Big Boss's First Submission

It is not that she showed up unprepared to the meetings. She knew as much as everyone in the room did. It is rather that she expected to be treated as an equal. The bar is low, no? But their basic patriarchal brains could only process her as a relative. At best, as an intern. They angered her, and, unfortunately, she let them see it.

The biggest offender had predictably been the most senior figure in that room. A classic case of man whose path to self-fulfillment only included women as progenitors or as eye candy. It's not that they were in antagonistic roles, nor that he made particularly boomerish comments. Really, it was that he had a way of deflecting the conversation every time she moved it an inch forward. He was fast at destroying progress she had built up over several exchanges. Somehow, though, it did not feel intentional. Maybe he just did not give a fuck.

She was so furious that evening that she worked after hours to try and prepare for round two of negotiations. She felt that, if only she could prepare more responses to each deflected talking point, she could still win them over. It was a bit desperate, in all honesty, but the situation was dire with her job on the line. She had not changed out of her work clothes when she sat down at the hotel bar for dinner in front of her laptop. She figured her counterparts would be going out for dinner and lounging instead.

When she heard a chair slide in one of the tables near her, she looked up from her documents. It was the biggest offender, the senior figure, the man in his 50s who thought she was an intern despite her incipient wrinkles and plentiful white hairs. She seethed. Like her, he was still in business clothes, though his tie and blazer were gone. He nodded and lifted his left hand to do a single wave at her, or perhaps to show that he was not wearing a ring. She just nodded and looked back into her computer.

She had to guess what made for a natural scrolling speed because, at this point, she was unable to keep reading. The strong sensations she felt, perhaps led by fury, distracted her from negotiation paths and carefully crafted rebuttals. How could her desire to take over be so strong, but not strong enough to let her focus? They were going to eat her up and she would return home empty-handed.

But the end of her misery would arrive early, completely unexpected. A waiter placed a cosmo on her table. A cosmo? On her table? She had not ordered a drink. She would never order a cosmo. She looked at big boss, who smirked, lifting his own classic martini to her before he sipped from it.

This man was playing with fire -- the kind fed by intergenerational resentment and ignited by one too many injustices. She, the fearful kid who cried silently when teased in school, the good woman pouring her free time into her community, the perpetual submissive in bed: she was going to fucking destroy him and tricking him into loving it.

She looked at the cosmo and then she shifted in her seat to angle herself towards him, looking into his eyes. Her shoulders and knees and hipbones pointed towards him, but her face remained cold and emotionless.

"In my company, you would have to hand in your resignation over this tomorrow."

His smirk faded just for a second, perhaps shocked by the intern who dared to speak up against a stupid drink. Was his name going to appear on some bullshit MeToo account on Twitter?

"I guess it is good that I am the boss in my company."

She stood up, maybe an inch or two straighter than usual. She grabbed the cosmo and walked slow bur firm towards his table. He flinched, even if just for one second: she was tall and, in her 3 inch stilettos, she was towering over his seated figure. She stood a few inches too close and looked down at him -- her soft features hardened by her dark hair in a tight updo, by the black blazer and skirt tailored tight against her curves in front of him.

Maybe he thought he would have to wash a cosmo off his shirt, or that he would feel the slap of her long fingers. He couldn't possibly expect this sociopathic millennial to just sit down and drink with him. In reality, she just put the cosmo down on his table, and grabbed his martini instead.

"Next time you buy a drink, buy her the correct one. There is no need to mess up from the start."

She walked back to her table with his drink and looked into his eyes while she sipped from it. No smiles, no emotions. Big boss had lost the first round. She went back to her computer.

To his credit, he did not freak out. Though he did need a few minutes to collect himself while she worked. After all, it was now him dealing with an unpredictable script, the one forced to craft a careful rebuttal. He was the alpha and he had no option of leaving. Not if he wanted to protect his dignity.

This time, he got up and walked towards her high table, leaning on it. Big boss came in with a white flag in his hand, approachable, ready to make a concession.

"You know, you're right. I should have asked you what you would like to drink. Earlier, I should have let you lead the conversation. I misjudged you. I know it's not your job to give me a second chance, but I would really appreciate it if you did."

She looked at him, crossing her legs in her seat. Her pencil skirt wrinkled against her hips, baring a few inches of her thighs.

"You're right that it's not my job, and, to be honest, I don't have any reason to believe you will not mess up the second chance the same way you messed up the first one."

He pushed himself off her table, preparing a dignified exit. Little did he know that she would stretch out her arm and press her hand against the front pocket of his shirt. He looked at her, shocked. She grabbed his room key card, holding it briefly in her hands to look at the number penciled onto the paper envelope.

Ignoring him for a minute, she closed her laptop and put it into her purse, getting up from her seat. Before she walked away, she put the key back into his pocket.

"You get a second chance, which will also be your last one. I will try your door thirty minutes from now. I hope you will do your best to create a better impression."

