Contest: Alternate Chapter

"You have no idea how much I've wanted to see you like this again," he whispered, half to himself as he turned and went to pull some toys out of a drawer. When he returned, he came up behind her, running his hand down her back and over the curve of her buttocks, his fingers sliding into the crease to probe at her hole. Danielle moaned and wriggled. She heard him dropping to his knees behind her, his hands spreading her buttocks even further as she could feel his hot breath on her anus as he inspected the hole she was sure that he wanted to breach next.

Anxiety made her breath come in short, hot pants as she tried to stay relaxed, tried not to clench her butt cheeks against him. Something wet pressed against her crinkled hole and she jumped before realizing that he was tonguing her there. It was a completely different sensation from being eaten out, pleasurable but strange and so decadently forbidden that she felt her holes clenching in reaction to just the idea. Never before had Danielle allowed Doug any kind of access to her asshole, the closest he'd gotten was when he'd been eating pussy and he seemed determined to make up for this lack now.

His tongue probed and delved, pushing the tip in and out of her hole as Danielle gasped at the rude intrusion. Even knowing how perverse some of Doug's fantasies were, he'd never mentioned anything like this! But from the eagerness of his mouth as he sucked and licked at her backdoor, she knew that he was truly enjoying himself. Having already found that anal wasn't as objectionable as she'd always though, thanks to this contest, Danielle gave herself over to the sensations and began moaning with the pleasure that she was feeling, pushing back against his questing tongue as much as she could.

For a moment Doug paused in shock at her reaction and then his efforts redoubled, the thick muscle of his tongue pushing its way into her anus, past her sphincter. Danielle trembled in her bonds, shuddering at the strange pleasure of the sensation, the tingling nerve endings in that sensitive area.

Suddenly he pulled away, his hands leaving her and Danielle moaned in disappointment. She'd just started to truly enjoy that. Noises behind her made her peek to see what he was doing and then she felt his fingers back between her cheeks, one slick digit poking rudely at her anus. The tip slid in with little resistance and Danielle moaned again. The more he played with her ass, the more her pussy throbbed with need for its own penetration. Instead his finger just slid deeper into her ass, probing the tight tunnel as each knuckled was forced through her clenching ring.

Doug's fingers were thick, so even having one inside of her was like accepting a small cock into that tight space. After all, it had been several days since her first anal penetration and it had easily and quickly shrunk back down to its original proportions.

Something brushed against her pussy and Danielle cried out her encouragement, pushing her hips back to try and increase the contact to her swollen folds. Doug teased her pussy with one hand as he pumped his finger in and out of her asshole. Just as she was about to start begging him to finger fuck her pussy, he slid the finger in her ass out to the very tip and then began pressing in with two of them, stretching her wider.

Groaning at the strain on her ass to accept two of his thick digits, Danielle trembled, her cunt's needs lessening slightly as the burning stretch in her ass became the most pervasive sensation she was experiencing. Doug twisted his fingers back and forth as he sank them deeper, creating an entirely new barrage of sensations for Danielle as her asshole strained and clenched. Then he brushed his fingers over her pussy lips again. By this time Danielle could feel her juices trickling down to almost mid-thigh, she was so horny.

"Please... please Master..." she begged, hoping that remembering to call him Master would help her pleas. "I need to cum."

In answer Doug removed his fingers from her pussy and gave her ass a sharp slap, making her moan and clench around his fingers in her back door. "You will cum when I'm deep inside your tight little ass and not before."

She felt almost like crying, the burning in her pussy wasn't subsiding at all and the slap he'd given her ass only increased her arousal, the sharp sting adding to the complex mix of sensations that made her need to cum so imperative.

Doug pumped her anus a few more times with his fingers before withdrawing them. Her asshole felt empty, but he didn't let that last for long. Something even more rigid than his fingers began to push into her. Fairly slim and pointed, it nudged inside her dark hole before it began stretching her as its size expanded down it length. Danielle whimpered as her ass hole swelled around it, quickly reaching the girth Doug's fingers had stretched her to. The hard toy was much more unyielding than Doug's hot flesh and she squirmed as her hole was stretched even more.

