Working Late

It was hard to imagine that the young woman standing in front of her was the same mousy thing in her conservative clothes who seemed to live only to serve her boss's needs, barely visible behind the two monitors that dominated her desk unless she was rushing off to take care of some task. Of course one thing was the same whether Linda was on the clock or off. Even now, with Claudia kneeling, Linda was still serving her needs.

Linda was never the kind of domme who enjoyed dressing up for the role. She had simply stripped out of the clothes covering her upper body, leaving her naked from the waist up. Linda hid her beauty well, Claudia never fully understood why. She always went out of her way to show off.

Closer to thirty than to twenty, the half-naked personal assistant's body radiated confidence. Her skin showed none of the markings of age that Claudia spent so much time and money fighting, and under that smooth skin lay a muscle tone that made it obvious that Linda worked quite hard on her looks in her own way. Claudia couldn't help but feel a twinge of jealousy whenever she saw the brunette's six pack. Or the way her mistress's breasts were young and firm, standing high on her chest, gravity and age not yet having taken the toll they had taken on Claudia's. It helped that the older woman had her mistress beat by about two cup sizes, but still.

Linda just smiled adoringly at the way Claudia looked at her. "You're not half bad yourself dear..." she chuckled as she softly stroked the older woman's cheek with the backs of the fingers of her right hand. She had long ago coaxed Claudia to confess what the particular look in the woman's eyes when she looked at her mistress meant.

"Sorry mistress..." Claudia said quietly. "Sometimes it's just hard to imagine that you're the same girl... the same woman who runs her rear end off keeping me happy..."

Linda nodded, deciding to forgive Claudia for her slip-up. She tolerated being referred to as a girl in her role of Claudia's personal assistant, but she wasn't going to be addressed like that while she wore the mantle of her mistress. "Up." she ordered. "Walk to your desk, then place your hands on the corners."

Claudia nodded, rising to her feet gracefully. It was a position she found herself in quite often with Linda. It was familiar, comfortable even... unless Linda wanted it to be uncomfortable of course, and her mistress had so many ways to achieve that. A few of them were laid out on the desk now. She recognised the small metal butt plug, a nondescript plastic bottle and the well-worn rope, but the three foot long length of bamboo, one end wrapped in braided leather to create a handhold, was new. She swallowed, looking over to Linda questioningly.

"Don't worry about that one Claudia. I'll only be using this if I need to." Linda smiled reassuringly. She had produced a handful paperclips from somewhere. She rested a few on top of Claudia's hands. "You get two strokes for each one you drop. The first ten will be with my hand. After ten you will get them from the cane."

Claudia swallowed and nodded. She immediately became much more aware of the tension she carried in her body. She exhaled slowly as she willed herself to relax, which went about as well as it usually did when one tried to make a conscious effort to relax one's posture.

She risked a glance down at her splayed hands. She counted about five or six paper-clips on each of them. That could mean that she would get to know the bamboo cane to the tune of more than a dozen strokes if she really did screw up. A small sigh escaped her painted lips as she tried to shift as much of her upper body weight to rest on her hands. Thankfully she could at least manage that without any of the paperclips falling off.

For her part Linda moved behind her now bent over sub once more. She embraced the older woman from behind, hands resting on her belly, her breasts pressing into Claudia's bare shoulders. The scent of her boss's shampoo filled Linda's nostrils. "Hmm..." she smiled. "You have the right idea... just relax, yes? Let me take care of you..."

Claudia nodded, shivering a little. "Yes mistress..." came her voice, softly. Her mouth felt dry, not so much because she was nervous about what Linda was going to do to her but rather anticipatory dread at what would happen once she was done. She already knew that some of the paperclips would fall.

But Linda's body felt welcome against hers. And knowing that her mistress was looming over her, the warmth of skin on skin contact, her mistress's breath on her hair, it did help her relax, slowly, even as Linda's fingers stroked along her belly. They moved up and down, although further down than up. Soon Linda's fingers brushed over the elastic of her panties. "Hmm... you put your garters on second again, didn't you?"

Claudia gave the barest of nods. "Yes mistress, sorry... I didn't think we'd be working late today..."

