The Boss


It's a terrible, terrible idea, he told himself. Don't be an idiot. You could get in so much trouble. You could lose your job. You could even get slapped with a harassment suit. Get a hold of yourself. Don't be that guy.

He already knew something was coming, and he already knew he was at risk of being fired. He thought about playing it off as a joke. He thought about staying silent and keeping his head down. He was desperate to make it right, but it seemed there was no way out. Most of all, he didn't want to lie to her.

As he started walking to her office, remembering it was like reliving a nightmare. Why hadn't he double checked before he sent it? Why had he even thought to do such an unprofessional thing in the first place? He had texted little comments to a friend of his before. They were largely innocent, he figured, but this time it was not.

And when he got a response, he could only stare in horror at it. "I assume this was meant for someone else, Ty. But I'm going to have to ask you to come to my office at 7 tomorrow." Sender: Jane. Your boss, dumbass.

By this time in the evening, the building had mostly cleared out so that walking to her office past aisles of empty cubicles felt ominous and strange. He imagined this was to prevent him from causing a scene. Though the security guard was still around, and maybe one or two of their coworkers. This wasn't certain, of course, because a lot of people in the office usually bailed right as soon as the clock hit 5. For all he knew, it could be just the two of them.

Jane's office sat at the end of a little hallway off the main area of the building. She always kept her door open during work hours, but tonight it was closed. Papers from ass-kissing coworkers and her kids decorated the small window in the door and obstructed his view of the inside. Yes, kids. She was happily married with children. A single woman might have forgiven his indiscretion, he thought, but a married woman? Not a chance.

He paused a few feet from the door to collect his wits, wondering what she could be doing behind the door. Had she been talking to her own boss? Someone in HR? He felt angry, but knew there was no denying who was really at fault. Time to do the best apologizing he had ever done in his life. He knocked on the door.

"Come in," she said calmly.

You knew this day was coming, he said to himself in resignation. From the moment you laid eyes on her, you were doomed. You had to make yourself behave during the interview. Don't stare, mind what you say, and don't lose your focus and make it obvious. You've known her for years now, but it's always been kept professional. Even when she would look you dead on in the eyes and you could feel your heart skip a beat. When she wears sleeveless outfits, showing off her strong arms and the tattoos running down her shoulders, and you force yourself not to admire them. That time in the parking lot when you all went to lunch and you caught sight of a wonderful pair of legs riding up to a short skirt in front of you, only to go blank when she turned around and you found yourself confronted by your boss.

Ty sighed a defeated sigh as he saw her on entering the room. Bare shoulders. Her arms were crossed. The stern expression on her face made him swallow involuntarily. She motioned for him to shut the door. This was it.

"Sit down," she directed him. Without thinking, he took the seat across from her and folded his hands nervously in his lap.

Her office was about the size of a small bedroom. She kept the lighting low, the desk perfectly centered against the back wall, and had very little hanging up or out on display aside from the gifts, signed cards, and similar things given by all her employees and her kids. She was a fun and easygoing boss most of the time, and had a bit of an issue with disorganization, but he knew she was also no-nonsense. Business first.

"I don't want to drag this out more than it needs to be," she stated emotionlessly. "You know why you're here."

"Look, I'm sorry, I--" Ty started before he was interrupted.

"Don't you dare say a word."

Jane had uncrossed her arms and put them on her legs. Her jaw had tightened. She saw the immediate reaction this produced in Ty. He sat back straight, eyes widened, and mouth left hanging slightly open. She could tell that he understood her. Now that the silence was allowed to linger for a moment and she knew she had his attention, she continued.

"I have every right to fire you over this. This is exactly the kind of behavior that leads to people being terminated. Sometimes even sued. Do you understand that?"

He nodded quietly.

"I really hope you do," she went on. "If you meant to send this to one of your coworkers--"

"I didn't. I was--"

She leaned forward and raised her voice. "I'm not done."

Again, Ty sat back straight. He closed his mouth and kept it shut.

"If this got out to the rest of the office, you would have been fired on the spot. Truth be told, I'm still not sure I shouldn't just fire you anyway."

He could hardly believe his ears. Was there... light... at the end of the tunnel?

Suddenly, she sat back in her chair and ran her hands through her short, dark hair in frustration. "I mean, what the fuck were you thinking, Ty?"

