The rest of the chapter. First section is located here.
She hesitated for only a moment, before acquiescing and leaning forward over the edge of the mattress, her hips hiked up by the four extra fluffy pillows. It was a position she was very familiar with as of recent, for both spankings and sex, and if it weren't for the bag of butt beating toys besides her she might have had hope that he had plans to fuck her. She heard him rummaging around next her, and her mind went wild with possibilites, all painful for her. She was surprised however to see him pull the vibrator from the bag. She was even more surprised when he plugged it in, then placed the wand next to her head.
"Take that, and place it between your legs" he commanded.
Lexi blinked at him, wondering if she had somehow misheard. But not wanting to look a gift horse in the mouth, she reached over and grabbed the vibrator, threading her arm under her chest and hips to rest the head of it against her slit. She could already feel the anticipation building as the Pavlovian response started to ripple through her.
"We're going to play a game" Caleb said behind her. "I am going to spank you with a variety of implements, and you are going to lay there and take it. Your only job is to hold that vibrator to your clit. You are to do so until you get close to the edge, and then you are to remove it until the feeling subsides. When it's safe, you put it back to your clit. If you can go the full duration of this without having an accident, I'll give you another chance at earning a real orgasm. You accidentally go over, and I will go get the cane from the car and leave your ass with welts from top to bottom. Do you understand?"
Lexi could hear her heartbeat thumping in her ears. She wasn't sure she had the self restraint to stop herself from tipping over the edge, especially with how sensitive her body currently was. But she absolutely did not want a run in with the cane, and she was determined to prove herself to Caleb. She nodded and laid her head on the blanket beneath her.
"Yes, sir" she whispered.
"Good. Turn the vibrator on, and we'll begin."
She dug down deep, trying to dredge up all the courage she could muster. Then she pressed on the switch, and the vibrator turned on with a loud hum.
Instantly, Lexi saw stars. The vibrations pulsed through her whole body and reverberated through her nervous system like lightning. She bit her lip and suppressed a moan, only for a hiss to escape instead as something heavy thudded against her ass. Without looking, it felt like some sort of paddle. He was really out to make her feel it tonight.
Six swats fell in total across her butt, and Lexi had to quickly pull the vibrator away from her clit by the last stroke. The pain of the paddling blended perfectly with the electric pleasure of the toy between her legs, and the edge came upon her far too quickly. She groaned as she realized the full extent of Caleb's sadism. Rather than being a feeling to be chased, he had turned her orgasm, the object of her desire, into the thing to be avoided. In order to earn a chance at it later, she must deny herself now, no matter how much she wanted it.
A new sensation shook her from her thoughts, this time sharp, stinging, and snappy. The riding crop, if she had to guess. In opposition to the paddle, Caleb struck her rapidly, peppering her behind with quick snaps of the wrist. The small leather head cracked against skin again and again in quick succession, and reignited the sting of her warm up hand spanking within a minute. She quickly had to pull the vibrator away again as the second minute of the crop continued. Her body was a raw nerve in the best and worst way, and it only took the slightest amount of stimulation to bring her to the brink. She listened to the toy buzz in open air as he continued to swat her ass mercilessly.
After three full minutes of the riding crop, Caleb switched to the tawse. As the leather whistled through the air and cracked against her ass, Lexi started to have an almost out of body experience. No longer did she feel each individual stroke of the implement, nor did she recognize how much time had passed between edges. Her world had begun to blur together in an intoxicating mixture of pleasure and pain. Riding the edge of her orgasm was her only concern. Though she still had the wherewithal to pull the vibrator away from her clit upon feeling the point of no return creep close, she became deafened to the rest of the world.
The implements started to pile up on the bed next to her. After the tawse, another paddle, and then a rubber flogger were put to use on her rear end. She could only imagine how battered her ass must look. Finally, the spankings stopped. Lexi gradually became aware of her own strained breaths and whines as her hips humped the air uselessly, the toy once again removed from her pussy. Caleb sat down next to her and brushed her loose, sweaty hair from her face.
"You've taken quite the whipping, sweetheart" he said, exertion in his own voice. "And yet to my knowledge, you haven't tipped over the edge once. Is that right?"
Lexi breathed deep, the buzz still rattling through her. "Yes... sir."
"Then I think it's time for your second chance at an orgasm" he said cheerfully. He rubbed her ass, and Lexi had to bite the blanket. She was much more sensitive than she realized back there, he must've really done a number on her.
