Windy City: The Complete 5 Book Series

by Measha Stone

  “Sorry.” She glanced over her shoulder as she arched her back again, offering herself to him. The expression on his face wasn’t angry, but determined. He gave her a soft nod, and she faced the door. The last two strokes of the belt came fast and hard. No time to get her bearings between them, she hopped onto her toes again and rested her forehead against the door, letting the throbbing in her ass subside. Her breathing was heavy.

  She listened as he slid his belt back through the loops, wondering if he would leave her there for much longer. Her answer came in the form of a hug. He pulled her by her shoulders to face him before he embraced her. She looked up at him through wet lashes, though she hadn’t cried through the short spanking.

  “Feel better?” he asked, rubbing her back.

  “I don’t understand,” she whispered, reaching down to pick up her leggings. His hands swatted hers away.

  “Understand what?” he asked.

  “What just happened? Why do I feel so relieved now?” She shook her head.

  “You feel better because we’ve put the issue behind us.” He stepped away. “Are you ready to begin again? Would you like to start over?”

  The burn in her ass had already begun to fade into a warm haze. “Just like that?”

  “Yes. Just like that. Now, I’m going to get some water. I’ll expect you in position in five minutes.” He winked at her and walked away, leaving her to her task.

  It was just that smooth with him. One moment a punishment, the next they were headed to the playground. She knew he wouldn’t hold her attitude against her, and she knew the punishment being her idea, wasn’t really her idea. He had a way about him. He knew exactly how to push her to where she wanted to go without her even realizing she wanted to get there. It was both intoxicating and infuriating.

  Chapter 12

  Royce downed a glass of water and placed the empty cup in the sink. He’d given her enough time to get ready. Her behavior when she first arrived had surprised him but at the same time pleased him. She had quickly moved from the point of petty anger to submissive acceptance.

  The belting hadn’t been at full strength; hell, he wouldn’t even really call it a belting. But it was enough for her. She’d calmed down quickly, and he wouldn’t have seen a reason to punish her other than knowing it was what she needed.

  The longer he pondered her, the more drawn he was to her. He wondered if any of her friends knew how easily she could be undone. A look. A touch. A well phrased whisper. Had anyone taken the time to see the real her, or were they all too dense to see past her facade?

  His breath caught in his throat when he stepped into his bedroom. Damn, she was perfect. Her hair lay in large curls down her back as she knelt for him. Waiting.

  “I have a gift for you,” he said, noticing her slight jump at the sound of his voice. Her eyes were on him as he walked to his nightstand and pulled out a black box he’d stashed there.

  “A gift? Even after—”

  “Shh.” He sat on the bed beside her, pressing a finger to her lips. “I told you, that’s over. I also told you if I want to buy something for you, I will, and the response you are to give is?”

  Her eyes met his, and a smile eased onto her lips. “Thank you.”

  “You’re welcome.” He nodded with a grin of his own. Discarding the lid to the box, he tilted it toward her so she could see its contents.

  “A butt plug?” He nearly laughed when she scrunched up her lips and nose with her discovery of the glass plug.

  He removed it from the box and seated it in his palm. The length looked intimidating, he would agree, but it was the width that most likely had her eyes widening. “I’d like to start training your ass to take my cock, Jessica. I don’t want any part of you to be off limits to me.”

  “I said no to anal,” she reminded him in a soft voice. Worry shone in her eyes, and he brushed the back of his fingers across her cheek.

  “Yes, you did, and that’s why we are talking about this. You enjoyed my finger inside you, right?”

  Her blush made him smile. “Um.”

  “I’ll know if you’re lying.” He brushed a thumb over her lips.

  “Yes. I did,” she admitted, taking in a long breath and releasing it.

  “This is only one more step. I promise we will go slow. You’ll wear this one tonight and for a few more nights before we move up to a larger—”

  “Larger?” She looked as though she were going to run, so he placed a steadying hand on her shoulder.

