The Billionaire From Portland

by Simply BWWM

  “Thank you,” Jessica said, smiling slightly. “I figured it would be a bit more official than going and getting pho somewhere.” Bradley chuckled.

  “Well, I want you to enjoy your meal,” he said. He was already impressed with her work: she’d gotten more done than he had thought possible between when he’d briefed her that morning and when she’d come into his office to give her progress report just before their lunch together. “That means that if you want to order a drink, I’m not going to think you’re some lush.” He gave her another smile and saw color rise into Jessica’s cheeks for just an instant.

  “Oh, in that case…” Jessica said, reaching for the drink menu they’d been given playfully. Bradley snickered and looked over the lunch menu idly. He knew what he would get, but he was--strangely--interested to find out what Jessica’s selections would be. A normal level of interest in a new employee, especially one who works so closely with you, is fine, he told himself defensively. Just because his new assistant was beautiful didn’t mean that he had any bad intentions towards her; after all, he’d had lunch once or twice a week with all of his assistants.

  The waitress came to the table and asked if they’d like to start with drinks. “I will have a glass of water and…” Bradley considered. “The specialty old fashioned you make here.”

  “And for you, ma’am?” Jessica looked up from the two menus in her hands.

  “I think I’ll have a water as well, and your Eastside Elderflower,” she said, setting that menu down.

  “Do you know what you’d like to have for lunch, as well? Or should I come back?”

  “I know what I want,” Bradley said. “But that’s mostly because I only get one of two or three things here. Jessica--are you ready?” The woman glanced over the menu one more time.

  “I’ll be ready by the time you order,” she said brightly. Bradley grinned to himself. She wants to gauge how much I’m spending and then choose based on that, he thought.

  “I’ll have the pan seared rainbow trout, then,” he told the waitress, handing her his menu.

  “I would love the crab and shrimp BLT,” Jessica said, also handing her menu back.

  “I’ll have both right up for you,” the woman said, smiling at them both. Bradley watched the waitress leave, and considered how to move forward in the lunch. It was oddly awkward, the way he felt; he needed to maintain his objectivity as much as possible. “How are you enjoying Portland? It’s got to be really different from Atlanta,” he said.

  “It’s very, very different,” Jessica agreed. “I’m trying to mentally prepare for when it gets cold--and also when it eventually snows.” Bradley smiled.

  “Well, fortunately the heating system in the building is really good,” he told her. “And I think there’s a plan somewhere along the lines to incorporate some kind of heating in the parking structure, so that should help as well.”

  “I am going to be ploughing my paycheck into heavy coats and gloves,” Jessica said. She shook her head, smiling slightly.

  “It’s a big move, coming to the other end of the country,” Bradley observed. “Totally different climate, all that--do you know anyone in Portland?” Jessica shook her head.

  “I know you--by name, at least--and I know your former assistant, but I think he’s already headed out of town, isn’t he?” Bradley nodded. “I know one of the checkout girls at Fred Meyer. Maybe.” Jessica shrugged. “Apart from that, I don’t really know anyone.”

  “That must be a bit intimidating,” Bradley said. “What made you decide to apply for the job?” Jessica licked her lips, and for just an instant--before it was ruthlessly suppressed--Bradley felt a jolt of heat course through his body at the sight of it.

  “I wanted a total change of life,” Jessica said. “I’d applied for a few other positions as well--sorry if that dings your ego.” Bradley laughed.

  “No, I would have assumed that you were looking at multiple possibilities at the same time,” he said. “It’s only smart to do that. But obviously, you weren’t working somewhere else when you applied to come to Portland.” Something flicked across Jessica’s face, too fast for Bradley to catch it.

  “I took a leave of absence from my last job,” Jessica said slowly. “I needed to take some time to figure out some things, and once I felt like I’d gotten to that point...I decided that I wasn’t happy in Atlanta anymore, and that I should go somewhere else--get a bit of the world under my feet.” Bradley considered that answer and nodded.

