Maiden Maid-Chapter 7 Bound and Penetrated from Behind

Michael’s cock twitched as he watched her tiny asshole slowly engulf his finger, delighting in the way it began to spasm, the tiny opening pursing outward, opening and closing. He felt her sphincter squeeze the blood from his finger, the tightness of her hole would give his cock so much pleasure. He watched her legs tighten, trying to stand up on her toes to escape the finger, the bolster doing its job of keeping her ass arched up and available for whatever he desired. But right now he wanted to pierce her asshole with his fingers, opening her up for bigger things, his cock. He twisted his finger as he slowly pushed it in, sliding effortlessly on the oil, her silky insides clenching on the invading digit, the knuckles banging painfully on the sides as her turned his finger while driving it deeper.

Sara felt full, the thick finger moving deeper and deeper inside her, her bondage preventing all attempts to avoid it. It twisted as it moved inside her, the fat knuckles pushing hard against her insides as she tried to raise up to prevent it from going any deeper, until she felt the belt securing her to the bolster tighten, forcing her to let the digit slip inside her asshole higher and higher. She could feel it slide almost all the way out until only the tip of his finger was grabbed by her sphincter. “OOOWWW,” her head shooting up in pain as his finger plunged back in, the sound of his finger sliding on the oil in her ears as her asshole went from empty to full in just a second, the finger banging painfully into her insides as Michael twisted and turned his finger as he fucked it back in.

He delighted in the way her body bucked as he finger fucked her asshole, gasps of pain coming from her lips, as his finger began to push back and forth inside her, making her feel what it will be like when he fucks her with his cock, finger fucking her tight, hot teenage asshole. “Relax your asshole, Sara, you’re going to have to take two fingers,” not really caring if she did, just loving they fear he saw in her eyes when he told her. He pulled his finger out, pushed another finger along the first and began to slow descent back into her anal passage, her anus stretching wide to accept the two fat fingers, wrapped tightly around them as they plunged deeper inside of her.

She felt her anus stretching open to accept the duel ravishment of his fingers, the knuckles banging hard against her stretched anus as it was forced wider to accept them. They slid inside her, twisting and turning, her stomach beginning to cramp, the fat fingers filling her up. She felt him begin to finger fuck her asshole with his fingers, increasing the pain as they moved faster and faster, sliding over the slick surface, humiliated when tiny farts of air escaped as they pulled from her asshole.

Michael enjoyed the way her anus was wrapped so tightly around his fingers, the skin pulled wide, white from the stretching, her sphincter continuing its ineffective attempts at forcing them out, the spasms inside her anal tract increasing as his fingers pushed deeper inside her. He could see her body jerk when he fucked in with a rather painful fuck, knowing that he was providing her with a powerful cramp as he did. He would enjoy that with his cock, her cramping would tighten her asshole on his cock, massaging his cock to even greater hardness. He pulled his fingers from her asshole, her anus still grabbing onto the departing fingers, clenching on them as if they did not want them to leave. Even with his fingers withdrawn, her anus, now slightly red and swollen from the finger fucking, clenched and unclenched seeming to dance for him. He slapped her ass, the sound making his cock jump, knowing that it was time. Time when he would bury his hard cock inside her teenage asshole and fuck it for the first time. 

“OOOWW,” she cried out, her asshole suddenly empty, grateful that the painful stretching had stopped, but knowing that it was only temporary. She felt Michael move between her bound, spread legs, his cock head rubbed up and down her crease, pressing over her exposed anus before going down and gathering up her pussy juices on the swollen head. “Plllleeezze, NNNNOOO,” she cried, her body jerking forward, the bolster preventing everything but a tiny movement of her hips, the huge cockhead banging up against her anus. She felt his hips slowly push forward, her anus forced to widen, slowly engulfing the bulbous head. She felt a sharp pain, her anus now stretched wider then the fingers had forced it, still not wide enough to allow the rubbery cockhead inside her rectum.

Michael smiled as he looked down at her ass, making her take his cock millimeter by millimeter, wanting her to feel the slow pain as she was stretched for his pleasure. He stopped for a second, letting her anus grow accustom to the stretching before he pushed again, hearing her gasping in pain, her breathing rapid as she felt for the first time a hard cock forced inside her clenching asshole.
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She could not believe how much it hurt, the sharp, biting pain as her anus was forced to spread around the cockhead, gripping it like a rubber band. She jerked her hips, the leather strap digging into her, preventing her from escaping the beginning of the painful ass fucking. “AAAGGHH,” she cried out, “plllleezzzee, its tooooo big,” she begged, her anus now slipped tightly over the cockhead, gripping it right below the head, squeezing it tightly.

