Reversal Rings One Night
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Role Reversal - Part 1 free porn video
Getting promoted to VP of finance at thirty-five had been Brett Andersen's dream. He had a gorgeous apartment filled with designer furnishings, a BMW convertible and a closetful of bespoke suits. Of course, he'd worked his ass off to attain that dream. And along with the dream came stress. Lots of it. Late nights, weekends, tight deadlines all meant that he needed a way to blow of steam. He ate well and went to the gym with what little spare time he had; he'd even tried meditation. But still, some days he felt like his head was going to explode.
There was no girlfriend in the picture. He didn't have the time, and what woman wanted a partner who was never available anyway? He had no trouble finding women to fuck; his tall, lanky frame and dimpled smile attracted them like moths to a flame. But that's all it was: a fuck. One time, and on to the next one. One and done, he liked to joke.
He kept to himself at work. He had few friends and didn't trust easily. His personal life wasn't up for discussion. He'd come too far to have everything ruined by office gossip and speculation.
The only person he really respected and trusted—mainly because he had no other choice—was his assistant, Kate. She had proven herself to be professional and competent and, like him, kept to herself. She didn't run out for lunch with the other assistants to bitch about work and spread stories about who was cheating on his wife and who was next to get canned.
“Rough day, huh?” Kate smiled sympathetically as she laid a packet of papers on his desk.
“Eh. The usual.” He didn't bother looking up, and she knew better than to linger. He heard the door click closed and sighed.
Glancing at the clock, he saw that it was nine fifteen. He dialed Kate's extension and told her to go home. He appreciated her loyalty and work ethic, but she didn't make what he did, and he saw no reason for her to spend all night in the office.
His head was pounding, and soon he found it almost impossible to concentrate. There was one thing that he would help with that. Usually he waited until he got home, but he was physically and mentally exhausted, and he knew the office would be empty by now. Leaning back in his chair, he reached down and popped the button on his pants, then yanked the zipper down. He sighed as his fingers met slippery satin.
Spreading his legs, he slid his hand further inside, rubbing over the hard bulge encased in whisper-soft peau de soie. Pink cheekies, with frothy red lace trim. They were new. He'd seen them online, where he did all of his shopping for this sort of thing, and had had to have them.
The tip of his cock peeked out from the waistband, holding it away from his taut stomach. Dark pubic hair curled around the edges of the delicate lingerie. He moaned as he reached inside and grasped his throbbing cock.
Eyes closed, head tilted back on the smooth leather headrest of his chair, he'd barely started stroking when the door to his office swung open and Kate was standing there, looking remarkably composed.
From that moment, things seemed to happen in slow motion. He froze with his hand on his dick, then hurried to cover himself. Fumbling with his fly, he pulled his shirttails over his crotch, then noticed Kate still standing there, watching impassively.
“Get the fuck out!” he barked. His heart thumped in panic. He cursed himself for not locking his door.
Instead, she closed the door and moved to stand directly in front of his desk.
“You're fired. Get the fuck out, now.” Fuck, fuck, fuck, he thought in a panic. The best assistant I've ever had. How am I going to explain letting her go?
She showed no emotion as she sat on the corner of the large mahogany desk, one slim leg crossed over the other.
“Fired? For what reason? That I walked in on you jerking off in a pair of panties that probably cost what I make in a week?”
His face reddened with fury and shame. “Kate, don't say another word and I'll make sure you get a generous severance package. You can quit, I'll make it worth your while— ˮ
She shrugged. “I like my job. Why should I quit? Besides, me disappearing suddenly would only be fodder for the rumor mill. You know I hate gossip as much as you do. You are I work well together. I think we'd work well together in other ways, too.”
He glared at her, incredulous. “Are you trying to blackmail me?”
She smiled. “Not my style. Look, there's nothing to be embarrassed about here. In fact, I'm not even surprised, really.”
He stared at her, stone-faced.
“You're a very busy executive with high-stress job. You put in long hours, don't socialize much... you need a release, something that takes you away from all that. Don't you?”
When Brett failed to reply, Kate leaned in and grabbed his Hermes tie, twisting it around her fist. “I asked you a question. It's rude not to answer. You need that, don't you, Brett?”
He'd always known Kate to be efficient and do what was necessary to get the job done. She was quick to chastise an intern she caught slacking off and could be quite cutting. But she'd never spoken to him like this. Who the hell did she think she was?
She tightened her grip on his tie, moving her fist up until it touched his Adam's apple and was uncomfortably tight against his throat. “Answer, you rude little prick.”
Brett's cock stirred at her tone. His breathing was shallow. “Y-yes.”
“Yes, what?”
He closed his eyes, turned on and terrified of where this was going. “Yes, I need that.”
Kate loosened her hold on his tie just a bit. “Good. Now, just to be clear, what exactly is it you need? To be wearing something pretty under that three thousand dollar suit? To be dressed like a slut, treated like the dirty little pervert you are?”
Fuck. He'd gone this far...This was something he'd fantasized about and wanted for years, but never had the balls to go after. Here was a woman who not only didn't judge him, but could give him everything he fantasized about and more. It was being offered to him, and he was going to take it.
“Y-yes, Mistress. I want that. All of it.”
A pleased smile crossed Kate's face.
“Good. But none of that 'Mistress' nonsense. You'll call me by my name. You'll soon see that I don't need a silly title to have you on your knees, begging to be treated like the dog that you are. And it eliminates any chance of an embarrassing slip-up.
