Mason's Gamble by Chris Jamesv    Mason's Gamble
by Chris James


  Teenagers
  Sexual Situations
  Rated Mature 18+

Mason's Gamble by Chris James

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Author Introduction
    I never spent a minute of my teenage years working in a fast food restaurant, but many of my friends did, and in some crazy way this story is a tribute to them. I keep running across these stories from the past, penned when I was barely older than my characters. But I contribute so little to the high school section (of the Nifty Archive) I had to give you this one, sorry for the brevity.


I was sixteen when I had my first sexual encounter, it was the same year I started working at Taco Land. It was a necessity, the job I mean. There were no wealthy parents and no legacy from a dead relative, there was just me trying to earn enough money to buy a car. My mom said she would help out a little, but she didn't have much, I needed that job.

It's hard when all your friends have money. Work took up all my free time, but I like myself better for the hardship. My father used to watch me stacking wooden blocks when I was two. I would get them up real high and he would knock them down. Predictably I would cry and the old man would pick me up and comfort me.

Sounds crazy, right? He said it would build character, as in adversity builds character. Unfortunately he never got the chance to find out if it worked. He was a contractor and one of his buildings fell down and crushed him. Maybe he stacked it too high and God knocked it over. I'm told my father had lots of character, but I was only five at the time of his death and so I didn't know him very well.

Oh, yeah. I was sixteen and rolling burritos in the kitchen when I first met Sam, the new assistant manager. I'd been there three weeks and was just getting to know my way around. Sam had been hired by Mr. Donnegan, the owner and somehow a distant cousin of my mom's. Not that there was favoritism in hiring me, I worked my tail off.

Mason's Gamble by Chris James

So Sam moves in to my afternoon shift. He's a college boy, nineteen or twenty I think, at UMass. Donnegan likes the way he looks and how smart he appears, or so he told me. "Going to grad school too, maybe he'll work for me a little longer than the others do."

And that was Donnegan's hope, to find a capable assistant so that he could fly out and visit his sister in Sacramento. The last two hopefuls he'd hired were more hopeless than capable. The first forgot to lock up one night and they found the place occupied by homeless people the following morning. They made a mess trying to figure out how the taco press worked and nearly burned down the store. The second was pinching pennies, not his but Mr. Donnegan's. The police had a nice warm cell waiting for him on his last day of work at Taco Land. Then I arrived.

Sam confided in me that first day, he had never worked in a restaurant before and had lied to Donnegan. So what, I thought? It was my first time too. He managed to learn a few things from me the first day and we made a deal to cooperate from then on. So here I was several weeks later rolling a burrito special, lots of sauce and sour cream, when a hand reached between my legs and grabbed my ball sac. The contents of the burrito squirted out as I gripped the tortilla and gasped at the same time. The mess flew out and landed on the floor several feet away.

"Gotcha ... surprised?" Sam said in my ear, and I felt the pressure on my balls disappear as he let go.

I turned on him. "What the fuck ... are you out of it? Look at the mess," I yelped.

Sam just smiled and dangled a set of car keys in front of my nose. I still had the tortilla in my hand, sour cream dribbling down my fingers like ... well, you know, and I didn't understand what he was doing.

"What are you doing?' I asked

"Holding your future happiness in my hand, Mason-boy," he replied. "I got you a car."

"You got me ... "

"And not just any car ... sixty-seven Mustang, baby blue and only eighty-two thousand miles on it. Works like a charm and it's all yours for the low, low price of ... ?"

Mason's Gamble - The 67 Mustang

"What ... what?" I almost screamed. I was jumping up and down like a three year old that has to pee real badly. "What do you want for it?"

"Your undying love and friendship, your first born child and your virginity, your baseball card collection and a big fat kiss. Can you do all that?"

Did I mention that Sam was crazy about me, as in crazy in love with me? Oh, I'd known from day one that he was gay. "Not fruity gay, just gay, as in I like cute boys like you." His very words to me as we cleaned up that first night together.

I didn't freak out, and in fact I took it as a compliment. He is, I'm not, let's get that straight right from the start. But I knew it took courage to tell me, and although I've never had another guy tell me I'm cute, I've never heard girls say it either.

Ok, I look in the mirror and see green eyes, mousey brown hair that always needs cutting and a few pimples on my chin which I blame on the taco grease. I don't know what Sam sees that makes him say I'm cute, maybe he needs glasses.

