“Well, that was fun,” Anna murmured, turning her head on the pillows and blowing her hair back from her face, blinking at the light of the room.
“Yeah, I really needed that,” he breathed, looking over to her and reaching out to trail his hand over her ass, giving a squeeze.
“I noticed,” she said with a smile, having been able to see and feel his energy, just giving himself all to her. Not that she minded, she hadn't been fucked in a while and he'd certainly done a good job on her and it helped confirm her decision to give herself to him as payment to make up for scaring off his date.
“So, our deal still on? For the weekend?” he asked, a lot clearer and less nervous than he had been when they discussed it earlier. It wasn't surprising when he'd just fucked her brains out, but still gave a silent prayer she hadn't changed her mind.
“Yeah we've got a deal,” she said, glancing back to him slightly, “you've got the weekend to get even with me.”
“I want to be in charge, like...properly in charge,” Josh said, referring to something they'd discussed on the phone earlier when they'd thrashed out their potential deal. He'd made quite clear that he wanted to be in charge of things and dominate her; it was still about pleasure, he was going to make sure she had fun as much as he did, but he wanted control and to introduce her to a few new things. She wasn't as innocent as people might expect her to be, being somewhat “one of the quiet ones” that people warned their sons to stay away from, but there were still some things she'd never tried and she'd figured it was a good opportunity to possibly give them a go. She'd been a little surprised he wanted to get kinky with her, but then she figured he was a quiet kind of guy as well and just kept it hidden.
“I know,” she said, thinking about it momentarily in case she should put some limits or control on it, but her conscience ate at her that little bit again and she decided not to, letting him have at her. She was definitely going to let him get even.
“You good for that? I don't want to pressure you or anything,” he offered, not wanting her to say no but giving her the freedom to choose.
“Hey, we made a deal,” she said, committing to the proposition. His heart gripped tightly before it pumped hard again, excitement rushing through him as the stunning, petite actress surrendered herself. His hand gripped her ass for a hard squeeze, his desire evident, Anna's nerves rushing a little as she contemplated what she'd got herself into. They both just lay resting for a few more minutes, Anna turning over as he shuffled up to the pillows to cuddle into him, where he directed her dainty hand down to his semi-hard cock. She giggled slightly as he did, immediately taking control and directing her actions, closing her slender fingers around him and starting to softly stroke him, squeezing and massaging him gently to help tease him back to erection. His hand smoothly ran over her hip and ass, grasping it firmly, just feeling the tone of her body, pulling her cheek up to let his fingers tease down over the tight ring of her asshole and at the back of her slick labia.
Anna just relaxed into him, liking the feel of his manly body beside her, holding her close as she carefully worked at his cock with her slender hands, looking down to watch as he swelled in her digits with the neat, meticulous ministrations of her grip. Stroking him to erection, she gripped him tighter and started jerking him properly, feeling his flesh resisting her attempts to compress it with her hand as she wrapped it around him, stroking firmly all the way along his length.
“I want you to suck it,” he murmured, pushing up a little into her hand.
“Is that a request or an order?” she asked with a smile, playing into him having control of her.
“An order,” he said, more firmly, looking down to the pretty actress as she slowly, teasingly stroked at him.
“My first order, interesting,” she murmured, looking into his eyes with a smile, which faded as his expression hardened, staring into her big blue eyes in a steely moment where everything turned on her.
“Anna, suck my cock,” he said firmly, almost coldly, dominantly. Her heart squeezed, skipping a beat and then releasing into a flutter of rapid thumps, pounding against her rib cage as he stared into her eyes. Spurred into action, Anna shuffled down on the bed as she gave a squeeze to his cock and flicked her hair aside, getting herself ready for it; even though she'd given a lot of blowjobs, it being something she actually quite enjoyed doing, she was nervous, feeling like it was her first time or that she was under scrutiny. Eyeing his thick cock, she stroked it a few times as she wet her mouth and took a deep breath before she dipped down and engulfed his manhood in liquid heat. He groaned with pleasure as the petite actress held him up and sucked at his cock, easily sliding him into her mouth, pushing the bulging head over her hot tongue towards the back of her mouth.
“Oh yeah that's it,” he breathed, almost enjoying it more than the first time she'd done it. He just let her work, able to sense her obvious experience with it, the brunette bobbing up and down easily, feeling her working her tongue around his head and pushing him into her cheeks for the change in sensations. She worked deeper than she had before, stressing his bulging head against her throat, letting him feel her muscles starting to expand to take him before she pulled back to suck up and down his length again, lips pouting perfectly around his shaft as she slid them along him. His hand pushed into her long, dark hair, fingers twisting through the soft strands as they wrapped around her skull to guide her head, a controlling hand on her even as he let her do her thing. Anna's heart pumped a little harder, feeling his grip on her, finding it somewhat irritating yet sexy, loving the strong, manly hold he took on her as she sucked his cock. He let her continue her ministrations for a minute or so more, just relishing the velvet heat of her mouth as she slipped up and down him before he shifted on the bed beneath her, turning more towards her and sliding his other hand up to her head.
