This story is entirely fictional and is in no way connected with the subject. This story contains adult material and is only suitable for people over the age of 18. If you are under 18 please stop reading now. All characters appearing in this work are fictitious. Any resemblance to real persons, living, dead, or undead, is purely coincidental. All characters portrayed in this story are over 18. Do not use this without my permission. (c) Copyright Viper_Noj 2002 onwards. Now, on with the story!

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This is the follow up to Billie Eilish - Debt Collection, which you can read here: https://celebritystorysite.com/index.php?topic=6294.0

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In the wake of her first encounter with Rob to try and settle her debts, Billie Eilish found herself stumbling into her place and locking the door, taking a deep breath before getting to her couch and sagging down. The adrenaline and endorphins of the whole experience had worn off with the chill of the night air around her and she felt absolutely exhausted.

Not just exhausted but sore as well. Her face was tender from the significant slaps she’d received and her jaw ached. Her throat was painful and she couldn’t swallow properly or even speak right, her voice breaking when she tried and she knew it was going to take days to recover. Despite their fuck being brief her pussy was aching as well, Rob having fucked her harder than just about any man in her life and the short but intense session left her legs shaking. She breathed deeply and tried not to fall asleep, knowing she needed to get in the shower.

She kept thinking about all that had happened in their time together, mind tumbling over how he’d taken her, made her choke on his cock until he broke her and then fucked her without mercy, then made her pass out when he finished with her. No men treated her that way and it pissed her off immensely that he’d done it and she’d let him, though she supposed the deal she’d made gave him the green light and there had been no illusions about what he wanted with her.

What pissed her off more was how wet it made her.

Billie felt so angry that her body had responded the way it has, like it had betrayed her and signalled that she was enjoying what he was doing even as she made clear to him she didn’t. Well, that wasn’t entirely true as she’d enjoyed the hard orgasm, begging him not to stop fucking her at that moment before she exploded, but otherwise she’d found it a humiliating and overwhelming experience. She grumbled to herself as she hauled herself off the sofa to make her way to the bathroom, knowing she needed to refresh herself.

To battle the aches she ran a bath instead, knowing the hot water would help relax and soothe her muscles. As the tub rapidly filled she stripped off her clothes, dispensing with the sexy underwear she’d worn to no avail with Rob showing little interest in anything besides getting his prize. Peeling her satin panties down and throwing them aside with the rest of her clothes, she stood and looked at herself in the mirror. Her phenomenal curves were there but now there was her exhaustion to go with it, tired eyes and redness to her face where he’s smacked her. Her tits also had red hand prints over them, a distinct mark of how he’d grabbed and groped her which made her pause...but also tingle a little. It signified ownership, dominance...and she privately admitted to herself she’d liked that.

She hadn’t appreciated how insanely rough he’d been though. It was well above what she’d expected and he’d worn her out, breaking her completely in the process. Billie thought how it was a side of him she’d never experienced or even suspected, never the slightest hint he could or would treat women, especially her, so powerfully, and that made her wonder as she turned the taps off and stepped into the hot, encompassing water. She shivered as she sank down into the bath and relaxed, letting her muscles unwind, feeling how tight they were in the aftermath of everything as she finally got them to properly give way.

She felt like she needed to sleep for a week.

Billie also felt something else – arousal. Giving a frustrated sigh, she hoped it would pass and she could just relax. It was because she knew what was causing it – Rob. Her mind was something that seemingly wasn’t so easily relaxed by the hot bath water and it was stuck on him and everything he’d done to her. She hadn’t been able to process it all at the time and instead was now replaying it all in her head, thinking over every slap and choke, every plunge of his cock into her body…and the huge, soul-shattering orgasm he’d driven her to with infuriating ease.

She ignored it and relaxed in the hot water, letting the sensation deep into her aching body. It was going to take days to recover, maybe longer, and she hoped he wouldn’t call on her again too soon as she needed a chance to be ready for it. His second time round, seemingly to finish off what he’d started with her, was liable to be even more intense and she knew she needed to bring her A-game to him otherwise he’d destroy her worse than he already had done. Dozing with her head back on the edge of the tub helped her unwind and she figured all she could do at that moment was try and recover.

But the arousal was still there and she knew it wasn’t going to fade. With an exasperated sigh she sank lower in the tub and spread her legs, sliding her fingers over her smoothly shaven pussy. She tingled immediately as the digits found the right spot and it took just a few seconds to get into the practiced routine, fingertips circling and pressing at her button as she let out a deep, ragged gasp. It was intense and powerful, more than she’d expected; in the back of her mind she hated that she needed to masturbate in the wake of what had transpired that evening and even more so because her mind was fixated on Rob and all the things he’d done to her. New, intense, overwhelming things...and part of her couldn’t wait to explore more of it his way, exactly as she’d agreed to.

The water splashed as she shook hard with a fast, intense climax, legs kicking some as the orgasm hit her like a train and made her jump. Her body jolted sharply, responding to her stimulation, exactly as she’d needed and the release was sudden but deeply satisfying. Her cry of pleasure echoed off the bathroom walls before she fell silent and sank back into the water, tingling in the wake of it.

“Fucking asshole,” she muttered, thinking of Rob, cursing how he’d made her orgasm again so intently. She didn’t know what it was since he’d treated her so roughly without a care for her enjoyment. Her face still stung from the slaps he’d given her...and she figured that was it. He’d treated her like no man ever had and it had awakened something deep inside her.

Still, she figured she didn’t have to let it out. Sure, she had to fuck him again to settle her legal situation as per their deal but she didn’t have to enjoy it or let on that he was turning her on. Billie figured it was a concern for another day and decided to try and just relax, to recover from the first session before she worried about anything else. In the wake of her orgasm she laid her head back and dozed off, body unwinding in the hot bath as it soothed her aches. Some of them at least as she knew others would take days to dissipate, such as the heavy one in her throat.

She got out of the bath and headed for bed, passing out almost immediately, sleeping nude and wrapping herself up as she crashed out.

The days passed silently. Rob didn’t contact her, no texts or calls, simply leaving her to it and she figured that was what their relationship was in the aftermath of what they’d done...or rather what he’d done to her. Still, despite how rough he’d been with her she was a little pissed he didn’t even bother to see how she was and he ignored her one attempt to make contact with a text that sat on read. It was only when she called him that he acknowledged her and that was only a simple conversation, where he needled her by reminding her that their deal had not been forgotten…unless she’d changed her mind and wanted to do it legally. It made her angrily have to protest that she wasn’t a quitter, a deal was a deal and she’d see it through as agreed...even if it did worry her.

The silence continued otherwise and it dragged through the following weekend, trailing to the tail end of the week, almost a fortnight since he’d fucked her. She’d recovered completely, her body feeling much better with every ache and pain gone, leaving her ready to fuck when he demanded it of her. She felt shame at admitting that, even if it was just to herself, but she knew she’d surrendered her body to him when she’d made the deal of her own volition.
She was almost giving up on him, thinking he’d leave her in limbo when her phone abruptly rang on Thursday night, her heart leaping when she saw it was him and figuring it was the moment.

“Hey, Rob,” she answered, trying to keep it casual.

“Hey, Billie,” he said, “how’s it going?”

“Pretty good, yourself?” she replied carefully, just waiting for whatever was coming.

“Good. What do you have planned for tomorrow night?” he asked.

“Tomorrow, nothing, why?” she said.

“Because I want you to get your ass round here again and pay up,” he said sternly, tone suddenly harder and more intense. Even though she was expecting it she was still caught somewhat by surprise. The way he could just turn on the dominant attitude threw her and she knew part of that was what turned her on given the way she tingled.

“I...yeah, sure, no problem I guess,” she mumbled quietly.

“It’s not a request, bitch,” he added, and she knew it wasn’t. At that moment he owned her.

“Yeah alright I got it!” she snapped back hotly, hating the way he spoke to her about it even though she’d agreed to it. There was a moment of silence before she filled it.

“So what, you want me to do anything? Any sexy underwear or anything?”

“Wear something sexy sure, it won’t be staying on long but if you want,” Rob replied.

“Want me to shave my pussy for you like last time?” she asked.

“Yeah, I do. Glad you learnt something from our first session,” he said and she could just hear him smiling, making her seethe.

“Yeah whatever,” she said to dismiss it, “this is the last time.”

“It’s the last time if you perform well enough, it’s gonna need to be better than last time to clear your debt,” he replied firmly.

“Hey fuck you, I did what you asked!” she snapped.

“You did what you could handle, you better bring your fucking A-game this time!”

“I’ll fucking bring it!” she shouted at the phone, “what time you wanna fuck me?”

“I’ll send you a message. You just think about this as you shave your pussy for me like a good girl,” he said and abruptly hung up, much the same as he had the first time they’d hooked up.