“Now, since your pathetic cock is undoubtedly still hard, I want you to finish what you were doing when I walked in.”
Brett narrowed his eyes. He'd never shared this part of himself with anyone before.
Kate sighed. “Look. If you want this, this is your one and only chance. I don't waste time on pussies who can't own up to what they want. If you're concerned about anyone finding out, don't be. They won't. What happens between us will be strictly confidential. As far as anyone knows, I'm your assistant—that's it. You don't think you're the first man I've done this with, do you?”
Brett flushed, but didn't answer. His embarrassment grew when Kate laughed.
“Oh, my. You wouldn't believe how many men in your position want to go home and stop being the boss and start taking orders. Men in higher positions than yours, too. So stop worrying. We'll move slowly at a pace you're comfortable with. There won't be any pictures or anything of that nature until we've established trust. We'll get there. Now, start jacking that dick. I want to get home.”
She stared pointedly at his crotch until Brett took his cock in hand and resumed stroking. The cool satin cupping his balls, combined with the intense humiliation of being ordered to touch himself like this had him coming all over his hand in mere moments.
“Fuck.” He hadn't come so hard in a long time. The satin of his panties was stained a dark pink.
“I hope you enjoyed that, because from now on you won't come unless I give you permission. There will be consequences if you do. Oh, and when you do”— Kate smiled slyly—“you'll be cleaning up your mess.”
Brett gave her a questioning look, which soon turned to one of disgust.
“Lick it up.”
She gave him a hard look, and he raised his hand to his lips. As much as hated the act, he loved the thrill of arousal it sent through him. He licked the cum from his fingers until Kate purred, “Good boy."
Now, get dressed and go home. Make sure you wear something pretty for me tomorrow. Call me as soon as you get in and show me. Do you understand?”
“Yes, Kate. I understand.”
“Good.” She smiled. “You may have thought it bad luck that I walked in on you, but I think it's turned out to be rather fortuitous after all, don't you?”
…
The next morning he jolted awake, his stomach roiling with the memory of the night before. Fuck—had that really happened? His sense of trepidation was eased somewhat by recalling how turned on he'd been. How badly he'd wanted more.
As he stepped into the shower, his hand automatically went to his cock and he began lazily stroking, until Kate's words popped into his mind. He released his aching cock with a groan, washing quickly and wrapping a towel around his waist as he headed for his walk-in closet.
He reached up for a box tucked high out of sight. Laying it on the bed, he opened it and started rifling through the collection of expensive panties he'd amassed, his heart beating a little faster as he selected a pair, knowing he'd be showing them off for the first time very soon.
As he slipped them on, he wondered what Kate might expect of him. He'd never gone beyond wearing panties, except in his fantasies, but the thought of more excited him. Would she demand that he wear stockings, a bra? He knew Kate well enough to know that she was trustworthy. Even if this didn't work out, he trusted that his secret was safe with her.
He was uncomfortably hard as he drove to the office. His heart began to race as the elevator opened on his floor. Kate was sitting at her desk, looking as she did every other day—silk blouse, pencil skirt, heels, dark hair piled on her head in a twist. She smiled as he passed.
“Good morning, Mr. Andersen.”
He gave a curt nod. “I need to see you in my office, please, Kate.”
He closed the door behind him, and sat at his desk. Memories of last night rushed in. He took a deep breath when he heard a knock at his door.
“Come in.”
Kate entered. The room was silent except for the sound of the door clicking shut.
Brett wasn't sure where to begin. The balance of power had shifted last night.
“We need to be clear about how this will work,” he began in a clipped tone. “During business hours, our relationship will be as it always has been. I won't let this affect my job or reputation.”
“Of course.” Kate's expression gave nothing away.
“If we need to discuss something pertaining to our agreement, it will be done after hours.”
Kate nodded. “Agreed. But with all due respect, I told you last night I wanted to see what you'd put on for me. The door is locked. Be a good girl and let me see your panties.”
Brett swallowed hard. Be a good girl. The humiliation of having his masculinity stripped away with a few words made his cock throb. He stood and lowered his zipper, revealing a white lace thong.
“Ah, a thong. Very nice. Lower your pants, turn and bend.”
Cursing his choice, Brett did as he was told. He shuddered as Kate passed her small hand over his buttocks, running one finger along his crack before snapping the string that was wedged there.
“I'm pleased with your choice. Brave and sexy.” She slapped his ass. “Straighten up and pull yourself together.”
Brett ran a shaking hand through his hair as he did so. He sat, a hot blush still burning in his cheeks.
Kate smiled sweetly. “Will there be anything else, Mr. Andersen?”
“No. I don't want to be disturbed for the rest of the morning. Hold my calls.” He shuffled a stack of papers, refusing to meet Kate's eyes.
She didn't leave, though. Stepping closer, she leaned over his desk, and with two fingers under his chin, raised his head until he was looking at her.
“Just one more thing, and then I will adhere to our agreement. Since you'll be behind closed doors all morning, I want you to go online and order a cock cage. Stainless steel, not that plastic crap. You have my home email. Forward the order confirmation to me so I know you've done as you were told.”
She walked to the door, then turned and raised an eyebrow. “Not that I expect you won't.”
...