"Please, it's too big!" she cried out as her hole was forced wider, going up on her tip toes to try and escape the relentless intrusion. Her protest was met with a chuckle.

"I'm wider than this, sweetheart, so really I'm doing you a favor."

There was a sharp shove, the pain richoting through her as her asshole expanded and then clamped down tightly around the base of the plug, her tunnel quivering with the strain on her muscles. Even the base of the plug was thick, her tight ring clenching and protesting the stretch. Her breath came in gasps as her body adjusted to the large intruder, breathing through the pain and subsequent arousal took all of her concentration.

It wasn't until Doug was standing in front of her, hefting one large breast in his hand and wrapping rope around the base of it that awareness of her surroundings returned. Making a figure eight with the rope, Doug firmly secured both breasts so that they were standing out even more, rubbing his hands over the fleshy mounds in appreciation. It succeeded in distracting her from the burning stretch of her ass, especially when he lifted one succulent nipples to his mouth and between to suckle at the tender nub, pulling on it hard with his teeth.

Gasping and moaning, Danielle felt each nip of his teeth like a lightning bolt, going straight to her hungry cunt. She was so aroused that she was starting to feel light headed, and as he switched his attentions back and forth between her nipples – which were rapidly becoming more sensitive due to the bound state of her breasts and his oral attentions - she wondered if it was possible to cum from nothing more than nipple stimulation. Certainly her ass was rhythmically clenching around the plug inside of her as if it was a cock that was fucking her, her pussy convulsing in time. Every nerve ending felt like it was on fire, like there was a great gushing wave coming to sweep her away.

Then Doug removed his mouth and Danielle screamed her frustration as her pussy pulsed emptily. She struggled with her bonds for a moment, too far gone in animal need to think clearly. When she finally ceased her struggles, panting for air, Derrick was standing in front of her with a riding crop in his hand, watching her writhing with evident enjoyment. He'd stripped off his pants, probably because his hardened cock had become too uncomfortable within the tight confines of fabric.

"So my sweet Danielle... tell me more about this bet."

The crop tapped against his calf threateningly.

Danielle cleared her throat, trying to calm her thoughts and her body. "Violet and I went to Jared... we wanted to show each other up. He set us tasks for this week and we each completed the same number of them as of today... but if I spend three hours with you then I'll win."

Stepping forward, looking rather curious, Doug ran the flat leather end of the crop up Danielle's stomach, brushing it over her nipples. She tensed and shuddered, waiting for the slap, but he just continued to stroke her body with the soft leather.

"What tasks have you completed this week?"

Heat suffused her face and Doug raised his eyebrows. "That bad? Tell me." At the same time he commanded her to tell him, he slapped the crop lightly against the side of her right breast. More sensitive from the binding he'd put it in, the small slap both hurt and tingled deliciously.

"The first one I completed to was to have my tits tortured."

A cruel smile spread across Doug's face. "I can certainly see the appeal. What happened?"

He slapped the side of her left breast and Danielle jumped a little.

"He tied me up like this actually," she said with a little smile, hoping that it would get under his skin to hear about what another man had done to her. Surely he couldn't punish her for it since he'd commanded her to tell him. "Gagged me, bound my breasts like this but tighter."

"Not breasts, tits," Doug said slapping both of them with the crop in quick succession. She moaned at the flashing mix of pleasure and pain, he'd hit her hard enough to leave little triangular marks on flesh that was already turning pink from the bondage. Her nipples throbbed.

"He paddled my tits, really slapped them around. It hurt but it felt so good too." The crop slapped into her again, striking the sensitive undersides of her boobs and she arched backwards as she shuddered. "Then he undid the ropes around my breasts and massaged them with his hands and told me that things were about to get rough. He used rubber bands, big ones, that went all the way to the base of my breasts – tits –" another whack of the crop "and lined them. It hurt so bad with all the blood being trapped in them, it felt like he was crushing my tits."

Tracing down the center of her breasts, Doug encircled her nipples with the leather of the crop.

"Then what?" he asked his voice husky. Danielle shivered as he reached down with his free hand and began fisting his cock. Obviously her recital of the tit torture that Chris had put her through was turning him on as much as it was her and she couldn't decide whether that was a good or bad thing.