Anna's heart rate spiked as he took hold of her, knowing it was a change up and he was taking charge; it barely had time to do more than a few beats before he pushed his hips up whilst hauling her down onto him, forcing his cock into her throat a couple more inches before she was able to resist, feeling the fantastic contractions of her around him as she gagged and forced him back out, lurching and coughing over him in response. He tingled with excitement as he ignored her reaction, his cock straining with arousal as she composed herself, gasping a couple of breaths before her urged her to resume her rhythm on him, bobbing up and down again to suck obediently at his cock. He was controlling her head now though, making her blow him faster, mouth gliding up and down him as her heart pounded, breathing more intently through her nose as she focused on giving the blowjob she'd surrendered herself to. His hands gripped her tightly again and he drove her down, forcing himself into her waiting throat once more just after getting her settled into the rhythm again, as relaxed and unsuspecting as she would get right in time for him to jam her down deep, forcing his cock just a bit further this time, another inch into the pretty actress before she retched and fought back, pushing herself back up and gasping wetly for breath.
“I can't do this,” she gasped raggedly through deep inhales, eyes watering, make-up running as she swallowed and tried to catch her breath.
“You can,” he said simply, reaffirming his grasp on her head, using his fingers to pull her hair up away from her face.
“I can't!” she said more vehemently, mouth still over his throbbing cock, bouncing slightly with every pulse.
“You will!” he almost snapped in response, sudden and emotional, his heart now racing at his own strong dominance of her, taking charge of the situation properly. Anna felt a rush go through her; she'd never been controlled like this before, she hated it but also loved it, it was new and exciting. With that, she took another breath and leaned down to take his cock back into her mouth, letting her tongue glide over every contour of his thick head before going deeper and resuming her rhythm on him, his hands following to control her pace once more. She surrendered to his wants, knowing she was at his whim now, her resolve breaking as she started sucking his cock again, protesting no more and knowing he was going to stretch her throat out. He bounced her up and down more intently, feeling her tension, knowing he needed her to relax really but he was going to have to simply drive her through it instead. With another hard yank on her hair he pulled her down, shoving deeply again and feeling her attempting to accommodate it, fighting her own body as he made her gag and push off him again, getting no further.
This time however she didn't complain, simply coughing and pulling back to breathe, taking a moment then swallowing his cock again, wrapping her tongue around him and pushing him back to her throat. He let her bob a couple of times again and then forced her down, finding her much more ready this time, giving way under his pressure and letting his thick head slide down her throat till she was nearly all the way down before she convulsed and pushed back off him, trying to control her gag. Holding her head, he gave her a moment and then slowly pushed her down once more, to the back of her throat and then onwards, straight into the deepthroat. Anna stayed calm, letting it happen, feeling herself stretch and holding everything else back, the gag rising in her; she managed to hold it back, only a half lurch of her body as he hesitated just a moment and then forced her down, taking advantage of her muscles relaxing again and following them through to drive his whole cock down her throat until he pressed her nose into his balls with a huge tingle of excitement, pushing himself up against her as he held her face down into him.
“Ohh fuck,” he groaned gutturally as he shook, tightly constraining the brunette as she took his whole cock down her throat, holding for a moment before her body lurched again, gagging and shoving her hands hard into the bed to shove herself back up, relieved that he let her escape his grip as she broke free and gasped desperately, a thick string of saliva dripping from her mouth onto the bed.
“That's it, good girl,” he encouraged, cock throbbing with arousal now, feeling so exhilarated at getting her to fully deepthroat. It was the first time she ever had, never having taken a cock so deep or been treated this way, breathing raggedly with his hands still twisted in her hair. She felt stupidly proud though, like she'd achieved something and not wanting to disappoint him now as she shoved her mouth back onto his cock, breathing through her nose as she gave up control again and let him thrust into her mouth. With the seal broken, he let his excitement take over and started thrusting hard into her throat, holding her down and going for it, Anna struggling to take him still as she coughed and choked, not pulling up now though, not that he was letting her as he pumped into her mouth, wanting to finish her properly. Her eyes streamed, dark make-up running down her cheeks, dribbling copiously as he pumped wetly into her mouth, her pout wrapped around his shaft, throbbing and straining against her tongue as he fucked her face, getting most of the way down each time as she tried to contain her gags.
