Shades of Step Billionaire

by Harlow, Jenna

  Soft skin, firm and dense pressed along her bottom lip. Her immediate urge was to let her tongue out to explore and taste him, but she waited. Instead, she focused on the feel of the soft skin as it moved over her lips, filling her with the anticipation of feeling him fill her mouth. “Good waiting, Olivia. You’re learning quickly,” he said. With the blindfold on, her other senses sharpened. The feel of his cock, warm and smooth like silk against her lips, the musky smell of his manhood so tantalizingly close, and even the sound of his voice, thick and throaty with desire were all amplified. Just when she thought she couldn’t wait any longer Jeremy nudged her mouth open with his thumb. “Okay, Olivia. You’ve waited long enough.”

  Eagerly, she reached out with her tongue and circled around his tip, giving special attention to the soft skin underneath. From there, she swept over the shaft down the length and back up. It was impossibly large, long and thick. She worried whether she would be able to handle it or not. Once it was completely wet, she opened her mouth wide and slid her mouth over it. She only had her tongue and lips to use to guide it along.

  She moved slowly, carefully. She wanted to take her time, and let him sense how much she was enjoying it. Jeremy moaned, and began to move in tune with her. It was tricky, keeping control of his cock, the rhythm and placement of it in her mouth, without being able to touch it with her hands. She hung helplessly, suspended by ties she couldn’t see. The situation was challenging, and she found it astonishingly erotic. She was in a submissive yet somewhat controlling position. She ached to please him as much as she yearned for him to satisfy her.

  She usually dreaded giving head. She had only ever done it with Trent, who would always grab her by the back of the head and shove onto her knees as a way of asking for it. He always made her feel cheap and used. With Jeremy, she wanted to taste him, wanted to feel his cock filling up her mouth, and know she was giving him pleasure. For the first time in her life, giving head felt like a privilege instead of a chore.

  Their motions grew faster, her head bobbed toward his now thrusting cock, which pushed deeper and deeper down her throat with each forward stroke. His hand was on the back of her head now, pushing him toward him. She could sense how close he was and silently willed him to release. Just as she thought he was going to explode, he grabbed a fistful of her hair at the nape of her neck and pulled her away. She thought to protest, but again refrained, reminding herself to not argue or question his methods. Instead, she remained still. It was dark behind the blindfold, and now the room was quiet. For a moment, the only sensory stimulation she was aware of was of her own throbbing cunt, which was aching for Jeremy.

  “Very good, Olivia,” he said. “Now let me reward you.” Olivia felt the clasps release and Jeremy’s hand on her elbows, guiding her to a standing position. He nudged her forward until her thighs were pressed up against the bed and then pushed her down against the mattress. He fastened the clasps of her ankle straps to the corners of the bed, and her wrist straps that came up from under the bed. It was like a bent over spread eagle position. Olivia waited, anxiously anticipating what would come next. Every delay was like delicious torture. She knew he was doing it on purpose. She was so desperate for him she wanted to cry out and beg, but she didn’t, knowing that would just result in more waiting.

  “Are you ready, Olivia?” He asked softly. She shuddered as he flicked her nipple with the riding crop. He traced a trail down the side of her body, driving her wild with desire.

  “Yes!” she replied, her voice nearly shrill with need. He let the crop follow along the line of her thigh and down her inner leg. “Oh, Jeremy please,” she begged. She couldn’t stand it any longer. The feel of the riding crop near her wet cunt was too much. “No begging, Olivia,” Jeremy admonished again with a flick of the leather riding crop. She wanted release so badly, she was almost grateful for the pain; it made it possible for her to hold on a few seconds more.

  “Olivia,” Jeremy said, trailing the crop against her backside. “Do you know what I want from you?” Now he was toying with her. She wanted it so badly and he was drawing it out further. She knew she’d have to rein it in and regain some composure or he would continue to torture her with delays. She took a deep breath before answering, considering her response carefully.

