A Purchased Evening Pt. 02

"Perfect," he said, stepping away and she could see him pick up the same flogger he used before, seeing him disappear behind the stocks. She heard his footsteps stop and he spoke again... "How old are you, slut?"

"Eighteen, sir," she answered promptly. She felt his free hand slide down over her ass, being gentle but still enjoying the feel of her skin against his hand.

"Then nineteen it is," he said, laughing a little. "One to grow on. And you're gonna count each one for me, slut. Lose count and we start over, understand?"

She blushed now, hearing him call her by the pet-name again. "Yes, sir," she said, obediently, trying to brace herself for what was coming. She felt his hand slip off her ass and heard him step back.

He raised the flogger behind him, and slammed it down across her ass cheeks, making sure to catch both of them under the falls. He heard her gasp, making his still-soft cock throb a little in pleasure as he saw the skin darken across her ass. "One," she said quietly.

His hand came down firmly on one of her ass cheeks, making her left ass cheek burn a little deeper. "One what, slut?"

"One, sir," she corrected, gritting her teeth as he raised the flogger again, trying to edge down a little towards where her ass met her thighs and letting the flogger come down again, a little harder this time.

She squealed as the flogger landed, feeling her ass burn as the flogger fell away. "Two, sir," she counted, squeezing the bar between her hands tight as she braced herself for the next.

He waited a second, trying to catch her off-guard. He saw her hands loosen slightly around the bar and let the flogger fly, trying to spread the falls out as he arced it towards her ass, the slap of the leather hitting her ass making her squeal again.

"Three, sir," she counted, panting slightly, her ass starting to squirm as the burn of the flogger spread across her ass cheeks again. She could already feel her pussy getting wet, she had always loved getting spanked but this was taking it to another level.

He arced the flogger up and down again, edging upwards towards her waist, trying to space the blows out. She bit off a scream this time, feeling some of the falls land on her lower back, but managed to count out, "Four, sir."

He let the flogger fly again, this time right across the meatiest part of her ass. She squealed again, panting heavily but managed to continue her count. "Five, sir," she said, somewhat breathless.

He stopped for a moment, reaching down with his free hand to slide a finger through her pussy lips, teasing her for a moment with just the skin of his finger touching her before he managed to plow it inside her. "Jesus, you're already wet, aren't you, slut?" He laughed, letting her feel his finger inside her, gently rubbing it against the walls of her pussy.

She moaned, her pussy eagerly accepting the attention from his finger. "Yes, Sir," she managed to pant out. "You treat me just right, sir," she added, wiggling her ass at him, whimpering in surprise as he withdrew his finger.

He arced the flogger again, letting it come down across her ass with a little more force this time, another squeal escaping her before she counted off, "Six, sir,"

"You know, Slut," he said pointedly, "my aim is for you to have trouble walking tomorrow," he said, raising the flogger again, letting it fly and land across her ass again.

"Seven, sir," she said, blushing deeply as he continued using his new pet-name for her. He raised the flogger and let it fly again, trying to catch the top of her legs with it this time. She screamed in surprise, panting deeply, but managed to count out, "Eight, sir," she said.

"I'm gonna fuck that pussy again, it felt too good for me to turn that down," he said, a smile in his voice as he raised the flogger and let it fall, her squeal turning into a moan as her ass continued to burn. "Nine, sir," she managed to count, panting heavily.

"But I think," he said, "first, I need to get my dick in that ass of yours. Think that will work slut?" He asked, letting the whip fall across her ass again. "To make you have issues walking tomorrow?"

She squealed as the flogger hit her ass again, her pussy throbbing now. She kept shifting her weight back and forth trying to rub her ass against something, anything to reduce the burn, but could only feel air behind her. "Ten, sir, and yes, I think you may have already succeeded in that, sir." She added.

He laughed, letting his hand slip over her pussy, feeling the moisture already leaking from her cunt. "No, I think all we've achieved so far is you having issues SITTING tomorrow, although we still have some progress to make on that front, too." He removed his hand without touching her clit and slipped two fingers inside her, making her groan. "Fuck, slut, I think you're wetter now than after I fucked you earlier. Are you sure you cleaned yourself up?"

