Windy City: The Complete 5 Book Series

by Measha Stone

  "Go into my bedroom, remove all your clothes, and kneel beside the bed. Keep your hands folded behind your back and your eyes cast down."

  “Of course.” She sauntered away. Looking over her shoulder, she smiled radiantly before disappearing down the hall.

  She would be the death of him if he didn't get inside her soon, but it was a death he willingly accepted.

  He headed into the kitchen to get two bottles of water and some grapes. On the way to the bedroom, he stopped at the linen closet to gather a few hand towels and tucked them under his arm.

  He paused outside his bedroom door. Taking in a calming breath, he gathered his control. A beautiful woman knelt on the other side of that door, and he was going to take great pleasure in making her unravel.

  Chapter 24

  The door creaked as Alex swung it open. Alyssa remained with her eyes downcast as he'd instructed, but it took all the willpower she possessed to obey his command. She'd managed to get to his room and undressed quickly, hoping he wouldn't arrive before she was ready.

  Not sure of what was to come, she had tried to anticipate what he'd want from her. The men at the clubs she played with were really just friends who knew how to wield a paddle or flogger. It had never been truly sensual or sexual in any way.

  Alex was different. He wasn't just a Dominant who wanted rules and order. True, he expected her obedience, but he wanted everything else too. He watched dorky movies with her late at night. He hugged her tightly whenever they embraced, and never once did he make her feel less than him. In fact, he always made her feel important, secure. She wanted to get this right for him, to set the scene correctly.

  She glanced around the room for something to enhance the scene he'd find when he walked in. The warm cherry four-post king-sized bed took center stage. Not only was it extremely comfortable, but also looked to double as a toy. The thick crafted posts stood straight to the ceiling, but from the end of each protruded delicately fashioned wrought iron pillars that met in the middle of the bed. She imagined being tied to the bed, standing and her hands bound to the iron posts above her. The things a person could have done to them in that position!

  She remembered seeing a black footlocker in his closet and padded to the closet to inspect it. No lock. Inside were several implements: paddles, mini canes, floggers, and other boxes. She opened the one on top and found the exact thing that would add a bit of flare to their evening: a pair of leather cuffs chained together. Acting quickly, she secured the first cuff around her wrist. The friction of the cuff against her still healing burn made it uncomfortable, but she managed to get the clasp secured.

  Kneeling beside the bed, she put her hands behind her back and managed to hook the cuffs together. The door handle turned as she finished putting herself into position.

  He entered silently, closing the door behind him, but saying nothing to her. His footsteps fell beside her as he made his way to the nightstand behind where she knelt. He placed several items on the table before he turned to her.

  The silence made her nervous. She wanted his words, his touches, and the lack of both worried her. Just as she was about to break her silence, he stood in front her. His hands dug into her hair and he pulled her head back to look up at him. The pleasure and joy she expected to see eluded her. Instead firm, frank eyes glared down at her.

  "Where did you get the cuffs?" he asked.

  "The footlocker in the closet," she said, searching his expression. Displeasure. She’d done something wrong.

  "What were your instructions?" he asked, releasing her hair and moving down to his haunches, keeping their eyes locked.

  "To come in here, strip, and kneel with my hands behind my back and my eyes downcast."

  Before she could continue, he spoke. "And in those instructions, where did I say to go into the closet and dig out a pair of cuffs?"

  "Nowhere, but I—"

  "You are trying to control the situation." His words were given in a soft tone, but the implication was harsh.

  "What? No. I was trying to add to it, to give you more of what you wanted." She wished they could have this discussion clothed.

  "What I want, what I desire, is your submission, your obedience. If I want your hands cuffed, I'll give you the instructions or I'll do it myself. You wanted your hands bound. You wanted to feel the cuffs on your wrists. Those were your desires."

  "Don't my desires matter?" she asked with an edge she quickly regretted at the raise of his eyebrow.

  "Of course they matter. And I will always take them into account. When you submit to me, you trust me to give you what you want, what you need, and push your limits, but you don't control what happens."