He went hard and fast now, not caring for her at all as she braced herself on the bed over him, just letting him pound his cock into her, mouth hot and wet around him as he felt her throat strain and tighten every time he thrust in. She was taking it well and he gave another full depth thrust, shoving her down completely again to bury himself in her throat, Anna caught unaware and taking it easily, sinking full depth to hold her down again as she coughed hard around him. It was all it took and he felt his balls tighten, the irresistible sensation coursing through him, hardening his cock even more as he thrust into her with a flurry of motion, taking every last moment of sensation he could. Anna felt his cock stiffen even though her tumble of thoughts and emotions, barely able to focus on anything besides sucking his cock; she knew he was going to come and wanted him to pull out, but he had no such intention. With a final few thrusts he jammed her down hard, harder than he had at any point previously, his entire cock buried in her throat once more as he came hard with a long growl of pleasure.
It was only heightened as she gagged hard, caught out by the sudden deepthroat again but also not wanting him to come, body overwhelmed as she tried to resist, throat convulsing around him as her eyes streamed and she coughed through her nose, his cock immovable in her throat as he held her down with strength she couldn't fight, trying to push up helplessly against him as his balls squeezed to explode another thick, abundant load straight into her throat. She mumbled her discomfort hopelessly as he gasped with every thrust, pushing into her face as he drained every last bit of himself into her; Anna hated when guys came in her mouth, she always had and had only done it a couple of times before swearing never again, but she had no choice now. She couldn't taste it with him blowing so deep in her throat but she knew it was there, wishing she could spit. That choice was taken away as he suddenly pinched her nose, making it clear what he wanted, and after a moment of sheer panic without oxygen she swallowed messily, gagging noisily around him as she gulped it down, eliciting another shudder and groan from him as she stimulated his sensitive cock.
“Oh fuck Anna, great job,” he groaned, flopping back into the bed as he released her, done with the pretty brunette now as she wrenched off him, coughing uncontrollably and gagging a couple of times, head down as she leaned on the bed over him, drooling as she struggled to haul in much needed breaths, glad it was over as she tried to recover.
“Fucking asshole,” she muttered, emotions overcoming her; she didn't really mean it, it was just in the moment as she was totally overwhelmed. Guys never treated her like that and she hated that he had in a way, but she'd agreed to it and there was one other thing - her pussy was absolutely dripping wet.
“You love it,” he said, sliding his hand up the back of her thigh to her pussy, juices coating his fingers as he merely touched her, having noticed it from his position as she knelt on all fours, being spurred on to treat her as he wanted and put her to the test as he could see she was enjoying it. Anna let out a loud gasp and jumped as he touched her clit, feeling like a lightning bolt as her whole body surged at his touch. She groaned in pleasure and pushed back into his fingers as he wasted no time in getting going on her, massaging her clit briskly and working solely to push her to orgasm. She rocked her hips with him to maximise his stimulation, groaning deeply as he moved his hand to delve two fingers deeply into her drenched, waiting pussy, the gorgeous little brunette pushing back into him to make sure they got to full depth inside her.
Rocking his hand to work them inside her tight, clenching tunnel, he pushed his thumb against her asshole, testingly pushing and exploring it with the rocks of his hand as he worked it back and forth, bringing his ring finger back into contact with her stiff clit. She just groaned with absolute surrender as he played her perfectly, not minding the stimulation to her asshole, feeling her sphincter being teasingly stretched by his digit as the others smoothly rocked in her vagina, his ring finger surprisingly skilful as he worked the tip of it back and forth over her button. With her arousal and need, it didn't take more than a couple of minutes until she bubbled over in another orgasm, working her pelvis rapidly to get everything she could from his touch before shuddering in a deep, soulful climax on the bed, still on all fours beside him until she pulled forward and slipped face down on the sheets. He gave her a couple of minutes to recover, loving how her make-up had streamed down her face during the blowjob and feeling generally very happy with how things were going; it was all he could ask for.
“Come on, up,” he instructed, pulling him self up and smacking Anna on the ass, her firm booty jiggling as he did. She rolled to her side and looked up at him, pushing her hair back as he got off the bed to stand.
“Why? I'm comfy here,” she smiled, stretching.
“We're not done yet,” he said, opening a cupboard and finding what he was looking for easily, knowing exactly what he was after. Anna pushed herself up to sit, perky breasts hanging firmly on her chest as she watched him pull out several straps, noting the cuffs with widened eyes as he threw them onto the bed.
“What are they?” she asked, brain not quite clicking.
“Discipline,” he replied with a smile, picking one up to fasten it to the corner of the bed as she picked one up herself to inspect it.
“Have you ever been tied up before?” he asked as he easily and swiftly fixed the straps to the corners of the bed, taking the one from her hands.
“Not much. Played around with it a bit but never that much,” she replied, watching as he affixed the final strap.
“This'll be fun, I promise,” he said, sliding onto the bed with her again, taking her arm to pull her wrist to the waiting cuff.
