I firmly believe that only good boys should get spankings. Spankings are so delicious, full of ripe, reddening ass flesh, cries for mercy, and a firm, tantalizing hand—I believe that in a perfect world, they would be bestowed upon only the most worthy, best-behaved, and most grateful of submissives. But we don’t live in a perfect world, as I’m sure you know. This is the story of a boy who thought he could have the last word with Mistress Fiona.
In many respects, it was a typical Thursday night in Manhattan, just outside of Chinatown. The streets and storefronts were quiet, a fitting backdrop to the muffled sounds emanating from the loft where the Gag Ball was in progress. Both the loft and its visitors were visually striking that evening. The thousands of square feet of open floor space had been split into six areas by four enormous moveable walls of welded metals. The only windows, draped with red velvet to protect the delicate constitutions of passersby, were at either end of the long, thick middle corridor that stretched between the play areas, three areas on each side.
In keeping with the theme of the night’s event, most every sub, slave, boy, and girl in the place were dragged and gagged—that is, they were cross-dressed to some degree and outfitted with a mouth gag. It was a glorious sight, of great diversity as well as creativity on the part of the clever Dominants who had dressed their playthings. Girls with great bulges in their chaps and boys wearing bustiers atop their crinolines milled about silently, self-consciously, demurely. The assortment of gags was impressive, and each gag suited the costume of its wearer; some gags even matched the attire of the Dominants whose property—watched over by dark, dominant eyes—bore them between tender lips and in gaped jaws. There were neon-bright ball gags for the twinks, and penis-shaped gags for the cock whores, bridles for the pony boys, even Whitehead gags for the medical experiments who shivered and whimpered atop the medical tables, legs spread wide and accessed by gloved fingers.
Boys would drool uncontrollably due to the large objects forcing their jaws open, and their Masters and Mistresses would beat them soundly for the transgression. Girls would dab at their chins demurely with appropriately colored bandanas, black ones for heavy Sadomasochism, red ones for fisting. The near-silence was magical. Even during the cruelest torments, the gags prevented the cries of the wickedly mistreated from reaching a crescendo. There was, instead, a punctuated sort of humming, low and high and intermittent from their throats, echoing off the walls and blending perfectly with the sounds of Dommes threatening, implements moving through the air, and the rain tatting against the metal roof above.
I lounged in the middle of this glorious spectacle on a red leather divan, resting my limbs after administering quite a heavy beating. The cool glass felt wonderful against my hand as I sipped my Cosmopolitan and stretched my leather-clad calves. In front of me hung the boy I had chained to a Saint Andrew’s cross for a sound torture and ass fucking. He was naked except for the subtle blood trails on his chest where the needles had been, and the inflatable gag I so loved to pump the handle of. His breathing was deep and his eyes were closed, but his cock, bless his little heart, was standing straight up. As the sight of him and the taste of the cocktail revived me, I observed how much like art he was, a perverted hybrid of performance and permanent installation.
As I turned my head to look through the rogues’ gallery at the other members of tonight’s exhibit, I noticed another Domina walking through the main corridor. She wore a black wrap around her shoulders that barely covered her ample, corseted breasts, and she led a naked boy on the end of a chain leash. Her face was troubled, and she seemed to be looking for something—or someone. I motioned for a nearby girl to come help me sit upright, and soon my black-and-red organza skirt flowed down over my high boots, almost to the floor. When I arose, I caught the Domina’s eye, and she walked toward me as I nodded slowly in greeting. “I felt some concern about your demeanor, Sister. Is there something wrong?”
She frowned and replied, “My firm called to tell me that the contracts have finally arrived, which is great news. But I can’t call my driver until I have someone I can leave him with. Most of my friends are here.” She pointed to several imposing women elsewhere in the loft, who were decadently engaged.
