Old wooden ladder

As luck would have it, he found his dad's old wooden painter's ladder leaning against the side of the house. "This will work just fine!" Dylan thought to himself as he positioned the ladder to climb on the roof. The wooden legs were wobbly and provided little support for Dylan as he ascended the creaking steps. As he reached the pinnacle of his climb, the ladder finally lost balance and sent Dylan toppling over toward the house.

As luck would have it, he was able to land on the roof just in time before the ladder fell sideways into the grass and he lifted himself up with his arms just as he did earlier in the pool. However, misfortune also played a role in all this as his crotch was mashed horribly into the corner of the roof knocking his marbles around inside their sack as he did his best to keep his arms stable and regain his upper body strength to pull himself up.

Once he was finally on the roof, he sat along the incline for a moment overlooking the pool. His balls and bare ass cheeks were subjected to the painfully rough surface of the high grit shingles on his parents's roof. He laid back and started to weep for his aching manhood.