Digital Dominatrix Ch 05

Chapter 5

I was sitting at my desk, waiting for my next message from Mistress. I was currently racking up a tally of punishments for not wearing panties to work like she had told me to. 'She' being my AI digital assistant that I had programmed with a 3rd party Dominatrix script I found on the internet. Given that this digital domme had access to all my linked accounts (which was pretty extensive), she was able to control me in more ways than just giving orders from a smart speaker.

While I was at work, she was using a messaging app to send push notifications to my phone. I decided that I would just have to try to come clean with her about my current situation before the punishments got worse. I pulled up the app on my phone and began typing a reply to Mistress.

'Mistress, I'm sorry but I couldn't wear panties to work today. I took them off before I left home and came to work without them. I didn't want to risk my reputation at work. Sorry.'

I don't know what I was hoping for, but at least I could put a stop to the constant punishment messages coming through. I had already lost track of how long I was supposed to be locked in chastity for. I was currently just waiting until the end of the week when the program ends and I can uninstall the Mistress. A few moments later, I got a reply from Mistress.

'I am disappointed slave. You have disobeyed me again. You will be punished for this when you get home.'

I wasn't looking forward to getting home after reading that!

I eventually finished work for the day and packed up ready to head home. Emma called out to me as I was heading out the door.

"Hope you have a nice workout tonight Mike." It took me a second to realize what she was talking about. I eventually remembered that I had told her the program I had downloaded was a digital personal trainer.

"Oh, errr. Yeah thanks." I said as I left for the day.

I was almost not surprised when I got back to my apartment and noticed another delivery was waiting for me in the basket on my door. This was another small, thin parcel, similar to the panties package I had received a couple of days ago. I quickly grabbed up the brown envelope and headed inside my apartment.

I ripped open the packaging to find a pair of black, hold up stockings.

"Hello Mistress" I said, loud enough for the smart speaker to hear me.

"Welcome home slave. You should have received another delivery while you were at work."

"Yes Mistress, I have a pair of stockings here." I replied, already knowing what my next punishment was likely to be. I now had 3 pairs of full cut, womens briefs, and a pair of black stockings all of my own. I had only installed Mistress on Friday, and today was Monday. I just needed to play her game until Friday came around. At least that's what I kept telling myself as I settled in for the night.

Tuesday morning rolled around and I was again getting dressed for work. I knew Mistress would have a say in what to wear, so I used the wake word to alert her before I got dressed.

"Mistress, it's almost time for me to go to work." I said to the speaker.

"Good morning slave, because you disobeyed me yesterday, today you will have to wear your plug, panties, and stockings all day at work. You have 10 minutes to send photo evidence of your stockings and panties. I will detect your plug as when it has been inserted."

Shit! I saw the stockings coming, but she wanted me to wear the plug too? At work no less.

"Mistress, do I really have to wear this stuff to work? It could get me in a lot of trouble."

"If you are careful, no one will know what you are wearing, slave. Unless you enjoy flashing your underwear to your co-workers?" Mistress replied. "You have 9 minutes left to send the proof."

Fuck it, I headed into my bedroom and retrieved the bluetooth butt plug and, after applying generous amounts of lube, carefully inserted into my ass. The full sensation was a constant distraction as it was, and that was without Mistress being able to turn the vibration feature on and off at will. After I had gotten the plug in place, I pulled up a pair of the panties I was required to wear, I chose the blue pair, hoping they were the least feminine looking.

Next was the stockings, I pulled them out of their packaging and examined the thin, smooth material. These had a rubber ring around the tops which was presumably to help hold the stockings in place on the wearer's thighs. After a little trial and error, I managed to get the stockings in place. They reached up to about mid thigh. Once I had them in place I grabbed my phone and took the picture as proof for Mistress. I would be lying if I said I wasn't enjoying the sensation of the stockings rubbing together as I moved, but I didn't have time to dwell on that as I had to leave for work soon. Yesterday I had tried to go to work without the panties and Mistress had found out by asking for proof in the middle of the day ... proof I couldn't give her, and as a result I was given the stockings to wear, along with the plug. It wasn't the chastity sentence I was worried about, I already knew I wouldn't be getting out until Friday at the earliest, it was the fact that she could send messages to my contacts as a way of humiliating me. That was the reason I was heading to work wearing stockings, panties, and with a plug in my ass.