"You have two minutes to cum using that vibrator" he explained, setting another timer on his phone. "That's not much time, but with the state you're in, I think you can do it. Is that right?"
She nodded her agreement with much enthusiasm. "Yes sir, thank you sir" she exhaled graciously.
"You're very much welcome. Your time starts now."
He pressed the button on his phone, and Lexi wasted no time in pushing the head of the wand against herself with full force. Her clit had become overstimulated through the constant edges, and she had to grit her teeth against the pain that wracked her body as the vibrations shook her body and soul. She wasn't concerned with the time whatsoever, she just needed to tip over the edge. And it was so close, she could feel it coming...
Suddenly, the sensations ceased as the wand fell silent. Lexi was snapped back to reality and frantically looked around the room. Caleb had unplugged the vibrator and was looking at his phone, the timer still ticking away.
"What are you doing?" she asked, her voice a strained whimper.
"Don't worry about me" he replied, flashing the phone screen at her. "You've got less than forty seconds left, better make them count."
Her mouth hung open incredulously. "Please sir, plug it back in" she begged.
"I will do no such thing" he replied tersely. "And you are about to run out of time."
Lexi groaned, and started to rub the wand against herself again. But she knew it was no use. A few moments passed, and the loud ringing of the phone filled the room.
"And it looks like time is up" Caleb noted, sounding fully disinterested. "It looks like you didn't want it enough. I'm sorry."
A frustrated sob tore itself free from Lexi's chest. She wanted, no, needed to cum. Never in her life did she need release this badly. She turned towards Caleb with pleading eyes.
“Please, you said I could…” she panted, fruitlessly rubbing the inert wand over her clit.
“I said that you would have the opportunity, not that you would” Caleb corrected her. “And I have given you ample opportunity. In fact, I'll allow you to keep rubbing if you want. You can still cum, if you can manage it.”
“I can’t…” she whined. There was no use with the vibrator unplugged. She looked over her shoulder at him with wide, pleading eyes. “Please give me one more chance.”
Caleb looked thoughtful, almost indifferent, but the bulge of his cock within his boxers betrayed his interest in her predicament. “I suppose you’ve been a good girl so far tonight. After all, you could have ignored my command and came at any time on that vibrator, but you followed directions admirably.”
His eyes trailed down to her rear end, and a small smile creeped across his lips. “I suppose I’m not quite done with you myself. I’ve been waiting to fuck you all night. Is that something you want?”
She nodded her head into the comforter. “Yes sir, please fuck me.”
“Are you sure?” he questioned. “Be careful what you ask for. I told you that you would earn your orgasm tonight. It might not be as easy as you think…”
Lexi groan and rolled her hips, her frustration and need to cum boiling to the surface. “Caleb please, I need it…”
He shrugged his shoulders. “Alright. Face forward, and put your head down.”
Excitement and hope filled her chest. She dropped the vibrator to the floor with a clatter. Her hips continued to move on their own, gyrating as if still rubbing against the wand. She heard him moving around behind her, shifting through his bag once move. A strange squeezing noise caught her ear, but Lexi didn't care what he was doing, as long as she got to cum.
Suddenly, a cold and wet finger slid between her cheeks and up her ass. Lexi gasped at the sudden sensation and tried to twist, only to have Caleb’s other hand push her back over the mattress and hold her there. Her mind went fuzzy as his intention became crystal clear.
“Caleb please…” she whined, thumping her foot against the ground in token resistance. He wanted to fuck her ass. She had experimented with small butt plugs in the past, but had been too embarrassed to try anything more. It somehow felt more indecent, more invasive than the things she was usually into. She hadn’t considered it an option for Caleb until this very moment.
“Oh, don’t be so dramatic” he chided, his slick finger casually intruding her back door, stretching her and spreading the lubricant within. “You just asked to be fucked. I simply didn’t specify how I would do it.”
Lexi groaned again, not liking how easily her body was warming to his probing finger. “Please sir, not my ass” she panted, fighting the roiling sensations within her.
“Why, afraid you’ll like it a little too much?” he joked. Then his voice turned serious. “If you really don’t want me to, I won’t. I can stroke myself to completion and be done for the night. But this is your final chance to cum. And I’m not open to negotiating. You can either take it up the ass like a good girl, or I can put you to bed with no orgasm. Which is it gonna be?”
