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The VC and the Mistress (Fiction)

The VC &  Mistress 


Was it destiny? According to Pat Nair there could be no doubt. His fortune teller in the Castro had told him that morning it was going to be a special day, one in which someone from the past might reappear, and that he should be prepared. Admittedly he had already put that piece of advice out of his mind by the time he met Nikita Malin in the San Francisco Centre shopping mall for their weekly gossip session. Of course the conversation turned, as always, to her love life, or rather lack of it.


“It’s so unfair,” she said as they peered through the smoky glass display window of a designer store at the ridiculously expensive pair of red suede Italian loafers that they both lusted after.


“He’d buy them for his wife, if she asked him! But I have to wait for him to give me presents that he chooses.”


Without taking his eyes of the shoes, Pat replied “You’ve had a sweet German sports car off him, and a sweet luxury apartment and a wardrobe full of clothes.”


“All right, he takes good care of me,” said Nikita. “But why do I have to wait for him all the time? I’m fed up with it. I’m twenty-six. I want a life!”


This was a line he’d heard a dozen times and he never found it convincing. Usually, out of friendship he commiserated with her, but today her words grated. Having lost his own benefactor the previous year and now working in a massage parlor in the Haight, struggling to keep afloat, he found it hard to sympathize with her poor little mistress number. 


“Well, you can always go back to your old life,” he said.


Nikita Malin was annoyed at this remark. Even though Pat Nair was her closest friend and confidant, he had no right to be unkind. She did not want to be reminded of what she had done or what she had had been. With a petulant swish of her young, lithe body, she turned and headed for the escalator.


Pat walked behind her and said, teasingly: “Don’t be so touchy. You know you’re beyond that now.”


“Oh, you’re being such a bitch! Are you on the rag?” she half-whispered to him, and they both laughed out loud.


As she looked up towards the store above, she stopped in her tracks and, to Pat’s surprise, took hold of his hand and squeezed it tightly. Without turning around, she said in panic “That’s him – and his wife! And that must be their son! Don’t look, they’re coming down. Oh no! What do I do?”


Without hesitating, Pat pulled her gently onto the escalator. Now he too looked up and saw a dignified older man with grey hair carrying a yellow plastic shopping bag. He was in a dark, well-cut jacket and looked like he’d just stepped off his yacht to do some Christmas shopping with the family. Next to him was a lithe woman in a cashmere-and-silk outfit, wearing thick sunglasses and a complicated hairdo, and behind them a teenage boy whose hand was loosely slung over the man’s shoulder. As they came closer, to his utter astonishment, Pat recognized the man’s face. “It’s destiny,” He thought to himself, remembering the fortune teller’s prediction. Nikita had never divulged her patron’s real name, John Dorff. She always referred to him as Honey, stressing the second symbol so that it sounded vaguely Texan. When she first told Pat Nair about the man who had picked her up in the Rosewood Room two years earlier and who then, one day, out of the blue, proposed that she should be his mistress, he was dumbfounded but supportive. She had added that, like most venture capitalists, he was fit for his sixty-four years, and that he was loaded. This last detail was the most important one. John Dorff had been very successful and had a track-record of building and selling companies for over a billion dollars. Why else would Nikita Malin be wasting her youth on a married man nearly four times her age who had no intention of committing himself? As the family passed Nikita and Pat on their way down to the second floor, the man looked over in their direction. The woman was turning the other way while the boy’s attention was drawn to a colorful film poster that was hanging off the balcony. Nikita Malin did not return the gaze. Instead she put on a hard, artificial expression of indifference and fixed her attention on the space in front of her. In doing so, she was unaware that it was not at her that John Dorff was directing his gaze, but her companion, for as they passed each other with only the two feet between them, he too recognized Pat Nair and involuntarily his face lit up with an expression of remembered pleasure. 


They were in a Japanese restaurant at the basement level. Pat Nair swallowed his mouthful of sushi and said nothing. His features registered a moment of sadness, enhanced by the pungency of the wasabi. He had been explaining to Nikita, who sat in attentive silence, how he had met “Honey” two years before she did, what had gone on between them and how they had parted company. 


“He went to India, on business, and the club was closed down overnight while he was away. That’s why we lost touch, and after that I never saw him again,” he said, continuing his tale and addressing these words to his own reflection in the window. If Nikita Malin was surprised by what she heard, she managed not to show it. She had long suspected Honey of being bisexual, but had not expected her intuition to be confirmed by such a personal connection. And now Pat Nair was trying to paint a professional encounter into some kind of grand love affair. She kept her composure but her mind was swirling, especially when he had the nerve to try to convince her to share Honey with him. 


“Come on, he’s loaded! He’s got enough for both of us!” he pleaded. 


