JACK - MY FIRST TIME [11/11/1999]

I grew up in a large family and therefore we never had much. At a very early age you learned how to be self-sufficient. Those people in the small rural village who wanted to have anything would begin working at a very early age. I was an energetic 13 year old boy who worked all summer long since I was 8 or 9 doing odd jobs for 4 or 5 dollars a week. It wasn't much but back in those days it was like a million dollars.

I had longed for the time when I would finally be able to go with the big kids and do a real job. Something like picking tobacco or potatoes or something. So when the opportunity came up for me to work for my uncle, I grabbed at the chance. I started working every night after school. Some nights I would be there for 2 or 3 hours and always all day on Saturday. For this I was given the princely sum of 5 dollars a week.

It was about a mile from my house to the job and I walked back and forth most of the time. That summer I spent a lot of time going back and forth to home and work. Since I was out of school, I was able to spend more time there and make more money. It was during this summer that I first saw Jack. I had been having fantasies about men before but this guy stuck in my head.

Jack was a poor old man who lived in a rundown shack about halfway to my house on a dead end laneway. It was way off the beaten track and since he was a hermit type, nobody knew much about him. I began to see him everday going from home to the store. I began to look forward to seeing him and would purposely wait for him sometimes.

The summer went on and I maintained my observations of Jack. I found out his name and where he lived and even knew he had a dog. But he didn't even know I was alive.

One day, by accident, I met up with Jack and as luck would have it I was with friends and couldn't take advantage of the situation. I said hello and he answered back. After we were out of earshot my friends commented about the strange old man and began to make fun of him. I became very defensive, overly perhaps and we had quite a little argument about the whole thing. Later that night I looked back and realized just how much I had become attracted to Jack.

The summer passed and so did the autumn and I maintained my distance from Jack. I was too afraid of him to actually approach him. I turned 14 in November and was still a virgin so even though my thoughts of Jack were sensual I was never able to act on them, even by my own hand. Yes, I would play with myself, but I was yet to achieve orgasm.

I tell all of the above for one simple reason. To set the record straight that at 14 I was able to formulate fantasies of a sexual nature and also I was totally in lustful love of a man who was perhaps 60 years old.

It was about March and the spring thaw had just begun. I was on my way home from work at about 7pm on a Friday night. It was cold out and the warmth of the day had given way to a colder evening. The snow and ice that had melted earlier in the day was now frozen again and the roadway was slippery. I had fashioned a ice pick by driving a nail into the end of a broom handle. I was playing with the icepick on my way home and when I arrived at the juncture of the laneway to Jacks house and the road to my house, I paused under the street light.

There was a lot of ice on the corner and I began chipping away at it with my ice pick. I was probably there for 15 or 20 minutes and didn't notice that Jack was on his way home and would have to pass by. He took me by surprise and said hello as he drew near. I was very anxious to talk to him and was able to strike up a conversation about how slippery it was. We spoke for a few minutes and I realized that I had the opportunity to escort him home. I asked him if he would like me to walk him home, since I had the ice pick and could help him from slipping and falling on the ice. To my elation he agreed and away we went.

I was thrilled to have him wrap his arm around me to gain support. I, in turn, put my arm around his waist while using the ice pick with the other hand. The ice pick did little to stabilize us but it did give me an excuse to hold onto Jack as we walked.

We turned into Jack's driveway and just before he went inside he said to me that he needed to take a leak. My heart was in my throat as I watched him prepare to piss into the snow. To my great disappointment he turned away as he fished out his cock and began to piss. All I could think of was how much I wanted to see his cock. I was desperately trying to maneuver to a position where I could get a look but before I could he finished. My heart sank with the realization that I wouldn't be seeing his cock.

Jack asked me if I wanted to come in for a while and I said yes. I would have done anything to keep the dream alive.

Jack's house was really just a cabin. It had two rooms, the one in which we first entered had a double bed against the far wall, a table with 2 chairs and a stove with a 3rd chair beside it. It was the first time that I realized that Jack didn't live alone. His roommate, Gordon was sitting on the chair by the stove. He was quite drunk and didn't even seem to notice when we entered.

Jack sat on the side of the bed and motioned for me to join him, which I did. He offered me a drink, which I accepted. I almost gagged on the half glass of cheap wine that he presented to me. He offered me a piece of pie which was equally as gastly but I ate it anyway. You see, I came from a poor family and I knew that what he was offering was probably all the food he had in the house. He was really poor and his generousity could not be turned down.

All the while he entertained he spoke of his life and how he was when he was young. I listened intently as he spoke of his growing up. He told me of his days when he was a budding young boxer. The stories rolled off his tongue in quick succession. Eventually he began to talk about some of his sexual conquests. After a couple of short stories he began to tell me about the time he had two girls at once. As he told the story he would pause and, placing his clasped hands between his knees, he would squeeze his legs together and grimace as he cooed. This was his way of expressing the sensuality and eroticism of the events. I was enrapt with his stories and in my mind I was putting myself in his stories.

