Shades of Step Billionaire

by Harlow, Jenna

  “I can see you’re at your edge. Just hang on a bit more, Olivia. I promise the wait will be worth it. His voice seemed to be receding, but she couldn’t tell in what direction he had moved. She was glad, she needed the break to pull herself back from the edge. In the distance, she heard a drawer open and shut. She listened for other noises, like chains rattling or more buzzing, but heard nothing. Straining to hear, she finally detected footsteps as he came back, causing tingles to dance over her skin.

  Jeremy returned shortly and was behind her again. One hand stroked and squeezed her ass, while the other slid along the length of her wet hot sex. Just as Olivia wondered if he was going to use the finger vibrator on her again, he pressed something large and firm at her opening. At first she thought it might be his cock, but she realized he wasn’t in the right position for that.

  “This will feel tight Olivia, stay relaxed,” he said. She felt pressure against her skin as he started to push the item into her. She wondered what it could be: another vibrator, a dildo, something weird like a cucumber or a banana? Whatever it was it was incredibly large. Much larger than any cock she’d ever had. He twisted it left then right and jostled it in slowly, sliding it into her wet pussy. Olivia held her breath as her skin stretched impossibly wide to allow for the girth of what he was pushing into her. Jeremy moved it in slowly, giving time for her to adjust as he went.

  As the item entered her body, Olivia felt she was being stretched to her limit. He had pushed and pushed until it was so deep into her, she worried he was going too far. It was almost painful. Almost. There was discomfort, like pain, but there was also pleasure. As he came to a stop she took a breath and willed herself to relax further. She realized her cunt, stretched to its limit, was throbbing around a giant dildo, and she wanted more. Olivia strained against her restraints as she contorted her body further to try and take it deeper into her.

  A slight moan escaped from her as he began to pull it out. She stiffened, remembering he had told her to be quiet. She feared he would punish her by stopping. If he paused, even for a moment, she thought she’d go insane. Jeremy must have noticed. He laughed from behind her. “Don’t worry, Olivia. You may go ahead and make noise now, I won’t punish you. You can even move, if you can.” As he spoke he pushed the dildo back into her.

  “Oh, thank god,” she groaned. She desperately wanted to squirm and groan as he moved the dildo in and out in a rhythmic motion. His movements were perfectly smooth and fluid. As tingling heat radiated out from her core, he once again pressed the vibrator up against her clit. He pressed his entire hand, along with the vibrator against her hot sex as the giant dildo continued to slide in and out of her. Olivia bucked and arched her back and moaned again, louder time, into the mattress. “Oh, fuck that feels good,” she said.

  “Oh, you like to swear when you’re turned on?” Jeremy asked in a teasing voice. “Tell me how much you want me to fuck you with this,” he said. He increased the speed of his motion, pushing the dildo in and out faster and faster. The burning need grew more and more urgent for Olivia. Jeremy kept pace with her escalating desire and hammered the dildo in with an almost frantic pace. “Oh fuck, Jeremy. Fuck me as hard as you can!” She was hanging on but knew she wouldn’t last much longer, she was too close, too needy to wait. “Olivia, come…” he paused and continued to pound into her. She felt the orgasm coming at her like a freight train. She wouldn’t be able to stop it. “…now!” her ordered, his tone loud and commanding. She hollered as an explosion of sensation detonated within her. It was as if every nerve ending fired at once; sending wave after wave of throbbing pleasure rushing through her. She had never experienced such a powerful climax; it seemed to shake her entire body. He continued to pump into her as her body was rocked by a torrent of spasms and slowed his pace as she came down, maintaining a steady pace until she had completely stopped shuddering on the bed.

  As her body became still, he pulled the enormous dildo out. Olivia, spent and tired, rested, panting into the mattress. She was barely aware of his movements as he unfastened the straps on her arms and legs. Once free, she spread out on the bed, her muscles relaxed. Jeremy wiped off the dildo and vibrator to their drawers in the apothecary chest and clipped the leather straps back onto the wall. He came back to Olivia who was lying on her stomach and softly caressed her back.

  “How was it?” he asked.

