WINDY CITY: The complete series

by Stone, Measha

  “I’m sorry.” His eyes softened. “We have talked about that,” she continued in a soft tone. Even with his fingers tangled in her hair, she had no fear of him.

  “That’s better.” He loosened his grip, but didn’t release her. “Now, what was it you wanted?”

  She stared at him for a moment. The words were there, ready to be spoken, but something continued to hold her back. It was one thing to act out dirty things because he told her to; it was another to declare she wanted them to happen.

  “There is nothing you can say that will make me think less of you or want you any less.” His words stroked her.

  “It feels silly now. I’ve ruined the moment.” She took a strained breath. “I wanted to suck you.” The weight of a boulder lifted from her chest as the words fell from her lips. She searched his face for a reaction. How big of a fool had she made of herself?

  He was grinning at her as if he’d been given a winning lottery ticket.

  “The moment for that can never be ruined,” he promised, then let go of her hair to caress her cheek. He helped her from the stool and gave her room to glide down to her knees.

  She looked up at him with wide eyes, her tongue running over her lips in anticipation. Her stomach fluttered at the idea of what she’d said, what she was doing, and how much she was enjoying herself. Never before had she asked to do such a thing. She was no prude, she’d done this many times with past lovers, but they had always been the one asking, not her. But like so many things with Royce, this activity had a different feel. The desire to please him, to give him the pleasure he’d given her, overruled her sense of propriety. Kneeling before him as he reached for his belt didn’t give her the sensation of subservience as she’d once worried. No, it felt—natural. As though nowhere else would be as comfortable as right where she was. On her knees. At his feet.

  She watched as his fingers moved over his belt, pulling the thick black leather through the buckle. He unbuttoned and unzipped his jeans, pulling himself free of his clothing. He touched the top of her head with his fingertips, and she didn’t need any further encouragement.

  She wrapped her fingers around his thick shaft and brought him to her mouth, using the end of her tongue to lick the bead of moisture from the tip of his head. Gazing up at him, to make sure he was watching; she noticed his breath quicken. With a devils’ grin she took him fully into her mouth. She sucked him down her throat then pulled back, bobbing over his cock while cupping his balls. He growled, sending her arousal soaring.

  “Wait, wait.” He pulled away from her, sounding pained.

  “What’s wrong?” She ran her tongue over her lips, relishing in the salty taste of him still lingering there. Had she been too forward?

  “Let’s go to the couch.” He helped her stand and threw her over his shoulder. His strength surprised her.

  He placed her on the couch as though setting down a precious artifact. She watched in silence as he removed the rest of his clothing and sat beside her.

  Pulling her to him, he kissed her deeply. She waited for him to break off the kiss, as he always did, and then she slid down to his lap.

  Jessica stretched out on the couch beside him. He ran his fingers through her hair and pulled it back, holding it in his hands as he guided her down his shaft. Resting her hands on his thigh, she gave control to him, letting him choose the depth and speed of the strokes. Her soft moans resulted in a low growl from him. Enjoying the pleasure is caused, she moaned again and heard him suck in his breath.

  “You’re killing me!” He groaned and pulled her from his lap. As he watched her wipe her mouth with the back of her hand, he took a ragged breath. “Reach into my back pocket.” He pointed to his jeans.

  She reached down and dug around until she found what he was looking for. She handed him the small foil package.

  “Put it on.” He commanded as he pushed the condom at her.

  She opened the condom and placed it over the head. With slow deliberate movements, she rolled the condom down his shaft, enjoying the long hiss he released as she reached the base of his dick.

  Once finished, she sat up and gave him a cocky grin. Something about him gave her the nerve to be daring, to do things she’d dreamt of but never tried before.

  He pulled her to him and kissed her again with a new fire. Without breaking free from the kiss, he brought her up to straddle him.

  She needed no instruction. She guided him into her and groaned into his mouth with the full sensation he caused. Stilling her movements once she was fully seated to adjust, she then rocked her hips, rubbing her clit against his pelvic bone. His hands remained on her hips while she ground into him, and he licked her nipple. A long, tongue-dragging lick.

  Up and down on his shaft, she rode him hard, searching for the fulfillment only he could give her. He threw his head back, and she kissed his neck, sucking gently before he yanked her away by her hair. The pain came quickly, but the look in his eyes soothed it away.

  “Ask before you come,” he directed her.

  Instinct made her want to disagree, to declare her freedom…but the tingling inside her at his instruction hushed her brain.

  His eyes warmed at her agreement, and the tingling intensified. A dark storm swirled. His pleasure drove her own deeper. She didn’t understand the mixture of the emotions rattling through her.

  She continued to bounce up and down on him. He captured both her nipples in his hands and began twisting them with gentle pressure. The bite ignited her, stripping away the last bit of hesitation. Her breasts were still sensitive from the crop and clothespins; his slight touch drove her to the edge.

  “Can I?” She dug her nails into his skin.

  “Can you what?”

  “Can I come?” she growled.

  He laughed. “I’m sure you can. I’ve seen it.”

  Her nails dug deeper into his shoulders, her frustration building.

  He released one nipple and reached between their mingled bodies, flicking her clit as she continued to ride him.

