I Punish MaggiebyBoxlicker101©
When my telephone rang, it was the call I had been expecting. "Sir," came the quavering voice, "I have been very bad and I deserve to be punished."
"Maggie!” I thundered into the telephone. "How many times have I told you about that? Now I am going to come over there and whip your ass, and then punish you some more. You just wait until I get through with you, young lady. You’ll wish you had not been so bad!" After hanging up the phone, I got into my truck and drove over to Maggie's apartment. Maggie is 39 years old but she likes to pretend that she is a very bad girl and she gets me to punish her severely. Although the badness is just make-believe, there is nothing imaginary about the punishment she receives and that she would be receiving that day.
When I reached her apartment, she let me in the door and then stood before me, her head bowed in abject submission. Maggie is fairly tall, with long blonde hair and she has a really cute, round ass. "You dirty little cunt!” I yelled at her. "You are really in for it this time. I ought to kick your ass as hard as I can, slut-bitch. What do you think I should do to punish you?"
"Anything you want to, sir. I have been so bad that I deserve anything you want to do."
"You're damn, fucking right you have. Now, get your fucking cunt-ass into the bedroom while I figure out what I’m gonna do to you.” She turned and started into the bedroom. “Don’t you turn your back on me, bitch!” I bellowed at her. “Now, you just walk backward into the bedroom and take off all your clothes. I want it to really hurt when I whip you.” As usual, I was wearing a wide, leather belt and I pulled it off and slapped it against my hand. “I’m going to whip you with my belt, bitch. What do you think of that? Do you think it will hurt?”
“Yes sir. It will hurt terribly.”
“Do you think you deserve to be whipped by my belt?”
“Yes sir. I am such a bad, rotten cunt-bitch that I deserve anything you do to me. Please, sir, I should be severely whipped by your belt. I deserve it and it’s only right that I should be punished by you”
“Then punished you shall be. Now, go into the bedroom and take off all your clothes and bend over the chair. I’m going to whip your ass so hard it will take the skin off.”
A few minutes later, I followed Maggie into her bedroom. As I had ordered, she was naked and bending over the back of the heavy wooden chair with her feet next to the back legs. Two pairs of manacles, padded on the open half, were waiting, fastened to the chair legs above the rungs and I fastened one to each ankle. I walked around to the front of the chair and secured her wrists with the same kind of manacles that were fastened to the front rung, leaving her with very limited freedom of movement.
Once Maggie was manacled in this bent over position and her ass was sticking up in the air, ready for whipping, I grabbed her hair and yanked her head up so she was facing me. “Okay, bitch, are you ready for your punishment?”
“Yes sir, I am a very bad cunt-bitch and I deserve to be punished. Please, sir, whip me the way I deserve.”
Toying with her, the way we had agreed, I walked back behind her and smacked her naked ass with my open palm. “Did that hurt, bitch?”
“No sir. It didn’t hurt enough. I need to be hurt much more than that. Please, sir, whip me with your belt like I deserve.”
The next prop was a thick wooden ruler lying on the dresser. I picked it up and came back behind Maggie, who knew what was coming next, and was anticipating it. “Smack!” as hard as I could, I struck her other ass cheek. Maggie grunted from the sudden, sharp pain.
“Did that hurt, bitch?”
“Not enough, sir. I am so bad that I need to be punished much more than that. I need to be whipped with your belt, sir. Please whip me with your belt because I am such a bad slut-cunt-bitch that I deserve it.”
When I had entered the room, I had left the belt lying on the bed. Now I picked it up and held it in one hand and yanked Maggie’s head up by the hair again. “With this belt, slut?”
“Yes sir. Please whip me really hard with that belt, sir. I should be whipped as hard as you can with that belt.”
Back behind her again, I undressed myself so I was as naked as Maggie. Gently, I swung the belt so it slapped lightly against her ass.
“Please, sir. Whip me as hard as you can. Please whip my cunt-bitch ass, sir, the way my ass deserves.”
From what had happened so far and from what she knew was going to be happening, a trickle of juice was running from Maggie’s pussy and down her leg. I caught it with my fingers and licked it off. It was delicious. The time had come to get serious so I pulled back my right arm and swung the belt hard, hitting both of Maggie’s lovely white ass cheeks and leaving red welts on both of them. Although she had been expecting it, Maggie screamed with the searing pain that quickly turned to pleasure, and more juices flowed from her pussy.
“Did that hurt, bitch?”
“Yes, sir, but not enough. I need to be whipped many times and much harder because I am such a bad cunt-slut-bitch. Please keep whipping me, sir, because I deserve it.”