  “I was born in New York,” he said. “Not the city--out in the middle of nowhere. I went to college out at UCLA, and then transferred to Stanford, and ended up dropping out just short of my degree.” Bradley smiled wryly. “My parents were not really pleased by that.”

  “I am not surprised at all,” Jessica said.

  Bradley chuckled. “I’d been tinkering with some projects while I was in school, and one of them had gotten the attention of a major company, so I dropped out one semester short of finishing, and things just sort of took off from there,” he went on. “And then of course, I eventually came up here, where the tech industry’s more or less moved itself for the moment.

  All that to say: I get needing to move around, to be somewhere else for a while.” The waitress arrived with their drinks, and Bradley raised his glass to Jessica, who did the same. He took a sip of his old fashioned, and it was just as good as it had ever been.

  “So, I guess it’s my turn to ask a question, to keep things going,” Jessica said. Bradley stifled a laugh at her frank comment. “It must be...I mean, I guess you must have had fairly comfortable parents, to have gone to UCLA and Stanford. But surely, your parents weren’t billionaires; so, it must be quite a thrill to end up there yourself.” Bradley nodded.

  “It’s a thrill, but also a burden--and yes, I know exactly how that sounds,” he said, shaking his head in slight chagrin. “When you get to be that wealthy--prepare for a rich douche whine--it’s hard to know who you can believe. Who’s telling you the truth and who just wants to get on your good side. It’s even harder to date; mostly because a lot of the women I’d like to get to know better don’t want to feel like they’re being courted as a trophy girlfriend, and a lot of the women who want to get to know me better very much want to be a trophy girlfriend.” Jessica nodded and sipped her water.

  “I can see that,” she said. “You have to be careful who you trust.”

  “Absolutely,” he said. He wagged a finger at her. “And now that you’ve got access to all the inner workings of my life, I’d better be able to trust you.” Jessica smiled brightly.

  “You can absolutely trust me,” she said. “I would have hoped that my previous bosses would have given you a good impression on that point.” Bradley nodded.

  “They did,” he admitted. “They said that you were always discreet.” Again, a little flicker of something, too fast for Bradley to be able to see what it had been, darted across Jessica’s face when he mentioned her discretion. “Everyone you’ve worked with--at least those on your resume--thinks the world of you.”

  “I’m glad to hear it,” Jessica said.

  Their food arrived, and Bradley changed pace somewhat, asking Jessica about her interests outside of work, about what she had thought about seeing in Portland. “It’s a really great city for just about anything you like to do,” he said. “If you’re into outdoors stuff, there’s hiking and skiing and boating. If you like to stay inside, there’s concerts and bars and museums of all kinds.”

  “You don’t have to sell the city to me, I’m already here,” Jessica joked. “I haven’t really decided what direction I’m going to go in just yet...but I’m definitely checking out all my options.”

  “It’s a shame that you don’t have friends here who can take you around to different places,” Bradley said. “Although, of course, there are a ton of apps to connect with people--one of them is in my portfolio.” He chuckled. “Not that I’m trying to sell you on that, of course.”

  �
�I think the one in your portfolio is a matchmaking app, isn’t it?” Bradley nodded. Jessica licked her lips again and set her sandwich down for a sip of her drink. Bradley had already noticed that she ate like a consummate lady--neatly, with graceful movements. “I decided to kind of put the brakes on any kind of dating, at least for a while,” she told him.

  “That’s an interesting decision,” Bradley said. Don’t push her on it. She’s your employee--that would be sexual harassment. Or it could be. But no matter what it is, it’s not appropriate.

  “I want to take my time and get to know people generally for a while,” Jessica said, her voice neutral. “I think--as hipster-like as this sounds--that I just need to approach things more mindfully for a while.”

  “That does sound like something a hipster would say,” Bradley said, a teasing note in his voice. “But that doesn’t mean it’s wrong.”

