Punishing His Ward

by Golden Angel

  Watching her face, the Earl closed it around her nipple.

  Cynthia's eyes bulged in shock. Her head threw back, banging against the pole, but that brief flash of pain was nothing compared to the deep, sharp ache of her nipple being squeezed in an unforgiving grip by the silver clamp. It was like nothing she'd ever felt before. In the past she'd pinched her nipples rather hard, but this was more than a mere pinch - and unlike a pinch, the pressure didn't release when the Earl moved his hand away. It held on, crushing the poor, tender bud.

  She tried to shake it off, her breasts jiggling, which only ended up increasing the pain as the little jewel bounced and tugged on the clip. Because of her position, she couldn't move much anyway, and she whined behind her gag as the Earl smiled wickedly, lifting her other breast. Cynthia was quite sure that he knew exactly what the clip was doing to her and he enjoyed seeing her attempts to alleviate the painful pressure.

  The pinching of her other nipple was both easier and worse. Worse, because now she knew exactly what to expect, easier because somehow having the pain balanced out made it slightly easier to bear. Her nipples throbbed in their confinement, seeming to be on a straight line down to her little clitty which pulsed in sympathy. It wasn't like the pain being spanked, but her body had the same reaction - arousal.

  Pulling away from her, the Earl spun her around, pressing her against the bedpost so that it nestled between her breasts. The initial painful pinch of her nipples was slowly dissipating, and although she could still feel the awful pressure, it was beginning to feel almost good. Her body obviously had difficulty discerning the difference between pleasure and pain. Because of her position on her toes, she was now off balance and she found herself pushing her rump out at him. Cynthia moaned and wriggled, but her large breasts on either side of the post - not to mention his hand on her neck - kept her from being able to turn back around.

  SNAP - CRACK

  Pain whistled through Cynthia and she screamed behind her gag. Whatever he'd hit her with had left a thick line of unhappy, throbbing flesh behind across the center of her buttocks. She would have danced away, but she had no room to maneuver, and her jiggling was causing her breasts to bounce, which meant her nipples were being tugged by the weight of the jewelry again...

  SNAP - CRACK!

  She screamed again, this time before the crack of pain even bit into her flesh. The snapping sound was the wind-up, but it let her know what was coming a moment later. Tears sprouted immediately traveling down her cheeks to soak into the cloth gag that she ground her teeth against the burning lashes.

  "You're lucky it's only my belt and not a birch," the Earl said, chuckling at her reaction. Cynthia tried to growl at him, but it came out more like a whimper. His belt! "Don't worry sweetheart, I'll have a birch made for you tomorrow, just in case you decide to be particularly naughty again."

  This time Cynthia really did whimper. She'd never been birched before, but if it was worse than this, she didn't really want to try it. The two stripes across her bottom were already more painful than any spanking he'd meted out, almost obliterating the throbbing sting in her nipples which had either faded or was just obscured by the belt welts.

  SNAP - CRACK!

  The belt caught the underside of her bottom, causing her to jump slightly, which tugged on her wrists. Her breasts bounced even more, reigniting the flames in her nipples and Cynthia twisted and sobbed. The Earl's hand on the back of her neck wasn't punitive, but it did keep her from being able to move around too much - later she would realize this was in part for her safety - if she had managed to turn around the belt would be snapping against much more tender areas! But right now all she could focus on was trying to get away from the painful lash, not realizing that he was doing her a favor by holding her in place.

  SNAP - CRACK!

  SNAP - CRACK!

  SNAP - CRACK!

  Her ears seemed to fill with the sound, the rounded cheeks of her backside feeling swollen and bruised from the punishing leather. Cynthia found herself doing a little bouncing dance that she couldn't stop, even though it made her nipples and their clips bounce and sting as well. The gag was becoming soaked through with her tears where it covered her cheeks and she sucked on the cloth as if it could provide some sort of comfort.