"Yes, sir," she said, moaning softly as her ass burned with no relief. She whimpered as he finally withdrew his fingers again, surprising herself as she let her head hang down. "Whip me, Sir," she begged softly.

He obliged, stepping back again and letting the flogger fly, harder now, giving her punishment strokes with the whip as he watched the redness deepen on her ass.

"Eleven, sir," she counted, whimpering softly as the next blow landed. "Twelve, sir," she continued.

He paused to rub his hand over her ass softly, surprised as she pushed her ass back against him. She groaned as she felt the skin of his hand pressing into her burning red ass cheek, enjoying the gentle attention in between the whipping.

He caressed her ass for a moment, marvelling at how firm it was, how smooth her skin was across her ass, even after the whippings she had received. He finally stepped back and let another stroke fly, this time hitting just the left ass cheek.

She screamed with the impact, gritting her teeth for a moment before counting out, "Thirteen, Sir." He didn't waste any time, letting the flogger fly again, this time on the right side. "Fourteen, sir," she counted out after cutting off her scream.

He raised it again, letting the flogger land across both ass cheeks, waiting for her to count out, "Fifteen, sir." She was moaning almost continuously now. He reached down and didn't even tease her this time, slipping the same two fingers back into her cunt, letting them sink in until he was knuckles deep. He twisted them inside her, back and forth, hearing her breathing quicken as he explored her pussy with his fingers.

"Oh fuck," she cried, feeling his fingers fill her pussy, feeling them twist inside her. It didn't last long enough for her liking, whimpering as they were removed. She barely had time to brace herself for the next blow, squealing before counting out, "Sixteen, Sir."

"Tell me what's gonna happen next, after this whipping, slut," he said, raising the flogger again and letting it fly, landing across both ass cheeks, her cry filling the room for a moment.

"Seventeen, Sir," she managed, panting heavily still. "And you're gonna fuck my asshole, Sir, roughly," she added.

"Quite right," he said, sliding his hand in between her ass cheeks, giving a gentle tug on the buttplug that was still embedded in her asshole. "I do suppose that means this will need to come out in a moment," he said, "But not yet," he added, letting the flogger fly again.

She cried out again, her cry settling into her near-constant moan again... "Eighteen sir," she said. "May I cum, Sir?"

His eyebrows raised in surprise. "You're asking to cum? From being whipped?" he said with surprise.

"Yes, sir, please," she was begging. He shrugged his shoulders.

"If you can cum from being whipped, more power to you," he said, his hand drifting in between her ass cheeks and tugging on the buttplug again. "Let's get this out of you," he said, "still holding the flogger in hand as he pulled backwards on the toy, feeling it resist him before finally slipping out of her asshole, leaving her a little stretched as it exited her ass. He quickly used his free hand to bring the flogger down over her ass, trying to time it so the blow landed as soon as his hand was free of her ass.

She immediately convulsed, locked in place in the stocks but he heard her cry out deeply, able to watch as she came from the removal of the plug and subsequent whipping. He could see it running down her leg as she purred and whimpered, letting her enjoy her orgasm.

As she was coming down, he walked the buttplug over and set it down on a table directly in front of her, so she could see it. "That was pretty impressive, slut," he said. "So impressive I'm willing to forgive the fact you didn't count out number nineteen."

"Thank you, sir," she managed. He turned around to face her, his cock harder now from enjoying the whipping he just gave her. He stepped up to her face, pointing his cock at her mouth.

"Lube me, slut," he said, pushing his cock against her lips.

She opened obediently, eagerly sucking on his cock, whimpering a little because he was only giving her the front half of it. She tried leaning forward as much as she could, feeling the tug on her wrists and shoulders that told her she was as far forward as she was gonna get.

He moaned as her mouth wrapped around his cock, watching as she struggled to take more of it. He kept himself pulled back a little, wanting to enjoy her oral skills for a moment before he finally withdrew, his cock popping free of her mouth with a wet sound. He looked down and saw drool trailing down her chin. "Classy, slut," he laughed, picking up a bottle of real anal lube. "But I guess I am about to sodomize you, so I guess class is out the window, huh?" he said, moving around behind her.

