WINDY CITY: The complete series

by Stone, Measha

  “No?”

  “Do they have purple? I don’t like pink.” She shrugged.

  He sorted through the rack until he found other colors for her to pick from.

  “The green are fine, no blue—that’s for boys,” she said as she swiped the hangers to the side. “Oh, purple!”

  “But those say Naughty Girl,” he pointed out.

  She bit her lower lip and looked up at him with every bit of a seductress. “Well, sometimes Daddies like their girls to be naughty, right?”

  Ryder laughed hard. “Yes, I guess we do.” He nodded. “Okay, we’ll get the green and the purple.” He had her search out her size and grab two of each while he wandered away to the toy section.

  He was holding a pacifier when she found him, hands full of her choices.

  “Those are for babies,” she said, eyeing the pacifier.

  “Yes,” he agreed, still looking through the other choices.

  “I’m…I mean…that’s too young…I don’t…”

  He gave her a side-glance. “Even better.”

  “What?” She stepped closer to him, eyeing the other toys on the shelves.

  He held onto the pacifier in his hand and plucked another larger pacifier gag.

  “Ryder,” she whispered harshly.

  He raised a brow at her.

  “Daddy, I don’t want a pacifier.”

  “Then never give me a reason to use it,” he palmed the gag and looked at the panties in her hand. “You have four?”

  “Yes, but can you please let me pay for them?” she asked, looking up at him, a soft plea in her eyes.

  “No, I said I was buying them.”

  “I know, but…they’re underwear. And it’s not like you can reuse them after…well, later.” She turned her gaze to his chest.

  With one finger, he lifted her chin until her gaze came back to his. “I said I was buying them. A present.”

  “But—”

  He firmed his glare. “Sammy, I said no.”

  She slammed her mouth shut and pinched her lips together.

  “Now, let’s take these up to the counter. Unless you want to look at the paddles?” He made a pointed gesture to the implements hanging on the wall behind her.

  She swallowed hard.

  “No, Daddy. I’m fine.”

  He pressed a quick kiss to her lips. “Good girl. Let’s pay for these and get home so you can try on those panties for me.”

  Chapter 13

  Samantha stood in her bedroom holding her white tank top up around her hips and staring at her ass in the mirror. Ryder had told her to change out of her interview clothes and put on one of the new pairs of panties. At first, she’d been excited. It had been too long since she had a Daddy in her life, and she was eager to curl up in his lap, to feel his kisses, and hugs, but then she’d put on the panties and seen her image in the full-length mirror on the closet door.

  This couldn’t be okay.

  She barely knew Ryder.

  She was supposed to be starting a new life. On her own. Like a normal grown up.

  And she still had the entire Randall fiasco to deal with.

  But the longer she stared at the words Yes, Daddy across her ass cheeks, the more confused she became.

  Ryder knocked. “Sam, you okay?” he called through the closed door.

  “Yeah!” She shoved her shirt back down, not that it covered a damn thing.

  “I’m coming in.” The door opened before he finished his warning.

  “You’ve been in here a long time.” He frowned in her direction.

  “I was just…” she trailed off, not sure what to say.

  “Just what?” he asked, looking around the room. “Not cleaning up, that’s for sure.”

  She followed his pointed gaze to the piles of clothes still on the floor and dresser. She was usually neater than that, but she hadn’t gotten to putting them away yet.

  “It’s my room,” she said, feeling the defiant streak in her making an appearance.

  Both of his eyebrows shot up.

  She huffed.

  “Sammy.” He folded his arms over his chest. “Are you feeling overwhelmed?”

  She blinked. “Yeah.”

  “What helps you when you feel like this?” he asked, curiosity lacing his tone. He wasn’t chastising her for her tone or attitude, but looking for a way to help, to guide her out of the swirling winds of her emotions.

  She blew out air. “Potato chips, dip, pop…and a movie.” She peered up at him. Even with his boots off, he towered over her.

  He laughed gently. “Well, what’s the second thing that helps?”