Jane watched him attentively. She noticed he waited for her permission, so she gestured to him to show he could speak.

"I..." he began. His voice was shaking and his face felt warm. He was almost sure that he was blushing in shame and she could see it. "I-I'm sorry. I didn't.... I wasn't..."

For a split second, while he was making eye contact with her, he realized how carefully he was being watched. She was studying his every movement. Instantly, he felt self-conscious and unsafe. He heard that voice inside warning again that this is a terrible idea. Don't be an idiot. Then he broke under pressure.

"I am so, just, so really, uhh, really attracted to you," he stammered out. "You make it hard for me to concentrate on work when you're around. I mean, I do my best. I always do. But I lose my train of thought... and I wasn't thinking when I sent that text. I'm absolutely sorry and I promise it will never ever happen again. Ma'am."

His terrible, rambling apology made him seem young and thoughtless. Though at 30 years old, this wasn't exactly true, she had a good ten years on him. She remembered the first time they met during his interview. He was young, but struck her as mature for his age. He seemed to be smart, methodical, and professional. But there was that one thing. She suspected ever since that he might be interested.

"You know I'm married?" Jane asked.

"I know," he answered quietly. "I don't know what I thought would happen. I didn't think."

"That's not the impression your text gave."

Ty froze. She stopped for a second, thinking about what she had said. She knew that this was dangerous territory to be on. To her mild surprise, though, something inside her didn't appear to care. She remembered her reaction when she had seen his text. Her first thought was a simple one that had haunted her for the past day. So he is interested after all.

As she had this thought, her eyes drifted down to the bag under her desk. There'll be no turning back, she reminded herself. You know that.

When she looked back up, Ty was in the middle of trying to form a coherent sentence. He started to apologize again, until the look she gave him steered him a different way. It said, unmistakably, Don't bullshit me. So he gave in.

"I can't take back what I said. But I didn't mean any disrespect. And I do promise it won't happen again."

A slight smile came across her face. She leaned back in her chair and looked at him.

"Well, what are we going to do about this?" she asked calmly.

Ty paused for a moment. "What do you suggest?"

"I have two ideas. One of them is that you walk out the door and we never speak of this again. The other idea is... not what you'd probably expect. You stay here and do some things for me. I won't blame or punish you for picking either one."

"Um," he said. "What kind of things?"

Jane leaned forward on her desk and looked deep into his brown eyes. Handsome boy. That was her nickname for him. No one knew it but her. When she saw him in that interview, in meetings, in her office, or even heard his name, that one thought came shortly after. She had wished for so long that she could get her hands on him. Her handsome boy.

"The kind of things that I'd need to trust you to keep secret," she told him softly. "Fun things. But private things."

Ty leaned forward and quieted his voice in response. "Are... are you sure?"

"Mmhmm," Jane responded.

"Yeah. I mean, Yes Ma'am. Anything."

"Good," she said. "Then go ahead and lock the door."

Once he had done this, she motioned for him to come near. As he stood next to her desk, she instructed him to drop his pants and bend over the side of her desk. Her fierce blue eyes studied him intently as he complied without hesitation.

"You seem like you came prepared," she teased him. She reached a hand into the bag under her desk and pulled out a large wooden paddle, dangling it in front of his face. With a wicked laugh that excited him all over, she said, "So did I."

"B-but the noise," he blurted out in a startle. "What if someone hears?"

She knelt down next to his head and cotinued teasing him. "Are you afraid of someone seeing you get your little bottom paddled? Don't worry about that. Leave it to me."

Jane walked around to stand behind him. He was bent over perfectly on her desk with his ass sticking out enticingly. She gently ran a hand down one cheek. Up to his back. Then straight down the middle, listening carefully as he began breathing heavier.

"We're going to play a little game," she told him. "I want you to start by telling me who you meant to send that text to. Then in between spankings, you get to recite every line of what you said for me. And there will be questions."

"Shit," he muttered. "Yes, Ma'am."

"Good. Go ahead."

"I... I was meaning to send that... to my roommate."

"Are you fucking serious?" Jane replied in irritation. "Your roomate? Have you been talking to your roommate about me like that?"


WHACK. A sharp sting bit into Ty's backside. He groaned and reached back, before she slapped his hands away. Fuck, he thought, this is what I get. Maybe try not to make her angry.