“Rob? Rob?! You fucking asshole!” she hissed to herself, throwing the phone aside as she stood up to pace around. She hated how he had her under the thumb, completely as his command and she just had to take it. Her anger bubbled impotently for a few minutes, then she sighed and stripped her top off, heading for her bathroom and the razor that would strip away her womanly hair and leave her smooth and ready for him.

As Billie was carefully shaving her pubic hair off to leave herself smooth as a china doll her phone vibrated. A glance told her it was him and she couldn’t help but pause her cautious efforts and take a look. She opened the message to the simple words telling her his place again at eight as it had been the first time, but there was also a photo of a wide black leather collar with “ANAL WHORE” emblazoned across it. A cold grip of adrenaline grabbed her and made her heart race, not knowing if he actually owned the collar or whether it was just a message, but either way it made clear what he had planned for her.

She breathed deeply to control herself and slow her heart, taking a moment before focusing back on her task. She rationalised that she couldn’t change the flow of things and he was in control so she had to go with that flow, but her pussy would be smooth as glass when he got hold of her the following night so she got on finishing the job.

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The following evening Billie looked in the mirror, pushing her long dark hair back from her face. She’d gotten ready even though he hadn’t asked for it, doing her make-up and squeezing her phenomenal curves into another sexy underwear set. This one was more racy than the last, with a sexier design of lace with more of a push-up to it, as if she needed it. She wore a thong and the sheer panels let him easily see she’d shaved as he wanted, her smooth pussy ready for him, if he even took the time before he stripped her naked. Either way it gave her more confidence and she’d covered it with her tight jeans and a simple top much as she had the first time.

Even though he was nearby she grabbed a taxi over to his place to make it easy, pausing outside to take a deep breath before she walked up the steps to his door and steeled herself. She knocked loudly, forcing down the nerves that rushed in her chest and made her heart pound. Billie told herself she was going to be confident, to handle it professionally and keep calm, that it was just another business deal and she’d done it before. She knew he was approaching the door and she fleetingly wondered what he had in store for her, but figured she’d find out imminently.

“Billie,” he said with that same infuriating smile he’d used on her the previous time, that one that let her know he loved the position he had her in.

“Rob,” she replied, walking past him as he held the door open for her. She walked down the hall as he locked the door intently behind her, trapping her in for her evening of submission and degradation.

“How have you been?” he asked, as if he cared. He had once, they’d been quite close friends, but she figured those days were over and were replaced with him using her as a fuck toy. Well, briefly at least.

“I’m good thanks, ready to go, how are you?”

“Glad to hear it,” he replied, “vodka’s in the kitchen.”

“You think you need to get me drunk for this?” she said, raising an eyebrow.

“No, I’m sure you’ve made your peace with what this deal is. I just figure you might wanna get yourself drunk to loosen up, like last time,” he said, his offer casual.

“I don’t care if you do or don’t, it’s up to you.”

“It won’t hurt,” she said after a pause, a hint of smile touching her lips as she flicked her eyebrow a touch. She turned and walked along to his kitchen, seeing the bottle and shot glasses on the counter already as he’d said.

“You want one?” she asked as she upcapped the bottle to pour.

“Yeah, go for it,” Rob said. Billie sloppily poured two doubles, right to the top of the glass and stood the bottle down. He grabbed it as she did, both of them holding up the shots.

“To settling this deal,” she said firmly, looking into his eyes.

“To seeing you work for it,” he replied, a rattlesnake smile on his face. They clinked the glasses then both necked the vodka, gulping it down. Rob just enjoyed it even as Billie shuddered, the intensity hitting her as he slid down her throat.

“Just the one?” he asked as he saw her holding onto her glass, contemplating it.

“It should be enough,” she said, pretending to restrain herself.

“Fuck it, why have enough when you can have plenty, I’m sure it’ll help,” he replied as he turned to leave the kitchen.

“This is the last time remember, we’re settling this,” she said, deciding to be bold and make her point. He paused and smiled at her, an arrogant smirk.

“That’s up to you. Don’t be a pussy and pass out this time, maybe we can get it done,” he replied, frustratingly, infuriatingly cool with her. It made her seethe, fingers trembling as her jaw clenched, having to hold her tongue as she knew what it would invite. Worse, she knew he was right.

“When you’re done, get upstairs,” he added, seeing her pause from picking the vodka up again, “and don’t make me come down and get you.”

The threat was clear, and she knew exactly what sort of treatment she could expect if she kept him waiting. He headed upstairs as she quickly poured another full glass of vodka, hands shaking a little as she brimmed it before standing it noisily aside again. She shoved the cap back on and then grabbed her glass, breathing hard before she gulped it down again, forcing it down in one go before she shuddered again. It was more intense second time around and she shook, grimacing a little at it even though she liked vodka.

She hauled in several deep, hard breaths to calm herself again, steeling herself for what was coming...aside from herself, slamming the glass down on the counter and then stalking intently to the hallway. Billie made her way up the stairs to his bedroom, walking in to find him ready and waiting for her. He was already naked, his toned body on display, dominant and prepared for her with his cock already semi-hard.

Billie contemplated a comment, a compliment more than anything as she did find it flattering he was already turned on and ready for her in anticipation but she thought better of it. Any lip from her she knew meant punishment and she figured she’d end up getting plenty throughout the evening so there was little point bringing it onto herself earlier than necessary.

“How do you want me?” she asked, wanting direction so she did exactly as he commanded while she threw her leather jacket off.

“Strip naked, like last time, no fuss,” he said firmly, that same dominant tone she’d heard previously cutting through and sending a tingle through her body that made her vagina squeeze in arousal.

“Got it,” she said quietly, reaching down for her blue top to peel it up over herself, making sure to extend her arms fully and stretch out to give him the best possible look at her tits in their sexy lace bra. He just stood and took her in as she threw it aside and undid her jeans, shoving them matter-of-factly down her legs and dragging them off her feet, kicking them over with the other clothes to leave her in her underwear.

“That’s nice,” he commented, taking in her sheer, lacy underwear and obedience with the razor. She stifled a smile, happy he was pleased with her but she resisted saying thanks. Rob hadn’t asked for it after all and she decided she was best to just do as she was told and get naked. He was pleased she didn’t slow even as he appreciated the sexy underwear, loving her thong as she turned away but also that she was following orders as she reached back to unclip the tight bra and let her magnificent tits out, shrugging it off and chucking it aside. It gave him a chance to see her gorgeous curves as she stood before him and reached to shove the panties down, stooping to drop them down her legs and leave her naked before him.

Shaved. Obedient. Waiting.

She was different this time around, Rob could sense it, she was going with the flow of it, resigned or into it he couldn’t tell but the result was the same, though he’d be interested to see how long it lasted as he pushed her. He grabbed the wide collar with “ANAL WHORE” emblazoned across it, the same one he’d sent her a photo of, and stepped forward to her holding it out. To his pleasure Billie reached up and grabbed her hair, sweeping her long mane up out the way for him to access her neck.

“Good girl,” he said, sliding the cool leather around her as she shivered a little, clearly nervous. He didn’t care however and slid it through the clasp, pulling it tightly as she winced and securing the buckle.

“Fuck, watch it,” she complained, realising her mistake the second she spoke, immediately met with a firm slap across the face.

“Don’t forget how this works, cunt,” he said sharply, the tone suddenly icy and hard. She grimaced as he slapped her across the other side of her face, mumbling in irritation and pain. It hit her harder than she remembered but she figured she wasn’t warmed up to it, it was all sudden and she’d thrust herself back into it. Two more sharp, stinging slaps caught her face, making her grumble and recoil.

“Ok, ok, yes sir,” she said, reminded what she was dealing with.

“Better.”

It was all he said as he grabbed her collar and yanked her forward, making the singer stumble as he pulled her to the bed, but it was what he did next that really caught her off guard. Still holding her collar, he swept down and shoved his arm between her legs, somehow effortlessly lifting her up and then fairly body slamming her down onto the bed as she gave a squeal. Billie could barely process it all as he grabbed her arms and dragged her to the edge even as her massive tits still bounced. He took it in with delight, spread out as a perfect fuck toy for him as he got her where he wanted her, her head sagging back off the side of the bed.

She knew exactly what he wanted and hardly had any time to protest as he grabbed his cock, fully hard now and ready for her, and dipped down to shove it straight into her waiting mouth. Billie mumbled in surprise as he drove it straight in and wasted no time going deep, his thick head plunging straight to the back of her throat. Gagging immediately, she choked around his cock as he held it there, body convulsing before him and jiggling perfectly before he pulled back and drove it in again firmly.

Billie knew she was going to get no chance to handle it and tried to just hang on, fingers digging into the bedding as she clung on and tried desperately to control herself. It wasn’t like their first time when she’s started the blowjob before he took full charge of her, not this time. She tried to suck and drive her tongue against him as she knew he’d want but she couldn’t co-ordinate herself, struggling to cope with it all as he thrust powerfully into her throat. Rob drove himself down hard, giving long, intense pushes into her to try and break through her resistance and sink his whole cock in as her feet kicked and twisted, unable to keep herself from moving.

