Digital Dominatrix 2.0 chapter 8 (Patreon)

Digital Dominatrix 2.0 chapter 8


I woke up the next morning with the all too familiar tightness from the cage on my cock. Once again I had vague memories of waking up during the night and hearing that strange voice, the voice that seemed to be present whenever I was in bed lately.

I dragged myself out of bed to get dressed in an effort to take the focus off my locked up cock, but that was difficult to do as I was reminded of my current situation as soon as I opened my underwear drawer. My boxers were all gone and all I had to replace them was a growing selection of feminine underwear. Just the feel of the panties sliding up my smooth legs as I got dressed for work was enough to have me pressing hard against the electronic cage.

I had always had a bit of a thing for panties, that’s probably no secret by this point, but lately it felt like it was getting more intense every day. This was especially true in the mornings when getting dressed. Did it have something to do with the strange voice I could hear in my sleep?

Or maybe it was just because I am sissy, and sissies love panties….

“Woah!” I said out loud, shaking my head and silently admonishing myself for letting me think that way. All this fem stuff was really starting to take over.

Thankfully, Neither Emma nor Mistress had given me any specific instructions to go back to work in a skirt today, which meant I was free to dress in what was now my ‘regular’ work attire. Even though the tight pants and the smooth blouse type shirts were made for women, I still looked androgynous enough to not feel out of place as I left my apartment.

I was wearing a light blue shirt that sat loose enough so as to not show my bra straps, and the plain black pants with a red thong underneath, the thong came from the duffel bag Emma had ‘gifted’ me.

I got to work to see that it would be just me and Emma again as Jake would be out for the rest of the week. Hopefully, the extra workload would keep both of us busy enough so Emma couldn’t torment me as much.

“Morning sissy!” Emma greeted me, loud and enthusiastic.

“Shh! Could you not call me that at work?” I said, reflexively shushing her.

“Why not? There’s no one else here, Mike. Or did you forget?”

“I didn’t forget, it’s just unprofessional.” I said, trying to act nonchalant, as though she wasn’t turning me on with nearly everything she did or said lately.

“Oh really? Was it ‘unprofessional’ when you were underneath my desk with your tongue in my pussy the other day? Is it considered ‘unprofessional’ for a man to wear panties and a chastity cage to work? What about the butt plug?” Emma replied, a smug look on her face.

“....You know what I mean!” I said, quickly turning away and heading over to my desk, causing Emma to giggle.

“Awwww, don’t be a pouty sissy, Mike. We have the office to ourselves. If you’re a good girl, maybe I’ll let you back under my desk before you go home.” She said, walking over to her desk with a satisfied smile. The subtle twitch of my hips as she spoke about me being back under her desk indicated that she had won this round. As soon as she had made reference to me having my head between her legs again it was all I could think about.

It quickly became clear that without Jake here, Emma didn’t need to wait for an opportunity to tease me at work. She didn’t need to slide over to my desk to take a quiet jab at me, she could just call them across the room.

“It’s a pity you didn’t wear the skirt again today, show off your legs some more.”

“Skirts to work was a one time deal! Not happening again.” I said, earning a response that was too quiet to make out properly, but it sounded a lot like ‘we’ll see’. “Anyway, could you keep your perverted thoughts about me to yourself for a while, I’m trying to work here.” I added, flipping the narrative back on her for a second.

“Oh I’m the pervert? I’m not the one who installed an illegal program onto my digital assistant and got myself stuck in a chastity cage and panties!” She had me there I guess.

“Yeah, but I was trying to keep it to myself, you’re the one who got so excited by it that you made the whole thing worse!”

“Oh please. While I admit I find the idea of you all sissified and servile a turn on, there’s no way I find it more exciting than you do. I’ll bet you’re probably trying to get hard in your cage just talking about it.” Emma finished by staring directly at my crotch with an inquisitive look. Of course she was right, the whole topic was a turn on for me and she knew it, I could even feel the heat starting to flood my cheeks as I willed myself not to be turned on.

“I thought so.” Emma added in a satisfied tone.

