It wasn’t quite the piledriver position, but it was close. And from here, I could force my cock deeper into Jason’s asshole than it had been all night.
“It’s time to take the training wheels off,” I said. “It’s time for you to see what it’s really like to get fucked in the ass. That’s what you want, right?”
“Yes, mistress,” Jason said. But he didn’t seem too enthusiastic about it. Which was fine by me. At this point, I could care less how Jason felt.
I put my legs in front of my hips and scooted forward, giving myself the best angle to stick my cock deep in Jason’s ass, then pushed my hips forward, jamming the dildo deeper into his ass than it had been all night.
Jason yelped and flinched and his eyes widened suddenly.
In a condescending tone, I said, “Oooohhhh, poor baby, was that too much dick for you?”
But I didn’t let Jason answer. I just continued pummeling his asshole with my cock, driving it deep into his anus, slamming my hips into his asscheeks with every thrust.
“Take my cock,” I said, growling the words now. “Tell me you can take my cock. Tell me you can take all of my cock.”
“I can take it,” Jason said, barely able to get the words out. “I can take all of your cock.”
“Yes you can,” I said. “Yes you can! You’re a good little boy, aren’t you? You’re a good little ass slut!”
“Yes I am,” Jason said. “Yes I am!”
“Say it!” I said. “Tell me you’re a good little ass slut!”
“I’m a good little ass slut!” he said.
“That’s better,” I said. “Now jerk your cock off. Jerk yourself off while I fuck your asshole.”
Jason did as he was told, just as he had been all afternoon. But he didn’t seem to be making any progress towards cumming, so I decided to help him out.
“Do you want me to help you cum?” I asked.
“Yes please,” Jason said.
“Yeah?” I asked. “Do you want me to jerk you off so you can cum?”
“Yes, mistress.”
“Then move your hand,” I said.
After Jason released his cock, I reached over and again grabbed the bottle of lube. While still fucking his asshole (albeit more slowly for the moment) I squeezed the bottle, squirting the liquid all over Jason’s cock. Then I dropped the bottle and worked the lube all around, coating his cock with it.
Once that was done, I went back to fucking Jason’s ass with a renewed intensity, giving it to him balls-deep again, pummeling him with my cock, bottoming out with every thrust.
As Jason grunted and groaned, I went to work on his cock, jerking him off just as aggressively as I was fucking his ass, the lube coating his cock making my job easy.
“Holy fucking shit,” Jason said, clearly going through a wide range of feelings from the look on his face—part excitement, part pleasure, part pain, and part confusion.
“You like that, baby?” I asked. “You like when I jerk you off while I fuck your asshole?”
“Yes, mistress,” Jason said. His eyes were wide and his entire body was quivering as though is was hooked up to a low dose of electricity.
“Tell me,” I said, my hand flying over his rock-hard cock. “I want to hear you say it!”
“I love it when you fuck my ass and jerk me off!”
“That’s it,” I said. They were both talking loudly now, if not quite outright screaming. “Are you ready to cum?”
“Yes, mistress,” Jason said.
“You can cum whenever you want,” I said. “But you’re going to have to do it while I’m pounding your asshole. Do you think you can do that?”
“I don’t know, mistress!” Jason said. He was breathing heavily and his whole body was heaving. “I don’t know!”
“Well, if you want to cum that’s how it’s going to have to happen,” I said, smiling down on him like a demon.
Jason’s eyes were closed now and his face was screwed up in a grimace. He was obviously trying to cum but not quite able to get himself there.
I watched him struggle with it for a minute while still hammering away at his asshole and jerking him off like a madwomen before finally taking mercy on him. Reaching out with my free hand, I cupped his ballsack and started to rub his testicles.
Jason’s eyes immediately opened wide and a gasp of pleasure escaped from his throat.
“I take it you like that?” I said.
Jason nodded. At this point, I doubted that he could talk at all.
“Is it going to make you cum?” I asked.
He nodded again, more emphatically this time.
“Then cum for me, big boy,” I said, putting everything I had into working him over, fucking his ass, jerking him off, and rubbing his balls together all at the same time. “Cum all over yourself for me!”
A few seconds later, Jason’s entire body tensed up, then released. He cursed under his breath and let out a long, low groan as his cock shot out stream after stream of white cum, sending it up into the air only to splash down on his stomach and chest.
Leaving my dildo planted in Jason’s ass, I continued to work his cock and balls until they were completely dry, squeezing every last drop out of them before releasing them from my grip.
As Jason shuddered and tried to catch his breath after his intense orgasm, I let my cock slip out of his asshole.
“Well, what did you think?” I asked, smirking down at him.
“I think that was fucking insane,” Jason said. His mouth was fixed in a goofy, exhausted smile.
“Did you enjoy yourself?”
“Hell yes,” he said. “I fucking loved it.”
“Is it something you might want to do again?”
“Not right away,” Jason
