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“First I’m going to get you warmed up,” I said. I reached over to the end table and grabbed a bottle of lube of squirted some of it on my index finger. “I don’t want to break you in half, at least, not in the beginning,” I said.
“Thank you, mistress,” Jason said.
After I’d coated my finger with the lube, I rubbed the outside of his anus with the tip of my finger.
Jason moaned softly.
“You like that, do you?” I asked.
“Very much, mistress,” he replied.
“Well, let’s see how you like this,” I said, suddenly jamming the tip of my finger inside his asshole.
Jason let out a low gasp and gritted his teeth.
“Not so much, huh?” I said.
Jason just shook his head but I let it slide.
“Don’t worry,” I said. “Your asshole will loosen up real quick.”
And it did, along with some help from my finger. I slid it in and out of Jason’s anus for a bit, then held it halfway inside him and wiggled it around, getting him loosened up.
“Are you ready for another one?” I asked.
“Yes, mistress,” Jason said.
Smiling, I slid another finger inside him. Again he gasped and flinched, but just like before, after a little bit of working it, he was able to take both fingers inside his asshole without too much discomfort.
“I think you’re ready for the real thing,” I said after a full minute of working his asshole with my fingers. “What about you, big boy? Do you think you’re ready to take my cock in your ass?”
“As ready as I’ll ever be,” Jason said.
I tilted my head slightly and giving him an admonishing look. “You don’t sound too enthusiastic about it,” I said. “I don’t think I like that.”
“Sorry, mistress,” Jason said. Then, in a more upbeat tone, he said, “I can’t wait to have your cock in my asshole.”
“That’s better,” I said, looking down a
t his wide open legs and tight little asshole.
I grabbed the bottle of lube from the end table and squirted it all over my cock. Then I worked it in with my hand, jerking myself off as Jason looked on.
“All right, big boy,” I said. Holding my cock tight, I moved my hips towards Jason until the tip was just barely touching his asshole. “Here comes the moment of truth.”
I pushed forward, inserting the tip of my cock into Jason’s anus. He let out a gasp and followed that with a long, slow exhalation of breath. Smiling widely, I looked down at him, getting off on the discomfort playing upon his face.
“Don’t push me out,” I said. “Don’t push my cock out of your ass. Keep it right fucking there, understand?”
“Yes mistress,” Jason managed to say.
“It’s not so easy, is it?” I said. “It’s no piece of cake taking a dick in your ass, is it?”
“No mistress,” Jason said through gritted teeth.
“Don’t worry,” I said. “Just relax. It’ll get easier soon enough.”
I worked my hips slowly, giving him no more than a quarter of the dildo per pump. But still, Jason seemed to be struggling with it, so I decided to help him out a bit by playing with his cock while I fucked his ass. After all, if he couldn’t get past this first part of the session, I’d have no opportunity to give it to him like I wanted to. And that was no good.