"He whipped my tits until I thought they might pop before he took the rubber bands off. When he pushed a vibrator in me I realized I was soaking wet." The crop came down hard on the tops of her breasts and Danielle moaned. "He released my arms so that I could lay down on the floor. Then he clamped my nipples used the chain between them to help him titty-fuck me."

She shrieked as the crop came down hard on each of her nipples in turn, jerking her wrists in reaction as she shuddered and writhed. The hard nubbins stood out further, begging for more punishment, slightly darkened by the impact. Doug walked around behind her, the crop tracing a line from her stomach to her back and down to her ass.

"What else did you do this week?"

"I served as a food platter for one of Jared's parties." The crop lashed her buttocks, making her cheeks clench around the thick plug inside of her. With her nipples burning and the sharp slaps he'd been giving her breasts, she was now assaulted with stinging pain on both sides as well as the deeper throbbing of her straining anal muscles. "I had sex with a woman."

Heat burned in her cheeks as she admitted this to him, glad that he was behind her where she couldn't see his reaction. The crop came down hard across her buttocks over and over again as she cried out and writhed. The marks stung, but more painful was the way her rear tunnel felt as it clenched and shuddered around the unyielding toy inside of it.

"What else?"

"I lose my anal virginity," she whispered.

The crop viciously lashed upwards between her legs, so fast that she could hear the air displacement as it moved, followed by the wet smacking sound as it hit the sensitive folds of her cunt. Danielle cried out and then screamed as it was followed by another and another. Her body danced as she squirmed and tried to get away, but the spreader bar held her open and vulnerable. The crop snapped against her clit and her entire body tensed, waiting for the next hit, the one that would allow her to cum... but Doug had recognized the sounds too well and she heard the crop dropping to the floor behind her.

"Oh please," she begged, tears leaking down her cheeks with how badly she needed to cum, her abused pussy aching for completion.

"Oh please what?" Doug murmured behind her, the anger in his quiet voice cutting through her like a knife. "Please have mercy after you gave this sweet ass to someone else?"

Suddenly he was in front of her again, shoving a gag into her mouth. The anger in his eyes was overriding the lust and Danielle quailed a little at the sight. Fear flashed through her.

"If you need to say your safe word while gagged, scream three times in a row while shaking your head." Danielle stared at him. Despite his declaration that red was her safe word for the evening, she hadn't truly expected him to honor it. He snorted in disgust at the expression on her face.

"Still thinking the worst of me. It's time for some hard truths," he said almost conversationally as he walked over the wall and picked up a flogger. Returning to stand in front of her he slapped the inside of her thighs, working his way up to her pussy as he spoke. "You asked me to tell you my deepest darkest fantasies. And I did. I did not ask you to perform any of them that you were not interested in, I already knew that you had boundaries that didn't include some of my interests. When you asked if I wanted to do any of them with you, I told you the truth and said yes. That didn't mean that I wouldn't be satisfied never having them fulfilled."

The flogger slapped between her legs as she tried to focus on what he was saying, not entirely understanding the point. Sparks of pain flashed through her tender folds where the many stranded whip landed.

"When you asked if I'd ever fulfilled any of them, I told you that I'd had a threesome with my cousin Tori. You then assumed that I'd had sex with Tori, not that you said that to my face." The flogger landed with a wet splat, but Danielle was too taken aback to yell. "You waited until you had left and then you wrote me a letter, filled with all sorts of assumptions and accusations that you never allowed me to answer." Another hard hit between her legs, and this time Danielle let out a muffled shriek. "You decided that sharing my fantasies meant you were expected to fulfill them and that I would never be happy unless you did. You assumed that I had sex with my cousin. You assumed that I was some twisted pervert bent on indulging in all sorts of perversities that you had no interest in, whether you wanted to or not."

The storm clouds on Doug's face told Danielle just how angry he was over her assumptions. It was true that after he'd told her his fantasies she hadn't want to talk to him; that she'd cut and run and then taken the coward's way out and broken up with him over email. A particularly nasty email. And then blocked his address so that he couldn't write her back, refused to take his calls, and in general didn't allow him any kind of explanation whatsoever.

