Weely Punishment

It's Saturday and once again I'm standing in front of him, awaiting my punishment.

Sitting in the chair in the corner of the room, dressed sharply all in black, he casually sips his bourbon and eyes me up and down. In just my bra and jeans, I nervously shift my weight from one bare foot to the other.

As usual I've texted him a list of the weeks transgressions for his review, and I listen now as he reads them aloud from his phone.

"5 minutes late to work on Tuesday, and 10 minutes late on Friday. 20 minutes unauthorized play time on Thursday," he pauses to stare at me disapprovingly then and continues, "and 35 minutes unauthorized playtime on Friday."

I nod slightly in acknowledgement and bow my head in shame. Swallowing hard I try to clear the lump in my throat. Tossing his phone aside he stands and moves toward me slowly and places is fingers below my chin tilting my head up, he forces me to look at him. He is calm but serious and meeting his intense gaze makes me feel penetrated and vulnerable.

I know it's no use but the silence is too much, so I blurt out a quick apology anyway. "I'm sorry, Sir."

Unamused, he shakes his head at me.

My stomachs churns with anticipation. I know he will dole out the punishment that I deserve fairly but I also know it will be difficult and likely painful and unless I safeword, all of my crying and begging for mercy will not make him stop. His determination to hold me accountable is never deterred by my pleas. Once I've earned a punishment, there is no getting out of it.

"These are not new mistakes, slut. You seem to be repeating the same bad behavior. This can only mean one thing...I have not been harsh enough on you," he explains.

My stomach churns again, audibly this time. I look at him with trepidation and again apologize, "I'm sorry, Sir."

"Save it," he dismisses. Releasing my chin he steps back and with a nod, directs me to the corner.

I walk slowly and position myself with my nose in the corner and arms folded behind my back. I wait patiently as he prepares, the suspense making time move slow. Listening to his movements I try not to imagine the misery he has planned for me.

I'm sure it has been at least 10 minutes before he calls for me, but in reality, it's probably much less. "Come on naughty girl, let's get on with this."

I turn to find him sitting on the side of the bed, he gestures me to stand in front of him and I quickly obey. "What do you need?" he asks.

I know what he wants to hear, and I answer, "I need to be punished, Sir."

"Good, we'll start with an over the knee spanking. You do not need to count. Tell me, how do naughty girls get spanked?"

I blush and shyly respond, "on their bare bottoms, Sir."

"Good girl," he replies as he reaches out to undo my jeans. He slides my jeans and panties together down to my thighs and pulls me quickly over his knee.

The spanking starts immediately, his hand bouncing back and forth between my cheeks. It stings but the pain is tolerable.

"Do you know how many times you have been late for work this month?" He doesn't wait for an answer, "Nine. Nine, fucking times in one month! Do you think that is acceptable?!" His pace quickens and the lecture continues. "Do you think that just because you work from home you can take advantage and start whenever you feel like it?!"

His hands pepper my ass and the sting builds until my legs begin to kick. He throws his other leg over mine and holds them firmly in place. "This is just a warm up little girl, save your struggling."

I wince and squeeze his pant leg, knowing reaching back to cover my ass is not acceptable. Finally it stops and I take a deep breath, only to discover that he has grabbed the hairbrush now. It smacks against my flesh and I jump at the impact. The pain builds with each blow and it takes all of my self control not to reach my hand back and protect my poor ass.

Finally, the hairbrush is tossed aside and I am relieved. His hands slide over my tender ass and then down between my legs. He takes a moment to check for wetness and I blush, knowing he will find it. His fingers run up and down my slit and gather the moisture. He grips my hair tightly with his other hand and pulls my head upward. His wet fingers are pressed to my lips and I obediently suck them clean. "Shameful," he scolds and I nod in agreement.

He pulls me upright. "Your lateness has earned you 20 with the cane this time," he explains.

"Yes, Sir."

He instructs me to bed over the bed and I comply. Soon I feel the cane tapping lightly against my ass. "Count," he orders.

The cane pulls away and comes back hard and sharp. The pain is intense and I jump before crying out "one, Sir."

Again, it lands and I squeeze the bedspread between my fingers and grit my teeth, "two, Sir."

He continues without pause as I struggle to hold my position, keep count and hold back the tears. The 11th strike buckles my knees but I quickly mange to get back in place.

At 15 he stops and explains, "you're going to take the last five directly on your asshole, hopefully it will be enough to stop this habitual tardiness of yours."

