Breaking Anna

Hey everyone,

This is the sequel to my previous story "Blackmailing Anna" ( https://literotica.com/s/blackmailing-anna). I would recommend reading that first as the pacing here is otherwise a bit fast. I wasn't planning on writing a sequel but the response I got to the last one was great, so I decided to!

I'm aware that an 18-month turnaround for a story is... Longer than some people would hope ;) But life got in the way so hopefully better late than never.

I'd like to also thank a number of girls on various chatrooms and message boards for their thoughts an input both whilst writing this and in RPing out possible ideas.

If you enjoyed the story, please do leave a comment. I read them!

And if you really like it, you're welcome to reach out to me via my profile.

In particular, I'd love to release an audio version of the two Anna stories. So if you're a girl with a pretty voice and want to try something a bit out of your comfort zone, reach out to me :)

Enjoy the story,

J

____________________________

He looked Anna up and down, his eyes almost able to tear through the thin dress fabric covering her body, naked underneath. Anna stepped out of the elevator, dizzy, barely able to keep her ballance. He stood there savouring every ounce of Anna's nervousness. She felt like a deer in the headlights. This wasn't a chat-box on a computer any more. This, and he, were real. Did he know that only moments before she'd had her fingers in her pussy thinking about him? There was no way he could know...

After a few steps, she stopped and, gathering her courage, saying

"Well... I'm here. You'll get what you want. to fuck me. I don't have a choice, you've got me, but just tonight. Just one time and then you delete everything you have of me."

Bargaining, a voice in Anna's head said. That was the first step towards something, she loosely recalled from her college psychology class, admonishing herself for her transparency.

He was on the taller side with dark hair and a well kept beard. Early to mid 30s she'd guess, though he could be older. He took his time to reply, smiling at her comment and taking a sip from the glass in his hand. The irony, at least as Anna saw it, was that if a man like him had approached her at a bar, especially dressed the way he was exuding the same level of confidence, she could see herself going home with him.

In a way that made it worse, she thought. A man like him, good looking, confident, obviously rich given this penthouse would have little trouble picking up whatever kind of women he wanted. That means he was doing this because he liked it. He liked something about this fucked up circus. Maybe he liked having a girl that couldn't say no. Maybe he liked how hard girls like her came when being forced. Maybe the kind of power he had over her... Not that she totally disliked it. She couldn't say that it hadn't turned her on, as the dozen times she's fucked herself thinking about him had proven. But that was fantasy. Reality. This very present reality. That was something else.

He finished the sip and shook his head a little, as if Anna had missed something blindingly obvious, He replied

"Your mistake there, Anna, is thinking you're in any place to start making demands... I'll have you tonight. Then again any other time if I want it."

She looked down, he was right of course.

"Should I... Should I take my dress off?" she said, mustering as much defiance and integrity as possible when offering to strip for the man blackmailing you.

He smiled again, too charming a smile for a man blackmailing her into this situation, as he put his drink down and started walking towards Anna. She reached up to slide the strap over her shoulder, but his hand caught and stopped her.

He spoke softly, "There's no rush... I'll have you naked in due course, but I want to take my time tonight. You see, I can get inside your pussy any time I want, what's a lot more fun is getting inside your head." He took another sip from the glass and set it down on the side. "Come with me," he said and turned.

Anna empathized with a gazelle caught in the jaws of a sadistic lion that liked to play with its food as he led her by the small of her back to the balcony. The cool air was bracing, especially given her lack of underwear, and a soft midnight breeze caressed her inner thigh.

"How many girls have you done this to?" asked Anna "I have a feeling I'm not your first..."

"You're not the first. I've hacked maybe one or two dozen girls. For most, I don't get half as interesting leverage, though. A girl will suck your cock to stop dull vanilla nudes from getting out there, but she won't do much more. Certainly not enough to get her to do what I'm going to do to you..."

He was so matter of fact. The same tone with which one might idly speculate about the weather or an upcoming sports game of minor interest. Silence hung in the air and the wind brushed Anna's hair across her face. He reached over, gently tucked her hair behind her ear and continued.

