Working Late Ch. 02

She almost didn't recognise her mistress. Her eyes were first drawn to Linda's hair. It was coiled tightly against her scalp. Most of her long brown locks were pinned up with the help of bobby pins. It was slightly darker than normal too, which made Claudia suspect that hairspray or some similar product was being used to complete the illusion.

Claudia was so fixated on Linda's hair that it actually took her a moment to notice the other major change Linda had undergone while in the bathroom. Her upper body was clad in a men's dress shirt with rolled up sleeves and a waistcoat whose fabric matched her slacks. Dressed as she was in two thirds of a three piece suit Linda definitely radiated a masculine energy that Claudia didn't normally associate with either her personal assistant or her mistress. But what struck her most of all was that the swell of Linda's breasts seemed to have completely disappeared.

Linda seemed to bask in Claudia's attention on her, the mistress wearing a cheshire grin as she stood there with her hips slightly cocked. "What do you think?" she asked calmly.

If Claudia hadn't been in her totally submissive mood she might have remarked that the style of the suit and the waistcoat appeared to be maybe a few years out of date. And the fit wasn't quite right, especially around Linda's shoulders and hips. But right now she was thinking purely as a submissive so all she could say was "I think you look... you look very nice mistress..."

"Very nice?" Linda asked with a cocked eyebrow. "I was hoping for more than very nice dear..."

Claudia blinked at that. She definitely hadn't meant to disappoint her mistress, or, even worse, insult her, but Linda's transformation had come completely out of left field. She took a deep breath, trying to steady herself. "Sorry mistress..." she said softly. "I just... I didn't think you would... dress up like a..."

"Like a man?" Linda asked with an amused chuckle that suggested that she hadn't been quite as offended as Claudia had feared at first. "Well... I have my reasons... but right now you shouldn't worry too much about that, hm?"

Claudia blushed and nodded. "Uhm... yes mistress..." then, after a moment came another 'Mistress?' more questioning this time.

"Yes dear?" Linda smiled. She had a feeling what the source of her sub's confusion was, but she still wanted to hear her say it out loud.

"Do I... do I still call you mistress when you're dressed like this?"

"Of course." Linda chuckled. "Otherwise I would have told you, hm? Submissives shouldn't worry so much about thinking for themselves..."

Claudia blushed, bowing her head, giving a meek 'yes mistress.' The truth was that Linda had definitely considered taking on a new identity, to instruct Claudia to address her as 'sir' or even 'master' to complete the transformation, but she figured that her new appearance and new approach would be enough change for one night. She wasn't even sure whether she would keep dressing up like this. Her crossdressing act was new ground for both of them. She already suspected that tonight's debriefing might take longer than it usually did.

"Now... let's see you on your feet, hm?" Linda smiled. Claudia wasn't sure but she could swear that Linda's voice had dropped about half an octave. If it had, it sounded surprisingly natural coming out of her mouth.

Claudia took a deep breath as she rocked back onto her heels form her kneeling position, a single smooth movement that not only showed off how often she had performed this particular motion, even with her arms bound tightly behind her back, but also how good she kept herself in shape in general.

The older woman licked her lips nervously as she watched Linda move around her slowly. Her eyes were locked on the older woman eyeing her up and down, showing a naked lust for Claudia's body. The older woman had to swallow a lump in her throat. She wasn't sure what to think of being looked at like that. It was completely different from the way they had looked at each other back in her bedroom as they rolled around in Claudia's bed.

Suddenly Claudia realised why it was so different. Her mistress Linda hadn't looked at her body with such open lust before. She had enjoyed it, of course, and enjoyed exposing parts of her own body to Claudia, but this was the first time her mistress looked at her like this while she was wearing the collar. As Linda moved in slow circles around her Claudia tried to study her body language. The usual confidence was there, of course, but there was something more, something Claudia couldn't quite put her finger on. The closest she could come to describing it was that Linda seemed to be leading with her pelvis more than usual.

Suddenly Claudia was embraced from behind. She tensed up in spite of herself. Her fingers, bound firmly behind he back, curled into fists for a moment before relaxing again. She could feel Linda wrap her arms around her, stroking up her stomach. "Why are you so nervous Claudia?" came a soft purr in her ear as Linda rested her chin on the older woman's shoulder. It sounded more predatory than usual.