Later that morning, Brett forwarded the confirmation email as Kate had requested. He imagined her hands on his limp cock, stuffing it into the unforgiving metal of the cock cage for—an hour? A day? He shivered, wondering if it would be used for punishment or become a part of his daily routine. Despite a bit of apprehension, he was incredibly aroused at the thought of submitting to her.
It was something he'd been aware of for a while, although he'd discovered the many facets of his kink over time. He'd always loved strong women; it turned him on to no end when a woman took the reins in the bedroom. Through one particularly kinky and open-minded girlfriend he'd learned how much humiliation, in particular feminization, turned him on.
She'd discovered his panty fetish, and had used toys on him. That relationship had ended after a few months, but it left him with an intense desire for more. No other woman had been so open-minded, and he'd kept his predilections to himself. Until now.
He was still figuring out what really did it for him. He'd been in chat rooms, watched porn. What really got him going was the mind-fuck; having someone describe all the humiliating, dirty things they'd like to do to and with him. With Kate, he could be himself and explore all the things that made his cock hard. He could let go and truly submit.
He tried to put Kate out of his mind by busying himself with work. A brisk knock on his door made him look up. Glancing at the clock, he was surprised to see that it was already six o'clock.
“Come in.”
Kate entered and closed the door behind her. She took a seat in front of his desk, hands folded primly in her lap. “Do you need anything else tonight, Mr. Andersen?”
“No, I think we're good. Go home, enjoy the rest of your evening, Kate.”
“All right then. Since it is after business hours, though...”
He looked up, his stomach flipping. “Yes?”
“ 'Yes, Kate', but we'll work on that. I just want to establish a bit of a routine for us. From now on, you can send me a photo of the panties you intend to wear each day, and I will either approve or tell you to find something else. Or you can take your chances and show me when you get to the office.”
“Take my chances?” He repeated dubiously.
“Yes. If I don't like what you've chosen for that day, I may tell you to take them off and carry them in your pocket for the rest of the day. I may tell you to go out and buy something new. Or I may send you into the men's room to take a piss at the urinal in them.”
He shook his head. “We agreed; nothing that can impact my personal or professional life, Kate.”
She smiled. “Well, then... what is the answer here?”
“I'll send you a photo of the panties. Not on me, of course.”
“Of course... we'll get there, but not yet. I told you I wouldn't do anything to jeopardize you, and I meant it. But there do have to be consequences. So if you forget, or don't have time, or whatever other pathetic excuse you come up with, you know what they will be.”
Fuck. He'd be getting up extra early and making sure he got Kate's approval.
“Yes, Kate.”
“That's a good boy. One other thing. I want you at my place this Saturday at seven o'clock. Bring the cock cage, put on a pair of your prettiest panties and make sure your cock, balls and ass crack are shaved or waxed bare. Can you handle that?”
He felt the now-familiar blush rising in his cheeks.
“Yes, Kate.”
…
Saturday morning, Brett drove to a very high-end lingerie boutique two towns away. He selected a ridiculously expensive pair of red lace cheekies for later that night. His balls ached as he wondered what Kate would think of them. Whether he got her approval or a punishment, he was sure he would enjoy it.
Later that night, he carefully showered and shaved as he'd been instructed. Looking down at himself, he felt exposed, embarrassed; which was undoubtedly how Kate had meant for him to feel. The red cheekies felt exquisite against his bare skin, making him groan as he adjusted his cock. A final check in the mirror and he was off.
His mind drifted as he drove. His body was tense with anticipation. Could Kate be what he'd been looking for? Up until now, he'd satisfied his cravings for humiliation and submission with online chat and porn. How far would Kate push him? How far was he willing to go?
He pulled into the driveway of Kate's small, well-kept Cape. Grabbing the package containing the cock cage off the passenger seat, he got out and strode toward her front door, his heart pounding.
“Come on in, Brett.” Kate held the door open, ushering him in. Her use of his first name didn't seem out of place tonight.
“Thank you, Kate.” Brett found it easy to slip into submissive mode with her, despite their roles at work. Kate was a beautiful, strong woman. Her long, dark hair and cat-like green eyes lent her a touch of exoticism. He was eager and willing to bow down to her.
She took the package from him. “That's for later. Let's eat and talk about any questions or concerns you have. Anything, really, pertaining to our arrangement.”
He followed her into the kitchen. There were several containers of takeout on the center island. Kate handed him a dinner plate.
“Help yourself. I took the liberty of ordering for both of us. I know what you like.” She shot him a cheeky grin.
It was true, though. She ordered his lunch and sometimes dinner almost every day. She knew more about what he liked than probably anyone.
They took their plates into the living room. The furnishings were modern, neat and spare with splashes of bold color.
He followed her lead and sat on the overstuffed sectional in the middle of the room.They began to eat, making polite small talk until Kate delicately wiped her mouth and set her plate on the coffee table.
“So. How are you feeling about tonight?”
Brett considered her question. He was buzzing with nervous energy, horny as fuck, eager, scared.
“I feel ready.”
Kate smiled. “That's a good answer. This is something I sense you've wanted for a long time, and have done without, for various reasons. I'm glad to hear that you're ready now.
"I asked you to do several things tonight. I'm going to assume that you've done them. If I find otherwise, we'll deal with it in an appropriate fashion. Now, we should talk about limits. I don't want to do anything that crosses a line. We all have them.”