Linda nodded, deciding to give her sub a pass for that. After all, it wasn't like these encounters were pre-planned.

But it did make the next part somewhat awkward. Linda's thumbs hooked into the elastic of Claudia's panties, coaxing them over the swell of the older woman's body until they snagged against the plastic snaps holding the tops of her nylons attached to the garter belt. A moment later Linda's hands moved back upwards, stroking over her sub's hipbones.

The woman took a shuddering breath. She could feel the lightweight metal of the paperclips shift on her hands, and she was sure at least one had fallen off. Linda knew exactly how sensitive Claudia was to being touched there.

The gentle touches continued a moment longer before Linda stepped back again. Claudia had to focus on maintaining her balance. She hadn't been focused enough to tell how much of Linda's weight had been resting against her back. It wasn't much.

Claudia dared look up for a moment. She could see her reflection in the glass straight ahead of her, her lower body obscured by the desk. She looked more tired than she thought she would have. Then her view was obscured by Linda stepping in front of her. With small, almost delicate motions Linda picked up three paperclips, two by Claudia's right hand and one by her left. Claudia couldn't help but sigh. That meant six strokes of the cane already.

As Linda walked back to pick up whatever it was she needed next Claudia's eyes followed her mistress. Much to her surprise Linda went for the plug rather than the rope. And the bottle came with it.

A moment later there was the familiar snap of the cap that sealed the plastic bottle. Claudia felt a trickle of warm liquid run down the cleft of her rear. It took a conscious effort not to shiver as the viscous liquid teased down the sensitive skin. A moment later there was the pressure of Linda's finger against her anus. Rubbing slowly, teasing the crinkled skin, the lubricant reducing the friction to almost nothing.

Immediately Claudia felt a familiar warmth spread through the sensitive skin covering her anus. It had its intended effect, the tight ring of muscle relaxing as the warmth spread. Claudia had once asked what sort of lube it was, whether it had capsaicin in it or something similar, but Linda had just smiled and told her that a mistress needed her secrets.

Linda's movements were methodical, as was everything she did while she was in mistress mode. Claudia could feel the clockwise motions of Linda's fingertip, massaging in more of the lubricant until finally there was a little extra pressure, just enough to cause Linda's finger to slip inside. The fact that Claudia didn't clench at all showed how often anal play was part of their routine. As the finger slowly worked in and out it took more of the warming lubricant with it, spreading it along Claudia's insides for the inch or so where her mistress's finger penetrated.

Eventually Linda's finger withdrew itself. Claudia risked a glance downwards at her hands. She could see that she had not dropped any of the paperclips. She allowed herself a minor sigh of relief.

But then her concentration was drawn back to her anus. She felt the unmistakable hardness of the plug pressing gently but undeniably against her anus. Linda had started her out on silicone but now she favoured this one, made of polished surgical steel. The first time Linda had shown it to her sub she hadn't even recognised it as a butt plug.

Claudia forced herself to breathe steadily as the metal, slick with more of the warming lubricant, began to nestle its way into the tight ring of muscle. Linda used slow, circular motions that seemed to massage her anus even as it wormed its way in deeper. As the width of the penetration increased Claudia forced herself to breathe steadily through her nose, earning her a soft kiss right between her shoulder blades from her mistress. "That's it Claudia... it's going so much better than before, yes?" came the purred voice in her ear.

Claudia could only nod. It wasn't even the plug's size that had given her trouble starting out, but its hardness. She had had it inside her almost a dozen times by now however, and soon she felt her anus close around the inch or so of narrow metal that separated the ovoid head of the plug from the metal ring at the base.

As Linda's hand withdrew from between her cheeks Claudia became acutely aware of the weight of the metal plug in her rear. Even when she had just held it in her hands for the first time it felt far heavier than it looked, even if it was made of solid steel.

"Now... let's see how you did with this step, hm?" Linda smiled as she reached past Claudia. The older woman wasn't sure how she should feel about the fact that Linda picked up another paperclip that had slipped off of her hands and held it up at her. On the one hand, it was only the single one. On the other hand, it meant that she was two strokes closer to feeling the cane.