Claudia took a deep breath, forcing herself to relax. She managed it only marginally. "This is new for me, mistress... not just your look..." Claudia finally said.

"Hmm... They say clothes make the man, hm?" Linda chuckled at her own cliché. Claudia wondered if she had ever heard her mistress say something like that. She felt the need to reassert herself slightly.

"I don't think you need any special clothes to be my mistress, mistress..." came Claudia's reply, disagreeing with Linda as respectfully as she could in her current condition.

"I suppose I don't..." Linda chuckled as she ran her hands slowly up Claudia's body, shamelessly letting her hands glide over Claudia's breasts on their way to the top button of her blouse. Soon those buttons popped open one by one. As Linda's hands worked their way down they bared more of the golden skin of Claudia's cleavage. Soon the fingers were brushing over the delicate lace trim of the older woman's bra cups.

As more of her skin was exposed Claudia was breathing hard. She was used to these sessions starting with her undressing herself, in the employees' bathroom, to her mistress's instructions. Having Linda take off her clothes for her felt much more intimate. Almost like it had felt back in her bedroom... yet the fact that Claudia couldn't feel Linda's breasts pressing into her back made it very different at the same time.

"Hmm..." came Linda's husky voice in Claudia's ear. "I always love your taste in lingerie..."

Claudia blushed at that and nodded. "Thank you mistress... and I wore my panties properly this time..." she added with a nervous giggle.

"We'll see about that, hm?" Linda chuckled. Her fingers pressed into the soft flesh of Claudia's breasts, exploring them within the lace confines of her bra cups. "Are you that eager to get your panties off today?"

"N-no mistress..." Claudia said quickly. "I just... I didn't want a repeat of last time..."

"Oh yes, that was awkward, hm?" Linda chuckled at the memory of Claudia being left with her panties around her thighs as she was plugged, bound, spanked and caned.

Claudia swallowed and nodded. Linda could feel her sub's fingers curling nervously against her stomach.

"Now..." Linda smiled. She withdrew her fingers from Claudia's bra to finish unbuttoning the blouse, tugging it out of her sub's skirt. Claudia was left standing with her blouse hanging open. The white lace bra she was wearing that day did not do much to hide her breasts. She watched the silhouettes of her mistress and herself in the glass in front of her as Linda's hands came to rest on her shoulders. There was a slight pressure as her next order came. "Kneel."

"Yes mistress." came the submissive's immediate response. She watched as Linda moved around. It wasn't until Linda turned to fully face her that Claudia realised she had opened the fly to her slacks.

She realised it because of what was sticking from the opening in the garment - a soft pink shaft that protruded from the pinstriped fabric with a slight downward curve.

It clearly wasn't made for realism, really just a cylinder with a rounded tip. It was hard for Claudia to estimate its size from her kneeling position but it didn't seem overly large. The way it bobbed slightly as Linda moved suggested a certain flexibility to the material. Immediately Claudia's eyes were drawn to it, much to Linda's amusement. "I know you've seen one of these before..." she said calmly.

Claudia wasn't sure whether her mistress meant a strapon, or whether this was supposed to represent a penis, given how Linda was presenting herself, and acting herself. The answer to both was 'yes', but neither for a very long time.

Claudia watched Linda step forward. Her mistress's groin was perfectly level with her nervous, questioning face. Linda just smirked. "Open your mouth, Claudia... surely you know how to act in this position..."

Claudia wrinkled her nose at the rather crude suggestion. It wasn't something that suited her mistress, or her for that matter. She realised that Linda was performing a new kind of role for her. In their previous plays the focus had always been on pushing Claudia's physical limits in order to alleviate her stress. Now, dressed as she was, presenting the very phallic toy to her submissive's lips, she was testing the boundaries of Claudia's dignity.

After a moment's hesitation at that realisation Claudia slowly parted her lips. Rather than just shove the toy down her submissive's gullet Linda seemed to enjoy teasing her with it, rubbing it in slow circles over her glossed lips. Claudia had to suppress a shudder at how confident and in control Linda looked.