He thought about it. He had little actual experience exploring his kinks. But his fantasies sometimes took him to places that scared him. The more extreme the fantasy, the more it turned him on. Still, there were some things he was pretty sure he had no interest in.
“Scat, blood, anything that would leave visible or permanent marks...”
“All reasonable, and all things that I agree with. I know you have an interest in humiliation. Are there any subjects that are off limits? Things that might be triggering?”
He thought about it. It wasn't something he had a lot of experience with, but he loved the warm rush of embarrassment he felt looking at himself in a pair of panties, or imagining being bent over his bed and fucked. He wanted more of it.
“I don't know. I don't think so. Can we play it by ear and I'll let you know if something is too much?”
“That's fine. You're probably familiar with the stoplight system. Red if you need me to stop immediately, green if you're okay and want to keep going, and yellow if you need to slow things down a bit, but not stop.”
“And what about pain? Do you crave it, hate it, what kind of tolerance do you have for it?”
He thought of being being bent over naked, Kate's hand coming down on his buttocks again and again. Being paddled, flogged. His pants were getting uncomfortable tight.
“Again, I like it, but I'm not sure how far I'd be willing to go.”
“Okay.” Kate stood and picked up their plates. “We won't get through all of that tonight, of course. But it's stuff I need to know. And nothing is set in stone. At some point I'll be pushing those limits, and they'll probably change along the way.
"My bedroom is down the hall on the left. Undress except for panties, stand beside the bed, and wait. I'll be right in.”
Brett blew out a breath, then headed for the bedroom. Once there, he unbuttoned his pants with trembling fingers. He lowered the zipper, revealing the fine red lace underneath. He removed the rest of his clothes and stood beside the large four poster bed. The room was chilly, the cool air making his nipples pebble.
A few minutes went by before Kate returned. He was somewhat surprised to see that she was still wearing the tight jeans and blouse she'd greeted him in. It must have shown on his face.
“Expecting leather? Whips, thigh-high boots? Don't worry—once we get started, you won't be concerned with my outfit.”
She stepped closer, looking him up and down. “However... your outfit, such as it is, is a matter of concern.”
She twirled her index finger impatiently. Brett felt himself blushing as he turned, feeling Kate's scrutiny.
“Very nice, actually. Something I'd buy myself. Take them off and let me see if you've followed the rest of my instructions.”
He did so, his dick hanging limp and small from his hairless groin. She reached out, giving it a quick stroke, lightly caressing his balls.
“Good. Turn and bend.”
A mixture of humiliation and arousal washed over him as he bent at the waist. Kate palmed his firm buttocks before parting them.
“You appear to be eager to please. That's good. You won't want to displease me.”
She gave his ass a sharp smack. “Stand and face me.”
He did, and although he had at least eight inches on her, her unwavering stare made him feel small.
“You are to keep yourself clean-shaven and ready for me at all times. We've gone over the rules for what you are to wear to work. The same goes for the weekend. To start, we'll meet at least once every other weekend. If something comes up, you are to let me know right away so that I can reschedule our time together. There are no sick days, or personal days, or whatever. Unless there is a major conflict, I expect to see you here or wherever else I decide to meet, on time, and according to whatever rules I have set for that particular meeting. Do you understand?”
He nodded. “Yes.”
“Yes, what?”
“Yes, Kate.”
“Always use respect when addressing me. At work, you are Brett, or Mr. Andersen. When we're together, you'll answer to whatever I feel like calling you—bitch, slut, my good boy, good girl, whatever.”
She took his cock in her hand and stroked it to semi-hardness. His eyes fluttered closed and he swallowed hard, wanting so badly to come, willing Kate to keep going, stroke just a little harder...
Abruptly she stopped. “Now go and get your cock cage before this becomes a problem.” She waved him away.
Brett wanted to cry with frustration at the thought of being locked up, unable to get a release until... who knew? But it also thrilled him to know that Kate held it all in her hands. She would decide when and how he came.
He brought the bag with the cage to her. He watched as she removed it from its box, taking it into the bathroom to wash it before coming to stand before him.
“Today is Saturday. Because this is all new, I am only requiring that you wear it until Monday evening. You can shower and use the toilet with it on. The only thing you can't do, of course, is come.”
Her smile was cold and a bit cruel. “You can go forty-eight hours without yanking on that sad little cock, can't you?”
“Yes, Kate.” He hoped he sounded more confident than he felt.
“Of course you can. You don't have any choice, do you?” She slid the cool metal cage onto his cock. He winced as she closed the cock ring around his balls, slipped a small padlock on and locked it, pocketing the tiny key.
“Imagine if I happened to misplace this.” Brett's eyes widened in alarm. She winked.
“Well.” She grabbed her phone off the bedside table. “It's almost ten. We'll call it a night. I'll see you Monday; in the event of an emergency, you can call me, but don't dare waste my time to whine about wanting to come or how uncomfortable you are. I don't care and it'll cost you.”
She strode toward the door, leaving Brett standing naked and feeling a little left behind. This was it? She'd locked him in chastity and was sending him home?
She addressed him as one would a child. “Get dressed. Go home. We'll talk on Monday.”
He pulled his clothes on, careful to stretch his panties over the unfamiliar bulk of the cock cage. He headed out to the living room, where Kate was waiting by the door.
Her smile this time was kind. “This was a good start. Remember to be respectful, honest, and do as you're told, and this will be a good thing. This will be a really good thing.”
