WINDY CITY: The complete series

by Stone, Measha

  With her nose pressed firmly in the corner, she put her hands on her head as instructed. He took a moment to soak up the vision before him. Her back muscles were taut, and her plump ass was soft. Another time, he would caress her curves, pat her, and watch the sweetness of her bounty bounce. But this wasn’t that time. This was a punishment…for her. He wasn’t going to be denied.

  Leaving her to her thoughts, he went to his closet and retrieved the new toys he’d purchased. She hadn’t seen the new vibrator yet.

  He ripped through the packaging and placed the vibrator on the nightstand. Next to it, he put the plug and lubricant.

  “Daddy?” she prompted from the corner.

  “Turn back around, Sammy. Don’t add to it by disobeying me now,” he warned when his gaze locked on hers. Peaking over her shoulder wasn’t facing the corner like he’d ordered.

  “You have a butt plug there.” Her voice sounded muffled from being stuffed in the corner.

  “Yes, I do,” he confirmed, gathering up the packaging from the vibrator and tossing it in the garbage can beside his nightstand.

  “I—I don’t like butt plugs.”

  He grinned at her back.

  “It won’t stay in long. Just long enough to prep your ass for Daddy’s cock.” He crossed his arms over his broad chest. He wasn’t quite ready to let her out of the corner.

  Her shoulders slumped, and her head fell forward.

  “I really don’t like that,” she muttered.

  “Oh, you’ll hate it,” he promised. It wasn’t going to hurt; she wouldn’t hate that part. But she would be in a miserable sorry state by the time he was finished with her.

  “I’m really sorry,” she whispered.

  “I know you are, baby.” He placed his hands on her shoulders. “This isn’t about making you sorry, it’s about correcting you and giving you a consequence, so you learn not to do it again.”

  She sighed, resolved to take her punishment.

  “Good girl. You can drop your hands, but I want you to go over to the bed, bend over, and pull your ass cheeks apart real wide for me.” He patted her bottom and shifted his stance to let her pass.

  She cast him a sad glance on her way to the bed, and she dragged her feet across the carpeting until she got there. He pinched his lips together to keep from laughing when she plopped herself over the end of the bed.

  “Open your ass cheeks,” he directed when she seemed unlikely to continue on her own.

  With a mortified groan, her hands flung back to her cheeks, and she gripped them, pulling them open.

  Her tight ring peeked at him, ready for the punishment to begin.

  Ryder picked up the small bottle of lubricant and poured a generous amount on her asshole.

  “Clenching won’t help, little girl,” he warned as her body tensed. He put a dollop on his fingertip and massaged the tight muscle until she relaxed enough for him to slip inside.

  “I don’t like this,” she whispered.

  “You loved it when I had my finger in your ass and my cock in your pussy,” he pointed out to the back of her head.

  “That was different.”

  “Yes, you weren’t a naughty girl that time. But you acted very naughty today, didn’t you?” He tried to firm up his voice enough to hide the lust filling him.

  “Yes, Daddy.”

  He removed his finger and plucked up the plug. “I’m putting the plug in now. You have to keep it in, Sammy, no matter what, okay?”

  “Yes.” Her fingernails dug harder into her ass while he pushed the purple plug into her ass. The muscles stretched around the wide base, and he twisted it while pressing forward until it popped into place.

  “There.” He patted her ass cheeks. “You can let go now.”

  She released her ass.

  “No, no, stay down.” He placed his hand to her back when she started to get to her feet and picked up the vibrator from the nightstand. A small, handheld, wand-like toy meant to stimulate the clitoris.

  “Lift your hips a bit.”

  He wiggled the vibrator beneath her until he positioned it directly at her clit, then flicked it on.

  “Oh!” She jumped slightly, but his hand on her back kept her in place.

  “Does that feel good?” he asked, sitting next to her on the bed. He wiggled the vibrator beneath her, watching her body responds to the pleasure he gave her.

  “Oh…yes…” She turned her head, smiling at him.