  “I have chips in the kitchen.”

  “Yes, I saw that, but we just had lunch. Are you hungry?”

  “No, but you—”

  “Okay, so the second thing?”

  She sighed. He wasn’t going to let her binge on junk. Maybe having a Daddy wasn’t so much fun.

  “Movie?”

  “We can do that.” He nodded. “But first, turn around and show me your panties.” He grinned down at her, his muddy brown eyes sparkling.

  She turned around until her ass faced him. Looking over her shoulder, she watched his expression. His tongue ran along his bottom lip, and she wondered what that tongue felt like, how it would feel on her skin.

  “Bend over a little.” He waved his fingers at her.

  She leaned forward and pressed her hands to her knees.

  “Much better,” he said, moving to her side. He stroked her ass with his palm, sweeping it across her cheeks and patting her gently. “They hug your ass perfectly. Just enough of your cheeks are exposed.” He gave a light smack to her curved cheek.

  One finger slipped beneath the elastic band and ran downward toward her folds.

  “Spread your legs for me, sweetheart.” He placed his free hand on her back, pressing her forward a little more.

  Her breath caught in her chest, but thankfully, her mind was still firing off signals to her legs. She wiggled her feet farther apart, and his fingers slid between her thighs, brushing across her pussy lips.

  “Hmmm, I think we need a different position here.” He took away his touch, and she groaned, earning her a playful swat. “Don’t worry, your patience will be rewarded.”

  From her bent over position, she watched him grab the chair from the vanity and place it in the center of the room. He sat down and patted his lap.

  “Come lay over Daddy’s lap.”

  She froze.

  Had she done something wrong?

  “Sammy, my lap isn’t always a place for punishment. When you’re good, like you’ve been all day, it’s also a place for pleasure and reward.”

  She gave a short nod, then padded over to him. He helped her over his lap, positioning her until her ass was where he wanted it, but his knee wasn’t digging into her stomach. Her fingertips touched the carpeting below her.

  His fingers returned, skimming along her skin below the elastic of the panties until he found her pussy.

  “You’ve already made your new panties wet,” he chided, joy in his words. He pushed one of her legs farther out and began to stroke her pussy.

  “Oh…” She moaned when his fingers reached her clit.

  “Ah, there it is. There’s that delicious sound,” he whispered, stroking her back with his hand while working her clit with his fingers.

  He rubbed the sensitive spot in circles, driving her to the very edge of pleasure before he sunk two fingers into her hungry passage. She arched her back, thrusting her ass up at him. She wanted more, a lot more, and harder.

  “Tell me what you want, sweetheart,” he said as he pulled her panties to the side, giving himself more access to her sex.

  “Harder, Daddy. Please, harder.” She heard the eagerness in her voice, and if it had been any other man, any other moment, she would have flushed with embarrassment. But she didn’t have the sense of humiliation, the dirty feel of taboo with Ryder.

  “You want me to
finger fuck your pussy harder? Do you want to come for me?” he asked, pushing a third finger into her passage. She gasped at the fuller sensation. Her hands fisted at the carpet, and her toes curled. She needed him to move again, to thrust hard and fast and shove her into the blissful sensations.

  “Yes. Please.” She nodded feverishly even though he probably couldn’t see her.

  His left hand left her back and snuck beneath her panties, trailing between her ass cheeks.

  “Shhh, no, don’t clamp shut. Daddy’s going to play with your asshole while you get your finger-fucking.” His finger pressed against her tight ring. “Let me in, Sammy.” He slowed his thrusts into her pussy until she finally relaxed.

  “It’s going to hurt,” she said with only a tinge of worry. He wasn’t the first man to touch her there, but she hadn’t had very good experiences. Ryder would be different, she was sure, but not completely sold.

  “It’s only going to make things better.” A finger flicked across her clit, and she forced her muscles to relax enough for the very tip of his finger to push inside. She gasped at the small burn, but once she let her worry fade away, she felt only the honeyed pleasure of his fingers working her pussy.

