WINDY CITY: The complete series

by Stone, Measha

  He seemed to want an answer, so she muffled out a, “Yes, Daddy.”

  “Good.”

  The cool surface of the wooden paddle pressed against her ass, and she squeezed her eyes shut.

  “Next time you think about keeping secrets and lying to me, I want you to remember this,” he stated before the paddle disappeared and reappeared with great flourish.

  She yelled out and grabbed the pillow from the corner of the couch, pushing her face into it as the paddle came down again and again over her hot ass. The gag made things worse. She couldn’t keep her spit from spilling out all over chin, mingling with the tears rolling down her cheeks.

  “Almost done, sweetheart,” his voice softened, but the spanks did not.

  She wiggled from side to side, trying to avoid the fire beast being unleashed across her ass, but he stilled her easily enough with a heavy arm wrapped around her waist.

  “I’m sorry! I’m sorry!” she cried out, but with the gag, she doubted he understood anything she said.

  She’d been so wrong. Behaved so poorly.

  Every hot smack of the paddle reminded her bad decisions came with bad consequences. The embers of her ass probably glowed from the spanking, but he didn’t seem quite finished yet.

  Over and over again, the paddle licked at her. The sting melted into a burn, only to be reignited when he brought it down again. Every inch of her ass, and then her thighs, were kissed by the wicked wood.

  She’d never sit again.

  And she deserved it.

  She’d been such a bad little girl.

  “I’m sorry, Daddy. So sorry,” she muffled out. The fight left her, and she stopped wiggling. She’d been wrong, veered them off the course they’d been on, and her Daddy was putting them back to right.

  Quiet sobs tore through her, and she squeezed the pillow beneath her chest, hugging it tightly as the paddling came to a slow stop.

  Ryder rested the paddle on her ass and unwrapped his arm from her waist. Feathery strokes of his fingers trailed down her back.

  “Shhh, it’s okay, sweetheart. It’s okay,” he soothed her, rubbing her back, but not touching her ass or thighs. He wouldn’t be rubbing away the sting, because she was supposed to remember this lesson for a long time.

  And she would.

  Chapter 20

  His little girl had taken her punishment well. She fought at first, but he couldn’t blame her. He hadn’t given her an inch. Every spank of that paddle came down on her upturned curves with intentional force. She would learn this lesson—and learn it well.

  But the struggles slowly faded away, and acceptance filled her body and soul.

  Her bottom practically glowed up at him. His little girl had been stubborn, making her spanking longer than it needed to be, but he wouldn’t be deterred.

  “You did good, Sammy,” he praised her while rubbing her back. Her ass probably needed soothing more, but he wouldn’t touch her there. The burn would continue, unaided with relief. She’d earned it; she would keep it.

  The paddle wobbled on her ass as her sobs eased away. When she quieted enough, he removed it and tossed it onto the coffee table. The blush of her bottom had brightened into a cherry red as the paddling continued, but now, after a few minutes of settling in, her cheeks were raw and crimson. A small bruise already formed on her left cheek. She’d feel that for a day or so.

  And rightly so.

  “You ready to get up, sweetheart?” He always found it somewhat odd how quickly he could shed his anger over the infraction once his little girl was in her place over his lap. But with Samantha, it was different. The purpose of her spanking wasn’t merely to punish her, it went deeper. This wasn’t just a spanking for breaking the rules—no, this had a stronger meaning. He was wiping the slate clean, teaching her and strengthening them at the same time.

  A muffled agreement came from her, and he pulled gently on her shoulders.

  “Come on. Up you go.” He helped her to her feet, but she sank down to her knees in front of him, looking up at him with pitiful eyes, wet cheeks, and chin.

  He peeled off his t-shirt and used it to wipe away the tears and saliva from her face.

  “It’s okay now, sweetheart. It’s over. Your punishment’s over.” He reached behind her head and unbuckled the gag, though he made a mental note to keep it handy in case she started getting mouthy in the future. As much as she disliked it, his cock jumped at the sight of it tucked between her lips.