With one hand guiding the phallic toy Linda's other hand was free to brush through Claudia's long dark hair. "You're going to take all of this..." she said calmly, not with the aggression that might be expected from the more cliché types of pornography but as a simple announcement of her intent, certain in not just Claudia's willingness to open herself up to her mistress like that, but her ability too.

The 'yes mistress' that Claudia uttered was slightly muffled by the rounded silicone tip trapped between her lips. Somehow the half-formed answer annoyed her more than one she might try to give if she were fully gagged.

"Now..." Linda smiled. "Let's see how you like having your mouth filled, hm?"

As the toy slid past her lips and over her tongue Claudia became truly aware of the texture. It wasn't smooth. It had just the slightest hint of roughness to it, as if someone had tried to create an emulation of the texture of human skin but not gotten it quite right. There was almost no taste to it. As if by instinct she closed her glossed lips around it, her nostrils flaring slightly as she took a deep breath through her nose.

"There we go... like riding a bike, hm?" Linda smiled, causing the blush on Claudia's cheeks to intensify. Linda's chuckle at her reaction to the teasing remark told Claudia that the taunt had had its intended effect.

As the toy slipped further into her mouth Linda's hands came to rest on the back of Claudia's head. For a moment there was a tension in the older woman's body, a tension more pronounced than there had been before. Linda sensed it, and she paused.

When Claudia realised that the progression of the silicone shaft in her mouth had stopped she willed herself to relax. This was still her mistress. Her mistress looking for all the world like a slightly feminine man, sliding a fake penis into her mouth, but still her mistress underneath all those accessories. She immediately felt foolish for having doubted her.

Linda smiled inwardly as she felt her submissive's body slowly yield to her touch, glad that Claudia could still relax, even though she had altered the nature of their play without warning. It meant that her instincts were still intact.

Soon enough Claudia felt the strapon press against the back of her throat. It wasn't long enough to truly penetrate it but the rounded tip still created a sense of pressure that caused her to let out a spluttering gag, saliva bubbling up at the corners of her mouth. She looked up at Linda wide-eyed, pleading, but the pressure of her mistress's fingers at the back of her head didn't relent.

"Just relax Claudia..." came her mistress's firm voice. "In and out through your nose..."

Claudia tried to acknowledge the instructions with a nod but she soon found out that was a bad idea. It caused the phallic toy to shift against the back of her mouth, pressing against different areas and causing a fresh gag. This time Linda did pull back an inch or so, and just in time. Claudia's throat filled with fresh saliva and she had to swallow several times to pass it all.

By now her eyes were watering. Without much in the way of practical experience with something like this in her mouth she was struggling with even the lightest pressure. Her chest rose and fell rapidly as she tried to take deep breaths through her nose to steady herself. She could feel a trickle of saliva run thickly out of the right corner of her mouth and down her chin, but with her hands bound tightly behind her back she couldn't wipe it away. The light tickling sensation as it ran down her golden skin was maddening.

The gentle tickling sensation caused slight twitches in Claudia's facial muscles, especially around her mouth. Linda hadn't intended for that particular side effect of her teasing, but that didn't mean that she didn't enjoy it.

"Just a little more..." Linda smiled. "That's it... good girl..."

Even if the compliment was welcome Claudia was nonetheless struggling. She could feel her nose brush over the fabric of Linda's slacks. It was hard to feel proud over the fact that she had passed the challenge her mistress had set for her with the way she was drooling and spluttering.

Even as Linda was grinning down at her the mistress was watching her submissive closely. She could see that Claudia was still struggling to relax her throat. The stress on her body was entirely focused on her throat. And with Linda's fingers at the back of her head, it felt like she was well and truly trapped.

"I'm going to count to five, and then I'm going to pull back, okay?" came Linda's voice after a moment. Claudia recognised that tone. With her mistress there were always a few more seconds, just a little more, unless she used her safe word of course.

"One..." came Linda's voice as Claudia took a deep breath through her nose. Claudia had no idea how fast her mistress would count. Sometimes it felt like actual seconds, but often it felt like so much more. At least her counts were always consistent.

"Two..." Claudia tried to swallow, but mostly it caused her throat to just squeeze at the silicone shaft. Some saliva seemed to seep down her airways, causing them to burn. She tensed her body, but didn't try to pull back.

