Punishment

"You have been quite the tease," Ben states bluntly as I enter the hotel room.

"I thought you enjoyed me being sassy." I retort with a wink as I lean in for a kiss.

"Oh I do," Ben murmurs as he threads his hand through my hair and pulls me in for a scorching kiss, rubbing his whole body against mine. Ben growls, his hand tightening in my hair, while the other pulls my arm behind my back in a deadlock, pinning me in place. "But failing to respond to my messages and rescheduling on me twice is more than just being sassy." Ben kisses me again, roughly, forcing me to bend back over my own arm, throwing me off balance.

"And now you will be punished appropriately." Ben forces me to walk over to the bed, then bends me over the edge with my ass in the air. My dress rides up, exposing my soft skin to his rough jeans as he leans over me. Releasing my arm, he strokes his hand down my side to my hip, using it as an anchor to grind his cock into the crack of my ass. "Pick three numbers between one and ten," Ben commands, still grinding into me.

"Why?" I ask. Ben's fingers tighten on my neck, sending chills up my spine from the slight pain. It is a clear indication of his dominance over me. I whimper as a hard swat lands on my backside, enforcing that he will not stand to be questioned, or forced to repeat himself tonight.

"Three, five, and seven." I gasp out.

"Is that the order you choose?" Ben doesn't release his grip. "The order is also important."

"Yes," I breathe.

"Good. Because those are the implements that'll be forced up your ass tonight as your punishment. And you only get lube for the last one." I whimper quietly as he lifts a towel off the bed that I hadn't previously noticed. Hidden underneath is an array of toys, most of them larger than what we have used before. It has been several months since Ben chose to use my ass at all, and seeing the toys before me, I know this lesson is intended to be one I will never forget.

"You're a lucky girl." Ben holds the written list before my eyes and I cannot help but agree. Number three on the list is 'fingers', which I hope will be a much easier primer than any of the other toys in front of me. Number five on the list is a medium size plug of those on display, but this is also the largest plug that we have previously used. Made of unyielding glass, three inches long and nearly two inches in diameter, it will be an uncomfortable stretch to take without any lubrication. My fate could have been much worse, compared to some of the other toys before me, however. My gaze strays to a large, ribbed plug that is easily five inches long and four inches in diameter at the base, which I note is labeled number six. I shudder. Number seven is a rubber dido that can be attached near the base of a cock. At six inches long, with two-inch-wide beads spaced along its length, it's really a cross between a dildo and anal beads. I'm grateful I'll be allowed lubrication for that monster.

Ben runs his hands over my ass, kneading the flesh between his fingers, hiking up my dress so that my panties are completely exposed. Using his knee, Ben forces my legs apart, still keeping my head pinned to the bed. My feet are spread wide enough on the floor that he has easy access to both my pussy and my ass.

"Let's warm you up a little before your punishment begins." Ben's hand roughly kneads my ass through my thin panties. "Keep your legs spread and that ass up in the air. If your feet move from where I have placed them, you will be spanked directly on that tight little asshole of yours."

I moan, knowing that he will follow through on this threat and that Ben's idea of a warm-up means he's about to spank me until my ass is rosy red and positively radiating heat. The likelihood of making it through my spanking without moving my feet is small to none. I'm definitely in for it this evening.

"Stay," Ben commands, as I feel him stand up, the pressure leaving the back of my neck. I hear him grab something from a bag, a rasping, crinkling sound. Ben kneels down on the floor behind me. "I am placing pieces of tape on the floor so that I will know if your feet move so much as a millimeter."

Now I KNOW that I am in serious trouble; there will be no room for any of my usual bratty behavior tonight. No faking compliance. Ben's nails trace up the backs of my thighs, hard enough that there must be faint lines left in their wake.

The first smack hits the right cheek of my ass before I expect it and I yelp in surprise and a little bit of pain. "Come on now, pretty girl, you're going to have to take much harder hits than that tonight," Ben warns me as he delivers another stinging slap to the left cheek.

I groan and grip the sheets underneath my fingers as the spanking begins in earnest. Alternating between stinging slaps and hard blows that I feel all the way into my seat bones, there is not an inch of flesh on my ass left untouched. At random intervals, Ben smacks and gooses my pussy, driving my underwear up into my body, forcing it into the crack of my ass, exposing my skin directly to the bite of his hand.

As the spanking proceeds, I moan and writhe, trying in vain to escape the blows that are getting steadily stronger. I freeze as I feel Ben's hand rest gently on my ass, grinding my underwear against my asshole, ensuring that there is absolutely no lubrication of any kind left to ease my upcoming punishment.

"Let's see how you're doing, pretty girl." Ben runs his fingernails over my tender ass. I bite my lip, trying to contain a groan of pain.

"Your ass is coming along nicely but isn't nearly warm enough yet. Have you moved your feet?"

I shake my head in the negative, praying that my wiggling hasn't been enough to cause them to move from the markers he'd placed.

"Why don't I check?" Ben murmurs as he scratches down my ass to the backs of my thighs, causing me to gasp, trying desperately not to move.