Nikita Malin took this as the cue to comment. She chose her words with care and put on a show of well-tempered indignation. She told Pat that the supposed romance between him and James Dorff had taken place at a gay brothel, albeit a high-class one. And how dare he try to muscle in on her good fortune when she had done all the running? But even as she was discouraging him for making a play on her Honey, Nikita was well aware that Pat was already planning his moves. James Dorff, one of the most famous VCs in Silicon Valley, was a prime catch for any ambitious hustler. Nikita herself hadn’t believed her luck when he installed her in a condo overlooking the bay. He had first met her up at the Rosewood,  an exclusive bar and restaurant where she was one of the part-timers working for  cash and jewelry. You had to be both beautiful and discrete because the clientele consisted of the the Valley’s rich and powerful. James Dorff had chosen her out of a roomful of women who looked like starlets, and after their first sexual encounter in the VIP suite he had seemed quite pleased with her. After three visits he asked her out to dinner, which was quite normal (and encouraged by management since it reinforced the illusion that the girls were not professionals but companions). That night, by the candlelight of Coi in San Francisco’s antique district, James Dorff explained that he was starting his own VC firm, reminding her that ten years earlier, when Nikita was still a young girl, he had sold his first company for a billion. But he had been betrayed, he was quick to add. Losing out to the two senior VC firms also in the deal, he had walked away with less than ten per cent. (To most people, a hundred million dollars was nothing to sniff at, but to the VCs, it was all about winning). Now he was ready to return to the fray. However, because he’d be raising money, he could no longer risk being seen anywhere that could cause a scandal. He had decided not to frequent places like The Rosewood any longer, but he wanted to continue seeing her, and that was when he asked her outright to become his mistress. Without letting her have time to think about his proposition – as though, in the style of men used to having their way, he was sure that she would not resist – he went on to give her the details of the arrangement that he had worked out and which she would have been foolish to have refused.


Nikita had been overwhelmed by the offer. It meant the end of having to make the effort of going to work and worrying about paying off debts she had accumulated, and living in cramped accommodation in the Mission with her would-be entrepreneur room-mates. It would even giver her time to go back and finish her university degree, if she chose to do so. And if she played her cards well, she could even set up her own business. Suddenly the future was wide open. Everything was possible, and all she had to do was give pleasure to a man whose vanity, with the help of Viagra, was soothed by possessing her firm, trim body. So without thinking of the consequences, she accepted.


At first, she had been drunk with her new life. Moving out of the small rented apartment into an exclusive condo with a view of the Bay was like arriving in the realm of the angels. James Dorff visited her two or three times a week, often bringing a bottle of champagne and a little gift. They never went out again, after that evening at Quince, but delicious, elaborate meals were ordered from the finest establishments in San Francisco. In those early days, once he had finished talking about his business deals, he would ask her how she was spending her time and whether she was happy. But as the months rolled slowly by, he became less and less interested in what she did or thought. He would arrive and take his pill and wait for the effect to kick-in and then fuck her as though he was offloading all of his pent-up aggression. Afterwords, while she massaged his back, he would ramble on about the back-stabbing VC world or his convoluted family life. He would tell her how difficult his relationship with his wife was, and that she hated him. Once Nikita made the mistake of giving him her opinion about his dysfunctional marriage, but the way that he cut her short made her realize that he sought neither her response nor her sympathy. He merely needed her as a beautiful trinket to bolster his self-esteem and as a receptacle into which he could pour his artificially stimulated desire.


Now, two years later, she was desperate with the sheer boredom of her existence. Dorff’s visits were less frequent, and when he dropped by, she found it harder and harder to be patient. The routine of being somebody’s mistress did not suit her. Being a sex object made her feel like an idiot. Even her cocooned comfort did not compensate for the sense of despair that overcame her. There were days when she desperately wanted to pack up and leave. But then she could never forget the money and the perks that came with her status. She had become used to the luxury, and she knew all too well that to regain her freedom, she had to be prepared to give up a lifestyle that most of the Bay Area only dreamt of. For them it would remain a distant dream. But for her it was what she awoke to every morning. While Pat was waxing lyrical about his affair with Dorff, he had spared no details, as it to prove that he, as a man, could do a better job of satisfying Dorff’s desires than she, a woman could. While she listened to his lurid descriptions of Dorff’s peccadilloes, Nikita Malin’s mind was busy weighing up her options. She knew that her efforts at dissuasion would only challenge him to go ahead and run after her man as son as the opportunity arose.  A voice in the back of her mind was telling her how easy it was to say: “Okay, have him. He’s yours if you think you can catch him.” And she would be free. It was what she wanted, after all. But another voice was already suggesting ways to achieve the same goal without losing the benefits she had come to feel she deserved. 


That evening Dorff visited her. They greeted each other coldly. Neither mentioned the encounter on the escalator at the shopping mall. He declared immediately that he was not in the mood for sex. He told her to open the champagne, and then, after taking a big gulp from the glass that she handed him, said casually: “And who was that boy you were with this morning?”


Nikita had expected the question. “Oh, that was an old friend of mine from university,” she answered. 


“Are you going out together?”


Nikita smiled broadly before replying: “No, he’s gay. Couldn’t you tell, honey?”


James Dorff nodded his head without changing his expression and took another big sip of his champagne. Nikita Malin felt that it was the moment to take the gamble. 


“Would you like to meet him, honey? He’s very interesting. He used to study economics, you know. He’s quite brilliant. He told me that he recognizes you straightaway because he spent a summer working at a VC fund. He says you’ll raise the money for your new fund for sure, especially with that line you’re pushing about data being the new oil.”