True to her word, she tried his door exactly 30 minutes later. It was unlocked, of course. He was sitting at the desk, speaking on the phone, not even acknowledging her. She stood at the entrance, wearing the same stilettos, the same figure-fitting black suit, carrying the same black purse. With each exchange of his conversation, she regretted her decision exponentially. Alas, when she felt there had been one line too many, she turned to leave.

Except that was not how he had planned it. He hung up immediately and pushed the door closed when she opened it. He just wanted her to be off guard. Big boss hit first, kissing her lips and pressing her against the wall. She let him do it, she really bought into it. Her tongue pressed his lips apart as he undid her tight blazer, pushing her hips against his to encourage the growing bulge in his pants.

When his hands reached her ass, he picked her up, lifting her out of her stilettos. He just did not want her eyes to be level with his. He wanted her to look up at him. Again, she indulged him. She looked up at him, her figure less intimidating with her lipstick ruined, her breasts exposed, her shoes kicked away. She was just the intern, just the easy prey, the young slut whose holes would bring big boss some distraction and relief.

"So this is your last chance to impress me. You're starting to do better. What's your plan?"

He laughed. Was this one for real? Oh, to be a hot, bold, and entitled millennial. She was starting to piss him off.

"I don't know, I wonder if I can show you a good time. You certainly seem to really need it." His hands fondled her large ass, letting her flesh bounce, demeaning. "But I'm also thinking you might be more trouble than it's worth. Too harsh in the meeting room, too picky in the bar, too cocky for a slut that followed her client to his room. What will your boss think?"

In a swift move, she slid her foot between his legs and knocked him out of balance, forcing him against the same wall. He almost fell. Her hands held his wrists, pushing them above his head. Standing on her toes, she leaned in to nibble on his lip gently.

"That's a long way of saying you don't really have a plan. He will think your sorry ass tried to make a move on me and I turned you down. Plus you're probably going to blank when he asks you which of his employees did it."

Intrigued by the unusually tall and strong woman, he let her have this one. He stood there, pinned, wondering if he had in fact confused her name earlier. No, of course he hadn't. How could he have? But maybe he really had.

"I don't know about that, Anna. But I find it hot that you're ballsy."

"Are you that dumb that you don't even know how to read emails?"

Alright, maybe he had fucked up. Maybe he had discounted the underdog too early. Who the fuck was she and why was his cock harder than it had been on any given moment of the past few months? She was giving him serious blue balls. He stammered.

"I... I'm sorry. Is your name really not Anna?"

Affect theorists say that, in fear, one does not flee: one shrinks back. Big boss was second guessing his entire existence against her body, feeling small and defeated even if just for one moment. In holding him, she felt his hard cock press against her lower belly, an indication of where he wished his sperm would hit -- if only he had not messed up his chances. She looked into his eyes, pitiful.

"For you, no, my name is not Anna. Be respectful and call me Doctor."

She let go of his hands and they made out furiously, hungry like deprived lovers. Within the complicated feelings that this encounter had elicited, they both felt an identity-challenging amount of arousal. He liked straightforward sex with carefree women and she liked getting choked by people who otherwise saw her as their equal. They had no business in thirsting so hard for their nemesis, but here they were, and soon they were both naked in his bed.

In a more standard situation, he would be the one calling the shots and asserting his authority over her pleasure. He would eat her out, or he would drag her mouth down to his cock, but he did not know what was permissible with this obstinate lover. He might try something normal like touching her legs and she might melt down like an offended snowflake. Maybe she was right and he had no plan, after all.

It's a good thing that she came prepared better than everyone on that trip. She could see he was in need of reassurance, and she swapped the stick for the carrot. Her mouth around his cock was the carrot. She crawled between his legs, her hair still tightly pulled back, and she smiled at him when her hands approached his cock and balls. She slowly stuck her tongue out, lascivious. For the first time that evening, he felt desired, and he grunted loudly when her tongue lapped up his precum.

Her blowjob was meant to harden him, tease him, get him ready for her plans -- not to make him cum inside her. But he had no idea; he just felt the waves of increasing frustration every time her mouth desisted from a particularly effective motion. The damned cock tease couldn't even give him good head. It was truly a millennial slut paradox: she couldn't sustain him into the low-hanging fruit of the first orgasm, yet her tongue kept reaching his balls to brag how she could take his whole cock in the depths of her mouth. He needed to end it and take back control.

She was glad to hand it over to him. After tasting his frustration during one more edging, she let go of his cock and sat up in bed. Her thick thighs spread to reveal her, glistening and ready for his tongue. When he approached her, she pulled him by the neck, lest he got confused again. But he wasn't that thick, and he just needed a chance to shine.

He ate her eager and enthusiastically -- perhaps the most enthusiastically he had eaten any woman out in his life. This was more than just a ticket to fucking the youngest pussy he had had in years: he would deal with the chip on his shoulder for good once he had her shaking against his face. He licked, he fingered, he drank all her juices. He lasted much longer than he had ever lasted, or than he had ever had to last. But it was just not his day; despite his best attempts, her pleasure was simply not building up. Did she just shift, was she grabbing her phone? Why was she looking in her purse?

"Here. This might help you."

