WINDY CITY: The complete series

by Stone, Measha

  "Is your pussy sensitive from the beating I gave it? How about your clit, from the two orgasms you had?" Her eyes widened at his questions. Switching gears on her threw her off balance, but also didn't give her time to worry about what was coming.

  "Yes, Sir." She brought her eyes to meet his without being told to do so, and his dick responded accordingly. He'd been hard since leaving the club. Having her close to him made him react.

  "Let's go upstairs to my room. It's late." He didn't attach her leash or give her any further instructions, he simply turned and walked away. After getting to the top of the stairs and turning down the hallway to his room, he noticed her behind him and smiled.

  Erin paused in the doorway of his main bedroom, looking around with awe. He'd taken over the master suite only a year ago, having felt weird about sleeping in his parents’ room at first. Before he did, he'd stripped them all down and had them redecorated to his liking. The mahogany paneled walls were replaced by deep maroon paint. He changed all the flowery bedding his mother insisted on to black silk, fully aware of the cliché, but he didn't give a damn. His tastes were simple.

  "Come kneel by the bed." He gripped her arm and pulled her forward. She slid down to her knees, looking up at him with a mixture of lust and surprise. "Do you remember how I told you everything I do will benefit us both, even if it doesn't seem like it? Well, this is one of those times. I want you to suck me off. You'll take my cock in your mouth and suck me until I come. I won't touch you, you won't come, especially since you didn't bother asking for the second orgasm at the club."

  "I…" His hand covered her mouth, stopping her from speaking.

  "I don't want your excuses." A little squeeze of his fingers, and she gifted him with a slight wince. He checked her expression for fear. None. At least not enough for him to lessen his grip. "You didn't ask, but that's okay." He released her cheeks and used the tip of his fingers to lightly slap her face. Her pupils dilated, and he grinned. This was going to be more fun than he'd imagined.

  He straightened to his full height and unzipped his pants. As he pushed aside his boxers, his cock sprung free. That alone gave him cause to groan in pleasure. He didn't usually bother with boxers when he played at the club. Easier to get to his dick without them, and he never fully undressed while in the dungeon, but he hadn't planned on pulling his dick out with Erin…not at the dungeon anyway.

  He wanted to show her the pleasure of pain, the enjoyment of giving over to him, and reward her for it. His reward was to use her like this. He may not let her come, but servicing him would fulfill a need inside her she didn't know existed. Yet.

  "Open your mouth, Erin." He stroked his cock in front of her face. If he moved even a breath closer, he'd be touching her. Beautifully, she opened her mouth. "Stick out your tongue," he ordered in a raspy voice. Again, pure obedience. "Good girl." He gripped the hair at the back of her head and brought her forward onto his cock. Slowly, he thrust into her mouth, more and more, until he touched the back of her throat. She sputtered, and he withdrew, letting her gasp a few breaths. "Keep your mouth open." He drove forward again, the heat of her tongue nearly undoing him. She let him lead, so he pulled her head toward him as he crept back into her mouth. He used both hands to grip her hair, moving her along his length, having her take him painfully deep.

  He withdrew, and she sucked in air. She kept her eyes on him as a tear dripped from her eye and rolled down her cheek. He caught it with his middle finger and brought it to his lips, licking it off with a smile.

  "So beautiful." He grabbed her and thrust into her mouth again. This time, she was ready and relaxed enough for him to move farther down her throat. "Ah, fuck, Erin."

  It didn't take much else to bring him to the brink. He'd been teetering for most of the night. Her eyes continued to stay on his while he watched his dick move in and out of her mouth. She suckled him, licked him, and took him as deeply as he pushed. He could go further, bring her face all the way to his groin, but he decided to keep that lesson for another night.

  "I'm going to come on your face and tits. Don't move and keep your mouth open." He pulled out and stroked his cock faster and harder until he came. She blinked in surprise as streams of semen sprayed across her chin and tongue and chest. Like the hungry girl she was, she wrapped her lips around his cock, licking him and suckling him until every drop had been milked.