He thought it was going to tear the skin from his cockhead, finally slipping inside her rectum, her anus in a death grip on it, her sphincter clenching and unclenching, trying to force the foreign object from her anal tract, her hot and tight rectum pulsating on the flesh inside her. “How does it feel Sara, how does it feel to have a cock inside your asshole for the first time?”

“GGGGODDDD, it huuuurrrtss, pleeze don’t move,” afraid the withdrawal would be as painful as the entry. She felt like she was being split up the middle. The painful spreading and bondage of her spread legs was bad enough, not it felt like she was tearing up the middle. How could they enjoy inflicting so much pain on her? But she already knew the answer, she could feel his cock jerk in joy each time a cramp overcame her, her asshole clenching on the rubbery head, knowing her pain was giving him such great pleasure.

“I love the feeling of a virgin asshole on my cock, Sara. It will never be this good again, hearing your gasps as your asshole feels the first time the stretching to take my cock. It brings me so much pleasure, but it is time to continue. Continue the journey inside your asshole until you grip my entire hard rod, feeling it pulsating inside you. Scream if you want, John will enjoy it, knowing what you are enduring.” Michael began to push, his hands gripping her hips tightly, his fingers digging into her skin. He felt the head of his cock begin to push in. He pulled out, then back in again, each time sinking a little more of his hard cock inside the grasping anal tract of Sara.

Sara could feel every bump, ridge and vein on his cock as it slowly stretched her open, deep inside her asshole. It hurt, starting out as a burning sensation, then feeling like she was tearing inside as it entered virgin territory, opening up her asshole to something bigger then had ever entered or exited before. She began to cry, tears falling from her eyes, sobbing, her breathing ragged as she endured the painful entry, feeling like she was being stuffed from the inside. Her body would jerk in pain when he would push into the side painfully, a sharp pain shooting into her brain, a cry from her lips eliciting a jerking of his cock in pleasure. She felt the withdrawal of his cock, equally painful, the burning sensation returning. She held her breath, knowing that the withdrawal was followed by a sudden insertion again, each time reaching deeper depths inside her. “GGGOOD, AAAGGH,” his cock straightening her colon as it forced its path inside her. Her stomach cramped, unable to bend over, the bondage forcing her to endure the pain.

He was sure that his cock would be squeezed to death, her asshole applying painful pressure on his steel rod. He grunted, shoving with his hips hard, hearing her yelp as he plunged painfully inside her colon, feeling her body begin to spasm in pain, clenching on and off of his cock, pleasuring the hard cock painfully. He pumped in and out, her gasps of pain, her pleas bringing such pleasure to his organ. He finally pushed in, his balls slapping noisily against her pussy lips from behind, the swollen nuts hard, waiting for relief, waiting until he could unload his cum inside her asshole, giving Sara her first cum enema. But it would not be the last. While virgin asshole did give him pleasure, he also enjoyed an asshole that would not fight back so much, an asshole that would accept his punishing fucks in and out.

Her body was a sea of pain, his cockhead banging painfully against something deep inside her colon, pulsating inside her, igniting fresh bouts of sharp pain. She felt his balls slap against her pussy lips, his stomach pushed against her ass, his cock twitching inside her, fully buried inside her hot, teenage asshole for the first time. “Don’t move,” she cried out in pain, the cramping beginning again, each and every jerk of his cock bringing about new pain. 

Michael stroked her ass cheeks and back, her body covered with a sheen of sweat, feeling her tremble in pain. It felt like the blood would shoot from his cock, her asshole gripping it so tightly. “Such a nice asshole, Sara. So tight and hot, made for ass fucking. Such pleasure you bring to my cock, Sara. But now it is time to get your ass fucked.” 

She felt the slow withdrawal of his cock from her asshole, feeling like her insides were being drawn out with his cock, a vacuum formed behind the withdrawal. Her asshole went from full to empty in a matter of seconds, her body continuing to spasm in pain, even when empty of the punishing cock. She did not even have a chance to get ready for the plunge back in, his cockhead forcing its way back into her asshole, Michael’s hands on her hips tightening as he forced it into her resisting anal tract. She grunted in pain as she received over five inches of hard cock inside her before he ripped it from her body again. The next plunge shot his cock deeper, six inches of cock pushing into her colon, cramping her with the steely organ.

Michael enjoyed her grunts and groans of pain, pulling her head back by her hair, forcing her head up, riding her like she was a horse, bucking on his hard cock. He couldn’t believe the pleasure her asshole was giving him, the anal tract gripping his cock much tighter then a hand could, her spasms of pain forcing it to clench on the man flesh buried deep inside her. He buried his cock completely inside her, his cockhead banging painfully into her colon forcing the air from her lungs as she went from empty to full in a matter of seconds. He let his cock twitch inside her, making it jump, banging painfully into the sides of her colon. He reached around her body, grabbing her hanging tits in his hands, his large palms encircling the teenage globes and squeezing them tightly, feeling the flesh push through his fingertips.