She hissed as she felt the cold lube trailing down between her ass cheeks, feeling it pool a little bit in her stretched anus. She tried to master her breathing as the lube settled onto her skin.

He applied the lube to his own cock as well, replacing the spit-lube she had left on him. He set the lube down, slipping a finger into her ass first to make sure it got into her sphincter to try to minimize friction inside her ass.

She squealed softly at the penetration, he could see her hips wriggling in the stocks as he lubed her asshole, getting her ass ready for his cock. He enjoyed listening to her enjoy herself, but he felt his cock throb as he began to pull his finger out, and he knew it was time.

He pressed the head of his cock against her stretched anus, not giving her any warning before starting to push it inside her. He gripped her hips and held her still while he pushed his cock forward slowly, letting her ass adjust to his girth as he tunneled inside her.

"God, slut, this is tighter than your pussy. I didn't even think that was possible," he said in admiration, finally feeling his cock bottom out, his balls tapping her pussy, making her whimper with need as he held himself fully in her ass.

She smiled at the feeling of fullness inside her, moaning again, before saying "I am a slut, sir, but my body isn't broken... yet, Sir." she added, squeezing her ass around his shaft for emphasis.

"Oh fuck," he said, quickly pulling back until just the head of his cock was in her ass. "You're not wrong, slut," he said, putting his hands on the top of the stocks for balance as he drove his cock forward again, burying himself inside her.

She squealed as he bottomed out again, the stocks vibrating from the thrust as he held himself steady against the wood frame. He began thrusting deeply into her ass, pulling back until he could just see the crown of his cock beginning to escape from her ass and then slamming it home again, building up a steady pace of deep strokes.

Lindsay's hands were grabbing the bar tightly as she got her asshole impaled. She was silently grateful for the bonds she was in because she didn't have to try and maintain her own balance. All she could really focus on anyway was the massive cock burying itself in her ass. She had to try and stay relaxed or this could be very painful.

She began whimpering as he fucked her ass, feeling her anus stretch and expand around him made her pussy throb, made all the worse because she could feel his cock burying inside her, millimeters away from her vaginal tunnel.

Matt began picking up speed, driving his dick deep in her ass as he let go of the wood frame and grabbed her hips, pulling her backwards to meet his dick in mid-stroke. She began squealing as her anus started becoming raw, the lube wearing away as he began to violently pound her asshole.

The violent thrusts had their intended effect a few minutes later, as Lindsay lost all control of her body, her pussy clamping down on itself and spasming in orgasm again. She cried out in pleasure as it washed over her, feeling her fluids running down her legs as she remained bound in place. Matt's thrusts were getting jerkier, and her orgasm seemed to speed him up.

A few minutes later, he buried his shaft in her ass, and let it stick there, using his hands on her hips to wiggle her around on his cock until he finally took one last stroke and felt himself empty inside her.

He groaned deeply, bracing one hand on the wood frame for support as he let his cock drain itself into Lindsays asshole. "Fuck, Slut, maybe i should change your name to Anal Orgasm Queen?"

She blushed, although he couldn't see it, saying nothing in response but squeezing his shaft with her ass, trying to rock her body back and forth on it to see if it had anything left. "Oh man," she said after a moment. "It's going soft," she said with a note of sadness in her voice.

He could feel it too, his cock returning to its natural semi-flaccid state. He pulled it free, eliciting a moan of protest as her abused asshole tried to return to its natural state. Stepping away from the frame, he reached down quickly to caress Lindsay's ass cheek, feeling its firmness again in his hand.

"Stay put, slut," he said, turning for the door. "I'm gonna go clean myself up real quick and then we can resume," he finished and bolted for the bathroom.

He left the doors open, and could hear her whimpering softly in the other room, recovering from the brutal ass-fucking he just gave her. He smiled and grabbed a cloth, got it wet and soaped it up and scrubbed his groin clean, trying to make sure he was as clean as possible for this final round.

Lindsay glared at the door as he left her bound. It took her a second to realize how badly her asshole was actually hurting right now, and the feeling made her whimper in pain. She wanted to massage herself a little, somehow try to soothe, well, something but was unable to, shackled in place as she was.

