“Not so easy, is it?” I asked.
Jason shook his head while still trying to catch his breath.
“What?” I said. “I didn’t hear you.”
“No, mistress,” he replied, talking through deep breaths. “It’s not easy.”
“Do it again,” I said. “And don’t stop until the whole thing has disappeared this time.”
“Yes mistress,” Jason said. He took a deep breath then dove in.
Jason almost had the whole cock down his throat when he started to cough. It looked like he was going to pull away, so I reached down and held the back of his head so he couldn’t move.
“Don’t go anywhere,” I said. “You haven’t taken the whole thing yet.”
Then I pulled Jason’s head forward, forcing the last inch of my cock into his throat.
“That’s a good boy,” I said, keeping my hands on the back of Jason’s head as he gagged and coughed and strained for breath. “Way to deepthroat that cock. Now hold it for a few seconds. Hold it. Hold it.”
Five seconds later, I finally let go of Jason’s head. He jerked back, saliva pouring from his mouth, his chest heaving up and down as his lungs searched for air. Tears were leaking out of his eyes.
“Pretty good job for your first time,” I said, smirking at him. “Did you enjoy deepthroating my cock?”
“Yes mistress,” Jason croaked.
“That’s what I like to hear,” I replied. “Now onto the next stage. Get your ass up here on the couch.”
Jason climbed up next to me.
“On your back with your head over there,” I said, pointing towards the armrest.
Jason got himself into position, his back on the couch, his legs spread wide and his cock standing straight up in the air.
“Good boy,” I said, scooting in closer to him, until my body was situated between his legs. My cock was touching his and my hips were underneath his thighs.
“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 at 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.
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