  “Complete submission, with no questions or arguments.” She was nervous, but she kept her voice was steady and calm. He was silent for a moment and softly traced a line down her thigh and back with the riding crop. She braced herself for another strike, her heart jackhammered in her chest as she waited. After what seemed like an eternity, he moved closer to her.

  “You’ve answered wisely, Olivia. You’re ready.” Olivia let out a long breath, relieved by his response. As her entire body briefly relaxed, she was stunned when Jeremy suddenly thrust inside her from behind. She gasped, shocked as his cock drilled into her. There was no slow build up or gentle entry. He impaled her with unbridled force, and it was just what she needed. The moment his searing cock filled her hungry pussy, she was so desperate for him that she instantly cracked open. Her throbbing cunt clenched down on him and she screeched, releasing a primal scream as shockwaves of ecstasy rocked her entire body. His hips pistoned into her, driving her deeper over the edge. The thunderous convulsions continued to reverberate through her and she screamed again, releasing all the pent up tension she had held inside. As she let loose the fury within, Jeremy lurched and swore as his own release overtook him.

  Olivia lay motionless as her body recovered. She was tired, sweaty and breathless and she had never felt so free and alive. She couldn’t remember a time when her body felt so completely relaxed. It was as if all the stress and tension in her life had melted away, leaving her feeling completely rejuvenated.

  “That was amazing!” she exclaimed. She couldn’t believe how incredible the entire experience was. It not only exceeded her expectations, it blew them away. She relaxed against the mattress, letting her breathing return to normal as Jeremy unfastened her restraints. She was barely aware that he disappeared into the next room for a moment and returned with a bathrobe for her. Olivia stretched and yawned as she sat up, realizing how tired she was. She imagined she would sleep like a baby. Overcome by the desire to sleep, she started to crawl into bed as Jeremy returned. He was carrying a bathrobe. He reached out and placed his hand on her elbow, gently guiding her away from the bed.

  “That bed isn’t for sleeping,” he said, handing her the bathrobe. “I started the shower for you.” Olivia really just wanted to collapse into bed and fall asleep in his arms, but she didn’t want to seem rude. She took the bathrobe and headed toward the door.

  “Aren’t you coming?” she asked. Jeremy shook his head. “No, you go ahead. I want to straighten up in here. I’ll shower later.” Olivia turned and headed to the bathroom. She washed quickly and dried off, eager to crawl into the giant bed and feel the luxurious sheets against her skin. She came out of the bathroom and frowned as she again saw Jeremy unrolling his sleeves, and buttoning his cuffs, just as he had done the night before. An uneasy feeling settled over her.

  “You aren’t coming to bed again are you?” she asked. It was more of a statement than a question, as she suspected she already knew his answer.

  “No. Not yet.” He kissed her on the forehead and guided her into bed. “I’ll try to finish up soon.” He pulled the cover over her as she reclined in the bed.

  “Oh,” she said, her voice tinged with sadness. She hoped there wouldn’t be a repeat of last night. She really didn’t want to wake up alone again. She rested her head against the soft pillow as Jeremy turned off the light and shut the door. As she drifted off to sleep, she mulled over the events of the last few days. She was still uncomfortable with the fact that Jeremy was her stepbrother, and she had no idea how her stepfather would react if he ever found out about the two of them. She realized of course, that he would probably never find out unless things got really serious between her and Jeremy, and it was definitely way too prematur
e to even think about that happening; premature, maybe, but definitely entertaining. She imagined briefly, what life would be like long term with Jeremy. She could definitely see herself happy with him. He seemed like the perfect man. Olivia sighed as she filled her head with dreams of the future and drifted off to sleep.

  Chapter 17

  Jeremy ignored the work email he was supposed to be typing and stared out the window instead, distracted by thoughts of Olivia. She was an incredible woman, more exciting and eager than he could have hoped for. This weekend cemented in his mind what he had concluded the first night he met with her at the restaurant: He wanted her- in his life, in his bed and under his command. So far, she had been an excellent submissive. For someone so inexperienced, she was willing and fearless. That was good; he just hoped it stayed that way. She had only seen a glimpse of his world, just barely had a taste. A scowl cast over his face. She was eager and willing now, but he wondered. Would she be able to accept him if she knew everything, could she handle the darkness inside him? Olivia wasn’t just someone to fuck, he cared about her. He didn’t want her to end up getting hurt. A knot pitted in his stomach. He worried he was playing a dangerous game. He cared about her too much to put her at risk, but he wanted her too much to let her go. For now, he was willing to push things, see how far she could go. He only hoped he could stop before he pushed her too far...