I was at Jack's place for almost an hour now. Jack had fed me, given me drink and filled my head with his wonderful stories. He finished one last sexual story, yawned and informed me that he was going to lie down. He pulled his fully clothed body onto the bed and laying on his back he moved to the far side of the bed leaving me still sitting on the edge.

He lay there quietly for a minute or two and then asked if I would like to lay down also. I wasted no time in taking my place beside him. As I lay there I could feel my heart pound as I tried desperately to move closer to him without him detecting the fact that I was doing it on purpose. I was there for a few minutes which seemed like hours before Jack stated that "you know we're not alone". "I know", I said. "Maybe Gordon would like to lay down as well" I continued. With that I asked Gordon to come lay down. My real reason for asking was to give myself an excuse to move closer to Jack. I turned my back to Jack and moved toward him until I was tight against his side. At the same time I patted the now empty space on the bed for Gordon to lay down. Gordon stayed on the chair with his head down, semi passed out. There he stayed and I was fine with that.

Seconds after I made contact with Jack he turned onto his side so that he could cuddle into me. I thought I would die when he put his arm around me and pulled me to him. He then put one leg over mine and pulled me tighter to him with his leg. My heart was going wild with anticipation and fear. I lay there, both thrilled at what was happening, and terrified at what might happen next. Or maybe what wouldn't happen. I was still a virgin and he was so sexy. How, I thought, could I possibly live up to his expectations. Jack held me tightly for a moment then whispered in my ear the sexiest, most erotic thing that anyone has ever said to me, "do you want to suck it". He said it so frankly and with such finality that it startled me. Not knowing what to say I replied "what". He came back with an even more demanding "you heard me". I was silent for a moment while I contemplated an answer. Afterall, I didn't even know what suck it meant. I knew I wanted to "suck it" but wasn't sure how. Out of my mouth came an equally emphatic "YES". It seemed to come out as almost a shout.

Jack released his grip on me and fumbled around on the bed until he was able to get both of us under the blanket that we were laying on. Once under the covers he pushed me down under the covers. He kept pushing me until my face was in his crotch. It was too dark to see but Jack manipulated my head until he was able to get me into position. He undid his pants and pulled them down to his knees. His exposed cock was thrust at me and in a moment of disbelief I took it into my mouth. His cock was about 5 or 6 inches long and kind of soft and doughy. The head was quite large and a bit pointy. I'd never had a cock in my mouth before and all I could do was slosh it around in my mouth. I was too fat to do much of anything else. (I wish I knew then what I know now...I digress)

His cock tasted sweet and I could taste the precum (I didn't know what it was then). I continued to lick and slurp on his big cock for a while then I stopped. I pulled myself up to the pillow and came face to face with Jack. I really wanted to kiss him but before I could he said "do you want to stick it in me". This time I didn't need to think and said "okay"

With that, Jack turned his back to me and offered his asshole to me. I was rock hard and quickly had my pants around my ankles. My cock slid easily into Jack's ass and I began to fuck him with all my might. I reached around and took hold of his cock and began to play with it as I fucked him. Jack kept pushing his ass against me which allowed me to feel my pelvis strike his ass cheeks. The feeling was incredible.

As I played with his cock he did something which, to this day, I didn't understand. He squeezed my hand that was on his cock and pulled it away. I've never understood why he did that but I remember being very disappointed when he did. He moved my hand away and rested it on his chest. I kept fucking him and eventually moved my hand so that it was over his shoulder. This gave me the leverage I needed to drive my cock in to the hilt. Then something started happening to me that I never experienced before. I began to feel a burning in my groin. It was scary at first then all of a sudden the burning was replaced by a feeling of release. I was cumming for the first time. The feeling was warm, wonderful and completely erotic. It was like I exploded. When I finished I pulled my cock from his ass and pulled my pants on. Jack did the same thing and we both began to climb out from under the covers.

Gordon spoke for the first time. "What's going on over there" he asked in a groggy voice. I honestly can't remember who, if either of us, answered him. I turned to Jack to say goodbye and he told me to come by again sometime. Before I left he reached into his pocket and gave me 75 cents. "Here, take this and buy something". I was really in heaven. I couldn't wait to tell my cousin Art that I had sex and actually got money. Remember, I was barely 14.

The money was considered a gift from a wonderful man and I accepted it with all the innocence of youth. I ran all the way home, excited and on top of the world.

To this day, that experience remains as one of my most erotic memories. The moral being that a young boy seducing an old man happens. I have always considered that one of my most incredible conquests.

Oh, to be able to relive that experience again.

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