“I hope so,” she replied, nerves tingling at her, taking a breath as he took control of her body again. She slid down onto the bed to lie back as he restrained her, putting her wrist into the soft cuff and wrapping it around her wrist, securing the Velcro to tightly but comfortably restrain her. He repeated it with her other hand, leaving her laid with her arms out behind her head tied to the headboard, already helpless and at his mercy. Despite this he moved down, pulling her legs out towards the corners and adjusting the straps to firmly secure her ankles, leaving her splayed on her back before him, absolutely unable to resist anything he wanted to do with her, just as he had planned. She looked up at him with her big blue eyes, waiting for the next stage as he slid back onto the bed over her, rock hard cock throbbing once more for her as he positioned himself between her silky legs, leaning down to kiss her quite softly, a break in the rhythm almost as they took a moment to make out before he gripped his cock and quite firmly drove it into her as they both groaned again.
Her pussy was wet and relaxed, letting him glide easily into her once more and bottom out against her; it was a slightly different feeling now with the angle he had on her, Anna laid out flat on the bed, unable to lift her knees and rolls her hips back for him, feeling him touching different places inside her for a change in sensations. Leaning over her on his elbows, he looked down into her eyes as he slowly and powerfully fucked her, working his hips very deliberately to thrust every inch of his throbbing manhood into her tight body, loving the exquisite sensations of her silky walls clenching around his cock. Anna pulled at her restraints as she tried to engage more, wanting to be more a part of the fuck, finding it rather intimate as he kissed at her neck and shoulder, his cock just rocking in and out of her, frustrating her that she couldn't do anything to make him go faster. Every time she tried to push her hips down into him or squeeze her pussy excessively to encourage him he simply paused, holding back with just his head inside her, smiling as he made her wait, taunting her with little motions that drove her crazy and made her grumble frustratedly, spurring her to try and make him fuck her, only making him wait longer before he would suddenly bury himself fully in her again to drive a huge moan of pleasure and tingle throughout her body.
Fucking her for several minutes, they enjoyed a quiet moment together, one that almost signified what she'd got herself into. At his mercy, under his total control, being fucked exactly as he wanted it. And that's what it was; they weren't having sex or making love, he was fucking her, no matter how much she enjoyed it right at that moment, she was his fuck doll. With that in mind, he gave her one final drive, making her take every last bit of him before he pulled out and climbed off her, leaving her wondering what he was doing as he found something else from the cupboard, eyes widening as he turned back with a leather flogger and a blindfold in his hands.
“I don't know about that,” she said, craning her head up a bit.
“It's not your decision,” he said simply, confidently. Anna's heart surged, nerves shaking her up again.
“No, it's not,” she replied quietly, almost meekly, seeming to have surrendered to his control so easily.
“I won't hurt you...much,” he said, “I just want to see where your limits are.”
“Ok,” she breathed after a moment even as he was pulling the blindfold onto her, “let's do this.”
Laying back and relaxing a bit, Anna breathed deep to slow her heart rate, aiming to be calm and collected for this to happen. She'd barely been tied up before, so to be restrained so completely was totally new for her, and now that he was going to introduce her to physical discipline only made her heart race, so she resolved to calm down and let it happen. With her blindfold in place he slid back to stand beside the bed, eyeing the gorgeous brunette actress spread out before him as he picked up the flogger and settled his grip. He reached out and trailed the leather tails of the flogger across her body, just tickling it from her neck all the way down her legs, watching her shiver and tense under it. Her breathing was deep but controlled, waiting for the moment; he pulled the flogger back and laid a light flick out onto her pale body, striking her toned tummy.
Anna gasped in shock as much as anything, still totally unready for it despite her mental preparation, flinching as the ends of the leather strips smacking off her skin. She didn't protest or cry out though, simply taking it, ready for him to continue. He laid another few gentle smacks of it over her body, across her tummy, down her legs and over her chest, tingling her perky breasts before dragging it threateningly across her face as she breathed excitedly. He stepped up the power quite significantly to thwack her hard with the flogger across the chest, making her gorgeous tits jiggle and Anna give a cry as the leather caught her nipple, making the hard point throb as goose pimples spread all over her petite body. She arched off the bed as he laid a series of stinging smacks of the flogger all over her, working down her body, a few down her thighs before he planted one straight on her pussy to make her cry out at the stinging hit on her most sensitive area.
She never once asked him to stop though, laying back on the bed and taking it, arching and writhing in her bondage, pulling hard against the cuffs as she tried to twist and turn away from the blows, not desperate to escape but her body responding instinctively to try and shield herself from the reigning blows of the leather onto her soft skin. He gave her a few final hits, eliciting cries from her as the sting started to get through and she reached her limit, yanking at the bondage as she resisted begging him to stop, not wanting to appear weak. He lived up to what he'd said however, wanting to test her limits and able to read her discomfort, knowing he'd found her maximum right now and not pushing her further, dropping the flogger onto her chest and just sliding it off over her breast as she sighed in relief, knowing it was over. He dropped the flogger aside and went to the foot of the bed to release her ankles, wanting more mobility with her now and setting her free, Anna immediately bending and stretching her legs to relieve the tension in them. Sliding himself back onto the bed at her feet, he gathered her legs up and pulled them over his shoulders, hard cock ready and waiting as he reached down to push it against her pussy.