  His thoughts were interrupted as Olivia walked into the sun filled room. She smiled dreamily at him as she took a seat at the table. Jeremy froze, enamored by her appearance. She looked nearly angelic. Her hair cascaded in soft curls over her shoulders and she still seemed to have sleep in her eyes. Jeremy had been with many beautiful women before, models, actresses, but none of them compared to how beautiful Olivia looked. She had a realness that they lacked, an authentic quality that he had not been able to find in anyone else.

  “Morning,” Jeremy said.

  “Morning,” Olivia yawned.

  Jeremy poured her a cup of coffee. “You look nice,” he said, indicating to the new clothes she was wearing. Olivia looked down at her outfit. She was wearing a teal colored silk blouse paired with black pants and matching flats. She smiled, laughing softly.

  “You’re spoiling me. I couldn’t believe it when I saw you had bought me another new outfit. I love it, thank you.” He knew he was coming on strong with the gifts, but he couldn’t help himself. What fun was it being a billionaire if you didn’t have anyone to spoil?

  “So, what’s the plan for today?” Olivia asked. Jeremy shut down his computer and put it in his briefcase on the floor.

  “I have to go back to the city in about an hour. I figured I drop you off then. Olivia nodded.

  “Okay, that gives me plenty of time to get ready. I have a lot of clothes to pack,” she smiled. Jeremy laughed.

  “Actually, my staff will take care of that for you. This will give us more time together this morning.” Olivia smiled broadly and seemed to relax. Jeremy was too perceptive to let that go.

  “You seem relieved,” he said. Olivia smiled and bit her lip sheepishly.

  “I guess I was feeling confused about why you didn’t sleep in the same bed with me. I worried that maybe you weren’t really interested in me, but then when I came down stairs-,” she paused as she fidgeted nervously with the hem of her blouse. “When I came in just now, you were really welcoming, which was reassuring to me.” Olivia laughed nervously. “I’m not usually this neurotic; I guess that was making me a little insecure about how you felt about me, and then it occurred to me-,” she paused, taking a sip of coffee.

  “What occurred to you?” Jeremy asked, his tone cool.

  “That when we both signed up for the dating service, we were each looking to satisfy sexual urges. I didn’t really think about getting into a relationship. I realized you might not have been, either. I guess, I’m just wondering where we stand.”

  Jeremy stared at the table for a moment, contemplating his response. He decided it was time to play his cards, and lay everything on the table. She might bow out, but at least he’d know early and move on before anyone got hurt. He planted his elbows on the table and rested his fist under his chin, staring directly into Olivia’s questioning eyes. She deserved the truth, and deserved to know exactly what he wanted from her.

  “Olivia, you’re right. I wasn’t looking for a relationship, I was looking for a sexual match.” Suddenly, Jeremy felt restless. He sat back and raked his fingers through his hair and then paused, staring at her. “I was looking for this.” He reached down and pulled out a document from a folder in his briefcase. He slid it across the table to her. He had been debating all weekend whether or not to show it to Olivia.

  “What’s this?” she asked.

  “A contract.” Olivia looked confused.

  “A contract, what for?” she asked, still confused.

  “It isn’t a legal contract, per se. It’s an agreement, between you and me, that defines the terms of our relationship. It is not uncommon for dominants and their submissive partners to sign these types of agreements because it clearly labels the roles and expectations of both parties in the relationship.” Jeremy watched Olivia closely, searching for her reaction. She listened to him quietly, without much emotion. Then she scanned the document.

