Maiden Maid Ch 5 The Punishment

Michael did not wait for any further response, the ruler continuing to beat upon her naked ass and sex. He proceeded slowly, allowing her body to calm down before inflicting another painful swat on her, making her feel the full effects of each swat. The wooden ruler played all over her naked sex. It hit her ass cheeks, her asshole and finally he played the ruler up from the floor and hit her unprotected pussy, the wood splatting noisily against her wet inner pussy lips. His cock hardened each time as he tore screams from her lips, her feet dancing on her toes as she performed a “punishment dance” for his pleasure. He would stroke his fingers up between her pussy lips, preparing her, making her wetter for the wooden ruler to slap hard against the inner lips. She consented to his ministrations, her pussy juicing up each time with his fingers, her lips pulled back, exposing her pink inner pussy lips. Soon the lips turned a deeper red, the wooden ruler taking its toll on the tender flesh. She would gasp as his fingers touched the tender flesh. “And twenty,” the wooden ruler pushing hard down on her asshole, her loudest scream tore from her lips. He saw her body slumping down on the desk.

Sara could not believe the pain between her legs. The wooden ruler had taken the toll on her body, especially on her tender pussy. Michael had been so cruel, to beat the most intimate part of a girls body and she worried about what else he was going to do. She cringed when she heard his next command, but she had expected it.

“Take off the rest of your clothes. I want you to strip naked for me and then it is on the punishment bench for you.” Michael watched as she stood up from the desk, her body moving slowly, reflecting the pain he had inflicted on her body. She turned and faced him, her fingers moving to the buttons on her blouse, slowly opening them. She pulled the blouse from her shoulders and let it fall to the floor. “The rest, strip off the rest.” She let the camisole fall from her shoulders and slink down to the floor, her naked breasts revealed to him. “Very beautiful Sara, especially that red bush. I imagine it is a little sore now, but soon it will feel the effect of my hard cock taking your virginity.” His hand reached down and his fingers brushed through the silky, red pubic hair. He laughed when he felt her wetness. “I knew you would be like this, Sara. It seems that your pussy liked the attention I gave it,” his finger pushing up inside her vagina until he reached her hymen. “Spread your legs,” he ordered her. 

Sara shuffled her feet farther apart, the strange feeling of having a fat finger inside her vagina making it difficult. She stood naked and spread before him, his finger bumping hard against her hymen. She knew that soon he would tear through it. His fingers continued to play through her pussy lips, pushing them aside as his fingers played along the slick surface. 

He pushed her towards the bench, his hands leaving her pussy. “Kneel down her,” he ordered her. He shuffled her body down on the punishment bench. He opened the pillory in the front, pushing her head between the wooden stocks. He let the wooden stocks fall, trapping her head between them. Her wrists were next, soon bound tightly between the wooden slats. Sara could barely move her upper torso.

She was really getting scared now. Michael had her bound tightly into the wooden stocks in the front, unable to move her head or her hands. She felt his hands fumbling with her legs, pulling them apart, her knees dragging painfully on the bench as she was spread open again. He kept pulling until her legs were spread obscenely and then locked them into the wooden stocks. She felt his hands moving up between her thighs, rubbing her tender inner thighs with his callused hands. She felt the fumbling between her knees as Michael placed a spreader bar between them, a thick wooden dowel with leather straps to keep her from closing her knees. 

“Let’s get that nice ass up high, shall we, Sara,” Michael’s hands pushing the rear stocks up towards her head, forcing her ass to rise up, thrusting her delectable ass cheeks up. “Yes, so much better,” his hands running over her ass, her cheeks spread open, her pussy pouch and asshole spread for his pleasure. His fingers sought out her spread open asshole, rubbing some moisture from her pussy up to it. He saw her trying to squirm to avoid fingers but John’s bench prevented all movement. He slapped her ass, “still, I don’t want any trouble out of you.” His fingers returned to her asshole, running around the tiny opening, feeling her trying to clench her ass cheeks together. He pushed his finger into her asshole, feeling her sphincter grabbing tightly onto the tip of his digit as it slowly pressed into her.

“Ow, not there, please, no.” It felt uncomfortable, the finger moving around inside her rectum. Her tiny asshole had to stretch painfully, although it was only a finger. She could feel it begin to push in, stretching her asshole open as it plunged ruthlessly up her asshole. “AAAHHH,” she moaned in pain as one finger became two, twisting and turning in her unused back passage. Her sphincter grabbed onto the invading digits, clenching and unclenching on them in response to the unnatural act. 

“You’re going to make a good assfuck, Sara. Your tight asshole naturally clenches on whatever is shoved up it. You may not like having a big, hard cock up your tight asshole, but anyone that does will love the way your asshole will squeeze the cum out of them. But first your punishment and then it will be time to get rid of your pesky virginity. I think the paddle first, then the studded paddle. I want a nice set of red asscheeks. Are you ready, Sara?”

Sara tightened her asscheeks as she felt the wooden paddle lightly caressing her spread cheeks. She could feel her juices running down the inside of her thighs. God, how could she continue to be wet, knowing that soon the paddle would beat a painful tattoo on her cheeks. She screamed the first time the paddle hit her asscheeks, the broad paddle smacking a large portion of her unprotected flesh. She could barely catch her breath when the paddle came crashing down again. “OOOOWWW,” she cried in pain, her ass moving in a circle, unable to get out of the way of the cruel paddle. She could feel the heat in her tender skin as the paddle continued to beat the flesh. She would not be able to sit for a week.