"I've made proper fucktoys out of four or five girls. Some of them I still sleep with from time to time. But I think you have the potential to top them all, Anna..." his voice returning to the playful tone. "Such a proper girl to the world with such twisted fantasies. I've never found a girl who fucks herself so eagerly to non-con porn, but with so much to loose if the world found out. This good girl act you keep up, it's honestly quite adorable. And, to top it all off, being forced into all this makes you cum like the little slut you are. The perfect girl next door who's never happier than when she's being used against her will as my personal fucktoy."

"Stop using that word," she said.

"Fucktoy?" he clarified.

Anna nodded.

"Why?" he asked.

"It's demeaning. Objectifying. I can't stop you from fucking me but I'm not your toy."

He chuckled, then continued.

"You're predictable, Anna. Your submissive desires led you here and now the loss of control makes you want it even more." He traced a finger down her hairline, sliding it behind her ear, then shoulder. "And realizing you want it makes you feel guilty..." he kissed her neck and Anna let out a moan, then turned red as she realized. "But the guilt turns you on even more." Her hands came to his chest as his kisses found their way to her collar bone. Her pussy clearly hadn't got the memo that they weren't going to let this man have whatever he waned. He slipped the dress straps over her shoulders and the material hung between them on her breasts, slipping with each moment. He brought his hands up to her sides, catching the dress before it fell, and looked her in the eyes. Not breaking contact he whispered "You're mine, Anna." He let go of the dress and kissed Anna deeply, passionately on the lips. The night air and his strong hands swirled around and explored her young, athletic body.

She could almost forget how she got here as Anna had one of the most memorable kisses of her life. She'd heard some women could even orgasm from a kiss. Anna had always been sceptical, but the way he was kissing her now made her reassess that possibility. Not that she was going to but fuck, if anyone could make her just with a kiss, it would be him.

But then she remembered her situation. She wasn't going to let him break her so easily and she tried to pull away a little but the resistance just spurred him on. His hand came to her neck. She felt so vulnerable.

He broke off the kiss and looked her in the eyes "Good. This wouldn't be fun if you put up no resistance."

He kissed her again. More forceful. More demanding. Her hands tried to push him away but her hips involuntarily bucked forwards. He reached down with his spare hand. Her dress had risen up a little giving him access to Anna's tight, wet pussy. His right hand still on Anna's neck, he made pressing downward motions on Anna's clit, one way she often plays with herself.

Anna realised that he clearly knows how she masturbates. He must have made notes or something from the videos. Was that fucked up or hot? Anna wasn't sure.

Anna wouldn't even have been able to count to ten before her hips were bucking on his fingers and she moaned into his kiss. Her hands balled into his shirt, still trying to put up some resistance, as she started to gyrate her hips on his fingers.

She could feel her incoming orgasm, like a scratch on her back just out of reach. The rising pitch of her moans clearly gave it away as he said "Remember the rules, kitten..."

"Ple..." the words almost fell out of Anna's mouth but she caught herself "No. I'm not going to beg you. I'm here you can fuck me all you want, but I won't degrade myself."

He simply laughed and released his grip on her. Anna gripped at the balustrations to steady herself, taking deep breaths to regain her senses.

"Why do you like denying me like that?" she asked, a pinch of anger in her voice.

"Why do you think, kitten?"

"I don't know. You want me to humiliate myself? Well I won't. You think making me beg will justify this? It doesn't. You're a sick twisted man. You can fuck me, I can't stop you. But I won't give you the satisfaction of this humiliation."

Silence hung for a moment.

"You begged for me before," he retorted simply, "and you will again tonight. I don't just want to fuck you, Anna. I want to get inside your head. I want to break you. I want to dominate you so personally that you can't even have a sexual thought without thinking about me. By the end of tonight you'll learn what true submission feels like." and with that he turned to walk inside.

Anna had nothing to say. The rational part of her brain was enraged at what he's said, the audacity of it. She wasn't going to let him do that to her. But Anna wasn't fully governed by her rational brain tonight and hearing those words from him had left her pussy dripping. Unsure of herself, she followed him in.

