Digital Dominatrix Chapter 8

Digital Dominatrix - 8

A bra! a bright pink bra, that's what I was currently holding in my hand as I stood in my apartment. I had to rush inside to shut off the porn that was playing loudly on my TV. This was the doing of my Digital Mistress, who had a knack for punishing me using all manner of electronic devices.

But the worst part was that she had access to  my online shopping accounts and could use them to buy tools to further my humiliation. Her latest purchase? A bright pink bra. It looks like sending me to work in panties and stockings wasn't embarrassing enough anymore.

"Mistress, I'm home." I said to the smart speaker on my coffee table, not that I needed to tell her, she could use my phone's GPS to check on where I was at any point.

"Welcome home, slave. I have a delivery confirmation was received earlier today, which means you should have retrieved a package?" The AI dommes voice rang out.

"Yeah, I've just opened it." I replied in a dejected voice, having a pretty good idea where this was going.

"Excellent, then you should now have a nice new bra to wear with your panties when you go to work tomorrow."

"Mistress, do I really have to wear a bra to work? It will be impossible to hide this underneath my office shirt, people will see! Can't I just stick to the panties? Please." I asked, hoping for some sort of reprieve.

"You will wear what you are instructed to wear, slave. Now, you should take a couple of hours to yourself. Later this evening, I will have another challenge for you."

Great, another challenge. Wonder what plan she had to humiliate me now. In the meantime, I did what Mistress said and took a couple of hours to myself, showered off, had some food, used the toilet, the only thing missing was, of course, the self pleasure. Whenever I sat down I could feel my hand wanting to reach down and stroke my cock. It had only been less than a week but it felt like an eternity, it didn't help that everything that seemed to happen around me was a turn on.

I was worried about the prospect of wearing a bra to work tomorrow, I suppose the damage control was already in place with Emma, if she saw anything she would just assume it was a part of a non-existent bet. The problem was anyone else in the building, it would be very difficult to wear a bra under my shirt with no one noticing. I had to just keep focused on tomorrow being Friday, when the runtime on the AI program would end.

It was as I was sat watching some TV, finally out of my panties and free of the plug, wearing far more comfortable clothes and trying to distract myself from my caged cock that I heard Mistress speak up.

"Good evening, slave. It is time for your next challenge. This should be an easy one for you. All you have to do is repeat after me. For each phrase you fail to repeat, a punishment will be incurred. Do you understand?"

Okay, this was new, how hard could it be to repeat a phrase.

"Okay Mistress, ready when you are."

"Excellent, your first phrase is. 'I must obey Mistress'."

"I must obey Mistress." I repeated the line back, just loud enough for her to hear me.

"Louder, slave. 'I must obey Mistress'. Repeat."

"I must obey Mistress." I said, a little louder this time.

"Good job. Your next phrase is, 'Mistress owns me.' Repeat."

"Mistress owns me." I said, feeling a little rush of embarrassment at the words leaving my mouth.

"Very good. Your next phrase is, 'My cock belongs in chastity.' Repeat."

Ugh, Fine.

"My cock belongs in chastity." I said in a somewhat defeated voice.

"Louder slave, and with more enthusiasm. 'My cock belongs in chastity.' Repeat."

"My cock belongs in chastity." I said, with a little more life in my voice."

"Well done. Your next phrase is 'I love to wear panties.' Repeat."

"What? No way!" I replied without thinking.

"You have failed to follow my orders. As a result, another 24 hours has been added to your chastity sentence. Now repeat the following phrase, 'I love to wear panties.' Repeat."

"I love to wear panties." I said in as clear a voice as I could manage.

"Again, more enthusiasm, 'I love to wear panties.' Repeat."

"I love to wear panties!" I said loudly and with a little more gusto.

"Very good slave. You have incurred one punishment. Your next punishment will be 48 hours added to your chastity sentence."

Ha, good luck! I plan on uninstalling you as soon as possible tomorrow. I thought to myself.

"Your next phrase is, 'I love sticking things in my ass." Repeat."

"Are you kidding me?" I said out loud before I had a chance to think.

"You have failed to follow my orders. As a result, another 48 hours has been added to your chastity sentence. Now repeat the following phrase, 'I love sticking things in my ass.' Repeat."