  “As contrary as it sounds, now that I’m here, I don’t want to rush into anything else,” Jessica explained. “I want to sort of figure out where I am, what I’m doing--all that--and then see about where I can fit other things, like a social life, in.” Bradley laughed.

  “I’m not making fun of you,” he said quickly. “It’s just that you sound kind of like me--or at least, me when I came to Portland at first. I wanted to focus just on my work.”

  “That’s where I’m at right now,” Jessica agreed.

  “Be careful with that,” Bradley said, looking at her more seriously. “My mistake was that I’ve focused so much on my work that I never really got the hang of social life--not really, anyway.” He picked up his fork once more and started in on the spinach salad that had come with his fish. “I mean—obviously, I network with people, I have ‘friends’ in the industry, fellow billionaires and millionaires. But it’s not the same; at least, I don’t think so.”

  “I feel like loneliness is probably the cost of being so successful,” Jessica said. “There aren’t very many people in the world who have the same experiences you do--and there’s no telling if you’d even get along with those that do.” Bradley smiled slowly.

  “Exactly that,” he said. “You are a very insightful woman.”

  “Thank you,” Jessica said, color coming up into her cheeks once more. Bradley wasn’t naive; he knew when a woman was interested in him. He took a quick breath as surreptitiously as he could. Get back into neutral territory, he told himself. Just because there was clearly some tingle of attraction from both of their ends, it didn’t mean anything inappropriate had to happen; it didn’t mean that he could give into the impulse to flirt. He was the boss--he had to be the one to take the high road, to be more circumspect.

  “Of course, you’re going to be really busy managing my life,” Bradley said. “So, it’s just as well that you’re putting social life on the backburner for a while.”

  “That was about what I figured,” Jessica said, the color in her cheeks returning to normal. “I’m perfectly happy with that for now.”

  Bradley focused his thoughts on the most neutral, platonic topics possible, and pushed any thought of Jessica having an attraction towards him out of his mind altogether. She was competent, obviously intelligent, and just as clearly a good worker: he would focus on her professional attributes and keep things where they should be between them.

  Chapter5

  After two weeks of working for Bradley Holt, Jessica was certain she could do the actual tasks demanded of her, but she wasn’t sure she could do the actual job. She’d managed to learn everything she needed to learn about managing Holt’s affairs and daily obligations within a couple of days of working with him, but in spite of the fact that his changing daily schedule--and piles of commitments--kept her busy all day long, she found her mind wandering. So much of what she had to do was comprised of things she didn’t have to really think about.

  That was the trouble: if she didn’t have something occupying her mind constantly, the cravings would hit. And the cravings that had started out manageable, over two weeks, became harder and harder to ignore. She’d gone to a couple of meetings after work--the women’s only meeting at a church on 45th Avenue, just off of Hancock Street--and she’d listened to the other women talking about triggers, and about staying “sober” as it affected them.

  Sex Addicts Anonymous didn’t preach complete abstinence, but Jessica had gone through the exercise of creating her “three circles,” yet again: the inner circle with the behaviors she knew were fueled by her addiction, the middle circle with the thoughts and things she did that might lead to her acting out, and the outer circle with its list of healthy sexual behaviors that would help her maintain her recovery.

  But it was getting more and more difficult, and Jessica wasn’t sure what she could do. At least twice a day, sitting at her desk, knowing that Holt was in the next room, she’d get the tension deep down between her hips; not just arousal, but like a kind of hunger that came from below her stomach, gnawing its way through her body. Images--not detailed enough to be fantasies, precisely--flitted through her head: sucking Holt’s cock, having him bend her over his desk and fuck her senseless.

  Then, when she would try and push those images out to focus on something else, her mind would wander down the alley of old habits: when she hadn’t been able to get the guy she wanted in the past, Jessica had gotten the urge to have sex with anyone, almost spitefully, as if to show the person who had either rejected her or who hadn’t proactively shown interest in her, or who hadn’t propositioned her, that she didn’t even want them anyway, that she could get laid by whoever she picked out of a lineup if she wanted to.