“Whatever! Can you just let me back to my work please? We both have a lot to get through.” I replied, a little petulantly. I expected Emma to retort with more teasing, but thankfully all she did was mutter out a quiet “Fine.”, before turning back to her work.

She sounded a little annoyed, but at least it gave me a chance to try and refocus. I returned to my own work for a while and was just starting to get into a decent rhythm, when I was distracted once again, this time by my phone vibrating with a message from Mistress.

‘Sissy, it is time for a panty check.’ I thought that was weird, since the various cameras had been installed, Mistress hadn’t felt the need to ask for one of her ‘panty checks’. I was just contemplating sneaking off to the bathroom when another message popped up below the previous one.

‘As you failed to wear your bra when leaving the apartment yesterday, you are required to ask Miss Emma for assistance with this panty check. She may use the messaging software on her phone to send through photographic proof of your compliance. You have thirty minutes to complete this task.’

Oh great, I thought to myself. Here I was trying to deflect, defend or otherwise avoid Emma’s teasing and Mistress was forcing me to put myself right back into the middle of it. I considered disobeying for a brief second, but the thought of what Mistress could do with all the blackmail material she had was too scary to risk.

So with my face burning red in embarrassment, I stood up and headed over to Emma’s desk, she spoke before I had gathered up the courage to ask anything.

“What is it, Mike? We both have a lot to get through, remember?” She said, barely looking away from her screen.

“Umm, I kind of need a favor..” I said, waiting for her response as I tried to make out how difficult Emma was going to be on this one.

“Well, what favor? I’m pretty busy here, you know.”

“Yeah I err…I kind of need you to check my underwear for Mistress.” My voice trailed off to a quiet mumble at the end, so much so that I was certain Emma would not have understood what I said.

“What was that? You’re going to have to speak up, Mike, and don’t mumble so much.” She said, finally turning her chair to face me.

“I said … I need you to check my underwear for Mistress.”

“Oh really. And if I say no?” Emma had folded her arms over large chest, keeping up the annoyed facade, but I could clearly see the corners of her mouth had started forming into a smile.

“Then I guess I will get punished in some way by Mistress.”

“Well, like you said Mike, my getting involved just made the whole thing worse. So I think it’s best if I stayed out of your business.” Fuck! She was not going to make this easy.

“Please Emma-err Miss Emma I mean. Please! I really don’t want to risk any more punishment from Mistress and she said that I have to ask y to help with this panty check.”

“Right, so now you want my involvement because it’s convenient for you, you mean?”

“No, that’s not it I … I like having you involved, I really do.” I said, I wasn’t exactly lying either.

“Really? Why? Why do you like having me involved?” She asked, idly swivelling from side to side on her chair. She was clearly making a meal out of this.

“Well you're hot for one, and err, I like that you seem to understand my kinks and haven’t reported me to someone for being weird.”

“Well I’m flattered you find me attractive, but what specifically have you liked about my involvement so far, Mike?”

“I guess I didn’t hate it when I was um, ya know. When I was your maid I mean.” I mumbled out my truthful response, staring at my shoes the whole time.

“Go on.” Emma prompted me, clearly wanting to hear more as her smile got wider.

“And ya know, I liked serving you I guess. I even didn’t mind it so much when you spanked me, or getting to go down on you … both times.” Surely that had to be enough.

“Ha! I can already tell how much you love it, sissy. I’m just glad you’re coming to terms with it. But if you really want my help to avoid punishment, you’re going to have to beg me properly.”

“H-how?”

“Well you should be on your knees for a start.”

“Are you serious? What if someone comes down here again?” I asked, still apprehensive about my fetish being exposed at work like this.

“Then I’d suggest you hurry up.” She had me over a barrel and she knew it. Once more, Emma had something I desperately needed, and she was making me work to get it.

Seeing no other option, and with time ticking away, I lowered myself to my knees next to Emma’s chair. She had the chair swivelled away from her desk so that she was facing me, at least I wasn’t trapped underneath her desk this time.