  “Jeremy, this details how I’ll dress, what undergarments I’ll wear-,” her eyes grew wide, “or not, and even how I’m supposed to groom myself down there.” She said, sounding alarmed. She set the document down on the table and crossed her arms. Jeremy could tell she was troubled, but he wasn’t going to give up yet.

  “I know, it’s a lot. You see, when I signed up for the dating service, I was ultimately hoping to find someone to enter into an agreement such as this. It requires unwavering loyalty and commitment, and it extends the dominant submissive partnership beyond the bedroom.

  “You mean like a full time job?” Olivia looked up from her reading. Jeremy shook his head.

  “More like a role. You would be my submissive, completely available and compliant to me at all times, except of course, when you are at work or are attending other pre-arranged social obligations.

  He sat back and let her continue reading. He knew he might lose her in this moment. It was what he wanted though, and if she wanted to be with him she had to sign it.

  “What if I say ‘no?’” she asked.

  If you sign the contract, you are agreeing to not say ‘no’ to me, ever. You still have the safe word, or course, and you can use that at any time, you just have to remember- that comes with a consequence.

  “What if I say ‘no’ to signing the contract?” she asked.

  Jeremy sighed, his face resolute. “Then we’re done here.” He knew his words were harsh, but they were true. He had waited to present this to Olivia until he had a glimpse of what she was capable of handling. Now that he had, he was confident she would be an excellent candidate to fill the role of submissive he had been searching for. He realized springing the contract on her might be heavy handed, but that’s how he operated. It never benefited anyone to go easy on them, at least that was what Jeremy thought.

  “Olivia, I’m looking for a full-time submissive. Not someone to play with occasionally. It’s intense, but I promise to do everything to make it a profoundly rewarding experience for you. I will demand everything from you, but your satisfaction is my ultimate responsibility, and I take that job very seriously. It is why I want to dominate- so that I can control your pleasure, push you through your limits to heights of bliss you didn’t know were possible.”

  “I guess I’m still confused. Do you care about me? Are we in a real relationship, or is this just sex?”

  Jeremy looked deeply into Olivia’s eyes. He could see the concern on her face, and the need for reassurance. “Of course I care about you, and it is a real relationship. It is just one that happens to have strictly outlined parameters.” Olivia turned back to the document.

  “How long will the agreement last?” she asked.
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  “Three months.”

  “Why three months? Why not one month or six months or a year?”

  “Three months.”

  Olivia swallowed hard and looked back at the paper, her brow furrowed in thought. Jeremy sat back, and let her consider her response. He had made his best effort, and now it was time to let her decide. He had been in enough business deal to know not to get too attached to any outcome, but he had to admit, he’d be disappointed if she turned him down.

  Jeremy sat back and patiently waited for her decision. He watched, as her eyes traveled over the contract, reading and re-reading the details of the document. He was glad to see she was being so thorough. Finally, she looked up at him, her eyes wide with concern. “Jeremy, I want to…but I’m afraid.” Jeremy took her hand and looked deeply into her eyes.

  “Olivia, nothing in life is without risk. I have found that most things worth pursuing are scary.” He knew he was pushing her, but he believed it was the right move. She needed to be challenged, he could sense it.

  “So, Olivia, you have a choice, so what’s it going to be?” Olivia continued to stare expressionless at the contract. Jeremy thought it must be over. Despite his effort to remain detached, his heart sank. He sighed in defeat.

  “Okay,” he said, and pushed back from the chair. Just as he was about to stand up, Olivia raised her hand off the table and reached, shaking, for the pen. Jeremy turned and stared in disbelief. She was doing it. Olivia signed the document. Coiled tension instantly released and Jeremy exhaled loudly. He stood up and pulled Olivia up into an embrace.

  “You made a brave choice,” he said. She smiled weakly.

  “Brave or stupid, I’m not sure which yet.”

  Chapter 18

  By the end of the hour they were on the helicopter headed back to the city. Olivia had been quiet most of the flight, Jeremy assumed because she was processing the implications of the agreement she had signed. As they reached the outskirts of the city, her phone buzzed. Olivia glanced at the display and swore softly under her breath.