She threw him a vibrating dildo she had pulled out from her purse. He felt defeated. He struggled to even find out how to turn it on. Her grin was infuriating. Still, he persisted, and, with the extra mechanical aid, he gave her the first orgasm of the night. She came when his tongue circled her clit while the vibrator hit her g-spot.

When she came, his turn was over. She took out the vibrator and moved on top of him, replacing it with his dick. She was tight after that first orgasm, and in his state of deprivation, he knew he would cum in a matter of seconds. Just what he needed to prove himself on this god-awful date. Her hips moved up and down, rocking all the curves of her body in the sluttiest display his eyes had enjoyed in decades. The millennial whore knew the effect she had on him and she was enjoying herself at his cost.

"Don't you dare to cum. You're not a boy. You're meant to last longer than this."

He closed his eyes, trying to block out the image of her ample curves bouncing, the feel of her ass hitting his thighs with each of her movements. In the multiplicity of feelings his body could hold, he felt both ecstatic and ashamed. Her pussy felt just so good around him, unlike anything he could recall. But it was so good it was leading him into imminent embarrassment, and he had never felt so ashamed.

She sighed, exasperated, and got off his hips on the right second to avert disaster. He sighed in relief, his cock twitching.

"Get on top of me. I have an idea."

The trick up her sleeve seemed to be good old missionary, which would help him in his current state for a grand total of fifteen seconds, if he were lucky. But, at this point, he owed her nothing. He deserved to fill her little pussy with his cum and call it a night if he so wanted. So he got on top of her, heavy and strong, and he immediately started fucking her pussy. He had landed on a good angle and he felt it.

She grunted in approval, but that was not the trick at all. While he focused on trying not to cum, she grabbed the dildo, still coated in her juices, and pressed it against his ass. He froze.

"Hey there, no. No ass play for me."

"This is not ass play. This is not about your ass. This is about making you last longer."

Her hands pulled his cheeks apart while she inserted the head of the dildo in him. He did freak out. He did not stop her. He was not in pain but maybe he was in shock. He stopped moving inside her.

"I did not say you could stop moving."

Maybe this was a little too much stick after not enough carrot, but it was not enough to break him down. He was... distracted, to say the least. And conflicted. He both lost his boner and regained it that very minute. This is not how it was all supposed to go, but he was now inside her, and he'd find his release soon. He'd deal with her afterwards. He just needed to cum really bad. And so he blocked out what she was doing. He didn't care that she moved three inches of the dildo inside him as he fucked her, and he didn't care that it was slowing his own orgasm down. He kept moving. She was moaning.

"I'm so close, oh fuck I am so close... Don't you dare cum yet, I'm really gonna come around your cock if you keep going."

"Oh, baby, I don't know if I'm gonna make it, but I want to feel your tight little pussy come around me..."

Famous last words. She shoved one more inch in him in one go, painfully distracting him this time.

"Doctor. Have an ounce of respect and use the right title. Now hold the fucking dildo so I can focus on cumming."

She grabbed his right hand, making him collapse on top of her, and she moved it to the dildo. She held him in place until he started fucking himself while he fucked her. He was her bitch now, but she felt she could push his boundaries just a bit more.

"Alright. You are so close to making it. You're doing great. I'm gonna let you cum. All you need to do now is look in my eyes and count down from fifteen. You can cum when you make it down to one."

This fucking sociopath. His dignity hated her, but his dick loved her. At this point, so far into the game, it cost him nothing to obey this one last command. Determined, he looked into her eyes and began counting down from fifteen, his hand struggling to coordinate the dildo strokes in his ass as he fucked her.

"Ten. You are getting close to paradise."

He closed his eyes to make it, and she let him get away with that one. It was only fair as it would compensate for how hard he was fucking his own ass throughout, the fastest ever convert to the church of ass play. As he hit the right angle, her insides squeezed him harder and harder. When he got to five, it was nearly impossible for him to utter more counts.

"Five."

She chimed in to help him. He was getting helpless.

"Four."

His sweaty body was practically stuck to hers, his hips bucking wildly to keep his strokes going.

"Three. Don't you cum yet. You are so close now."

"Two."

Big boss won the big boss fight, the last level. He exploded in the strongest, most intense, most Earth-shattering and identity-challenging orgasm he had ever experienced. He flooded her with his cum while his own ass clenched the dildo. He moaned so loud he screamed. It was over. She had made him her bitch.

She remained still, her legs wrapped around his waist, holding him in place while he recovered on top of her. He averted her gaze, unable to deal with the consequences, or maybe just unable to focus.

"Have you ever tasted your own cum?"

"Probably when I was young, why?"

"Because you never counted down to one and now you have to lick me clean."

The inconsiderate millennial left her slut man to his own devices. He would experience sub drop and the waves of shame all on his own, with no nurturing figure to remind him of his worth. He was a big boy, though, and he would probably be fine. She went straight to sleep when she got to her own room that night, but she played with herself after the second round of negotiations the day after.

It was not the image of him cumming with a dildo in his ass that pushed her over the edge. It was the recent memory of him finally calling her Doctor in front of his employees.