“Oh god fuck me,” she breathed, a moment of clear honesty from her, pussy dripping wet in the wake of her discipline. She'd never known she'd like being treated this way and her body was making it clear, horny as hell and just needing him to bury his cock inside her. He did just that, leaning into her legs and sinking himself full depth inside her as she cried out, his deep plunge just hurting a little bit, but he didn't pay any attention to her and simply pushed over her, bending her legs back and leaving her helpless to him as he started pumping hard and deep into her sweet, hot pussy. Anna groaned in pleasure as she shuddered, loving the feel of him jamming down into her, his thick cock stretching her beautifully as he drove his hips into her, legs back and completely vulnerable to his wants. She pulled at the straps on her wrists, wishing she could engage more in the fuck, pull her arms around his back and make him stay there till he was done, but she was helplessly bound, restrained, dominated by him.
“You like that, Anna?” he said, smiling down to her as she lay blindfolded below him, body rocking with his powerful hammering.
“Uh huh....” she managed, groaning incoherently as he pounded her pussy. Leaning up, he held her under her knees as he smashed himself into her as hard as possible a few more times, watching her lovely, smoothly shaven pussy wrapped around his shaft before he gave a final hard push and yanked out, making her gasp loudly and jolt, leaning up to look instinctively despite the blindfold. He threw her legs to the side, rolling her over on the bed and twisting her arms beneath her as the straps offered no give to her wrists. She mumbled in surprise as she rolled over, her legs carrying her over before he grabbed her hips and pulled her powerfully up, manhandling the petite brunette to pull her onto her knees doggy style, arms crossed in front of her to each bed post as she leaned down onto her intersecting elbows, letting her back sink down and legs spread in obedient readiness for him to fuck her. She waited mere moments as Josh grabbed her waist again and inserted his cock into her, easily sinking right back inside her slick pussy and resuming his rhythm as she moaned in pleasure again.
She loved being fucked doggy style, getting hit from behind meant his cock was in just the right place to stroke over her G-spot and drive her climax. His grip pulled back intently into her hips, squeezing the pinch of her body to hold her strongly, in just the right position for him to smash into her, which he set about doing with a hard, fast pace, hips slapping into her firm ass as his cock pounded into her hot, silky hole. He was breathing hard now, almost growling with exertion as he slammed into her, her pussy feeling exquisite around his rock hard cock, the stiffest he'd been in years he thought as he pumped into the delectable Anna Kendrick. He'd wanted to do this to her for years, what men that knew he didn't frankly, and now he had the chance he was making the most of it, pounding her intently doggy style His muscles burned with the tension and energy, unable to keep it going but not ready to come just yet. Slowing down, he gave a few full length strokes of himself into her, seeing her relax as she let her muscles unwind a little from bracing herself against him, before he slid it fully back into her and leaned over, wrapping his arms around her.
She was a little perplexed for a second until he rolled to the side, taking her with him to pull her down onto her side, hands pulling at the straps as she fumbled herself into position. His hands slid back down her body to her waist again, holding above her hips as he leaned back, Anna pulling her legs up so he could start fucking her again, his lovely cock sliding in and out of her again as they both felt the relief of rest and enjoyment of sex. Anna had more freedom now and settled comfortably, arching her back to push her bum towards him and give him maximum access as he thrust into her, pushing in yet another new angle to make them both tingle. It was more than enough to finish her off, her orgasm having been bubbling almost covertly as he smashed her hard, ratcheting up but held at bay by her focus on simply enduring his primal energy as he took it out on her slender body.
Now she was more relaxed it overtook her quickly, rushing up on her with his renewed angle on her G-spot, pushing perfectly over it as she frustratedly tried to reach down for her clit to finish it off, grumbling even as she groaned, having to wait for him to just finish it himself using his cock. Luckily for her it didn't take long, another minute or so of thrusting getting the job done to make her tense and quiver in another climax, body shaking and shuddering as she gave an almost overloaded groan of ecstasy. She was almost done now, fucked out for the night, but it was up to him to dictate when they were done. Her tight pussy squeezing and gripping at him didn't help delay that however and he knew he was close, wanting to finish it differently however as he gave a few more thrusts and pulled out.
“Get up, on your knees,” he said, rolling away from her onto his back.
“What, my knees?” she mumbled confusedly, mind still reeling as she breathed heavily to recover from light headedness.
“Yes kneel up,” he commanded. Anna was sluggish, stretching a little as she started to move.