His hand was hooked in her collar and she knew there was no escape, he wasn’t playing around as he held her in place and drove his prick into her mouth. Billie thought she was ready for it, prepared for what he was going to do to her but she wasn’t and found out at that moment. He was so rough and dominant, completely overwhelming her and it was only the start. Her mind had blocked out the worst of the previous session, his roughness fading in her memory as she simply recalled what had turned her on and how she’d performed fundamentally well for him, but all that was sharply recalled now as he got to work on her.

“Come on you cunt, swallow that cock,” he commanded, sending a shiver of anger through her even as her eyes streamed, head back over the edge of the bed for him, voluptuous body arching and straining as she choked noisily around his impaling cock. Her fingernails dug intently into the bed sheets as she hung on, bracing herself tightly to take his thrusts as he reached down to take hold of her head, keeping her exactly in the right position as he tried to force his thick cock her throat.

It seemed bigger than last time, his cock too much for her, retching helplessly over and over again as he pumped it relentlessly into her throat. He wasn’t going to stop, she knew that – he was simply waiting until her muscles got too tired to fight back and it let him slide right into her mouth. She couldn’t control her gag reflex, as much as she wanted to, wishing she could just get on with it and end the ab straining retches.

His hips pumped hard with deep, intense thrusts that buried his cock into the back of her throat. He was getting over half of it in but still straining against her resistance, forcing against it hard with strength and ambition and she knew it was only a matter of time. Rob just relished it as he drove his cock into her hard and heard her choke, saw the tears streaming from her eyes and the aching clenches of her muscles, her tummy tight above her smoothly shaved pussy. He loved that she did as she was told for him and he knew this time really was his moment to enjoy her, she was ready to go come hell or high water.

“Fuck,” he sighed as she retched particularly hard and pulled off him, turning her head to let a long, thick string of saliva slide out to the floor as she coughed hard, body shaking.

“Christ, I know you can do it, just get on with it would you!” he hissed with exasperation as he cradled the head of the choking singer.

“I can, I can!” she pleaded, knowing from their previous experience that it would happen, “just give me a chance”

“No.” he said commandingly, his tone deep and authoritative, making Billie tremble with arousal that she hated before he twisted her head back over and dipped down once more. His cock was harder than ever for her as he plunged it hard into the back of her throat again, no break or respite, expecting her to get straight back to it like he’d paid for it. He had, of course, which was why she’d agreed to this in the first place but it was at moments like that she wondered if it was the right choice.

Her body continued to deny him though she could feel the ache and tiredness, knowing her muscles couldn’t keep resisting. Rob loved how she was gradually tiring, feeling his thick head pushing deeper and deeper, just able to sense that increase in the stretch, knowing it was only a matter of time before the singer choked hard as he sank in properly.

Billie held out for another couple of agonising minutes, eyes screwed shut and watering, her body still heaving with her massive tits jiggling much to his enjoyment before that fateful moment. It had taken a little longer than the previous time but exactly as she’d told herself it had only been a matter of time and that instant had arrived. With one deep, powerful push her muscles couldn’t hold on and failed, completely exhausted, allowing her throat to expand fully for him and his thick, bulging head and rock hard shaft plunged down her throat. Rob didn’t waste the chance and made sure to lean on her hard so she took all of him until his balls pressed into her nose.

“Finally,” he commented as she heaved, holding her head tightly to keep her in place as she gagged and flexed around his impaling cock. It felt so thick and invading in her throat that she had no idea how it fitted. She’d done it before but it didn’t seem to prepare her as it felt so overwhelming and Rob wasted no time in letting her feel that, washed away by it all as he held her in place and forced it as deep as he could before pulling back slowly to let her feel every ridge and contour of his manhood while it slid from her throat.

It drew her choking cough with it but he cared little for her problems; with her throat broken in he swiftly drove back into her and ploughed his cock through her aching muscles and buried it deep once more with deliberate pace and power. It was all Billie could do to drag in a breath before her throat was blocked again, Rob holding himself deep once more to make her feel it and retch repeatedly. Tears streamed down her face and into her hair as he kept holding her right down, his balls pressed into her face as she desperately waited to breathe again, body straining and twisting painfully.

She knew her abs were going to ache again after this session, exactly as they had before, and she figured a few other things too. Their first session together, her first intense throat fuck had done little to prepare her and she dug her nails into the bedding to hold on and endure it. His cock pulsed rock hard, flexing powerfully in her mouth and she knew he was loving it exactly as he had the first time around and was enjoying settling their deal. Billie just tried to stay calm even as her body tensed and strained, twisting as she tried to hold down the aching, choking gag every time he drove deeply into her.

Her breaths came in sharp, wet gasps around him as he pulled back, grabbing what she could when she had the chance, drooling heavily around his cock as it pumped deeply into her throat. Despite her gags her body made precious little effort to resist him with her muscles exhausted and she just screwed her eyes shut as he held her tightly in place. Her fingers were white as she held onto the bed while Rob thrust his hips forward to bury his cock into her throat over and over again, balls shoving hard into her face every time. Saliva trailed thickly down her face and into her hair as she failed to control herself around him, tongue flailing pointlessly against him as she tried to keep licking at him.

She fleetingly hoped any additional stimulation might make her deep throating quicker, even though she knew that was ridiculous. Rob her demonstrated his excellent stamina with her previously and Billie already knew it was futile but she tried anyway. At the very least he might enjoy it. He was enjoying it anyway as he’d been looking forward to putting the curvy star through her paces again. Her throat was tight and convulsing, adding to the feel as he started to work his hips faster with good power, making sure she swallowed it fully every time.

He loved how submissive she was being, resigned to it underneath him as she contorted on the bed before him, not resisting even as her body primally struggled to handle it, letting him have control of her to do as he pleased. He reached down for a hard squeeze of her massive tits, struggling to get his hands around her as he compressed them in his hands and dug his fingers in until she let out a strained, pained squeak of protest. In return he laid smacks across her tits, a couple from each side to make her huge chest bounce as she mumbled, the sting spreading through her skin and reminding her what was surely to come.

With her body giving up the fight it became easier to fuck her throat and Rob started to plunge into her hard and fast, still using full strokes of his cock to let her feel every inch of it. Billie just mumbled and complained as he started pounding her, choking loudly as he pulled back and she tried to hungrily pull in breaths of air. Her head spun as she struggled and sputtered around his cock, feeling the hot drool sliding down her skin as she heaved on the bed, writhing and digging her heels into the sheets.

Rob was full of energy and adrenaline, absolutely loving it as he slammed himself into her and made her swallow it. He let himself get carried away with it and hammered on her to hear her choke the hardest she had so far, loving his dominance over her. He groped at her tits again, loving her feminine flesh as he squeezed it hard to make her writhe, pulling his fingers back to pinch her hard nipples intently so she jolted and cried out around his prick. He held her head, twisting her long hair in his fingers as he pumped her with deep, short strokes to keep himself deep in her as she struggled to breathe. Her heart pounded in her chest as she tried to handle it, knowing what she must look like.

His fucktoy. She looked exactly like his perfect, dominated fucktoy which was made for a perfect start, and Rob intended to keep it that way. With a flurry of fast, intense strokes he buried it deep in her throat and leaned on her, holding it deep for a few moments until Billie desperately flailed her hand to bat at him and signal her desperate need for oxygen. Still, he held it a couple of seconds longer before he wrenched back fast and out of her mouth, the sudden change making her surge and cough hard before she could get the breath she needed.

Rob left her gasping, prick rock hard as he leaned over and grabbed her ankle, using his impressive strength to haul her round on the bed where he wanted her. Billie just spun round on the sheets and sagged off the bed as she tried to clumsily keep control of herself, completely overwhelmed as she tried to catch her breath and focus. Rob was on top of it though and grabbed her under the arms, hauling her up powerfully to throw her back onto the bed with her ass at the edge, exactly where he wanted her.

“I thought you wanted my throat,” Billie mumbled, half complaining, half commenting. It was met with a firm slap across the face however, shutting her up as she winced, feeling the sting across her messy skin.

“Shut up, cunt. You’re mine and I get to do what I want, don’t forget that.”

She didn’t reply, and barely had time to as he yanked her legs up onto his shoulders then reached down for his thick, throbbing cock and buried it into her with one hard thrust. Billie cried out in a mixture of sensations, rasping at the pain as his head shoved against her cervix hard, body rippling with heat as the wetness of her pussy and the thick drool she’d put on his iron-hard cock helped him plough straight into her.

