled and winked at me before driving off.

There I stood, nervous, scared, excited. I couldn’t believe what I had just done... and what I was going to do tomorrow.... or... I know I’d do whenever he wanted. All I really knew was that I loved it, all of it. And I couldn’t wait for more cum. 

Summer had just started, but my whole world had already changed.

 

Published 
Written by kinkyartist90
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