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.
