Pushing Boundaries

Disclaimer: This is the first story I've written in many years. It was inspired by an actual lover and his interests. Please... Be gentle, but be honest! Feedback is appreciated.

Enjoy!

*****

She looked around the room one last time, taking a deep breath to calm her nervous jitters. Everything was exactly as he'd requested. The wine was decanted into a carafe, the ruby liquid catching the soft light and glowing from deep within. Two glasses were waiting next to the carafe. The white postal box with its ubiquitous blue and red stripes was waiting as well; its unknown contents the source of the worst of her nerves.

There was a small tray on the nightstand, its contents also arranged carefully according to his explicit wishes. No surprises there, though. All of the items were things he'd bought on previous visits, things he'd used to torment, titillate, tease and pleasure her... A small bottle of the lube he preferred, a silk mask, a small collection of dildos and vibrators, nipple clamps, leather cuffs, a small hairbrush paddle, and a towel.

She shot another nervous glance at the mysterious box on the table and with an effort of will, dismissed it from her thoughts. He would do as he pleased, and no matter how much she resisted, she knew she would, ultimately, submit to the pleasure of serving her man.

A quick look at the bedside clock sent her pulse into overdrive again. Fifteen minutes to 7. She had to be ready and waiting for him by 7, though she knew from experience his schedule often forced delays on him that he could not control. She shuddered slightly, remembering the last time he'd been delayed. His frustration and irritation had made the first moments of his visit tense and stressful as she'd struggled to please him.

She made a quick trip to the restroom, leaving her clothing folded neatly on the bathroom counter when she was done. She double checked the outfit hanging on the bathroom door and then reentered the bedroom to get ready for him. His instructions this time were slightly different than her usual instructions. Rather than meet him naked, kneeling at the door, he'd instructed her to assume a position on the bed and wait.

A stacked mound of pillows under her tummy raised her behind into the air, exposing her ass and pussy to the slightly cool air in the room. She shivered a little before her naked body grew used to the temperature, and she lay there, head pillowed on her arms, waiting for her man to arrive.

He walked quickly down the hall to the room where he knew she was waiting. He was late, much later than he'd expected, and he knew she'd been waiting for some time. He'd checked his watch in the elevator; 8:30. Not the latest he'd ever been, but the time felt like an eternity when he knew she was waiting for him.

He smiled slightly, the irritation at the delay nothing against the anticipation of what he had in store for her tonight. His pace picked up as he thought about her reaction to the new toy and the new plan and soon he was slipping his key card in the reader and entering the room.

The scent of the candle burning on the dresser caressed his senses first, the heady aroma of sandalwood and jasmine a balm to his senses. He smiled again, knowing that he should address this small act of independence, but since he liked that she continued to show spirit and a streak of individuality in thoughtful ways that only served his needs, he thought he'd continue to allow it.

A glance around the room showed that all was ready precisely according to his instructions. Good. She might show occasional bits of independence, but she also knew exactly how to please him and continued to surprise him with her attention to detail and anticipation of his desires.

He grinned as he noticed the lacy scrap of cheeky panty she'd included in her chosen outfit. She knew he loved her ass in those panties, and the hopefulness of the inclusion of that pair amused him. She much preferred the security of panties under her clothing and he much preferred her bare. Panties had their place, in his opinion, and it certainly wasn't under her dress.

Perhaps he'd add a reminder to her that his instructions were not negotiable; in spite of the amusement he felt at her attempt, he knew that she'd continue to push this point until he put a stop to it. Although he had a plan for her tonight, they had plenty of time and he could definitely fit corrective instruction into his activities for the evening.

He left his rolling bag at the side of the dresser and entered the room completely. His groin tightened as he took in the scene before him. He stroked himself absently through his trousers as he approached the bed where she lay waiting. As he suspected might happen, she'd dozed off waiting for him. But that wasn't an issue; he didn't mind if she'd relaxed enough to sleep. That meant her nerves had worn off and she'd be more responsive and comfortable. Tonight that would be more important than most visits.

