Working Late Ch. 02

"I can feel how much you like this..." came Linda's purr into her ear as she stepped forward once more. The first time her fingers brushed over Claudia's slit the older woman's breath hitched in her throat. She couldn't deny it. Even with Linda stripped of most of her feminine features she still responded to her mistress's touch, the firm hand, being bound, made to kneel, made to perform... She could only shudder as she was stroked.

After a moment Claudia became aware of how odd it felt to have her breasts brush against Linda's waistcoat. The grazing of her stiff nipples against the pinstriped fabric made her shiver, but mostly it made her realize how much she missed Linda's breasts. Still, she leaned into the touch, desperate to feel more of her mistress.

She didn't have to wait long. The fingers withdrew, and a new pressure presented itself against her slit. Claudia bit her lip as she felt the rounded tip of Linda's toy nestle itself between her outer folds. When it was pressing into her throat it felt like she was asked to swallow a golf ball. Thankfully it didn't feel nearly as big now. She took deep breaths as she waited for the moment of actual penetration to come.

Like with her mouth, Linda seemed to enjoy taking her time claiming Claudia's cunt, savouring the anticipation in her submissive's body as it tensed up against her.

"How does it feel Claudia?" Linda purred in the older woman's ear.

"Uhm..." Claudia hesitated, trying to focus on the feeling of the silicone shaft rubbing up against her pussy in the middle of the turmoil of other sensations, both physical and emotional. "It's... it's not quite the same as a real one mistress..." she finally admitted.

"I wouldn't know..." Linda said with a smug grin that immediately made Claudia feel incredibly silly. She had never flat-out questioned Linda about her sexual preferences and history, but that remark answered a lot of the questions she had never asked. "But I've been told it's better than the real thing... less messy, no side effects, and it can last as long as I want it to..."

"How long... how long do you want it to last mistress?" Claudia asked, a nervous quiver in her voice. As usual in these sessions Linda had wound her up and played her body like a fiddle, leaving her feeling like she was walking along a narrow ledge with only her mistress's firm hand to keep her from falling over. She wasn't sure how much longer she could keep this up.

"Oh... until I'm done with you..." came the cryptic reply. "Now just relax, hm? You feel more than ready for this..."

Claudia nodded quickly, giving a meek 'yes mistress' that ended in a gasp as she felt Linda lean forward. She felt the toy slip in slowly, held steady by Linda's hand, the mistress's other hand holding the back of her collar firmly but gently, a stark reminder of where they stood in relation to each other right now.

The toy wasn't big but, like with Claudia's throat, it was a long time since she had had anything inside her like this. Linda leaned her upper body back a little, savouring the way her submissive's expression changed as more and more of the strapon was eased into her.

As Linda stepped forward her arms came to rest around Claudia's bound body, drawing the older woman up against her. Her slender fingers found her backside, kneading it slowly as she began rolling her hips. A quivering gasp escaped Claudia's lips as she felt the friction of the soft silicone rubbing up against her inner walls. After a few moments she tried to roll her hips to meet the thrusts but before she could figure out how to get the leverage she needed while trapped between her desk and her mistress there was a soft tutting in her ear.

"Now now Claudia... if I wanted you to move I would have told you to... Just focus on how good it feels to be fucked..." Linda grinned. Claudia could only nod and whisper a hoarse 'yes mistress.'

Linda was achingly methodical in how she used her toy. Claudia felt trapped in her mistress's strong arms. All she could do was sit there on the edge of the desk as the younger woman rolled her hips slowly. She was breathing hard, a shudder accompanying every intake of air. In spite of the fact that Linda seemed utterly focused on giving her pleasure she could tell how much her mistress was enjoying the power she held over her at that moment, the sense of control that she had over her.

And in spite of her unease at being with Linda when she was presenting herself so masculine she had to admit her mistress was playing her body wonderfully. She wasn't sure whether it was the bondage and the way her mistress restrained her, or the way she talked down on her, or just the feeling of having the toy grind up against her inner walls, setting the sensitive nerve endings there alight. She desperately hoped it was the first or third one. She wasn't sure what it would mean for her, or their relationship, if it was the added dimension of her humiliation that had gotten her so turned on.