Stepping back in from the night air, Anna followed him through the main room of the suite. As he entered the bedroom on the side he said "pick my drink up on the way". Anna stopped, looked around for the drink and collected it for him from the side. This must really be every man's dream, a hot young girl strolling naked into his bedroom bringing him a double scotch and ice. Of everything she expected to be tonight, a waitrace was not one of them. The room had a luxurious king bed. He'd taken off his shirt whilst she was out and it was now thrown on the bed. His back was turned as he inspected an array of objects on the side table. Where he was, she couldn't see what these things were.

Anna simply stood there, waiting, before he turned and walked towards her. She held out his drink and he took it, then took a sip.

"You're going to suck my cock now, Anna. You're going to give me the most enthusiastic blowjob of your life. At the end I'm going to cum in your mouth, and you're going to swallow every drop." He was again so matter of fact, but she could now hear just a little of the lust in his voice. Apparently the naked sexy waitress look did it for him.

She'd given up trying to fight her situation. She'd resigned herself to merely fighting against wanting to do everything he told him to do. "Ok..." was all Anna managed.

She took two steps towards him and began to bend her knees and drop. As she started to squat, He caught her, turning her up to face him. He lifted her back to her feet and kissed her, his hand coming to her neck again in that just slightly threatening manner.

He broke off the kiss and looked at her. "Eye contact, kitten."

She nodded and began to descend again, this time looking into his eyes, placing her hands on his bare chest to steady herself as she went down. She struggled with the belt as she dared not take her eyes off of his, so he reached down and unclipped it. As he slipped the belt out of the loops, Anna unbuttoned the front of his trousers and slipped them, and his underwear, to the floor.

Anna didn't reply. She simply opened her lips and took him into her mouth.

She took perhaps half of his length in her mouth first and held it there for a moment. Her eyes remained locked to his and Anna fluttered her tongue on his shaft, inside her mouth. Her head started bobbing up and down, her tongue running lengths along his cock and she did. She sped up, trying to reach the midpoint of his cock with every stroke. She tried to let her lips do the work as well as her tongue. Just pursed enough that he felt resistance against his cock but loose enough to slide with her motions.

Most men at this point would be putty in Anna's hands. Anna knew how to suck cock and how to do it well. Some girls have a face to launch a thousand ships, but Anna's lips could launch a million. Just a short blowjob and most partners would be all eager to please her. But not Him. It was clear who had the power here. Sure, there was lust in his eyes, but also much more... A kind of arrogant command that made Anna almost want his approval.

But that gave Anna the idea. She'd try and play his game back at him, pretend to be the slut he wanted her to be to claim some kind of advantage. If she could make him cum like she could other guys, maybe she'd have some influence and control here. She's give him what he wants, or at least make him think he had it.

Anna opened her mouth and slid his cock out along her tongue. She put her hand round the middle of the shaft and began to slowly stroke his length.

"I can't deny you make me horny..." she whispered, leaning in to kiss the tip of his cock. This wasn't a total lie, though her sultry tone was more acted than authentic.

"I can't stop cumming thinking about what you did to me the other night," she continued, her voice sex-soaked with seduction. He smiled a little at this and took another sip from his drink, Anna dared not hope that it was working, that she was getting into his head. More likely, she thought, he saw right through her acting but wanted to let it play out.

"You've got all the power here..." another soft kiss on his cock-head, her fingers still working the base.

"You can have me anytime you want and I'll cum for you every time..." she planted three kisses, one on the middle of his shaft, one just where his head ended and one closer to the tip.

These were all lies, she told herself as she slid her fingers up along his shaft. She was just playing the game. But the feeling between her legs began to tell a different story.

Anna put both her hands behind her back. She wanted to do this just with her mouth. She looked up into his eyes and spoke three words to summarize her submission.

"You..." she softly kissed the head of his cock.

"Own..." a second kiss, this one on the side.

"Me..." with the third Anna didn't simply kiss his cock. She opened her mouth just a little more and took just half of the head of his cock in, sucking on it softly.