  So instead of the fantasies of Holt, Jessica’s mind--stressed out--had darted down that dark metaphorical alley, and she’d found herself tarrying in the mail room a few floors down, or spending a little longer at the dry cleaner’s, thinking about how she could convince the weathered-looking man running things back behind the counter to meet her back behind the building and let her go down on him. Stop. Stop. She had managed to avoid actually acting on any of the impulses, but found herself in her car, soaked through her panties, squirming a bit from how much she wanted gratification.

  She hadn’t been sure whether to consider masturbation a “middle circle” or an “outer circle” behavior and had held off in her SAA work on even addressing it. Even in her counseling, when she’d been in residence, the counselors had been vague about masturbation. “There’s healthy masturbation, and there’s addict-masturbation,” they’d said. And Jessica could see where they were coming from; just the act of getting one’s self off wasn’t harmful or else the majority of teenagers would be addicts.

  It was like everything else in the strange addiction she’d fallen prey to: contextual. No one was allowed to masturbate during the month they were in intensive in-patient treatment, and it was “frowned upon” for them to masturbate in the intensive outpatient program; that could, the rehab counselors pointed out, become nothing more than a new trigger, nothing more than a new addiction--replacing old bad habits with new bad habits.

  Jessica sat at her desk, finishing up one of the memos that Holt had assigned her. She glanced at the clock on the lower-right corner of her screen. She was supposed to meet with him in forty-five minutes to go over the memo. She nearly had it done. You could just go into the bathroom and take care of the physical aspect of it, so you can be clear-headed in the meeting itself, she thought.

  There was no reason for Holt to know or care how often she went to the bathroom as long as her work got done, and as long as no one was left hanging out in the atrium in front of his office. There wouldn’t be anyone coming in for at least two and a half hours, after her meeting ended with Holt; she could duck in, get herself off, and revise the memo before she had to go into her boss’ office easily.

  Jessica bit her bottom lip until sharp pain cut through her thoughts. Was she entertaining this idea for the right reasons? Or was it just an excuse to indulge her addictive tendency? She took a slow, deep breath, resisting
even the urge to squirm and wiggle her hips in her seat--every time she did, her slick labia rubbed against each other, putting just a little bit of friction up against her clit.

  Her gaze moved around the desk, and out of habit, her brain catalogued the things she could safely insert in her dripping pussy: a thick marker, the handle of her brush that stuck up just a bit from the top of her purse in the bin at her feet. She could put her phone on vibrate and use it; she could, of course, just go into the bathroom, pull up her skirt and rub herself through her panties--or underneath them.

  Are you thinking about this for the right reasons? Just the thought of going into the bathroom and getting herself off was making Jessica almost unbearably aroused, and with that arousal came a trickle of not-quite-fantasies, of all the things she could do if only: going down to report a “janitorial” issue and convincing one of the maintenance staff to take a “gratuity” from her body, or going into the copy room downstairs and, after making sure no one would come in, rubbing herself against the blunt edge of the copier while it made endless copies of some irrelevant page, buzzing all the while.

  Whatever the case, you need to take care of this or you’re going to do something you really regret--like propositioning your boss. You can’t afford to lose this job. Jessica took a slow, deep breath and glanced at the memo she’d been working on. It had all of two sentences left to complete it, and she had another thirty minutes before Holt expected her to let herself into his office; she could get herself off in fifteen, finish the memo, and go into her meeting with him satisfied enough to think clearly.

  Jessica glanced around, already feeling naughty and just faintly dirty, even. An office bathroom--even one as clean as the one on her floor, only used by her, was hardly a great place to masturbate from a purely hygienic standpoint, but the thought of the forbidden pleasure sent a tingle through her. She stood and stretched, feeling the dampness of her panties against her vulva, and locked down her computer, flipping up the sign that said she would be back shortly, just in case--it was good to maintain good professional habits.