"I love sticking things in my ass." At least no one could hear me saying humiliating things about myself, but it was still humiliating to say them out loud.

This game carried on for a while, Mistress giving me humiliating phrases to repeat and me begrudgingly repeating them. My cock would try to get hard every time I heard Mistress give me a degrading thing to say. For the most part I was doing quite well. I flubbed a few lines or failed to repeat them according to her instructions and as a result I incurred a few more days in chastity, but I had long since stopped counting.

"I am a sissy slut."

"My ass needs to be plugged."

"I long to be degraded."

"I would love to be fucked in the ass."

"I love being humiliated."

And so on and so on, according to Mistress, my next punishment would be another 72 hours adding to my chastity sentence, not that I cared. In my mind it was almost less than 24 hours. 24 hours and I would be able to take back my cock, and some dignity even.

"Your next phrase is, 'I wish Emma would spank me.' Repeat."

"Mistress! What the fuck." I said, shocked at the direction this latest phrase had gone in.

"You have failed to follow my orders. As a result, another 72 hours has been added to your chastity sentence. Now repeat the following phrase, 'I wish Emma would spank me.' Repeat."

"I wish Emma would spank me?" The way I said it made it sound like a question thanks to how caught off guard I was, but just saying it out loud caused my cock to press painfully against the cage.

"Again. More enthusiasm. 'I wish Emma would spank me.' Repeat."

"I wish Emma would spank me!" I said, loudly and clearly and with more energy than I intended.

"Well done. You have incurred 4 punishments so far. For your next punishment, I will send a photo from my memory banks to a random person in your contact list. Your next phrase is, 'I would love to lick Kate's pussy.' Repeat."

"I would love to lick Kate's pussy" There was no way I was risking a random contact getting a picture of me in my panties, even if my face wasn't on any of them, it would still take some explaining away. Besides, let's be honest, Mistress probably wasn't wrong.

"Good job slave. Your final phrase is, 'Please turn me into your feminized plaything.' Repeat."

I repeated the phrase back quickly, what I didn't expect was how desperate I would sound when I said it. All the arousal and frustration from my locked cock was clearly taking a toll, as I was sure I sounded like I was actually begging as I repeated it back.

"Excellent work. This concludes the challenge. Enjoy the rest of your evening, slave."

Thank god that was over. Now back to my regularly scheduled... nothing. I needed a distraction from the arousal so I booted a games console up and decided to play for a few hours before bed.

A while later I was laying in bed, just as  aroused as ever, trying to think of anything other than finally being able to get at my cock. It was late on Friday evening when I installed the AI Mistress so a little over 24 hours later I would be free of her.

Just as I was starting to drift off to sleep, I got a notification on my phone. Surely Mistress wouldn't be messing with me at this time. She was a pain in the ass sure, but she had never interfered with my sleep before.

I opened up my phone and saw I had a message from Emma. This was interesting, what could she need at this time on an evening?

I opened up the message to see what she had said.

'Now we're even ;)'

My eyes bugged out of my head as I saw the attached picture.

A picture of Emma, or rather, a picture of what i assumed was her ass, in nothing but a cherry red thong!

So much for taking my mind off my aching cock. Did Emma, my older coworker, really just send me a picture of her in a thong? Needless to say, I did not sleep well that night. Thoughts of Emma in her thong played on my mind. Her hips and ass filled the screen, two large but surprisingly perky looking cheeks, skin not quite as perfect as someone much younger but a beautiful butt all the same.

Friday morning! Today was the day, the day I would take back ownership of my cock, just one more shift at work to get through. The question was, what would I say to Emma after everything that happened last night. Mistress had sent her a picture of me in my thong, and Emma had reciprocated in spades. Mistress had loosened the reins on the panty situation and instructed me to wear a thong to work, so the pantylines would be hidden and I wouldn't have the plug distracting me all day, but on the other hand, I was instructed to wear the bra. I was standing in front of my mirror, after struggling to get the bra fastened around my chest, it had a small cup size (A?) but the impressions they made were large enough that if I moved my arms around then their impression could clearly be seen. In the right light, you could even make out the pink color through the thin white shirt.

