Windy City: The Complete 5 Book Series

by Measha Stone

  She continued to watch herself in the mirror as she undressed.

  The option of saying no to this step and leaving hadn’t stayed in her mind long. They had agreed to the terms of their relationship, and punishments came with the territory.

  He’d kept to their agreement; he didn’t try to maintain control when they were apart. In turn, she would stick to her part of the agreement.

  Royce’s entrance was signaled by the heavy shuffling of his feet along the carpeting. She still found herself in awe of his size. He hadn’t dressed yet for the day; his pajama bottoms added a lightness to the heaviness of the room. When she thought of a Dominant dishing out a spanking, she didn’t picture him wearing loose-fitted plaid pajama pants.

  A drawer scraped open. Metal jingled. She buried her face in the comforter.

  A heavy sigh—one full of disappointment—filled the room, and her heart sank. The bed gave way to his weight as he sat beside her. She didn’t chance looking at him; she didn’t want to lose her nerve.

  “I can’t take care of you if you won’t be honest about your feelings.” He placed a warm palm on the curve of her bare ass. “Part of playing is talking afterward to be sure you and I are okay, and no physical or emotional damage occurred. My intent may be to cause you temporary pain with a clothespin or a spanking, but it is never to injure you. When you won’t talk to me, how can I assess the situation? How can your needs be attended to?” He rubbed her skin.

  Not sure if she should speak, she decided against it. She peeked over her shoulder. He was watching his hand linger over her ass. His words made sense, but his talk about her needs threw her off-guard. No one in her past gave her the impression that her needs meant anything to them. She was still unsure how to handle this part of him.

  The first swat surprised her. She jumped at the impact and the sting of his bare hand. He had said it would be with his belt, but she wasn’t about to argue.

  “Warmup first. Then the belt.” He slapped her again. More mind reading.

  She grunted.

  He continued to bring his palm down heavily on her bottom, his fingers lingering a moment before he delivered the next smack sending tingles across the sensitive skin. She tried to concentrate on his words instead of the physical presence of his hand.

  Her lungs burned from the heat in the room, and her ass warmed at a steady pace with each lasting touch of his hand. She gripped the comforter as a hard slap landed on the tender down curve of her ass. Each slap resonated on her skin, creating a blanket of heat over her ass.

  He paused the spanking to stand and change positions. She clenched her eyes shut and willed her cunt to ignore the sensations he was causing. Her ass was on fire, but she could feel the wetness between her legs in response. Her mind did not share the arousal, but she had lost control of the physical elements of the situation.

  He unrolled the belt. “Are you ready?” His voice was tender.

  No! “Yes.” She kept her eyes focused on the bedding. Her fists crumpled the comforter with their grip. Every muscle tensed in anticipation of the first strike. Determination set in—she would get through this without complaint. He would deliver the punishment, and she would take it, but there would be no other interaction

  How wrong she was! The intensity of the burn shocked her; an electric shiver ran up from her ass through her spine. She stood upright and threw her hands behind her protectively and to rub away the flames.

  “Back over.” He sounded calm, as though this was all business. “Now, Jess.”

  She complied, swallowing hard and taking deep breaths. The surge of fire from the second lash spread over her before she registered the swish of the belt. With the third, a cry escaped her before she could contain it. She wanted to jump out of her skin. Any mental block she foolishly tried to put into place quickly dissipated with the lash of his belt.

  By the fifth strike, she yelled out, losing more of her resolve by the sixth. “I’m sorry!” She abandoned all earlier determination when the seventh strike crossed her ass with a hot-iron feel. “Please, Royce!”

  “Almost done, Jessica.” He laid the eighth and ninth strokes across the tops of her thighs in rapid succession, giving her brain no time to reconcile the first before the second landed. Tears burned her eyes and her cheeks as they fell. One more. She took a deep breath. Just one more.

  Her shoulders tensed, and her fingers ached from their tight grip on the bedding. She gulped and tried to ready herself for the last lash. She rested her forehead on the damp bed and readjusted her feet on the floor. Her legs shook from holding herself in the position with such intensity.