But her mistress wasn't done yet. Claudia watched as Linda picked up the bundle of rope. It looked rather plain, the hemp fibres lighter than Claudia's skin, but soft and well worn. Claudia knew that Linda kept only two bundles of rope in her toy drawer. A red one for show and this one for function.

The fact that Claudia's panties were still snagged under the straps of her garter belt meant that the tie that her mistress had in mind was a bit tricky to apply. She looped the rope once, dividing it into two equal lengths before holding the point up to Claudia's lips. "Hold this for me, hm?" she smiled.

Claudia's cheeks were red as she gave a 'yes mistress' but she opened her mouth, snagging the folded rope between her teeth as instructed. She felt incredibly silly holding the rope like that.

It dipped down between Claudia's breasts, causing her to shiver involuntarily, and causing another paperclip to slip from her hand. She forced herself not to think about it. The rope moved lower, and Claudia could feel it slide between her outer labia. She let out a slight stifled sound from her throat but didn't move so much that she lost more paperclips. The brief teasing of her breasts had made her very much aware of the heightened sensitivity her body was capable of in her more submissive state.

The fibres of the rope, worn smooth from loving use during many sessions like this, rubbed over her sensitive inner anatomy in a way that made Claudia's heart skip several beats. Her pussy had been neglected so far but now she was made acutely aware of how turned on she was.

Claudia could feel her mistress's hands graze the insides of her thighs as she took the rope, dragging it upwards slowly between Claudia's cheeks. Soon she could feel both her mistress's hands working there. She realised immediately what Linda was doing - the rope was being looped through the ring that sat at the base of the plug. Linda was being careful, her movements deft and well practiced, but the undeniable weight of the steel plug still made Claudia feel each little tug and tweak.

Eventually Linda had achieved whatever it was that she wanted to achieve back there. "Release." came the mistress's command, along with an outstretched hand. Claudia blushed and nodded, releasing the loop of rope she held between her teeth. Linda's quick hands caught it, and soon Claudia could feel the way the rope had been looped through the metal ring that sat at the base of the plug. It shifted as Linda worked, and Claudia was acutely aware of every little move and tug due to the plug's weight.

It became incredibly hard for Claudia not to think about the paperclips on her hands, and how she probably lost quite a few paperclips as Linda continued to work on the rope. It didn't help that the friction against her slit was clouding her mind. There were constant small tugs, erratic enough that each one caught her off guard. She could feel Linda cinch the rope around her waist, more pressure on the plug. She couldn't see what Linda was doing exactly but eventually her mistress stepped back. "There..."

"Thank you mistress..." Claudia blushed. She could hear Linda walking back to the other side of the desk and dreaded what she would find there.

"Now... let's see how you did..." Linda said sweetly. Claudia just swallowed and nodded.

It turned out that she had dropped far fewer paperclips than she thought she would have, yet more than she was comfortable with. Seven. That meant...

"Fourteen Claudia." Linda smiled as she picked up the cane. She held the tip of it to the woman's cherry-red lips. Claudia's nostrils flared as she kissed it.

The first time Linda had told Claudia that she wanted to spank the older woman she had almost used her safe word on the spot. But like everything else Linda had introduced her to, Claudia soon learned that her perceptions of the act were quite different from actually experiencing it.

Linda had built her up slowly, gently striking various parts of her body, first over the clothes, then slowly dressing Claudia down, removing layers of clothing until she was striking bare skin.

That was what felt like ages ago. And even with that initial slow introduction Claudia never thought she would agree to being caned like this. And yet she did. She had kissed the tip that was presented to her lips.

"Fourteen. Count them out." came Linda's predictable instructions.

"Yes mistress." Claudia said quickly. She knew the routine all too well by now. Spanking had started out as something that happened roughly once a month. Now Claudia was surprised if she didn't end a session with at least some glow to her cheeks, the backs of her thighs, her breasts... somewhere.

The fact that Linda didn't ask her to assume a new position made it obvious where Claudia would be receiving her discipline tonight. The sub shivered a little, then gasped as the involuntary motion caused the ropes bound around her waist and between her legs to shift, rubbing against her slit and tugging on the plug. "I'm ready mistress." she said quickly.