  The casual, go-with-the-flow man had the expression of a serious Dominant. Thinking on his words, she couldn't argue. It was what she wanted, and she'd pretended she was serving him by doing so. She had completely tried to top the scene from the bottom.

  "I didn't think. I'm sorry. I was—"

  He shushed her with a kiss. His hands cupped her face as he continued to invade her mouth with his tongue. Her insides melted.

  "You were topping from the bottom." He smirked. "You'll learn not to. It won't get you what you want. There are ways to ask for what you want. For example, if you had wanted this, you could have asked me in the hall. You could have expressed your desire to be bound, and I would have either declined or accepted the suggestion. But since you didn't, I think these will have to go." He reached around her and unhooked the cuffs, bringing her hands forward. She watched as he unbuckled each one and removed it from her wrist. "Your burn. You've reinjured it." He tossed the cuffs onto the bed.

  "It's just a little raw, no damage," she insisted. She was ruining everything.

  He looked it over, then at her. "No binding until this is completely healed."

  Nothing in his tone suggested she had room to argue.

  "Eyes back on the ground. Hands resting behind your back." Without hesitation, she positioned herself.

  He dropped two implements onto the bed. What if she didn't like them? What if she wanted something else?

  "Stand up, baby." His hands steadied her as she managed to get to her feet. "Link your fingers behind your neck. There you go. Good."

  She wanted his eyes. "Can I look at you?" she asked.

  "Yes. You can look up now." When she did, she his features light, a gentle upcurve of his lips.

  "See? Not so hard." He gave her a quick kiss and leaned over the bed. A riding crop appeared before her eyes. "Have you ever experienced this?" His question focused her attention on the crop. It looked no different than any other crop she'd seen, so she nodded. "Anywhere other than on your ass or back?"

  "No," she answered, feeling confused.

  "Take a few steps toward the windows away from the bed." He moved himself in the same direction, and she met him. "Tilt your head back for me. Give me open access to those beautiful tits of yours."

  Alyssa raised her chin, tensing with anticipation, waiting for the first strike. The crop stung her ass. Would it be worse on her breasts? Instead of a streak of fire landing across her chest, Alex’s mouth wrapped around her nipple. His warm, wet tongue rolled around and around, drawing out her arousal.

  He pulled away from her, quickly replacing the sweet sensation of his mouth with a sharp snap of the crop. She jumped, but stayed in position.

  "Good girl." He moaned as he brought the crop down equally as hard on the other breast. "They bounce so fucking nice." The barrage of slaps continued alternating between breasts, but never striking the same place twice. He spared the peaks of her nipples at first, concentrating on the meaty flesh, but once a blanketed heat covered her, he delivered two sharp slaps to each nipple. She kept her fingers linked, but folded inward, bringing her elbows in to protect herself.

  "Uh-uh. Back in position," he ordered, and she took her time complying, needing a moment to catch her breath. When she didn't immediately obey, he used the crop to deliver two punishing swats to her ba
re ass. "Back in position, Alyssa. Now."

  She managed to straighten up, leaving her breasts once again exposed.

  "There, that's easier, isn't it?" He ran the fat slapper along her chin, then down her neck, and between her sore breasts.

  "Yes." She could breathe much easier in that position.

  "How are you doing?" he asked as he continued to run the slapper over her breasts, soothing them with the leather touch.

  "Good. I'm good." She nodded.

  "Do you need a short break?" Be honest with me,” he warned.

  "No. I'm okay now."

  "Good. Spread your legs. Further, past your shoulders. That's it."

  "Do you have any idea how hot you look right now? Your tits are all rosy red, your ass is perfectly white, and your pussy is just here for me." He reached down and lightly stroked her folds, not delving in or applying pressure, just a feathery touch.

  "Alex." She moaned and tried to push into his hand.

  "No. Don't move. This is my time." His words softened. His fingers continued tormenting her as he brushed against her clit but gave her no actual relief. "So fucking wet already." He groaned.