As for Sam, he's a six foot, lanky blonde-headed, blue-eyed gay college student. You'd think he wouldn't have any trouble attracting other guys like himself. I'd say he was handsome in a manly way, the rugged outdoor type, and maybe even good male-model material. I don't know, don't press me, I don't look at guys.

I dropped the remains of the messy tortilla and followed Sam out to the parking lot. And there it sat...my new car. Except that Sam wanted me to do...what? The only thing I could remember was the part about a kiss. The car for a kiss, and something, something?

I jumped up and wrapped my arms around Sam's neck. My lips sought his cheek for the kiss and somehow ended up on his mouth. I kissed him right there in the parking lot and felt our tongues touch.

I wanted to pull away but couldn't. Sam had wrapped one arm around my waist and the other went behind my neck and held me in tight. Our tongues dueled and I lost count of the seconds in our kiss. But I did know one very disturbing thing, my cock got stiff.

Sam ended things before the scene made the morning papers. We walked around the car and I admired the white vinyl interior and the baby blue carpet. The car was cherry and so was I, but I didn't know for how much longer.

We had to go back inside, there had been two customers at the counter and Donnegan would have a fit if they complained. I sort of hobbled back to the kitchen door. My cock was stiff as a board down the right pants leg of my jeans, but fortunately the apron hid it from view. Did Sam know how I had reacted?

All day until closing we were both very busy and didn't have two minutes to talk. Donnegan had arrived at lunchtime, but left by seven. By nine I had the place cleaned and Sam turned out the lights. I wandered back to the small office where he sat counting the day's receipts.

"You wanted a kiss and I remember something about love and friendship. Was there anything else?" I asked.

I had finally remembered the whole line, every bit of it. The part about first born and virginity kept popping back up in my head. Sam wanted my virginity? I wasn't sure what that meant, but coming from a gay guy who knew? The whole kiss scenario kept playing back in my head until finally I decided that I had just been so overwhelmed by the events that my reaction was normal.

I was still stunned that someone I had just met would just up and give me a car. Yeah, his family came from serious money, mega-bucks. But his daddy had insisted Sam get a job while he was in school, Taco Land was hardly what the old man had in mind, probably why Sam did it.

Yes, I considered that it was more than just a friendly gesture. I knew he lusted after my body, but I wasn't sure this car was meant as a bribe just to get in my pants. Sam stood up from the desk, carefully locking the stacks of cash in the safe. "I don't think so, I got my kiss," he said. "Did you mind kissing me?"

"I ... I don't have a lot of experience in the field," I stammered.

Sam came close and put his hands on my shoulders. I looked up into his deep blue eyes and knew he was going to kiss me again. I knew I shouldn't, I wasn't gay. But I just leaned forward as our lips met and allowed the kiss to flow between us.

As before our tongues met and my cock got hard, only this time there was no apron to hide my passion. Sam pulled me close and I knew he felt the hardness in my pants pressing against his leg. This kiss seemed to last forever and I didn't mind one bit. It was Sam who pushed us apart.

"This isn't fair, Mason," he said. "You're so young and I feel like I'm taking advantage of you."

"But what about my virginity?" I asked

Sam's eyes grew wide. "Oh, so you remembered," he said.

"It isn't about the car, Sam. You're my friend and I love you for it. But the virginity thing troubles me. I don't know why but I'm not scared. How do gay guys lose their virginity?"

"We don't have to go there," Sam said, "I was just being silly."

"Oh, but it was part of the bargain and I always keep my commitments. You'll just have to show me," I said.

"No, Mason, it wouldn't be right."

And maybe that's why it had to happen. I felt like I was straight but the thought of sex with a guy didn't scare me, a guy like Sam anyway. Maybe I wasn't too straight? He sure kissed real nice. There was more to this excitement I felt, more I wanted to know about sex in general. The virginity issue had to go.

"Show me, Sam. I want to know." It was the right thing to say and Sam finally accepted it as the truth. He unbuckled my belt and my pants hit the floor.

Let me say something right now about first time sex. Since the tender age of eleven I had been flogging the worm, beating my meat, choking my chicken, pulling my pud ... whatever you want to call it. My years of experience at self-gratification did nothing to prepare me for the first time someone else gave me pleasure. That it was someone I trusted, someone I cared about, made all the difference in the world.