She opened the door for him. “Enjoy the rest of your weekend, sub.”
Her words made the hair on his arms stand up. He nodded, his throat suddenly feeling tight. As he walked to his car, he felt free in a way he never had before and eager to offer his submission at last.
There was no girlfriend in the picture. He didn't have the time, and what woman wanted a partner who was never available anyway? He had no trouble finding women to fuck; his tall, lanky frame and dimpled smile attracted them like moths to a flame. But that's all it was: a fuck. One time, and on to the next one. One and done, he liked to joke.
He kept to himself at work. He had few friends and didn't trust easily. His personal life wasn't up for discussion. He'd come too far to have everything ruined by office gossip and speculation.
The only person he really respected and trusted—mainly because he had no other choice—was his assistant, Kate. She had proven herself to be professional and competent and, like him, kept to herself. She didn't run out for lunch with the other assistants to bitch about work and spread stories about who was cheating on his wife and who was next to get canned.
“Rough day, huh?” Kate smiled sympathetically as she laid a packet of papers on his desk.
“Eh. The usual.” He didn't bother looking up, and she knew better than to linger. He heard the door click closed and sighed.
Glancing at the clock, he saw that it was nine fifteen. He dialed Kate's extension and told her to go home. He appreciated her loyalty and work ethic, but she didn't make what he did, and he saw no reason for her to spend all night in the office.
His head was pounding, and soon he found it almost impossible to concentrate. There was one thing that he would help with that. Usually he waited until he got home, but he was physically and mentally exhausted, and he knew the office would be empty by now. Leaning back in his chair, he reached down and popped the button on his pants, then yanked the zipper down. He sighed as his fingers met slippery satin.
Spreading his legs, he slid his hand further inside, rubbing over the hard bulge encased in whisper-soft peau de soie. Pink cheekies, with frothy red lace trim. They were new. He'd seen them online, where he did all of his shopping for this sort of thing, and had had to have them.
The tip of his cock peeked out from the waistband, holding it away from his taut stomach. Dark pubic hair curled around the edges of the delicate lingerie. He moaned as he reached inside and grasped his throbbing cock.
Eyes closed, head tilted back on the smooth leather headrest of his chair, he'd barely started stroking when the door to his office swung open and Kate was standing there, looking remarkably composed.
From that moment, things seemed to happen in slow motion. He froze with his hand on his dick, then hurried to cover himself. Fumbling with his fly, he pulled his shirttails over his crotch, then noticed Kate still standing there, watching impassively.
“Get the fuck out!” he barked. His heart thumped in panic. He cursed himself for not locking his door.
Instead, she closed the door and moved to stand directly in front of his desk.
“You're fired. Get the fuck out, now.” Fuck, fuck, fuck, he thought in a panic. The best assistant I've ever had. How am I going to explain letting her go?
She showed no emotion as she sat on the corner of the large mahogany desk, one slim leg crossed over the other.
“Fired? For what reason? That I walked in on you jerking off in a pair of panties that probably cost what I make in a week?”
His face reddened with fury and shame. “Kate, don't say another word and I'll make sure you get a generous severance package. You can quit, I'll make it worth your while— ˮ
She shrugged. “I like my job. Why should I quit? Besides, me disappearing suddenly would only be fodder for the rumor mill. You know I hate gossip as much as you do. You are I work well together. I think we'd work well together in other ways, too.”
He glared at her, incredulous. “Are you trying to blackmail me?”
She smiled. “Not my style. Look, there's nothing to be embarrassed about here. In fact, I'm not even surprised, really.”
He stared at her, stone-faced.
“You're a very busy executive with high-stress job. You put in long hours, don't socialize much... you need a release, something that takes you away from all that. Don't you?”
When Brett failed to reply, Kate leaned in and grabbed his Hermes tie, twisting it around her fist. “I asked you a question. It's rude not to answer. You need that, don't you, Brett?”
He'd always known Kate to be efficient and do what was necessary to get the job done. She was quick to chastise an intern she caught slacking off and could be quite cutting. But she'd never spoken to him like this. Who the hell did she think she was?
She tightened her grip on his tie, moving her fist up until it touched his Adam's apple and was uncomfortably tight against his throat. “Answer, you rude little prick.”
Brett's cock stirred at her tone. His breathing was shallow. “Y-yes.”
“Yes, what?”
He closed his eyes, turned on and terrified of where this was going. “Yes, I need that.”
Kate loosened her hold on his tie just a bit. “Good. Now, just to be clear, what exactly is it you need? To be wearing something pretty under that three thousand dollar suit? To be dressed like a slut, treated like the dirty little pervert you are?”
Fuck. He'd gone this far...This was something he'd fantasized about and wanted for years, but never had the balls to go after. Here was a woman who not only didn't judge him, but could give him everything he fantasized about and more. It was being offered to him, and he was going to take it.
“Y-yes, Mistress. I want that. All of it.”
A pleased smile crossed Kate's face.
“Good. But none of that 'Mistress' nonsense. You'll call me by my name. You'll soon see that I don't need a silly title to have you on your knees, begging to be treated like the dog that you are. And it eliminates any chance of an embarrassing slip-up.
“Now, since your pathetic cock is undoubtedly still hard, I want you to finish what you were doing when I walked in.”
Brett narrowed his eyes. He'd never shared this part of himself with anyone before.