For her part Linda loved the feeling of Claudia's body pressed against her. The scent of her perfume in her nostrils. The way she gasped and quivered with each deliberate thrust, each roll of her hips. She had never said it out loud to the older woman but there was a sensual beauty to her body that she loved bringing out during these sessions.

She leaned back, just a little, getting a direct look at Claudia's face. Under the smeared lipgloss and running mascara was the face of a beautiful woman in the throes of lust. She rewarded her submissive by bringing their lips together and shifting her arms. She draped her left around the back of Claudia's neck, holding her in the kiss, their tongues dancing together. She brought her right hand between them, to the point where their bodies joined. She rubbed over the dark curls where their bodies were joined via the toy, causing Claudia to gasp out in pleasure, her moan stifled by her mistress's mouth.

Linda didn't break the kiss. Nor did she stop her rubbing. Claudia squeezed her eyes shut. She tried to say something, possibly ask for permission to give herself over to the orgasm that Linda had been building her towards steadily. She took a deep breath through her nose, her abdominal muscles tightening as she felt the pleasure build every time Linda rolled her hips to grind the toy against her inner walls, every time she felt the younger woman's fingers rub up against the more sensitive parts of her outer anatomy. Even with their bodies pressed together, with no way to see where her fingers were stroking, Linda seemed to know exactly how to touch her.

Linda felt a surge of excitement as she felt her submissive's body tense up against hers. With their lips still locked firmly together what would have been a moan of pleasure came out as a muffled grunt. Claudia could feel her lower abdominal muscles clench as she came, shaking in her mistress's embrace. Her pelvic muscles tightened rhythmically around the silicone shaft. Linda savoured the slick heat against her fingertips.

The grinding stopped with Linda leaning against Claudia, letting the older woman ease off from the high of her orgasm with her mistress's body to brace herself against. It wasn't until Linda was sure that Claudia had fully settled back down that she stepped back. A small whimper escaped the older woman's lips as the toy was extracted. "There..." Linda smiled. "That was beautiful Claudia... let's bring you back down, hm?"

Claudia just nodded, shivering slightly. At Linda's guidance she leaned forward. Her mistress reached behind her. Soon Claudia felt the mobility return to her arms. Linda unbuckled the straps in reverse order, starting at her wrists and moving up. Finally Linda set the arm binder back down. "Limber yourself up a little Claudia, just like we practised."

Claudia nodded, rolling her neck and her shoulders, flexing and relaxing her fingers. As always Linda had bound her excellently, putting her at the very limit of her flexibility without causing pain or loss of circulation. Still, it felt good to be able to move her arms again.

She watched as Linda carefully extracted the strapon from her slacks and placed it in one of the resealable plastic bags that was kept in the drawer to keep the toys they used in their play sealed up until they could be cleaned. Claudia couldn't help but feel odd watching it removed so casually, considering what it had done between her legs and in her mouth. It really had felt like a part of her mistress.

Linda zipped up her fly and retrieved a bottle of water from the mini fridge. Claudia accepted it gratefully, taking several gulps of cold water before handing the bottle back with a 'thanks, mistress.'

Claudia smiled and knelt down, picking up the panties that had long ago slipped from Claudia's ankle. "Let's get you cleaned up and dressed up again, hm?"

Claudia nodded gratefully, letting Linda take the lead in it all. Tonight's session hadn't been that physically taxing but emotionally it had been more draining than she could ever remember their late night plays being.

Linda seemed to pick up on that, and the younger woman happily accepted the role of caretaker. Claudia's panties were slid back into place and her skirt was smoothed out. Linda took off the older woman's blouse briefly, but only so she could refasten the bra that had been resting on the tops of her breasts.

Once her blouse was buttoned up again Linda walked her submissive to her private bathroom. Claudia immediately noticed the pile of neatly folded clothes that sat on top of the now empty duffel bag. She looked from the pile and back to her mistress before taking a deep breath. "Mistress... can I watch you change back?"

Linda hesitated for a moment. She preferred to freshen up in private after a play session, and Claudia knew that. Which meant that Claudia had to have a good reason to ask. Linda nodded slowly, deciding to trust Claudia. "Alright, but we should clean up your make up first."