Hearing that another powerful female was in need of assistance, I immediately offered to watch her slave boy. It was with no small amount of relief that she sighed, smiled, and gave me the handle of her leash. Our black leather gloves matched, and when we noticed this, we smiled privately to one another. She turned around and made her very caring goodbyes to the boy. As she spoke to her boy, I looked over at my boy, still in a dreamlike state on the cross. I could look after them both—after all, one boy was tied up at the moment and the other was on a leash. How much trouble could that be?
Just before she walked away, she removed his gag and kissed him very hard on the mouth. “Behave,” she intoned before she disappeared from sight. His mouth hung open like a dog’s as he watched her leave. For a moment, I empathized with him, separated from his Mistress, his owner, his heart breaking. I thought that perhaps after I’d petted his head for a little while, he’d feel better, and I would send him for pillows and beverages and keep him otherwise occupied until his Mistress returned. I handed him my glass and addressed him kindly but firmly, “Come over here and sit by my feet.” His eyes turned to the floor, and his forehead wrinkled up. “I don’t want to.” In turn, my eyebrows raised, and I said coolly, “I will not remind you again that I am acting in your Mistress’s stead right now, and that you are not behaving in a way that either of us approves of.” Anger flooded his face as he turned to me and cried, “You’re not my Mistress! I want my Mistress.” He threw the glass to the floor, the loudest sound of the evening. My boy’s head came up in alarm, and he watched the scenario unfolding before him while struggling against his bonds. Immediately, my grip tightened around the leash as I wound it around and around my hand, forcing him to come toward me. His anger mingled with fear now as his face inched closer and closer to mine. I kept the corners of my mouth from turning up in derision at his childish action, and when he was right in front of me, quivering with emotion, I kissed him hard and savagely. He made a noise of shock and alarm, struggling to break free, then becoming completely ensnared by my delicious mouth, his cock springing to life inches from me.
We can’t have that.
I broke the savage kiss that smeared my lipstick all over his mouth. I laughed as I pointed this out, and his face reddened in shame. “And shamed you should be,” I told him, “because shame is what you have brought your beloved Mistress tonight, you selfish thing.” He opened his mouth to speak, but my free hand swung back as if to slap him across the face and he closed it again in a hurry. “You brought shame to her, and great disrespect to me. I do not suffer fools, boy.” I dropped the leash’s slack and pulled hard, making him trip as I walked to the broom closet. “Come with me and begin redeeming your atrocious behavior.”
The walk to the closet was interminable because I could hear him begin snippets of sentences—apologies, explanations, and justifications. Each time, I told him to hold his tongue or it would be held for him. Finally, I threw the closet door open. “Fetch that dustpan and that cardboard box. You’re going to clean up that mess you made.” When he also reached for the hand broom, I yanked his chain. “No. You won’t be needing that.” There was fear and hatred and desire mixed up on his face and in his little body when he turned back around. I could not help but laugh in his face. “Don’t look at me again. You got that?” His eyes went down, and his cock aimed higher and again we walked to the middle of the corridor where liquor-soaked shards of glass were scattered across the floor. On the way, I loosened my boy from his bonds, and motioned for him to follow us.
“Put the box and the dustpan down right there,” I pointed. He did it so slowly that I had to put my boot between his shoulder blades and push. “And where did you shame me, boy?” He seemed startled by my question. “I—I don’t
Horror spread across the boy’s face. My own boy’s face filled with admiration and love, and his cock grew even harder. I nudged my steel-toed boot in between the bad boy’s ass cheeks, and with a cry, he fell forward onto his hands. “Be quick about it,” I said. I could see the tears falling from the boy’s eyes as he mouthed each chunk of glass and spat it back out again into the dustpan. Over and over, he collected individual pieces as gently as possible, crawled on his hands and knees to where my boy held the dustpan, and spit the jagged glass into the pile. As gingerly as he tried to do this, I could see some pink dripping from his lips and staining the broken glass in the dustpan. I knew the drink I had not quite finished that clung to the pieces would thin out his blood a little, making him bleed more, and I smiled.