“Fucking whore, that went in like you were desperate for it,” he commented with a smile, looking down over the dominated musician. Billie’s eyes were screwed shut, body tight as she winced at the pain spiking the cacophony of sensations as his thick prick had slid inside her, sheets balled up in her fast as she tried to pull away. It was pointless of course as Rob had a tight hold of her and was leaning to keep his cock fully inside her so as to enjoy the tight, exquisite clench of her vagina. Rob then pulled back slowly before plunging inside her once more, body betraying her and letting him slam deeply again against her cervix.

“Ow!” she protested as the jolt of pain shot through her body, legs twitching in his grip as he kept her where he wanted her.

“That hurt, does it?”

“Yes!” she snapped in response, immediately met by a slap across the face that made her growl in suppressed rage as his hips started to pump his cock inside her.

“Fuck,” Billie grumbled, knowing she had to take it. Another slap caught her straight after to make her flinch, his rhythm unchanged, just hitting his stride perfectly even as he disciplined her.

“Yes what?” he demanded. She knew what he wanted to hear from her and she took a moment for a breath as her curvy body rocked beneath his deep, intent thrusts.

“Yes sir,” she said calmly, putting the pain aside to address him as she knew he wanted.

“Good girl,” he replied and she was ashamed as it made her shudder, biting her lip to keep from whimpering as she felt herself blush. Even if he didn’t see the colour to her cheeks she knew he’d feel the quiver and clench of her pussy as her muscles trembled and contracted around him. She hated that he had that effect on her, that being treated the way she was made her excited, that it pleased her to be so submissive to him when he was fucking her the way he was.

Rob picked up the pace a bit, more power that drove himself deep inside her and really gave her everything, his bulging head slamming into her cervix again with intensity that made her grimace with every thrust.

“Sir, do you have to be so rough?” she asked. Addressing him as her master felt strange but it was the only way she knew she could speak without further punishment, and she was wearing the collar he’d chosen for it. It seemed fitting.

“Do I have to be? No, of course not,” he replied, looking down over her as he continued to slam his prick deep, giving her a moment of hope that he might back off.

“Do I want to though? Absolutely.”

With that he slammed hard against her and held it deep as she winced again, pain stabbing at her momentarily as he showed his dominance and ownership over her. Billie just grunted but made no more complaints, knowing her place as she tried to just relax into it and let his cock drive into her, squeezing a little as he withdrew his thick shaft to stimulate him which she knew he’d appreciate. She tried to unwind and loosened her grip on the bedding, her muscles relaxing with a the tension draining intensely from her, realising how hard she’d been holding on. Yes it was set to be the hardest, most intense fuck she’d ever received but she knew Rob was going to take care of her to make sure she went all the way.

Rob could see her submission, knowing she’d given up fighting it and he smiled to himself, loving how she just resigned herself to his control. He held her legs and fucked her briskly with long, powerful strokes that made her body and massive tits shake beautifully. His hands held her legs tightly to keep her in place and let him plunge himself into her slick, hot pussy, loving that she was squeezing dutifully on him in the process. As she calmed down she opened her eyes, looking up to Rob over her as he used her carnally.

He looked down into her eyes, holding her gaze, and neither one of them broke away. Despite Rob being completely in charge, totally owning her body, she didn’t back down or look away, wanting to keep her focus on him. He obviously wasn’t going to give in and they settled into an easy, intimate moment together. Billie took in his looks and his physique with her peripheral vision, realising maybe she’d been missing out as he was certainly nothing to sneeze at and he was fucking her like no other man ever had.

Not that she was entirely sure as she grunted hard beneath him, heart pumping intently as his thick cock stretched her out and he drilled her deeply. His rock hard shaft drove in and out of her freshly shaved pussy, still staring into her eyes as he worked intently. Billie stared back up, lost to the moment, locked into it with him and so she took her hand from the bed and tentatively reached up for his as they held her thighs. She gently touched him, not wanting him to recoil or be tempted to discipline her for the move, intimate and close as it was.

He didn’t react, continuing to hold her where he wanted her and so, emboldened, she slid her fingers over his and held him around his hand, squeezing them tighter to hold her more intently. She wasn’t sure it was deliberate but she knew she was enforcing his ownership of her, his control. Billie was rather lost to it but Rob, whilst enjoying her submission to him and his dominance, was mostly enjoying that she was behaving and he was able to smash her snug, shaved pussy as hard as he liked.

Billie was enjoying it, much more than she should have been as he pounded on her, his big hard cock hitting places no other guys seemed to manage and, much like the first time, she felt the tingle of orgasm tremble through her. It brought her back to reality; she didn’t let go of him or look away but she blushed and bit her lip, not wanting to orgasm from him fucking her as she figured it sent the wrong message. She didn’t want to enjoy or encourage this, it was her paying off a debt and nothing more - but surely that didn’t mean she couldn’t enjoy it.

She did her best to hold it back but it was no use, that somehow only made it worse and the orgasm built rapidly until it was upon her, breaths turned to little moans of hunger and need as Rob pounded her pussy, giving her no break, only dipping a little to accentuate his pressure on her G-spot and bring on her climax sooner. Billie’s moans turned to hard, harsh cries for the few final moments, her hands leaving his at last as she slammed them back to the bed and dug her nails in right before it hit her.

“Oh fuck!” she shouted as she bucked hard, hips jumping on the bed and shoving into him as her vagina clenched hard, clamping down on his impaling prick though it barely slowed him. Rob kept hammering her even as she tightened intently, accentuating her peak as his cock kept slamming deeply inside her over and over. His pressure on her G-spot was maintained as he pounded himself into her and drove her orgasm ahead of him, Billie jolting and shaking under him as he gave her no chance and maximised the stimulation throughout until she gasped and tried to twist away as she was overwhelmed.

“Stop…” she gasped half-heartedly as she writhed under the nerve shredding tingles of his cock continuing to pound into her pussy as it loosened up again, the pleasure replaced by an overload of sensations. She knew she was his fuck toy, that he was her master for the night and it made her protest weak and non-committal...but it didn’t stop the punishment that she got for it. The slap landed firmly on her, much as she expected, but it still made her flinch and gasp, her pussy giving what she was sure was a very enjoyable clench on his impaling cock.

“No,” he said simply, his tone calm and dominant, in full control and it only made her shiver a little. She was angry at herself, that she was responding and even enjoying how he was treating her when all he was doing was using her as his personal fuck toy. Billie held on as Rob pumped her hard for another minute or two, taking time to have fun with her, using the full length of his cock before he abruptly pulled out of her.

Billie sighed as she let her legs flop down from where he’d held them, blood flowing back into them coolly while she wiggled her toes, getting a brief respite before Rob grabbed hold of her again. His motion was rapid and deliberate, almost sinister as he seized hold of her with intent and threw her over onto her front, higher on the bed and with power that made her tumble down onto the sheets.

She just breathed and looked back over her shoulder, flicking her messy hair aside as Rob slid onto the bed with her. His cock was sticking up rock hard and she assumed he’d mount her again to fuck her from behind, but instead he spanked her ass, the intensity making her jiggle and give a muffled cry of pain. He repeated it a couple of times, Billie keeping her composure through the pain before he slid his fingers inside her to her surprise. Given she’d already come she wasn’t expecting it, but she soon realised it wasn’t a nice G-spot massage or anything.

Two fingers were quickly replaced by three, working them into her yielding tunnel before he pulled back and added his little finger to press all four inside her. Billie grunted as he squeezed them all inside her, stretching her vagina tightly around his digits. It was a lot but she handled it, rolling her hips and helping his access as he drove them inside her slick, loosened pussy. He thrust them into her and built up a short rhythm for a moment, letting her feel how filling it was, stretching her in new ways for a moment as she gasped before he suddenly paused and added his other hand.

“Oh fuck, don’t, I can’t…” she started, cut off when he pushed forward and forced a total of six fingers inside her, stretching her intently as they immediately tested her limits. She was surprised as her vagina took them, easing over them as he powerfully pushed them inside and made her accommodate them. She growled at the sensation as her pussy was stretched in both directions by the size of his fingers.

“Fuck, take it easy!” she snapped, forgetting herself a moment as he shoved them inside her firmly. She was immediately regretful as he withdrew and grabbed her hair, wrenching her head back, slick fingers twisting in her long locks as he slapped her face, then rubbed his hand over her face to spread her slippery juices all over her face as she grimaced and let out a whimper of displeasure.

“Shut the fuck up, cunt!” he snapped loudly, shoving her head back down onto the bed, his hands releasing her and sliding straight back down to spread her ass, pulling her slick pussy open in the process. Billie just stayed silent as he resumed what he was doing, only this time he shoved all eight of his fingers to her...though she dared not complain even as he heart raced.

“Fuck…” she growled, grimacing as she struggled to stay silent while Rob forced both his hands forward and buried eight digits inside her. Her pussy stretched out around him as he overwhelmed her muscles and delved into her as she gave a squeak of pain, her vagina pushed wider than it ever had been before. She just clung to the bedding as Rob drove his hands deep, right up to his thumbs which he then used to press firmly on her asshole and force it open.

