The Billionaire From Portland: A Sexy BWWM Billionaire Romance (United States Of Billionaires Book 10)

by Simply BWWM

  He let her speed up again after a few agonizing seconds, just when she lost that closeness to climax, and slowed her down once more when she was on the edge. Over and over again, until Jessica couldn’t stand it anymore. She groaned in frustration as Bradley began to stroke and rub her, bringing her so close that she could almost taste the orgasm gathering in her hips and then stopping almost completely. “Ask me to let you come, Jessica,” Bradley told her.

  “Please, Sir,” Jessica said.

  “You have to do better than that,” Bradley said. Jessica met his gaze. She wanted it so badly--why was he denying her when he knew she wanted it? When he could feel it, she knew he could?

  “Please, Sir,” Jessica begged.

  “No--you have to ask specifically for what you want,” Bradley told her. He kissed her. “Tell me what you want, Jessica.”

  “Please let me come, Sir,” Jessica said, almost crying it out.

  “Again,” Bradley said firmly.

  “Please, please let me come, Sir,” Jessica repeated. Bradley smiled and began thrusting up into her, touching her, rubbing her clit until she was right on the edge, so close that she could taste it.

  “You can come, Jess,” Bradley murmured in her ear, pounding up into her as he rubbed her clit steadily. Jessica felt the tension deep down in her hips break like a faulty dam, and she cried out in pleasure as wave after wave of sensation coursed through her. It was the most intense orgasm of her life, aided by her sense of helplessness, her bone-deep obedience to Bradley’s commands.

  She fell into it like a deep pool, letting it rampage through her, letting it obliterate all of her thoughts as she continued to ride him, her body tensing and relaxing in spasms she couldn’t have controlled if she wanted to. Jessica collapsed against Bradley when the pleasure became too intense, and didn’t even notice him slow to a stop, without reaching his own climax inside of her, just holding her.

  She was so far gone she didn’t even feel his fingers tugging at the bindings on her wrists, freeing her finally. As Jessica slipped into the deep velvet darkness of intense pleasure, she vaguely realized she’d never felt that good in her whole life.

  Chapter14

  Bradley stepped into the building where his office sat, smiling slightly to himself in anticipation of what the rest of the day held for him. He’d had to leave just before lunch to meet with some business partners, but he would have the rest of the afternoon more or less free--apart from specific tasks that needed to be done--so he would be able to enjoy himself with Jessica at least part of that time.

  It had been almost a month since they’d started their new arrangement, three weeks since their first “session” in Jessica’s living room, and so far, it seemed to Bradley to be satisfying what she thought she needed from her partners. She had been as focused as ever, had not seemed as flustered or irritable, and she had--under his instruction--forwarded all of the messages her ex sent her to him. Bradley knew it made her uncomfortable to do that; it was easy, seeing some of the pictures, reading some of the messages, to understand why.

  He had been working with some of the people he knew in certain circles to try and find out how to get Drake fully out of Jessica’s life. While the BDSM sessions kept her from “falling off the wagon,” so to speak, and while he enjoyed them more even than he had their original trysts, he didn’t like that someone could still make Jessica feel vulnerable, manipulated, shamed. She didn’t deserve to have the constant harassment interrupting her day.

  She didn’t deserve some manipulative bastard trying to make her fall back into active addiction to serve his interests in degrading and humiliating her. “You’re a filthy little cum-slut who needs a good railing. Come over.” The things Drake messaged Jessica with--the things he called her, the pictures he had of her, or the “inspiration” he thought would trigger her, disgusted Brad.

  It wasn’t the words or the images themselves; he knew better than many that there were normal people who got off on humiliation, and it was fine for that to be their thing. It was the fact that he could sense, even without knowing Drake, that it was meant to be abusive. It was meant to make Jessica feel like she deserved whatever bad treatment she was given.

  So, he had focused on the sessions with her, on building up her self-respect, her sense of being a valuable, worthy person, as much as he could. As Bradley stepped onto the elevator leading up to the executive suite he occupied, he smiled more deeply to himself, remembering the last “punishment” session.

  He’d known that Jessica had “misbehaved”--broken the sexual “rules” they’d agreed to--on purpose. Drake had been particularly aggressive with the messages he’d sent her earlier in that day, and she’d wanted for Bradley to actually humiliate her, to degrade her and make her feel like filth. So, she’d gotten herself off without permission, knowing he would find out.

  He had spanked her, but he had made her make the decision of when she was sufficiently punished, and he had told her that if she lied, if she tried to make him punish her more severely than she truly believed she deserved, the session would end with no gratification.

  She would go back to her desk, and she would spend the rest of the day not being allowed to get herself off. Of course, Brad knew that Jessica--after so long being abused and degraded by people who wanted to use her as a piece of meat--could endure a very harsh punishment indeed. But he’d watched her carefully. He had, after a few weeks, learned when she was reaching the edge of what she could tolerate, what she could actually enjoy.

  She had endured his hand, the paddle, and then the riding crop he’d bought a few days before to change things up--to her breasts instead of to her buttocks--before telling him that she had learned her lesson--and Brad had known that she had stopped him short of what she could actually endure.