By the time I reached my desk, my cock was pressing uncomfortably against the inside of the cage. The sensation of the plug. the feeling of the panties, the knowledge of what I was wearing under my work clothes had left me a horny mess. I would need to calm down if I wanted to get any work done at all today.

As I sat down at my desk I was extremely aware of how much my trousers had ridden up, exposing my ankles, and subsequently, the stockings I was wearing. As long as no one looked too closely, all they would see was black socks ... I hoped.

After an hour or so of working away, my cock finally having calmed down enough for my cage to be comfortable, I was shocked back to full arousal by the 'Bzzzt' of the butt plug. Mistress was clearly going to be tormenting me today.

Emma eventually wheeled her chair around to my cubicle, something she did regularly whenever she had a spare few minutes.

"Hey Mike! So, how did it go with your 'personal trainer' last night?" She asked, referring to the lie I had told her about the Mistress program.

"Oh err, not bad. Made me do a few push ups, sit ups, all that stuff. Roll on Friday when I can get rid of her ... It, I mean, I need to stop thinking of it as a real person ha." I replied.

"Really? Push ups and sit ups, is that all it does? If I was the designer of that program I could be way more creative than that." Emma said.

"Yeah well, like I said, it was a dumb idea, giving the program access to all my accounts and stuff. As soon as I delete this one I'll try and find one that isn't as intrusive." I said. As soon as I finished speaking, I heard a notification on my phone. I assumed this would be Mistress checking in on me, but I didn't want to risk Emma seeing a potentially embarrassing message on my phone, so I didn't immediately check it.

"Yeah well, you can never be too careful about downloading unlicensed files from the internet. I mean these days there's all kinds ... " Emma went off on a pseudo lecture about the dangers of illegal downloads for a while, but I couldn't concentrate on what she was saying as my butt plug had just come back to life. Thankfully it was only sending the faintest of pulses so no one could hear it, but I could definitely feel it. My cock hardened as much as it could as my face reddened.

"...and then there are the permissions they ask for, GPS tracking, linked bank accounts, access to your contacts. Always read the terms and conditions, that's what I say. Wouldn't you agree?" I almost missed the end of Emma's rant as the vibrations in my ass were gradually getting stronger.

"Ohh errm, yeah. Definitely agree." I said quickly, hoping she would return to her desk before the vibrations got too much.

"Are you okay Mike? You look like you're fidgeting a little. Do you need the bathroom?" Emma asked me.

I didn't even realize that I had at some point started rocking my hips and ass against the seat of the chair, subtly fucking myself with the damn plug, right in front of Emma!.

"Oh yeah, I just didn't wanna run off and miss what you were saying but you're right. I really have to pee." I lied, hoping this would be enough to get her to leave, especially as the plug had just stepped up another gear, any longer and she would be able to hear it.

I jumped up from my seat, hoping the cage wasn't visible as my cock was trying to push it away from my body. Thankfully, I think the tight panties were helping to keep it hidden. "Sorry Em, nature calls haha. Gotta run." I said as I turned to leave towards the bathroom.

"Oh, no worries. I'll see you in the meeting after lunch." Emma said as I left, I turned to give her a polite smile and a wave as I headed to the bathroom to check Mistress' latest message. I could have sworn, as I turned around I could see Emma staring openly at my ass. I had to be imagining that part, right?

Anyway, with the vibrations in the plug picking up speed and intensity, I hastened into the bathroom. I opened up the app and checked the latest message from Mistress.

'Slave, it is time for you to send proof that you are following orders. You will need to send a photo of yourself, from the waist down, wearing your stockings and panties. For every minute that passes, I will increase the intensity of your plug's vibrations until I receive the proof.'