He used his thumbs to anchor himself, dug into her tightest hole as he rocked his hands to thrust all his fingers into her slick, stretched vagina. Billie growled at the intense mix of pain and pleasure, the stretch arousing with new nerve endings lighting up but she was pushed too far and it hurt, pussy stretched to the limits. Rob didn’t care however, simply using her how he pleased, how she’d agreed to, and thrust his fingers deeply inside her. He loved her muscles squeezing down on him, how her body gripped him in pleasure even as she complained, thrusting faster to build up a rhythm that soon her the singer grunting in enjoyment.

Billie found herself thrusting back into the near-fisting she was receiving; she figured it would please him for her to respond and invite it...and there was no denying it felt good even if her pussy was getting stretched way too far. He didn’t give long to enjoy it however, not seeing it through to another orgasm for her before he gave her a flurry of intense pumps and yanked his hands back to make her gasp. She blushed as he hooked his fingers into her entrance and stretched her open, wanting to see how wide he could get her for a moment.

“Cunt, only whores stretch like that,” he commented, sending a rush of anger through her but she knew better than to snap back at him over it.

“I’m your whore,” she breathed submissively, feeling a particularly firm smack on her round ass to follow it.

“You’re god damn right.”

His cock was iron-hard, standing up in front of him begging for Billie and he wasn’t going to deny himself. She was submissive and dutiful, evidently resigned to the agreement and intending to pay in full. He was resolved to make sure she did and intended to get all the mileage he could from her before they moved on with their lives. He spat thickly into his hand and slicked the bulging purple tip of his cock, grabbing his shaft to bend it down as he grabbed her ass and spread her wide again.


He loved how her pussy gaped as her tight asshole clenched up, instinctively squeezing before she relaxed again, a perfect target as he pushed his hips forward and lined himself up, getting ready before he leaned on her. He didn’t want to give her a chance so he took a moment to prepare and then went for it, grabbing himself tightly as his fingers dug into her flesh, pressing himself perfectly into her tightest hole and forcing his hips forward powerfully to stretch her over himself.

“Oh fuck! No, no…” Billie gasped even as he popped unceremoniously inside her, muscles unable to fight him as his thick head squeeze into her and he followed it up with several inches of his big cock. Her protests faded into a silent scream, eyes pricking with tears as the sharp, intense pain of her sphincter stretching around him overwhelmed her, waves of it wracking her body as she tensed hard under him.

“Oh yeah that’s tight,” he grinned, Billie hearing his little chuckle that followed it as he pinned her down and drove himself into her fighting body. She took a breath then let out a scream, rattling the windows as he used his bodyweight to press the last inches of himself inside her, making her take his thick prick all the way to the balls in her trembling asshole, making her the anal whore her collar designated.

“Fuck,” she winced, struggling to breathe as her heart raced, pounding behind her massive tits as he pinned her on the bed and pulled back slowly. Her body tried to squeeze him out but he didn’t allow it, knowing exactly what he was doing as he slid back before he plunged his hips down once more to plough it inside her.

“Fuck, I don’t like it,” she growled as he bottomed out again.

“I don’t care, I didn’t fuck your ass last time so I’m gonna do it now,” he replied, starting a rhythm as he pulled back again and forced himself into her once more, not giving her asshole a chance to reset and stretch out easily, stuck in spasm as he enjoyed every little clamp and clench on his prick.

“Take it easy at least,” she begged, regretting it immediately as a hard slap landed on her already stinging cheek to make her flinch.

“Shut up, cunt. It’s gonna get a lot tougher than this so you’d better suck it up,” he told her firmly, leaving her no doubts that it was about to be the hardest anal fuck of her life. He leaned on her shoulders to pin her down hard and pushed up, his weight pressing her to the bed and crushing her phenomenal rack as he took charge, hooking his feet over her legs to pull them wider and keep them there.

She was on her knees just a little, hips up in a perfect prone bone position and knew he had complete control. She had to give it to him anyway, but the fuck had been far more enjoyable as she laid on her back and he thumped his prick into her, however this was much more intense. And he wasted no time in showing her that as he pulled back and slammed back down into her pained asshole, sphincter still in spasm as it tried to accommodate him.

Billie whined in pain and buried her face in the sheets as Rob took full advantage and got to work, his hips immediately accelerating to a busy pace as he pulled back over half his cock and then slammed it deep inside her, making sure to drive himself against her round ass hard every time so she took everything he could give her. Pain shot through her body in little bolts every time he thrust into her, her tightest hole wrecked by his thick, impaling cock that plunged into her with barely any lube.

She’d done anal before a few times but it wasn’t her thing and so she hadn’t done it for a while, and had pretty much decided never to do it again either. But it wasn’t up to her and her didn’t give a fuck about her complaints, pumping his rock hard prick inside her, stretching out her asshole after having done a number on her pussy moments earlier. Billie could tell he was enjoying it by the energetic way he was thrusting, his enthusiasm evident and he was so hard for her. His cock felt even bigger in her asshole as he plundered her and it was all she could do to try and restrain her cries as she dug her fingers into the bedding and muffled herself with the sheets, feeling tears slide down her cheeks.

Rob loved the feel of her fluttering sphincter around his cock, how she was trying to get into the rhythm with him as he absolutely ploughed her, knowing full well he was going far too hard and fast for her to catch up. She writhed and twisted under him as he pounded into her, hips slapping off her round ass loudly as he buried his cock fully inside her with little whimpers and grunts as she took it, struggling with every pump. He loved it, relishing her under his control as he pounded her, taking a hand from her shoulder to grab a rough handful of her hair and pulling her head up.

“You like that, whore?” he asked through hard breaths.

“No,” she growled through gritted teeth.

“Too bad,” he replied, giving a yank to make her wince before throwing her face back down into the bed. He shoved his hand back down on her shoulder and doubled his efforts to pump into her, strokes shorter as he put more power on her to jam his cock inside her tightest hole. He loved watching her fingers dig into the bedding, feeling her pushing her hips up into prone bone position for him even as she fought the discomfort of rough anal sex. Sure he could go easier on her, give her more lube and take it steady to help her enjoy it but he had little interest in that. She was settling their debt, as agreed, so he aimed to take everything he wanted from her.

And he wanted to split her booty in two. His shorter thrusts only increased the power as he slammed down into her, his thick cock driving into her and plunging deep as she grunted throatily into the mattress beneath him. He loved how tight it was, how her asshole squeezed and stretched around him even as her spasms faded, muscle finally surrendering to his assault much in the same way her throat had. He pumped hard on the singer, using her for his pleasure which was as much the physical as the sight of her surrendering to settle their debts. She’d chosen it after all, opting for this rather than paying up.

Billie just laid and took it as he slammed her ass, feeling every thump of his big, thick cock into her as she continued to push herself up submissively for him. She knew it would all go easier if she just did as she was told and was the whore he wanted for the night, and she needed that signature to settle everything with him. It still hurt as his manhood stretched her however and it only reminded her that she didn’t like anal sex, but it was part of the deal. She’d signed herself over to him so it was how it was, even if it made her make-up run down her cheeks. It didn’t feel all bad though, she had to admit, as little tingles of pleasurable sensation rippled through her to go with the painful stretch of her asshole.

That was until he slipped out during a particularly vigorous stroke, his hard cock pushing up over her ass. He muttered in annoyance and grabbed his cock, aiming it in the blink of an eye and shoving it abruptly back inside her just as her asshole squeezed up. Her body was in rhythm with him and her muscles were working gently around his cock, even as that caused her pain, to squeeze and clench on him so when he suddenly slipped out she clamped down on nothing. That was just in time to be tight for him to plunge himself back into her, his bulbous head stretching her open again and drilling into her, making her scream loudly into the bedding as her pain level spiked, heart racing as a hot flush coursed through her.

He just smiled to himself as the singer bucked underneath him, whole body jolting as she flinched at the stab of pain and cried into the bed. She still dutifully pushed up into him however and helped him fuck her, his thrusts now really short and hard as he stamped his authority on her. As if he needed to given that Billie was completely dominated and not even attempting to fight back, her body shuddering with little sobs as he owned her and fucked her ass.

He pinned her hard and slammed himself into her, loving the sensations as he smashed her with his rock hard cock, driving it into her again and again in a blur as she whined beneath him. Her noises increased in volume as he split her in two, turning her head to let out hard, strained rasps as she was overwhelmed, not knowing what to do as her fingers turned white with the pressure of her desperate grip on the sheets. He slammed himself into the singer hard and fast with intense, crushing thrusts that drove her into the bed until she couldn’t even push herself up any more, just lost to it, completely defeated.

It was then that he suddenly yanked out, giving a hard, full depth drive into her and grinding himself before abruptly pulling out with a pop as she gasped loudly. She suddenly felt so empty as he got off her and rocked back on her knees, grabbing her ass and spreading her wide with both hands to show off her gaping, stretched asshole.