When the last piece was collected, I instructed him to finish by swabbing the floor clean. As he licked the floor, dirt and tiny glass shards sticking to his red tongue, I could see his cock starting to drip precum. He was enjoying himself immensely, even while he despised this. At the very end, I instructed my boy to empty the dustpan into the cardboard box and dispose of it, and I pulled the bad boy to his feet.
I did not have to pull him toward the bathroom, our destination. He walked behind me docilely, causing me to understand a little of why his Mistress would find pleasure in him in the first place. I first made him rinse his mouth out thoroughly so no glass or dirt remained, and then I made him gargle with a solution of peroxide and Listerine. When I was satisfied that his wounds were addressed adequately, I bent him over the sink so his ass stuck out, exposing his tight little anus. I ran water into the sink until it reached a sufficient temperature, and then I filled a red rubber bag and hung it from a steel pole. The boy whimpered a little when he saw me lubing up the oversized hose tip. “This will make you clean again,” I said as I pushed the thick plastic tip into his hole. He cried out, and as I released the clamp so the warm water could force itself into him, I said, “I can’t wait to gag you again, boy. Oh, it’s going to be great to have you quiet and obedient at last.” Finally, the red bag was flat, and I removed the tube from his ass. In a moment, he was slowly moving his hips and breathing hard as the enema water warmed and filled his insides. When my boy approached the bathroom with my toy bag, I was pleased with him and told him he could sit on the bathroom floor and masturbate.
The bad boy was enjoying the sensations of the water but was starting to get antsy. I smiled because I knew it would be a long time before he would feel anything but tension in his guts. Behind him, I was smearing lube all over a large, black rubber ass plug. From the floor, my boy’s eyes lit up, and when he jerked his large, meaty cock, the pump on his inflatable gag bounced. When I could see the boy squirming with discomfort, straining to keep from having an accident on the floor, I swiftly twisted the black plug into his asshole. The bad boy stuck a knuckle into his mouth and stifled as much of his moan as he possibly could. I hopped up on the sink next to him, grabbed him around his waist, and started to spank him very soundly. I hit with both hands, being sure to smack the ass plug regularly. I knew that the vibrations from the spanking were combining with the explosive feeling of all that water, and with the ass plug ruthlessly in place, there was nowhere for his emotions to go but into his cock, which burst into an orgasm that left him sobbing. Soon after he came, my boy let loose a giant load of cum that reached up onto the bad boy’s ass and thighs. My boy took the gag out of his mouth to clean the bad boy up with his tongue and then replaced the gag. He’s such a good boy.
At last, I pulled the bad boy off the sink. He melted into my arms. “Do you think you can behave now?” I asked. “Oh yes, Mistress” was all he could manage. Satisfied, I positioned him over the toilet, bent over as far as he could go. Then, I worked the large plug out of his ass with an audible pop. The liquid flowed out of his ass in a great rush, and he moaned loudly and came again with relief. I let go of him and he rolled forward onto the floor. He looked so lovely down there next to my pretty boots.
He collapsed onto his stomach, shaking and sweating. “Roll over,” I commanded as I swatted his ass, “and open your mouth.” Although exhausted and broken, he complied immediately, and I pushed the ass plug into his mouth. It was a perfect fit. “You are responsible for keeping your new gag in your mouth, brat. It was one of my favorites, but I certainly don’t want to possess anything that’s been in your filthy, bratty body. I shall send you the bill shortly, after I’ve spoken to your Mistress about what a fitting quantity and type of restitution would be.” He looked up at me and blinked, not daring to nod, his eyes full of remorseful tears. I knew this spanking had not been wasted, even if it did have to be delivered to such a bad boy.
When his Mistress returned, she was appalled to hear about the misbehavior of her slave. But she was also very grateful for the appropriateness of the punishments that I exacted in her stead. She punished her boy further, and had him make restitution in service to me for some time. She and I have remained friends to this day.