Her lovely face was framed by her curls, her features soft with sleep. As always, her makeup was impeccable and tasteful, her luscious lips bare as instructed, pink and inviting. His groin tightened again painfully and he forced his thoughts away from those lips wrapped around his cock. He surveyed her position on the bed with approval. Her ass was raised invitingly, her legs spread slightly to bare her pussy and asshole to him. He was pleased to see the glistening wetness between her thighs; even given her nerves, her body betrayed her anticipation and need. He nodded slightly and turned to the table, pouring a glass of wine before he focused his attention on the box in front of him.

She awoke slowly, to a growing need. Her clit was throbbing with pleasure and her body thrumming with desire. She came fully awake suddenly, panic making her gasp, though she forced herself to remain still on the bed.

"You're awake. Finally," a mocking masculine voice said above her. She tensed briefly before she detected the amusement in the tone and relaxed.

"I'm sorry, sir. I did not intend to sleep. I will make any amends you require."

He gave in and laughed, "No, girl, you were lovely in your sleep, and you will need the nap for tonight's activities. I'm glad you were relaxed enough to sleep." She felt him move behind her as he spoke, then warm wetness spread across her ass and dripped down to coat her asshole and pussy.

Before she could wonder what he intended, she felt his finger stroke her asshole and she struggled briefly not to tense up. She was so afraid of the pain of anal play, but he loved it so much and he always made it pleasurable after the pain. He nodded in silent approval of her triumph over the struggle he knew she'd feel and pushed forward without speaking.

He slid his lube coated finger into her ass without hesitation, stroking her flesh fully once, twice, a third time before adding a second finger. She hissed softly as her asshole stretched around him, but she was used to this and waited for her body to accommodate his probing fingers. He stroked again, once, twice and on the third added his ring finger. He didn't even pause this time and continued to stretch her ass around his fingers. He could see her pussy responding to his ministrations, even if she was still struggling to be comfortable with the intrusion.

"That's my girl," he spoke encouragingly, knowing she would respond well to the praise. He needed her relaxed for this next part. She relaxed fully against his hand and allowed herself to accept the pleasure he was bringing to her. As he felt her relax, he slid his fingers in and out one more full stroke before pulling out completely and replacing them with the plug he'd retrieved from the box on the table.

He knew she'd have panicked if she'd seen it beforehand, which is why he'd sent it by mail and instructed her to leave it for him to open. Before her asshole could begin to tighten up again, he doused her with lube and pushed the huge plug against her ass. She took more than half its length before its girth was larger than he'd stretched her. She tensed up and moaned, trying hard not to beg him to stop. She knew he would if she really meant it and used her safeword, but she knew he would be tremendously disappointed. She also trusted him to know what she could take and so fought to relax again and allow him to do what he wanted to do.

He paused only momentarily as she struggled to accept the plug in her ass. He judged her struggle and then resumed the pressure on the plug into her ass. He could feel when she relaxed, and her sphincter softened slightly allowing the plug to stretch her to accommodate it.

He dripped lube on it again and with one last, steady push, shoved the plug's flare through the barrier of her sphincter. He felt it settle into place, her asshole immediately tightening around the neck of the plug, the base's jewel winking and gleaming in the soft light of the room. He smiled to see it; the pretty jewelry nestled in the thick flesh of her ass.

He wiped his hand on the towel and with a thoughtful frown, picked up the hairbrush paddle on the nightstand before dropping the towel back on the tray. He returned to his stance at the foot of the bed and spoke softly, "Girl, we have more to do tonight, and I am pleased that you did not resist me in this first thing. It is important to me, as you know, that your ass be trained and ready for me at all times, and this plug will be a good start to that goal. As always, I will have a photo for you of what we've done tonight, and in the future we will add this to the things you will do to be ready for me when I visit."

He paused and she replied immediately, "Yes, sir, thank you sir for helping me learn how to serve you."

He allowed a smile at her response to flit quickly across his features before the stern frown creased his forehead again. "Girl, you need to understand, though, that when I give you instructions, I expect them to be followed every time the way I've shown you. You are not to add or subtract from those instructions, even if what I want from you makes you uncomfortable. We will always be pushing your limits and discomfort is part of that process. I saw the panties you included with your dress for this evening, and you know that I do not allow panties under your clothing."