  “The last is always the worst,” he informed her, running his fingertips over her ass. Even his feathery touch caused more misery.

  She imagined what horror he must be seeing. Convinced her cheeks glowed a dark red, her mortification continued. Angry welts had to be popping up all over her ass. Positive she looked a ruined mess, her face heated.

  “Let me know when you’re ready.” He removed his fingers.

  She took another deep breath. To ask for the last one, it was too much.

  “I can wait.” His voice remained steady.

  Their wills warred against each other.

  Her mind raced. She braced herself and forced her voice into action. “Okay. I’m ready.”

  The belt crashed across both cheeks at the curve—too close to her thighs to count as a slap on the ass. She cried out and shook with tension then slowly allowed herself to relax.

  More tears spilled onto her cheeks, and she realized the whimpering filling the room came from her. A release valve had been triggered with the last lick of the belt. The tears wouldn’t be fought against; her emotions bubbled over until they couldn’t be suppressed any longer. Resting her face on the bed, she pulled her legs up and curled into a ball.

  He sat beside her and rested his hand on her back. He said nothing, but he remained. She lay on his bed blubbering like an idiot. Shouldn’t he be running from the room?

  After a few moments of quietly shedding tears, she unraveled herself and sat up. Concerned eyes met hers and she leaned into him, resting her face in the crook of his neck “I’m sorry.” She sniffled.

  He wrapped his arms around her, tucking her beneath his chin. “Me too. I really wanted to ravage you this morning.” His words only twisted her stomach further.

  She’d ruined what could have been a wonderfully sexy morning.

  “Another time.” He kissed the top of her head and rubbed his chin against her.

  “Do you still want me to answer your question?” Her voice was soft.

  “Yes. Would you like to get dressed first?” He stroked her bare shoulder.

  “No, it’s okay.” Being naked made being vulnerable to him somewhat easier. If she could handle this, him being able to see and touch her everywhere, letting him see what was beneath wouldn’t be so hard. So long as she didn’t have to look at him at the same time.

  He kissed her again and tightened his hold. “Are you ashamed of what we did—or that you enjoyed it?” She suddenly understood what witnesses at trial must feel like.

  “I don’t understand why I enjoyed it. I guess that’s the scary part. Not understanding your own feelings. I mean, the clamps hurt…but in a good way. Which makes no sense. The crop…same thing. It’s all messed up. Maybe I’m messed up.” She shrugged and wiped the tears from her cheek.

  He nudged her away with his shoulder and used his finger to raise her chin. His eyes deepened with sincerity. “You are not messed up.” His voice was firm. “I want you to do me a favor. I want you to open yourself to the possibility that you can find happiness in a relationship with another person.”

  “You are asking for a lot.” She tried to pull away, but he held her tightly with his fingers.

  “I know.” He kissed her nose. “Just allow yourself to feel without doubt or scrutiny.”

  “You are a terrifying man.” She screwed up her lips into a half smile.
r />   “Really?” Sarcasm seeped from his response.

  “Yes.” She pouted. He gave in to her request and placed his lips on hers.

  “No more hiding from me. I won’t give you a second chance again. The first time you hide, you’ll be punished.” He released her. “I’ll let you get dressed. I’d like to walk you home. I have a project for you, and it will take you most of the day to complete it.” He flashed a mischievous smile at her and pinched her bottom to get her moving.

  She giggled—a sound she had not made in a long time—and scooted from the bed. “I thought we agreed you wouldn’t invade my private bubble.” She shot him a worried glance as she worked her pants over her hips.

  “I’m going to nudge that boundary a little.” He found a clean shirt and pulled it over his head. “Don’t worry,” he stepped to her and gathered her in his arms, kissing her wrinkled brow, “I know you’ve had bad experiences with trust in the past, but you’re going to start learning to trust me.” He kissed her nose once more.

  She took a deep breath. “Okay.”