  Once the gag was removed, he tossed it beside the paddle and lifted her from her knees onto his lap.

  “Ow.” She gasped and wiggled her ass against him, but snuggled her head into the crook of his neck and wrapped her arms around him.

  He hugged her tight to his chest.

  “I’m really sorry,” she said again.

  “Do you think you’ll keep secrets from me anymore?” he asked, rubbing his hand over the smooth flesh of her back. The heat of her ass seeped through his jeans onto his thigh. Yes, his little girl would be feeling the residual effects of the paddle for a while.

  “No, Daddy. I promise.” She sniffled and hugged him tighter.

  “Good.” He patted her bottom. “We’ll talk about what comes next after breakfast tomorrow.” He placed a chaste kiss to her head. “Is there anything else I need to know?”

  She pushed away from him slightly, bringing her tear-filled gaze to his. “I don’t think so. I think you know everything.”

  He cupped her cheek, rubbing away the runaway tear with his thumb. “No more tears, sweetheart.”

  “You spanked me really hard,” she blurted out in the cutest whine he’d ever heard.

  “You bet I did. And I will again if you earn another spanking,” he promised with a grin. “Hopefully, the next time you’re over my knee, it’s because you’ve been so good, you’ve earned a sweet ass-tanning.”

  She wiped the back of her hand across her cheek. “What’s that?”

  “A sweet ass-tanning?”

  “Yeah.”

  “That’s when I lay you over my lap and spank this beautiful ass of yours until it’s nice and pink. Then, once you’re all warmed up, I spread your cheeks and play with that pretty pussy of yours until you come all over my lap.” His cock ached just thinking about what he would rather being doing at that moment. Her pussy was wet, he didn’t doubt that, and he didn’t need to check. Even though she’d been punished, and she didn’t enjoy the spanking, her body would be reacting to it—and that sweet cunt of hers would be soaking for him.

  She blew out a long breath with puffed-out cheeks. “Yes, I’d rather have that please.” A smile tugged on her lips.

  “You have to be good girl.” He tweaked her nose.

  “Do you have any cream?”

  He wrinkled his brow. “For what?”

  “My bottom. If you rub cream on it—Arnica, I think it is—it doesn’t hurt so much.”

  “Nope. I don’t have any. You earned every bit of the discomfort you’re experiencing, why would I take away what I gave you? Nope. No cream, no rubbing, and no orgasms.”

  She pulled an innocent face, and he laughed.

  “Your little pussy is probably aching to be touched, but not until tomorrow. Do you understand me? You are not to touch yourself until I say so. No orgasms after you’ve been spanked for being naughty.”

  “But I thought the punishment was done,” she pouted.

  “It is, but you don’t get pleasure after. It would only encourage you to wonder if the punishment was worth the playtime, and I don’t do that.”

  She scrunched up her lips and sighed. “Okay. I guess that makes sense.”

  Her little side had completely taken over now. After a thorough spanking like he’d given her, he figured she’d be sweet until the morning at least.

  “Let’s get to bed,” he announced, then eased her off his lap.

  “I’m not tired yet,” she said, but he only had to touch her ass to get her to step quickly toward the hallway. “Okay, ok
ay.”

  “My bed, sweetheart. I want you in my bed.” He cupped her elbow and led her to his bedroom.

  “To make sure I don’t touch myself?” she asked with a flirty grin.

  He laughed.

  “No, because I like having you in my arms. And tonight, we may not be fucking, but we’re re-connecting. Now, get your little ass beneath the covers. I’m going to turn off the lights and lock up, then I’ll be in to tuck you in.” He swatted her ass lightly, and she jogged to the bed. Seeing her tits and ass bounce with her motions made him regret his rule about no playing after a punishment.

  She pulled back the blankets and climbed into the bed.

  “Okay, Daddy.”

  “Do you want your bear?” he asked, remembering the stuffed animal she’d been cuddling during a nap.

  She shook her head. “I don’t need him if you’re here.” Pulling up the blanket to her chin, she buried into the oversized pillows.