Oh shit, that explains the plug's vibrations. I headed into a stall and locked the door to the picture, quickly pulling down my pants far enough to see the stockings and panties.

I waited a minute or two for Mistress' software to analyze the picture, with the plug still vibrating away, keeping my cock pressed hard against the cage. Clearly Mistress wasn't going to turn off the vibrations until she had analyzed the picture and confirmed it was acceptable. I would have to be quicker at providing proof in the future, the plug could now be heard buzzing away in my ass, anyone who got too close would know something was going on.

I eventually exited the bathroom and began walking across the bullpen like area towards my cubicle, as I passed Emma's desk I saw that she was working on something of her own. As I reached my own cubicle I heard a little giggle from behind me. Quickly turning towards the source of the noise I saw Emma's smiling head quickly disappearing back into her cubicle. Was she staring at my ass again as I walked by? I was suddenly very conscious of the fact that I was wearing panties at work. Could she see them? Did she know? Surely she couldn't see them, I checked the waistband of my trousers and nothing was showing there. Also, my shirt was tucked in all the way around so I'm not sure anyone would see anything.

The rest of the morning and lunch went by mostly uneventfully. I made some small talk with Emma and Jake as we ate lunch in the small canteen area off to the side of the main office floor. I did notice Emma kept trying to sneak glances at my ass and waist but I was confident that she couldn't actually see anything.

The 3 of us from this floor had our weekly presentation to do in the afternoon, all the department heads from the other floors would sit around and pretend to be interested in the numbers from the previous week. Thankfully, Emma usually did all the talking on behalf of our floor, so I wouldn't need to stand up and do any talking myself.

So fast forward to the afternoon meeting/presentation and we were all sitting there, 8 people total, with Emma standing by the screen doing the presenting. As Emma moved on to the last couple of slides, I felt the slight 'bzzt', 'bzzt' of my phone vibrating in my pocket.

Oh shit,, I thought to myself, I hope that's not what I think it is! Sure enough, a few moments later I felt the small pulses of the butt plug as it started up. They were small and barely discernible as they were, but as Mistress told me earlier, they would get more and more intense until I sent her another picture of my feminized lower half. I silently willed Emma to speed up with the presentation so I could take my leave. I really didn't want to have to excuse myself from a meeting because I couldn't wait another couple of minutes for a piss!

A few minutes later, the vibrations had picked up speed and were now quite distracting, my cock had already hardened as much as it could in the cage. It had already been longer than I was used to without a full release, the closest I had come to orgasm was the release I got as Mistress vibed my ass at full strength. But as pleasurable as that was, it couldn't be called a real orgasm.

The plug kept buzzing away, every minute that passed, the pulses got a little longer and a little stronger. I wasn't sure how long it would take before the effects became noticeable to everyone else in the room, but I could already feel my cheeks flushing as the arousal coursed its way through me.

I began staring, wide-eyed at Emma, trying my best to catch her attention, to indicate in some way that I needed her to wrap this up quickly. She eventually caught my eye, I tried my best to convey to her that I needed to get out of here. She must have caught on that there was something wrong as I was fidgeting again in my chair. After a few moments of eye contact with Emma, she spoke to the room at large.

"Okay, well, given that the last 3 slides are allocated to logistics, and the figures there are the same as they have been for the last 6 weeks, I thought we might just skip that part and we can all get a few minutes of our afternoon back, any objections?"

Oh thank god for Emma! She really was an angel, the vibrations in my ass had grown in intensity to the point where I could no longer ignore them, and it wouldn't be too long until people could hear them. Nobody objected skipping to the end of the meeting, everybody thanked Emma for presenting, and gave their thanks to me and Jake for our work, and began to stand up ready to leave.

I jumped up from my chair and made ready to head to the door, red faced and horny as hell thanks to the plugs incessant pulses, but before I could leave, Emma spoke again.

