“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.
“Yes, mistress,” Jason said again, louder this time.
“I want to hear you say it,” I said, glaring down at him with an annoyed face even though I was thoroughly enjoying myself, and especially Jason’s discomfort. “Tell me I’m the best dick you’ve ever had.”
“You’re the best dick I’ve ever had,” he said between gasps and moans.
“That’s what I like to hear,” I said, smiling sweetly now.
I leaned forward so my body was lying atop Jason’s and my face was right above him, no more than two inches away.
“Tell me you love it,” I said, staring right at him. “Tell me you fucking love it.”
“I love it,” Jason said.
“Say it like you mean it,” I said.
“I love it,” he said with more emotion. “I fucking love it.”
“Yeah?” I said, still pounding his asshole with my cock. “You’re my fucking bitch, aren’t you?”
“Yes, mistress,” Jason said.
“Tell me you’re my fucking bitch,” I said.
“I’m your fucking bitch.”
“Again,” I said. “Tell me you’re my fucking little bitch.”
“I’m your fucking little bitch,” Jason said.
Smiling wickedly, enjoying myself immensely, I bent over a little further and jammed my tongue into Jason’s mouth, roughly exploring around for a few seconds before pulling back.
I loved having all the control, all the power over a man. Telling him what to do, what he was going to do, what he was going to enjoy. It was better than the most addictive drug, as intoxicating as the strongest aphrodisiac. But like all things, it must come to an end, and from the look on Jason’s face and the bulging hardness of his cock, that end was near.
“You want to cum, don’t you?” I asked him.
Jason nodded.
“You want to cum and for this to be over, right?”
“Yes, mistress,” he said.
“Don’t worry,” I said. “It will be soon, I promise. But first I need something from you.”
“Anything, mistress,” Jason said.
“I need you to grab your other leg and pull your knees back a little further,” I said. “Open yourself up more to me so I can fuck you like you deserve to be fucked. Then I’ll help you cum.”
Jason did as he was told, hooking his arm around his other knee and pulling back on both of them so his ass was sticking up in the air.
“That’s a good boy,” I said, lifting myself
