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As Jake lubes up, with lots of lube, I joke that after this, he may become a tranny; Jake is more concerned about having enough lube up him. He says, "if it looks like it hurts, I'm not acting." Jake taking Diesal's monster cock is a slow process. "Damn, it's tight as fuck," Diesal says, over the sounds of Jake's heavy breathing. I don't think Jake is a bottom; the pain he feels, and his face, confirms my suspicions. "Do you have to go any further?" Jake asks Diesal, "nope," Diesal responds. At this point he is only in about one-third of the way. Jake switches between moaning and whining. A few minutes later, Diesal is going at a steady pace and Jake seems to be relaxing, somewhat. Most of this whole time, Jake's face has been in the pillow under him. I see he is now lifting his head to breathe; maybe he will enjoy it on his back.