  “There, that’s my girl,” he said, starting to pick up force and speed. “Come for me.” His voice dipped, his breaths came harder, all of which only drove her deeper into her aroused state.

  “Oh, fuck. Fuck…oh!” She threw her head back, pushing back against his hands as best she could. His finger sunk deeper into her ass, refueling the burn, heightening the pleasure. He fondled every bit of her.

  “Does my finger in your ass feel good?” he asked, slipping it in even further. She gasped at the new sensation. He was being gentle, but it didn’t take away from the intensity.

  “Yes, oh, fuck me. Fuck me!” She screamed as her orgasm exploded through her body. She bucked on his lap, riding his knee, taking his fingers into her pussy, into her ass, while she rode out the never-ending waves of ecstasy.

  Slowly, the haze of arousal and pleasure drifted away, and she settled back over his lap. He eased his finger from her asshole and slipped from her pussy. The panties snapped back into position, and she felt a rush of heat cover her face.

  She’d acted like an animal in heat.

  “How do you feel now? Still overwhelmed?”

  She shoved away the hint of doubt. He wasn’t disgusted with her behavior in the least.

  “No, I really don’t,” she admitted with some surprise. Her chest wasn’t tight anymore, and her mind felt clearer.

  “Ready to get up?” he asked, his hand on her back.

  “Yes, please.” She pushed up off his lap, and he helped her until she was on her feet right in front of him. He looked up at her, from his chair, his bright smile settling her last ounce of fear he’d think her a wanton whore for how easily she’d given in to his touch.

  “I wanted to do that for you since we got to the store earlier,” he admitted.

  “Really?”

  “You were wound pretty tight, sweetheart. You seem more relaxed now.”

  She dragged her teeth over her bottom lip while looking down at his lap. His cock had been pressing into her belly, but now she could see it pushing against his jeans.

  “What’s going through your mind?”

  “Your cock,” she said. Blunt honesty. There was a time for coy, and this wasn’t it.

  “What about it?” He tilted his head, his smile getting wider the longer she stared at it.

  “I didn’t thank you for my presents.” She shrugged. Okay, maybe a little coy would be okay.

  “And you want to now?”

  “Yes, very much.” She nodded.

  “How do you want to thank me?” he asked, his hands going to his belt and unbuckling it. His button and zipper were next, and before she blinked, his cock was free of his pants and in his hand.

  She swallowed back the drool when he began to stroke himself in front of her.

  “I…uh...” She checked his eyes for hesitation.

  “If you can’t tell me—”

  “I want to suck you off.” The words burst out.

  Chapter 14

  Ryder caught his jaw before it fell to the floor.

  Samantha’s gaze latched onto his, the hunger evident in her eyes.

  She’d reacted so beautifully to him while draped over his lap. Her cheeks, round and full, had bounced as he fucked her faster and harder with his fingers. And her ass clenched around his pinkie finger. He’d been gentle, gone easy on her by using the smallest digit. Next time, he wouldn’t be so kind.

  And now, seeing her hard nipples beneath the thin cotton material of her shirt, and the fullness of her lips when she licked them, anticipating his cock in her mouth, he deserved a fucking medal for keeping his load. He loosened his grip on his shaft. Any more pressure and he’d explode all over his own lap.

  “On your knees,” he ordered, pointing to the floor before him.

  Without hesitation, she sank down and placed her hands on his thighs, waiting for permission, for his next direction. Good fucking girl.

  “Open your mouth.” He continued to stroke himself but forced his concentration on her expression and not how fucking good it felt to jerk his dick.

  Her pretty, full, pink lips parted, and she raised her eyes to meet his. So pure, so wanting.

  He shoved the chair back and moved his ass to the edge while gently resting his hand on the top of her head and leading her down to take his cock in her mouth. She latched onto him. Her lips tightened around his head. Her tongue rolled around the underside of his shaft as she sucked him farther into her mouth.