  “May I come!?” She panted and ground her hips into him harder, her eyes rolling back from the pleasure. She teetered at the brink and wouldn’t last much longer.

  “Yes, you may,” he called out and found his own release as she bucked against him with all the eagerness of a predator. She screamed out her orgasm. His chest vibrated against her as he roared out his orgasm. Clutching to each other they moved in unison as their orgasms tore through them, each lending strength to the other until they fell limp with exhaustion.

  When the waves passed, she fell onto his chest, her head resting in the crook of his neck. They panted and wrapped their arms around each other.

  Beneath her cheek, his heart beat strong and steady—just like him.

  “Jess?” Royce searched her face. “You okay?” He wiped a strand of hair from her eyes.

  “Yes,” she answered and moved from his lap.

  He sighed. “You don’t have to talk about it yet if you don’t want to, but don’t lie to me. One more, and you’ll have your first punishment.” He leaned over and kissed her forehead. “Are your breasts sore?” He turned to examine her.

  “No, I mean, yeah, a little, but not bad.”

  “You did extremely well.” His dimple appeared again.

  “Thanks?” She’d never been complimented after sex before and wasn’t entirely sure how to respond.

  “I want to ask you something, and I’d like your honesty.” He pulled away from her and held her chin in his fingers.

  She searched his face for a hint at what he was about to bring up. “Okay. I’ll try.” She took a deep breath and waited.

  “Why did you become a paralegal instead of going into publishing? There has to be a reason.”

  She wanted to pull away from him, to ignore the question. Feelings didn’t work well for her and trying to talk about them only made it worse.

  “It just wasn’t for me,” she said, avoiding his gaze and focusing on his chin.

&n
bsp; “Why?” He pulled her chin upward until she put her eyes back on his.

  “I was afraid,” she said in a soft voice.

  He wrinkled his brow.

  “I would have failed,” she clarified.

  “So, you didn’t try?” he asked in a firmer tone.

  Did she hear disappointment? “It was a really bad senior year. When it was over, I needed a job to pay the rent. The paralegal job came along, I wasn’t horrible at it, so I stuck with it.” She shrugged.

  “What happened senior year?” He asked, releasing her chin.

  She shook her head and forced a laugh. “Nope. One question asked and one question answered.” She leaned into him and brushed her lips across his, giving him her best come get me look. It was his turn to laugh and shake his head.

  “Fair enough,” he said after a long pause. “I want a shower. Come help me get cleaned up.” He stood from the couch and offered his hand.

  She accepted and let him pull her toward the bathroom.

  They showered together in silence, taking turns washing each other. He insisted on shampooing her hair for her, taking his time with the chore. She relished in the moment. Being taken care of didn’t happen to her very often, and it wouldn’t last forever.

  Once they were cleaned up, they slipped into bed. She knew she should get dressed and go home, but he snuggled her close, and unfamiliar contentment crept up her spine and settled in her mind.

  She would allow herself one night, and one night only.

  Chapter 6

  Royce’s eyes fluttered open from the sunlight streaking across his face. Realizing it was Saturday, and he didn’t have to go into the office, he grabbed the pillow beside him and covered his face. Then he reached out beside him, and cool sheets greeted him. He tossed the pillow aside and sat up.

  No Jessica. The clock told him it was only seven in the morning. Maybe she was an early riser. He tried to give her the benefit of the doubt.

  He knew there was more to her past than a few bad love affairs. She’d been hurt somewhere deep within her causing her to guard herself in such a way. He’d taken a risk pushing her about her career, and she hadn’t disappointed him. Perhaps the residual feelings from sex had loosened her tongue. He decided to try again for more information right after her next orgasm…right after breakfast.

  Jessica’s beauty captivated him, but her personality gave her a glow. Any woman could put on makeup and make herself pretty, but Jessica didn’t need to do anything. She gave him the vibe of loyalty and honesty. She may have told little lies to hide her emotions from him and anyone else taking the time to peek in, but at her core, she was an honest person. She worried about the people in the case she was working on. The asshole she worked for couldn’t care less about them, but Jessica took it personally. She wanted the best for them; even if was out of her hands.

  He’d worried about driving her too hard with their game the night before. Her eagerness and willingness were as much of a turn on as her beautiful breasts. The pins he’d chosen for their play gave the lightest pinch, though he wondered if she would have been open to taking the harder ones. She’d surprised him with her boldness with asking to suck him off and then topped it off with the condom. Thinking about it woke his dick up.

  He jumped out of bed to find her.

  She sat in the living room, fully clothed, fondling the riding crop.

  He paused in the doorway to drink her in. Her braid fell down her back, and she wore the same clothes as the night before. He made a mental note to ask her to bring a bag next time, or he would shop for her. Once he got her out of her clothes, he’d check her sizes.

  She balanced the rod on her palms as if to check its weight, then brought the flapper to her nose and sniffed the leather. He watched her run it over her jaw and imagined himself performing the same act.

  She stood from the couch and put her foot on the coffee table, lightly tapping her jean-clad thigh with the flogger.