  “I’ll be back in a minute,” he assured her, then turned off the lights, leaving the door open to let the hall light illuminate part of the room.

  As he went about gathering up the paddle and pacifiers and shutting down the apartment for the night, he pictured having Samantha in his bed every night. But they’d said this was temporary, just while she was staying with him—until she found her own place.

  He checked the bolts on the front door, then headed back to his room where she lay waiting for him.

  How was he ever going to give this up?

  Chapter 21

  Samantha slipped the razor back into the drawer in the bathroom and tightened the towel around her chest. Unwinding the towel from her hair, she ran her fingers through the short locks to work out any tangles, then hung up the towel and made her way to the guest bedroom.

  Sleeping next to Ryder had given her a solid night’s rest. With his heavy arm anchoring her to him, she eased into his strength and heat. The man kept the air conditioning at full blast, which worked fine for her. She either got to snuggle under his thick quilts or he kept her pressed to him all night.

  She had no complaints.

  Other than still having a sore ass when she woke up. But she could admit it was her own doing.

  “Sam?” Ryder peeked his head into the guest bedroom where she stared around the closet, trying to pick out something to wear. It was going to be another hot and humid day in the city. Maybe a trek down to the lake was in order.

  “I’m getting dressed.” She started flipping through her sundresses. “But I think I’ll put my suit on and go to the lake. It’s gonna be hot again today.”

  “I already told you you’re busy today.” He stepped into the room.

  She stopped searching and turned her attention to him. “Doing what?”

  “First, we have to have breakfast, then we need to discuss the new rules and the next steps in dealing with Randall. Then, this afternoon, I thought I’d take you to a movie so we wouldn’t be out in the heat.” He leaned his hip against the dresser and casually folded his arms over his chest.

  “You don’t like the beach, do you?”

  He grinned. “I really don’t. All those people and sand gets everywhere. And the water is either too cold or the sand is too hot.”

  “How about I go to the beach this afternoon, and you can take me to a movie tonight?” She offered a compromise.

  “I really don’t want you going out alone right now. Not until we get more information on Randall and what he’s up to,” he said, his brow wrinkled in concern.

  She let out a low breath. “I knew as soon as you found out, you’d lock me up.” She yanked a dress from a hanger.

  “No, that’s not what’s happening.” He shook his head.

  “Yes, it is.” She ripped the towel off and threw it to the floor before shoving the yellow floral cotton dress over her head. “You’re going to make me stay hidden until it’s over with. I’m an adult, Ryder. I can actually take care of myself. I’ve been doing it for a pretty long time,” she said as soon as her head popped out of the neckline of the dress.

  “I never said you couldn’t. And, grown woman, I’d remember how red your ass still is from last night’s spanking before you let your temper get any hotter,” he said in a low tone.

  She pinched her lips together, fighting back the retort burning her tongue. As irritated as she was, she didn’t want another spanking. Her backside was still pink and sore.

  After a calming breath, she relaxed her stance. “I don’t want to be caged up.”

  He stepped toward her, placing his hands on her shoulders. “I know, and I don’t want to lock you away. But I want to be sure you’re safe. It’s Saturday, and the beach will be crowded. Tell you what, I’ll get in touch with a friend of mine. He used to be a Chicago cop. I’ll see if he has any ideas of what we can do from here. No lake for today—only today—until after I talk to Kendrick. Okay?”

  If he hadn’t looked so damn reasonable and mouthwatering when he presented his compromise, she wouldn’t have given in so easily.

  “Okay. I guess I can do one day of prison time.” She dropped her shoulders. Just because she was complying didn’t mean she had to enjoy it.

  He cupped her chin in one hand and pulled her head back. Desire danced in his eyes as he lined up his gaze with hers.

  “Prison, hmmm? Being locked up with me is like being in jail?” He spun her around and yanked her wrists behind her back. “I think I can work with that.” Pulling her against him, he reached around her body, scrunching up the skirt of her dress until his fingers touched her pussy.