  Eventually, she couldn't say after how many strokes, it ceased. Cynthia slumped against the bed post, letting it take her weight as she sobbed. It felt like her bottom had been set in a fireplace and left there to roast! The Earl's deep, crooning voice, murmuring that she’d been a very good girl, made her feel marginally better as he turned her around. He kissed her forehead and her eyes, ignoring the fact that her lashes were wet with tears.

  Probably she should hate him, but Cynthia found his gentle hands on her hips and her sides comforting, his gentle kisses even more so. The expression on his face was softer than she’d ever seen before, warmer, and he told her that he was proud of her for taking her punishment so well. This was a side of him she hadn't seen before and it made her want to snuggle into his arms and just weep for the pain in her bottom.

  Then the bastard unclipped the jewelry from her right nipple and Cynthia screamed again. It was much worse than when he'd put the jewel on. The release of pressure brought with it a rush of tingling sensation that was like little needles being pricked into the tender bud - a thousand of them, all at once. Lowering his head, the Earl took the tortured nubbin between his lips and sucked. The sensation was almost too much for Cynthia and she sobbed again, caught somewhere between intense pleasure and pain.

  When she felt his fingers sliding over the curls of her mound, down to the lips of her pussy, she moaned. She hadn't realized it before, she wouldn't have thought it possible, but she was so wet that the top of her thighs were slicked. The strapping he'd given her might be the most painful thing she'd ever experienced, but one certain part of her body had been highly aroused by it. Cynthia moaned as he suckled her nipple, soothing the biting flares of pain with his tongue, and one long finger probed between her pussy lips.

  Looking pleased, he pulled away and watched her face as he reached for the other nipple. Cynthia shrieked into her gag, begging him not to with her eyes, as one long finger slid inside of her body between her legs and his fingers closed around the jewelry.

  This time they could both feel her pussy clench as he removed the clip and the stabbing needles returned. The Earl lowered his mouth to this breast as well, suckling and soothing the tortured bud. She was on fire all over; her bottom, her nipples, and now between her legs where his finger was exploring her quim in a decidedly pleasurable manner. It confused her even more than the spankings had; how could such brutality inspire such a response? She was riding his finger, wanting more, despite the fact that her bottom banged painfully against the bedpost every time she moved her hips in an attempt to get it.

  When the Earl finally lifted his head from her other sore nipple, he stood and wrapped his free arm around her body, pressing her against him. Her breasts were squashed against his hard chest, her sensitive nipples abraded by his body hair, and her netherlips forced even further open on his hand. Cynthia moaned and her hips jerked, tears springing to her eyes as her bottom throbbed painfully against the hard wooden post behind her. Blinking, she looked up into the Earl's eyes and realized that he was watching her quite closely.

  "You are perfect," he murmured, lightly brushing his lips over hers, even though he couldn't truly kiss her because of the gag.

  ******

  The wet vise of Cynthia's cunt was squeezing his one finger so tightly that it was a wonder his blood was still flowing. His cock seemed to throb in time with the pulse that was pounding through that hand, as if his finger was only an extension of his manhood. If only he could replace one with the other.

  But what he planned to do was going to be just as pleasurable, if not more, and it should make the hierarchy of power quite clear to his soon-to-be wife. If she hadn't gotten the message already. Grinning, Wesley reached up to loo
sen the gag and she spat it out of her mouth so that it fell around her neck. Her lips were swollen, her eyes red even in the moonlight, cheeks streaked with tears, and yet her spirit was unbroken.

  As she opened her lips to say something, his mouth came crashing down on hers and he swallowed her words as he ravished her mouth with his own. He could feel her little whimpers, her squirming, as he pressed her back against the post. The clenching wetness around his finger pulsed and she rocked on his hand, all of her weight becoming supported by her hot quim as he forced his leg between hers and lifted her onto his thigh.

  She was soaking wet, her juices coating his hand and now dripping down to his thigh. The little noises she was making could be of pleasure or pain, but it was more likely a mix of both.