  “Mmm,” was all she could get out. She turned to look up at him and noticed a large bulge in his pants. A pang of guilt hit her as she realized she had barely laid a finger on him. Reacting quickly, she pulled herself up onto her knees and reached out for Jeremy’s belt.

  “Let me take care of that,” she said.

  “No,” he smiled. “Part of the excitement for me is the anticipation. I want to make myself wait a bit more before I let myself have you.” Olivia blinked her eyes down again to the lump in his pants.

  “Isn’t that uncomfortable?” she asked.

  Jeremy smiled. “Very.”

  Chapter 15

  Jeremy escorted Olivia back to his main bedroom. She showered in his master bathroom while he went to speak to his butler. The room was amazing. Gleaming marble floors sparkled beneath elegant cream cabinetry topped with gorgeous granite counter tops. Olivia guessed the shower could hold at least eight people and sprayed water from an assortment of spigots located on three different walls. She reveled in the luxury, and wondered what it must be like to live this way every day. Jeremy returned as she was toweling off.

  “Here,” he said, handing her a plush white terry cloth robe. Olivia took the robe and wrapped herself in it. She noticed it was a woman’s size medium.

  “Do you keep different size robes here for all your women, or do you pick women who are all the same size?” she teased.

  Jeremy smiled. “You are the first woman I’ve ever invited here. I was saving it for someone special.” Olivia locked eyes with him, checking to see if he was joking. Surely he must have brought someone here before her, but his eyes were serious. A flutter ran through her. She truly felt honored by him in that moment.

  “Thank you,” she said. Jeremy lifted her hand and kissed it lightly.

  “My pleasure,” he said. Olivia yawned and tightened her robe. It was late now and she was just becoming aware of how fatigued she was. She glanced around for her clothes, uncertain what to expect next. “Are you planning on taking me home tonight? Should I get dressed?” she asked.

  “No. Definitely do not get dressed,” he said, pulling her in close. He gave her a long leisurely kiss. Why don’t you stay the night? You must be exhausted,” he said, motioning over to the bed. The linens had been turned down, making it look irresistibly inviting. She yawned again. “Okay, you don’t have to ask me twice,” she said as she walked over to the bed. She crawled into the king size bed, marveling at the size. The bed was an identical replica of the one in his secret room. Four large hand carved posts stood on each of the four corners of the bed and held up a wooden canopy. Tailored silk curtains were tied back to each of the four bed posts, made to out of the same beige silk that adorned the rest of the bed. The sheets themselves were a high thread count Egyptian cotton. They were softer than any linen she had ever felt before. She started to lie back on the bed but then scrambled to sit up as she noticed Jeremy was unrolling his sleeves and buttoning the cuffs.

  “Aren’t you coming to bed?” she asked. Still buttoning his cuff, he walked over to her and sat down next to her on the bed.

  “No. I have some work to do,” he leaned forward and kissed her lightly and then stroked her cheek with his fingertips. “I’ll be in later.”

  “Oh, okay,” Olivia said. She couldn’t help but feel a little disappointed. She wanted fall asleep in his arms. The thought of going to bed in the large room without him seemed kind of lonely. She watched as he crossed the room, his tailored pants and crisp white shirt looked impeccable, there wasn’t even the slightest wrinkle in his clothes to indicate he had done anything other than work al
l day. She sighed as she let her head fall onto the pillow and tried not to over-analyze Jeremy’s absence. It did make sense that he would still have work to do. Anyone as successful as Jeremy probably always had something to attend to. She just figured after this amazing night it seemed rather anti-climactic to be left alone in his room to fall asleep. Still, she didn’t want to complain, or seem clingy so she snuggled down into the covers and instead focused on the amazing feel of the soft bedding she was laying on.

