Chapter15
Bradley guided Jessica through his front door into the living room, watching as she took her shoes off at the door and set them aside. He sat her down on the couch and went into the kitchen, glancing over what he had available to drink before settling on a bottle of Calvados. He decided to make coffee to go with it and started up his expresso maker, glancing into the living room to see how Jessica was settled in.
It had been a difficult afternoon for her, and Bradley felt infuriated in the knowledge that Drake’s harassment of his personal assistant had now escalated to in-person assault. He would have to do much more than he had to protect Jessica. For now, though, you have to make her feel safe. You need to help her handle what just happened.
The police had been fairly considerate, and they’d definitely been sympathetic--especially when the security footage from the store’s cameras had shown the situation had gone down almost exactly like Jessica had said. Of course, since it was silent, there was no way to know what she’d actually said to Drake, but it was clear that she hadn’t wanted to be groped and that she’d given him plenty of warning before turning around and defending herself.
Even still, Drake had thrown more than enough mud into the gears to make the situation difficult for Jessica, and Brad could only be glad that she’d had the presence of mind to destroy the man’s phone, so he couldn’t show the cops the salacious and humiliating pictures he had of her. He’d praised her for that cleverness as he’d driven them back to his place, and parked in the attached garage structure, but it was clear that Jessica was exhausted and that she needed support.
As soon as she’d texted him, Bradley hadn’t even considered not coming to her aid. He knew how difficult it was for her to deal with the situation with Drake, even when it had been limited to text messages; he didn’t want her to have to deal with talking to the police and responding to the disgusting man’s accusations and comments on her own.
Brad wasn’t sure when exactly he’d given into the knowledge that he had real feelings for his personal assistant and submissive, beyond the parameters of their official relationships to each other, but he knew that it was too soon by far to address that. He would have to take things slowly, and he would have to wait until she was ready to talk about an actual romantic relationship, and in the meantime, he would have to support her as best as he could.
“Just the thing for a time like this,” Brad said, bringing the cups of espresso, some milk and sugar, and Calvados into the living room. Jessica looked up, and Brad saw her give herself a shake to pull herself out of her torpor.
“Sorry, that was just kind of a lot,” she said, taking a breath and giving him a weak smile. Brad set one of the mugs of coffee down in front of her on the coffee table and offered her the hot milk and the sugar. He poured a shot of Calvados.
“You handled the whole thing extremely well,” he told her. “And you’re safe. They took him to jail, and he’ll have to make bail or stay overnight if they don’t set his bail tonight. He won’t want to bother you again.” Jessica smiled again, a little more genuinely.
“There is that,” she agreed. “Maybe now he’ll catch the clue that I want nothing to do with him.” Bradley nodded and leaned in, giving Jessica time and space to pull away from him if she didn’t want him to continue. When she didn’t tense up or move away, he closed the distance between them and kissed her lightly on the lips.
“So, let’s have coffee and Calvados, and then let’s have a little...session,” Bradley suggested. “No punishment, no pain--it’ll be all about you.” He had been planning the session they were supposed to have for days, but knowing what Jessica needed in that moment, he abandoned entirely the idea of what he’d thought he was going to do, in favor of something that Helena had taught him about called “care play.”
He’d been studying up on dominance and submission, about the dynamic that could happen between the two people in a scene, and Bradley had filed away--for mental reference--ways that he could encourage Jessica to work through certain things, to help her process. There was, he’d learned, an entire subset of BDSM culture that had as its goal helping victims of abuse and other traumas to come to terms with and work through what had happened to them.
While Jessica had always been clear that the degrading things she’d done had been her choice, Bradley wasn’t entirely sure how much of that was true; she’d been in the height of her addiction, she’d been vulnerable to people like Drake, who were looking for someone who would give into them for the sake of whatever “fix” they were offered.
Why Drake hadn’t just moved onto another victim when Jessica had become inaccessible, Brad wasn’t sure. But he made a mental note to contact a few people he’d tentatively talked to about the man. There had to be something to do to track him down and--legally--convince him that it was in his best interests to stop even attempting to go after Jessica.
“A session?” Bradley nodded slowly.
“If you feel up to it,” he said. “No pain, like I said. I won’t be punishing you. I am really proud of the way you stood up for yourself, and I want to reward that.” Jessica smiled slowly.
“I’d like to try that,” she said. Bradley kissed her lightly again and watched as she prepared her coffee. He handed her the shot of apple brandy.
“You can either add it to the coffee, or you can take it as a shot separately,” he told her. Jessica considered for a moment and dumped the gold-tinged alcohol into her almost-full cup. Bradley nodded his approval and went to work mixing up his own drink.