Kate sighed. “Look. If you want this, this is your one and only chance. I don't waste time on pussies who can't own up to what they want. If you're concerned about anyone finding out, don't be. They won't. What happens between us will be strictly confidential. As far as anyone knows, I'm your assistant—that's it. You don't think you're the first man I've done this with, do you?”
Brett flushed, but didn't answer. His embarrassment grew when Kate laughed.
“Oh, my. You wouldn't believe how many men in your position want to go home and stop being the boss and start taking orders. Men in higher positions than yours, too. So stop worrying. We'll move slowly at a pace you're comfortable with. There won't be any pictures or anything of that nature until we've established trust. We'll get there. Now, start jacking that dick. I want to get home.”
She stared pointedly at his crotch until Brett took his cock in hand and resumed stroking. The cool satin cupping his balls, combined with the intense humiliation of being ordered to touch himself like this had him coming all over his hand in mere moments.
“Fuck.” He hadn't come so hard in a long time. The satin of his panties was stained a dark pink.
“I hope you enjoyed that, because from now on you won't come unless I give you permission. There will be consequences if you do. Oh, and when you do”— Kate smiled slyly—“you'll be cleaning up your mess.”
Brett gave her a questioning look, which soon turned to one of disgust.
“Lick it up.”
She gave him a hard look, and he raised his hand to his lips. As much as hated the act, he loved the thrill of arousal it sent through him. He licked the cum from his fingers until Kate purred, “Good boy."
Now, get dressed and go home. Make sure you wear something pretty for me tomorrow. Call me as soon as you get in and show me. Do you understand?”
“Yes, Kate. I understand.”
“Good.” She smiled. “You may have thought it bad luck that I walked in on you, but I think it's turned out to be rather fortuitous after all, don't you?”
…
The next morning he jolted awake, his stomach roiling with the memory of the night before. Fuck—had that really happened? His sense of trepidation was eased somewhat by recalling how turned on he'd been. How badly he'd wanted more.
As he stepped into the shower, his hand automatically went to his cock and he began lazily stroking, until Kate's words popped into his mind. He released his aching cock with a groan, washing quickly and wrapping a towel around his waist as he headed for his walk-in closet.
He reached up for a box tucked high out of sight. Laying it on the bed, he opened it and started rifling through the collection of expensive panties he'd amassed, his heart beating a little faster as he selected a pair, knowing he'd be showing them off for the first time very soon.
As he slipped them on, he wondered what Kate might expect of him. He'd never gone beyond wearing panties, except in his fantasies, but the thought of more excited him. Would she demand that he wear stockings, a bra? He knew Kate well enough to know that she was trustworthy. Even if this didn't work out, he trusted that his secret was safe with her.
He was uncomfortably hard as he drove to the office. His heart began to race as the elevator opened on his floor. Kate was sitting at her desk, looking as she did every other day—silk blouse, pencil skirt, heels, dark hair piled on her head in a twist. She smiled as he passed.
“Good morning, Mr. Andersen.”
He gave a curt nod. “I need to see you in my office, please, Kate.”
He closed the door behind him, and sat at his desk. Memories of last night rushed in. He took a deep breath when he heard a knock at his door.
“Come in.”
Kate entered. The room was silent except for the sound of the door clicking shut.
Brett wasn't sure where to begin. The balance of power had shifted last night.
“We need to be clear about how this will work,” he began in a clipped tone. “During business hours, our relationship will be as it always has been. I won't let this affect my job or reputation.”
“Of course.” Kate's expression gave nothing away.
“If we need to discuss something pertaining to our agreement, it will be done after hours.”
Kate nodded. “Agreed. But with all due respect, I told you last night I wanted to see what you'd put on for me. The door is locked. Be a good girl and let me see your panties.”
Brett swallowed hard. Be a good girl. The humiliation of having his masculinity stripped away with a few words made his cock throb. He stood and lowered his zipper, revealing a white lace thong.
“Ah, a thong. Very nice. Lower your pants, turn and bend.”
Cursing his choice, Brett did as he was told. He shuddered as Kate passed her small hand over his buttocks, running one finger along his crack before snapping the string that was wedged there.
“I'm pleased with your choice. Brave and sexy.” She slapped his ass. “Straighten up and pull yourself together.”
Brett ran a shaking hand through his hair as he did so. He sat, a hot blush still burning in his cheeks.
Kate smiled sweetly. “Will there be anything else, Mr. Andersen?”
“No. I don't want to be disturbed for the rest of the morning. Hold my calls.” He shuffled a stack of papers, refusing to meet Kate's eyes.
She didn't leave, though. Stepping closer, she leaned over his desk, and with two fingers under his chin, raised his head until he was looking at her.
“Just one more thing, and then I will adhere to our agreement. Since you'll be behind closed doors all morning, I want you to go online and order a cock cage. Stainless steel, not that plastic crap. You have my home email. Forward the order confirmation to me so I know you've done as you were told.”
She walked to the door, then turned and raised an eyebrow. “Not that I expect you won't.”
...
Later that morning, Brett forwarded the confirmation email as Kate had requested. He imagined her hands on his limp cock, stuffing it into the unforgiving metal of the cock cage for—an hour? A day? He shivered, wondering if it would be used for punishment or become a part of his daily routine. Despite a bit of apprehension, he was incredibly aroused at the thought of submitting to her.