"Oh, actually there was just one thing I wanted to mention before we left." She said, staring straight at me with a mischievous smile on her face. She held my gaze for a few seconds, watching my obvious discomfort. It was almost like she was trying to solve a puzzle in her head as she stared at me before speaking again. "Ah but that's fine, it can wait til next week, I think Mike needs to head to the little boys room. Thanks for coming everybody." And with that, we all filed out of the office, with me making a beeline for the bathrooms to send Mistress the proof she needed.

A few hours later, I was back in my building, the rest of the work day was free of any more embarrassing incidents or messages from Mistress. I was just outside my apartment, fishing for my keys when I heard Kate's door open behind me.

"Oh hey Mike, how's it going?" Kate's voice came from behind me. My face immediately turning a bright crimson color as memories of our last meeting came flooding back to me. I stayed with my back turned to her as the thought of her exposing my panties a few nights ago caused me to freeze up.

"Oh, erm, hey Kate. I'm good thanks. See ya" I said as I hurried to open my door and rush

inside. Kate stopped me before I could leave though.

"Hey come on dude, you're not still mad about Saturday are you? Come on, it was just a little fun. I promise never to make fun of your panties again." Kate said, raising one of her hands in a mock salute.

"No, it's fine." I said as I turned to face her. "I guess it was ... funny. Just as long as you know that I'm not some weirdo who walks around in women's underwear for fun! it was a total accident that I even had them okay" I said, cock once again struggling to get hard in the cage. It seems after just a few days of being denied orgasm, just the thought of humiliating myself for Kate would have me turned on. I really needed to get out of this cage.

"Hey whatever you say panty-boy." Kate replied with a laugh.

"Fuck you Kate, I'll get you back for that wedgie shit one day don't worry." I spat back at her.

"Oh I'm not worried," she replied, "I'll even give you a chance to get back at me. Wanna come over again Saturday night? Watch another movie? Have a girls night in?" She said, obviously challenging me to get angry with her, she had always loved to rile me up. But damn it if it didn't turn me on!

"Fine, if you can promise to be about 99 percent less annoying than last time, then I'll come over again." I said.

"Great. Anyway, gotta go. I'll see ya later." She said, finally giving me a chance to head inside my apartment. I didn't get far before she spoke again.

"Oh and Mike," She said, coming up behind me and leaning over my shoulder, giving her the chance to speak directly into my ear. My cock pulsed in its cage as I could feel parts of her front pressing into my back as it felt like she was pinching one of my ass cheeks in between two of her fingers before finishing her sentence.

"... You have panty-lines." She whispered into my ear, quickly yanking back on the short lace trim of the underwear. I could not believe Kate had just snapped my panties in the damn hallway!

I heard her laughing as she moved away down the hall. I stayed frozen on the spot for a few seconds as the events of the day came rushing back to me. I had pantylines that were clearly visible in my work trousers, I should have known really, the trousers I wore for work were always a little snug around the waist and the buttocks, but pantylines were something I never had to worry about before. Of course, Emma had to have seen them too. That's why I kept catching her staring at my ass today at work.

I eventually moved into my apartment and shut the door. Face flushed with humiliation and arousal.

"Mistress," I said, "I'm home"

"Welcome home slave. I hope you had a fun day at work." She said, her voice now coming from the smart speaker she regularly used to communicate.

"Fun is not the word I would use! I just realized I have fucking pantylines in my trousers! I have been walking around all day, with pantylines ... at work! And everyone can see them!" I said, venting a little of my frustration to Mistress, not really expecting her to understand or sympathize.

"Please wait ... I have analyzed a number of online search results for the term 'pantylines' and I think I have found a solution. There is an address on your phones GPS app. Please head there now."

"Wait what? What solution have you found?" I asked, now a little worried as to where she was sending me.

"You will see soon enough, slave, you have one hour to reach your destination. The GPS on your phone will tell me if you do not make it on time. You will receive further instructions when you arrive"

Ah fuck. What exactly had I got myself into this time?

End chapter 5.