They had been working hard on her “training” in the past few weeks, and there was something that Bradley wanted to do with Jessica that he thought would be good for them to explore that night.
He’d been putting it off, approaching the topic as obliquely as possible, and only barely playing with Jessica anally, but he thought--he hoped--that that night would be a good opportunity for moving forward, for using that as a way for Jessica to process and work through some of the mental garbage she was still dealing with regarding Drake.
Brad gave himself a mental check. Are you thinking about this because it’s really something that might help her, that might be good--and enjoyable--for her, or because you’re fascinated by the idea? If you’re only doing this to take advantage of how vulnerable she is, you had better never do it.
Bradley sipped his coffee and then knocked back the slightly fiery brandy, thinking about the question. He wanted to try anal with Jessica, especially in the context of her submission to him, but he knew himself well enough to know that even if Jessica didn’t use her safe word, he would stop if he felt that she wasn’t enjoying it even for a second. He would make himself stop. And if it seemed like she really wasn’t enjoying it, he would never pursue it again unless she specifically requested it.
He made small talk with her, letting the atmosphere relax between them, letting Jessica decompress from the stress of talking to the police, listening to them repeat Drake’s accusations--even if they hadn’t believed them--and telling her story more than three times to five people altogether. Brad read Jessica carefully and knew when she was ready to move into the session itself; she was fully relaxed, and the small amount of alcohol had done its work, removing the raw edges from her shock and discomfort. He would take care of the rest.
“Stand up please, Jessica,” Brad said, accepting the empty mug from her. “You know how I want you to begin: take off all of your clothes.” He took out his phone and scrolled through his Spotify playlists until he found one he thought would suit: Fiona Apple. He started the music and watched as Jessica stripped out of her jeans and sweater, taking her time the way she knew he liked.
She hadn’t been prepared to meet with him--hence why she hadn’t worn a dress or skirt, and her bra and panties were mismatched, the bra in a deep eggplant and the panties black with lace edges. But there was something nonetheless charming about watching Jessica strip herself down to her skin, watching the submissive mindset work its way through her, the desire to please him and do as she was told.
When she finished, standing naked in front of him, waiting, Brad stood. “What I need is in my bedroom, and I think it would be best if we moved things there, don’t you, Jess?” He’d taken to calling her “Jess” with a certain emphasis when they were in a session together, as a substitute for calling her his slave or any of the other terms. He wanted to keep her in her own humanity, but also separate the way he addressed her in a scene from their normal interactions.
“Yes, Sir,” Jessica agreed. Brad took her hand, picked up his phone to bring it with them, and guided her towards his bedroom. He thought about what best to do--how best to work up to what he thought would be the main event of their session that evening--and how he could put the growing collection of toys and implements he had in his bedroom to use to that end.
He considered what he had, and as he let Jessica into his room, keeping the door open so that she could leave if she wanted to, he decided the first thing to do would be to get her into the proper zone.
“Stand right here,” he told her, letting go of her hand. Brad moved to the separate set of drawers he had started filling up with his “collection” and opened the top one: in it, there were various types of restraints including cuffs, different ropes--from slightly rough to silky-soft all the way to a carefully selected synthetic rope that would feel very harsh but wouldn’t actually damage the skin, and more. The drawer also had blindfolds and the two gags he’d so far purchased, and a few other items that he’d purchased to somehow immobilize or corral his submissive.
He made his selections. “We’re going to be doing things differently from usual tonight,” Bradley explained, taking out a spreader bar with cuffs on either end, as well as a silken rope, and a blindfold. He turned to face the naked woman in his bedroom, and took in the sight of Jess’s lush, delicious body.
“How?” Bradley moved towards Jessica, the restraints and blindfold in his hands, letting her see them.
“You can make as much noise as you want. You can say whatever you want. In fact, my rule for you in this is for you to tell me how everything I do to you feels, exactly as you feel it. No wrong answers.”
“What are you going to be doing to me?” Bradley smiled, setting the restraints down on the bed and holding up the blindfold.
“That is going to be a bit of a surprise as we come to each thing,” he said. “But repeat after me: my body is mine to control.”
“My body is mine to control,” Jessica said.
“Good girl,” Bradley said. “You control this ultimately. If I do anything that you don’t like, or you don’t feel comfortable with--you don’t even need to use the safe word. Just telling me no, or slow down, will get what you want.” He leaned in and kissed her.
“But I want you to be completely in the sensations, which is why I am going to be blindfolding you and putting on the restraints. If you get uncomfortable or want to stop, you know what to do.” Jessica nodded.