It was something he'd been aware of for a while, although he'd discovered the many facets of his kink over time. He'd always loved strong women; it turned him on to no end when a woman took the reins in the bedroom. Through one particularly kinky and open-minded girlfriend he'd learned how much humiliation, in particular feminization, turned him on.
She'd discovered his panty fetish, and had used toys on him. That relationship had ended after a few months, but it left him with an intense desire for more. No other woman had been so open-minded, and he'd kept his predilections to himself. Until now.
He was still figuring out what really did it for him. He'd been in chat rooms, watched porn. What really got him going was the mind-fuck; having someone describe all the humiliating, dirty things they'd like to do to and with him. With Kate, he could be himself and explore all the things that made his cock hard. He could let go and truly submit.
He tried to put Kate out of his mind by busying himself with work. A brisk knock on his door made him look up. Glancing at the clock, he was surprised to see that it was already six o'clock.
“Come in.”
Kate entered and closed the door behind her. She took a seat in front of his desk, hands folded primly in her lap. “Do you need anything else tonight, Mr. Andersen?”
“No, I think we're good. Go home, enjoy the rest of your evening, Kate.”
“All right then. Since it is after business hours, though...”
He looked up, his stomach flipping. “Yes?”
“ 'Yes, Kate', but we'll work on that. I just want to establish a bit of a routine for us. From now on, you can send me a photo of the panties you intend to wear each day, and I will either approve or tell you to find something else. Or you can take your chances and show me when you get to the office.”
“Take my chances?” He repeated dubiously.
“Yes. If I don't like what you've chosen for that day, I may tell you to take them off and carry them in your pocket for the rest of the day. I may tell you to go out and buy something new. Or I may send you into the men's room to take a piss at the urinal in them.”
He shook his head. “We agreed; nothing that can impact my personal or professional life, Kate.”
She smiled. “Well, then... what is the answer here?”
“I'll send you a photo of the panties. Not on me, of course.”
“Of course... we'll get there, but not yet. I told you I wouldn't do anything to jeopardize you, and I meant it. But there do have to be consequences. So if you forget, or don't have time, or whatever other pathetic excuse you come up with, you know what they will be.”
Fuck. He'd be getting up extra early and making sure he got Kate's approval.
“Yes, Kate.”
“That's a good boy. One other thing. I want you at my place this Saturday at seven o'clock. Bring the cock cage, put on a pair of your prettiest panties and make sure your cock, balls and ass crack are shaved or waxed bare. Can you handle that?”
He felt the now-familiar blush rising in his cheeks.
“Yes, Kate.”
…
Saturday morning, Brett drove to a very high-end lingerie boutique two towns away. He selected a ridiculously expensive pair of red lace cheekies for later that night. His balls ached as he wondered what Kate would think of them. Whether he got her approval or a punishment, he was sure he would enjoy it.
Later that night, he carefully showered and shaved as he'd been instructed. Looking down at himself, he felt exposed, embarrassed; which was undoubtedly how Kate had meant for him to feel. The red cheekies felt exquisite against his bare skin, making him groan as he adjusted his cock. A final check in the mirror and he was off.
His mind drifted as he drove. His body was tense with anticipation. Could Kate be what he'd been looking for? Up until now, he'd satisfied his cravings for humiliation and submission with online chat and porn. How far would Kate push him? How far was he willing to go?
He pulled into the driveway of Kate's small, well-kept Cape. Grabbing the package containing the cock cage off the passenger seat, he got out and strode toward her front door, his heart pounding.
“Come on in, Brett.” Kate held the door open, ushering him in. Her use of his first name didn't seem out of place tonight.
“Thank you, Kate.” Brett found it easy to slip into submissive mode with her, despite their roles at work. Kate was a beautiful, strong woman. Her long, dark hair and cat-like green eyes lent her a touch of exoticism. He was eager and willing to bow down to her.
She took the package from him. “That's for later. Let's eat and talk about any questions or concerns you have. Anything, really, pertaining to our arrangement.”
He followed her into the kitchen. There were several containers of takeout on the center island. Kate handed him a dinner plate.
“Help yourself. I took the liberty of ordering for both of us. I know what you like.” She shot him a cheeky grin.
It was true, though. She ordered his lunch and sometimes dinner almost every day. She knew more about what he liked than probably anyone.
They took their plates into the living room. The furnishings were modern, neat and spare with splashes of bold color.
He followed her lead and sat on the overstuffed sectional in the middle of the room.They began to eat, making polite small talk until Kate delicately wiped her mouth and set her plate on the coffee table.
“So. How are you feeling about tonight?”
Brett considered her question. He was buzzing with nervous energy, horny as fuck, eager, scared.
“I feel ready.”
Kate smiled. “That's a good answer. This is something I sense you've wanted for a long time, and have done without, for various reasons. I'm glad to hear that you're ready now.
"I asked you to do several things tonight. I'm going to assume that you've done them. If I find otherwise, we'll deal with it in an appropriate fashion. Now, we should talk about limits. I don't want to do anything that crosses a line. We all have them.”
He thought about it. He had little actual experience exploring his kinks. But his fantasies sometimes took him to places that scared him. The more extreme the fantasy, the more it turned him on. Still, there were some things he was pretty sure he had no interest in.
“Scat, blood, anything that would leave visible or permanent marks...”
“All reasonable, and all things that I agree with. I know you have an interest in humiliation. Are there any subjects that are off limits? Things that might be triggering?”