The first time I had spanked Maggie, it had been over my knee with my open palm, after verbal abuse. She had enjoyed that but after a while she needed more. I spanked her a few times with the ruler while she lay on the bed but then one day she noticed the wide, leather belt I was wearing with my blue jeans, and insisted I should use that. The first time I did, Maggie lay on the bed while I whipped her and she climaxed from that alone, as well as from the rather unconventional sex that followed. The second time I was to whip her with the belt, Maggie had provided the wooden chair and the manacles that we have been using since then and had placed them into the bedroom. The back of the chair was rather short so she could bend over at the waist, with her head hanging down and her ass presented for whipping. Even more important were the millwork knobs on the back of the chair, perfectly positioned so that Maggie could rub her clit on them, intensifying the orgasm that she gets from the extreme pain being inflicted on her.
Since then, this had been the routine: one spank with my hand, one with the ruler and then a whipping with my belt until Maggie reaches her first orgasm, followed by her cumming at least once from my eating her pussy and again from fucking. Although the second and third orgasms might sound ordinary, they are more closely connected to pain than what most people would consider pleasure. After we are completely through with the whipping and the sex, I apply the salve that she buys for that purpose. Maggie enjoys the whole routine immensely and, although I am not really into inflicting severe punishment like what Maggie gets off on, I always do what my lady friends want.
Between the time of the first lash with my belt and the second, about four seconds passed. We both believe it is best to let a few seconds pass so that the pain of the first stroke will have evolved into pleasure before the pain of the second is inflicted on her. Maggie screamed again the second time I hit her, and I was glad of the thick walls and the double paned windows that muffled the sounds. The crack of my belt against her bare skin and the screams it elicited would surely have resulted in complaints from neighbors if they had been able to hear them. The second welt crossed the first and the third lash, which was harder and resulted in an even louder scream from Maggie’s lips, was parallel with the second.
After that, I waled her with the belt over and over, making her scream every time and always waiting a few seconds between blows. Between her screams of pain, she started moaning and I recognized the moans as being of sexual pleasure because Maggie truly loves being whipped the way I was whipping her. Besides moaning, she seemed to be dancing, as well as she could with her ankles manacled, from the pleasure of the severe flogging and I could see and smell the delightful juices trickling from her pussy as Maggie became more and more aroused. The dancing, besides being an expression of pleasure, about the same as a woman thrashing on the bed while her pussy is being eaten, helped Maggie grind her clit against the millwork knobs on the back of the chair, bringing her closer to ecstasy with every movement.
As Maggie moved closer to cumming, I waited longer between lashes with my belt. Although the whipping would continue, even while she was cumming, once she had reached her orgasm, it would stop. Usually I whipped her across her cute, round ass but frequently my belt struck the upper parts of Maggie’s thighs. This was deliberate, not a miss, because Maggie wanted the backs of her thighs to hurt just as much as her ass. Most of my blows were forehanded but sometimes I would move to my right and hit her with a backhand slash so I could inflict the pleasurable pain she wanted on the side of her left buttock. Maggie insisted I should turn her entire ass into a scarlet mass of pain and I would always do my best to do what she wanted.
I’m cumming, sir,” Maggie blurted out and her dance became more frenzied, her legs moving faster and her clit slamming harder into the back of the chair. My movements became more frenzied too, whipping her faster and harder because I knew that while she was cumming, Maggie wanted her agony to be intensified. Finally, her entire body gave a great spasm and she sagged over the back of the chair. I stopped, knowing Maggie had climaxed and her whipping was over. Not wanting to waste any of the more delicious things of life, I knelt behind Maggie and licked up the juices streaming from her pussy. As I licked her legs, my hands were on her ass and I could feel heat emanating from where I had been whipping her. After I had relished her juices, I waited while Maggie regained her strength from her tremendous orgasm so I could unlock her manacles.
“I’m ready, George. You can release me.” Once Maggie had cum from being whipped that part was over and she was no longer subservient, which was actually my preference. After unlocking her manacles, I helped her to lie down on her back, her legs spread for the next part of our peculiar love-making.
“My ass is so sore I can hardly walk. You really whipped my ass today and got me to cum bigtime.” The pain she was feeling would last for a few days and the welts would be there longer. Memories of the pleasure she had from being whipped and climaxing would last much longer.
Although the whipping was over, the agony it had caused was still part of our love-making. Maggie lifted her bright red ass off the bed while I slipped a pillow underneath her. When I brushed the pillow against her skin, she grimaced from the sudden burst of pain radiating from the point of contact. With the pillow in place Maggie raised her legs, still spread wide, for me. I wrapped my arms loosely around her legs, and when my face was positioned above her pussy, I squeezed her, roughly pressing my shoulders against the backs of her thighs, which had just been thoroughly whipped, and were as much a mass of scarlet pain as her ass. Maggie screamed from the sudden, intense pain; pussy juices squirted into my waiting mouth and her pussy fucked into my face.
