“With me?” I asked.
“If you’d have me,” he said.
“I would,” I said. “Under two conditions.”
“Anything,” Jason said. “Just tell me what you need from me.”
“First, you have to understand that today was as mellow as it gets. If you want me to fuck you in the ass again, it’s going to get a whole lot more crazy.”
Jason’s smile grew wider. “That sounds great!”
“And two,” I said, running my finger along his stomach and chest as I did so. “You have to prove to me that you truly want to do this again.”
“And how do I do that?” Jason asked, still smiling.
I altered the path of my finger to collect a good amount of Jason’s cum from his stomach. Once I had a large blob of it on the tip of my finger, I held it out towards Jason’s mouth.
“By eating this,” I said.
Jason’s smile faded quickly.
“Seriously?” he asked.
I nodded.
Jason stared at my finger for a moment, then took a deep breath and said, “Fuck it.” Then he opened up his mouth.
I slipped my finger between his lips. Jason sucked his own cum off my finger and held it in his mouth for a moment.
“Swallow it,” I said.
Jason tilted his head back and swallowed it down.
Smiling, I said, “Good boy,” and stood up. After helping Jason to his feet, I gave him a smack on the ass and told him to go jump in the shower and get cleaned up.
As he walked down the hall towards the bathroom, I said, “And Jason?”
He turned around. “Yes?”
“You did good today.”
“Thanks,” he replied, smiling shyly. “You were incredible.”
“My pleasure,” I said, staring at his tight little ass as he turned and headed towards the bathroom.
I wasn’t one for letting men fuck my anymore, but I might just make an exception in Jason’s case next time. After I’d fucked him first, of course.
#
One week ago to the day, I fucked Jason Davis in the ass for the first time. I’d taken it easy on him, not wanting to get too aggressive, but after the night was over, I realized I’d taken it too easy on him; Jason could have easily taken more. So this time I was going to give him all he could handle, and then some. Tonight I was going to take things to a new level.
#
We were in my living room, in the middle of the floor. Jason was on his knees on the carpet, naked, looking up at me, towering over him in my black, full-bodied leather outfit and thigh-high leather boots. Strapped to my waist was a big, black dildo, seven inches long and the width of a flashlight. I was slowly stroking my rubber cock, staring down at Jason.
“Do you see what I have for you today,” I said.
Jason nodded his head. There was fear in his eyes but it was mixed with a healthy dose of excitement. Exactly what I wanted to see.
“I told you I had a surprise,” I said.
“It’s fucking huge,” Jason said. “Bigger than last time.”
“That’s right,” I said. “And you know why?”
Jason shook his head.
“It’s because I know you can take it, Jason.”
He laughed under his breath. “I don’t know about that.”
“But I do,” I said. I bent down until our heads were on the same level. Then I grabbed ahold of his chin and squeezed tight. “Because you’re a man, right Jason? And men are tough. Isn’t that right Jason?”
“I guess,” he said.
“Don’t give me that shit,” I said. “You think you’re tougher than me. You know it, and I know it. Right?”
Jason reluctantly nodded.
“Which means you can take whatever I can, right?”
He nodded again.
“And considering I’ve taken a cock this size up my ass many times, you can to, right?”
Defeated, Jason nodded again.
“See?” I said, beaming. “My logic is unassailable, right?”
“It certainly appears to be.”
“Which also means that you can take other things that I’ve taken, right?”
At that point Jason appeared to just give up. He just said, “right,” in a flat tone.
“Oh, don’t look so sad,” I said. “I promise not to do anything to you that hasn’t been done to me before. And I’ve come through it fine, so I’m sure you will too. All right?”
“All right,” he said.
“Good,” I said. “So are you ready to get started?”
Jason nodded.
And without another word, I bent down and slapped him in the face.
Jason took it like a man, hardly making any sound at all beyond a little grunt.
“Very good,” I said, smiling. Then I slapped him again. Harder this time.
But still Jason barely made a noise.
“Did that hurt?” I asked.
“A little,” Jason said.
“Just a little?” I said.
Jason nodded.
“Then I guess I’m not doing it hard enough,” I replied. And I smacked him again. And again. And again. The sound of flesh on flesh was like a gunshot echoing about the room.
After the sixth consecutive slap to the same side of the face, Jason cracked, letting out a loud groan and following it with an f-bomb.
“That one got to you, didn’t it?” I said, grinning like the devil.
“Yeah,” Jason said. His cheek was bright red and his breathing rate was ragged and tears leaked out of his eyes.
Laughing, I grabbed a handful of his hair and yanked back on it, exposing his neck to me.
“Do you want me to stop smacking you? Do you want me to do something else?”
“Yes please,” Jason said.
“Fine,” I said. “But don’t say you didn’t ask for it.”
“I won’t.”
“Then open your fucking mouth,” I said.
Jason did as he was told.
“That’s a good boy,” I said. And