  Light cracked through the curtains and woke Olivia up the next morning. She rubbed her eyes as she sat up, at first wondering where the hell she was. In an instant, scenes from the evening before replayed in her mind, like a movie in fast forward: the bar with Claire, Trent in the alley, Jeremy rescuing her and taking him to his country estate, dinner, and then. Oh, my. She blushed, remembering the secret room. As her brain engaged again, she suddenly thought to look for Jeremy. A sense of disappointment washed over her as she turned and saw she was alone in bed, just as she had been when she fell asleep. In fact, the half of the bed Jeremy should have slept on looked undisturbed, making her wonder if he awoke early, or worse, never even slept with her at all. She wondered where he was, and why he didn’t sleep with her. A sinking feeling came over her that tainted her good mood.

  She got up and looked for her clothes from the night before. She had left them folded on an arm chair in the corner of the room. She wasn’t too excited about wearing them again, but she didn’t have any alternative. First she pulled open the curtains to get more light into the room. Sun spilled into the space, she squinted against the glare. Outside she could see an expanse of manicured lawn and ornate gardens. She wondered if Jeremy would have time to give her a tour today. Turning to the chair, she was surprised to see a stack of white boxes sitting where her clothes had been. A note was on top.

  Olivia-

  I took the liberty of replacing your blouse. I also ordered clothes for you to wear today. I sent the items you wore yesterday to be cleared.

  -Jeremy

  Curious, Olivia pulled the lid off the first box and peered inside. It held a travel sized makeup bag filled with high end makeup and toiletries. It even included a hairbrush and manicure set. She couldn’t believe it. Everything she would want was in that bag. A rush of excitement swept through her and she reached for the second box. Peeling back the white tissue paper, she pulled out a white blouse. It was the same style as the one Trent had ruined, but the cut and feel was completely different. The quality of the design, the stitching, even the fabric was much more refined than hers. She moved onto the next box. It contained an entire outfit: a designer pair of slim lined denim jeans, a light weight beige scoop neck sweater and a matching infinity scarf. The outfit was perfectly coordinated; she wondered if a professional stylist picked it out. At the bottom of the box were coordinating underwear; a beige lace thong and matching bra. She was familiar with the brands only seeing them in high fashion magazines. She never dreamed she would wear anything that high end. Each item was exquisite. Olivia flipped over a few tags. Sure enough, the items cost at least four times what she normally paid for her own clothes. She gasped as she realized the clothes would have paid months of her rent.

  A rush of excitement ran through her. She couldn’t wait to try everything on. She quickly slipped into the new outfit and then rushed to view herself in the mirror; the clothes fit like a dream. Casual, yet very elegant, she felt like one of those women who have their pictures snapped and appear in glamorous magazines as examples of street chic. As she headed for the door, she noticed another box on the floor by the chair. Her heart raced and she rushed over to it. She laughed, opening it. Shoes, of course! The box held a pair of beautiful leather flats that matched the outfit perfectly. Jeremy had thought of everything. She found the thoughtful gesture reassuring, and realized it took the sting out of the fact that he didn’t sleep in his bed with her last night. As she put the shoes on, she wondered when he arranged for all this.

  Olivia made her way down the stairs and headed for the dining room. She wasn’t sure where he would be, and didn’t feel comfortable enough to wander around alone, so she headed to the one room she was familiar with. Luckily, Jeremy’s butler approached just as she entered the room.

  “Good morning, Miss. Mr. Hamilton is in the sun room off the kitchen. You’ll find him through that door,” he said, pointing toward the door at the end of the dining room. Olivia smiled and nodded.

  “Thank you,” she said and headed through the door. Once in the kitchen, Olivia was taken back by the gleaming stainless steel appliances, sparkling granite counters and gorgeous cream cabinets. It was a beautiful room. Beyond the kitchen itself, she saw a small dining room surrounded by beautiful windows. Jeremy was sitting at the table working on his laptop. He looked up and smiled as Olivia entered the room. As his eyes locked onto her and she saw his welcoming expression, a wave of relief washed over her. She realized in that moment, she had been nervous to see him. Perhaps in the back of her mind she had worried that he would have regrets about the night before. Her concern evaporated the minute she saw him. He stood up and kissed her cheek as she approached the table.