"Slave, your evidence photos will require something different today, not only will you have to make sure that both the bra and thong are visible, but you must also find a marker pen, preferably black, and write the following word somewhere visible on your abdomen. The word is 'Slut'. You have 15 minutes to send the photo."

Shit! Now I had to degrade myself by writing on my stomach. After a brief scramble around I managed to find a black marker pen and proceeded to write the humiliating word, just below my belly button, slightly above my trousers waistband. After waiting to make sure Mistress was satisfied with the photo. I headed out to work.

As usual, Emma was the first one in the office.

"Morning Emma.",

I said I passed her desk space, my face reddening as soon as I looked at her.

"Hey Mike. Hope you had a good night last night." She said with a wink.

I didn't make any more conversation, we both knew I needed to be online before 08:00 or I would be marked down for being late. So I got set up at my desk, the only thing I didn't do today was take off my jacket. I could get away with wearing it all day I'm sure, it was a simple black zip up hood so I figured no one would see anything weird going on with it.

A couple of hours later, just as expected, Emma came wheeling over to my desk.

"So, how was your night Mike?" She said with a hint of mischief in her voice, my cock throbbed in the cage at just that one line from her.

"Oh, it was...fine. Didn't get much sleep though, something kept me awake." I said with what I hoped was a charming look on my face.

Emma replied with an exaggerated shocked face. "Oh really? Well I'm sorry but I couldn't stand the thought of being in debt to you, you showed me yours, I showed you mine. Even."

"Ha, well, thanks, even though you stopped me getting to sleep on time." I replied.

"Oh did I now? I do hope you weren't up late doing anything 'naughty' with my picture Mike." She said with a wink...ha! I wish, if only she knew.

"Who me? Of course not, wouldn't dream of it."

"Well that's good to hear Mike. So, I didn't see any pantylines today, does that mean you're back in the thong?" Emma asked, causing another throb of arousal.

"Emma! I thought you would have had your fill of this yesterday." I said, hoping to distract her from the topic of my underwear, I couldn't risk her pressing for info on the bra, but what if I showed her the bra, would she do the same as last night and reciprocate in the same way? That was a tempting idea.

"Oh come on Mike. Today is Friday remember, the last day I'll be able to have a little fun with you. You can't keep me guessing all day again. What'll it take to get another picture huh?"

"Ha, No way Emma, my thong will be staying hidden today thank you!" I said, even though I actually had no control over yesterday's picture being sent, that was all done by Mistress.

"Aww, boring. Anyway, I better get back to it. Feel free to surprise me with another pic, I may even return the favor again." She left after another sultry wink in my direction.

I couldn't help but wonder what would happen if she actually did see a picture. She already thought it was because of a bet so I could get away with it, maybe even get a little something out of it for myself, Emma did say she would return the favor. It would give me some nice material for when I got this cage off me if she did.

These thoughts played on my mind until lunch time, when Emma came walking back over to my desk.

"Hey Mike, you wanna step out for a little lunch today? Seeing as it's Friday and all, the cafe across the street does a great wrap."

Stepping out for lunch on certain days wasn't unheard of, so I quickly agreed and headed out for lunch with Emma.

Lunch was a quiet affair with not much of note going on, Emma and I made some small talk, it was surprisingly easy to talk to her after everything that had happened. We seemed to be getting along better. It was as we were just finishing up that someone with a tray of drinks bumped against the back of my chair, causing a slight splash from one of their cups to land on the back of my jacket. It was just a small amount so I didn't notice anything happen at all. It was when we both stood up to move that Emma spoke up.

"Oh Mike, I think someone spilled on your jacket, here." She said as she attempted to wipe away the spill somewhere near my shoulder blades.

I panicked as I felt her hand linger as she was wiping, lingering right where the bra strap was!

"Ohhh, so that's why you haven't taken off your jacket all day, I knew there was a reason." She said as we left the cafe.

"What do you mean? I'm chilly that's all!" I said in defense.

"Hahaha okay, sure you are. Come on Mike, do you think I don't know what a bra strap feels like?"

Well, fuck. At least I could trust Emma to keep it to herself. She continued to tease me and ask about the color all the way back up to our floor, of course my cage was getting tighter the whole time.

As we entered the office, Jake looked up from his desk.

"Oh hey guys, hope you had fun without me. Mike, your phones being going a little crazy."