  Poor thing thought she was being let off easy.

  He tapped the plug with his other hand.

  “Good.” He pulled at the base of the plug until it started retreating, then thrust it back inside.

  “I…oh—Ryder…” Her hips began to gyrate against the vibrator, her legs tightening.

  “You want to come, sweetheart?” He thrust the plug back in harder.

  “Yes!” She pushed herself up to shove her ass back at the pleasure giving devices.

  “You’ll need to wait.” He flicked off the vibrator. She gasped, then groaned.

  “No, no!”

  “Oh yes. Roll to your back,” he commanded, moving the toy from her.

  She climbed onto the bed and maneuvered herself to the edge.

  “Feet flat and drop your knees to the sides.” He pointed to her legs.

  She frowned but obeyed.

  “Good girl. Let’s try again.” He placed the vibrating head back onto her clit, rubbing it up and down her pussy, teasing and drawing out her arousal, until he could see her testing again. Her lips were pressed thin, nearly white.

  The girl thought she’d sneak an orgasm past him.

  “Tell me when you’re going to come, Sammy. Tell Daddy, or we can replace this plug with some ginger.”

  Her eyes flew open at the threat.

  “Please, I really…oh…fuck…I have…oh…”

  He clicked off the power again, and she growled.

  “You tried, that was good. But you still have to wait.” He laid the vibrator on her stomach and unbuckled his belt.

  “How long do I have to wait?” she asked, her breasts rising and falling faster after her last close encounter with her orgasm.

  “’Til morning.” He wouldn’t lie to her or tease her about that. “Naughty girls don’t get to come, remember?” He worked the buttons on his jeans open and shoved them down, along with his boxers, pushing the items away with his foot.

  “But…” her words trailed off when her gaze lowered to his cock. Stroking himself, he stood over her.

  “One more time, then I’m going to fuck this pretty asshole of yours.” He tapped the plug hard with his forefinger, and her eyes clenched.

  “Ryder…please…”

  He moved from the bed to the floor.

  “Oh no…if you do that…oh fuck!” She cried out when his tongue brushed across her clit. He pushed the vibrator away, deciding to give himself another treat.

  “So sweet,” he muttered against her wet sex. He ran his tongue through her lips, ending at the swollen nub, and flickered his tongue over it.

  “Oh no…” she moaned. He grabbed her thighs and pressed them to the mattress when she tried to clamp them closed. “I can’t hold it, I can’t wait…” she cried, sounding miserable.

  “You better, or your pussy will get the belt.” He went back to suckling her clit. Fuck, she tasted so sweet. Round and round, he rolled his tongue over the sensitive nub.

  Her muscles strained beneath his hands. So close.

  “Oh god! I’m going to come! Ryder! Daddy!” she screamed, pushing her hands against his head.

  He took pity and lifted off her pussy, wiping her juices from his lips with the back of his hand.

  “Good girl.” He grinned down at her. “Such a good girl.” He moved back to his feet. “Take a deep breath, sweetheart,” he warned as he pulled the plug free of her ass.

  “Daddy…” She looked up at him with yielding eyes, pleading with him.

  “I never go back on the punishment I pro
mised; you know that.” He stroked his cock and lined his head up with her tight pucker. The plug loosened her, readying her for him.

  “I’m sorry, I won’t run away again, I’ll listen,” she promised as his round head pushed through the ring of muscle.

  “Daddy…” she whined.

  He pushed her legs farther back and glanced down at his cock sinking into her asshole.

  “Almost done, baby. Then your punishment will be over.” He thrust hard into her ass, grabbing hold of her legs as yelped from the sudden intrusion.

  He held still for a long pause, letting her adjust to the fullness of his cock. So fucking tight. He gritted his teeth. She needed another second.

  With the tip of his thumb, he circled her clit, bringing her down from the sudden pain to the warm fuzziness of pleasure. Her eyes softened, and her lips parted as her breaths came faster.

  “You’re getting close again, aren’t you, baby?” He forced his voice to work as he pumped his cock in and out of her tight ass.