  Wesley groaned into her mouth, pushing harder against her. She was so soft and helpless, and so perfectly aroused by the situation. In his wildest dreams, he had never thought he'd find a woman that would complement him so completely. While he knew she was surprised by her body's response to any kind of punishment - that had shown clearly in her face - the fact was that some part of her loved it. Craved it. Needed to feel it in the same way that he needed to dole it out.

  And she still didn't seem to be able to keep herself from baiting him, which meant that he should get to discipline her quite often. Something to look forward to.

  Tearing himself away, he reached up to undo the sash around her wrists. She moaned a little as her arms were lowered, shrugging her shoulders as if the position had been uncomfortable. Wesley rubbed his hand up and down one of her arms, from her elbow to her shoulders, helping to restore the blood flow to her limbs; her head tipped back and she smiled up at him, licking her lips in anticipation. She wasn't going to get what she was obviously expecting.

  Turning her around, Wesley pressed her down so that her upper body was resting on his bed. Putting his foot between hers, he pushed her legs apart. She made a faint little sexy noise as her breasts squashed against the bed and he was sure that her nipples would be feeling particularly sensitive after the clamps. The sheets on his bed would rub against them, arousing her even further. And tomorrow she would feel every twitch of her dress against the tender nubbins. The wet folds of her pussy glistened in the moonlight, deep shadows making the lips look nicely pronounced.

  In this position he could truly appreciate what his belt had done to her luscious bottom cheeks; he could see the raised sections from the edges of his belt, the swollen redness of the rounded mounds, and the darker spots that would be slightly bruised on the morrow. When he ran his fingers over some of the raised welts, Cynthia hissed and then moaned, her hips wagging up and down. And her sweet little cunt became even wetter, begging for his attention.

  Instead of complying with her obvious desire, he put his hands just below those open lips and pushed her thighs even further apart, kneeling down and licking along the outside of her pussy. Cynthia gasped and then moaned as his tongue slid up her sweet center. She tasted of honey and musk, and it might have been his imagination, but her virgin cream was the sweetest he'd ever encountered.

  He teased her with his tongue, not wanting her to find satisfaction yet... in fact, he wanted her to be wild before this next part. While he was licking and teasing her cleft, he was also pulling out the box of dilators from the Indian chest. Since she was holding her legs far apart for his tongue, he could use both of his hands for the next part of his preparation. Taking the smallest one, he smeared it with the oil he'd brought back from India. His cock surged as he stood up, placing his hand on the small of her back.

  With both of his feet placed on the inside of hers, he ensured that she wouldn't be able to close her legs against him. He pressed the tip of the narrow black rubber dilator to the crinkled rosebud of her anus and began to push in.

  ******

  Cynthia bucked at the strange sensation of something touching her most intimate area. She’d been lost in a haze of pleasure as the Earl had used his mouth on her, eliciting sensations that she’d never felt before. But now he’d stopped and he was trying to do something else entirely. In all the times she'd touched herself, all the time men had touched her, she'd never imagined and they'd never eluded to something like this!

  "Oh stop!" she cried out, rather frightened. Whatever was pushing insistently inside of her was incredibly hard, and pushing back against it did nothing to dissuade its entry into her backside. "What are you doing?"

  Bad enough that he'd teased her into a quivery, wet mess of lustful need, now he was doing something completely unnatural that did nothing to quench the craving between her thighs. Cynthia's breasts rubbed against the covers, her nipples throbbing as they were rubbed, while she tried to squirm away from the Earl's hard hand on her back. He held her easily in place as the thing entering her bottom nudged deeper.

  The tight ring of muscle stretched, and whenever she tried to push it out, it only burned worse and continued its path inwards.

  "Just relax," the Earl said, almost soothingly. "It will make this easier. And if you're going to be constantly disobedient enough to earn more than a spanking, you'd best get used to this. Anytime you're naughty enough to merit being birched or strapped, I'm going to follow it by punishing you inside this sweet little arse as well."

