Painful Pleasure Novels & Stories

“Pleasure and pain.” He brought the flogger down on my back, not hard, but a series of soft, stinging thuds that sent a warm, pleasant tingling through me. He continued, the strikes landing in a rhythmic pattern, warming my skin, sending me into a trance-like state. The pain was a dull, distant throb, overshadowed by a growing, all-encompassing pleasure. I was floating, adrift in a sea of sensation.

I wept from the wild mixture of pain, pleasure, and guilt, crying out that my godfather owned me. Leo reached his hand around my body and began to rub my swollen center very roughly while continuing to pound into me from behind. The intense combination of physical pain, deep pleasure, and crushing guilt pushed me over the edge incredibly fast. I hit a massive climax, my inner walls clenching violently around his length over and over again as I bit down on my lip to try to stay quiet. Leo followed me into the release just a few seconds later with a deep, low groan, burying himself as deep as he could possibly go and flooding me completely with his hot, thick seed. He stayed deep inside my bod

Each time his palm made contact with my ass, the plug inside me shifted, intensifying the pleasure and allowing the pain to blend into it. The remote of the plug was on a wooden table at the far end of the grey painted room, abandoned. Another slap. "Two. Thank you, sir." By the fifth I was squirming and trying to get away without even knowing. By the tenth I was visibly sobbing and when he pulled the plug out and shoved it back in, fucking me with it, I came with a loud, drawn out moan. "Did she just cum?" Chris mused, laughing. "The slut likes the pain."

"For… for pleasure." "Avalyn, I'll be fine. I've been with worse men." She smiled. But her smile wasn't sad. It was almost… confident. "Being hurt, being in pain doesn't bother me. Nor does hurting someone else and inflicting pain," she grinned. "I like pain. It helps me get off. In fact, it makes me horny," she said with a mischievous smile. "The best kind of pleasure is when it is mixed with pain. A little biting, choking, spanking." She laughed lightly when she saw that I had started blushing. "Well, all that is fun for me."

I take a deep breath and centre myself again, the point of this being to get to that point where pain and pleasure mix in a haze of ungroundedness. He lifts his hand again, the threat is more than enough and I cower to the extent possible in this position I so willingly placed myself in. The stings rain down, I can't tell if he's actually making contact, it's just the edge of his fingers whipping against the apple of my behind over and over and over, at some point I can't hold in my breath to stabilise the pain any longer and when I take a breath the pain comes rushing through me, the vicious tumbling of the waves of pleasure eating away at my resolve and I scream out as my pussy floods.

It was just that, at this moment, pain was much worse than the pleasure. He started thrusting slowly at first and when the pleasure started taking over the pain, he started moving fast. He grabbed my legs and wrapped them around his waist, before hitting me with a different angle. His mouth left mine and moved down to lick and suck at my nipples. Hard and fast. His hands held my waist in place, with his grip almost painful. My back arched up, as I threw my head back in the pillow and moaned loudly. The pleasure was too much. It was clouding my mind now. As he hit one specific spot repeatedly, rough and agressively, all of my senses started numbing.

They were like dried mold, molded into my belly that could never fly away. His mouth slowly took in my lower lips and I allowed him to do it. To take me deep in the pleasure that only he could give. To take my fears and pain away. To make me open my eyes after a long time. I don't know how long I had closed my eyes but I knew whatever the number of times it was, it was excruciating. Something about pain was that it didn't have time. Pleasure had time because it was euphoria. Pain doesn't. It feels like forever even after it ends. “I am here, Rebecca.” He called, molding my stomach once again with pleasure and I nodded before wrapping my hands around his waist. His beautiful scent came to my

he ordered again. “It’s pain,” she said, a catch in her voice. The crop left her ass where it rasped over sensitive, marked skin. “Too much?” There was worry in his voice. A promise that if she said the word, he’d stop. “No!” Her protest was immediate. A denial. She didn’t want him to stop. “It’s pain and then it’s pleasure,” she whispered. “Beautiful, exquisite pleasure. Like nothing I’ve ever felt. The pain is just pain. But the pleasure is indescribable. It makes me crave the pain because I know what will follow.”

It was a level of ecstasy I had never experienced before, a delicious blend of desire and fulfilment that left me craving more. As he filled me to the brim, I revelled in the intoxicating dance of pleasure and pain. The searing ache, a sweet reminder of our carnal union, slowly spread through my body, fanning the flames of our passionate encounter. Yet, my mind blissfully disregarded any discomfort, consumed by the intoxicating euphoria that engulfed me.

I have my long years of pain tolerance to thank for that. I reached the number ten and it never crossed my mind to use my safe word because truthfully, he was right. His pain was pleasuring me in ways I never felt before. My core was so wet, I almost felt it trickling between my thighs in that exposed position he had me in. Maybe it’s because my body was used to it. To the idea of deriving a relief out of physical pain, that I found myself enjoying it way more than I should considering it is supposed to be a ‘punishment’.