  “Please…” She grabbed his arms, digging her fingers into him. “Please.”

  “No, little girl. You will not come. You will hold it and wait.” He condemned her to a fate of unbearable arousal, driving his own need to fuck her forward. He plowed into her ass harder and faster, watching the little twitches in her muscles as she took his cock like a good girl.

  “So good. Such a good girl for Daddy.” He thrust faster. “Fuck, sweetheart.”

  “Please!” she begged as his thumb tapped over her clit.

  “Fuck,” he growled and removed his hand from her pussy, leaning forward over her body, pressing his hands into the mattress beneath her.

  “Oh god.” She whined and grabbed ahold of his shoulders.

  “Hold your legs open for me. Hold them wide.” He continued to plow into her, feeling his release barreling down on him.

  She obeyed. Without question. Without hesitation. She linked her arms around her knees and pulled them apart wide.

  He slammed into her ass, driving straight for his release.

  “Fuck,” he hollered, pumping once, then twice, before stilling. His cock burst with relief as his come spurted inside her ass. “Fuck,” he said over and over again, until the last pulse of his orgasm faded away. He let out a hard breath and opened his eyes.

  Her gentle, wide gaze settled on him.

  He fell right back into reality.

  “Shit, baby. Are you okay? Did I go too hard?” He’d lost himself. He never did that, but her immediate obedience to do something she knew wouldn’t get her any closer to her own orgasm had kicked him into overdrive.

  “I’m fine. Yes, I’m okay. Ryder, I’m okay,” she said, framing his face with her hands. “You weren’t too hard. It…it was…” she swallowed, “it was perfect. Horrible punishment, but perfect.” She strained her neck and placed a kiss on his lips.

  He captured her mouth beneath his. His fingers entangled in her hair, and he held her to him, sweeping his tongue past her lips, taking the kiss deeper, feeling her beneath him, warm and willing. Her arms wrapped around him, holding him to her.

  “Samantha,” he breathed her name when he finally broke off the kiss, resting his forehead against hers. “How…” he stopped his words from falling out. He couldn’t ask her that. Not yet. But how he would ever be able to let her go was beyond his comprehension.

  “Are you okay?” he asked after another moment stretched between them.

  She laughed. “I already said I am.” She shoved at his shoulders. “But I would like to put my feet down.”

  He gingerly slid from her ass and moved to his feet.

  “Towel?” she asked, remaining still on the bed.

  He opened his nightstand and grabbed a hand towel he’d started keeping in there since she’d spent more and more nights in his bed. Holding her down gently, he wiped his cum from her asshole. Maybe it shouldn’t have affected him as much as it had, but seeing his mark on her, seeing his essence smearing across her ass the way it did, filled his chest…with pride? Joy?

  Love?

  No.

  He finished cleaning her up and picked up the dirty clothes from the floor. “You want your jammies?” he asked, heading to the closet to deposit the laundry.

  “If it’s okay, I’d rather stay naked,” she said in a small voice. When he turned to the bed, she was already crawling under the covers. “It’s kinda hot in here.”

  He chuckled. “That’s because you’re horny.”

  “I am.” She nodded with a wide grin. “Want to do something about that?”

  He snagged his boxers from the floor and pulled them up.

  “I would love to, Sam.” He leaned over her. “In the morning. And not a minute before.” He pressed a kiss to her lips, intending for a short peck. But once there, once her warm lips were beneath him again, he couldn’t stop himself from sweeping them away. Just a touch from her was enough to drive him off course.

  “First thing in the morning?” she asked in a husky voice when he straightened, his lips still tingling.

  “I have to get to work early. But, if you want me to wake you up at three a.m., sure- you can have your orgasm before I head out.” He lifted a shoulder.

  She gave an exaggerated sigh. “Never mind.” Not even the promise of an orgasm would get his girl up that early.

  “Take a nap, Sam.” He pressed her shoulders until she was laying against the pillows. “It’s still early. How does fried chicken for dinner sound?”

