Poker Loser Ch. 06

Leaning back, he began whipping her open pussy, the ends slapped against her inner and outer lips painfully, although nothing hurt more than when they impacted her tenderized clit. She whined - high-pitched - as he began slapping lightly. Grinning at her, he reminded her, "See, nothing where your parents will be able to see." Her face reflected her resignation as she realized that she'd put herself into this position. Slowly he began making the slaps harder as she began moaning, putting a little bit more force behind each one. Very soon, Allison was weeping again as he whipped her vulnerable pussy. Once the noise level behind the gag started growing, Todd suddenly stopped and then lowered his mouth to her pussy, licking gently along the sides and pushing his finger her hole to rock the balls. Very quickly the pain was overridden by the pleasure, especially with the balls rolling around inside her, and she began a different kind of moaning, trying to move her hips with the strokes of his tongue. As soon as she started that, Todd pulled back with a wicked gleam in his eyes.

Allison's heart sank as he began whipping her splayed pussy again, it seemed to hurt twice as much as the whip encountered her aroused flesh. She squirmed and whined, trying to get back some of the pleasure that his tongue had brought her. Twice more Todd stopped whipping her and licked her, before resuming the beating on her pussy. Each time it took less time for her to start sobbing, and for her to start responding with arousal; her pussy was burning with need even as he whipped it, and quivering with pain even as he licked it. Finally he brought her to the very brink of orgasm with his tongue, and grabbing the riding crop, he slammed the flat of it hard onto her clit several times. She screamed her orgasm as the pain flared through her clit, sending her body soaring on an intense orgasm that was almost too much to bear. Todd continued to crop her pussy and clit, a little lighter as the sounds of her orgasm slowed.

Her eyes opened, tears clinging to her long lashed, as he spoke, "That was for defying me, after I'd told you what was going to happen." Allison nodded, she remembered all too well that after he'd told her she was going to have sex with her step-cousin that she'd continued to argue. Exhausted, and filled with pain now that the intense pleasure had drained away, she hoped that her ordeal was over. Todd ignored the hopeful look in her eyes and pulled the balls from her sopping pussy, then untied her legs. He wanted to feel her body moving underneath him, but he left her arms tied to the bedpost. In her current state he wasn't sure that she wouldn't try to fight him a little, but he didn't want to have to punish her past her breaking point. She seemed to be pretty close to that already, and he hadn't even gotten off yet.

Spreading her legs with his thighs, he began to push his thick dick into her tortured pussy, which was made all the more painful as her pussy was tighter than usual since the plug in her ass was taking up so much room. As she yelped and whimpered, he could feel her slender body wriggling beneath his, as his dick buried itself in her wetness; the pressing of his body against her abused cunt was torture, and his chest against hers brought back the reminder of pain through her nipples and breasts. Slowly, he began to pump in and out of her, letting each agonizing inch of his dick pull and push at her sore and bruised pussy flesh. As he moved within her, he also lowered his mouth to her swollen nipple, gently rolling it with his tongue. Despite the pain his mouth on her nipple caused, it also sent little shivers of pleasure through her body, and he began moving a little more strongly as the slight sounds behind her gag indicated that it wasn't just pain she was feeling. He transferred his mouth to the other nipple, giving it the same tender, soothing treatment. Slowly, the pain in her pussy began to burn with pleasure as well, the soreness giving way to the gentle treatment of her body.

Carefully he worked her body, moving just enough to let pleasure start overriding the ordeal he'd put her through. Her sore and abused clit slowly began to respond positively to the movements of his body, and even the plug in her ass seemed to add to the sensations that began coursing through her. The gentle and soothing treatment he was giving her was like calming balm, making her feel like the Princess he called her. For the first time he was treating her almost as she wished a lover would - the only difference being that she'd never wanted a lover to have her handcuffed to the bed. Still, even the fact that her hands were immobilized added to everything a little, she felt more vulnerable and feminine than ever before in her life, totally helpless, and yet she trusted him not to hurt her anymore. In fact, it was even making sense in her head that he'd only done it to make her understand that she had been bad, and now that she had taken her punishment it was all over and she wouldn't have to pay for it ever again.

He could feel her body responding to him, and a feeling of triumph rushed through him that this girl, who probably would have never dated him, was now in his arms and willingly moving in rhythm with him. Her eyes were closed, and her face was full of the pleasure she was feeling. Moving more strongly in her, he began building her climax skillfully, slowly allowing her to override every part of her that felt pain as the pleasure in her pussy built higher and higher. Finally, as her body arched beneath him and she cried out her pleasure behind the gag, he swept both her legs over his shoulders; continuing to pump his dick in and out of her as she rode out the climax, he pulled the plug from her ass. Despite the slight pain from having her ass stretched out over the monster again, the sensation really only added to the climax as another part of her body was able to finally relax. Slowly Allison drifted down from her orgasm, Todd till pumping steadily away at her pussy.

Seeing that she'd gotten her pleasure, he pulled his dick from her pussy, and pushed it into her widely stretched ass. It wasn't as tight since the plug had been in it all evening, but neither did it cause her any pain. Moving quickly and roughly, he pummeled her ass hard, finally letting himself go with the pleasure of it. Since her asshole hadn't taken anything other than the plug, he was free to use it almost brutally. Allison was lost in her haze of pleasure still, barely noticing that her legs were spread over her shoulders, or that Todd was burying himself balls deep in her ass. Really, it mostly just felt pleasant, even though some of the discomfort was returning to her pussy and her breasts.

Todd groaned as he fucked her ass, the hours of tormenting her, and then holding onto his control while in her pussy had taken its toll on him. His balls were bursting with need, and he finally thrust hard one last time, burying himself deep in her ass as jet after jet of his boiling cum shot into the darkness. It felt like he came forever, the biggest load of his life planted deep in her ass, and slowly he relaxed on top of her sore body, completely spent.

Uncuffing her, he kept his dick buried in her ass, liking the knowledge that it was there and that she hadn't protested at all. When her arms were released, to his surprise they settled around his shoulders, although he did realize that this was probably the most comfortable position for him as he was still lying prone on top of her.

"Good girl," he whispered into her ear, and felt her sigh happily beneath him. Pulling back a little, he popped the gag out of her mouth and pulled it off her head before giving her a gentle kiss. Groaning, he pulled his dick from her ass with a small plopping sound. Moving very gingerly, she gathered herself up off the bed and got her coat. He smiled as he watched, she was walking funny again.

Decently covered, although it obviously hurt where her coat brushed against her chest, she walked to the door and turned to look at him. For a moment it looked like she was going to say something, but then she just nodded her head in a kind of farewell and left.

When Allison got home, she discovered that she didn't even want to think about masturbating, her body was far too sore. Even though it was only 10pm - it felt like she'd been at his apartment for forever - she fell into bed and went straight to sleep, still wrapped in her coat. As she slept, Todd's cum slowly began leaking from her ass.