The Flagpole Sitter

This is based on a real story.

Maybe.

The names are real. Or not.

You decide.

When I was a Young. We had a test given to us in our school.I guess it was an aptitude test. Or IQ test. Whichever they give to young men and women that age. Which to me is ludicrous. Considering that, it’s a proven fact that the human mind doesn’t fully develop until well beyond the age of 18. But I digress.I remember when we had finished the test. And the teacher had handed them back to us the next day. It was in a strange way. We didn’t actually get the test back with the grading. But were given a piece of paper that was private for each student. We were instructed not to look at the other students results.

When we opened the piece of paper there was a number written on the inside. The teacher then began to tell us how our results worked.She said, If if you have a score between 90 and 100. You will no doubt become a scientist or an astronaut. If your scores between 80 and 90 you will probably become a Doctor or a teacher. If your scores between 70 and 80. You will probably be a farmer, a timber cutter, a store clerk or work in a factory. If your scores between 60 and 70 or lower. You will probably become someone who rolls up toilet paper on toilet paper rolls. Or flagpole sitter.

Well I had started off well in school. But as time went by, my grades weren’t all that great. And her response angered me. What gives her the right to say I was going to roll of toilet paper on toilet paper rolls. And what the hell is a flagpole sitter?We were instructed to close up our papers and bring them back up one by one to the teacher. And as time went by most of us forgot about the test.

But things have a way of haunting you. Not long after when was I older. We had a carnival come through town. And they had all the common things. A mysterious madam and her crystal ball. A tent for adults only. The bearded lady. Some kind of ferocious looking monkey with a big red butt. That they called the lion killer. And there was a big cage with a boa constrictor in it. Just off the side of it as I passed by, I noticed there was a poster on one of their wagons of some kind of a Eastern Mystic. And what was he doing? Well of course, He was sitting on top of a flagpole.

There he was. Perched up on a little 12 inch by 12 inch by 1 inch thick board. Sitting on top of that board. With his legs crossed meditating and balancing himself on top of a flagpole.I had to see him. But that would be at our school yard. On our flagpole. At a cost of another 50 cents. That I just did not have.What’s this got to do with erotica you ask? Well let’s go on. And let the story unfold.

It was just a short time after that I started having these strange dreams. And in these dreams. I was sitting on top of a flagpole on a flimsy little 12 inch board . As a kid I slept like a rock. And you literally had to shake me to wake me up. Now I would sit there precariously trying to balance myself on that small board. All of a sudden the board would break and give way. And the flagpole would go straight up my ass.You heard me. Straight up my ass. And it hurt like hell. And it was as though the flagpole was lubricated. And I inevitably could not pull myself up off of it. I just kept slipping further down. And it just kept sliding further up my young ass. But! Oddly enough the further up my butt it went, the pain began to disappear. And was replaced with a wonderful desirable pleasure. After 3 or 4 of those dreams. I actually began to think to myself during the day. I hope I have one of those dreams tonight.

Yep! I began to like it. A lot! I look forward to it. And eventually it led to my self exploration of a pleasure I did not know exist inside my body. And overnight I began to wonder and imagine the wonderful use of that seemingly inconvenient little hardon that I woke up with with every morning. The event without doubt woke up my sexual exploration and desires. Which led to some interesting overnight stays with friends and cousins. I even experimented with various length and shaped objects. Then it happened. In my young years while strangling that proverbial chicken. Or spanking the monkey. Or what ever you call it. I went beyond that burning point of pleasure to my first full-blown Climax. And it was a load that seem endless, as though it had been building up for years. And, I guess it had.

Now satisfying myself by masturbating and at the same time fulfilling my anal desires. Led to some difficult to find moments of intimacy. It was something you just did not want to get caught doing. And I had learned very quickly that having something my ass pleasured while I climaxed at the same time. Not only was painful to my ass. But diminished the pleasure of my climax. Which was a bummer. Because I like doing both at the same time. And if not for that moment of pain. It would have been the perfect orgasm.

But that’s not where my problem really laid. I liked girls. I liked them a lot. I like everything about them. Especially getting them naked and on their back. Especially when I found out they had orgasms too. So I had plenty of sexual partners. But not one of them was a trustworthy male that could help me with my unfulfilled anal needs. I needed and wanted a good hard cock in my ass. And I could not trust the discretion of those I experimented with before. We had gone from the boundaries of experimentation. To calling those that did faggots, queers and homos. Name tags you did not want associated with you.