  He pulled free and leaned against the bed. His breathing was ragged. His mind swirled. She was kneeling beside him, waiting for further instructions, but his body didn't care, he wasn't ready to move yet. He reached over to his nightstand and retrieved a washcloth he kept in the drawer, handing it to her.

  "It's time for bed." He managed to straighten and pull his pants all the way back up.

  After she wiped herself clean as best as she could, she got to her feet and looked at the door. "Which room should I use?" she asked, her voice soft, innocent.

  "This one." He turned his gaze on her. Why would he have her sleep anywhere else? He may use her body for his own enjoyment, but he wouldn't toss her aside like a common whore. Her eyes flickered to the door again, then back to him.

  "And you?" A softer voice.

  "Get in the bed, Erin." He sighed. He didn't have the energy to straighten out her wayward thinking. She'd drained him of all patience and power. She padded over to the bed, and he watched her, noting two red marks on her ass from his nails. "I'm going to change. The bathroom is through there if you need it, but do not leave this room otherwise. Do you understand?"

  "Yes, Sir." She nodded, yanking the thick comforter over her body. Her naked, lush body. He'd barely touched her. There were so many ways he wanted to feel her, nibble her, bite her. If she kept looking at him with her big brown eyes, he might want to keep her. And that wasn't a possibility.

  "I'll be back." And with that, he turned and walked to his closet, hiding like the ass he was until she fell asleep.

  Chapter 8

  As ominous as the bedroom had appeared the night before, it increased over night. Erin sat in the king-sized bed, with the luxurious sheets and a sinfully comfortable mattress, staring at the door. Bradley wasn't in the room. Had she not felt him climb into bed the night before and yank her across the massive space to haul her up to his side, she wouldn't have known he'd been there at all.

  Had she crossed some line? She'd been casual, aloof. She hadn't made any demands, and she’d done a pretty good job of following his lead. Especially since she hadn’t a clue as to what she was doing. Of course she had been disappointed when he chose to use only her mouth for his release. Her body ached to be touched and filled by him. Instead of trying to manipulate him into having sex with her, she'd done as she was told. Took the consequence for having that second orgasm—which she completely blamed him for, though she had no plans to bring that up.

  His fierce expression the night before hadn't terrified her; it excited her. The firmness of his voice, the harshness of his eyes—all of it had heightened her arousal. Thinking back on it made her wet again.

  He hadn't given her permission to leave the room yet, but she needed a little relief, just a bit. Trying to find some remedy for her condition, she closed her legs tightly, which only put more pressure on her wanting clit. She cursed into the empty room and threw the blankets back, heading for the bathroom.

  The cold water ran down her back as she lathered her legs. She would smell like his soap all day. Her hand brushed against her sex innocently enough…at first. Her fingers were soaked, and it had nothing to do with the water from the shower.

  She slid a finger into her entrance, toying with the rim before pushing hard into herself. She let her thumb press against her clit while she slid in a second finger, lifting her leg to rest on the small ledge of the shower. Her free hand found her breasts, tugging and twisting at her nipple while she continued to rock against her palm. She wouldn't come, she wouldn't disobey that rule, she just needed to take the edge off.

  "I don't think you understand
the rules." His deep voice penetrated through the sound of running water and her own moans.

  Shit! Now he shows up!

  "I wasn't going to finish," she blurted out before she even managed to slip her hand out from between her thighs. He watched her from behind the glass door, droplets of water running down in front of his face. Even with the distortion of the steam, she could make out his expression perfectly. Irritated.

  Well, damn!

  "You weren't going to finish." The dropped tone should have been a warning. She should have remembered his promise about being strict and unrelenting.

  He opened the shower door, reached behind her, and turned the water off. A few drops landed on his dark gray T-shirt.

  "You were going to do what exactly—bring yourself right to the edge and then deny yourself the pleasure?" His eyes narrowed on her.

  Finally remembering to move, she dropped her hand and stood straight up, one arm draped over her breasts, the other protectively covering her vagina. He'd seen and touched everything she was hiding only hours before, yet her cheeks burned beneath his intense stare. She had no embarrassment when begging to come under his hand, but him catching her pleasuring herself made her want to shrink down from his sight.

