Despite the excited thrill that shot through my chest, I thrashed beneath him at his words. He tightened his grip on the belt, forcing me to stop struggling.
“None of that. I’m going to need you to relax for me. I don’t want to accidentally hurt you.” He crooned, and I panted. My entire face was definitely beat red from the choke hold he had on me with the belt.
“Now, I’m going to ask you some questions, and you’re going to be honest with me. If you answer correctly, you will be rewarded. If you answer incorrectly, you’ll be punished. Understand?”
“Fuck…you!”I snarled, and he chuckled before slapping my ass so hard I fucking barked out a shout of pain.
“Fuck!”
He rubbed my stinging cheeks gently as I squirmed beneath him. My hard cock leaked and rubbed into the grass every time I moved.
“Strike one, Ryan. Are you going to be good? I can do this all day.”
I found my hips were inadvertently grinding my dick into the ground. I was desperate for the friction. My mind was numb and almost blank. All the anxiety I usually felt about daily life stressors was weirdly absent, and all I had to do was listen to Cal’s voice.
It was strangely… freeing.
“Fine,” I spat, feigning an anger that I didn’t really feel. Cal’s deep masculine chuckle rolled through the air again.
“Good enough. But we’ll need to work on that tone,” he said as he lightly dragged his lubed-up fingers up and down my crack.
“Now, for the first question… Have you ever played with yourself back here? Remember, no lies. I’ll know if you’re lying.”
The memory of experimenting that one time in the shower hit me like a Mack truck, and before I could stop myself, I found I was nodding.
“Yes. Once.”
“Mmm.Good boy, Ryan,” he praised, and he slid his wet fingers in between my cheeks. The lube made it so smooth and slippery. Suddenly, he was making direct contact with my asshole.
My cock throbbed beneath me, and I whined, arching back into his touch. I wasn’t sure if it was so I could rub my dick into the ground harder or encourage him to penetrate me. It didn’t matter; it seemed to be the right thing to do. Cal was clearly pleased with my reaction.
“Who were you thinking about while you did it?” His fingers danced and teased around my hole, and I was panting with anticipation. I wanted him to put them inside me. I wanted it so bad. My whole body was on fire.
“You, okay!? I was thinking of you.”
“Fuck.” Cal groaned, and he lined one finger up with my hole before putting pressure on it. Not enough to penetrate but fuck, it was so close. “You’re being so good. One more question before your reward.”
I nodded, barely able to speak anymore. The anticipation was killing me.
“Next question. Do you want me to put my fingers inside you?”
I nodded again.
“Say it, Ryan. Tell me you want me to stick my fingers in your tight little ass.”
My cheeks flushed with embarrassment, but I swallowed it down.
“I want it. I want you to put your fingers inside me.”
It was the truth. I did fucking want it.
“Since you asked so nicely… Take a breath, and relax, baby,” he coached me, and I hurried to do as I was told.
The pressure increased on my asshole, and he made soothing sounds as his finger finally pushed past the tight ring of muscle.
I cried out as he entered me, adjusting to the strange new feeling.
“That’s it, baby. Let me in,” he cooed, and I found myself alternating between humping the ground and pressing back into his finger.