  “Calm down. Yes, larger, but it will be pleasurable. By the time your ass has been trained with the plugs, you’ll be able to take me with little to no discomfort. But I know your hesitant, so I’m giving you the choice.”

  She looked from the plug still sitting on his palm to him and back again. “What if I hate it?”

  “That’s doubtful, but if you hate it, we’ll put it back on your limits list.” He meant what he said. He wouldn’t force her if she didn’t find it enjoyable. What would be the point? Although, there were times she’d be put in positions that were only for his benefit and her discomfort would aid in his arousal, this, however, wasn’t one them. “I will never force you to do anything you don’t want to do. This,” he lifted the plug into her view, “I think you’ll beg me for it.”

  She eyed the plug as if to inspect it. “Will it fit?”

  “Yes. It will be a little uncomfortable going in, but you’ll adjust to it.”

  She took a long breath in her mouth and a slow release through her nose. “Okay. We can try.”

  He gave a laugh. “Good. Now,” he placed the plug on the nightstand, “Face me, please.” She turned her body, kneeling between his knees. “Before we get to that, I’d like to do a few other things.” He tilted her chin up and brought his mouth down over hers, capturing her in a hot, slow kiss. She tasted of wine as his tongue pushed past her lips. When he pulled away, she studied him with dilated pupils.

  His hands drifted down her shoulders to her breasts, kneading them lightly before he placed his fingers around her nipples. She winced, but made no complaint when he put pressure on them and pulled slightly. Once again taking them in his hands, he weighed them in his palms, brushing his thumbs over her erect nipples.

  “Are you wet for me, Jessica?” The scent of her arousal was already invading his senses. Her tits were sensitive. She loved having them played with.

  “Yes.” No hesitation lingered in her words.

  “Slide a finger in for me. Let me see.” She stiffened at his direction. “Now, please.” With the speed of a silkworm, she pulled her hand from behind her back and slid it down between her legs. He watched her expression as her finger disappeared into her pussy. “Good girl. Now show me.” He wiped her hair away from her face for both comfort and to see her eyes better. A light blush covered her cheeks as she held up her finger, glistening with her juices. He nudged her chin until she looked at him. While keeping her gaze locked with his, he leaned down and took her finger into his mouth. Sucking and licking her delicious offering. “Very nice.” He smiled once he released her.

  He stood from the bed and moved to stand behind her. “Up and over.” His hands lifted her from her knees and helped position her over the bed. Her ass showed no signs of the few strokes he’d given her earlier. He ran his hand over her unblemished flesh and slid his fingers into her crease, where her pussy dripped for him. “Very wet,” he mused. “I’m going to give you a spanking—because I want to, and you’ll take it with no complaint. Understand?”

  She answered by sliding her feet farther apart and arching her back. “Yes. I understand,” she answered, her voice husky and low. He ran his hand over her head, and down her spine. He wondered if she even realized how much she was giving him tonight. She was slowly showing him her soft side, the submissive side he would bet she saw as a negative trait.

  He brought his hand down on her ass hard. She grunted softly. Again and again, he spanked her, watching the delicious bounce of her ass after eac
h smack. He paused, trailing his fingertips down her reddened skin, letting his nails grate against the sensitive area. She hissed.

  “You’re doing very well, so far.” He bent over and placed a kiss to the heated flesh of her as. “We aren’t done yet, though. Reach back, just like you did the other day, and pull your cheeks apart for me.”

  With a heavy breath, she reached back, moving slowly. Was she looking for a reprieve? “Spread your legs a little more…there you go. Beautiful.” He dipped two fingers into her wet passage, her cunt gripping him tightly. “Greedy girl.” He chuckled and removed his fingers, rubbing her wetness over her lips and up to her asshole. At the first touch of his finger, she tensed. “Relax. It’s just my finger.”