  He kissed her mouth. “Good girl.” He smiled against her lips and released her. “Now, let’s get you home.”

  A warm shiver ran through her with the words “good girl.” Two words striking a happy place in her core. She pushed her worry down for later evaluation and followed him from the room.

  Chapter 8

  The walk to Jessica’s apartment gave Royce time to contemplate the new relationship. New relationships didn’t scare him; he’d had plenty over the past several years. They were all fun at first then sagged a bit in the middle before dying a slow, pitiful death at the end. Jessica threatened to be different.

  It wasn’t the thrill of training her to be his submissive or the excitement of new love that kept him wanting her. It was the way warmth would spread through his veins at the sight of her, the smell of her, the sound of her voice. Even her “hello” on the phone made his heart race. These feelings put him in new territory.

  The tight hold she kept on herself slowly loosened. When he held her in his arms, the tension eased, her guard lowered. He loved the suppressed smiles slipping out, the moments she took before speaking. Impulsiveness didn’t rule her, she ruled it. She could be spontaneous if he pushed her, but she wouldn’t instigate. She was in control of every aspect of her life, but she softened with him, and he could feel the tension leave her. Her eyelids would instinctively drop, and a blush would creep onto her cheeks.

  Her submission was natural, even though she was only beginning to understand it. He found himself already attached to her; there would be no sag in this relationship. He forbade it. Potential for a lifetime of adventures lurked beneath their casual teasing and erotic touches.

  Punishments happened in his relationships. This was a fact. Submissives would eventually earn them because they were human. He knew she wasn’t different in that way. He had worried she would be more argumentative about having earned her first one. But she’d surprised him. She’d opened up to him—trusted him to lead her through the unknown and deliver her safely on the other side.

  A thick wall encased her heart. He could feel it in the way she tensed after a smile or looked away when they locked eyes for too long. She’d been hurt more than once, but he would be patient, and the walls would come down. He wanted to be her knight on a white horse, carrying a single tail and handcuffs.

  The idea of someone holding her in their arms and hurting her angered him. Anyone with a few live brain cells could see how fragile she really was under her thick exterior. She played tough, and her bravado kept the idiots at bay, but he was no idiot. Beneath her solid shell was a soft, loving woman. His loving woman. Once he cracked the wall, the rest would crumble.

  Once again, he found Jessica standing on her steps, waiting for him. At least she remembered a scarf and a pair of gloves. He wasn’t sure what she didn’t want him to see in her apartment, but curiosity was beginning to gnaw at him. She gave a cautious smile and stepped down from her stoop. “Hi.”

  “Hey there. Hope you weren’t standing out here long.” The red tinge at the tip of her nose confirmed she had been.

  “A few minutes.” Not a complete lie, but it bordered.

  “Uh-huh.” He raised an eyebrow and leaned down to give her a warm kiss. A gentle blush covered her cheeks, either from the chill or the knowledge she teetered on the line of dishonesty. “I’m thinking Italian.” He slid his gloved hand into hers and led them down the street. “It’s only a few blocks. If you aren’t too cold, we can walk.”

  “I’m fine.” She nodded. The usual tension in her hand loosened as they walked. He probed her for information on her day, and she talked freely about the case she was working. Her boss annoyed her to no end and Royce felt the need to find the ass of an attorney she worked for and have a little chat with the bastard.

  When he signaled the entryway to the restaurant, she pulled them to a stop, looking down the street, then at him. “We are only two streets from your apartment,” she stated with wide eyes. “I should have met you there instead of you coming all the way around to mine and backtracking.”

  “No, you shouldn’t have,” he said, opening the door and ushering her inside. He gave his name to the hostess, and they were escorted to a quiet table in the corner.

  “Why?” Jessica asked once the menus were handed out and the water poured.

  “Why what?” Royce questioned. “Do you want some wine?”

  “Why shouldn’t I have met you? It would have made more sense.” Royce glanced over his menu. Innocent confusion lingered in her eyes.