Then I met him. Well, sort of. We had moved into an old logging community. Where there was plenty of dairy farms and timber mills. You know, those 70 to 80 percent people. Well he was different. And much older. So there I was, very much still wanting. And still looking for somebody to fill that need.Time passed by. And as it did, I notice not many people visited him. And then one day one of the local teens told me you could get free candy from him. Well I had heard stories about grown-ups who gave candy and beer to young people. And was quite aware of what it meant. In the unorthodox sexual way. So one day I just boldly walked up to his door in broad daylight. Knocked. And when he answered. Asked for a piece of candy. To which he responded. All I have is mints! And I really don’t know you. Then he closed the door.

Turns out it was just bad timing. Broad daylight wasn’t a bright idea. And not on the weekend when parents hadn’t left their kids to go tip a few at the local bar or party. And leave them alone for the weekend.But something told me. That he knew what I meant, when I asked for a piece of candy. So every evening around dusk, just as it starting to turn dark. I would walk up on the hill along the backside of his property close enough to get a good view through his bathroom window. And watch him go for his nightly shower. I didn’t think he could see me. But then again I hope that he would. He would strip and get ready to shower. Seemly making sure that he turned to right angle to display his well proportioned. (At least to me) erect manhood. Balls and all. It looked perfect. I had learned that I could not take anything more than 5 inches. And was looking for something like his. Hard, erect and that bulge he had that was at the base halfway down his cock. Just made me raise up a hardon fast. I wanted iBut I knew shoving something like that in my backside to fast was going to hurt. And it was no fun having pain disrupt a moment of pleasure that anal sex can give. So I plan to my strategy. When it happened. And I knew it was going to. I was going to have to take charge of the moment, to make sure I didn’t end up face with that cock crammed in me too fast to adjust to.

Will they say time favors those that are prepared. And I don’t know how that exactly fits into this. But. It turns out that my mom and dad knew this man. He was famous around town for making costume jewelry. And bought quite a few rounds down at the bar. So one night on the weekend right. Right after I finished my Friday homework early that evening. I was informed by my mother and father. Then I was going to be babysat. Which was embarrassing. I was plenty old enough to babysit myself. And I let them know it.

No arguments. Your brother is staying with your cousins. And you’re staying with a friend of ours. Were not leaving you here by yourself all night to drag some friends or some girl over. And we won’t be back until the morning. You’re going to spend the night with Mister Fleishman. I about shit my drawers. And pop a hardon at the same time. I knew that last name. That the man I had been eyeballing. And lusting after. Bingo! I was going to get nailed. And I knew it. So I pretended to be disappointed. As I gathered up my clothes to go to Mister Fleishman’s house, All by myself. To knock on that door once again.

When I found myself there. I hesitated to knock. But took a deep breath. And knocked on the door like I was a man. He opened it almost immediately. With his big smile on his face. And the words. Well, come on in. Let’s talk. I couldn’t help but smile. And said, with an apprehensive breath. Okey-dokey. My balls begin to almost immediately roll in anticipation of building up a load that I hope was going to be well spent. And was wondering how much he was going to give me in return.Your mom and dad have already driven out to go partying. I saw them cross the bridge. So they are well underway to town. To which he locked the front door. Then turned to me and said. How do you want to do this. And I was glad he asked.I asked him where his bedroom was. He took a deep breath. That I could tell was one of relief. He pointed over toward his room. I took his hand and told him. I want to start this off. If you don’t mind. I won’t hurt you he replied. I told him, I believe you. To which he responded. Ok, You’ve got the rains. Let’s see if we can get this horse in the barn. I kinda gulped as I swallowed my own saliva. And nodded. Then led him to his own bedroom.

We both knew this was going to happen. And we began to undress ourselves individually. As I stood there with a hardon more than a good inch bigger than his. I marveled over the idea that what I was looking at between his legs up close. Still looked look like exactly what I wanted. Should I lay down, he asked? Yes, please. He laid down under the covers. Which added even more excitement to what was about to take place. I crawled up under the blankets from the foot of the bed, like a nervous ninja. And proceeded to wrap my mouth around his rock hard cock. He moaned with pleasure. Which made me relax. As I began my mouth and to bob up and down his manhood and in and of my mouth, like I had seen in videos and read in porn magazines. Except I wasn’t a girl.