"You little bitch. I really didn't think you'd stoop that low."

"I-I-I'm sorry," he mumbled, still aching in pain.

"I guess we might have to show your roommate what really goes on between us now. Since you're so comfortable telling him all your dirty fantasies about your boss."

"No!" Ty objected. "Please. I'll stop. I won't say that shit to anyone anymore."

"You better not," she warned softly, lightly touching his red ass with her hand. "Now, let's hear you confess."

"Okay. I'm sorry, Jane."

"Oh no," Jane laughed. "Not tonight. You call me Ma'am tonight. Nothing else until you've earned it."

"Yes, Ma'am," Ty moaned. "I... I wrote..."

"Verbatim, boy."

"Yes, Ma'am... I wrote... 'Dude, my fine ass boss was wearing the short skirt again today.'"

WHACK. Tyler flinched and inhaled deeply.

"Fine ass boss, huh?" Jane remarked casually. She pressed her body against his bare behind and stroked it with her fingers.

"Yes, Ma'am," he agreed. "I..."

"Did you notice I wore another short skirt today?"

"...yes, Ma'am."

"I bet you did," she said. "Did you get a good view of my ass?"



"Fuck. Yes. Yes, Ma'am... thank you."

"I don't wear skirts for you to drool over, genius. I wear them because they're comfortable. Well, except for today. I wore this one for you."

Ty stayed silent. She looked down at him curiously. After a second she instructed him to go on.

"...'It's hard to resist... the temptation... to smack that booty sometimes'..."

At this, Jane burst into laughter. She sat down in her office chair and sized him up, looking at her with his head lying on the side of the desk. It pleased her to notice he hadn't moved at all. Perhaps he is learning, she said to herself. She leaned closer to his face.

"Tell me, Ty. Sweet boy. Who's having their booty smacked?"

Something remarkable happened next. Ty didn't laugh. He didn't make a resentful face or a humiliated face or anything of the like. Instead it seemed almost like he relaxed. What Jane saw appeared to be a grateful face, as he answered her: "I am, Ma'am."

With that, she got up from her chair and fondled his bare bottom again. Giving it extra care and attention this time. "Yes," she said. "It is hard to resist that temptation. Continue."

"I... uhh... I said, 'Love to get my hands on it.'"


"Do you think you'll ever be getting to do this to me?" she asked. He hesitated and she clicked her teeth. "You know the answer."

"No, Ma'am," he admitted quietly.

"That's right. My ass is off limits for smacking, spanking, and fucking. Isn't it?"

"Yes, Ma'am."

"Good. And yours? Tell me who yours belongs to."

"Oh," Ty sighed. "It... it belongs to you."

"Very good," Jane said sweetly. "You like that, don't you?"

He knew. Somehow she knew. But he hesitated.

WHACK. It hit his ass with a brutal thud. Ty couldn't hold back.

"Yes, I do. I do, Ma'am. I-I-I love it."

"Love?" she said with mock surprise. "Wow, I just said like, but you really love it. Don't you? You really want to be someone's little butt slut."

His silence made her pause. She walked around and bent down to meet his eyes. There it was again. That feeling she often gave him. Her breathtaking beauty, the way she carried herself. Watching her was like watching some marvelous being descend out of the heavens. Wanting nothing more than to please her. That's what it was.

"Do you want to be my little butt slut, Ty?" she asked playfully.

"Yes. I'd be anything for you, Ma'am."

Jane took him by the hair, lovingly yet assertively, and kissed him. Noticing he stayed bent over the desk still, she grinned and kissed him again.

"You know," she said in a teasing tone. "You may not get your hands on my ass, but I can think of other uses for you."

She ordered him to stand up and strip. He nervously did so, as she reached in her bag again. Out from it came a pair of wrist restraints. Turning him around, she locked his hands together behind his back. Then she helped him down to his knees.

In slow, sensual, and torturous movements, she bent over in front of him, sliding her skirt down to the floor. Underneath was a pair of black lace panties, tightly hugging a perfectly round ass that he desperately wanted to touch. She pushed her backside to within inches of his face, and delicately put her hands into the back of her panties, playing with her cheeks. Off came her underwear and her bare ass stood before him in all its glory.