Michael’s cock hardened even more as he watched Sara’s bound body absorb the bruising smacks of the wooden paddle. It shown a bright red, her asscheeks clenching and unclenching, her tiny asshole peeking in and out of sight. As soon as he had hit her with 20 strokes, he picked up the leather paddle with the bright metal studs. His hand ran over her asscheeks, feeling her flinch in pain as he felt the heat of her skin. “Now to really make it tender. When I fuck you from behind, I am going to bump up against your sore ass. It’s going to make you move around, giving me a nice fuck. It may hurt you, but that does not matter. Your only concern is to give me a good fuck.”

“OOOH, GODDDDDD,” she cried out in pain as the leather paddle and the studs smacked harshly against her already tender asscheeks. It felt like the studs were tearing her skin apart. “Smmmack,” the paddle again striking her upraised bottom, her ass dancing under the spanking she was receiving. She knew that she was spread obscenely to Michael’s gaze, her ass moving around like it was fucking the air. “OOOOOOOWWW,” her voice turning hoarse from screaming as the paddle slapped between her open thighs, hitting the tender insides, first on one side then the other. “Please, no more, please,” she cried out in pain.

Michael stroked his cock as he observed her beet red ass. Soon he would bury his hard cock in her virgin pussy, but first he still had to tenderize the prize. “Rise up higher,” sliding the stocks in the back towards her body, forcing her ass to move up higher. “Wider,” taking first one leg, then the other out of the stocks and placing them in the outer rings. Her legs were now spread over 5 feet wide, her moans of pain reflecting the pain she felt as she was almost ripped up the middle by the obscene spread of her legs. The position she was in almost looked ridiculous, the arch of her ass into the air forcing an almost comic scene. But Michael’s purpose was satisfied, opening her pussy to the lash of the riding crop. “Now you will feel the lash of the riding crop on your pussy. Your pussy lips are spread back, the pink inner lips gaping open. You will be surprised at how much punishment your pussy can take. It will hurt and you will scream in pain, but it will make my cock so hard,” laughing as he lightly tapped her pussy with the crop, feeling her body shudder in fear.

“No, not on my sex, please don’t, I wouldn’t bite again,” she cried out, her ass already smarting from the paddling. “You shouldn’t hit girls between their legs.” She knew that her pleas of help would do no good. She learned in the orphanage that men liked to use their power to abuse young girls. She had heard the other girl’s talk about how Mr. Smith, the head of the orphanage had subjected some of the prettier girls to humiliation and had sexually abused them. They were continually subjected to punishment in his office where he would force them to strip naked, inspect their bodies and subject them to corporal punishment. Before allowing them to leave, they would have to sexually service him in whatever manner he chose. He had heard the girls even talk of being taken anally and now that she had suffered under Michael and John, she knew this to be true. They seem to take great delight in playing with her tiny asshole and she was sure that someday Michael would be putting his hard cock into her asshole and sodomizing her. She did not look forward to that day.

Michael stroked his cock as he looked down at the spread body before him. Her legs were spread obscenely, her pussy gaping open, her asshole exposed. He rubbed the whip, feeling the supple leather, it would be soon wet with the juices from her body. He knew that Sara would feel the pain of the crop, but he also suspected that she would also be extremely wet from the experience. The sickening sound of the leather riding crop hitting her sensitive flesh rang out in the room. Michael had brought the crop up from the floor, it moving silently through the air as it shot up between her legs until it struck between her spread pussy lips.

“AAAGGGHH,” Sara cried, her head rising up, her eyes wide open in pain. The crop had lashed at her pussy but it took long seconds until the pain shot up her spine and reached her brain. “NNNNNOOO, no more,” she cried out, her face contoured in pain as she braced herself for the pain again. She did not have to wait to long. She could hear the crop whistling through the air this time before it smashed into her left pussy lip, slapping at the puffy flesh with a resounding thud. Her body jerked in pain, the punishment bench doing its job, holding her firmly in place and spread open. It felt like her pussy was on fire as the leather beat the sensitive flesh. 

Michael moved the crop between her legs at the juncture and slapped the crop back and forth, beating at each tender thigh, each time moving up and down her thighs, the flesh first turning pink and then beginning to turn a darker red. The crop reached the top, and began a series of short, sharp slaps of the leather crop against her pussy. He watched as her body jerked up and down, unable to keep up with the constant barrage of pain shooting between her legs. Her pussy lips shuddered under the crop, turning red as Michael beat the flesh. “I love so much beating your pussy, Sara. Love to hear your gasps and shouts of pain, unable to stop what I am doing to your lovely, young body. Do you want me continue, Sara, or are you ready to surrender your virginity to me?”

“Ohhh, Godddd, it hurts so much,” she cried out, the sound of slapping flesh ringing out in the room, the sound of the creaking of the wood of the punishment bench as she moved around as much as she could in the strict bondage Michael had forced her into. “No more,” she cried out again in pain, tears running down her face, her eyes opened wide in pain. She did not have to wait for an answer, the crop swung up from the floor again, the power of Michael’s force behind it, smashing between her split pussy lips, striking hard on her virgin pussy. 

“Yes, you scream so well,” bringing the whip down from over his head this time, striking her unprotected asshole. The tiny hole, nothing more than a star, pink and exposed received the brunt of the crop as it smashed down. 

“GGGGGGGOODDDDDD, AAAGGGGG,” Sara yelled out. When she thought it could not get any worse, it did. It felt like the crop was tugging her tiny asshole out of shape, driving it deep into her body when it struck. She did not expect him to hit her there, but she should have. Men had such fascinations with her asshole.