Bradley put the blindfold on her, tying it tightly enough that she definitely wouldn’t be able to see but not so tightly that it would hurt, and checked to make sure that she absolutely couldn’t see through it. He took her hands in his and put them in front of her body, crossing them at the wrists.
Trustingly, Jessica left them there, and he tied them with the silken rope, immobilizing them in front of her body. He would be able to put them over her head, but the position wouldn’t be as uncomfortable as behind her back. Finally, Brad knelt down and spread Jessica’s legs, attaching each of the cuffs on the ends of the spreader bar to her ankles. Already, he could tell, she was wet--turned on, just from the novelty and the anticipation.
“I got something new installed in my room a couple of days ago,” Bradley informed Jessica. “I think you’ll like it.” He pressed a button on the wall, and a hook came down from the ceiling, slowly making its way down on the chain it was connected to.
Bradley gently took Jessica’s bound hands and lifted them, keeping the tension through her arms as lax as possible, and hooked the rope binding her wrists above her head. He stepped back over to the wall and pressed another button, and the hook rose slowly, one link on the chain at a time. “Are you comfortable, Jess?”
“Yes, Sir,” Jessica said, and Bradley heard the breathless desire in her tone.
“Do you feel nicely helpless?” Jessica smiled.
“Both of those things, Sir,” she confirmed. Bradley chuckled. He moved back to the dresser where he stored his toys and implements and opened another drawer. This one contained different items--nothing that would hurt, only things that would feel good, or at least that Bradley hoped would feel good. He selected a couple of new vibrators, and a few other items, including two anal toys in different sizes, along with lubricant and a cleanser. He would use those later.
Just the sight of Jessica, arms confined over her head, legs spread wide, fully naked, was enough to make Bradley start to get hard, and the anticipation of knowing that he was about to make her feel amazing--that he would feel her getting wetter and wetter, hear her moaning in pleasure, all of the sensory details of her arousal and eventual climaxes was thrilling. He took a deep breath and set the toys aside, where they would be in easy reach on the bed, and began to strip down to his jockey shorts. “Are you ready to begin?”
“Yes, Sir,” Jessica said. Bradley approached her with a bottle of massage lotion; it was flavored, with some type of ingredient that provided warm and cool sensations, and safe to use with the silicone and plastic toys he owned. He squirted some into his hand, and surveyed Jessica’s body, choosing where he would start.
He rubbed his hands together slowly, and then cupped her breasts, spreading the oil onto them and beginning to massage them. Jessica moaned--and the sound cut off with a gasp as the heating-cooling ingredient in the lotion activated.
“Do you like this, Jess? Tell me if it burns or starts to sting,” Bradley told her, keeping the firm tone that he used in their sessions.
“Y-yes Sir,” she replied. “It... oh, it feels really, really good.” Bradley massaged her breasts thoroughly, giving the lotion plenty of time to work, and then leaned in, claiming her nipples one after the other with his mouth. The lotion tasted pleasantly of cherry and cinnamon, like some kind of fruit crisp.
Brad didn’t really need the taste; sucking and licking Jessica’s nipples was pleasing on its own. But he could see that the heating and cooling effects of the lotion were definitely doing good things to Jessica: she was squirming, twisting against the bindings on her wrists, moaning more and more as he worked her with his mouth and lotion-coated fingers.
He didn’t touch her pussy--or, yet, her ass--since he didn’t know whether it would be wise to introduce something that would tingle that much to such delicate skin. Instead, Bradley massaged her breasts with more of the lotion, and then moved to her thighs, rubbing and kneading the muscles there, and then licking upward from her knees towards her already-soaking pussy. He dropped back down to her inner thigh, just above her knee, and moved upwards again, avoiding the spot that he knew Jessica wanted him to lick and kiss the most.
Bradley smiled to himself as Jessica became more and more turned on, moving and squirming in her helpless state. “Is this good to you, Jess?” She nodded, panting slightly.
“Yes, Sir,” she said. Bradley decided to move onto the next phase of his plans, and stood, moving to the bed where he’d left the toys he’d selected. He picked a pair of vibrators specially shaped and designed for nipples, and pressed them over Jessica’s hardened nubs, flicking the switches on the side of each one. Jessica gasped and let out a long, low whimper. “Ohhh,” she said, her breath hitching in her throat.
“Do you want me to take them off?”
“No sir,” she said quickly.
“Tell me how nice they feel, Jess,” he commanded.