Usually when I eat a pussy, I start with the lips and lick slowly until the woman cums but with Maggie, after a whipping, I hold her thighs and lick her clit from the start and, about every four seconds, I squeeze, sending waves of agony screaming throughout her body, evolving quickly into pleasure, because the combined pleasure of my tongue on her clit and the intense hurt from her abused thighs is what it takes for Maggie to cum.
Her pussy kept fucking into my face and her body went from squirming to writhing to thrashing on the bed as I continued with the licking and squeezing combination for a long time. Her screams continued to be incoherent expressions of suffering until one of them was actually an announcement that Maggie was starting to cum. When I heard that, I squeezed tightly and locked my mouth on her clit, sucking her engorged love toy and caressing the side with my tongue.
Maggie’s involuntary movements during the throes of cumming, especially of her legs, sent more waves of agony through her body as her thighs rubbed against my shoulders. More and more, Maggie thrashed on the bed as her pain and pleasure continued until she climaxed, arching her back and giving a sudden jerk of her legs. I released her then, and Maggie collapsed on the bed, agonized tears coursing down her cheeks and a wide smile of pleasure on her face.
She lay there for a few minutes before getting up and hobbling painfully over to me and fondling my cock. “Did you bring condoms?” she asked. It wasn’t really a question, just a reminder of what was next on her pain/pleasure agenda because she knows that even if I had forgotten, she had some available. My pants were lying on the bed and I got a condom out of the pocket and handed it to her.
Grimacing with pain, Maggie got to her knees and took my cock in her mouth. She stroked it in and out a few times, enough to get it fully erect and wet enough for the condom to slide on easily. With my cock ready, Maggie crept over to the chair where she had been whipped and rested her upper body on the seat, smiling at me over her shoulder. I knelt directly behind her.
Usually I am very gentle when I insert my cock into a woman but when I reached out to open Maggie’s pussy lips, my hands squeezed her ass while my thumbs opened her, and I could actually feel heat radiating from where she had been whipped and I could almost feel the pain.
Maggie could definitely feel the pain and a scream came from her lips, followed by a burst of juices in her pussy. My cock slipped in easily and, several thrusts later, I was almost all the way inside. This meant that my legs and hips were just an inch from Maggie’s severely whipped ass and thighs. With my hands on the fronts of her hips, I backed my cock out and thrust forward, driving my cock all the way into Maggie’s pussy and crashing against her scarlet mass of pain.
She screamed, of course, seemingly trying to turn her throat inside out, and I stayed where I was, my body plastered against Maggie’s most painful areas, able to sense the heat radiating from her. While I rubbed against her, I moved my cock inside her, feeling the heavy flow of her lubricating pussy. Maggie’s body writhed against me, and that contact added to the pleasure/pain she was receiving. I knew the combination of my cock deep in her pussy and the agony she was feeling in her ass and thighs would cause her to cum before very long so I reached around and caressed above and around her clit, and then directly on her love button. Her pussy received gentle treatment from me but for the rest of her, I was the major source of the excruciating pain that was sweeping through her body.
Maggie started cumming and I did not let up on my abuse of her ass and her legs but my hand continued to gently caress her clit. For several minutes, I intensified my efforts until I felt her back arch and her pussy thrust against my hand on her clit. She had cum quickly from the agony, and I still had a while to go so I continued fucking her pussy. However, I kept my hands on her hips, far from the abused areas and I avoided rubbing against her. I had already inflicted enough pain on her; I didn’t want to do any more, since it would not result in any pleasure for her. After a few strokes, I ejaculated and a minute later, gently pulled my cock from Maggie’s pussy, avoiding the red skin of her ass or thighs.
When she was ready, I helped Maggie to her feet and over to her bed to lie face down, her ass as red as a beacon. I slathered on the salve, which Maggie swears is the best there is, coating her ass and the backs of her thighs and rubbing it in as gently as I could. When I was through, I washed the excess medication from my hands, got dressed and kissed Maggie goodbye. When I left, I locked the door after myself. Eventually, the pain will dissipate and the welts will heal and a few weeks later, I will get another call from Maggie, telling me how bad she has been.
Thank you for reading this story. I hope you enjoyed it even though it is not my usual type of story. Mostly, I write about gently making love with a series of women. If you liked this one, let me know. Vote and leave a public comment (PC) or email me with your comments.