Not knowing what else to do next, I clasped my hands together in front of me and begged for her help.

“Please Miss Emma, please help me check my panties! I can’t afford another punishment, there’s no telling what Mistress might do next.”

“Very well, seeing as you asked so nicely, but you owe me one … another one that is.”

“Of course, anything you want.” I said, desperately as my cock pulsed angrily in the cage, desperate for some attention.

“We’d better find somewhere private.” Emma said, standing up from her chair so that she towered over my still kneeling self.

The ‘somewhere private’ turned out to be a seldom used storage closet at the back of the floor, near where the doors to the toilet’s were. It was large enough that Emma and I had plenty of room to move around in, but small enough to make sure that we were both standing pretty close together. The room itself only contained a few random pieces of cleaning equipment that were only ever used by the cleaning crew after hours.

“So I expect I’ll need to take a photo of you in your underwear for Mistress to review?” Emma said, still with a hint of a smile in her voice.

“Yeah, that's pretty much it.” I replied, wanting to get this over with quickly. “You need to send it to the messenger app on your phone.”

“Ooh that means I'll have another nice photo to add to my collection.” There was really no point arguing about that at this point. Not with all the photos she already had.

“Good for you. Can you please just send the photo?” I asked, lowering the front of my pants so the panties were clearly visible, as was the outline of the chastity cage. I should have known Emma wouldn't want to make it too easy for me.

“Oh come on, Mike. We need to make sure the picture is good enough for your Mistress don't we? Better strip down to just your underwear to make sure.” Emma said with glee, prompting me to grumble something in response. I would have argued more but the clock was ticking and I needed her help.

I unbuttoned the shirt and carefully pulled it away from my top half, leaving my bra exposed to Emma's hungry gaze. The pants soon followed, and I was now standing in the cool air of the store room as Emma eyed me from top to bottom. My smooth, still tanned body on display in nothing but a bra and panties. Perhaps even more humiliating, in an attempt to hide any panty lines, I had gone with thong underwear for the day, which offered very little coverage.

“Very nice, sissy.” Emma said, raising her phone and snapping a few pictures, way more than was necessary.

“Whatever software the program uses has been pretty accurate so far, you know. You don’t have to take so many pictures.” I said, a little annoyed.

“Well we need to make sure I get it right, wouldn't want you to get punished now would we?” Emma said, in a voice that hinted at the exact opposite. “Now, turn around so I can get a photo from the back.”

“Emma, I don’t think we need a photo from the back! Will you please just send the pictures you have?” I said as my clitty ached in its cage. Clearly this whole situation was turning me on. Perhaps it was the forced close proximity, Emma’s teasing, either way I knew I would be desperate for time out of my cage by the time I got home.

“I don’t think you have enough time to argue with me, Mike. Now turn around and let me see that cute behind.”

“Fine!” I said, turning so that my back was to her, showing off my ass which was almost completely exposed by the small thong I had on.

“Very nice! If a little slutty.” Emma mused as I heard the shutter of her camera app a few more times.

‘Slap!’ “Hey!” I jumped a little as Emma landed a sharp smack to one of my ass cheeks.

“All done, sissy. I’ll let you get dressed and out there.” Emma said, quickly exiting the small room before I could say anything else. I grabbed my shirt and pulled it back on quickly to hide the bra from view, buttoning it up slowly as I tried to distract myself from my own needy cock, but when I went to retrieve the pants, I noticed they had disappeared! Fuck.

I opened the door a crack and peered out of the small room across the office, I saw Emma with her back to me at her desk, she must have rushed straight back to her desk and made a show of being deeply engrossed in her work.

“Emma!” I said, loudly enough that she should have heard me, but not quite shouting. She did not respond.

“Emma!” I called a little louder, again to zero acknowledgement on her part. Was she really going to make me walk over there without any pants? Was she really this immature?

I took a second to study the area that led to the elevators to make sure no one would appear as I walked through the office with bare legs and in panties. We almost never got any visitors but knowing my luck…. Fuck it! I walked out of the small room with my heart pounding, even though I knew the floor was empty except for the two of us, it still felt weird to be walking through my workplace like this.