“Oh--oh, god, they feel--fuck…” Jess struggled, as if getting her arms free of the bindings on her wrists would make it easier for her to think. “It feels so good, Sir. It feels so nice buzzing on my nipples, I feel like I could come right now.”
“You can’t come yet, Jess,” Brad told her, making his voice even firmer.
“Yes, Sir,” Jessica said. “Please?”
“Not yet,” Brad said, amused. “I’m just getting started.” He turned on another vibrator, this one a cordless Hitachi wand--from Japan, no less. He’d charged it the night before, with different ideas on how to use it on her, but it was going to be just as handy for what he had in mind for his submissive in light of recent events. He turned it on and slid the rounded head down along her torso, teasing her with it.
He brought the buzzing, humming head then up along her thighs from her knees, and finally placed it squarely and firmly against her clit, spreading her labia gently. Jessica cried out, straining harder at her bindings, trying to close her thighs around the wand and his hands to keep it there.
Brad teased her relentlessly, pressing the massager against her clit and then withdrawing it, turning her on more and more, bringing her to the edge of climax and then backing off when he felt her tension mounting to the point where it had to break. “Please. Please, Sir,” Jessica whimpered.
“Come for me, Jess,” Brad told her, holding the wand’s head against her clit. “Come good and hard.” He turned the intensity up to maximum, and she let out a long, low moan that almost took on the note of a shriek, shaking from her head to her feet as she came, gushing around the round massager head.
“Oh--oh, fuck, oh yes, fuck...god, Brad…” Words fell from her lips in an incoherent jumble, and Brad made her climax last as long as possible, ignoring the throbbing of his own cock, his own fiery arousal aching along his groin. He wanted to be inside of her--deep inside of her--but he would wait. He would be patient.
When he was sure that Jessica was spent, Bradley slowly turned down the intensity of the vibrator and then began to pull it away, setting it aside on a towel to clean for later. He gently removed the nipple vibrators and turned them off as well as Jessica panted and gasped for breath. “I think this is long enough for you in this position, don’t you?”
“Y-yes, Sir,” Jessica replied breathlessly. Bradley pressed the button on the wall to release the tension on the chain and took Jessica’s wrists down, though he kept them bound in front of her.
“Do you want to lie down, Jess?”
“Yes, Sir,” she replied. Bradley kept the blindfold on, kept her bound exactly as he’d had her, but gently laid her down on his bed, on her back.
“How are your shoulders? Anything hurting?” Jessica shook her head.
“No Sir, I’m fine,” she replied. Bradley smiled to himself and pressed his hips against her thigh. He wanted her almost too much to be able to bear it, especially looking at her like she was: naked, helpless, utterly trusting in him, flushed still from the intense climax she’d just had. Plenty of time for that. You have more work to do.
He sat up and picked up another one of the toys, looking at Jessica. She was still in the aftermath; he needed to start gently. “Are you ready for more, Jess?”
“I need a minute, Sir,” Jessica replied, and Brad nodded to himself, looking at the things he had brought to the bed.
“Do you want to be untied?” She shook her head.
“I’m okay, Sir,” she said. Bradley considered the options in front of him. He wanted to get her as fully aroused as possible before he tried to do anything with the anal toys he’d brought out--he wanted her in the best possible state of mind, and having already gotten off, she would be a little less likely to agree to something she didn’t want. But, Brad thought, if he approached the anal play the right way, she would be receptive to it. If it doesn’t happen tonight, don’t try and force it, he told himself.
He went to work without toys, kissing Jessica lightly and then more passionately, touching her everywhere but her pussy, caressing her and holding her, letting her feel how much he cared about her, taking his time to turn her on again.
Brad reached down and chose another vibrator from the assortment of toys at the foot of his bed, and when Jessica seemed to be as turned on as she could be, as ready for it as possible, he slowly inserted it into her soaking wet pussy, pressing its thickness inside of her bit by bit. It was only slightly larger than his own cock, and as the vibrations pulsed, he watched Jessica arch and twist, moaning and whimpering helplessly.
“Do you want more, Jess?” She nodded.
“Yes, Sir,” she said, her voice cracking slightly.
“Tell me what you want, Jessica,” Bradley commanded.
“I want you to fuck me, Sir,” she told him. “Please?”
“Not yet,” Bradley said. “Would you rather come all over this vibrator?”
“I want your dick,” Jessica replied, her voice taking on an almost pleading note. “I want it so much.”
“Do you want it in your mouth, while I leave the vibrator right here?” He clipped on an attachment to the vibrator: a little device that pressed against Jessica’s clit, stimulating that as well. Jessica whimpered.