Stunned, I am unable to reply. The idea of having my asshole caned has never crossed my mind and I'm terrified.

"Reach your hands back and spread yourself wide for me."

I still don't reply but I do as I'm told and slowly reach back and spread my ass. His thumb runs over my asshole, "such a shame we have to bruise such a cute little hole."

I feel the cane slide between my cheeks and rest a moment before it pulls away and immediately strikes down hard. I jump and cry out before stuttering out a "one, S-sir." He shows no mercy and places his hand on the small of my back to hold me in place before striking again.

"Ahh...two Sir," I cry loudly.

He pauses a moment and leans down whispering in my ear, "shhh, don't make me gag you."

I try to calm myself, and taking a shaky breath, I nod in agreement. A second later the cane lands again. The sting is incredible but I managed to grit my teeth and keep from crying out. I take a few seconds to catch my breath and then count, "three Sir."

Again, searing pain, "four, Sir."

The last strike lands and I squeak out a weak "five Sir," before collapsing forward onto the bed, relieved that it over. But the relief is short lived.

"Now we still need to address your excessive masturbation, correct?"

In utter dismay, I fight back the tears. "Yes, Sir."

"Take your pants completely off and lay on your back," he commands. I roll over and watch as he opens his briefcase and pulls out a small jar. He holds it up in front of me and removes the lid. I stare nervously, unsure of what exactly it is or what he has planned. He moves closer and grabs my right hand. He dips my fingers in the jar, coating them thickly with a beige substance.

"Ginger paste," he explains.

My eyes go wide as I realize his intentions.

"Go on slut. You want to touch yourself so much, this is your chance."

I stare at my hand and bite my lip, before reluctantly reaching down and hesitantly placing my fingers on my clit. Slowly I begin to rub. Within seconds the burn sets in. It feels hot and cold at the same time and it's very unpleasant. He steps back and glances at his watch. "Five minutes. Keep going."

He sits in the chair, watching intently as I rub. My breath quickens and my eyes water, the burn seems to be increasing and it doesn't take long before I am begging to stop.

He doesn't dignify my pleas with a response, just looks at me sternly. So despite the burn I try to find some pleasure in the act and carry on. It's difficult, but thru the pain I manage to find some arousal. Although the pleasure is outweighed by the pain, and I manage to accomplish nothing except a slight distraction.

After five minutes I'm ordered to stop. He takes a soft damp cloth from his bag and gently wipes my pussy clean. The burn eases but doesn't completely go away.

"How's that asshole?" he asks.

"Tender Sir."

"Good. Stand up and bend over the bed. I'm going to fuck it now," he explains.

I watch as he slowly removes his clothes. His cock is stiff and glistening with precum. He lubes himself and then my asshole. Without any warm up or warning, he presses his cock against me and in one thrust buries it deep into my asshole.

I cry out at the sudden invasion but I've had plenty of practice and my ass acclimates quickly to his girth. However the caning has left my ring tender and every thrust is a painful reminder. His pace builds and every thrust seems harder than the last. My clit is still feeling the heat of the ginger and it burns.

Sirs hand runs up my neck and his fingers weave into my hair. He grips hard and pulls my head back to him. "You should be thankful I'm even fucking you, slut. Next time I'll bring in a more deserving woman and you'll get nothing but the pleasure of watching while I fuck her."

I don't have time to answer before my head is roughly pushed face first back down into the mattress. It doesn't take long for him to cum and when he does he thrusts in as far as he can and shoots his load deep into my ass.

He pulls out and orders me to my knees. I kneel and he steps forward quickly grasping my head and thrusting his cock into my mouth. "Clean up your mess," he orders.

Obediently I lick and suck while trying not to gag at the taste of my own ass.

"Good. Now I want you to climb onto the dresser and squat facing the mirror," he explains. "You are going to watch as you squeeze my cum out of your ass and onto the dresser. Then you will use your tongue to lap it up."

I stare up at him, silently pleading for him to spare me this humiliation. His face is stern and serious and with a tilt of he chin he declines my unspoken request. I hesitate a moment before accepting my fate and crawling to the dresser. I slowly climb on top and face the mirror. My reflection is pitiful, and I'm ashamed. My face full of tear streaks and smeared makeup and my hair is a wreck. Behind me his reflection is staring impatiently. It takes me a moment to get the nerve, but not wanting to upset him, I obscenely squeeze out his cum into the dresser. Turning around I lean down and stare at it, before slowly licking it up.

"Good girl. Now I think we could both use a shower."