Lexi bit her tongue and tried to contemplate the choice, but she feared her body had already made it for her. She was already starting to crave more than just his finger, and the constant edging had her in a truly desperate state. Her inhibitions were thoroughly stripped from her at this point, it was foolish to try to cling to them still. As was denying that a small part of her was growing deeply curious.
“Okay” she spoke quietly into the bed.
“I’m sorry, I didn’t hear you” Caleb replied. His finger crooked inside her, and she gasped.
“Okay!”
“Okay what?” he pushed. “What do you want?”
“I want you to fuck me” she answered quickly.
“And how do you want me to do that?”
Lexi looked forward and bit down on the last remaining vestiges of her pride. “In my ass, sir…”
“Now put it all together, and sound like you mean it. Otherwise, I’ll have to assume you’re lying, and we’ll have to stop.”
She breathed deeply, growing impatient. “Please fuck my ass, sir…. I need it.”
She heard Caleb’s smirk. “Well I’d be happy to!” he said in mock surprise.
His finger slipped from her ass, and she heard his boxers hit the floor. A squelching sound as more lube was squirted into his palm. Finally, his voice barking a command.
“Spread your cheeks.”
Lexi braced herself. Reaching back, she winced as her hands grab hold of her battered ass and parted herself for him. Caleb wasted no time, moving behind her and pushing his tip against her anus. A pang of worry shot through her chest. What was pressed against her was a fair bit larger than his fingers or a small plug. He placed one hand back on the small of her back, the other gripped and steadied his shaft in place.
“Now I’ve been wanting to do this for quite a long time, so forgive me, but I’m not going to go easy on you. You have until I finish to cum yourself. If you can’t, that’s it for the night. Do you understand?”
“Yes sir” she replied quickly. She was still so close to the edge from the vibrator and his exploring finger. But the longer he waited before starting, the greater the odds that her chance at an orgasm would drift out of reach.
“Good girl.” Then his voice softened for a brief moment. “If it’s too much for you, remember that you can safeword.”
With no further preamble, Caleb lined himself up, took a deep breath, and pushed into her.
Lexi was grateful for the slight warm up he had given her, as well as the lube. Caleb’s dick slid into her ass without a terrible amount of fuss or friction. But that didn’t mean that her body was completely ready to take him comfortably, and she felt herself gritting her teeth and clenching as her ass stretched with a dull throb to accommodate him. He gave her the briefest of moments for her body to relax. Then his hips pulled back slightly, and thrusted forward as he began to fuck her.
The dull throb sharpened as he pumped into her over and over. Caleb was not lying when he said he wouldn’t be gentle. She could hear his grunts and groans as he took his pleasure from her roughly. Her hands let go of her cheeks and dug into the blanket surrounding her. She couldn’t help but gasp into the bed as he drove his length into her repeatedly.
And yet, her body began to respond embarrassing fast. Warmth started to spread through her at a rapid pace, and the uncomfortable tightness quickly grew into a frantic need for more as she became accustomed to the feeling. If she hadn’t been so thoroughly teased and denied throughout the night, she probably wouldn’t have melted so easily. But even frustratingly empty, her pussy pulsed and ached with every thrust. She could hear her own wanton moans echo through the room and mix with Caleb’s voice in a lurid cacophony.
“Fuck, you feel so good” he half moaned as he pushed deep inside her. “I hope you’re enjoying this, because I might not last very long.”
“Please…” she groaned, her mind utterly lost to the sensations of her body. “I’m so close…”
“Then you better be quick” he threatened breathlessly.
His hands gripped tightly into her back, almost possessively as her fucked her. His weight shifted more onto her as his pace increased, pushing her even further into the mattress. It was in that moment, effectively pinned to the bed as Caleb’s hips slammed into her bruised bottom as he fucked her ass, that Lexi realized just how much she was at his mercy, and how much she had welcomed it. He was going to use her as he saw fit for his own enjoyment, until it was enough to satiate him. Her own pleasure was purely incidental. Right not, she utterly belonged to him. If the rest of the night didn't prove it, this certainly did.
The orgasm quickly crashed over Lexi like a tsunami. A guttural moan ripped through the air as she bit into the comforter, her ass squeezing Caleb’s cock as her empty pussy pulsed and contracted with pleasure. She gripped tightly to the blanket for dear life as the ripples cascaded through her overstimulated body. In a foggy haze, she was aware that Caleb was speaking to her, but words were meaningless to her at the moment. She laid there spasming, feeling Caleb’s movements grow more frantic over the course of a minute. Suddenly, he thrusted hard three times and buried himself in her, shuddering as his own orgasm came.
