by Simply BWWM
She was so incredibly aroused that the tension between her hips almost ached, and the craving in her head was for Holt to do something utterly degrading to her--to rip her panties off and begin fingering her hard and fast, or just shove his cock inside of her and begin pounding her. But she didn’t ask for it--she didn’t even let herself entertain the craving. She was too absorbed in the anticipation that was building up in her from Holt’s lengthy seduction.
Her boss spread her legs slightly, hooking his fingers in the waistband of her panties, and he slowly pulled the material down over her hips, exposing her bare, hairless pussy to his hungry gaze. Jessica bit her bottom lip, waiting for some kind of condemnation--some kind of rude comment about the fact that she was soaking wet and clearly an eager little slut, or some kind of complaint about the scent of her, something like that.
Instead, Holt flashed a pleased smile up at her. “You’ve definitely made it easy for me to do what I want,” he said, sliding one finger along her soaking wet folds. “No need to even worry about hair stuck between my teeth.” Jessica blushed, looking away.
She heard a click, and then the low, humming whirr of her vibrator; she’d almost forgotten about it completely once more in the time that Holt had devoted to turning her on so thoroughly. Jessica looked down and watched as her boss brought the vibrator towards her throbbing, soaking vulva.
He barely touched her with it, and she moaned, her toes curling and her hips shifting to try and push down towards the pleasing, alluring sensations. Holt was one step ahead of her, though, and he withdrew the vibrator just enough to keep it barely touching her labia, brushing up and down along her crease for a few moments until Jessica forced herself to be still.
He spread her labia and slowly--achingly slowly--rubbed the vibrator up and down along Jessica’s folds, bringing the blunt end up against her aroused clitoris and then down to her inner labia, and then back up again. Jessica’s hands gripped the couch as if for life itself as she struggled through Holt’s teasing, whimpering as she became more and more turned on.
“How are you feeling?” Holt’s voice was just louder than the murmur of the vibrator between her legs, and Jessica struggled to form words, knowing she needed to answer but unable to think.
“I am so fucking turned on that all I can think about is how much I want your dick in me,” she said, the words tumbling out of her without any filter.
“We’ll get there,” Holt reassured her. “Don’t worry about that.” She saw him smile briefly, and then he brought the vibrator firmly up against her clit, sending pulses of vibration through her pleasure center. Jessica cried out in pleasure, her back arching, her hips moving to get the best possible contact between the little bead of nerves and the vibrator.
Holt worked her steadily, rubbing and then retreating, keeping her on the edge until Jessica almost wanted to cry again. “Did I do something like this to you in your fantasy?” Jessica nodded, almost not even paying attention to the question itself.
“Yes--fuck, yes. Please fuck me! God—god, please, please just fuck me.” Jessica heard the clicks as Holt turned up the intensity on the vibrator, and gasped as he pressed it against her clit once more. She moaned out long and low as the fast-pulsing vibrations coursed through her, bringing her swiftly to the edge and over it. The tension between her hips snapped, and Jessica didn’t even think to worry about the gush of fluids she felt leaving her, flowing from her already-soaking pussy.
The orgasm rampaged through her, more intense than the one she’d had in the bathroom only a half hour before, and Jessica felt herself trapped in it, almost; it was so good, it was mind-obliterating--the kind of climax she had always hoped for with so many of her partners and almost never got.
By the time it began to ebb, she didn’t even know how long it had lasted. She only realized belatedly that the vibrator had been turned off, that it wasn’t even there anymore--instead, as she opened her eyes and looked down she saw Holt working her with his fingers, slowing down as he read the signals from her body that she was coming off the high of her climax.
“That--that was amazing,” she said, still slightly breathless.
“Do you still want my dick in you?” Holt held her gaze, and Jessica felt the heavy, thick heat of his erection against her lower leg, reminding her that he was turned on, too.
“Yes-- yes,” she said. Holt grinned slightly, pulling his fingers free of her pussy and licking them. Jessica trembled at the enjoyment he clearly took from licking her fluids off his hand.
“Next time, you don’t have to bring the vibrator--unless you want to,” Holt told her. “We can get along just fine with hands and mouths, I think.” He slithered up along her body and pressed damp kisses along her stomach, her breasts, and then her lips.
Jessica tasted herself on his lips, and as Holt deepened the kiss, she felt herself getting turned on all over again, knowing that he was hard, knowing that he wanted her, that he had enjoyed tasting her, that he was turned on by her.
She reached down and brushed her fingers against the bulge at the front of his jeans before giving the hard ridge a little squeeze to feel what it was like. Holt moaned against her lips and touched her all over, the two of them writhing against each other’s bodies. Somehow, they managed to get Holt’s clothes off him, and Jessica took a moment to feast her eyes on his lean-muscled physique, broad chest and shoulders and slim-strong arms and back.
Then, down between his hips, she looked intently at his hard cock; it was, she thought, seven or maybe even eight inches, just on the outer limits of the size she could imagine herself taking, thick and flushed almost purple-red from how hard it was, with a neatly trimmed thatch of pubic hair a few shades darker than the rest of Holt’s hair around the base. It was, she thought absently, an objectively gorgeous dick--probably the nicest one she’d seen.