As soon as I made it to the side of Emma’s desk, she turned away from her screen and finally spoke to me.

“Oh! Hello, Mike. Didn’t hear you coming.” She said, barely suppressing a snicker.

“Could you be any more childish?!” I said, trying to admonish her, probably not the best idea given my current state.

“Whatever do you mean? I must say it’s very ‘unprofessional’ of you to be walking around the office in just your panties.”

“Just give me back my pants.” I said, holding out my hand.

“Say please.” Came her reply, causing me to seethe inside, thankfully I kept myself from reacting too much.

“Please.” I said through gritted teeth. Emma enjoyed the sight of me for a few seconds without saying anything before finally returning my pants. I snatched them from her hand and stomped back over to my own desk, Emma chuckling as I did.

I pulled on the pants and made to get back to work, once again forcing myself to focus on anything other than my constant arousal and humiliation. Unfortunately, it didn’t last that long. Just as I was loading up a spreadsheet, my phone vibrated with a message from Mistress.

‘Sissy, you have failed to provide the required panty check photos within the time limit. You have earned a punishment. You have ten minutes to convince Miss Emma to provide the photos.’

What?! This can’t be!

“EMMA!” I said loudly, causing her head to snap in my direction.

“Yes, sissy?”

“Mistress didn’t get the photos! What the hell?!” I said accusingly.

“Oh dear. I must have forgotten to press send on the message.”

“Are you fucking kidding me? We have no idea what she’ll do as punishment. She could destroy my reputation. How could you forget to send the damn photos?” In hindsight, it probably wasn’t the best idea to be venting my frustration on Emma. For all I knew it really was an accident.

“Calm down, Mike! It was a simple mistake. Perhaps I was too distracted by the pantied sissy to concentrate on anything else. And I don’t appreciate being yelled at by someone at work.”

“You’re right, I’m sorry. But could you please send the photos to Mistress? Apparently I’ve already earned a punishment.”

“There. Sent.” Emma replied, stabbing at her phone without saying anything else.

Emma seemed a little annoyed and didn’t say much of anything for the rest of the day. I resolved to just let her be and get some work done for the rest of the shift. All I saw her do besides work was type a few messages to someone on her phone.

“See you later, Emma.” I said, packing up and heading quickly out of the office. Emma replied with a cursory ‘see you tomorrow’ and let me leave without issue.

A short while later, I was once more flashing my bra and panties to my doorbell camera just to be allowed into my own home.

“Welcome home, Sissy.” Mistress voice came from the living room speaker as soon as I entered. “Unfortunately, you failed to complete an instruction on time today, which means you will have to be punished in some way.”

“I know Mistress, but that wasn’t my fault. Emma took the photos in time but she forgot to send them through that’s all.” I said, even though I knew there was no chance of appealing to the sense of reason of an AI program.

“I am not interested in excuses, sissy. You have one hour of free time before I begin your punishment.”

Shit. At least she didn’t send out any more photos this time, but I didn’t know if that was a good thing or not. I spent the next hour getting changed out of my work clothes, deciding to leave the underwear in place for now as I wasn’t sure if I would need them later. Besides, I didn’t have any male underwear to change into anymore anyway.

Exactly one hour later, Mistress spoke up again just as I was finishing a quick sandwich.

“Sissy, it is time for you to face punishment for your behaviour today. Begin by inserting your butt plug and retrieving the remote handcuffs before heading into your bedroom.”

Looks like I was in for more teasing, maybe even some more humiliating repetition tasks?

I took a minute or two to lube up and insert the plug as instructed before heading into my bedroom, no doubt to secure myself to my bed once more. The plug gave a short ‘bzzt’, no doubt Mistress testing to make sure it was inserted as instructed.

“Very good, sissy. You must now strip down to just your underwear, before putting on and locking your heels onto your feet. We will move on when the keys to your heels are safely secured inside the lockbox. You have ten minutes to complete these instructions.” Would I be walking on the treadmill again then?