  Once she softened her body, he began the spanking again. This time, focusing on her pussy—which he already knew she enjoyed—and her asshole. She moaned but made no protest as he inflicted more forceful swats. He noted how she pushed her ass out to him, to meet the blows with a lustful grace. He couldn’t have asked for more submission than that.

  While he petted her wet pussy—being gifted with a near purr from her—he reached to the nightstand and picked up the plug.

  “Don’t drop this,” he said, placing it on the small of her back. She stiffened at the realization of what it was. “Relax, Jessica. I promise, I won’t put it in until you beg.” He heard She let out a humph, making him smile at her small act of quiet defiance. She could have the moment for now, by the time he finished with her, she would melt in his hands.

  Pulling lubrication from the drawer, he applied some to his fingers. The slick solution felt cool, and he rubbed it between his fingers before spreading it over her tightly closed hole. He grinned down at her resolve but continued his ministrations. His fingers slid up and down her crease several times before dipping into her cunt. She moaned as he pumped his fingers in and out of her a few times, letting his thumb brush against her clit.

  She tensed around his fingers and he pulled out, using his middle finger to press against her tight asshole. Using his other hand, he stroked her clit, easing her tension.

  “That’s it, concentrate on how good it feels when I use my fingers on your pussy.”

  A moment later, he managed to push a thumb into her ass and again she arched up, taking it in. He took the plug from her back and placed it at her entrance as he released his thumb from her. He rubbed harder, bringing her closer to orgasm as he slid the glass plug into her.

  “Oh, it burns,” she said, fingers griping her cheeks hard.

  “It’ll pass,” he promised, drove in a bit more. “Open for me, Jessica. Push back against it.” He gripped her clit, and she arched again, doing as he instructed. “Almost there.” He slowly pumped her ass with the plug, taking it a little farther with each stroke. She pressed her forehead to the bed, and her breath hitched. She was close. “Do you want to come, Jessica?” he asked, stroking her clit lightly.

  “Yes,” she answered without hesitation.

  He applied more pressure to her clit while thrusting harder against the plug. “What else do you want?” He twisted the plug as he pumped it into her.

  A low growl escaped her. “Please, Royce.” She looked over her shoulder. Desire flooded her eyes. He knew what she wanted, but she was going to have to vocalize it. “Please, put it all the way in. Please.” The words were barely audible, but he heard them, and rewarded her by driving forward once more until the plug broke through and was fully seated.

  He continued to stroke her clit while she adjusted to the fullness of the plug. “I’m going to fuck you now. Would you like that? Do you want me to fuck you while your ass is plugged?” He kicked away his already unzipped jeans and rolled the condom down his hard shaft as she nodded earnestly.

  “Yes. Please. Royce. I have to come. Please!”

  He brushed her hands away from her ass and perched the tip of his cock at her entrance. “You have no idea how beautiful you are like this, Jessica.” He let out a growl of his own as he slipped into her opening. She was hot, wet, and tighter than ever with the plug in her ass. She must have felt the fullness too, because she gripped the bedding and looked at him over her shoulder again. “Play with your clit, Jess,” he ordered as he pulled back and thrust into her again and again.

  Her fingers brushed his balls as she played with herself, and he nearly lost control. Her pussy gripped his cock hard, and he could feel her orgasm building, his own barely being held back. “Now. Now. Now!” He plowed into her hard, gripping her waist and fucking her with a force that wouldn’t be restrained. She screamed out as the waves of her orgasm gripped her. He could feel each pulsation of her release, and it triggered his own. The walls of her cunt milked him, pulling every drop of his orgasm from him.

  It took several long moments for him to catch his breath and regain enough energy to move from her. Careful of her sensitive ass, he told her to stay where she was until he cleaned her up. Once she’d been wiped down, he helped her onto the bed.

  “The plug,” she whispered.