He watched her body slump in surrender and he knew she'd truly hoped her choice would be allowed. He nodded once and without another word, he swung the hairbrush paddle against her asscheek. She shrieked once, then bit the sound off with a sob, "I'm sorry, sir, it will not happen again." He struck her other cheek with the paddle and she jumped, her cheeks clenching with the pain, but she successfully smothered any cry of pain.

He proceeded to slap the paddle against each cheek in turn, giving her a full ten strokes on each cheek. By the end, her ass was red hot and swollen, ridges forming where the edges of the paddle caught her flesh. He knew she'd bruise and sit gingerly for a couple of days, but she really needed to understand that his word in this relationship was law.

Tears were running down her face and she sobbed silently as he finished, and she hiccupped slightly before she spoke, voice hoarse from the effort of holding her cries silently, "Thank you, sir, for helping me understand my error. I will not make the mistake again." He nodded and dropped the paddle on the nightstand and walked over to the chair by the table, dropping into it and picking up his wineglass. He gulped down a generous swallow, hoping the alcohol would help him control the raging hard on and he regarded her for a long moment before he said, "You're welcome, girl. Now get dressed and we will go for dinner."

She straightened slowly to her knees, wincing with pain, then stopped, hesitating before asking softly, "Sir, the plug... Will that stay?" His cock surged to hardness again as he realized her fear and he steadied himself. "Come here, girl. Get down off that bed and crawl to me." She got off the bed, avoiding sitting down, and dropped to her hands and knees and scrambled to kneel in front of him.

"Look at me," he growled.

She looked up, her lovely, tear streaked face troubled in the soft light. "That plug is going to stay in until I take it out. Do not question me again; I don't want to paddle you again so soon, but I will absolutely paddle you if you question me again." She nodded immediately, tears glistening again in her eyes, "Yes, sir. I am so sorry, sir." He picked up his wineglass in one hand and gestured at his very obviously tented trousers with the other. "Take care of this first, girl, then get yourself cleaned up and dressed. We have reservations."

She immediately reached for his pants, unbuttoning and unzipping them before reaching in and freeing his hard cock. She licked her lips once, then rose up on her knees and took him in her mouth. She suckled him hard, sliding those lips down his length until he was fully engulfed in her hungry depths, the head of his cock nudging the back of her throat.

He reached out and tangled his hand in her hair, pushing her face down hard. She gagged and coughed but took him, her hands moving to her lower back, clasping each other behind her back as she used her body's leverage to move her up and down his cock. He relaxed his pressure but didn't let go of her hair as she sucked hard on his cock, suckling to keep her drool from staining his trousers as she took him to full depth with each deep stroke.

He didn't even try to resist the pleasure of her lips and tongue on his flesh and with only a few strokes he groaned deeply and released himself into her throat, shoving her head down hard on him as he came. She swallowed frantically, taking him all, and as he finished, she suckled him softly as she came off his cock, making sure all his cum was cleaned up and swallowed and that any saliva was removed.

He let go of her hair and she sat up, lips and mouth red and swollen with the effort of sucking him off, a small drop of cum glistening on the corner of her mouth. He felt his flesh stir with desire again as her tongue came out and licked up the drop and he gestured over to the towel on the nightstand before taking a deep drink of wine.

She crawled over to the nightstand and retrieved the towel, the jewel in her red, swollen ass winking with every step and he smiled in anticipation of the rest of the evening. She returned, breasts swaying with her movements and cleaned him up with the towel. He flicked fingers at her and she turned to crawl to the bathroom and clean herself and get dressed. He smiled at the sight again, knowing she chose to crawl to the bathroom to make amends for her doubt with the best sight of his handiwork and he knew the rest of the night would be exactly as he'd planned.

******

He watched her avidly all during dinner. She was absolutely beautiful this evening; her dress was flattering and lovely, soft folds flowing around her legs, décolleté tastefully presented in its surplice neckline, diamond pendant on her discrete collar winking in the low light in the restaurant.