Satisfied, Matt quickly grabbed a bottle of skin care lotion and left the bathroom, slipping back into the room to meet her angry glare. He held up the bottle of lotion as a peace offering, opening it up and squirting some onto his hands, trying to warm it a little as he slipped around behind her.

His hands slid gently onto her ass, the lotion still cool but manageable. He was gentle but firm, squeezing and kneading her ass cheeks as the lotion soaked into the inflamed skin of her ass. She began to moan softly, feeling her ass cheeks starting to feel better after being soothed with lotion.

He didn't miss the moans she was making. "You have such a beautiful ass, slut. True, it may not be the biggest one I've ever seen, but I love how it feels under my hands. Soft yet firm, and you took my dick like a champ, so I definitely have no complaints," he said, squirting a little more lotion onto his hands and letting her enjoy the feeling of his hands on her, working to soothe the sting of the flogger she had withstood earlier.

Setting the lotion down, he moved around front and crouched down in front of her, studying her face for a minute. He finally ran one hand down over her cheek, lifting her head up to look at him.

"Do you remember what's next, slut?" he asked quietly.

"Yes, sir," she said quietly, meeting his eyes for now because she couldn't see his dick. "You wanted to cum in my mouth."

"Hmm... It is the only part of you I haven't came in yet," he said, "but we're getting a little ahead of ourselves," he finished. "I also told you I wanted to fuck that pussy again, it felt so good the last time and now I should be able to last longer to enjoy it more."

He stood, his half-hard cock hanging inches in front of her face. "But first I need a little help from you, slut," he said, indicating his dick. "Make me hard again," he commanded, pressing his dick forward towards her lips.

"Yes, sir," she said obediently, opening her mouth around him as he pushed inside, his cock immediately sliding into the back of her throat, making her gag slightly as she adjusted herself on his cock. She sealed her lips around the shaft and began sucking on him, letting him take as much of her mouth as he wanted.

His hands slid down into her hair, gently at first until he seized control of her head. He backed out until just the crown of his dick was in her mouth, letting himself groan in pleasure as she continued to suck on it before looking down at her. "Open your mouth, stick your tongue out," he commanded.

She obeyed, and he withdrew his cock for a moment to see the sight of her looking up at him, his dick inches from her lips with her tongue hanging out like a dog. "So pretty," he said. He moved his cock back onto her tongue, rubbing it against her tongue for a second. "Lick it, slut," he said quietly.

She heard him, and began trying to lick a complete circle around the crown of his cock, paying special attention to the underside of his cock. She could see he was fully hard now, and she wanted him inside her again. She tried to swallow his cock again but he pulled back before she could capture it.

"No, slut," he said, taking his dick away from her mouth. "It's time for me to really enjoy that tight pussy of yours," he finished, stepping around the wood frame and grasping her hips again. She wiggled her hips at him, making it harder for him to line himself up with her pussy.

He slapped her ass and said, "Quit squirming," waiting for her to stay still he finally was able to line himself up, rubbing the head of his dock along her slit, feeling it moisten against his head before finally pressing it against her opening.

She whimpered as she could feel the crown of his cock slowly pressing her apart, she tried wiggling her hips backwards, trying to capture more of his cock.

"You are a cock-hungry little slut, aren't you, Lindsay?" he asked with a smile, slipping just the head of it inside her pussy, letting her wriggle and squirm on it as he watched her petite body work to get more of his dick.

He could her the need in her voice... "Yes, sir," she moaned, "please fuck me, Sir," she asked, puncuating it with another twerk of her hips. He couldn't resist, and plunged inside of her, feeling her pussy expand perfectly around his cock. She moaned deeply as his cock filled her, gyrating against him as he fully seated his cock inside her.

Just as she was moving on him, he withdrew and slammed his cock home again, not giving her time to breathe this time before withdrawing and reinserting his cock this time, letting her feel her opening shrink down and then get expanded again as he slid back in.

He heard her squeal in pleasure with the reinsertion of his cock, and he began fucking her, grasping her hips for stability. He continued driving his cock home for several minutes, feeling the wood frame rattle against the floor as he fucked her.

He nearly came when her orgasm ripped through her, her pussy squeezed his shaft like it was holding on for dear life as she screamed out in ecstasy. He slowed a little, not wanting to get himself too close to finishing yet.