  Cynthia moaned as the thing seated itself snugly within her. For the first time in her life she felt embarrassed by something a man was doing to her... and yet not even that stymied the flow of wetness from her quim. It just excited her more that he was doing something so perverse, so unnatural, so... so... dirty to her and she couldn't do anything about it.

  Then the thing began to move, withdrawing and pushing back in again, the same way his finger had moved in and out of her pussy earlier. It felt strange as it withdrew, and uncomfortable as it re-seated, and yet it wasn't entirely bad. There was something exciting about feeling it moving back there, the sense of fullness every time it was pushed in and the way her back passage burned as it was violated. Cynthia tried to relax, knowing that she couldn’t get away anyway as his hand pressed down on her.

  Just as it was starting to feel almost good, as her hips were lifting up to meet the downward stroke, the Earl pulled it from her completely.

  "Oh please," she said, the words spilling out before she could stop them as she lifted her hips.

  She heard him laugh and she moaned with embarrassment, glad that she couldn't see his face. "This isn't for your pleasure, minx, remember?"

  Something hard and cold pressed against her lubricated channel and pushed in. Cynthia gasped as she was stretched wider. It felt like the same thing he'd been using before, but bigger and not yet heated by her body, which made it feel even more uncomfortable as it was pushed into her slightly stretched hole. She writhed, trying to escape the uncomfortable stretching, the muscles surrounding that area beginning to burn all over again.

  It went deep inside of her, deeper than the first one, and stretched her so much wider. Cynthia groaned and twisted under the Earl's hand, impaled on the hard rubber that was probing her body. But she'd learned a bit from the first one and she forced her muscles to relax, making it easier for the thing to enter her and sink deep, without any extra burning.

  But when he began to move it back and forth inside of her, she couldn't help but clench as the intense sensations washed through her, and her spasming hole made the probing burn even more. Cynthia moaned and squirmed, the unaccustomed sensations confusing her.

  “Please… more slowly… oh… please stop…” she begged, shuddering and squirming.

  “Shh, you can take this,” he said. “I’m going to stretch this sweet little arsehole and get it ready for me.” She didn’t understand what he was saying, his words didn’t make sense, but she did know that the Earl seemed to delight in her begging and her useless attempts to squirm away. She didn't know why she didn't just reach back to stop him; perhaps fear that he might tie up her hands again and then she truly would be helpless against this assault on her privates
. Just the idea made her body spasm again, but she wasn’t willing to admit it.

  As before, just as she was beginning to take the invasion more easily, the Earl set the thing aside and she found a third one striving to gain entrance into her tight hole. Cynthia cried out as it pushed past the protesting ring of muscle, her poor burning hole between her poor burning buns was becoming more than she could take, especially the way her body confused pain with pleasure.

  She desperately needed to climax, the need growing with every violation, and yet there was no relief in sight from either her desperate erotic craving or the torture that the Earl was inflicting on her backside. First he'd made her outsides burn, and now, as promised, her insides were burning just as much. The sensations were even more intense this third time around, she could feel every inch of the awful intruder as it nosed further into her body than she would have thought possible.

  "Oh please!" she cried out again, begging him to stop. And yet, she didn't know what she would do if he did. Part of her didn’t want him to.

  There was no need to worry, the Earl was completely unmoved by her pleas as far as she could tell, firmly driving the hard rubber between her cheeks. Her poor hole was beginning to feel quite sore from the stretch and the friction, her backside was fuller than it had ever been before. Cynthia gripped the sheets, her toes curling as the strangest sensation went through her in a rippling spasm; it wasn't quite pleasure, but it definitely wasn't pain either. It left her breathless and panting, her quim clenching eagerly. In some ways it almost felt like when she rubbed herself to a climax, but it was different from that too.

  The thick rubber prod withdrew and Cynthia moaned, in both relief and disappointment. Her entire body slumped over the bed as she panted. She felt horribly empty, and yet also hopeful that the strange torment was over.