She'd repaired her makeup well and swept her hair up, but he could see that her eyes were still a little puffy and swollen. The evidence of her previous tears was not evident to anyone but him, and the sight made him yearn to see her cry again. There was something very lovely about her blue eyes filled with tears of helpless pleasure or helpless desire, and he hoped to see it again once they were alone in private.

But he had to admit her physical beauty was eclipsed by her struggle to sit comfortably. Again evident only to him, her infinitesimal movements to rest on her bruised, welted, sore ass and accommodate the jeweled plug stretching and filling her ass were threatening to make it very difficult for him to stand up... His cock was currently rock hard under the napkin in his lap and he was going to have to think of something to be able to get up from the table without the entire restaurant seeing the evidence of his desire for his girl.

He smiled at her discomfort as they finished their meal and with a superhuman effort of will, forced his flesh to obey as they stood to leave. She stood with slightly less than her usual grace, stiffness from her earlier punishment making her movements awkward to his eyes. She smiled tremulously at him and bowed her head slightly in deference, waiting for his lead. He touched her arm to indicate she should precede him and he fell into step just to her side and led her out of the restaurant, his hand firmly on her elbow.

They made their way back to the car, her steps growing easier as they walked. He'd parked toward the back of the lot on purpose, part of the next step of his plan. They reached the vehicle and she stopped by the passenger door, waiting for him as she'd been taught.

He paused, then pointed to the hood of the car, "Bend over the side of the car and raise your skirt for me."

To her credit, she hesitated only a second before complying, resting her torso on the car and reaching behind her to flip her skirt up, baring her legs and ass to him. He glanced around quickly to assure their privacy... There were a handful of cars nearby, but nothing so close that he wouldn't have notice if someone approached. Good. He smiled a little wickedly and waited, knowing she would get antsy if what he planned didn't happen - and end - quickly.

True to form, as he watched, she started to fidget slightly, making the jewel still in her ass jump and wiggle as her muscles clenched around it. He watched her force her flesh to relax, and he knew she was hoping he'd remove the jewel. He laughed to himself at the thought; no, she'd be wearing that jewel for some time yet.

Finally he walked up behind her and without touching her anywhere else, he took one finger and traced the welts on her ass, the bruising starting to form around them. He pushed lightly against the largest welt, making her jump slightly, then removed his hand completely, pausing before he reached out and cupped her pussy with his hand. His hand was immediately soaked with her juices and he leaned forward, using two fingers to pinch her clit, hard.

"So you want me, do you, girl? After I beat you, after I filled your ass, after I forced you to go bare under your dress? You still want me to fill that pussy with my cock and my cum, don't you?"

She whimpered at the harsh tone of his voice and nodded, "Yes, sir. I am yours to do whatever you please. Your pleasure is my desire."

He let her clit go and she moaned softly as it throbbed as the blood rushed back to the abused flesh. "Good girl. Remember that, and maybe you won't have to sit through another dinner with a bruised ass."

He slapped the bruised flesh, making her clench her teeth and moan, but her body betrayed her desire, her back arching and baring her pussy more fully to him. He looked around again and unzipped his trousers. He'd need to release himself again if he were going to last the rest of this night.

He stroked his hot, hard flesh once before leaning over her again, "If you cum without permission, girl, I will paddle your ass again and you will end this night without another release and you will go without release until I'm in town again."

She whimpered again and nodded, "Yes sir."

He nodded and resumed his position behind her, then in one full, hard thrust, shoved himself fully inside her, sheathing himself to the hilt in her wet, hot, tight depths. He reached around once and pinched her clit again, hard, twisting it cruelly before letting it go.

He could feel her tense around him, struggling not to cum, and satisfied she'd control herself, he slid himself almost all the way out and then slammed back into her. She grunted as the plug was pushed farther into her, but pushed back against him to take him deeper. He responded by slapping her ass again, then stroked himself hard in and out of her again, feeling his balls tighten in response. One more good, hard, stroke and he shoved himself deeply in her and came, filling her pussy with his cum.