It started two months before my 15th birthday. I grew up in the arm pit of NYC and had a lawn business. A young couple down the street was my 1st customers and they seemed like “good people.” She’d taken their new baby and went somewhere for the summer and he stayed home. It was a hot August Saturday and after I finished their yard I met up with him in the garage to get paid. We settled up he said he had another way for me to make some cash. Clueless, I said I’d do whatever. He offered me twenty bucks to see my dick; simple as that. This guy was in his late 20’s, had all the signs of being heterosexual, and I didn’t know what to think. But not one to pass up easy money, I said “Sure.” and dropped my shorts and boxers to my ankles.
My cock was starting to grow up and the guttural moan that came out of him confirmed my suspicions about being above average in the size department. It throbbed to a semi, then to a full out rock-hard boner in a few seconds. So there I was, standing half naked, dick sticking straight out. I start leaking when I begin to get a boner and in no time there was a long string of precum hanging off the end of my foreskin. I tugged on my hood, wrapped my hand around my slick cock and beat off just for him. I worked my dong until I couldn’t hold it and squirted a big wad on the garage floor. I could tell that really turned him on, and that in turn really turned me on. He just watched and stared. After I came I pulled up my shorts and underwear and stood there in silence, head spinning from what I just did. He reached in his pocket and gave me the twenty, told me I had a big cock for a kid and if I wanted to do it again, that could be arranged. I left with empty nuts and full wallet. I then became a slightly freaked out 15 year old kid. I scored a bag of weed and got stoned. After chilling out on the dope, I realized that I fuckin’ loved what just happened.
The next time he asked if it was ok if he jacked off too. Again, me with the “Sure” and soon we were both standing there stroking our cocks. He had a nice dick and we nearly shot off at the same time. We got together regularly to jack off after that. It was always in his garage and it was always just jacking off. And it was always hot. When it got close to my 16th birthday he mentioned a “special” present for me. I had a pretty good idea it was going to be sex, but the details were the big mystery. After cutting the lawn on a day when his family was gone, I found him in our usual jack off spot. There he was buck naked, bent over, ass to me and looking back over his shoulder with a goofy grin that I hadn’t seen before. He winked and said “Wanna fuck me, kid?” I was wearing cut off sweats, said “Fuck yes!”, hauled my cock out and pushed it in his pucker.
I’d never felt anything so amazing in my life. He groaned something, and I started to drill his ass like I had been doing it all my life. I took it slow and easy until he grunted back to me “Harder!” So I kicked it up and tore up that manhole. I had no idea fucking ass would be so perfect. He grabbed the wall with one hand and the car with the other, said nothing but grunted and moaned “FUCK ME!” I fucked him in every position we could think of in that garage and I ended up dropping my load pounding him on the front windshield of the car. When he felt my jizz hit his insides he growled, and I felt a tremble deep in his guts. He lifted his hips up, moaned, and dumped his cum.
After he stopped shivering, I pushed his ass back down and pounded a second load up him. When I finally slowed to a stop, he turned and said, “Happy Birthday, kid.” When my cock slipped out of his stretched hole, I said “Thanks” got dressed and left him on the car. This went on until I graduated from high school and went off to college. I hope he reads this.
Courtesy of our TIMFan Robby.