“Fuck yeah, look at that,” he said, “only whores gape like that.”

The collar was apt. Billie buried her face in humiliation as he exposed her, trying to squeeze her asshole but it was a token gesture. She was too tired and too stretched to possibly fight it and after a moment she relaxed and let herself gape wide for him. He took a moment to admire it before he climbed off her legs, letting her close them after pinning them wide for their whole fuck as he sat on the bed beside her to graciously give her a break. She took what she could get and breathed deeply, taking it all in as she reflected on the hardest anal fuck of her life.

It wasn’t over, though she didn’t realise it. He had plenty of plans for her and after a brief respite he grabbed hold of her hips and pulled her powerfully back up from the bed. Billie mumbled as he positioned her, not liking the way he was able to manhandle her so easily, hating the sheer control he had as he yanked her back up to where he wanted her – presented. She wasn’t stupid however and didn’t want more punishment so assumed the position obediently, sinking her back and rolling her hips to push her ass and smoothly shaven pussy out for him.

“Good girl,” he commented, seeing her doing what he wanted, a comment that made her seethe with anger. She hated being his good girl...and she hated even more that was sort of enjoying it.

“Now you need to be a really good girl,” he said, smacking at her ass with a couple of firm, intent spanks that made her jiggle. She didn’t mind it, it was lighter than most of the other spanks he’d given her. What opened her eyes was when he stroked over her ass and probed to her hole, running his fingertips around the stretched, gaping muscle with delicate yet firm intent. She just breathed deeply and tried to settle herself, staying calm as he pressed two digits inside her.

It wasn’t enough and they easily penetrated her stretched sphincter, making Rob immediately withdraw and add a third, plunging them in impatiently to feel her body hug them as gave a grunt. He pressed them to his knuckles and worked them intently back and forth, feeling her give way quite well, has asshole unable to hold him back after he’d fucked her. Billie just murmured as he finger fucked her in a way she’d never experienced before, trepidation abound even as she enjoyed the feeling of it.

She didn’t have to wait long for that to be realised as he pulled back and added his little finger to take it to four, folding it in with his others to squeeze them all into her asshole. Billie grunted deeply as he shoved it in to his knuckles, asshole stretching wider than it ever had before with a twinge of pain shooting through her again to remind her how it was gonna be. Rob seemingly ignored her and started thrusting them intently, shoving in against his knuckles each time as he pressed to get them deeper inside her.

 A cold shock of adrenaline washed over Billie as she realised he wasn’t stopping at just his fingers; he was intending to go deeper and force more of his hand into her, shoving hard against her asshole to make her give way as she struggled. She didn’t dare protest even as she rushed with sensations, trying not to panic as her body rocked from his efforts. Her concentration was somewhat redirected however as he reached under her with his spare hand and grabbed hold of her massive tits again, squeezing her huge rack as they swung beneath her. Rob expertly multitasked as he continued thrusting into her ass while he groped each of her massive tits in turn, gripping hard to make her wince, fingers pressing powerfully into her feminine flesh.

“Fuck!” Billie yelped as he suddenly drove forward and forced his hand inside her, taking advantage of the distraction to surge into her and drive his hand beyond the knuckles and all the way down to his thumb. She twisted and tried to pull forward but he didn’t relinquish control of her, making sure his hand stayed deep as her body clenched at him painfully.

“Christ, take it easy!” she gasped, unable to help but beg for mercy as he wasted no time in thrusting hard into her ass. She jolted at the intensity and let out a scream as Rob aggressively pinched her nipple, sending another lightning bolt of pain through her, reminding her how sharp the punishment might get if she didn’t tow the line. With that Rob continued and Billie just bit her lip to refrain from complaining as he started firmly working his hand into her with short strokes, not letting his knuckles slip back out of her as he wanted to stretch her out.

Billie groaned and whined desperately as he worked his hand into her now not so tight asshole, stretching her muscle with rocks of his wrist, testing her this way and that as he enjoyed himself despite her discomfort. She’d had anal sex before, more than once, but never had more than a playful finger in her ass and now she had four and the hand that went with them. It was way too much for her to handle but she had no choice but to endure...unless she wanted to call off their deal and pay him off. That wouldn’t undo what had already happened between them and the idea never even entered her mind as she clung on, her tits being squeezed hard as her stretched her sphincter.

With her warmed up he carefully pulled back and let his knuckles out of her, hearing her sigh in relief, only to give a strained grunt as he shoved them firmly back into her and buried his hand once more. Billie jolted at the twinge of pain though it wasn’t as bad as she’d expected, body working with him even as he treated it so aggressively. He stayed deep for a few moments then pulled back out and shoved his knuckles in again to make her wince, giving her another break then doing it again. After that she got no breaks as Rob pulled his hand back to his fingers and plunged it in once more, making her stretch over the knuckles repeatedly as he pumped his hand into her asshole.

Billie was going along with it and figuring maybe it wasn’t so bad, there was something to it that was strangely enjoyable even if that was just doing something so crazy, something she’d likely never do ever again. But Rob didn’t let her ride that wave for long as he changed the channel and pulled back, folding his thumb into his palm and thrusting it against her asshole.

“No! I can’t take it!” Billie shouted, protesting as he tried to stuff his hand into her ass, but Rob didn’t back off. Her body was stretched and tired and he drove it against her a couple of times until it went past the knuckles again to the base of his thumb. He piled the pressure on and Billie screamed loudly as pain shot through her when she gave way and his whole hand slid into her ass, sphincter squeezing down intensely around his wrist.

“Fuck, that’s it,” he growled with pleasure, shivering himself at the sight of the world famous singer taking his whole fist in her ass. His perfect anal whore, her collar absolutely correct as he forced his hand inside her. His cock was absolutely rock hard, throbbing with his heartbeat as he anally fisted her for the first time in her life. Billie was just slave to the pain, face a silent scream as her body was wracked with jolts of agony from her stretched sphincter, his hand feeling absolutely huge inside her.

“Fuck, fuck,” she stuttered, “I can’t do it, take it out, please,” she begged twisting torturously on him like an obscene glove puppet.

“It’ll hurt more if I pull it out, trust me,” he said.

“Please.”

“No, it’ll be better if you just hang on and take it, like I want,” he said, a note of finality to the struggling star that told her to be quiet. Unless she wanted another slap to go with her first anal fisting of course. She growled painfully as he started to rock his hand, curling his fingers inside her and working himself back and forth. He wasn’t too rough to begin with which she was grateful for, a small mercy that allowed her to try and get used to it though she figured she wouldn’t. She tried desperately to relax and let Rob do his thing, knowing she was on the hook for millions if she called stop.

“Is this how you treat your girlfriends?” Billie said with a strained tone, gritting her teeth as she rocked on his hand as it started to work into her a little easier. Rob paused, taking his time to let her feel it and dwell on the question at hand.

“No, because I actually respect them,” he replied simply. Billie twitched as she coursed with rage, adrenaline hitting as the anger tweaked her and made her clench, which then made her flinch in pain as her exhausted sphincter clamped on his wrist. It made her so angry to hear that, that he didn’t respect her so that was why he was treating her so roughly, that he’d never do it to someone he cared for.

“You fucking asshole!” she muttered under her breath, knowing she could do nothing to respond as he fisted her, treated to a vice tight grope of her tits in response that made her squeak in punishment.

“Shut up, cunt, just take it.”

Billie just groaned deeply with discomfort as he started pump his hand more briskly, just intending to get on with it and pushing his hand into her further as she shuddered. She dug her nails into the bed again and just resolved to take it, knowing she had little other option if she wanted to hold up her end of the deal. Rob gave long, powerful strokes of his arm at first to test her out and let her feel it, stretching her like she’d never felt before, watching her strained asshole wrapped around his arm as he plunged deep inside her.

He loved the struggling grunts and groans she gave, particularly intently when he shoved it deep and held it there, the singer unable to derive any pleasure as he fisted her ass. He switched up to faster, shorter strokes that she preferred in a way, it was less to deal with overall, but the sharper way he punched deep inside her hit with a sharper, more jolting pain. His hand still kept a firm hold of her chest, squeezing the tits he coveted so much even as he focused on splitting her in two like she’d never experienced before.

He did relinquish his grip on her tits a few moments later however...when he reached out to grab his phone from the side unit. Billie barely registered what he was doing as she struggled and writhed in front of him, his fist still shoving hard into her ass, making her brace herself on the bed to take it. She wasn’t sure she wanted to but there was no choice, and she was taking it easier than she had been at least. Rob swiped his phone easily and opened the camera, holding it up behind her to get her most undignified moment in frame.