The bedroom was suddenly quiet for the first time in over a half hour. Over the course of a few minutes, Lexi gradually came back to her senses, feeling the delicious soreness of her body all at once. Caleb had pulled himself from her and was laying to her left, looking at her with a hint of worry. It was then she realized that her cheeks were damp. At some point in the final stretch, she must’ve shed tears.
“You okay?” he asked seriously, his eyes studying her carefully. It appeared that the normal Caleb had returned, if he had ever really disappeared.
Lexi nodded. “Yeah, I’m good. Was just a lot.”
His eyes softened. “Did it live up to your expectations?”
She chuckled weakly, trying to wipe her face on the blanket. Her entire body felt heavy, her ass ached inside and out. She was a bit of a mess at the moment, yet felt nothing but exhausted euphoria.
“For the most part” she said. “Probably not something I’d want every time, but it was… interesting.”
Caleb nodded in return, then pulled her slightly towards himself and ghosted a kiss across the top of her head. Her stomach and nerves fluttered at the sudden display of affection. She wasn’t ignorant to his feelings towards her, but she hadn’t yet sorted out her own feelings on their complicated situation. But as quickly as it had came, the moment passed, and Caleb rolled onto his back next to her, staring absentmindedly at the ceiling.
Suddenly Lexi felt very self conscious. “Sorry I kept you up so late, you probably have work tomorrow too. We probably could’ve picked a better day” she found herself saying, looking into the inky darkness outside the window.
“I do, but it’s only a little past 9, believe it or not” he smiled.
Lexi turned her head to glance blearily at the digital clock next to the bed. “Dude, I’m so out of it at the moment.”
Caleb pulled her a bit closer. “With your week so far and what I just put you through, I can imagine. Don’t worry, I just need a few moments to gather myself and clean up, and then I’ll leave you to getting some well needed rest.”
She turned to face the comforter again. “You can stay if you want. I don’t want to just kick you out after all of… that. Just try not to wake me up when you leave in the morning.”
“A fair request” he agreed. “I guess I’ll stay. Plus, we can go for round two once you recover.”
“Yeah…. let’s not get too ahead of ourselves, now. I don’t know how I’m gonna sit or even stand tomorrow as it is” she rubbed her scalded bottom with a wince.
She heard Caleb chuckle apologetically. “Yeah, I may have gotten a bit carried away.” She felt him sit up next to her. “For what it’s worth, I’ll go get the anti-brushing cream. That might help with the worst of it.”
Lexi started to whine; as ridiculous as it sounded, she was always embarrassed when he applied it to her, and he always insisted on being the one to do it. But she was swiftly cut off by a playful swat to her rear end.
“Remember, as long as I’m here, I’m still in charge. I’m going to get the cream, and we are going to apply it now. Unless you want to go back over my knee first” he threatened.
She sighed in defeat. “No sir…” she grumbled.
She heard Caleb hum in contentment, then get and leave the room, heading towards the restroom.
For a moment, Lexi reflected on how absurd it was to be embarrassed by such a simple thing as him rubbing cream into her butt. After all, she had much more valid things to be embarrassed about tonight. She felt her cheeks flush hot as she mentally cataloged the events of the night.
She had offered herself body and mind to him freely, and he certainly did his job in bringing her curiosity to life. She had debased herself for his amusement; it was a bit mortifying when she really thought about it. But her and Caleb had an understanding, one that superseded any temporary embarrassment. They shared a wavelength, and though she didn’t know how to define it, Lexi knew that he would never hold her desires against her. He certainly knew how to match her energy, as the throbbing of her rear end made perfectly clear.
So she stretched out on the bed and relaxed her aching body, waiting for Caleb’s return. She knew that the rest of the week would likely suck as much as the first half. But at least for a night, she could sleep soundly with not a care in the world. And what if tonight was just the beginning, she thought with a smile. After all, she had plenty of kinky fantasies within Caleb's area of expertise. Now that she had fulfilled one of them, who's to say they couldn't fulfill others? She grinned, thoughts of her week completely forgotten, replaced with the multitudes of ideas she could bring to life with him.