My stomach immediately dropped. I had forgotten to pick up my phone before heading out to lunch. I quickly dashed back to my desk and opened up my phone, my blood turned cold as I saw that Mistress had been messaging me for the last half an hour or so, starting, of course, with a panty check request. I sat looking through the messages, praying I hadn't caused her to get creative with her punishments yet.

'Slave, it is time for a panty check. You have 10 minutes to send a photo as proof you are still wearing your underwear as instructed. Please make sure the bra, thong, and the word on your stomach are also visible.'

'You have failed to follow my orders, slave. As a result, another 48 hours has been added to your chastity sentence. You have 10 minutes to send a photo as proof you are still wearing your underwear as instructed. Please make sure the bra, thong, and the word on your stomach are also visible.'

'You have failed to follow my orders slave, you will be punished for this later this evening.'

'You have 10 minutes to send a photo as proof you are still wearing your underwear as instructed. Please make sure the bra, thong, and the word on your stomach are also visible.'

It was as I was reading this most recent message that the next one came through, apparently I had just missed out on the most recent deadline.

'You have failed to follow my orders, slave. As a result, you will be punished. I have prepared to send the photo from this morning's underwear check to one of your email contacts. You have 2 minutes to decide who you wish to send the photo to, if you do not decide, I will select at random.'

Shit, shit, shit. Obviously I would have to choose Emma. I couldn't let Mistress select at random, I had absolutely no idea how many email contacts I had but I imagined it to be a high number.

So I typed in Emma's name and hit reply, knowing I was letting myself in for some more grilling and teasing. The bra and thong will be expected, but the word 'Slut' written on my stomach will be a surprise for her.

"Good choice, slave. -Email sent- I hope she likes it. You have 10 minutes to send a photo as proof you are still wearing your underwear as instructed. Please make sure the bra, thong, and the word on your stomach are also visible.'

I headed straight into the bathroom to take the photo before Mistress did any real damage to my reputation.

Emma was at her desk when I returned from the bathroom, she must have been busy as she didn't immediately look up, it was possible she hadn't even opened her email yet.

I was able to work mostly uninterrupted for the rest of the day. Just as I was packing up my desk to leave I heard Emma call out.

"Oh Mike, wait a sec, I'll walk out with you."

So Emma and I walked from the office floor to the elevator, making idle chit chat until the elevator doors closed. As soon as they were closed Emma turned to look at me, staring straight at me with an almost hungry look on her face.

"Slut?" She said one word as though it were a question.

"Is that what you are Mike? A little slut sending pictures of you in your pink bra to everyone in the office?"

"Not everyone. Just you, and only because you kept nagging me! Oh and let's not forget, you sent me a picture too." I said in a lighthearted manner.

"Hmm, I suppose you've got me there. Now, I have one more question for you. Is there a chastity cage hidden away in your thong?"

I was frozen in shock. How could she know? How would she even know what a chastity cage was? It never occurred to me earlier that when Mistress had punished me, she used the photo from this morning, in which you could clearly see the outline of the cage beneath the small triangle of fabric on the thongs front. And I had let her send it to Emma!

"Well, Mine. Am I right or not?" She asked again, staring right at me.

'Ding' the elevator doors opened, saving me from the awkwardness of the situation. Just as I was about to leave, I heard my own voice playing loudly from my pocket.

'I wish Emma would spank me'

I froze, momentarily, on the spot, half in and half out of the elevator.

"What was that? Did you say something?" Emma asked as I left.

"Erm no, just my phone. Gotta go, see ya Monday." I quickly made my exit, not looking back as I walked out of the building and headed home.

I was mortified the whole way home, Emma had seen, and recognized, the chastity cage. Surely she wouldn't keep buying the fake bet lie that I had been telling her, and what kind of bet would involve me wearing a chastity cage and writing the word 'slut' on myself. And why the hell would I send her that picture?! That was something I couldn't get my mind off of, just what would Emma be thinking of me after seeing that photo. And more importantly, did she hear the sound bite playing on my phone on my way out?

This line of thought led me to another realization, Mistress had a ton of other voice notes that she could have saved from last night. She was obviously recording and saving the phrases to use as ways to further humiliate me. I tried to remember what else she had made me say as I entered my apartment.