The click of the camera cut the air like a knife despite its quiet tone and Billie felt a rush of terror hit her, making her clench again and jolt with pain, letting out a deeper, more primal grunt as it bolted through her. Blood rushed to her face as she blushed, realising the photo he must have got of her, her asshole gratuitously stretched around his arm as he fisted her, something she could never have him show to anyone else. Her heart rate was already high but it accelerated for a moment as she tried to breathe through it, still rocking with his fisting as she tried to think, to rationalise it out that surely nobody would recognise her anyway if they did see it.

But it was pushed from her mind by the harder, more intent thrusts of his fist into her that buried his hand deeper again and send a blur of sensations through her. She grunted sharply with the accelerated motion as pain mixed with a strangely full sensation of pleasure, streaking together like watercolours as he pumped his arm and stretched her hard. Her asshole was completely exhausted and it offered no resistance, allowing him to really start to hammer her and show her who was boss...as if that were needed.

He drove his fist harder, plunging it forward into her as she winced, her grunts turning to shouts as he overwhelmed her. Pain shot through her as he stretched every last bit of her he could, really giving her payback to settle their deal, ratcheting it up until her was fairly pounding her with his fist. Billie screamed as he held her tits tightly and pumped her, body bucking and flinching, unsure what to do with herself as she struggled for control.

“Fucking take it, Billie!” he spat, smile on his face as his conquest struggled under his efforts.

“Tell me what got you here,” he ordered.

“What?” she gasped, barely twitching as he pinched her nipple for not addressing him properly, lost to the fisting.

“Tell me why you’re here, degrade yourself, you whore,” he commanded. Billie rushed, body surging with adrenaline as she contemplated it, figuring she knew what he wanted to hear. She hated being called a whore but at that moment she couldn’t really disagree as she’d opted to let him do as he pleased with her in exchange for the deal.

“This is what happens to stupid whores,” she growled, wincing as he thrust hard and made her rock.

“Damn right it is.”

“And this is how I settle business deals, being a fucking whore,” she continued, face red with embarrassment which she was glad he couldn’t see. It was evidently what he wanted to hear as he thrust her faster, with more excitement. She imagined how hard his cock must be, standing up in front of him ready for her and she was sure she’d feel that again before they were done.

“What else?” he demanded, a slap hitting her face, snapping her sharply back to things after losing herself a moment.

“This is what I let guys do to me, anything they fucking want to make a deal,” she gasped.

“Any hole, any time, whatever it takes!” she said firmly, knowing it was what he wanted, his thrusts now hard and short, twisting his fist as he made her take it, body wracked with sensations as she grunted through her words.

“My mouth isn’t my only talented hole,” she hissed through gritted teeth as a particularly hard pump made her flinch. She was lost to it all as he suddenly pounded her hard and rammed his fist into her ass as hard and fast as possible, a long, screaming groan escaping to the bedroom as he drove her to her absolute limit.

In a moment that seemed to slow time Rob suddenly pulled back and thrust hard, arm yanking back much further and pulling his whole hand back out of her asshole beyond the widest point of his knuckles. Her loosened, broken sphincter let him pop out for a blink before he jammed it back into her, stretching her hard on both the way out then the aggressive drive back inside her. Billie’s eyes flew wide open and her voice exploded in a loud, high pitched scream that cracked and turned to agonised silence as she collapsed on the bed and almost passed out.

Her body was split in half by the pain, like a razor sharp blade slicing her soul in two in an instant and made her see stars, slumping helplessly down on the bed a strength evaporated and she almost blacked out. Rob kept thrusting as he laughed and reached up to slap her face hard, making the singer gasp gutturally as she wrenched away from him and hauled in oxygen to try and regain control. She tried to focus her eyes as she breathed deeply and tried to saturate herself, pain fading as her head spun.

“Come on, Billie, hang in there. If you pass out we’ll need a third session to settle this,” he laughed, continuing the fist her loose asshole. She just held on tight and kept breathing deep as he pumped her hard, jamming into her repeatedly as she shook on the bed, digging her knees in and holding on. His arm pistoned back and forth hard to give her an intense final flurry, a final deep plunge before he suddenly yanked his arm straight back and pulled his fist out of her, stretching her asshole wide a final time.

“Fuck!” she screamed, jolting as he pulled back then rocked back on his heels to grab her ass with both hands and spread her wide, exposing the trembling singer and pulling her gaping hole wide open. Her loosened pussy pulled open at the same time and she made no effort to even try and clench up, completely defeated as he admired his handiwork, her holes gaping wider than they’d ever done before.

“Very nice, even if I do say so myself,” he commented. Billie could hear the smirk in his voice, feeling absolutely humiliated as he showed her off and just degraded her further. He reached out for his phone and swiped open his camera, squeezing her ass with his other hand to pull her open for it before he took a few shots of her gratuitously gaping holes, the widest they’d ever been after he’d worked her over.

Throwing his phone aside once more, he let her go then smacked her firmly, making her jiggle as he left light marks on her but Billie could hardly feel it. She was just numb and lost to it all, his toy to play with. Rob certainly wasn’t finished with her and he knelt up behind her, grabbing his rock hard cock to aim it down at her as he gripped her ass once more. Thrusting forward, he slid straight into he slick vagina and buried himself deeply to make her mumble casually, feeling how stretched and tired she was.

He pulled out of her and aimed it straight up at her asshole, driving forward again to easily fall into her, effortlessly diving full depth inside her and forcing his hips against her round ass. Her body offered no resistance and he could barely feel her around him, muscles unable to squeeze or clench as he pushed into her.

“Fuck that’s loose, what a whore you are,” he said.

“Your whore,” she breathed, just telling him what he wanted to hear, her attitude going with the wide leather at her neck. He thrust a few more times then pulled out, figuring it pointless fucking her. He shoved her hips and Billie tumbled exhaustedly onto her side, looking up to see what he had planned as he slid back off the bed, standing with his cock rock hard, harder than she’d ever seen.

“Come here,” he said, lunging forward to grab her arm so he could haul her across the bed. She was just his to manipulate and slid across the sheets until her head sagged back off the side of mattress where he wanted her. She knew exactly what was coming so it was no surprise when he dipped down and pressed his cock to her mouth, the singer opening wide to let him slide his cock into her hot mouth.

It was her tightest hole after everything he’d done to her and he groaned with pleasure as her hot, wet mouth wrapped around him. He gave her no break and forced his cock deep into her, past the clench of her throat to press his balls against her face. Billie gave a jolt and gagged as he forced in but it was minimal, her muscles tired after choking on him earlier and so he had little problem getting straight back to what he wanted.

“Fuck that’s it,” he growled shivering with pleasure and flexing in her throat. Billie felt him pulse hard, a sensation she knew that meant he was close. He had control though and held her head hard as he immediately turned the pace up to eleven and pumped her hard, using the whole length of his big cock to jam in and out of her as she gave loud, wet gagging sounds. Her throat pulsed and squeezed around him as he fucked her mouth, her hands digging into the bedding again as she held on tightly and took it.

The singer’s massive, marked-up tits shook heavily as he pounded her, legs kicking uncomfortably against the bedding as she struggled to get breaths around his impaling cock. She braced herself as he really picked it up, his cock stiffening and swelling in her throat, so hard in a way that only meant one thing and she felt a wash of relief that he was about to explode. Still, she had to endure the last few moments of him fucking her throat which was tough as he plunged harder, getting new depth and then fucked her relentlessly with short, rapid strokes that jammed him against her.

It was an intense few seconds that seemed to stretch much longer as he absolutely pounded her face and chased every last ounce of his pleasure. She managed to hang in and didn’t dare fight or try and complain, just wanting to bring him everything possible as she worked her tired tongued against his shaft to assist. With a sudden jolt he was ready wrenched back out of her, drawing a loud rasping choke from the singer as he immediate withdrawal made her retch, looking up just in time to see Rob jerking his cock ferociously before aiming at her face.

Billie barely shut her eyes before a huge, hot spurt of his come splashed across her face with power that made her gasp. Rob grabbed her collar and growled deeply with release as he tensed and pulsed himself to explode repeatedly over her with thick, abundant bursts of his load. He hadn’t ejaculated in days in readiness for that moment, wanting Billie to feel everything he had for her and so he revelled in the huge sensations that washed through him as he pulled her close.

His thick come landed in her mouth and over her chin, finishing on her neck as he painted her, further jets landing with expert aim across her forehead, cheeks and nose to completely cover her. Despite the heat of humiliation warming her face she was kind of impressed as Rob so perfectly blew his load over her face and made sure to hit her everywhere, taking his chance to really cover her. She felt his salty come sink into the back of her aching throat as she kept her mouth open obediently for him, letting him finish, hearing his ragged, harsh gasps as he squeezed every last little bit out for her.

He flicked the last of his load onto her to make her flinch a little before milking a final drop to his tip and dipping to wipe it into her hair, making her growl in disapproval. It hardly mattered anyway, she needed a long shower to wash away even some of what they’d done. All that broke the air was their heavy breathing, recovering in the aftermath of an exhausting and overwhelming fuck.