  It was, he thought, better than her trying to use him to degrade herself. He’d rewarded her with a few more blows--with his hand--to, he said, “hammer the point home” before kissing her, holding her, soothing the reddened areas on her buttocks and breasts and allowing her to show him how grateful she was for his punishment, his correction.

  He had finished in her mouth like she wanted, and then had gone on to get her off with his mouth and fingers and the vibrator she kept in her desk. “You are not allowed to use this toy on yourself for three days,” he’d told her, holding it in front of her face. “It will stay here in my office so you aren’t tempted. Only I can use it on you, until I trust you to obey the rules.”

  It had also been thrilling, in its own right, to take up his new role; Brad couldn’t deny that to himself. As soon as he’d mentioned to his friend and sometime lawyer, Helena, that he was “seeing” a woman who he thought might be interested in exploring submission, she’d happily taken up the challenge of teaching him how to dominate: how to do it safely, how to take control, and--at his request--how to do it without debasing the woman he cared about.

  “I’m assuming you’ll want to avoid epithets like ‘slut’, ‘whore’, and all that,” she’d said. Brad had confirmed her guess. “The role you’d want to take then would be an authority figure dealing with a recalcitrant underling. Headmaster and student, teacher and student--if she’s into that dynamic--something like that where you create a list of arbitrary rules that she has to follow. Then, you mete out punishment based on infractions. Add to the list, change rules, give her things to do--to herself, to you, and so on--and go from there. You can use a more generic ‘good girl’ ‘bad girl’ thing, instead of degrading her personally.”

  He’d watched her with some of her submissives, taking in the way that she took the time to comfort them and soothe them after intense sessions, watching how she read how her partner was reacting. It was easy with Jess, having already learned her reactions, having already gotten to know her, when things were getting too intense for her, when she was edging towards more than she actually wanted to tolerate.

  He knew when she was trying to manipulate him into actually harming her, actually
pushing her limits and overstepping her boundaries--and he checked himself, knowing that she was still, even after weeks, in the mindset where she couldn’t entirely trust herself.

  As he stepped out of the elevator, Bradley looked for Jessica, seated at her desk in front of his office door. She was right there, her cheeks flushed--and he grinned, remembering what instruction he’d given her before he left. It was, as Helena had described it to him, a “self-control lesson,” where he’d given her permission to bring herself to the edge of orgasm as many times as she wanted while she was away, but she was not permitted to get herself off.

  He’d given her a toy he’d bought the day before--a completely silent vibrator that clipped to the inside of her panties, with a remote control that looked as nondescript as anything else that might be on her desk--and he’d told her that he trusted her not to get herself off without permission. Brad knew that she wouldn’t overstep--not this time.

  “How’s the morning going, Jess?” He paused at her desk and looked down at her, amused and already desirous of rewarding her good behavior.

  “Been very busy,” Jessica replied, giving him a slightly strained smile. “I’m hoping we’ll have a chance to meet and go over the morning’s work.”

  “Order lunch into the office,” Brad told her, letting some of his dominant tone creep into his voice. “We’ll go over everything then. Choose what you want.” Jessica nodded.

  “Yes, Sir,” she said quietly, the flush in her cheeks deepening. Brad looked at her desk and spotted the remote he’d given her. It had a range that would let it control the vibrator from the opposite ends of a house--he could definitely manipulate it from within his office. He picked it up and pressed the button to turn up the vibrations. Jessica half-gasped, her eyes widening for an instant.

  “I’ll just hold onto this,” he told her, meeting her gaze. “Remember the rules, Jess.”

  “Yes, Sir,” Jessica said, her voice cracking slightly. Brad smiled.

  “If you’re good, you can keep it on during lunch,” he told her in a whisper. “And we’ll see how many times you can...finish...in an hour.”

  “Thank you, Sir,” Jessica murmured. “I’ll be very, very good.” Brad continued on towards his office door and played with the controls on the remote, bringing the vibrations up to a fever pitch and then cutting them off in rapid succession as he triggered the locking mechanism and opened the door. He brought the vibrations back up to a level that would keep Jessica stimulated but which wouldn’t bring her to the edge and glanced over his shoulder.

  “I do expect you to have plenty of work to show me, Jessica,” he said before stepping into his office.

  Brad thought about what they’d agreed to in the contract--what Jessica had listed as being hard limits, things she never wanted to do, things she maybe wanted to do, and things she definitely wanted to do. The things she definitely didn’t want to do, he had never intended on doing with her in the first place.

  Some of the things she had marked as “maybe” he hadn’t really considered, but now that their relationship as dominant and submissive had deepened, he was starting to feel curious about them on his own.

  Bradley sat at his desk, turning up the vibrator just a tiny bit, and considered. He knew that Jessica’s experiences with anal play had all been with people who had used it to debase her; she had marked everything in that category as a “maybe,” and Bradley wanted to test her a bit, to make her put up boundaries, without giving her the chance to force him to violate her boundaries.

  He wanted to give her an experience of anal--something he’d only done with one or two women in his sexual career so far--that wasn’t intentionally degrading, that was for her pleasure.