“Are you clean?” Jessica gave herself a shake, trying to remember how to think.
“What?”
“STIs,” Holt said gently. “Do you have any?” Jessica shook her head.
“I caught one--chlamydia--but I got it taken care of over a year ago,” she told him. It was humiliating; that should have been the point when she had decided to seek treatment, but she’d still been in denial.
“You promise me that you don’t have anything I could catch?” Holt held her gaze. “If you do--if you’ve got HPV or herpes or anything like that--you can tell me. I will still have sex with you; it’s nothing to be ashamed of. But I just want to minimize my risk of also catching it.”
“No--no, I don’t have anything,” she said.
“Are you on the pill?” Jessica shook her head.
“I got the implant,” she said. “So I wouldn’t forget to take birth control or anything.” Holt smiled slowly.
“Okay then, I think we can do this without a condom--don’t you?” Jessica nodded eagerly. Finally--the voice of her addiction in her head said--finally he would pound her, fuck her senseless.
But he didn’t. Instead, Holt guided the tip of his cock against her slippery folds and rubbed slowly up and down against her inner labia, teasing them both for a moment. Then, instead of slamming into her all at once, Jessica moaned as Holt pressed into her slowly--almost painfully slowly.
He filled her up inch by inch, taking his time to let her feel every bit of his cock sliding deeper and deeper inside of her. Jessica wrapped her legs around his waist, pulled herself closer to his body, kissing him eagerly. When their hips met, Holt went absolutely still against her, holding her there, kissing her lightly on the lips.
Then, he began to move, pulling out almost completely and then pushing deep inside of her once more. Jessica fell into his rhythm as Holt moved inside of her, thrusting slowly at first, and then gradually building up speed. She pushed her hips down to meet him, twisting and writhing. She touched him everywhere she could reach, falling into the pattern that Holt had created, mirroring his attentions to her.
The tension mounted inside of her, faste
r and faster, until she wanted to almost scream for him to fuck her harder, to just pound her until he came, but she couldn’t make herself do it. It felt so good, the way Holt moved inside of her, just fast enough to turn her on more and more but never brutally, never even rough with her body. It was like he was savoring every moment of feeling her wrapped around him, every moment of the connection between them--and she wanted that too.
All at once, she felt the tension reach an almost unbearable height inside of her, and Jessica clung to Holt as she moaned and whimpered, struggling to get the orgasm she’d been building up to.
Holt reached down between their bodies and began to rub and stroke her clit as he thrust into her, and Jessica came, not even aware--at the moment--that tears had begun falling from her eyes yet again from the force of pleasure washing through her, and the intensity of her emotions and sensations. She forgot about the fear and desperation she’d been feeling, the uncomfortable vulnerability, as the climax raged through her, and only barely felt Holt’s body tensing against hers as he hit his own limit and then came, buried deep inside of her, the sticky heat of his fluids mixing with her own.
She lost all ability to think about anything at all as they rode through their mutual climax, continuing until they were both spent, and then Jessica let her body collapse against the couch, as she panted and gasped for breath, locked in the tingling aftershocks of so many bouts of intense pleasure in such a short time.
Chapter8
Bradley sat back in his desk chair and looked out over his office, smiling slightly to himself. He couldn’t remember a time in his life when he was more consistently relaxed than he’d been in the month since he and Jessica had begun having sex together; of course, he thought, that kind of relaxation was a natural result of getting off up to five times a day, but it was still a pleasant change, and one he hadn’t entirely anticipated.
Gradually, Jessica had opened up to him about her addiction, though she’d shied away from giving any specifics--and from Brad’s point of view, the specifics of who she had done what with, or which sex acts in particular she’d done, were not all that important. Instead, he’d focused on what he could do with her, what would be safe for her, how they could both set boundaries. He’d contacted Kevin, his friend from Stanford, and gotten advice about the situation, keeping the details to a minimum; Kevin had been full of advice.
“Your friend is probably going to be in a fragile state of mind for a while longer,” he’d said. “If she chose to remain abstinent after leaving treatment, she’s been scared that she’ll fall into old habits readily--and that fear is something she needs to address. But it needs to be in a safe environment.”
Kevin had gone on to give Brad advice about discussing boundaries, about inquiring about her triggers and how to identify symptoms of relapse. “With luck, it won’t come up--but that’s something that everyone who deals with addicts has to be aware of: relapses happen.”
His main focus had been on making sure that all his interactions with Jessica were respectful, which Kevin had told him was a major benefit. It had sounded to Kevin like a major part of Jessica’s addiction was rooted in self-esteem issues; while he hadn’t revealed any specifics, he’d generally outlined the kinds of requests that Jessica had made to be rougher with her, to use cruder language with her.
“It’s easier for the addiction to thrive if she doesn’t view herself as a person with agency, worth respecting, a complete human being,” Kevin explained. “Showing her steadfast respect, making sure to show her value and humanity--that will be difficult for her to take first, but it’s something that will help her heal.”
