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Playing with Jason’s cock seemed to relax him, and it wasn’t long before his asshole was loosened up enough that I was able to give him half of my cock at a time before pulling back.
“There we go,” I said. “That’s better.”
Jason was more into it too, barely even grimacing as I pumped his asshole with my cock. Which meant that I had to turn the heat up. I didn’t want him getting too comfortable . . .
“Grab ahold of your cock,” I said. “Jerk yourself off while I fuck your ass.”
As Jason started playing with himself, I reached underneath his legs and lifted them up and back, exposing more of his asshole to my and giving me better leverage.
“Open up for me,” I said. “Open your legs wider.”
Jason did as he was told.
“Now hook your arm under your knee,” I said.
Jason did this too.
“That’s better,” I said, pausing for a moment but leaving my cock planted halfway in his ass. “Now I can fuck your ass like it deserves to be fucked. Do you like that idea?”
“Yes, mistress,” Jason said.
I rose up on my legs a little bit higher, altering the angle of penetration and allowing my to get my whole cock into his ass more easily.
“Are you ready to take all of my cock in your ass?” I asked.
Jason only nodded but I didn’t care. I didn’t even really need a response from him at all, I was just messing with him.
“Good, because shit’s about to get real right now.”
And with that, I forced the entire dildo into Jason’s ass, giving it to him balls-deep (metaphorically, of course) and holding it there.
“Holy fucking shit,” Jason said between deep, gasping breaths. The pained look on his face had come back with a vengeance and his while his hand was still around his cock, he was no longer jerking himself off. The knee that he had hooked his arm around the back of was mere centimeters from his mouth as he held his ass open for me.
“Keep playing with yourself,” I said. “Don’t let up now.”
Gritting his teeth, Jason went back to jerking himself off.
“That’s a good boy,” I said as I started moving my hips forward and back, pumping Jason’s ass with my cock, giving it to him balls-deep every time.
I gave him the whole dildo in long, slow thrusts at first, but quickly sped things up, pumping his asshole with my cock at a pretty quick pace within half a minute.
It was obvious from the look on Jason’s face that was struggling with it quite a bit. But I didn’t care at this point. I was going to give it to him how I wanted to, not how he wanted it.
“Bite your fucking knee if it hurts,” I said. “Don’t even think about pushing my cock out of your asshole. Bite your fucking knee. You bite your fucking knee if it’s too much for you to handle.”
So Jason did just that, biting down on the skin above his kneecap while I continued fucking his asshole with my cock, giving it to him hard and fast now, hammering the dildo in and out of his anus while he groaned and took deep, gasping breaths.
“That’s right,” I said, pummeling him harder now. “Take that dick. Take it deep inside your asshole.”
Jason’s eyes were closed and his mouth was open but his dick was still hard, which meant that no matter how much it hurt, he was still enjoying himself on some level.
And so was I. Things weren’t nearly as rough as they were with some of my regular partners, but popping a young man’s anal cherry more than made up for the lack of aggression in this session.
“Am I the best dick you’ve ever had?” I asked.
“Yes, mistress, ” Jason said, his voice barely above a whisper.
“I can’t hear you,” I said.