Then suddenly she turned around. Taking one look at his cock, she could see he was fully erect. She knelt down, grabbed him by his dick, and spoke in a serious voice.

"Listen, boy. You need to know this is a privilege. I know you don't like to think of yourself as an ass-kisser, but you will absolutely kiss this ass, and lick it, and worship it. You'll count yourself incredibly lucky to do this, and you will never EVER disrespect me or my perfect ass again. When your lips and tongue touch my backside, I better feel nothing less than total surrender and gratitude from you. If you don't worship it right, you never get another chance. Am I abso-lute-ly fucking clear?"

Ty nodded and nodded. And nodded some more.

"I mean it," she warned. "And answer me when I speak to you."

"Yes, Ma'am."

With that, she turned around gracefully and backed herself towards him with a final reminder not to disappoint. She waited, wondering if he was going to be able to put himself this... low beneath her. For a second, she started to worry that he was struggling too much with his ego. She began to fear that maybe this was all a huge mistake. As much as she was in control, she put a lot of trust in him.

Her mind changed swiftly once she felt it. He kissed a cheek lightly. Then another. She heard his breathing grow loud enough that it was easy to hear even with his head behind her. She felt his insecurity and humiliation in the shy way he kissed her at first. But she loved knowing what that meant, even though she'd let him wonder and worry if he was doing it right, so she decided to give it a minute. And very soon, the dam broke.

He buried his face in her and kissed and licked her to the point that her legs rocked. She quickly threw an arm down on the desk and the wall to stabilize herself. A big smile emerged on her face as she pushed back and moved her body in rhythm with his face and tongue. A well of excitement bubbled up inside Ty once he heard her start to make pleasant noises. It became clearer and clearer that they were involuntary, while his cock continued to stiffen and ache.

"Mmm," she gasped. "I always knew you had it in you. My eager little ass-kissing bitch boy."

She knew this might be pushing too far. He lost his focus as the words resonated in his mind. Undeterred, she reached back and found his head. He just needed direction. So she shoved him deeper between her cheeks.

"Don't be scared. This is your place. Get in there and worship my ass."

Gradually, a voice crept into his mind. It was testing him, challenging him, pushing him. Haven't you been waiting for this? Craving it for years? Wondering and imagining and lusting and wishing? Is this not a dream come true? Don't hold back now. You know exactly what you need to do. Don't think you're not ready.

The moaning, groaning, gasping, and laughter mounted and mounted. Jane couldn't help admitting a feeling of amazement to herself. She did tell him she was giving him the privilege of pleasing a divine ass, and he had certainly taken his responsibility well when she took her seat on the throne. No, she thought excitedly, she would not be letting this one go.

"Not bad," she said, pushing his head back playfully and stepping aside. "It's a pretty good start for an ass-kisser like you."

Helping Ty back up, she uncuffed his hands and put him over the desk once more. Back here? His mind went searching for what was still left, until at last it dawned on him. And he shuddered.

"You didn't think you were through, did you?" she asked with a chuckle. "You still have one part of that text left."

"Fuck," Ty declared.

"Mmhmm," she responded. "You've been so good this far, handsome boy. Can we finish this off right? Let's hear it."

He closed his eyes. Took a deep breath. For a moment, he felt a flash of fear and resistance. But quickly that voice inside reminded him why he was there. This was a dream come true, and what was likely coming next was something he'd dreamed of before. Something he was a little scared to try.

"I...I," he stuttered. "I said... 'Maybe pound it good and show her who's the boss.'"

WHACK. The sting this time seemed less intense.

Jane sat down in her chair again and looked affectionately at him. "What do you think comes now?"

"You're going to fuck my ass," he told her with a shy smile.

"Do you want me to fuck your ass?"

"Um. I..."

"Don't be shy."

"Well," he said softly. "I probably deserve it."

"That's not what I asked. But yes, you do."

"...I know it's gonna hurt. And I know it will feel kind of embarassing or humiliating. And I'll feel pretty dominated..."

She grinned and petted the side of his head. "So? Why the reluctance?"

"'re my boss."

"I am," she stated firmly. "Your boss who you want to assfuck."

Hearing this, his face turned a bright red. He looked down for a moment, until she called his attention back to her.

Pub: 22 Dec 2020 12:31 UTC
Views: 148