Claudia nodded at that. She didn't resist as Linda guided her to stand in front of the sink. Her mistress placed her hands against the porcelain rim and she gripped it.

She looked herself in the eye. In the mirror her reflection stared back at her, smeared lip gloss and runny mascara and all. For someone who paid so much attention to looking as good as she could Claudia had a hard time processing it. It wasn't even as if Linda had set out to ruin her make up, it was just a side effect of their play.

Thankfully she had her mistress for emotional support. Linda was right there besides her with cotton pads and make up remover. She held still as Linda gently dabbed and wiped, working slowly and methodically to clean Claudia's face.

"There we go..." Linda smiled, finally dropping the pads she had used into the small bin besides the sink. "Back to your old self..."

Claudia could only nod at that, grateful for the acknowledgement that the smeared make up wasn't 'her.'

"Now, I'm going to change... I'm going to need you to kneel for me, in the corner. Hands behind your head."

Claudia nodded, assuming the position as instructed. She knew that just the fact that she was allowed to watch Linda change was a sign of trust from her mistress. She didn't push for more than what she was given.

Standing in front of the mirror the first thing Linda did was undo the tight coils her hair had been held in. She extracted a dozen or so bobby pins and let gravity take care of the initial unwinding, rolling her head and letting her hair fall around her shoulders. A few quick passes with a hairbrush and it was mostly back to its usual form, brushing over her shoulders, even if she would probably need a shower to get rid of the product she had used.

Next came the waistcoat, and the dress shirt. Both were folded up neatly. They would need dry-cleaning before they were returned to their original owner.

With the dress shirt removed Claudia could see what had happened to her mistress's breasts. She was wearing what looked like a sports bra made of some sort of black synthetic fabric. She could just barely see the swell of her mistress's breasts in the way the light shone on the fabric but it was obvious that they were compressed up against her ribs. From where she was kneeling she could see the soft flesh bulge out slightly under the left shoulder strap. She watched as Linda lifted her arm. Underneath her left armpit was a series of clasps not unlike normal bra fasteners, just far more densely packed.

Claudia let out an audible sigh of relief as she fully loosened up the restrictive garment and pulled it over her head. Claudia could see a ring of reddened skin running horizontally over her midriff where the binder had pressed into it. Linda took several deep breaths. She had only worn the garment for about an hour but that was enough to make her ribs ache.

She decided not to take off the slacks. In stead she went over to the pile of clothes by the duffel, taking her bra, her undershirt and her sweater. By the time they were on she looked a whole lot more like herself, Claudia couldn't help but notice.

She watched as Linda stretched her arms overhead, wincing a little. Claudia could only imagine what her mistress had went through, even if Linda's breasts were considerably smaller than her own.

Much to her surprise she held the position she had been told to take all throughout Linda getting dressed and packing everything into the duffel bag. Given how much stress it had given Claudia over the past few days, it seemed utterly mundane. She was still holding it as Linda walked over to her and knelt in front of her. Linda released the collar and Claudia kissed it softly as it was held to her lips, along with the usual 'Thank you, Linda.'

A few minutes later they were both standing in the elevator, once again boss and personal assistant, with the various accessories of their play either packed in Linda's bag or stored securely in the bottom drawer, the key to which once again hung around Claudia's neck.

When the elevator doors slid open Claudia took a deep breath. "Linda... I was wondering if you'd like to go for hot chocolate again."

Linda paused, hesitating for a moment, then nodded. She had planned to go straight home but this had been another big play for her sub. Last time it had been her who had proposed extending the evening to help her wind down. If Claudia needed another trip to the diner she'd be more than happy to oblige. "Of course."

As they stepped out onto the snowy sidewalk Claudia hesitated for a moment. Linda was carrying the duffel bag that contained all the extra accessories she had brought in for that night's play, which left her left arm tantalizingly unoccupied...