Brad smiled to himself slightly, remembering one of their most recent “sessions.” He had been in the middle of working Jessica with his mouth, worshipping her sweet-sharp tasting pussy, when he’d realized that her shaking was not from pleasure--or at least, not just from that--but from the fact that she was crying.
That was when he’d learned from her that it had been years since any of her partners had gone down on her--or at least, more than just a cursory trip “downstairs” as she put it, to get her wet enough to go onto the next stage of sex. She couldn’t even remember the last time someone had brought her to orgasm orally, or the last time that someone had gone down on her specifically to get her off. That seemed so incredibly sad to him, in a way; for a few minutes, they just laid there on the couch, discussing it as Brad continued to gently touch and play with her--not enough to keep her from speaking or to distract her, but enough to keep her aroused.
It had still been alarming--almost distressing--to see Jessica occasionally crying during their trysts, but Brad had started to understand that it wasn’t, usually, a bad thing. He always stopped and checked with her, but so far it had always been a matter that she was overwhelmed by something positive: something she hadn’t thought she deserved or that she had become accustomed to not receiving.
It was, Brad thought, overall healthy--and he hoped that it was good that he was able to handle the situations without becoming upset himself, at least not visibly.
A notification popped up on his computer screen, and Brad shook himself out of his thoughts to see what it was. One of his upper-level management wanted to hire someone to be a business assistant--and he’d narrowed the list down to four people: two men and two women. He wanted Bradley’s input on the potential hires and had submitted a potential window of time for Bradley to join in the interviews.
Since the company was still very much under his control--this one hadn’t even gone public yet--Bradley did like to take an active role even in lower-down hires, though entry level employees only had to go through the hiring manager and HR. He quickly typed up a reply and looped Jessica in, to make sure that his schedule would be clear, and she would know to expect him to be out of his office at that particular time.
As he relaxed again for a moment, it occurred to Bradley that during their lunches, he and Jessica had talked about what she could do around the city, what sights she could see and what hobbies she might be able to pick up, but he hadn’t--yet--heard anything from her that she’d actually tried anything.
She seemed to be fairly knowledgeable about the neighborhood around her apartment in St. Johns, and she’d clearly found out some things about the area directly around the office building, in the Pearl District, but as far as Bradley knew, his assistant hadn’t even managed to make any real friends in her new hometown.
“That can’t be healthy for her,” he murmured to himself. People that she met at meetings, while important for her recovery, shouldn’t--he thought--be the only social life she had. She shouldn’t be restricted to work, home, and grocery shopping. She should be getting out there.
After living in the city for years, Bradley had a fairly broad idea of what there was to do--and he thought with a little tingle of temptation that it actually would be nice to see his assistant outside of the office context. Careful--are you doing this for the right reasons? Bradley stopped in the midst of opening a tab to look for options he could set up for the two of them to do.
He’d done things outside of the office with most of his assistants, but that was more as a matter of convenience. He brought them along on occasion for events that he himself had gone to, just for the sake of having someone there who knew his schedule in case someone tried to arrange dinner or invited him to some other event, or in case he needed arrangements to be made wherever it was he was going--things like that. Occasionally, when he had to go out of town for business, it had become a part-vacation for whoever his assistant was at the given time, since they could manage his schedule from the hotel where they had a room a few doors down from his.
But this was different, and that meant that he had to think carefully about why he was doing it. He cared about Jessica, certainly; he’d cared about all of his assistants. Hadn’t he made sure that Jake had everything he needed to relocate with his wife? But even as he tried to deny any kind of conflict, Brad knew that it was denial-
-pure and simple.
He cared more about Jessica on a personal level than he had about any of his previous assistants, rather than a professional one, and the fact that they were having sex regularly contributed to that. He had a connection with her that he quite simply hadn’t had with the other assistants he’d hired.
“That doesn’t mean it’s wrong, though,” Brad murmured to himself out loud. Just because he was more personally concerned about Jessica didn’t mean that he was overstepping his boundaries with her, did it? He put in a search term in the tab to pull up options for things they could do in the city together.
Outside, it was raining--as it so often did--and he made a little mental note to stick with indoor things, just in case. Seeing Jessica outside of work didn’t have to be a problem, even if they were already having sex. They managed to keep things professional when they needed to be professional--didn’t they? Brad thought about that for a moment. None of their trysts had been during their normal professional work together--none of them were even, really, spontaneous.
They were scheduled for lulls in the work day, for both of them. No one was or would be any the wiser about it; Jessica had so far been very careful to make sure that there wasn’t even a possibility that someone might arrive early or their “meetings” would run late over into another engagement or visitor coming to see him or anything like that.
So, Brad decided firmly, he would make tentative arrangements and then send Jessica the details, and he would let her know that if she wasn’t comfortable with it, she could turn him down--no questions asked, no pressure, no blame.
His scanning gaze fell on one choice, and he smiled to himself. It was so perfect: cheesy and genuinely interesting in equal measures. And it would be fairly easy to arrange something, to make it special. Brad thought for a moment and then sent an email to start the process, before opening a new email to send to Jessica--to her personal, rather than her business email, but he knew that she could access both from her desk, and often did.
