I can't forget all those times I went into the woods with my friend Corey, two years younger than me, to jerk off until we were sore. You can search JACKIN' WITH COREY for the true story.
It was so intoxicating, so bad, so naughty, Jackin' with Corey. I can't get that feeling anymore. This is why I think about the old days way too much, me and Corey, comparing dicks, stroking away, spurting, being grossed out and running our separate ways.
I remember teaching him how to do it. That was cool, very cool, his dick with such a tiny wisp of hair, his curosity, his smile when he got it right and came for the very first time.
This brings me to now. I have my own pool and it's time to clean it and get it ready. I like to do these things early, when I have the money. The pool company sent a kid over who looked way too much like my childhood crush, Corey. I'm not gay, but I know that I wouldn't have minded kissing Corey a bit more, more passionately, longer, less scared.
This kid must have been 18 or 19 with a wisp of a mustache and a flat, hairless tummy. Ummmm! I thought. After awhile, he noticed me looking and went straight to work.
Needless to say, I had the scene set up. I left some porno mags out where pool boy could find them. I run out there and tell him I'll be back before he's done to pay, maybe half an hour. Secretly, I was inside watching through a window, back in the shadows, so I know he couldn't see me. I was hard as a rail as the kid stopped working long enough to look over and notice the magazines. He took the bait! He started thumbing through one and rubbing at the enlarging bulge in his pants. This reminded me of my old childhood pal to a degree and that got me even harder. Then the kid took out his boner and stroked it a couple of times before dropping his shorts and underwear all the way to the ankles. To my surprise, pool boy could suck on the tip of his own cock. I could almost just about hear the smacking, sucking sounds. Seeing him do it, suck his own dick like that made me hot. It made me hot and jealous. It got me to the edge and pretty soon my body crashed to the knees from a powerful little secret orgasm. I shot my load everywhere. It damn near hurt, it felt soo good! I looked up to see Pool boy stroking real hard, looking at the porno and then he came with a moan that I'd love to have on tape. It was deep all right, deep and unplanned. I got one last spurt out of my cock and looked up to see Pool boy was just now pulling up his shorts, with a sticky strand of cum hanging down from the tip. Wow! What a day!
Three months later I got up the courage to call for the pool boy to come by and check the filters, maybe skim some leaves from the pool, and I did the same thing as before. New magazines and some lube. As he began to stroke himself, I could feel my balls aching for release. I'd jacked off a thousand times thinking about that first time, pool boy spurting his 19 year old cum everywhere, me inside, hiding, spurting, my ass spitting to my orgasmic contractions. First and only time for that!
The second time, pool boy used the lube. It was glorious to see his fist flying so quickly over his meat. I came out of my hiding place and came all over the place, gasping, falling to my knees, ouch on the hard concrete. The orgasm subsided. I looked up to see pool boy looking over at me, smiling as he shot his load high into the air. I had a tiny flashback to my jack off buddy from the 1970's, Corey. Embarrassed, I got up and ran back inside. Pool boy was not to be deturred. He came barging in and said that what we had done was absolutely fantastic. He said he liked to jack off all the time. But being watched was the best. He said he liked being watched and had hoped to be caught that first time. I hadn't the guts to tell him I had been watching.
That's when he told me his sister caught him jacking off one time and used to say she would tell if he didn't do what she said, usually jack off and spurt his load into a cup that she made him drink dry. By then it was cold and gross, but pool boy drank. They masturbated together, but his older sister was always the boss, making him rub here, rub there, allowed him to poke her pink wet hole.
I liked pool boy's story. It made me want to jack off again. I started to rub myself through my shorts. In no time I was rock hard. I looked over to see pool boy taking it out. We both pulled down our shorts and did it again while standing up. I didn't like standing up as much as squatting down, which was just all right by pool boy, who said he wanted to spurt his load on my face. He did and it was a lot. I spurted mine on the floor and that's that. I gave him the check and a tip of twenty cash for his trouble.