She reached out slowly. Her right hand found the crook of Linda's left elbow. It wasn't quite holding hands or hooking their arms together, but it was still a more obvious expression of her feelings and desires for Linda than she had dared so far. She half expected Linda to pull away. But she didn't. Claudia could see the hesitation in Linda's body language. But then the younger woman gave the briefest of nods, and they were walking towards the diner. When the middle-aged woman working the bar noticed them she gave a polite smile. She set to work making two mugs of hot chocolate before Linda had even come up to order them.

Claudia smiled at Linda as her personal assistant set down the two mugs. The saucers they were sitting on bore some leftover Christmas cookies shaped like trees. There was something deeply amusing about the last remnant of holiday cheer.

She watched as Linda sat down across from her. It was hard to imagine that Linda had been so... masculine, for lack of a better word, thirty minutes earlier. Then again, those who didn't know her probably couldn't imagine her to be such a demanding, strict yet loving mistress either. Having this personal bond with the younger woman meant more to Claudia than she had ever imagined.

She watched as Linda broke off the stem of the Christmas tree cookie and dipped it in her hot chocolate. It looked like the cookies were still fresh enough, in spite of the fact that it was almost New Year's Eve.

The two sat in silence for a while. It was Claudia who finally spoke up first. "Was that the first time you dressed like... you know. A man?" she asked softly.

Linda smiled softly. "If you don't count my rehearsals for tonight, then yes."

Linda nodded, doing some mental math. It was the thirtieth, and they had last seen each other on the twenty-third. That meant a week to learn how to dress and present herself like a man, with the holidays inbetween. And the bag had been in her office on the twenty-seventh... "That's impressive." she finally said. "Did you learn from someone at Petra?"

"I did actually." Linda smiled. "I have a friend who performs as a drag king. She mostly taught me how to do the hair, and how to move."

Claudia nodded slowly. She had never heard of drag kings, but could infer the meaning from the words. But with the confirmation that people from Petra were involved, the next question popped up immediately. "Have you told them about... us?"

Linda just smiled and shook her head. "Of course not. They just know that I'm seeing someone. Jay knows it's you, but she only knows your first name."

Claudia nodded slowly at that. Linda had assured her that she would be discrete about their working late, of course. And she trusted Linda utterly. "I guess the women at Petra know the value of secrecy..." she said with a soft sigh.

"More than you know..." Linda nodded. "I've been very lucky..."

It was a bit of a cryptic statement, but Claudia had a feeling that she knew what the younger woman meant. She brought her mug up to her lip and took a small sip. Then she looked at Linda again. "I suppose there would be no harm in telling them about me... us."

Linda raised her eyebrow at that. When they had started their relationship Claudia had been terrified of them being found out. She had insisted that it was because of the ethical implications of a boss and her employee engaging in the kind of things they did, but Linda had always suspected there was more than that, if only because Claudia never talked about their dating history. "Alright..." she said finally. "I'm glad you trust me with that."

Claudia nodded. Of course she trusted Linda. But perhaps there was more than that. Perhaps if Linda started discussing their relationship with her friends, it would become more than that in her mind? It was something that had been keeping her up at night more and more.

Linda frowned from behind her mug. She seemed to sense her boss's unease. "You know... Jay asked about you over Christmas."

Claudia's eyes lit up as Linda mentioned the bartender. She had suspected that Linda's drag king act tonight was related to the conversation they had had, although she hadn't voiced those thoughts. "What did you tell her?"

"Not much." Linda answered, to Claudia's dismay. "She pressed me on whether I took you home with me... or vice versa, obviously." she sighed.

"And you didn't tell her what happened?" Claudia asked. There was a hint of need in her voice, as if part of her wanted Linda to tell her exactly what had happened - that she had convinced Linda to join her at her apartment, that she had fallen asleep with Linda's arm draped over her.

"I told her that there's a lot of things that we're both still figuring out." Linda shrugged. "That seemed close enough to the truth while respecting your privacy..."

Claudia nodded, although a small treacherous part of herself wasn't entirely convinced whether her privacy was foremost on Linda's mind when she gave her friend that non-answer. "What would she have said if you told her what happened?" she asked cautiously.

Linda had to think about that for a moment. "She probably would have been a little suspicious..." she finally admitted. "Jay has a bit of den mother inside her. We sometimes joke that we're not truly dating someone until Jay approved of her."