“Come on, quickly,” he ordered, reaching out to lay a hard spank on her ass, not in a playful manner but one of discipline. She jumped and immediately got moving, mind focussed as she pulled herself over and onto her knees, shuffling forward on the bed to get up, wrists cross in front of her as he immediately pulled in close to her and grabbed her leg. She immediately grasped what he wanted, lifting her leg and balancing to let him clamber underneath her, getting into place so she straddled him, reaching down to hold his stiff cock up for her to take a seat on as he guided her hips back. It was a new sensation for Anna as she let herself be directed to ride him, going cowgirl without control as she felt his cock contact her slick lips and then sit straight down on him to bury his cock inside her again.
He groaned deeply in pleasure as he reached up to squeeze her lovely tits, Anna starting to ride a little awkwardly since she couldn't lean down, holding her restrained wrists out in front of her as she bounced up and down. His hands roamed over her body as he worked his hips in unison with her, getting his whole cock inside her sweet hole and immediately feeling the tingle, happy he'd put her through her paces and wanting to finish now.
“Faster,” he commanded, smacking at the side of her ass, Anna immediately responding to the command and riding harder, working her pussy every way she knew how with squeezes and grips at him as she rode fast, keeping him deeper inside her and stimulating every inch of his manhood. He couldn't hold back any longer, giving a few hard thrusts up into her as his cock swelled inside her, a few pumps of finality before he erupted again, hauling the actress down deep onto him to empty his balls as deep as possible inside her. Anna groaned with pleasure as he came, squeezing her muscles to encourage every little bit out of him as he jumped inside her, always loving the feeling of men climaxing in her pussy. He gave a final clench of his muscles before relaxing, hands loose at her hips, both of them breathing intensely to catch up in the wake of another vigorous fuck session.
“Fuck that was good,” she breathed, having enjoyed every moment of it, something new and exciting for her.
“Yeah it was,” he smiled, unable to deny her simple statement. Another moment or two of recovery ensued before he pushed her off him, rolling Anna back onto the bed beside him, her hands untwisting at last as she flopped back onto the bed. Pulling himself up, he wanted to finish with one last thing and quickly swung onto his knees beside her, hopping close and grabbing her hair as he pulled his still hard cock to her mouth, slick with a mixture of their juices.
“Hey what the...” she mumbled, trying to protest but he was in her mouth, driving his cock deeply towards her throat before she could stop him. He managed to get almost all the way in, fingers twisting in her brunette locks as she gagged, unable to pull away as he held himself in her mouth.
“Suck,” he commanded clearly. Anna fought back a wave of displeasure and anger, hating this; she never sucked guys after they'd been fucking her, well definitely not after they'd finished, and it took all her control not to fight him. He had her though, and she had no choice, gagging still even as she started sucking, applying her tongue to taste their combined flavour as she snorted hard through her nose as her body tried to expel him. He held her for a few seconds, making her suck him completely before he released her and pulled out, leaving her choking and coughing in his wake as he flopped back onto the bed beside her.
“I fucking hate that,” she pouted, rolling onto her back beside him.
“I don't care,” he said calmly after a moment. With their session done, he turned and released her hand from the cuff, doing the same with the other one so she could lower her arms with a relieved groan, reaching up to pull the blindfold off and chucking it aside as she looked at him with her bloodshot eyes, make-up smeared all over her cheeks in the wake of her tears.
“I'm gonna go clean up,” she muttered quietly, pulling herself exhaustedly from the bed and heading for the bathroom. She spent a few minutes getting herself sorted out, wiping away the ruined make-up from her pretty face and composing herself before heading back to bed with him. He took a few minutes to get ready himself and joined her back in bed, sliding in beside her and drawing her close to cuddle up to him. She hadn't expected it, but it was a nice surprise and it helped her trust even more than he was clearly separating their personal relationship from what she was letting him do to her sexually. It took just a few moments until they both drifted off for much needed sleep.
* * *
The next day continued much as the previous evening had; after a long, surprisingly satisfying sleep they woke up and shared a shower together to freshen up, which involved a lot of stroking over one another as they washed each other down, his hands exploring her wet, silky body as if he'd never seen her before. As the water cascaded over them, he pushed her down to her knees, the diminutive actress sinking carefully down before him and obediently stroking at his cock. She knew exactly what he wanted, his rock hard cock straining in her dainty hand as she worked him a second before opening her mouth to swallow him. He let her get started, bobbing her head nicely and letting him slide right to the back of her mouth again, just teasingly ready for what he wanted from her. He let her enjoy herself, getting into the blowjob and rocking her head to push him into her soft cheeks, lapping her tongue around his shaft before he took control.