He thought about it. It wasn't something he had a lot of experience with, but he loved the warm rush of embarrassment he felt looking at himself in a pair of panties, or imagining being bent over his bed and fucked. He wanted more of it.
“I don't know. I don't think so. Can we play it by ear and I'll let you know if something is too much?”
“That's fine. You're probably familiar with the stoplight system. Red if you need me to stop immediately, green if you're okay and want to keep going, and yellow if you need to slow things down a bit, but not stop.”
“And what about pain? Do you crave it, hate it, what kind of tolerance do you have for it?”
He thought of being being bent over naked, Kate's hand coming down on his buttocks again and again. Being paddled, flogged. His pants were getting uncomfortable tight.
“Again, I like it, but I'm not sure how far I'd be willing to go.”
“Okay.” Kate stood and picked up their plates. “We won't get through all of that tonight, of course. But it's stuff I need to know. And nothing is set in stone. At some point I'll be pushing those limits, and they'll probably change along the way.
"My bedroom is down the hall on the left. Undress except for panties, stand beside the bed, and wait. I'll be right in.”
Brett blew out a breath, then headed for the bedroom. Once there, he unbuttoned his pants with trembling fingers. He lowered the zipper, revealing the fine red lace underneath. He removed the rest of his clothes and stood beside the large four poster bed. The room was chilly, the cool air making his nipples pebble.
A few minutes went by before Kate returned. He was somewhat surprised to see that she was still wearing the tight jeans and blouse she'd greeted him in. It must have shown on his face.
“Expecting leather? Whips, thigh-high boots? Don't worry—once we get started, you won't be concerned with my outfit.”
She stepped closer, looking him up and down. “However... your outfit, such as it is, is a matter of concern.”
She twirled her index finger impatiently. Brett felt himself blushing as he turned, feeling Kate's scrutiny.
“Very nice, actually. Something I'd buy myself. Take them off and let me see if you've followed the rest of my instructions.”
He did so, his dick hanging limp and small from his hairless groin. She reached out, giving it a quick stroke, lightly caressing his balls.
“Good. Turn and bend.”
A mixture of humiliation and arousal washed over him as he bent at the waist. Kate palmed his firm buttocks before parting them.
“You appear to be eager to please. That's good. You won't want to displease me.”
She gave his ass a sharp smack. “Stand and face me.”
He did, and although he had at least eight inches on her, her unwavering stare made him feel small.
“You are to keep yourself clean-shaven and ready for me at all times. We've gone over the rules for what you are to wear to work. The same goes for the weekend. To start, we'll meet at least once every other weekend. If something comes up, you are to let me know right away so that I can reschedule our time together. There are no sick days, or personal days, or whatever. Unless there is a major conflict, I expect to see you here or wherever else I decide to meet, on time, and according to whatever rules I have set for that particular meeting. Do you understand?”
He nodded. “Yes.”
“Yes, what?”
“Yes, Kate.”
“Always use respect when addressing me. At work, you are Brett, or Mr. Andersen. When we're together, you'll answer to whatever I feel like calling you—bitch, slut, my good boy, good girl, whatever.”
She took his cock in her hand and stroked it to semi-hardness. His eyes fluttered closed and he swallowed hard, wanting so badly to come, willing Kate to keep going, stroke just a little harder...
Abruptly she stopped. “Now go and get your cock cage before this becomes a problem.” She waved him away.
Brett wanted to cry with frustration at the thought of being locked up, unable to get a release until... who knew? But it also thrilled him to know that Kate held it all in her hands. She would decide when and how he came.
He brought the bag with the cage to her. He watched as she removed it from its box, taking it into the bathroom to wash it before coming to stand before him.
“Today is Saturday. Because this is all new, I am only requiring that you wear it until Monday evening. You can shower and use the toilet with it on. The only thing you can't do, of course, is come.”
Her smile was cold and a bit cruel. “You can go forty-eight hours without yanking on that sad little cock, can't you?”
“Yes, Kate.” He hoped he sounded more confident than he felt.
“Of course you can. You don't have any choice, do you?” She slid the cool metal cage onto his cock. He winced as she closed the cock ring around his balls, slipped a small padlock on and locked it, pocketing the tiny key.
“Imagine if I happened to misplace this.” Brett's eyes widened in alarm. She winked.
“Well.” She grabbed her phone off the bedside table. “It's almost ten. We'll call it a night. I'll see you Monday; in the event of an emergency, you can call me, but don't dare waste my time to whine about wanting to come or how uncomfortable you are. I don't care and it'll cost you.”
She strode toward the door, leaving Brett standing naked and feeling a little left behind. This was it? She'd locked him in chastity and was sending him home?
She addressed him as one would a child. “Get dressed. Go home. We'll talk on Monday.”
He pulled his clothes on, careful to stretch his panties over the unfamiliar bulk of the cock cage. He headed out to the living room, where Kate was waiting by the door.
Her smile this time was kind. “This was a good start. Remember to be respectful, honest, and do as you're told, and this will be a good thing. This will be a really good thing.”
She opened the door for him. “Enjoy the rest of your weekend, sub.”
Her words made the hair on his arms stand up. He nodded, his throat suddenly feeling tight. As he walked to his car, he felt free in a way he never had before and eager to offer his submission at last.
Nadene
- 26.07.2021
- 4
- 0
- Category:
- BDSM