Billie was broken, splayed on the bed; she felt so heavy that she couldn’t even move and just sank into the sweaty sheets, head lolling over the side of the mattress as she willed some energy into herself. Rob stepped away, head buzzing in the wake of his long awaited peak to grab his phone once again. The singer just laid helplessly on the bed as he took several more photos of her spread out naked on the bed, tits red from the slaps and gropes he’d given her and face covered in his thick load. He got a close up of that, his handiwork, to go with the rest of the gratuitous photos he’d taken of her.

“You try and screw me on this again and everyone’s gonna see these pics.”

The statement was clear, and Billie knew exactly what he meant. It was insurance if she tried to do anything else similar to screw him out of his fair share again. She swallowed heavily to clear her mouth, the salty taste of his load spreading over her tongue.

“I won’t, a deal’s a deal,” she replied.

“Good.”

“Are we done?” she asked, swallowing again.

“Yeah we’re done, we’re square,” he replied, a wave of release washing through Billie as he told her their deal was complete and her debt was paid.

“I’ll get the paperwork completed and sent to you, as agreed.”

“Thanks,” she mumbled, even though she had little to be thankful for. She’d paid with her body and he’d certainly got his money worth out of her. The singer was just laid on the bed where he’d left her, exhausted and broken, knowing she needed to move but unable to fund the energy.

“I’m gonna grab a drink,” he said, slinging on a robe from the back of his bedroom door and tying it round himself, “you want anything?”

“I need a shower, but I guess you just want me to get the fuck outta here,” she murmured. It wasn’t a dig at him, she was just referencing the way he’d treated her previously.

“Bathroom’s down the hall,” he said after a pause, his stance softened, “but don’t take the piss.”

“I’ll make it quick,” she replied, feeling a little tingle as he show deference to her. It was stupid after what he’d done and how he’d used her, but she liked the softer side even if it was pathetically minor.

Rob left the room and headed downstairs to get himself a drink. He didn’t immediately come back upstairs to her which she was grateful for as she laid on the bed, totally washed out and limp in the aftermath. It took a few minutes to recover, just letting her mind go blank as she zoned out to recover somewhat. She knew it would take days to get over it however and she also knew the clock was ticking; he might be showing her some softness but he’d surely kick her ass out if she wasted too much time so she steeled herself, shaking herself back to it and breathing deep to get cleaned up.

His load was still spattered over her face and running down her cheeks, so after a brief stretch she hauled herself up and turned to sit on the side of the bed. She found some tissue from his side unit and wiped her face, careful no to get it in her eyes as she did enough to allow her to find her way to his bathroom. She undid the collar before standing up gingerly, wincing at the pain from how he’d stretched and fucked her, taking a towel from his door and then carefully finding her way from his room to the bathroom. She didn’t bother to wrap up, there was little point, and just got the shower going.

The hot, steamy water was like heaven as she immersed her curvy body, the cascade washing away the discomfort somewhat though her glance in his mirror showed the redness of her face and hand prints on her tits, reminding her what she’d surrendered to make the deal. It was her choice though, so she mentally shrugged and figured she just had to get past it. Billie washed herself down thoroughly and cleaned up as best she could, making it quick and figuring she could have a shower at her place.

Hurrying back to the room she found Rob waiting for her, sipping his beer, but played it cool and simply dried off casually and found her sexy lacy underwear, pulling it on matter of factly and then dressing as he watched her. He enjoyed seeing the curvy star dressing but made no comment, letting her just do it.

“We done then?” she asked, wanting to make sure her part was complete.

“Yeah we’re done, deal’s closed.”

Billie looked at him a moment, raising an eyebrow in the silence, before she extended a hand to him. Rob gave a sly smile and reached out, shaking with her to close the deal. There was nothing else to say and Billie headed for the door, Rob following to see her out. He opened the door and she walked carefully down his steps, hoping her motion didn’t show how sore she was feeling as she did so until she got to the bottom and turned back to him. She stared at him for a moment then blew him a kiss slowly, tauntingly, as if saying she’d got the better end of the deal.

They both knew that was bullshit.

Billie headed away from his place in the darkness, not looking back as she heard the door shut, getting a little way around the corner before she stopped and sagged against a wall. The pain overtook her for a moment, feeling so exhausted she could barely stand, taking a moment to recover. She considered calling a cab but decided not to as her place wasn’t so far and she knew she could make it. Besides, she didn’t want to risk that being put in some gossip column.

Billie made it home around twenty minutes later, aching and exhausted, locking her door and staggering to her couch where she collapsed face down. She hauled a throw from the back of the sofa over her and wrapped up, just feeling completely overwhelmed, and within moments she passed out.

* * *


She awoke the next morning, the sun pouring through her windows as she wondered where the hell she was. It took her moments to remember, and she awkwardly untangled herself from the blanket and sat up, wincing at the pain. It all instantly came back to her and she looked at the clock, seeing it was going on eleven and she’d slept for hours, body just needing the rest.

She took a shower and checked herself out, seeing herself still gaping, a little unsure she’d ever be the same again as she felt it all with every step. The marks on her tits still hadn’t faded, feeling tender to the touch along with the rest of her. Just walking was uncomfortable and she knew it would take days to get over, resolving to just hide away at her place for a while and give herself the time. Billie found herself far too delicate for any intimate touch either, not wanting to give herself any self care in the aftermath of it all.

It took days to feel stronger again and she just tried to keep herself busy. She put it all from her mind and relaxed, watched movies, slept and silently thanked God when the papers from Rob were delivered. All signed and agreed, as he’d promised, and she knew the deal was truly complete.

When she did masturbate a few days later, whilst laying in the bath to help her aching muscles, she thought of him. She hadn’t intended to and didn’t even really want to but she couldn’t help it, her mind locking onto how intensely he’d treated her, how he’d used and fucked her...and how he’d made her come. The orgasms had certainly been hard and she couldn’t deny she’d loved those, but she hated admitting that and definitely didn’t intend to to Rob.

She figured it was just all the emotions from the night boiling over and giving her those fantasies, but they persisted. Any time she felt even remotely hot he was immediately present in her mind, even if she tried to think about other things. Billie couldn’t banish him and in the end just let him in, thinking how he’d dominated and owned her, absolutely fucked her the way no other man ever had. It made her hotter than thinking about anything else and she knew she needed more of it, to get rough and properly fucked, a man taking charge of her and just using her as he saw fit. It flashed through her mind repeatedly over the following couple of weeks every times her fingers danced on her clit, frustrating and exciting her in equal measure.

And she decided she could wait no further. She’d recovered from their session and felt herself again, even if she was perhaps a little wiser for the future. But she was horny, and desperately needed a rough session. But she was single and that wasn’t as easy to get as she might desire...unless she did the unthinkable.

Rob.

He was the obvious choice. He was single as well and ultimately the ideal candidate. She knew he’d do her in the way she needed, that’d already been proven, and would surely take her up on it. However to get it she had to swallow her pride and approach him for it, which she hated. But she hated not getting fucked even more, and so after a couple of drinks on another night alone she picked up her phone and called him.

“Hey Billie, you alright?” he asked a little uncertainly. He hadn’t been expecting a call from her, potentially ever again.

“Yeah I’m good, what you up to?” she asked, her heart pounding in her ears.

“Chilling, how about you?”

“Just the same, chilling,” she replied. The silence hung in the air, Billie unable to form words to take it forward.

“Look Billie, I know you didn’t call me for a casual chat so cut the shit. What’s up?”

“Do you wanna fuck me again?” she blurted out, forcing herself to say it sharply, knowing she’d lose her nerve if she didn’t.

“Our deal is done, Billie,” he replied carefully.

“I know.”

“But you want me to fuck you again anyway?”

“Yeah, this is nothing to do with our deal. That’s forgotten,” she said, finding her confidence. She was making the play for what she wanted.

“So this is just a booty call?”

“Yeah.”

“Feeling lonely and wanna get fucked huh?” he asked, trying to keep the smile from his voice.

“Exactly that,” she said, “I figured you might wanna?”

“Sure, as long as you know the deal,” he said.

“What deal?”

“That I’m gonna fuck you as hard and rough as I want, just like before. The same rules apply,” he said.

“That’s exactly what I need,” she mumbled.

“Then sure, I’ll fuck you.”

“Good, when?” she asked.

“Right now, but if you want it you gotta come to my place and get it,” he told her, immediately taking charge again, exactly as it had been before - exactly as she wanted it.

“I’m on my way, put the vodka out for me.”

“I will. Now don’t keep me waiting, bring your A game,” he replied, before abruptly hanging up on her. Billie immediately got up to get ready for him, to put on more sexy underwear for him to ignore...

__________

The End

Big thanks to Ghost for helping create, plan, check and edit this story.

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