Odyssey of a Young Guy

MY PART-TIME JOB

I have a part-time job after school at a computer repair shop, testing and restoring computers. The job is interesting and I made ok money. Besides the repair business my boss Jeff is a network guru and branching out into consulting. He took the time to explain not only what and how to do something, but the why. Even though he was my dad's age we got along well.

One day after we closed he asked me about girls.

"I'm awfully shy around girls and get all flustered."

"No girlfriend? You are a nice guy and really quite good looking. I suppose your biggest handicap besides being shy is that you look so young. Girls that might be interested are young and not ready for sex. You must get really horny. Surely you jack off?"

"Uh, no, I've never done that. I play with my cock some and that feels good."

"Damn, Greg, for being eighteen you are really behind the curve."

His observation didn't make me feel any better. I am socially inept and totally tongue-tied around girls in my classes. Rather than make a fool of myself I cope by being invisible.

"You need someone to show you how to have some fun. If girls are scary maybe you could start by playing with guys. Stand up and pull down your pants, let me see your cock."

I was shocked.

"Come on, don't be shy. Now the shorts."

Embarrassed as hell, I stood before as he eyed my limp cock. He placed his hand on it and squeezed and it started to erect.

"Damn, that's a monster, Greg," he exclaimed as it became fully hard. "Biggest one I've ever personally seen. Girls should be all over you to get that inside them. What a waste that it doesn't get any use. But that's ok. You are just a late bloomer," he tried to mollify my obviously hurt feelings.

He put a glob of hand lotion on my cock and stroked. "Now you try it."

I wrapped my hand around my rock-hard cock.

"Feels good, doesn't it?"

"Yeah."

"See what you've been missing? Every guy I know does it whenever there isn't pussy or ass available. Another few minutes and you will squirt. Get ready so it doesn't go all over."

In spite of his warning, I was unprepared and erupted all over, my first orgasm.

"So now you know how to jack off. Now go home and practice."

That night I did it twice more. And later that week he did it to me which was even better.

"Have you been practicing?"

"Yeah, every day, mostly twice a day. "I have something else to show you," he said on Monday. "Get undressed and sit in the chair."

He took my quickly hardening cock in his hand. "I still can't get over what a big one you have."

Then he leaned towards me and licked the head of my cock.

"How's that feel? Want me to do more?"

I nodded my head.

He licked along my cock from the base to the head and back down and then took it in his mouth! The feeling was exquisite as my cock bumped the back of his throat. He moved my head back and forth, my cock going in and out and then down his throat. The feeling became more and more intense.

He pushed a finger into my ass and I exploded, surprising him with a huge load of cum. He gagged and pulled away, my next spurts hitting him in the face.

"Oh, I'm sorry. I didn't know that would happen so quickly."

"That's ok," as he wiped his face with a towel. "Next time give me some warning. So how was it?"

I was still in a daze. "Oh, Jeez!" I finally responded. "I never felt anything like that. Thank you."

I looked forward with anticipation to my next work day and felt a need to reciprocate. He guided my head so he could push his cock between my lips. I wanted to taste him, to bring him pleasure and make him cum. I explored it with my tongue and mouth, the feel and taste exciting. Becoming bolder I licked around the head and then plunged halfway to the base.

His cock touched the back of my throat and caused me to gag. Again, I tried and again gagged but I was determined to take him all. I held his cock at the back of my throat. It tickled but I held back my gag reflex. I pulled him to me and his cock suddenly entering my throat. My eyes watered and I had to quickly back off but I had done it!

I felt his body tense as his cock exploded in my mouth, load after load of warm semen. I swallowed as fast as I could to keep up. Each work day thereafter we did each other.

"Do you like me playing with your ass while I suck you?" he asked after our latest get-together.

"Feels kind of weird but ok."

"Next time I'd like to fuck you in the ass. It won't hurt, I promise, and will feel really good. Don't worry, exploring your sexuality doesn't make you gay."

"Even If you fuck me?"

I wasn't keen to do it but he persisted and I finally agreed to give it a try, just once. There was a bed in the back room for times when he worked late.

"What do you want me to do?"

"Lay down on your stomach. I'm going to start with just my finger like I've been doing."

I felt cold lubrication on my anus and then his finger inside. "Try to relax, we will just play around for a while."

He continued to finger-fuck me, adding more lubrication. "Now I'm going to use two fingers. It will seem tighter but should be OK." My ass felt stretched but it didn't hurt.

"You are doing great, Greg. My cock is just a little bit bigger than my two fingers."

He withdrew and I felt pressure of his cock against my anus. I tensed up again as I felt his cock slightly penetrate me. He backed off and applied more lubricant. The head of his cock pressed harder against my anus.

"Try to relax," he encouraged as he continued to press. "Push back like you're trying to take a crap." I felt his cock slightly penetrate. He withdrew and then pushed again, this time going in a bit further.

"Stop. It hurts."

He backed away and then pressed again at my anus. It hurt but not as bad. He maintained pressure and gradually my ass opened slightly to the pressure. After a short pause he withdrew, added more lubrication, and a moment later I felt an intense pain.

"Oh, damn, that hurts! Take it out!"

"It's done. I'm in your ass. The pain will go away in a minute."

The pain lessened but resumed when he pushed his cock further into me. I held my breath as he went deeper, deeper, a feeling unlike anything I had ever experienced. Slowly, inch by inch he stretched me, filling me with his big cock.

"All in! That wasn't so bad, was it?" The pain had lessened, replaced by a feeling of extreme fullness.

"Now I'm going to fuck this tight hole of yours and stretch you wide open."

He reached under and took my hard cock in his hand.

He withdrew until just his cock head was inside, then reentered. Each time a little faster, he fucked my formerly virgin ass. I felt a tingle each time he entered. A few minutes later he grabbed my hips, pushed deep, and filled me with warm cum. I squirted cum all over his hand.

I lay there in a stupor, his cock still inside me.

"How does your ass feel?"

"It hurts a little."

"You'll be OK. By tomorrow the soreness will be totally gone and next time will be easy. I would let you fuck me but you would tear me up with that cock of yours."

That night I replayed in my mind every moment. My ass was already back to normal and it had felt rather neat.

"You like what we are doing, don't you?" he asked a couple of weeks later. "I have some friends that would like to fuck you. Guys my age don't have many opportunities to make it with guys like you. You are young and very handsome in a pretty sort of way. Smooth body, tight ass. We get together on Saturday afternoons after the shop closes. You interested in joining us?"

"No, I don't think so. Only you and me know about this. People talk and I don't want others to think I'm gay. At least I don't think I am. And I don't like the idea of some old guys I've never met sticking their cocks in me."

"It won't be a problem. They are married and have incentive to be very discrete. We have been getting together for years."

"You and them? You fuck them and they fuck you?"

"Yeah, of course."

"And what would they expect me to do?"

"Fuck you in the ass, maybe a blowjob."

"And what about me?"

"I really doubt any could take you up the ass but someone will give you a blowjob. And I will make sure they pay you a decent bonus for doing it. So, what do you think?"

The promise of some extra money was very enticing. "How much would they give me?"

"At least $50 each time, if that's ok? I'll invite Frank for next Saturday. He's a really horny guy and has a thing for young ass. Then if you say ok I can invite other guys on subsequent Saturdays."