Dorff took a few seconds to scrutinize Nikita’s face for any sign that she was being less than ingenuous. Satisfied, he nodded again.


“Why not? Yes, I’ll meet your friend. If he’s as clever as you say, I might be able to hire him for my research team.”


Nikita Malin smiled inwardly. She sensed her first step to freedom. 


During the days that followed Nikita was in a strange mood. The fact that her plan involved betraying both her friend and her benefactor filled her with conflicting emotions. It was not exactly that she felt guilty for what she was doing, but there was a certain unpleasantness she could not easily shake off. Pat Nair had always been patient, supportive and generous to her. As for Dorff, he had given her a few years of affluence that she had not expected to come her way. The only real complaint against him was that he had treated her as a body and nothing else, but then all the men she had met, with the exception of Pat Nair, had done that. To counter her uncomfortably acute sense of disloyalty, Nikita kept reminding herself what her mother had taught her when she was a little girl: that you are totally on your own in this world, and you have to look after your own interests. And in the end her mind yielded up the justifications she needed to go ahead with her scheme. After that, it was merely a matter of finding the nerve to carry it through.


With her newly found sense of purpose, Nikita Malin now took the decisive step towards her freedom. She called Pat Nair and asked him casually if he’d had any luck contacting Dorff. Pat, thinking Nikita was provoking him, answered coldly: “I’m in no rush. I’m not that desperate, whatever you think. I’ll get to him when I want.”


“Well then, come for dinner,” she said. “He’s interested in seeing you.”


There was silence on the other end. Nikita could sense Pat Nair’s excitement. She knew him too well. 


“What’s your game?” he asked, finally.


“I’ve been thinking, I don’t want us to be rivals. And I knew you’d find some way of meeting him. So why can’t we be cool about it?”


Satisfied that there hadn’t as yet been any communication between Pat and Dorff, Nikita sent Dorff a text on his mobile. It was a rule that she never called him directly given his position. His paranoia had affected her to such an extent that she often imagined someone listening in to her own phone and was constantly noting little odd sounds which she could not account for. But that day, as part of her plan, she sent him a blatantly lascivious text message telling him how she was lonely and needed to see him urgently. She made it sound like she was a bitch in heat. He came around that afternoon and made no mention of her transgression. As he was through the door he was ripping off his jacket and began climbing on top of her. Shortly after, passion over, he said that he had a meeting to attend and could not stay. He showered quickly and began to put his clothes back on. 


“ I’m so angry!” she blurted out, as she lay exhausted and naked on the bed. 


“You and Pat were lovers once, weren’t you? He told me, so don’t deny it!” Her voice was more hurt than angry. John Dorff stopped what he was doing, looked at her for a while in surprise and then burst out laughing.


“So, he told you.”


“And you’re still hot for him! I know you are.”


He made no reply to this last remark.


“I want out! I can’t stand it. It’s awful.”


“Come one, calm down. Don’t be so jealous,” he said. Suddenly his face looked weary and dark.


“No! I mean it,” Nikita continued. “You don’t really care for me, and now I know that you prefer men. So let me go! I’l fix you up with him. He can take over this apartment if you like. Just give me something for the years you’ve had from me, and I’ll be out of your life.” 


Nikita was sobbing, and as she did so, she remembered Dorff’s advice to her at their very first dinner, when he was setting out the ‘terms’ of their contract: “I don’t want any emotions in this. If you’re going to get jealous and cry because I don’t love you and that kind of stuff, then don’t even think of being with me because I don’t have time for any of it.” He had said it bluntly enough. 


Now, even without looking up at him, she could feel his annoyance. With every second her sobs became more intense. She buried her head in the pillow and gripped it with both hands. 


“Oh stop it! I told you I can’t stand this kind of thing. And by the way, I told you never to get in touch with me by phone unless it’s an absolute emergency. You’re getting to be a real pain in the neck!”


“Then let me go! I’ll leave you in peace. I’ll let you have Pat. But I can’t share you with anyone else. It killed me to see you with your wife at the shopping mall the other day. I can’t live with jealousy. I just can’t. I’ll do something to myself that you’ll regret if you carry on treating me like this.”


Eventually, she calmed down, but not before Dorff agreed to let her have her freedom along with an interesting sum that would last her for a couple of years – a pittance for him, a golden handshake for her. In gratitude she told him that she would arrange a farewell dinner, so that he could be properly reintroduced to Pat Nair. It would serve as a kind of handing-over ceremony. John Dorff, relieved that he was getting a jealous girl off his hands and at the same time overjoyed that he was rediscovering a treasure he thought he had lost for good, accepted Nikita Malin’s offer without hesitation. A date was fixed. 


If Nikita Malin had been content with what she had achieved so far she might had had the freedom she desired when John Dorff made the transfer to her account of the sum he had promised. But things had gone so well up till then that she was encouraged to carry her plan through to the final stage. In fact she could not stop the momentum of her actions. For the first time in years she felt alive. It came down to the fact that she wanted much more than she had been offered, and she was sure it was within her reach. 



(Please email me for the complete story: sunilm1@yahoo.com)



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