  He slid to his knees in front of her and pressed his mouth to her wet, wanting clit. She moaned as his tongue slipped out of his mouth and stroked her swollen clit. The torment continued for only a few moments before he leaned back on his heels and aimed the crop at her arousal. One sharp slap to her clit had her jump up and close her legs.

  "Get back," he ordered. She repositioned herself and readied for the next blow. Two more delivered to her inner thighs. "Open wider."

  He stood from his position on the floor and stood directly in front of her. The crop hung in the air, positioned just below her pussy, between her legs. "Still doing okay, baby?"

  "Yes." She swallowed, waiting for the next strike.

  "Do you know what I'm going to do next?"

  "No." She kept her eyes entwined with his, the connection helping her breathe through the burning in her loins. She wanted him badly—his hands, his lips, his cock.

  "Oh, I think you do." He tapped the slapper to her wet lips. "Tell me."

  "Alex."

  "Tell me, Alyssa."

  "You're going to spank me."

  "Where?" he taunted.

  She took a deep breath. Verbalizing the actions made them so much more real.

  "My pussy. You're going to spank my pussy," she said on a huffed exhale.

  He laughed. "Very good. Now, tell me when you're ready. Ask me to begin."

  Another ripple of emotions ran through her. "Please," she half whimpered. The slapper didn't move.

  "Please what? Don't make you ask? Don't make you admit you love it? Or please start?"

  "Start." She nodded, and he gave another chuckle.

  "Ask me in a full sentence," he instructed as he ran the edge of the slapper along her folds, enticing her to submit to him.

  "Please spank my pussy," she breathed out, and was rewarded with a sharp smack to her clit. She didn't jump away, but she did gasp and squeezed her eyes shut.

  "And what do you say when you get what you want?" he teased.

  "Thank you," she managed to whisper as she opened her eyes, surprised to find him staring at her. His gaze wandered over her expression, searching and studying her.

  "When you're ready…" He grinned.

  "Thank you, sir, may I have another?" She couldn't suppress the giggle as she made her joke and was quickly compensated with a heartwarming burst of laughter.

  He stepped forward, curling his hand around her neck, where her fingers were laced together and pulled her toward him.

  "Ah, baby, you are such a breath of fresh air. And fucking hot to boot!" He captured her in an impassioned kiss. Forcing herself to remain in position, she lost herself to his warm, demanding lips. He pulled away, leaving her breathless and hungry for more. "Now, stop distracting me." He tapped her nose. "When you’re ready." Another step away from her, he repositioned the crop between her legs, hanging precariously close to her aching pussy.

  "Please continue." She remained smiling and kept her eyes fixated with his. Not looking away, he flicked his wrist and delivered a stinging swat to her folds. She grimaced, but didn't break their enthralled stare. "Thank you," she whispered. "More please?"

  "Good girl." He gave her two more swats.

  "Thank you." She took a few calming breaths. The crop roamed up and down her legs as he watched over her.

  "I think your ass needs some tending to, what do you think?"

  "I'll defer to you on that subject." She spoke cautiously, not wanting to attempt to take control again.

  "Wise choice. I'm sure you won't regret it. Now, are your arms sore? Would you like to put them down?"

  Her muscles were beginning to cramp from the awkward position and the tension from each strike of the crop. "Yes, please."

  "Good girl. Drop them. Then I'd like you to walk over to the post at the foot of my bed. Hold onto it as you stick out that beautiful ass for me."

  She began to rub her arms as she brought them down, but was quickly swatted away by his own. Warm tingles ran through her at his touch as he lovingly massaged her elbows.

  "You should have told me they were that sore," he chastised her. "When I ask you if you're doing okay, I don't just mean the part of your body I'm focusing on."

  "I know. They weren't that bad until I moved them," she explained.

  "To the post. I have the need to use something sterner than the crop. I'll be back." He disappeared back into the closet.

  Chapter 25

  When Alex returned, rubber paddle and cane in hand, he found Alyssa’s wide eyes glued to him. Her lips moved, but he couldn’t make out what she was saying.