  She grinned. “Delicious. And macaroni and cheese?”

  He pinned her with a look. “Seriously? Obviously, I should have added a punishment for not telling me about your—”

  “No, no…that’s okay. I think pasta salad would be better.” She put a hand up.

  He laughed.

  “Nap,” he ordered, grabbing his jeans from the floor on his way out the door. She probably wouldn’t sleep for long, but he needed the tiny bit of space.

  That damn love word popped into his head again, and he needed to get that shit under control before he let it slip from his mouth. She had enough complications, having feelings for her that ran deeper than causal would only muddy the waters.

  But when he looked back at her before closing the bedroom door, he couldn’t help the overwhelming sense of emotion coursing through his veins. Already half asleep, she cuddled his pillow with a broad smile on her lips.

  He was in deep trouble.

  Chapter 27

  She got it!

  Samantha threw open the apartment door and rushed inside.

  “Ryder?” she called out, kicking the door shut behind her. He’d left for work so early, he had to be home already. She rushed through the apartment, searching him out.

  Nothing. He wasn’t home.

  Her enthusiastic smile dropped a bit. She shot off a text asking when he’d be home. This was news she wanted to give in person, so she could see the pride in his eyes.

  She’d been so nervous going to the interview, her hands trembled. But she made it through and landed the job. It had been unexpected to have an offer made at the end of the interview, but she hadn’t blinked an eye at accepting.

  She now had employment, with a higher pay scale than she’d expected.

  Her phone chirped.

  Gonna be a long day. Text me when you get to the dungeon.

  She frowned.

  Dinner?

  Sorry, babe. Trying to finish this up this week. Be home to tuck you in.

  Tuck her in? No! She wanted to celebrate.

  She tossed her phone on the couch and sighed.

  Her stomach growled. Having skipped breakfast, thanks to her nerves, she was starved.

  Samantha gathered up ingredients for a sandwich and popped open a can of pop. Ryder wasn’t home, and he would forgive her. It was a celebration. She could have junk for celebration.

  She put the fixings on the counter, pushing aside a folded-up newspaper Ryder must have been looking at while he downed a cup
of black coffee. How could he drink that stuff with no sugar or cream? It was blasphemy.

  As she spread mayonnaise across the bread, she caught the heading on the paper.

  Apartments for Rent

  Her hand stilled while her heart took off into a gallop. She put down the knife and picked up the newspaper. He’d been looking at apartments? For her?

  She was only staying with him temporarily, she knew that. And she wouldn’t bother lying to herself and saying the thought of moving into her own place now that she had a job hadn’t popped into her head.

  Did he want her out so quick? He didn’t even know she’d been offered a job, but there was the rental page, folded over to his neighborhood.

  She left her half-made sandwich and walked into the living room, still looking at the ads. Her eyes read the words, but nothing sank into her mind. Only the dull ache forming in her chest made sense.

  Maybe she’d felt things that weren’t there, made too much out of little signals. He’d punished her last night, taken what he wanted from her body, and let her go to bed needy. Even after they’d had dinner and she’d been good all night, he still wouldn’t give her a release, making her arousal all the more uncomfortable.

  He was a strict Daddy.

  And she was falling in love with him.

  When he’d wrapped his arms around her to sleep, he’d kissed her behind her ear. A gentle peck, but it had been everything. Comfortable, safe, easy…real. It had been real.

  So why was he looking at apartments for her?

  She’d been foolish.

  She’d let her heart get involved, get too close.

  The doorbell rang.

  Someone banged on the door.

  Samantha dropped the paper on the coffee table and went to answer it. Ryder had told her Kendrick’s team would be stopping by to check out putting in security cameras. She needed to get to the dungeon to help George. Bury her mind in work—anything to keep from analyzing what she’d done wrong to make Ryder want to get rid of her.

  She pulled the door open.

  “Anderson?” She gasped at the sight of him. Dressed in his usual suit and tie, he stood at the door with a grim expression. “What are you doing here?”