He could see the change overcoming her, her body now easily aroused, even after the whipping he had subjected her to. He found that happened in some cases, especially with virgins. They didn’t have the experiences to associate with in the past so even pain, as long as pleasure followed would excite them as if that is how everyone received the pleasure. She seemed to be in a daydream, his fingers pulling on her labia, yanking a bunch of pubic hairs out bringing her quickly back to reality.
“Yellllp,” a sprig of dense hair pulled from her bush bringing back the reality of the pain. His finger slipped between her lips, his powerful hand gripping her sex tightly, squeezing the flesh, forcing her ass to arch up. “MMMM,” she moaned in pleasure and pain as her anal ring was forced wide by the thick finger, burning as it stretched wider to engulf his thick knuckle. It felt like a foot of finger was inside her, moving around as if it was a bug, discerning as it seemed to hurt and tickle her insides all at the same time. The finger massaged her rectum, rubbing back and forth over the muscles as she tried to control the unnatural spasms of her muscles, tightening up on the finger as she fought the urge to have a bowel movement, afraid of having an accident.
“Such a nice, hot tight hole you have Princess. And such a grip.” He squeezed her pussy hard, forcing her ass up higher. “Take more of my finger in your ass.” He felt the rhythmic clenching of her muscles. “Yes, it feels so good when you tighten up on my finger.” His cock throbbed with desire, the thought of her asshole masturbating his cock with her clenching muscles excited him. “You’ll do well when I sodomize you Princess. Your asshole will bring me much pleasure.”
His finger slide farther inside her, his knuckles finally banging up against her anus, a strange tingling as he hit her anus with a thud that tingled the tiny pleasure sensors that ringed her sensitive hole. How could she feel pleasure from such a despicable and degrading act? The finger began to withdraw, the oil beginning to burn as he dragged his finger from her ass, her anal ring clinging tightly to the thick digit. She could only tighten her hole as her ass burned, clinging to the finger as if she didn’t want it to leave, the tip of his finger bending inside her, stretching her wide as it did.
The pirate removed his hand from underneath her, her ass remaining raised up in offering, his finger now beginning a gentle fucking of her tight, virgin asshole. He could feel her muscles responding to the internal probing, clenching on the invading finger, feeling as if she was trying to pull it deep inside her. Not to dissuade her, he plunged his finger back inside her asshole, sliding easily on the burning oil that lined her delicate passage, her ass rising up high as his finger slid into her colon with a fierceness that dragged a deep scream from her lips.
“GGGGODDD,” it hurt when he thrust his thick finger into her reluctant asshole. Yet why was she keeping her ass tilted up in the air for him, her legs spread wide, her anus exposed and available? “It burns,” she cried out. “It’s too big.” She spread her legs a bit wider, hoping to accommodate the thick finger, opening herself up for his anal probing. He was undeterred from her screams of pain, fingering her asshole for ten minutes, his finger sliding in and out with abandonment, sliding back and forth over her clenching muscles as he used her.
“You need something bigger back there Princess, something closer to the size of my cock.” He pulled his finger from her asshole, popping as her hole closed, almost dejected from the loss of the stimulation. He didn’t let her get used to the feeling, pushing two fat fingers against her anus, pressing hard as his slick finger suddenly popped inside.
“TTTTTOOOO BBBBIIGGG,” she cried in pain as her anal ring felt as if it were tearing, forced to spread wide to engulf two fat fingers of the Captain’s. She pushed back with her muscles, straining to allow entrance to her most intimate hole as if she welcomed the intrusion. His fingers were not to be deterred, slowly spreading her open inside, twisting and turning inside her as his knuckles rubbed harshly over her anal passage. She felt the sharp pain in her stomach as his fingers entered her colon, deep inside her bowels, her stomach cramping in pain. God, is this what it would feel like when he sodomized her? He fingered her asshole for another ten minutes before he touched her pussy again, this time two fat fingers sliding between her lips.
Drenched, her pussy was wet with desire even without touching her. The anal probing had dragged up a deep, masochistic pleasure that touched her in places that she didn’t want to acknowledge. He began a gentle masturbation of her pussy while his fingers harshly fucked her asshole, her body bouncing back and forth between the pleasure and pain he was providing. She felt the fingers in her asshole giving her cramps when they pushed deep into her bowels, twisting, turning fingers that rubbed her delicate lining with his knuckles, feeling him trying to expand his fingers, stretching her until she moaned in pain. He would pull his fingers out until only her anal ring gripped the tips, then suddenly plunge them back inside her with such ferocity that it tore the air from her lungs. His other hand continued to snap back and forth over her hard and red clit, his fingernail dragging harshly over the super-sensitive bud. When he shoved his fingers inside her asshole, he would pinch her clit with two powerful fingers, forcing her to shove her ass back onto the two fingers already forcefully shoving into her bowels, driving them deeper and more painful into the depths of her bowels.
The Captain continued the duel ravishment of the Princess for over twenty minutes, driving her to the brink of orgasmic bliss then plunging her into the depths of painful hell, her asshole abused for his pleasure. He loved the way she squeezed his fingers, not sure if he could wait to sodomize her, to pleasure his cock inside her buttery insides. He stopped, removing his fingers from her asshole suddenly, seeing her anal ring stay open as if it was waiting for the return of his thick fingers before finally shrinking down, the hole now red and abused. He stopped touching her pussy, her hips moving about, trying to find the fingers that were giving her so much pleasure.
“Don’t stop, please. Let me cum,” she begged him, hoping he would give her the release she so badly desired.
“It is time for punishment again. This time on the table Princess.” He picked up the leather straps again, waiting to bind her in the position he wanted.
She wasn’t even sure why she said it, regretting doing so almost as soon as it came out his mouth. “Don’t tie me up. I get into the position you want me.”
“Even if I want you to spread your legs wide so I can whip your pussy again? You’ll keep the position even after the first time the whip slaps through your lips?” He looked at her, the sweat glistening from the candlelight off her naked body, her nipples so hard and pointed that they looked as if they would burst, her legs slightly spread, as she stood naked before him, her chest heaving up and down.
She didn’t even if know if she could do it, spread her body open for him to cruelly lash at her most intimate parts of her body especially after the first blow of the whip. She only knew that she had to cum, cum soon. If it took another whipping before he would masturbate her again, then she would suffer, hoping that he would let her cum. “Yes.” She climbed onto the hard wooden table, sliding carefully, her cheeks still red and tender, not wanting a sliver of wood piercing her intimate sex. She got into the center of the table, leaning back onto her arms, her knees drawn up slightly, her thighs together, waiting.