I suppose in my mind the fact that Sam was gay meant he knew everything about sex. But much of his sexual past was on the receiving end, and I'm not surprised. With those looks he must be an easy man to adore. Because of my inexperience he was kind that night which I'm sure took away some of the pleasure he might have wished for himself.

His touch was gentle and as he undressed me. I shivered in anticipation as his fingers explored my body. His kisses lingered in places I had no reason to expect would thrill me. I lay back on the desk as his tongue traced a line from my nipples to my groin. And when he finally took me in his mouth I almost fainted from the sheer pleasure of feeling my cock assaulted by his lips and tongue.

He sucked gently as his tongue explored the flair of my cock head and rasped against the underside of my shaft. Masturbation had never felt like this and yet it had always brought me to orgasm. These unfamiliar feelings quickly overwhelmed me and I felt the pulses begin. I didn't want it to be over, it shouldn't be happening so soon, but it did.

I had little time for more than a moan of delight before I came in his mouth. I shuddered several times and was beyond the thrill. My mind screamed that it was unfair that such a wonderful thing should be lost so quickly. This was followed with guilt, not for what we had done but that Sam was probably disappointed in me.

"I'm sorry ... " I began to say, but he put a hand to my mouth to silence me.

"Sorry has nothing to do with it," he said. "Inexperience and youth brings you to the edge so quickly. Allow me to teach you otherwise before you apologize every time we do this. At your age there is always more than one shot in the gun. Let's just say that was practice, ok?"

And I knew he was right. Most times I brought myself off several times in a row. I knew that Sam was capable of getting what he wanted from me and I would be the better for it.

"That was wonderful," I said.

"Batting practice is over and you did well. Now we can play the game," Sam said. "I'm going to pitch and you'll catch." I grinned at his analogy, and then realized he was talking about fucking me. Uh-oh.

Sam handed me my pants and we closed down the store. He lived off campus in a one bedroom apartment over a grocery store. Tastefully decorated, I thought as we zipped through the living area to the bedroom. It wasn't at all like my room. This place was neat whereas I lived like a messy kid.

We took off our clothes and lay them on the bedside chair. It was my first look at him naked and I was shivering in anticipation...or was I scared? He had blonde hair on his chest where I had nothing but fine dark fuzz beginning to sprout around my nipples. Even the bush above his cock was the same blonde hair I found so attractive.

"Nervous?" he asked.

"Yes, um ... does it hurt? I mean, your cock looks pretty big to me."

"It may cause some pain but that goes away if you learn to relax. This is about pleasure, Mason."

"Do you like it done to you?"

"Yes, very much. But I started when I was a lot younger then you. I was twelve my first time."

"Twelve? That's too young for sex."

"I didn't think so, I was in love," Sam said, his face took on a far away look of pleasure. "His name was Kevin. He was thirteen when his family moved in next door. I remember watching him get out of the car and standing with his family in the front yard. He was awesome, so handsome and so beautiful at the same time."

"Did he love you?" I asked.

"No, he thought I was a fag, at least in the beginning. I was the one who brought love into our relationship. Do you really want to hear about this?" Sam asked.

"Yes, I think love stories are great."

"Ok. Kevin's bedroom and mine were facing each other across the driveway. He always kept the shade down at night so all I could see was his shadow. But I was fascinated even by that.

"He used to mow the lawn wearing only a pair of shorts, tight little shorts that drove me up the wall. And one day I was in my room when he finished mowing and went inside. My drapes were closed but somehow I knew he was over there and went to look. The shade was up and I watched him towel off the sweat of his labor and then strip down to nothing. Maybe he didn't realize the shade was up or maybe he didn't care. But it was the first time I saw him naked and I was thrilled to death."

"Did he know you were watching?"

"Not then, but I told him the next day."

"Oh, shit ... how did that go?"

"I was scared to tell him but felt like I had to take the chance. Either he'd laugh it off or hit me. So I invited him over and took him up to my room where I told him."

"And?"

"I told him he had the nicest body I'd ever seen. I said he was strong, handsome and well hung ... and I told him I loved him."

"Uh oh."

"It was a gamble and I won. Kevin was so amazed that he actually stripped down right there in front of me. He wanted me to tell him again about what I liked. I flattered him and he masturbated in front of me. I didn't need to touch myself. I came in my shorts just watching him. Things changed between us after that. He was quite the exhibitionist, and I was his favorite audience.