"Tisk, tisk, they've definitely moved! For that, you will receive five hits directly on your asshole when I'm finished coloring your pretty ass. I'm going to move your feet back to where they should be. If they move again, I will add another ten." First one foot, then the other, are dragged back to their tape markings.

Ben's hand returns to the back of my neck as he begins spanking me again, pinning me to the bed as I try not to move with each hard whack to my ass. He begins to alter not only the severity but also the timing of each hit to my reddening cheeks, leaving me twitching, trying to anticipate when and where the next blow will land. I am whimpering as each strike lands, my tender ass now a glowing shade of red if previous punishments are anything to go by. The final three strikes somehow manage to radiate all the way up my spine. Rough jeans scrape against my tender ass as Ben leans down to see whether my feet have moved. I close my eyes, dread seeping through me. I know the final strikes caused my feet to move just from the sheer force of the blows.

"Looks like you will have a total of fifteen strikes on that tight little asshole of yours pretty girl."

I whimper, knowing that this will make my asshole far more tender for the upcoming punishment. I feel Ben move away from the bed; I crane my neck to try to see what he is doing.

"Don't move!"

I freeze instantly, my sore ass more than enough of a reminder to behave myself.

Ben slowly pulls my panties down over my stinging ass and has me step out of them, placing my feet back into their wide stance. The cool air of the room soothes the stinging skin of my ass. "Use your hands to spread those butt cheeks wide pretty girl."

I reach back quickly to comply, not wanting to increase my punishment any further. I grimace in pain as my hands gingerly peel back the sore globes, baring my asshole to his scrutiny. Without warning, I feel a sharp smack against my tender backdoor. I let out a yelp, realizing that this punishment will not be delivered with your hand, but a far crueler implement.

"Do you know I was able to find these at the dollar store?" Ben waves the wooden ruler in front of my eyes. "I was able to buy a whole pack so that even if I break one punishing your naughty ass, I can still continue your punishment until I am satisfied."

Three cruel strikes land directly on my tender asshole in rapid succession. I cannot help but cry out. As the next series of blows land, I struggle to remain still and keep my asshole vulnerable to the exacting strikes. Without being told, I know the punishment would be severe if I were to try to escape the cruel blows raining on my most sensitive opening.

"Last three, pretty girl" Ben tells me. "Stay perfectly still".

I brace myself, knowing that they will be the hardest blows yet, even though I already have tears in my eyes from the burning sensation radiating from my tenderized hole. I squeal as each blow lands. Ben keeps the ruler connected to my sore anus after each hit, ensuring the maximum possible sting.

After the last swat, Ben trails the sharp corner of the ruler around the ring of my ass. I cry out as the corner of the ruler is pushed against my enflamed asshole, feeling the splintered edge digging in ever so slightly to my swollen entrance.

"Now your ass will be extra tight for your punishment" Ben hisses in my ear, gloating.

I hear him place the ruler on the bedside table and know that the time for my true punishment has arrived. Ben leans over me, grinding his cock into my aching ass, teeth biting deeply where my neck and shoulder meet. I groan in pain and arousal, feeling my pussy begin to drip, despite the pain emanating from my already abused hole.

"I know you thought that my fingers would be a forgiving introduction to your punishment. You probably thought that it would be similar to our normal warm-up when I chose to play with your delectable ass. But you have been a dreadful tease... and I want this to be a punishment you never forget" Ben whispers as he shoves two dry fingers into my unprepared ass.

I gasp, back arching, my head coming off the bed as I try to escape his fingers as they burrow into my dry asshole. Ben grabs my neck, forcing me back to the bed as his fingers twist and burrow into my rear opening. Without lubrication, I can feel each ridge in his knuckles as they pass my sphincter.

While I would normally be able to take two fingers easily, the direct spanking with the ruler has left my asshole swollen tight. Now I am moaning in discomfort as I feel them work to stretch out my unwilling hole. Ben roughly saws his fingers in and out, knuckles banging against my sphincter with each thrust. Before I've fully adjusted to two, a third finger is added. My breath huffs out, all of my attention focused on the stretching of my ass around his demanding fingers.

Suddenly the fingers are ripped out of my ass. Ben forces his thumb into my anus as far as it will go. Gripping my anal tract from the inside, he slowly pulls up, forcing my asshole to open. I shudder in pain, mumbling and gasping incoherently, knowing that no amount of begging will get me out of this punishment.

"Do you feel how tightly your tiny hole is still gripping onto my finger?" Ben taunts me. "Imagine how much more it's going to have to stretch to take that plug!"

I can only groan in response.

"I think it's time." Before I can take a breath to steady myself. I feel the cold glass of the plug against my anus as Ben holds it right at my entrance, teasing me, pushing just the tip into my tight anus. Slowly, he forces the dry plug into my resisting ass, alongside his thumb until it rests at the widest point.

"How does that feel, pretty girl?" I can hear Ben's excitement. I know he loves stretching my asshole, that the sight of my anus stretched around the plug will have his hard cock pulsing with the desire to be buried deep inside me.