  “You shouldn’t have met me at my place because I didn’t want you to. I wanted you to wait at your apartment—inside—for me to pick you up so I could walk you to dinner.” He placed the menu on the table and folded his hands on top of it. “The efficiency of how we arrived here had nothing to do with it. If I wanted you to meet me, I would have told you. Which I’ll never do, by the way. I’ll always pick you up, and, hopefully, someday soon, you’ll let me do so at your front door.” He gave her a grin, then picked his menu up again. He already knew what he would order, but he wanted to give her a moment to process what he’d said.

  After several moments of silence, she tossed her menu onto the plate and announced she would have the gnocchi. He grinned at her over his menu. The little bit of assertiveness in her tone didn’t alarm him. She was allowing him to decide how they traveled, but she was still independent. She was not as complicated as she thought. Or maybe he saw through her more easily than others had.

  They enjoyed their meal. When the waiter asked Jessica if she wanted a second glass of wine, she had given Royce—who had shaken his head—a quick glance. When she declined the glass, he reached over and gave her hand a squeeze. “Such a good girl tonight,” he mused with a grin, thinking of all the naughty things he wanted to do with her.

  Her smile made him want her all the more. Small chips, he reminded himself. Little nicks in her wall. She didn’t pull her hand away. Instead she ran her thumb over his and widened her smile. They would be skipping dessert.

  Royce gained the attention of their waitress and handed over his credit card. He didn’t ask for the check, he merely wanted to pay and leave. He wanted to get her home while she continued to be so accommodating. There was another lesson to give in pleasurable pain, and the sooner they got back to his apartment, the sooner the lesson could begin.

  As they made their way out the door, Jessica bumped into someone. “Oomph. Oh. I’m sorry,” she apologized, and Royce turned.

  “James.” She said the name in a mere whisper but filled with raw emotion. Her face paled but her chin thrust upward. He followed her gaze to a man standing directly in front of her. Tall, not as tall as Royce, but taller than her. His shaggy blonde hair was haphazardly combed, and he tossed his head to the side to clear it from his eyes. Eyes sizing Jessica up before giving her a satisfied grin.

  “Jessica.” Royce stiffened at the sound of her na
me sliding off James’s tongue. Royce slid his hand back into Jessica’s hand and gave her a supportive squeeze. Not knowing the full story of what was going on, he could tell this man upset her. And he wouldn’t allow that.

  “Jess?” Royce stepped to her side.

  He felt a shiver run through her as she turned away from James and looked up at Royce. “Royce, this is James—my ex. James, this is Royce.” The difference in tone between the two names couldn’t be missed, and James turned to Royce, giving him a once over. Royce didn’t reciprocate. He didn’t need to. He knew everything he needed to know from the simple fact Jessica was on his arm, and not James’s.

  “Nice to meet you. Uh, this is Helen.” James turned and groaned when he noticed his date had wandered off. “She was just here—oh, here she is.” A prettily made-up blonde slid to his side holding a glass of wine.

  “They said there was a wait since we didn’t have a reservation, so I went to the bar.” Her high, nasally voice grated on Royce. This tone always made him cringe.

  “Nice to meet you.” Royce smiled down at the woman, who looked completely oblivious to the rising tension.

  “No Veronica?” Jessica asked with forced civility. Royce gave her hand a firmer squeeze. A scene wouldn’t help her with her discomfort.

  “No. Uh. She didn’t really work out.” Whatever awkwardness Jessica felt, doubled in James’s expression when she asked about an obvious ex. Helen looked to James with questions, but he ignored her. “Look, I know we didn’t, I mean—” His worried glance swung up to Royce who raised an eyebrow in response.

  “It was nothing,” Jessica flat-out lied. Royce could feel the trembling in her hand, the stiffness of her spine, and her breathing deepen. Whatever it was, wasn’t nothing.

  “Jess, we should be going. I’m sure James and Helen will be getting a table soon, although without a reservation on a Saturday, it’s a pretty long wait.” Royce tucked Jessica’s hand in the crook of his elbow and escorted her through the front door, effectively dismissing James and his date.