"So I talked him into having sex with me. I started blowing him and he started fucking me, we both thought it was a good deal. And it was until my father caught us and it all came crashing down. End of story."

"Your father knows you're gay?" I asked.

"Back then, no. He thought I was the victim and Kevin got punished. His family was so embarrassed they moved to New York. I was thirteen by then and had lost my first love."

"How sad. Have you ever spoken to him?"

"What for? Kevin was straight; I was just a fuck, a practice dummy."

"Sorry," I said. "But it must have hurt you when you first did it?"

"Yes, I'm sure it did. But I don't remember the pain. I just remember how good it felt to get fucked."

We were naked on his bed our legs entwined. ""Do you still want to try it?" Sam asked.

"Yeah, I do. I feel weird saying that because I've always thought of myself as straight. But I want to know how it feels, and I wouldn't do it with anyone else but you, Sam"

"I think you're brave and daring, Mason. When it's over you'll know what I like about it. Then can you decide if it's what you want to do or walk away from it."

"Yeah, it's a gamble. But with you I like the odds."

Sam rolled me over on my stomach. The kisses began again as strong fingers sought to knead the muscles of my lower back. It felt so good, I could feel myself beginning to relax. Sam kissed and licked the tight skin of my ass, his fingers sliding lightly up and down the crack. I closed my eyes and allowed myself to be caressed.

His tongue licked down the groove and began a steady lapping at my ass hole. I shivered in response. It felt so different and wonderful. Then it occurred to me that his body was right there next to mine and when I opened my eyes I saw his cock only inches away.

I had never thought about sucking a cock, but Sam had done it so well. I reached out with my tongue and began to lick the shaft of his cock. In response Sam shoved his tongue right in my ass hole.

Ahh, it was like fireworks going off in my head. I never knew that such wonderful feelings could originate in my butt hole. I was so wound up that for no apparent reason I decided to swallow Sam's cock. The first five inches were easy but things got hairy at six and downright distressing when seven inches clogged the back of my throat and I gagged.

Sam realized my error and pulled himself away from my mouth. I gasped for air and choked back whatever I had consumed for lunch. By then Sam had worked two fingers into my butt and was trying to pry open the door. I grabbed his cock and tried to lick an orgasm from it until my throat recovered.

But I never had the chance because Sam judged my rear was ready for the invasion. He turned himself around and raised my legs. I could feel him prodding me back there, sliding around in his own spit and missing the target. Finally he centered himself and leaned into me.

Ahh, I tried to relax. Come on kiddo, after all this was your idea. I thought about taking a major dump and how the muscles had to relax for that to occur. His cock began the inward slide and then suddenly he was through door and racing up the hallway.

My brain was assaulted with conflicting feelings from my rear. Pain was a small part of it, but the feeling that my body had been invaded by a large foreign object was foremost. I knew his cock was big but now it felt like a bus was parked in my butt. Impaled, yeah, that was the word my brain threw at me. Had I really absorbed all eight inches of his manhood?

Sam jiggled around a bit to loosen me up and then he began to slowly withdraw. Oh, oh, don't leave. I clawed at his neck trying to pull him back. But he only withdrew eight inches before parking the bus again. After a dozen moves like that I was getting used to the pressure.

He stared down into my face and grinned. "Are you ok?" he asked.

"I will be when it's over," I grunted.

Sam began to move faster. A quick withdrawal and slow insertion, over and over until the repetition numbed my brain and jangled every nerve in my ass. His face scrunched up, his breath became ragged and I understood that relief was in sight.

I felt his cock swell as he plunged in deep and filled me with his cum. He withdrew and I felt my ass still quivering from the assault. It was over, my virginity surrendered, the car was mine. I should have been happy, elated, overwhelmed, but I already missed his cock in my ass.

My determination had paid off and I was the big winner. A good job, a cherry blue Mustang and a rich young college boy to fuck me whenever I wanted. If you get the chance I recommend you take your own gamble and see what happens.

"Mason's Gamble" Copyright © 14 Jul 2009 by Chris James. All rights reserved.
    This work may not be duplicated in any form (physical, electronic, audio, or otherwise) without the author's written permission. All applicable copyright laws apply. All individuals depicted are fictional with any resemblance to real persons being purely coincidental.


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