“I want--please--please, Sir, I want your dick.” Brad slithered out of his jockey shorts and began to stroke himself slowly. It provided a little relief to the aching throb that had taken up residence in his balls, along his groin. He wanted more than anything to bury himself deep inside Jessica, but he wanted to make her come as many times as possible and wanted to make her feel as good as she could ever feel.
“Where do you want my dick, Jess?” She shook her head, not rejecting the question--Brad knew--but struggling to be able to think clearly.
“My mouth. Please fuck my mouth, Sir,” she begged. Bradley smiled slightly to himself. He gently put her hands over her head and maneuvered himself so that he knelt above her chest, not pinning her down, but with the tip of his cock just inches from her panting, half-open mouth.
“Tell me what you want again, Jess,” Bradley commanded.
“Please fuck my mouth, Sir,” she said, sounding desperate. She was, he knew, becoming almost unbearably turned on by the vibrations buzzing through her pussy. He would make her come again, and then he would--he thought--have her ready for the final round. Bradley gently pressed his cock past Jessica’s lips and groaned in pleasure as she immediately went to work, worshipping him with her lips and tongue as much as her position allowed.
He held himself back, intent on not doing anything to degrade or hurt Jessica, moving his hips so that she could take as much of him as she wanted. As she moved closer and closer to orgasm, she also sucked him harder and harder, more eagerly, swallowing own the fluids that began to flow from the tip of his cock. Bradley could feel himself beginning to respond to Jessica’s obvious arousal, her neediness to come, and he only barely managed to pull out of her mouth with a few moments to go before he would come. “Do you want me--Do you want me to come in your mouth, Jess?”
“Yes, yes please--please, Sir, please come in my mouth,” Jessica said.
“I will,” Bradley promised her. “And if you need to come, you can come as hard and as long as you want.” He pushed his dick back into her mouth and gave into his impending climax, holding himself up so that he wouldn’t smother her or pin her down as wave after wave of pleasure washed through him.
He felt Jessica coming fast on his heels, her body shaking underneath him. She almost choked on the last of his semen, but when Brad--only half-conscious with orgiastic relief--checked on her, she’d swallowed it all. He sank down onto the bed next to her and watched as Jessica’s orgasm continued.
When he was sure she was done, he withdrew the vibrator once more. “Was that good to you?” Jessica nodded, still panting and gasping for breath.
“Very good, Sir,” she said.
“I’m going to untie you now, Jess,” he said. “But I want you to keep the blindfold on.” He unbound her ankles and wrists, and Jessica curled up to him trustingly, not even moving to touch the blindfold as he held her. She was shaking, her tremors only gradually subsiding as he stroked her body slowly.
“Thank you, Sir,” Jessica murmured. “That was amazing.” Brad kissed her lightly on the small bit of her forehead that showed above the blindfold.
“There’s one more thing I want to do, but I want you to tell me honestly whether it’s something you’re okay with,” he said. “Don’t say what you think I want to hear. Do you understand?”
“Yes, Sir,” Jessica said. She tilted her face up as if to look at him, in spite of the blindfold. “What’s that?”
“I want to play with your ass, Jess,” Brad said gently. “I want to give you the experience of being played with anally for your pleasure. If you don’t like it, we’ll stop immediately. Are you okay with that?” He had to wait a moment for her to consider it, and Brad thought that was a good sign.
“You want me to…” she licked her lips. “I’m not sure.” Brad kissed her on the lips, lightly.
“If you don’t want to do it, I’ll take the blindfold off, and we can relax for a while and when you’re ready for me to fuck you again, we will do it the normal way,” he told her. “I won’t be mad at you, I won’t deny you more play as soon as you’re ready.”
“You promise that if I don’t like it, you’ll stop,” Jessica said, making it not quite fully a question.
“If you even seem like you don’t enjoy it, I will stop,” Brad said. “I want you to only do what you’re comfortable with, what you like.” Jessica considered for a moment.
“Can we do it another night?” In response, Bradley reached around Jessica’s head and took off her blindfold, smiling at her.
“We can do it whenever you feel comfortable--and if you never feel comfortable, we won’t do it,” he promised her. She reached up and pulled him towards her, kissing him eagerly.
“Thank you, Sir,” she said, and when Brad pulled back, he saw that there were tears--happy ones--in her eyes. “Thank you.”
“We will never, ever do anything you don’t want to do, Jessica,” Brad told her, keeping his voice firm but gentle. “You are always safe when we play.” He held her tightly to him and felt her tremble, knew there was more work to do--he could save exploring anal for another night, another occasion. He was making progress with Jessica, and that was what was important.