I remained hunched over with my ass in the air while Jamaal lubed up the Boss's cock. I knew I was about to get fucked in the ass for the first time. I knew it would probably hurt, no matter how much Jamaal had loosened me up with his tongue and fingers. However, any apprehension that I had was betrayed by the thin stream of cum dripping from my erect penis.
After Jamaal lubed up the Boss's dick, he put more lube on his fingers and thrust them into my ass.
"Gonna get you nice and ready, baby," he almost whispered. "You'll thank me later."
Once Jamaal was done, the Boss didn't waste any time. He put a collapsed cardboard box on the rough ground in front of him, got down on his knees, and began pushing the head of his big black cock into my rosebud. I felt strong pressure on my asshole until, after some grunting and pushing, the Boss managed to shove it in.
I felt immediate pain and began gasping and whimpering as the Boss continued to push and push. I had no idea how much of his cock was in me but it felt like about a mile. Jamaal leaned down beside me and began stroking my cock, which distracted me from the worst of the discomfort.
After another minute or so of pushing, the Boss stopped so that I could relax around his cock. I had to admit that it turned me on to feel hot hard flesh stuffed inside of me. The Boss pulled his cock out and immediately Jamaal put it in his mouth, sucking vigorously.
"That's good, baby," the Boss cooed. "Suck that ass juice off of me."