  “Good morning, Olivia. Please, sit,” he said, motioning to an empty chair. A shiver ran through her as she caught sight of him. He smiled and his teeth sparkled in the light, highlighted by a single dimple on the edge of his cheek. He’s perfect. Olivia approached the table. She felt a flush burn her cheeks as she took a seat near him. It was a cozy room. Sunlight filtered in through the large windows and provided a view of the patio outside. “Would you like something to eat?” he asked. Before she could answer, Jeremy’s butler appeared again and sat down a plate of eggs and fresh asparagus. It looked like beautiful.

  “Yes, thank you,” she said. The eggs looked divine, and sure beat her usual breakfast of a yogurt and power bar.

  Jeremy poured her a cup of orange juice from a carafe on the table. “Your outfit seems to fit nicely,” he said, a smile curled around the edges of his lips. Olivia looked down at her new clothes.

  “Oh, Jeremy, they’re beautiful. You didn’t have to do this; I could have worn my other clothes home, really.” Jeremy shrugged nonchalantly.

  “I know I didn’t have to. I wanted to,” he said. Olivia held his gaze for a moment, assessing his response. She was happy to see how sincere he was; it made her feel less guilty and self-conscious about the amount of money he had spent. Never in her life had anyone been so generous with her.

  “Oh, and before I forget-,” he said reaching for something on the chair next to him. “Here’s your purse. You left it in the dining room last night.” Olivia’s mouth fell open. She was never one to leave her purse behind.

  “Oh, right, thank you. I completely forgot about it,” she said. She must have been more distracted that she realized last night. She looked back at Jeremy, his dark eyes smoldered even in the morning light. She realized how easy it would be to be distracted around him. She took a bite of asparagus and moaned in delight. “Oh, my god that’s good,” she exclaimed. It was cooked to perfection and left a lingering taste of melted butter on her tongue. She couldn’t imagine eating this well every day. Jeremy smiled.

  “I’ll pass the compliments on to my chef,” he said. He has his own chef? Of course, he’s probably the one who cooked dinner for us last night. She was momentarily surprised by his statement. It was hard for her to wrap her head around how different his lifestyle was from hers. “That reminds me, I need to have a word with him before he leaves for the market. Would you excuse me for a moment, Olivia?”

  “Sure,” she said. Olivia’s phone buzzed from inside her purse just and Jeremy stood up.

  “I forgot to mention, you’re phone has been ringing all morning. Someone has been trying to contact you.” Jeremy disappeared into the kitchen as Olivia pulled out her phone, it was Claire. “Hi, Claire,” Olivia said.

  “Olivia! Oh my gosh, are you okay? I’ve been trying to call you! After you left the
bar, Trent go the shit beat out of him! The found him in the alley knocked out cold, can you believe it, a big guy like him? He had to get stiches and everything. He said a group of guys jumped him. Scary, huh?”

  Olivia rolled her eyes. It was just like Trent to make up a story to protect his ego. Olivia briefly considered telling Claire what really happened, but she still didn’t want to discuss it. Instead she kept it to herself. “Oh, is he okay?” she asked.

  “I’m not sure. Last I heard he was going to the hospital for stiches and maybe an x-ray.” Olivia thought about how she had left him the night before: knocked out cold on the hard pavement. A twinge of regret swept through her. No matter how awful he was to her, she still felt compassion for him, and wondered if he was okay.

  “Wow, I’m sorry to hear that. I can’t talk right now, Claire. Will you let me know if you hear anything else?”

  “Sure, call me later! I have to fill you in on my night with Vince, it was great! She yelled as she hung up the phone. Olivia laughed at that as she disconnected the call and then viewed her phone history from the night before. She had missed forty seven calls from Trent and her voicemail was full. Letting her sympathetic nature take over, she decided to listen to a few of the messages, just to confirm that he was alright. That was a mistake.

  11:00 “Olivia, are you alright?” Trent yelled into the phone. Olivia quickly pulled the phone away from her ear he was talking so loud. “ I hope you didn’t go anywhere with that maniac, you know he attacked me for no reason, right? I’m gonna need stitches. I’m gonna sue his ass.” Olivia rolled her eyes, it was just like Trent to revise history and deny any wrong doing. She deleted the message and moved on to the next one.