  She went slack against him, no longer caring about the little burn in her shoulders from being held in such a way. His fingers pried apart her lips to find her clit, forcing her to her toes when he pinched the sensitive bud.

  “Does my little prisoner have a wet pussy?” His breath was hot against her ear, ramping up her aroused state a few more levels.

  Too wrapped up in the sensations his fingers were causing, she merely nodded.

  “I’ll need to restrain you better. This way, my little prisoner.” Taking away his erotic touch, he pushed her forward and marched her from her room to his. She pulled slightly, thinking to give him chase, but he struck her ass with a sharp spank.

  “None of that,” he chastised, but she could hear the playful tone dancing beneath the surface.

  When they entered his bedroom, he pulled her to the closet.

  “Face the wall.” He positioned her to his liking. “Don’t move, or I’ll have to discipline you,” he said with mock sternness. It wasn’t anything like when he actually warned her abut punishment. This tone was a promise of fun and excitement. The temptation to try to run was there, but she didn’t want to push him too far.

  Even playing, she suspected her Daddy like to be obeyed.

  Ryder came out of the closet with a pair of fuzzy cuffs dangling from his finger and a silly smile playing on his lips.

  “Where did you get those?” She laughed.

  “I don’t remember.” His grinned widened. “But they’ll have to do.” He stepped behind her, shoving his bare foot between hers and kicking them out wide. “I’m going to have to strip search you first—prison rules.”

  The cuffs made a jingling sound when he shoved them into the back pocket of his jeans, then he grabbed the hem of her dress. Not one to play too easily, she didn’t raise her arms up for him.

  “Sam, arms up or I’ll tear it.” The promise didn’t go unheeded. She put her hands in the air and the dress swished right off her body. The chill in the room brushed across her naked nipples, hardening them into peaks.

  Her arms were pulled back behind her again, and the fuzzy cuffs locked into place.

  “They tickle.” She laughed.

  With a tight fist in her hair, he dragged her head back until she was pressed into his chest and barely able to see his expression. Dark and devious.

  Delicious.

  A slight tremor ran through her body the longer he
stared down at her.

  “Don’t worry, little prisoner, you won’t be giggling for long.” He propelled her forward and shoved her to her knees. “Face me,” he ordered, and she scrambled around on her knees until she was face-to-crotch with him.

  His long, thick fingers worked the button and zipper of his jeans. She licked at her parched lips, already craving more. He shoved his jeans down and kicked out of them, sending them across the room. Her eyes focused intently on his cock bobbing in front of her. She opened her mouth and leaned forward, wanting a taste, but his hand went back into her hair, pulling her away.

  “No, no, no, little prisoner, you have to earn this cock first. You’ll have to answer a few questions.”

  She blinked.

  “Like what?” She shuffled on her knees, trying to arch upward enough to alleviate some of the strain on her hair.

  He bent over, bringing his face closer to hers. His gaze held her captive. “Why is your ass so red?”

  Heat coursed through her veins.

  “I got a spanking last night.”

  “Who spanked you?” He narrowed his eyes.

  Her heart was in a breakneck race with her breathing. The musky scent of his aftershave mingled with the dominating set of his jaw stirred her insides into a frenzy of desire.

  “My Daddy,” she whispered, lowering her lashes slightly.

  He gave a soft laugh.

  “That’s right. And why did your Daddy spank your ass?”

  “Because I was naughty.” This wasn’t part of her punishment, was it? To have to relive it and have him be upset with her all over again? It would be too much. She didn’t want to go back to being sad; she wanted the slate clean.

  “That’s right,” he said in a husky tone. “But you’re not naughty now, are you, little girl? You’re my dirty little prisoner. Isn’t that right?” He nudged her chin when she started to lower it.

  A playful smile crept across her lips. She could get on board with this game. Hell yes, she could.

  “I’m your dirty little prisoner.”

  He flicked his tongue over her lips. “That’s right, sweetheart. You’re Daddy’s dirty little prisoner. Now, open your mouth for me.” He straightened up to his full height, leaving his fist buried in her hair.