Page 33 of Dark Holiday

Finally, she shakes her head no. “So, you mean to tell me, you can’t pay me back for these missed opportunities? This time, I want you to turn and answer me.”

She turns, her cheeks red and stained with tears. God help me, but my cock hardens as I look at her. “Tell me. Can you pay me back?”

“No, Sir.”

“Then where does that leave us?”

“You could fire me.”

“Already done. We settled that this morning.”

Cindy looks around, desperation rolling off of her in waves. “Please, Sir.”

“Please, what?”

“Just punish me.”

“Oh, that’s also a given, but how shall I punish you, my Little Viper?”

Her head whips up, hope shimmering in their depths. Could it be that she really wants this as much as I do? I wait on bated breath, hoping to hear those magical words. Anything that would indicate that she actually wants me in her life.

“However you see fit, I guess.”

That wasn’t exactly the answer I wanted, but it will have to do for now. “Very well. I want you to come over to the desk and reach across until you’re gripping the other side.”

She walks over, pathetic sniffles in her wake. Standing on her tiptoes, she reaches over to the opposite end and holds on tight. Her ass rubs against my thigh as she gets into position, and I wish I wasn’t such a good man. Given my impulses, it wouldn’t be a belt and my hand destroying her ass tonight. It would be my cock.

I yank her panties to the side with a swift jerk, revealing her asshole and lower lips. She’s already wet for me. I skim my fingers down the taut skin, gripping her bottom in my hands for a moment before spreading her cheeks.

The squeal she gives is far from dignified. Keeping her grip, she wriggles about in a pathetic attempt to get free. Pulling back, I smack her hard across the ass cheek, smiling as my handprint blooms red across the pale surface. “Have you been using the gift I gave you for when you’ve been feeling naughty? Lord knows you must be stretched out by now, given how much trouble you cause me on a daily basis.”

Without waiting to hear her response, I skim my fingers across her bottom hole, smiling as she gasps and tries to pull away. Swatting the other cheek, I wait for her to settle back down before walking over to my drawer. Her eyes are trained on my shaft as it strains against the fabric. The little minx even has the audacity to lick her lips, but only good girls get to taste my cock.

I reach into the drawer and pull out a similar buttplug and some ginger lube. I stashed them away after that first day, hoping to be able to punish her while she worked, but it never happened. Now, I get to have my way with her, and even though she thinks she’s sorry now, she’ll be more so after I’m done.

Ignoring her snuffled pleas, I come back around and open her back up, staring at her asshole for several long moments. In her fear and desperation, she looks over her shoulder, pleading at me with her eyes. The more I stare at her bottom hole, the more her face turns that delightful shade of humiliation that I’ve come to crave. Poor thing doesn’t like me looking there. Letting go of one cheek, I get the ginger lube and open it, letting several generous dollops fall onto her upturned back entrance.

I sit the bottle down and smear the lube across her hole before sliding a finger inside. She shrieks and bucks against me, but I keep my pressure firm and steady. “What’s your choice, little girl? Do you want to pay me? Or would you rather let me have my filthy way with you and call it even? Though between you and I, you’re certainly getting the better end of the deal.”

“I -. Please. Just. Oh, please.”

“Oh, please, what? You’re going to have to use your words. I remember how eloquent you were in speech class.” I slide my finger in deeper, groaning as her hole flutters around me, gripping me. Some day, it will be my cock in there, getting squeezed and caressed despite her protestations. “I used to stand outside on my break and listen to you. You enraptured everyone. Including me.”

More tears fall as a sob racks her body. One way or another, I’ll get to the bottom of what happened that night. This may have started off as a punishment for today’s transgressions, but there’s no way either of us can move forward until we put our past behind us. Pulling my finger out, I slide the tip of the plug in and hold it there, letting her tight ring get used to the cold of the metal.

“But you knew that. Didn’t you? You had everyone at that school wrapped around your finger. It was very naughty of you to play with others' hearts as carelessly as you did.”

“Speak for yourself, asshole!” I choose that very moment to push the plug the rest of the way in, cutting off her exclamation.

“I believe I mentioned something about your language, did I not?”

“What do you care? You don’t want to hear what I have to say anyway.”

“Don’t I? I’ve given you plenty of opportunities to tell your side, and you haven’t said a thing that can convince me you didn’t break my heart on purpose.”

She stills. I take that moment to walk back to the desk and pull out some sanitizing wipes to clean my hands. Soon the ginger should take effect, and she’ll have a lot more on her mind than the lies she’s liable to spew. Once I’m clean, I walk around to her backside, staring at the pliable flesh I’m about to torment.

“Now then. Let’s start with the missed calls, shall we? It is Christmas after all, so I’m in a generous mood.” The venom drips from my lips as I undo my belt. How many years has it been, and still, this fucking holiday cuts me to the core. Taking a deep breath, I focus on the task at hand. I can’t punish her now for all those years ago. That’s not right or fair. If I want any hope of one day being her Daddy, I need to punish her with impunity. I can’t let myself get caught up in old hurts.