  “It stays in.” He smiled. “Just for a little longer.” He grabbed his jeans and pulled them on before lying next to her. She wasn’t planning on spending the night, and if he let his dick touch her flesh, he wouldn’t be able to keep from taking her again, and she was too sore for another session so soon. He hauled her to him and kissed her earlobe. “How do you feel?”

  “Okay. Sore, but good.” She yawned. “Full. Very full.”

  She wouldn’t look at him. “You’ll take it home with you. I’d like you to put it in before dinner tomorrow.”

  “You want me to go to the restaurant with this in?”

  “Yes, I do. I can put it in for you when I pick you up if you’d like.” The threat was light, and, to be honest, he wouldn’t mind lying her across his lap and inserting the plug before going out with her friends.

  “That’s okay. I’ll do it.” She patted his hand resting on her hip.

  “Good. You sure you don’t want to spend the night?”

  She let out another yawn. “No. Thanks, but I’d better get home soon.”

  He shook his head. “I could make you stay. I could order it.”

  She tensed again.

  “But I won’t.” He breathed out deeply. “You’ll take a cab, though. If you walk, I will blister your ass.”

  “It’s only—Ow!” She scooted away from him when his fingers pinched her tender bottom. “Okay! A cab.”

  “Good girl. Now let’s get the plug out so I can show you how to clean and store it.”

  Chapter 13

  A week crawled by as Jessica became used to having the plug in her bottom each night. At first, she thought the idea crazy, to place something in her ass…never. However, she found as the plug sank into her backside, she sensed Royce’s presence. More and more he invaded her private time. Not physically or even with demands, but he never drifted far from her mind.

  James had been the last man who had captured her attention in such a way, but even he didn’t consume her the way Royce did. The idea she might have deeper feelings for him struck her as she stepped into her apartment after work. No love. That’s what she had told him. Love isn’t something you plan, he had said.

  “No. Don’t go there. Everything is going fine. Don’t fuck it up with love.” She chastised herself as she threw her hair back in a ponytail. Royce would be picking her up any minute. It had taken a little longer to get the new plug in, as it was the largest of the set. As he did every day, he’d offered to come over to help her—but she declined. Her apartment was still too intimate. Especially with the way she was becoming addicted to him, she needed to keep some distance between them.

  Royce had just stepped onto the stairs of her building when she flew out the front door. Jokingly, he snapped his fingers. “Damn, almost made it all the way up.”

  She laughed. “Maybe next time,” she said, like she did every time he picked her up on her stoop.

  “It’s getting darker earlier now.
I don’t think I like you waiting outside for me.”

  “I wasn’t outside,” she countered, reaching the step above him and placing a soft kiss on his lips.

  “Semantics.” He linked his fingers with hers and gave her room to step down.

  A car door closed from the curb, and the woman stepping out of the cab caught Jessica’s eye. The blonde woman from the neighboring building stood in knee-high boots and a mini dress with only a light sweater over her shoulders. Her boyfriend, the man next door, flew down the steps of his building with a jacket in hand. After paying the cab he threw the jacket over her shoulders and said something in her ear. His expression was menacing, and the way her shoulders and eyes dropped after he spoke told Jessica he wasn’t pleased.

  She watched as they walked up to his apartment, the man continued to glare at her as she walked. If she had looked away, she would have missed it, but as her eyes were glued to the couple, she saw him deliver two hard swats to her ass just before they entered his building.

  “Jessica. You’re staring again,” Royce whispered in her ear.

  “Let’s go.” She pulled his hand and started down the street.

  “Wait.” Royce laughed. “It’s too cold for a walk. We’re going to take a cab.” As if the magical cab service had heard him, a taxi drove toward them. A quick wave of his hand, and the vehicle stopped at the curb.

  “I wonder why he was so mad.” Jessica zipped her purse and moved closer to Royce in the back seat.

  “I’m sure it had something to do with the way she was dressed and the weather.” He rested a hand on her knee. “It’s too cold for the outfit she was wearing.”