  “Oh, baby, fuck yes.” He threw his head back, needing more air to keep up the race with his heart.

  She bobbed in his lap, sucking and licking while his hand curled into her hair. He lost his ability to breathe when she wrapped her gentle hand around his shaft and began to stroke him as well.

  “That’s a good girl, such a good girl, yes.” He pressed down on her head, holding her steady and thrusting upward until his cock hit the back of her throat. She swallowed, making her muscles tighten around him. “Fuck,” he growled, then let her back for air.

  “Again,” he ordered, pulling her back down while he thrust up. She was ready for him, and took him as deep as she could while running her tongue beneath his shaft and squeezing his balls with her hand.

  “Fuck!” He pulled her off and got to his feet, knocking the chair over in his hasty movements. “Open that mouth for me, pretty girl. I’m going to fuck it hard and come down your throat.”

  She sat back on her heels, looking up at him with her swollen lips and hazy grin. “Oh yes.” She nodded. Greedy little thing.

  Samantha licked her lips and opened wide, keeping her gaze steady on him. He pulled her forward by her hair, and without so much as a whimper, she sucked his cock down. With a clenched jaw, he began to fuck her throat, pulling back and pumping harder and harder, until the warmth and wetness of her mouth drove him to the very end of conscience thought.

  She pressed her hands to his thighs, maybe to steady herself, but not to push away. His good girl kept her mouth open for him, sucking and licking.

  “All of it. Take all of it,” he ground out as his orgasm spiraled the rest of his thoughts from his mind. His body tensed, and after another hard thrust, his release took over. Wave after wave, his orgasm ripped through him, until every last bit of his cum unloaded down her throat and over her tongue.

  He let out a ragged breath when his lungs came back online, and gingerly pulled his dick from her mouth when his brain waves kicked back up.

  “Such a good girl.” He released his hold on her hair and stroked his hand down her face until he cradled her chin. “Did you swallow it all?” he asked, tilting her head back.

  “Yes, Daddy,” she said with a prideful grin.

  “So good.” He helped her stand and hugged her to his chest. Her arms wove around his waist.

 
; After several long moments passed, she pulled back from him and grinned. “Now can I have potato chips and dip?”

  He laughed. So pure and innocent was her face when she asked her manipulative question, he couldn’t help the burst of joy coming from his chest.

  With a quick swat to her ass, he shook his head. “I said no, and I meant it. But we can definitely lounge on the couch and watch a movie.”

  He stepped back and got his clothes in order, watching her expression while he buckled his belt.

  “Do you like belts?” he asked, noticing how captured she was by the jangling of his buckle.

  “Sometimes. There’s something about that sound, though,” she admitted. He knew it, how could he not? No matter a sub or a Dom, that delectable clink of a belt buckle could signal pleasure coming…or punishment.

  “I know what you mean.” He wrapped his arms around her again. Her phone dinged several times in succession from the nightstand, drawing his attention.

  “Probably just Paul checking up on me again.”

  “Who is Paul?” he asked.

  “My brother. He’s a bit of a worrier.” She waved a hand and maneuvered her way to the chirping device.

  Her brother. She had an older brother who probably wouldn’t think it was appropriate for her to play with her host.

  “Everything okay?” he asked when her brows knit in concern.

  “Yeah, fine.” She sank down onto the bed as she tapped out a response.

  “It doesn’t look like it,” he pointed out with his hands on his hips. “What’s going on?” he asked when her text messages were going out as quickly as they were coming in.

  “My brother is being annoying. One sec. I’ll meet you out there.” She flashed him a placating smile.

  “If something’s wrong, you can tell me. You know that, right?” Just because they weren’t looking to ride off into the sunset didn’t mean he wouldn’t be by her side in a second if she needed him. What sort of Daddy would that make him if he didn’t?

  “I know,” she said, but didn’t look up from her phone. “I swear. It’s fine. I’ll be right there. Promise.”

  He tapped each finger with this thumb, deciding whether to push harder or give space.