"I would never have done anything that you didn't want, that we didn't agree on," he said with quiet pride, the flogger hanging at his side. The smell of her pussy filled the air, despite the shame that was filling her heart. Had she truly misjudged him so badly? "I loved you but apparently you didn't even know me. So tonight..." the lust reignited in his eyes and Danielle shivered as his voice deepened, his face coming alive with sensual anticipation. "Tonight I will fulfill some of those fantasies with your luscious body, now that it comes freely offered. And maybe we'll both learn something."

That last was said very quietly as he moved behind her, trailing his finger down her arm and side to her hip. Danielle struggled with the idea that he might be telling the truth, that he might not just be saying this with hind sight, and she wished that she'd talked to him before after sending him the e-mail.

Then he palmed her buttocks, squeezing the creamy flesh hard, digging his fingers in and she found her thoughts and regrets fading away as the rough mix of pain and pleasure rippled through her. The stinging pain from the crop remained, an overlay of sensation on top of the hard gripping. Danielle squirmed as he pressed his fingers against the base of the butt plug, pushing it deeper. Then he began to pull it out and she gasped as the tight ring of her ass stretched around the bulbous base before the plug began to slide easily out. The receding sensation was a relief and yet strangely painful.

As her hole gaped, she could feel Doug pressing the thick helmet of his cock to it. Slick with lubrication, the velvet soft mushroom was thicker than the plug. His shaft began to press into her, so much more intimate and hotter than any toy. And unlike the toy, his cock was thick all the way down.

"Fuuuuuuuck..." he groaned in her ear as he began shove his dick into her gripping asshole. The first few inches slid in easily thanks to the plug, before the stretch of her muscles started burning again as he forced his way deeper and deeper into her cramped tunnel, taking long, burning strokes. He unsnapped the gag behind her head and pulled it from her mouth. "Tell me how it feels Danielle..." His breath came in lustful, ragged pants. "Tell me how it feels to have my cock sliding inside your tight ass."

"Oh God... too big... please... Doug, slow down... oh fuck..." Her squirming was to no avail; his cock seemed endless as more and more of it sank into her body, working its way up her dark channel. The interior of her ass felt like it was on fire, burning with the strain and rough friction of this intimate probing.

"Master," he said, reminding her of his orders and not slowing his pace at all. Truthfully he wasn't going so fast that she was in real pain, but with a cock as large as his there was a great deal of burning discomfort and straining muscles.

Danielle gasped as he thrust upwards again, burying more of himself, but his groin still wasn't touching her ass cheeks, there was still more of him for her to take. "Please Master!"

Reaching around to her front, Doug pushed his fingers into her sopping cunt and Danielle half screamed, half moaned her response as her insides clenched around him.

"I want you to feel the burn," he said in her ear as he stroked her pussy, force-feeding more of his meat into her rear entrance. "We both know that you like it better when it hurts." He shoved again and Danielle finally felt his groin pressing against the soft curves of her ass, his hard body rubbing against her beaten cheeks. "Is the pain making you hot Danielle?"

"Yeeeeessssss..." she let out a low moan as he pulled half his cock out of her and then shoved it back in. Hard. It felt like he was rotting around in her stomach, like she might feel his cock pushing up into her throat.

Although he couldn't help the pain that came with having a cock the size of his embedded in her nearly virgin anus, Doug seemed to be surprisingly careful of her pleasure as he began to rhythmically fuck her ass with slow and steady strokes, allowing her body to accustom itself to this shocking intrusion. His fingers pushed inside of her cunt, curling into her body and searching for her sweet spot, the heel of his palm rubbing wonderfully against her clit. The pain and pleasure surged inside of her along with his steady thrusting, melding into that sweet of mix of sexual torture that made her hottest.

Clenching down on his fingers and dick, Danielle could feel her denied orgasm rushing towards her, the surprisingly gentle fucking of her ass only increasing the tumult of sensations that rose within her. She cried out in glorious rapture as her holes tightened and released, sizzling heat spreading throughout her body along with her sweet release. Just as she had been denied forever, the pleasure seemed to go on that long, spurred by the relentless steady strokes in her back door and Doug's knowledgeable fingers. Her body spasmed as she said his name over and over again, wondering why she hadn't let him do this to her before.