  He began to think about how he could go about doing that, and took his phone out to do a little private research on the subject. It would be good, he thought, to feel her trembling in relief and to hear her pleasure--and it would be good, too, to watch her take control of the situation within the context of the dynamic they’d set up. He texted Helena a brief sketch of what he wanted and waited for her response.

  While he waited, he checked his email. The new hire he’d approved of in the IT department was--it seemed--performing well, but the man was behaving a little strangely. There had been an HR complaint, but it was, on the surface, nothing that a little retraining wouldn’t solve. Bradley replied that he wanted updates on the situation.

  Make sure to forward me his retraining notes and whatever else is going on with him, he wrote back to the manager. We want to make sure that we aren’t fostering an environment where any kind of sexual harassment is acceptable.

  He thought of the irony of that, considering the fact that--technically--what he was doing with Jessica could, in theory, be considered harassment. He did, after all, have sex with her on the clock, among other things. But he hadn’t made it a condition of her employment, and he had made it clear that he would still keep her as an employee if she decided not to have sex with him ever again.

  Bradley delved into his work, setting an alarm for every fifteen minutes so that he could play with the remote to Jessica’s vibrator at random between then and the time that she would be in his office again.

  By the time she came in, he was determined to make sure she was utterly on edge, her knees weak with the need to get off, and he wouldn’t be punishing her at all, that session. It would be all reward. Bradley grinned to himself, reflecting that there was something immensely gratifying about being able to reward someone for helping themselves to heal.

  *

  Jessica could feel the slight, subtle itch along her spine, under her skin, as she browsed the aisles at the Fred Meyer near her apartment, trying to focus on the task at hand: getting her groceries for the week. She was supposed to meet with Bradley again that evening, at his place, and the knowledge that it would be a “training” session made her tingle all over.

  It was almost holiday season, and she’d made it clear to her boss and Master that she had no real plans to go home; she didn’t have parents to visit, no siblings, and she wasn’t all that interested in most of the friends she had left behind in Atlanta outside of recovery--besides which, those friends would be busy with their own holiday plans.

  Bradley had suggested tentatively that they might do something together for Thanksgiving, and he’d left the whole end of that week empty on his calendar. Whatever he might have planned, it was a secret from Jessica, and she hoped that that meant that he would be spending the time with her.

  She consulted the label on one of the packages of oatmeal, using the necessity to cover her need to regain her composure. Jessica and Bradley had what he called a “progress meeting” a few days before, where they’d talked about the contract, about what they’d been doing together and what they wanted to try--maintenance for their non-professional relationship.

  They’d had dinner at RingSide on Burnside Street, and Bradley had reiterated that he would never degrade her; that was still one of his hard limits. He’d encouraged her to talk about going to meetings, about the progress she was making in controlling and examining her desire to be treated terribly, and Jessica had found that while the messages that Drake kept sending her still rattled her a little bit--being reminded of her seedy past still brought up more than slight feelings of shame--she no longer felt the same pull, the same need to indulge a craving.

  In truth, her interactions with Bradley had more than satisfied her needs, though Jessica couldn’t entirely understand why. Every session they had together ended with not only the best orgasms of her life but a lengthy period where Bradley held her, comforted her, treated her as if she were made of the most delicate porcelain, as if she were precious.

  Even as she zoned out, she could--absently--hear him telling her how good she was, how wonderfully she’d obeyed, and it warmed something inside of her more and more. While Jessica was far from cured--she would still push him a bit, try and find ways to make him debase her by going beyond what her limits a
ctually were--she didn’t get the instant, gut-wrenching hunger to give into what Drake demanded of her.

  He’d gradually decreased the number of messages he sent her after weeks of no response from her, and Jessica wondered also if maybe Bradley had had something to do with it, if he’d gotten in touch with someone like he’d offered to do when she’d first come clean about what was happening.

  If he had, Jessica was glad for it--even if she was better at withstanding the temptations that Drake represented, she didn’t like the way he had of rattling her, of constantly messaging her from new numbers so she couldn’t block him once and for all.

  You could get a new number, she thought, but then she would inevitably lose people she’d been trying to maintain a connection with--some in Atlanta, some in the groups in Portland--as well as having to update everything wherever she had her contact information listed. Besides which, how was it fair that she should have to make such an effort not to be harassed? She’d made it clear to Drake that she wasn’t interested in having anything to do with him; why didn’t he back off already?

  Because--and she knew this was the reason--he wanted her. The perfect victim. The one who wouldn’t object to the things he did to abuse her, because she was willing to do almost anything for a fix. But you aren’t that person anymore, she reminded herself. She wasn’t the person who would run to his place--or to meet him at a gas station, or wherever he demanded--to get what she wanted from him.

  She had Brad. She had a good job, a good life, and more than a year and a half of sobriety. She was good, but Drake didn’t know that. He had kept tabs on her enough to know she’d moved to Portland and had apparently been dedicated enough to follow her there, but he didn’t know that she was a better, healthier person than she had been. And he thought he could get what he wanted from her. Apparently, he had given up.