"Three..." Claudia tried to calm herself down. She was so close... and even if she couldn't use her safeword right now, she had to trust her mistress. She was sure she looked a mess right now...

"Four..." Almost as if in anticipation of her imminent release Claudia felt a spasm run through her body, a tightening of the muscles in her chest that left her to cough around the toy. Her eyes and throat were both burning by now.

"Five." With that Linda released her grip on the back of Claudia's scalp and slid back. As soon as the sub was free from the position she had been held in for what felt like an eternity Claudia doubled over. She strained at the arm binder, her reflexes telling her to clutch her stomach as she coughed. The burning feeling in her airways seemed to intensify. She could see a mess of splattered saliva on the tiled floor in front of her.

Then came Claudia's hand at her back, softly rubbing it over her blouse. "I'm proud of you Claudia... deep breaths." came her reassuring voice. "Deep breaths..." she repeated.

Claudia focused on the voice, and the hand. She took deep breaths, forcing herself to steady herself. She could see her face reflected in the polished marble underneath her, not fully, but enough to know that her make up was a mess, especially around her eyes.

"Don't worry about that..." Linda smiled, clearly sensing what seeing her ruined make up was doing to her submissive. "Here. Let's get you up."

There was a firm hand on her shoulder and Claudia soon felt herself moving up, her body responding almost as if by instinct to her mistress's guiding hand. She took a few more deep breaths, then a tentative step forward.

"Good girl..." Linda smiled. "Turn around, hm?"

Claudia nodded, sniffling a little as she turned around, facing Linda. She offered no resistance as her mistress guided her to walk backwards until the backs of her thighs bumped against the back of her desk. She took a deep breath as Linda's firm hands guided her to sit down on it. A moment later her legs were spread, and Linda was standing inbetween them.

The mistress's hand came up to stroke Claudia's cheek. The older woman looked up at her. She was used to seeing Linda at her desk, working away for her, or standing over her, holding a riding crop or some other implement of discipline. Seeing her now, much more masculine, the woman underneath just barely visible, was a whole new experience for her. And yet, when Linda's other hand disappeared underneath the front of her skirt to rub over the delicate lace of her panties, the warmth there was undeniable.

"Such a naughty girl... perhaps I should have dressed up for you sooner..." Linda chuckled as she continued to rub Claudia, fully playing up the role that came with her more masculine appearance as she leered at the older woman. Sitting the way she was, with her skirt pushed up by the spreading of her thighs and her unbuttoned blouse doing nothing to hide her bra-clad bust the older woman felt incredibly exposed, especially with the straps binding her arms together, leaving her with no way to cover herself up from her mistress's hungry eyes.

Claudia could only gasp as Linda stepped further forward. She could feel the toy between her mistress's legs, still glistening with her saliva, rub up against her underwear. Linda's hands slipped under her blouse, rubbing up her sides, causing Claudia to shiver.

As Linda's hands slipped higher Claudia became aware of their destination. Sure enough, her mistress's nimble fingers soon worked open the clasp of her bra, pushing it upwards until her breasts fell free. They rose as Claudia took a deep breath to steel herself.

Linda leaned into her, kissing at her neck directly above her collar as her fingers dug into the plush flesh of her breasts, her thumbs lightly compressing her nipples, causing fresh tingles of pleasure to run down Claudia's spine in spite of how vulnerable she felt at that moment. She leaned into the kisses.

"That's it..." Linda's voice slithered into her ear. "You know what I'm going to do next, do you?"

Claudia nodded. It was obvious from her position on her desk, and the way Linda leaned in against her. "Yes mistress..." came her voice in a hoarse whisper.

"Tell me..." came Linda's immediate response.

Claudia swallowed a lump in her throat. "You're... you're going to... to f-fuck me... mistress..." She hoped that Linda would approve of her choice of language. And that she had picked right, of course.

"Mhm..." Linda nodded. "Right here... on your own desk..."

Claudia shivered as Linda stepped back, pushing her thighs back together, but only long enough for her to pull down the older woman's panties. Claudia had to lean back on her hands to take her weight off of her backside so that Linda could peel them back fully. Almost as if to emphasize the nature of the older woman's current position they were left to dangle forlornly from her right ankle.