"It hurts." I moan as my ass clenches involuntarily on the cold, unyielding glass. Ben removes his thumb and twists the plug inside me, forcing me to feel every imperfection and bump in the glass as my asshole remains expanded over two inches. Then, slowly the plug is fucked in and out of my ass. The lack of lubrication means that the plug does not slide smoothly, but the tender skin of my anus is pulled and pushed, twisted, and pinched with each thrust of the toy. Finally, he allows the plug to fully seat itself in my ass. I feel full and stretched, as though this plug is larger than any I have taken before, even though I know that I have worn it many times. I take a deep breath, trying to will my anal tract to unclench. I feel a sharp tap on the end of the plug.

"Are you ready for the third stage of your punishment, pretty girl?"

I nod, hoping that the lubrication promised earlier will ease the burning sensation of my tender asshole.

Ben jerks the plug to its widest point, causing me to huff in pain. With a final twist, the plug is fully removed. I hear footsteps wander across the room. The burn radiating from my dry, abused hole contrasts sharply with my dripping snatch. A cold, firm point is dragged up my inner thigh. It must be the head of the dildo. While narrower than the plug, the variations in size will force my already exhausted sphincter to expand and contract rapidly. Since there will be lube, I know Ben won't have any reason to hold back as he reams my ass. I whimper as he drags the head through my wet slit.

"It's an awfully good thing you've produced plenty of lube... you're going to need it!" Ben drives the dildo into my sopping cunt, bottoming it against my cervix in one thrust. The heel of his hand spacks onto my tender asshole. I scream and nearly cum, overwhelmed by the pain of my ass and the pleasure of my pussy. The dildo continues to thrust inside me as I shudder and moan, never fully able to reach orgasm. Before I fully adjust to the rhythm and depth, Ben wrenches the dildo out and places it against my swollen nether hole.

"Why are you being punished, pretty girl?"

"Because I didn't return your calls and kept rescheduling." I choke out, hands still holding my tender ass cheeks, keeping my hole exposed for the final reaming.

"Good girl." With that, the first two beads of the dildo are forced into my resisting ass. Another scream is wrenched from me, far more from pain than pleasure. Two more beads are shoved in; each one feels like a bowling ball. Strings of arousal are sliding down my inner thighs.

I am so overloaded; I see stars. Then, the entire dildo is buried in my ass. My eyes are clenched shut, I'm entirely focused on the agony radiating from my ravaged ass. Each time my ass is forced to open and close over one of the balls, I see flashes of light behind my eyelids. It hurts but I want, no, I need more. I need a release from the tension coiling inside me.

"Please!" I gasp as Ben rotates the toy inside me.

"Please what, pretty girl?"

"Please, I need to cum!" The whole dildo is yanked from my ass, it seems to take all the air in my lungs with it.

"No."

I cry out in anguish as he forces the dildo back in, sawing it back and forth, changing the depth of each stroke. Pain transmutes to pleasure, pleasure without release circling back into pain. It feels like the ravaging of my ass goes on for hours, but it's likely been fifteen minutes at most. My cries have turned to grunts and moans, even though the pain hasn't abated at all. Ben knows how to fuck me to maximize whatever sensation he wants, without letting me grow accustomed to it.

Ben fully bottoms out the dildo in my ass again, using my neck as a handle to push me back onto his thrust. I can feel my pussy juice trickling down past my knees. I love how Ben isn't afraid to torture me. He knows how much I crave feeling controlled, dominated, forced to submit to his every whim.

"Fuck! I love getting to abuse your little hole!"

I feel fingers drag even more moisture out of my cunt, exposing the extent of my deprivation. "You love it too, you little anal slut. Say it! Tell me how much you love letting me fuck you raw. Tell me and I'll let you cum!"

"I love it! I love how you.. ah! God! Yes! My ass is yours! Please! I just... anything, you can do anything!" I'm rambling, I'm incoherent, I'm spewing words as Ben pumps the dildo furiously into my ass, hoping to find the right ones so that he'll let me cum. "I love when you use me... used your pleasure! I need... please! Ah!"

I must have said something right, Ben's cock slams into my pussy, rubbing against the dildo through the thin membrane separating it from my anal tract.

"Ahhh!" My inner muscles spasm around his cock and the dildo, sending shockwaves up to my brain.

"That's it pretty girl, take it all," Ben commands as he begins pumping furiously, his cockhead rubbing against the beads.

"Please, please, please," I chant, not even sure if he can hear me. I'm so close, but the pain keeps me from tipping over. Ben thrusts both his tools to the hilt. I gasp. Grinding deep inside me, the sustained pressure finally tips me over the edge and I fall into rapture.

I groggily blink my way back to reality. I'm laying on my side on the bed. I can feel Ben's spunk slowly oozing out of my slick pussy. The man himself is warm against my back, curled protectively around me.

"So you're always going to call me back from now, right pretty girl?"

I nod wearily.

"And you aren't going to reschedule on me anymore are you?"

I bite my lip. "Well, maybe every once in a while."

Ben laughs as I cuddle back into him and drift off to sleep.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Thank you for reading! Comments, critiques, and suggestions are appreciated!

This story will continue in a future instillation titled "Aftermath"