"Correct answer," he says before landing another forceful whack.
My legs start to quiver, and tears sting my eyes. I wish I knew how many of these blows he plans. I can maybe last seven or eight more of these. After that, I'll seriously have to consider using my safety word.
"Do you think I should go easy on you because you're new?"
I readjust my number after the fourth blow. There's no way I can take seven or eight more of these. My ass will break apart before then.
"Well, Virginia?"
I whimper, "No, Sir."
I cry and shake against the pillory with his next strike. It's like he's trying to hit a fucking home run on my ass. Maybe I should've responded that I preferred the stinging sensation.
"You should thank me for the punishment I'm giving you."
"Thank – thank you. Sir."
I feel something smooth against my folds. Whatever it is, he rubs it back and forth along my slit, coating it with my juices. It's not the vibrator. It feels smaller. It is smaller. He presses it inside me until my pussy swallows it whole.
I jump when the vibrations start. It was novel enough experiencing the vibrations on my clit, but now they're inside of me. No matter how my body twitches or jerks, it can't escape the vibrations. I start to pant. My legs want to buckle. And then the vibrations stop.
"Hold still," he instructs.
Whack!
The force of it sends me onto my toes and slams me again into the pillory. My lower back feels tired from being in this position. I make a note to myself to do more core exercises.
"Do you like your punishment?"
"Yes, Sir."
"Would you like more?"
It's a trick question. I groan, "Yes, Sir."
The paddle bites into my ass, pushing tears out both eyes. I consider the safety word, but the vibrations are back, making me reconsider. If I use my safety word, there's a chance I won’t get to come. And I want to come. I suffered enough. I deserve to come. I want to show him I can do this. I want to meet or exceed his expectations. And the money would be nice, too, if he’s sincere about me earning it, but that reward is a secondary consideration in the moment.
He lets the vibrations go for several minutes, letting them build my arousal toward my climax. Yes! This is going to be so worth it.
He spanks me with the paddle while the vibrations are going. Yes, yes!
But then the vibrations stop.
"May I come, Sir?" I remember.
"Not yet. We haven't gotten to the stinging sensations."
I hear him set aside the paddle. A whip cracks the air. I clench my hands and brace my body. To my surprise, it doesn’t sting as much as I'd feared. Back and forth, it smacks one buttock, then the other. In the same manner, the whip travels down my thighs, slapping one side, then the other.
But that was just the warm-up.
There's a break in action, an ominous pause before the whip slices across my bruised and battered bottom. I shriek. He whips me again. God Almighty!
The vibrations return, making the next several falls of the whip more bearable. But I wonder how much more I can take?
The whipping stops. A minute later, I feel his legs behind mine. His cock is at my opening. Before I can remind him about the vibrator thing inside of me, he pushes into me.
O. M. G.