His hands slid into her wet hair to take hold of her, stabilising his target before he pushed down deeply to stretch her throat and make her immediately choke. Anna still wasn't remotely used to being treated like this, she was still fighting herself as he took charge and aimed to get his whole cock down her throat, but she was trying. Keeping her hands down on her legs, she tensed her hands as he did everything he had the night before but with more intensity, thrusting it hard into her throat, working with her gag reflex to catch her throat when it was open and slide his whole cock into her. Anna choked and coughed, gagging emptily around his cock as he used her, not fighting him despite her urge to as he blissfully face fucked her. The feel of her constricting and clenching around him, the wet sounds of her chokes and coughs combined with her evident complicity in events only helped to turn him on more. He didn't finish with her, deciding that a few full depth drives into her throat, holding her nose to him as she struggled and gave muffled complaints was enough, making her swallow him completely before he pulled out and released her. Anna coughed and choked again, having done better than the previous night but still struggling as she spat a thick string of saliva onto the floor of the shower, washing away easily as he stepped out past her, giving her a moment to wash her face off before shutting it off and following him.
Drying off with a crisp towel left her barefaced with damp hair, drying it enough to get back into the action with him, letting him lead her back to the bed where his rock hard cock awaited her.
“What's next?” she asked, sliding onto the bed as he grabbed something from his drawer.
“Anal,” he said simply as he turned back to her with a bottle of lube in his hands, Anna's eyes widening.
“Anal sex?” she repeated, as if she hadn't heard him, heart rate suddenly increasing as she contemplated it.
“Yes,” he replied, leaving no room for debate.
“I've never done anal before,” she replied meekly, eyes fixing onto the bottle again.
“Well, time for that to change,” he said, sliding onto the bed beside her.
“I...it's gonna hurt though, I don't know what I'm doing,” she said, not really wanting to go through with it.
“Well I'm gonna show you as I fuck you in the ass, now roll over,” he said, the conversation over, Anna realising what she'd got herself into by promising to let him do anything with her for the weekend. She hesitated, biting her lip cutely before the relented and turned over onto her knees, assuming a good doggy style position for him. He got in place behind her, rock hard cock standing up and straining in readiness, his own excitement the inverse of her trepidation as he prepared to fuck Anna Kendrick in the ass for her first ever anal experience. Pushing his cock down under her pussy, he let his bulging head slip teasingly over her silky smooth pussy, shaft rubbing her clit as he uncapped the bottle of lube and squeezed it thickly onto his fingers. Spreading her ass with his other hand, he pushed his slick fingers down over her tight back door, making her flinch at the cool lubricant as he spread it around her asshole. He testingly pushed a finger into her, easily popping through before the actress immediately flinched, clenching and pulling forward so he slipped out again, not at all ready.
“Calm down Anna,” he said coolly, knowing she needed to get used to that if he was going to ease his cock inside her. He added some more lube to her ass before pushing his finger in again, only for her to flinch again and immediately pull away from him with a murmur.
“Anna, you need to relax and take this, otherwise it's gonna seriously hurt when I push my cock in there,” he said, sighing. He was gonna fuck her ass, no doubt about that, but he didn't want her to hate the experience if possible.
“I can't,” she said, head dropped towards the bed.
“You can, just push gently as I push in, you'll take it fine and let my finger in there,” he reassured her. She tried to take in what he was saying, willing herself to stay calm as he rubbed her again before trying to push his finger; Anna managed to stay relaxed for a few moments, his finger probing her tightest hole before she tensed again and squeezed him back out.
“Come on Anna, let me get my finger in there,” he said, a little exasperated as she seemed to be taking it fine only to suddenly fight him again.
“I don't want your finger in there, I just want your cock!” she snapped, letting on her true feelings about it. She was resigned almost to doing it, but she just wanted to get on with it now and have him fuck her ass.
“Fine then!” he expressed firmly, leaning up and grabbing the lube, squeezing more of it onto his fingers and reaching down to spread it over his throbbing erection as Anna's nerves went through the roof, realising she'd pushed him to the point where he would do just what she'd asked. With the lube spread over his hard cock he grabbed the base of it and her waist, pulling back into her hip to stop her escaping as he pushed himself up against her asshole, his slick head bumping against her tight ring. He didn't say a word as he lined himself up with her, braced himself and then pushed forward powerfully with his hips; she wasn't the first girl he'd introduced to anal sex and he knew how to start it, pushing firmly but not too fast, getting the tip of himself into her tight hole to make it give way under the power of his hips. There was a moment where nothing happened, Anna being pulled back into his driving cock, her asshole all that prevented her progress for a second when it suddenly stretched, expanding around his thick head, the lube denying any resistance and letting it slide inside her...with a sharp bolt of pain.
“No, no,” she mumbled through a strained grunt of pain as her sphincter was stretched open aggressively by him, pain stabbing through her tightest hole as his cock drove it open, pulling forward to get away from him. He didn't pay any attention however and kept on driving, knowing he needed to get it inside her, sinking himself halfway into her as he shuddered in pleasure at the beautifully constrained tightness of her around him. He tried to stay with her but Anna pulled forwards with instinctive strength, a fight-or-flight response as she yanked herself out of his grip to get his cock out of her ass.