  "I asked you a question." His dark tone drew her full attention. His ability to keep her rooted to the floor with only his stare both aroused and infuriated her.

  "I don't know." Better to go with honesty. Her intentions had been to do just that—relieve some of the pressure—but she wouldn't deny her confidence at being able to stop before breaking his rule began to diminish.

  "Step out." He moved away from the door to give her room. The water dripping from her hair would have to be ignored. "First of all, you don't hide from me. Put your hands down." She dropped them to her sides, clenching and unclenching them. "Second of all, you never would have stopped. If I had stopped to check on your phone that keeps buzzing, I would have been too late. You would have come all over that hand of yours. You would have stolen another orgasm."

  Having such candid discussions about her orgasms was new territory for Erin. The most Jonathon ever did was acknowledge she'd had one so he could go ahead with his.

  "Tell me I'm wrong." The challenge was there. Lie or tell the truth. Her decision. It was the only power she had at the moment.

  "You're probably right." She met his gaze to gauge his reaction. His set jaw and dark eyes were her answer.

  "We are going to do a bit of discipline training today. But first, let's deal with this orgasm problem. Sit up here." He patted the long marble countertop lining the length of the bathroom.

  Her wet skin made it easier to ease onto the counter, but the slight flip of her stomach made looking at him more difficult. She kept her knees together and gripped the ledge with her hands on either side of her legs.

  "Open your legs." He stepped to her side, the rough denim of his jeans brushing her leg. "Is this what you wanted?" Two fingers thrust inside her, and she released the most unladylike grunt she'd ever heard herself give. "Push your pussy out for me." He looked down at her. No one ever looked at her there. "Roll your hips forward and push out your pussy." He withdrew his hand and slapped her inner thigh hard.

  She managed to do as he’d instructed before he brought his hand down again. With no delay, he thrust his fingers back into her. She gripped the counter tighter. She'd already been at the edge, and he quickly brought her back there. He could bring her to orgasm merely from staring at her, but she preferred his current method more. She chanced a look at his face. A firm set mouth, dark eyes, and raised eyebrows. She hadn't been looking at him, her eyes had been closed!

  "Now you're closing your eyes. You try to steal an orgasm, and now you're closing your eyes." He shook his head. "Not starting the day off very well, are you, Erin?"

  "No, Sir." She wanted to cry, to beg for him to forget what she'd done and start over. "I'm sorry, Sir," she breathed as he palmed her clit. So close, just a little further. "Can I come, Sir?" she asked, not even caring that she sounded so damn desperate. She'd gone to bed hungry, woken up ravenous, and now, with his touch, she couldn't deny herself any more.

  "No. You hold it. You said you were going to hold it, so you hold it." His lips thinned. He couldn't mean that, he couldn't be so cruel, to bring her so close and leave her dangling.

  "Please!" She slammed her palm against the countertop, using all of her power to keep her eyes steady with his. Closing her eyes now would be the dumbest thing she could do.

  "No." His lips were still thinned, but she could see the little wrinkles around his eyes. "Is this hard? Keeping your orgasm locked up?" he asked, putting more pressure on her clit with the heel of his hand. She screamed out at the deeper sensation. If she didn't come soon, she'd die.

  "Please. I'm sorry! I'm sorry!" She would have promised him almost anything at that moment.

  "Not yet." His second hand gripped her nipple. "You were playing with your tits. Do you like your nipples pinched?" She didn't need to answer. His fingers clasped around her hard, and the burn mingling with the building sensations in her cunt blurred the lines of reality. "Do you like that?"

  She shook her head in frustration. "Please! Please, may I come?"

  He locked eyes with her. She bit down on her lower lip until it numbed. She needed to get this right, to please him, to obey. It was the obedience that drove her arousal further. "Okay, now you can come. Don't look away. If you look away, you won't have another orgasm for the rest of the day. Do you understand me?"