  The rubber paddle dropped to the bed next to where she stood with a heavy thud, the cane made no sound at all as it lightly landed. He kept his eyes on her. Her words finally registered. She was counting.

  "How are you doing?" he asked as his fingers ran down her bare back.

  "Okay."

  "Counting the number of ways you're going to thank me later for your spanking?" he teased, and her muscles relaxed beneath his fingers. "The cane can be just as pleasurable as anything else."

  "I've heard that myth before," she whispered, not meeting his eyes.

  He gave a soft chuckle. "I promise, if you don't like it, say your safeword and it all stops."

  She rested her head back on the post. "Okay. I can do that."

  He ran his hands through her hair, combing it down her back until her muscles eased beneath his touch.

  Sweeping her hair across her shoulder, he kissed her neck. "Just relax and enjoy." He trailed his hand down her arm to her hip and changed direction until his fingers found her moist heat. "Damn, Alyssa," he whispered into her ear. "So wet."

  A soft groan escaped her lips as he intensified his touch and rubbed her slick clit. As her body settled into the pleasure he created, he used his right hand to begin delivering swats to her untouched backside. His cupped hand brought only sensual slaps to her delicious cheeks while he warmed her skin for the paddle.

  "This is nice," she breathed as he stroked her clit and began to delve into her folds.

  "Do you know how hard my dick is right now?" He kissed her shoulder. "All I want to do is bury myself inside you."

  She peered at him through half hooded eyes. "Why don't you?" A reasonable question. Why was he torturing himself?

  "Ah, my dear Alyssa, then we would have skipped the race and jumped over the finish line." He placed another kiss to her shoulder and increased the speed and force of the swats. "Your ass isn’t white anymore. In case you were wondering." He pulsated his finger over her clit. "It's a warm rose, and perfectly ready for my paddle." He pulled his hand away from her cunt. Her pout couldn’t have been more beautiful.

  Taking the opportunity, he stripped off his shirt before he grabbed the paddle. The air conditioning was working fine, but the sight of her before him heated
his skin. The rubber paddle pressed against her took up half of her bottom. His fingers found her clit again, and he thrust two fingers inside her. The first swat of the paddle resonated throughout the room, as well as her gasp—either from the thrust of his fingers or the sting of the paddle. Either way, he grinned and delivered another swat. Each stroke came with a thrust of his fingers. Soon, she was arching her back, taking more of both, sighing and moaning with pleasure.

  He nearly came undone when she threw her head back and let out a low, gut-wrenching moan of unbridled rapture. Moving along quickly with his plans, he managed to toss the paddle onto the bed and grab the cane without removing his hand from her pussy. She was close, he could feel it. Her body clenched around his fingers and her eyes were dilated and glossed over.

  "Baby, it's time for the cane," he whispered. "How are you doing?"

  "So good," she said without hesitation. "Please. Don't stop." She ground her hips, trying to take more of his fingers into her when he started to withdraw them.

  He gave a light chuckle. "Since you asked so nicely." He pressed the cane to her ass and gave her several gentle taps before delivering one sharp swat while making good on his promise to give her more of his fingers.

  She cried out with the second swat, but he wasn't sure if it was from the cane or the third finger he plunged into her slick passage.

  "You're close, Alyssa." He struggled with his own voice. Her reactions were so honest, so pure, it drove his own arousal to the brink.

  She'd been so trusting, so open to letting him guide her. Once she'd given over the power, she’d submitted to the moment, surrendered in all ways. She became settled, focused, relaxed in her submission, which brought a new level of calm and ownership to his dominance.

  "Very close." Her voice was tight as she ground her pelvis toward his hand.

  "Come for me, baby. Come like this, taking the cane for me like such a good girl." He pushed the heel of his palm against her clit, rubbing her harder as he increased the speed of his thrusts. The cane lightly bounced off of her red-striped ass. Her breath hitched, and she clenched her eyes shut as he pulled the cane back and delivered another stinging blow. Her orgasm exploded.