“I fucking told you, Anna,” he said brusquely, laying a hard smack on her ass to make her clench and howl, a properly hard spank to discipline her. Yanking her back with her hip, he reset her prone position in front of him.
“Now, do as you're told,” he said, digging his hand into her waist and block her hip, holding her harder this time, knowing she would fight him again it seemed as he pushed his slick cock back to her asshole. Gripping himself tightly, he positioned himself against her sphincter and then surprised her painfully with a sudden, sharp thrust forward, giving her muscles no chance to obstruct him as he buried himself into her reluctant booty and drove as deep as he could get before she tightened up around him in an agonising spasm. Anna squealed in pain as she was aggressively penetrated, the loss of her anal virginity proving agonising in that moment as she again tried to yank forward and free herself, only to find herself held by him, his hand digging into her waist as his other one grabbed into her long, dark hair to haul her back into him and give her no way to escape.
“Fuck!” she shouted to the bedroom, her ass held open, sphincter twitching sharply as she struggled to cope, unable to fight the pain; trying to relax didn't help but squeezing at all to try and reset herself somewhat just made it worse, having to just endure.
“Shut up Anna, it's not that bad,” he said dismissively, even though he knew it was hurting her badly. He hadn't wanted it to be that way but she'd given him no choice but to force his manhood into her and break her ass.
“Easy for you to say,” she grimaced, digging her fingers into the bed as he pushed again to bury more of himself inside her, not wanting to pull back just yet as he knew her overwhelmed body would push him back out again if he got near her tight muscular ring.
“If you'd worked with me it'd be easier,” Josh said, pointing out that she hadn't listened to him. She had to concede maybe she should have, even though she wouldn't admit it as the pain subsided somewhat, tension releasing to let him push into her a bit more. Trusting her a little, he pulled himself back, feeling her squeezing and twitching at him as she fought her desire to clench down, super sensitive as he pulled his thick cock back out of her, not risking going too far before he sank his pelvis forward again to bury it inside her again. She impressed him by managing to control herself again so quickly, managing to stop her body reacting against her will as he slid his slick cock all the way inside her, burying himself balls deep in her ass so his pelvis pressed into her.
“Ohh fuck that's it, good girl,” he groaned, erection flexing hard inside her as a tingle of ecstasy spread through him, shivering at having got balls deep inside Anna. As she tried to relax her body tightened again and she clenched on him, far too hard, sending another bolt of pain through her. Her sphincter was strained now, having been pulled as he'd driven into her which would hurt for a couple of days and as she clenched up it only made it worse. She gave another grunt of pain, whimpering a little as it endured, tears pricking her eyes. His grip on her softened, taking it easier on her hips though still dominant, Anna knowing full well he was in charge as he pulled his cock back again and slid into her, her body twitching as she tried to get used to it, the first anal sex of her life. It still hurt though, feeling the stretch even as his lubed cock slid quite easily in and out of her, starting to build up a slow, deep rhythm, tears that pricked her eyes rolling down her cheeks as she dug her fingers into the bed and dropped her head.
“Fuck that's tight,” he breathed as he started to fuck her, her immediate resistance broken to allow him to fuck her, pumping his hard cock in and out of her, pulling back till the head was just inside her before burying it again, making sure to push his hips into her toned booty every time. He was in paradise, loving that he'd cracked Anna's ass and now he had the blissful sensation of her squeezed tightly around him, totally at his mercy and he had to admit the struggle had only made it hotter. He didn't want to hurt her, but he wanted to fuck her in the ass more. Pumping briskly, he picked up the pace, starting to thump against her bum, hips moving smoothly back and forth as he fed her his cock, getting a bit more brave on the pull back, feeling her working with him so he could let his head pull back into the tight stretch of her asshole just enough before driving home again. It felt fantastic and he was thoroughly enjoying himself, Anna seeming to get used to it and be taking it fine until he pulled back just a fraction too far and her muscles pushed him out, thrusting at fresh air.
“God damn it,” he muttered even as he reached down to grab himself, aiming it into her stretched asshole and driving in once more with absolute resolve, making Anna cry and flinch again, pulling forward and threatening to pop him out again, hot tears pricking her eyes and rolling down her face again, body giving a little shudder. His cock flexed inside her and she knew he was loving it, enjoying her pain even if he didn't quite mean to, making her seethe but also tremble in arousal. She loved that he was taking such pleasure from her body, even if she wasn't. She was however incredibly wet, pussy giving away her arousal as he fucked her ass, not that he was paying any attention to her wants or needs just now. Staying deeper now he fucked hard, making her brace herself under him as she felt him pick up the pace, knowing he was going for climax, which didn't bother her at all as her ass hurt and she really just wanted a break.