I continue to bob up and down on his tool. As I cunningly removed saliva from around my mouth and his shaft and work it into my ass. After I had loosened myself up. I took it out of my mouth. It slid up forward toward putting my head on his chest. And reached back and took hold of his rock hard cock, as I listened to the heavy breathing.

I placed the head of his rod at the opening of my ass. And pushed slowly until the head of his cock popped into my still tighter than expected ass. He lay there almost motionless. Looking straight up at me. And I smiled back. Just give me a minute, I said. Take your time, he said in return. And with that. My butt hole muscles began to relax and except the stretching. And I begin to push harder into my butt. I could feel the head of his cock pressing against that second opening. And then begin to ease it through. This was the point of no return. There was no way I could, or wanted to stop now.Then slowly set up straight, and began to work the the head of it slowly deeper into my ass. It was more difficult than I thought it was going to be. The way it looked and the way it felt were two different things. But I was determined. And eventually my anus began to give way. I won’t lie. It did hurt some. Not a great deal. But enough to make me pause to take time to relax. Deeper and deeper I worked him into me. Then I buried him until the tip his full staff perfectly hit bottom.

I had felt the pleasure that bulge slip up into me, as my ass cheeks settle down on his hairy groin. It was perfect. I moved up and down his shaft 10 maybe 11 times. Then with deep breathing in my chest I placed my hands on his chest. And told him. Okay. Just tell me what position you want me in. Face up or face down. On my hands and knees. You let me know. “You take over.” Much to my surprise his muscular hands reached up and took me around the waist and my hips gently and rolled me over on my back. And he began to thrust himself in and out of me slowly and gently. Then something in my balls and penis began to stir. I couldn’t believe it. But as he pushed himself in and out of me. I could build fill myself beginning to build up to a climax. Without even touching myself. This I did not expect. But the more he pushed himself in and out of me. And the faster he did, the more the inevitable a climax was building up in me. If he kept fucking me like this. I was going to blow my load.

It wasn’t long until he coaxed me up on my hands and knees. And began to push himself in and out of me. He even had me lay down for a brief fucked on my belly and did me as I lay face down. The muscles in my ass tightened up. And my climax began to come closer. He brought me up onto my knees again. And began to move in and out of me faster and faster. He was building up too. And with every stroke we each drew nearer to a climax. Finally I could fill the rhythm of his thrusting breaking and becoming uneven. As he started coming close to that ultimate moment. And I felt myself doing the same. And with a few final thrust banging deep and hard against my ass. He drove himself deep into me as he possibly could. The pumping sensation of his climax shot hot streaming pulsating squirt after squirt of cum inside. I blew my load! And each time I shot. My ass musles would suck his cock up into me and he would moan as he came more and more. And with each pulsing shot. I would squirt more cum out of my cock on to my chest and even on to my chin. Barely missing my mouth. But leaving me with the desired to take my tongue reach outside of my mouth and lick some of the dribble off the side of my chin.

He finally stopped squirting. A slowly lowered me down to lay face down on the bed, which was soaked with my own cum all over from beneath my belly and on the sheets too. I had messed up his sheets from my belly to the top of my chest. And as I thought of how I was going to explain that to him. He asked me. How did you do that? Do what I asked. You know. Suck me up inside of you. I don’t know. All I know was the moment that you came. You made me cum too. And each time I did. It made me pull you up inside me. Well we’ll talk about that later, he said. For now let’s get you cleaned up. I dumped a truck load up inside you. Yeah I know. It felt like you could’ve filled up to couple of shot glasses. Sorry I should’ve warned you. No, no I don’t mind! I thought it was great. Yeah? Yeah I said . We smiled at each other. And he helped me get up. Trying to keep his self still inside me as he began to shrink down.

We made it to the bathroom. And he helped me into the shower. Where I could let it drain from me. And he turned on the water to a nice warm temperature. And we both began to bathe, and even wash each other. I told him about the sheets. And he laughed. Don’t worry. I’ve got plenty more. And as we washed each other. He paused to look at the cum stream he had left inside me drizzling down my legs. And as I watched him. I caught a glimpse of his cock twitch, and begin to swell up again. I said with quite a surprised look. Again? To which he responded. If you think you can? I looked up at him and with a slight smile. Said, Oh yeah! And I dropped down to my knees. And so it began. “The Flagpole Sitter, had arrived.”

To be continued? Let me know. 🙂

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