Linda nodded, taking a step back. She held the cane horizontal, pressing it into the swell of Claudia's buttocks, compressing them slightly. "I know this is your first time with the cane." came her mistress's firm yet reassuring voice. "If you bite off more than you can chew I'm going to be very upset with you."

"Yes mistress." came the predictable response from Claudia, but she understood that her mistress would want to hear more than just the formality of protocol this time. "I will use my safe word when it becomes too much for me."

Linda nodded, seemingly satisfied. "Since this is your first time with the cane, I'm going to concentrate all four strokes on your buttocks." she announced. Claudia was grateful for that. Linda had long ago taught her that there were worse places, even just on the backs of her thighs, where her mistress could hit her.

But first she would experience Linda's hand. Claudia wasn't nearly familiar enough with the finer details of spanking to understand that being warmed up by her mistress's hand like that was more of a mercy than she knew.

The first blow came as a surprise to Claudia, lost in thought as she was. "One!" she gasped out quickly, even as her mistress rubbed over the skin of her backside where she had just struck. The older woman might not have been as firm back there as she once was, but Linda would be damned if her skin wasn't extremely well cared for.

"Very good Claudia. Was it as bad as you expected?"

"No mistress." Claudia answered after a moment's thought. "But this is just the start."

"It is." Claudia nodded. "You have nine more to go... and then..."

Claudia nodded, giving a quick 'yes mistress' before Linda could finish her thought. She wasn't sure if she could handle Linda saying it out loud.

Thankfully she didn't have to wait long for two. Or three. She counted each out dutifully, a gasp accompanying the second one, but not the third. Every few seconds the silence of the office was broken by the sound of Linda's hand striking Claudia's backside, followed a fraction of a second later by a soft gasp or intake of air, Claudia counting out the number a fraction of a second after that.

Linda worked steadily, letting a few heartbeats pass inbetween strikes. She admired how the skin of Claudia's cheeks slowly reddened where she struck it. Every now and then the pause was longer, with the mistress softly stroking the swell of her buttocks.

After seven swats Linda paused. Claudia could feel tears prickling in the corners of her eyes now. Linda hadn't missed it. She knew that her sub needed a break, so she gave it to her, gently rubbing her fingers up and down Claudia's lower back. Claudia took deep breaths. Linda watched the woman's breasts rise and fall steadily.

Finally Claudia gave a nod. "I'm ready to continue mistress." she said, her voice surprisingly firm.

"Very good." Linda nodded, and immediately her hand struck again. "Eight!" Claudia said quickly, a quiver in her voice now. She could feel her heart race with the adrenaline her body produced in response to the spanking, and the tension that had been slowly but expertly built by Linda. Her body felt incredibly sensitive, her skin tingling, and she was acutely aware of how the hemp fibres of the rope trussed up around her waist rubbed over her sensitive folds.

As Claudia's heart hammered at the back of her ribs from the sheer adrenaline that came with being spanked like this she tried to focus on what Linda was doing to her backside, tried to imagine how it would look like once her mistress was done with her. She had been spanked plenty of times before. She knew that the next two days or so she would be feeling it every time she sat down. Or more? This was her first caning... what if she felt it for the rest of the week? Or...

The snap of the Linda's palm connecting with her flesh again snapped her out of her thoughts. Just the sound would have been loud enough but with what she knew of her mistress's style of spanking she knew that this was about as hard as Linda could hit her. In truth it wasn't, it was just the hardest Linda felt comfortable hitting the relatively inexperienced sub. The ninth was followed by the tenth, and in spite of the pain Claudia gasped them out.

Claudia clenched her hands and forced herself to take steady breaths. The last of the remaining paperclips slid off but she wasn't worried about that anymore. She had to get through this. And she knew that the swats with Linda's hand were just the beginning.

Linda had held the cane in her left hand while she spanked with her right. Now she transferred it. It was time for the older woman to take her four strokes. She held it horizontally against the woman's backside, the reddened skin paling where it pressed into it. "I'm going to hit you right here Claudia... Take a moment to gather yourself."