  "Yes, Sir!" He released her nipple, and a new heat drove her over the edge, throwing her into the ecstasy she sought. She kept her eyes on him while she cried out with each harsh wave crashing through her body. His hand didn't slow; his thrusts didn't soften. He didn't just allow her to orgasm, he drove her through it, keeping his stare directed on her, making everything more profound.

  While she continued to gasp for air, his hand came up to her mouth and pushed past her lips. She'd never tasted herself before her first encounter with him, but it seemed to be a recurring thing with him.

  "Did you enjoy that?" He gripped her face. "What do you think you should say after I let you come?"

  "Thank you, Sir," she whispered, basking in the pleasure in his eyes.

  "There you go." He patted her face, then scooped her off the counter, carrying her from the bathroom to the bedroom, completely ignoring the fact that she was getting his clothes soaked.

  He dumped her on the bed and began to strip off his clothes. She lay back, propping herself up on her elbows as his shirt flew across the room. She'd seen his muscular arms the night before, but damn, she hadn’t been expecting him to look like that!

  His tattoo didn't just travel down his arm, it went over his shoulder and left pectoral. A wolf's head in a growling position covered his chest, melding into the rest of tattoo. How fitting. He looked every bit the predator when he stared at her the way he was now. His strong hands pulled at the leather belt around his waist. How would the belt compare to the flogger? The button was next, then he shoved the jeans over his hips and kicked them away. He was naked—gloriously naked—standing at the edge of the bed. His cock stood at complete attention, looking as delicious as she remembered. Giving blow jobs hadn't been her favorite past-time, but sucking on him could change that. His held such power over her.

  "New rule, you don't touch yourself without my permission. If you want to masturbate, you ask first." Grabbing her ankles, he yanked her to the edge of the bed. She swallowed, keeping her eyes on him as he moved to the nightstand. Jonathan had used condoms when they’d first starting having sex, and she remembered how clumsy he was. Bradley didn't do anything in a clumsy fashion.

  "Open your legs for me." He didn't wait for her to comply. He shoved her thighs open and grinned down at her. "Your pretty pussy is still wet, and not from the shower. I bet when I sink into you, I'm going to find you all hot and juicy." She wanted to look away, to move from his gaze.

 
; He climbed onto the bed, wrapping her legs around him. He toyed with her, running the head of his cock along her folds, easing into her entrance just enough for her to open to him before he pulled away. He placed his thumb over her sensitive clit and rolled it, pressing on it until she yelped. It hurt, in the best way possible, but still, it wasn't all pleasure. She figured he didn't want it that way.

  "Is your clit sensitive?" For a moment, she considered not answering—let him stew on it—but he put more pressure, increasing the sensation.

  "Yes, Sir!"

  "Good." He drove into her, finally filling her. He was larger than she remembered. She groaned and moved her hips, both to escape and to take him in further. Everything seemed like a contradiction with him.

  Bradley sunk in deep, then paused. His brow furrowed, and his lips pursed together. "You're so fucking tight," he growled, then began to move again, slow, calculated. Her body slowly adjusted to his size and the discomfort faded, leaving only the feeling of fullness she sought.

  He groaned, rolling his hips to thrust harder. His abs tensed as he continued to fuck her. Hard, fast thrusts followed by shallow, tortuous movements. She moaned: long, frustrated sounds. "Please." She gripped his shoulders and tried to push up at him.

  "I'm going to tie you down next time." Not a threat, just a warning of something new she would experience. "Don't close your eyes." He pinched the inside of her thigh.

  She yelped again. That particular rule was becoming more difficult to obey. She grasped for some self-control, but he had stolen it from her. Taken it, held it in his hands. She would have to wait for him to give it back. She could wait. She would show him she could do what he wanted, she could be his good girl. He grabbed her thighs, shoving them farther part, pushing them up toward her chest. He felt larger this way, too large. She winced. He didn't seem to mind her discomfort. In fact, he used his thumb again to roll her clit.

  Only this time, the discomfort turned quickly to heated desire. She wanted more of it, all of it. "What's going to happen if I keep doing this, keep playing with that little clit of yours?" he asked, his smile evident in his eyes.