Anna continued, not breaking eye contact as her mouth went further each time.

"Damn, Kitten..." she heard him say quietly.

Anna wondered what this looked like, felt like, from his perspective. To have watched her for months and now to have her here. It made her appreciate his patience. The self control it must take not to fuck her right away like most men would. She wondered if her boobs looked good from that angle. She took his cock out of her mouth and continued with a hand for a moment. He was about to say something before she leaned back a little, giving him a clear view of her chest. He smiled, reached down and touched them, then, bringing his hand to her chin, guided her mouth back to his cock.

Anna knew this was her best opportunity to try and win back some kind of sexual power here. She readied herself and took his whole length into her mouth. Anna's deepthroat caused him to let out a moan, which Anna couldn't deny made her a little pleased. She wanted to tell herself that this was just because of the small amount of control that she'd won back, but the lie rang hollow even to herself. It's possible she could've gone too deep trying to sell the seduction and some part of her was pleased to be pleasing him.

She broke eye contact to focus on bobbing her head deep on his cock. He didn't object and ran a hand through her hair, drinking occasionally from the glass in his other. This was gentle at first but was soon thrusting into Anna's movements. Anna tried to feel his rhythm, as clear as it was forceful, and starting to dance her tongue on his cock to match him. She reached up and under with one hand, running fingers along his balls. With the other hand she reached straight up and touched his chest.

His cock was throbbing more and his breathing getting deeper. If Anna could make him cum like this, maybe the tables would turn a little.

He laughed a little, reaching down, putting his thumb on Anna's chin and fingers on her neck. He guided her up and off his cock, then slipped a finger into her mouth. She sucked as he slipped it out.

"Well that was definitely well done, kitten... " He said, forcing an involuntary smile across Anna's face. What could Anna say? There's something about a guy telling a girl that she can suck cock well that'll always make her feel proud, irrespective of the fucked up context.

He placed his glass on the side, reached down and pulled her up to her feet, then lifted her by her sides and threw her to the bed. Damn the guy was strong. He pulled her to the side, Anna's head hanging over the edge a little as she lay on her back, and he stood by her and fed his cock back into her mouth. His right hand would alternate between running its fingers through Anna's soft hair and grabbing hold tight so that he could push his thick cock deep into her mouth. All the while, his left hand worked wonders between her legs.

He toyed with her pussy, avoiding her clit but giving her pretty inner lips and hole all the attention they needed. From masturbating in the elevator up to here to his kissing to the way he'd jilled her on the balcony, Anna was soaking wet. She was quickly becoming the desperate needy slut he wanted her to be - so much for her blowjob skills gaining her back some control.

In his rougher moments, Anna wasn't even actively sucking his cock. She'd been reduced to a simple face to fuck as she allowed her body to be used however he wanted. But she could feel the orgasm coming. That amazing climax that would clear the fog from her desire-addled brain and let her think. Then she remembered his instructions about permission. Fuck.

Anna looked up to him with pleading eyes, no words needed, and he simply shook his head before spanking her pussy. The pain pushed the orgasm down but nevertheless made her hotter, hornier.

He continued like this. Anna doing her best to suck his cock during the softer moments between bouts of intense throat fucking. Him toying with her pussy, then spanking to drive away the orgasm. Twice he spanked her pussy, but the third he pulled his cock out of her mouth and slapped her face, causing Anna to moan. That was already on her kink-list, as his intimate knowledge of her private search history ensured that he knew. But with each passing moment his own moans grew louder and deeper, too. It turns out, thought Anna, that you can only have your cock in a pretty girl's mouth for so long before you need to cum down his throat. The final spank was clearly aimed at her pussy, but he was distracted by the pleasure of her mouth and missed a little. It hit her left thigh at an angle, the pain not quite as bad, not quite as distracting, and especially nice as his hand followed the momentum back to her pussy, touching her again right away. Anna had to fight her hardest not to cum that moment but mustered just enough self control. He seemed to realize the position he'd put her in and removed his hand quickly, something Anna was thankful for as she would not have lasted even seconds longer.