  “Good morning.” He stepped into the living room, stopping her experiment before he sprang through the thin fabric of his pajama pants. His presence startled her, and she fumbled with the crop before dropping it onto the coffee table.

  “Hi.” She stuffed her hands in her pockets, a rosy blush settling on her face.

  “I worried you ran away again.” He kissed her on the cheek and picked up the crop. “Are you curious about this?” He touched the flapper to her nose.

  She shook her head and stepped back.

  One of his eyebrows rose. “Did you hate it last night?” Had she rethought the scene after the arousal had worn off?

  “No,” she admitted, taking another step.

  “Are you ashamed you liked it?” He toyed with the crop.

  “No.” She shrugged, her eyes darting from the leather to the window behind him, seeking a safe place to mentally hide.

  “That’s one. I’ll give you one more chance to be honest with me.” His jaw tightened. “Are you ashamed of what we did last night?”

  “Not ashamed.” She scratched her elbow, her eyes on the coffee table.

  “Then what?” She had more lingering in that beautiful mind of hers, and he wanted it. He wanted to know everything about her—her feelings, her desires. If only he could get her to stop hiding from them.

  Her eyes fixed on the leather rod. “What we did was fine. I liked it.” Another shrug.

  “And that’s a bad thing.” He slapped the crop against his palm. The sound hung between them.

  “Stop putting words in my mouth,” she demanded with balled-up fists and a stomp of her right foot. Such defiance for such a simple question.

  He tilted his head and stared her down like the adversary she was making herself. “Do you think stomping and yelling is the way we should handle this?” His words didn’t hold curiosity, but rather a warning.

  “You keep insisting you know my feelings.”

  “You keep insisting you don’t have any,” he threw back. “Tell me, and I’ll stop assuming.” He crossed his arms over his chest, still holding the crop in his hand.

  “I don’t understand why I liked it. I shouldn’t have liked it.” She took a deep breath.

  “Tell me something, Jessica. When I instruct you and you obey, what does it feel like to you?” He leaned against the arm of the couch.

  Her eyelids drooped, her fists remaining tight, and she chewed her inner lip. “I was thinking we could have breakfast.” Her eyes moved again, still not falling on him.

  “That’s two. One more and you’ll get ten with my belt.” His tone was unyielding, his jaw tight. There was a shift in her stance; she was going to defy him, push him. He hoped he read her signals wrong. The chances of wrapping her legs around his waist and sinking his cock into her shrunk the longer she glared at him.

  “Your belt? One difference of opinion, and you reach for your belt?” She crossed her arms over her chest and faced him.

  “Stop fighting me. Answer the question, and we can go into the kitchen and have breakfast.” He blocked her attempt to derail the conversation.

  “See, now I really don’t want to talk about it.” She raised her chin in defiance.

  There would be no morning sex.

  “Jessica, go into the bedroom, remove your pants, and bend over the bed. Keep your hands in front of you.” His voice sounded flat, even to him. Most submissives in her position would show some remorse before quickly moving to obey him. But she wasn’t most submissives. Hell, she barely understood what it was to be a submissive.

  She didn’t move.

  “That would be now, Jessica. Go.” He nodded toward the bedroom, as fear flowed into her expression. “Go.” He held firm.

  “I don’t see—”

  “Let me put it this way. You have two choices.” He uncrossed his arms and squared his shoulders to her. “You either do as you’re told—like you agreed when we began this—or you leave. Punishments are part of the deal. You broke a rule. You’re holding back.” His heart pounded thr
ough his ears. What if she chose the second option and left him? Would he be able to keep from chasing her?

  “Fine. I’ll answer you.” She dropped her hands to her sides and relaxed her shoulders. Her eyes met his. She looked so hopeful, and he almost hated to squash it.

  “We’ll talk after your spanking. Now, go to the bedroom, or I’ll have to add more to your punishment.” He would not be moved from his decision; she would need to learn that about him. Once he decided on a punishment, consequences would be paid, and no amount of sweet talk would change it.

  Jessica’s gaze darted to the crop and back again to his eyes. Her thoughts flashed across her expressions.

  He continued to glare at her as she made her decision. Her heavy sigh, brimming with resolve, gave him his answer. He moved from her path. Their eyes never met as she walked past him and disappeared down the hallway.

  The morning of sultry meals and erotic moments dissipated before his eyes along with his hope of her first spanking being one of pleasure. He glanced at the crop in his hand and tossed it onto the coffee table.

  Resigned to the path they were now on, he crossed the living room and headed to the bedroom.

  Chapter 7

  Jessica stood next to Royce’s bed, looking at herself in the full-length mirror hanging on the closet door. The feelings bubbling inside her lacked a name. She couldn’t explain how, but she knew he wouldn’t hurt her—not physically—not really. Every man could break her heart—that was a fact—and Royce was every bit a man.

  She’d never been spanked before, not even as a child. He had been upfront with her from the beginning. He would use it as a punishment if needed. He’d given her an out, a way not to be in the situation. Why hadn’t she told him? What was to be gained with pushing him? Forcing him to prove he meant what he said?

  The past loves of her life had made many promises, and very few of them had delivered. This wasn’t a promise of a night of passion. This was a promise of pain. Of punishment.