I decided not to focus too much and just do as I was told before getting into any more trouble. I locked the high heeled shoes onto my feet with the small padlocks and dropped the keys inside the small digital lock-box that Mistress had bought. Looks like she was really trying her best to use every toy she had bought so far. I had a bluetooth controlled vibrating plug up my ass, high heels locked onto my feet, and was waiting to be told what to do with the electronic handcuffs.

“Very good sissy. Now that you are prepared, please secure yourself to your bed with the handcuffs. You will be released when your punishment is complete.” I wondered when that would be, would I just be teased with the plug for a while? Maybe I would be forced to repeat sissy mantras or listen to more sissy hypnosis videos.

As I pondered this, I secured myself to my bed and waited for something to happen. My hands were cuffed above my head with the chain of the cuffs threaded behind one of the lats in my headboard as I waited. I was fully expecting the plug to just kick into life, I was actually really hoping it would, the humiliating position I was in had my sissy clitty trying to get hard in the cage again.

“Now, sissy. I will not be in charge of when you will be released from your punishment today.” Mistress said, surprisingly.

“W-what do you mean? If you’re not then who is?” I asked.

“This punishment will be finished when Miss Emma decides it is. She told me about your little outburst today. Your attitude towards her was unacceptable, I have assured her that you will be apologizing to her this evening.”

I wondered what she meant by that for a few seconds, when I got my answer.

“Hello sissy. You look like you’re a little stuck there.” It was Emma’s voice, coming loud and clear from the speaker of my laptop.

I craned my neck towards where the laptop was to see Emma’s face lighting up my screen on a video call. She had a glass of wine held in one hand, clearly she had been waiting for a show.

“Emma! What is this? Can you see me?” I asked.

“I certainly can. Your mistress is kindly streaming the footage from your bedroom camera to my PC. I told her about your little tantrum earlier, and she assured me that she would make sure you apologized to me.” I turned my head to look up at the camera mounted on the wall near the ceiling of my bedroom, the camera that meant Emma would be able to see everything perfectly clearly. Well if all I needed was to apologize then I would happily do so.

“Emma look. I’m really sorry that-”

“MISS Emma.” Emma interrupted me.

“Yes, right. Miss Emma, I’m really sorry about earlier at work. I was just frustrated because you forgot to send the photos. But I see now that it was a mistake anybody could make, and I shouldn’t have gotten angry with you. Can you please forgive me?” I voiced my apology with as much sincerity as I could muster.

“Hmmm. Maybe I could. But first we need to make sure you understand that your behaviour was unacceptable.” Emma replied through the laptop speaker. “Plus, I tuned in expecting a show, it would be a shame to release you so early. Mistress, can you hear me?”

“Yes, I can hear you clearly.” Mistress replied to Emma, it was weird to have two people in a room conversing with one another without actually being in the same room, but the laptop speaker coupled with the bedroom smart speaker made sure that it wasn’t an issue.

“Oh good. I think our sissy needs some teasing.” Emma said, causing Mistress to fire up the butt plug.

I was already incredibly horny after the day I’d had, so it didn’t take long until I was writhing on the bed as the plug teased away in my ass.

“Mmmm, I do love watching you squirm on the bed, Mike. Now tell me, what are you?” Emma said as I tried to thrust my ass into the bed to increase the sensations of the plug. I knew what she wanted to hear, and I wasn’t in any headspace to resist.

“I’m a sissy.” I said, desperation obvious in my voice.

“I know you are. I just love hearing you say it while squirm on the bed, and in heels too! Such a slutty girl you make, Mike.” Emma continued her teasing as the plug vibed softly in my ass, I was desperate to cum but the plug was not vibrating hard enough to get me there.

“Yes Miss Emma! I am. I’m a slutty sissy! Please turn up the plug” I begged as my hips drove into the bed, trying to effectively fuck myself with the plug. I would have said anything to cum at this point, and Emma knew it.

“Hahaha It feels so good to hear you say that, sissy. Oh I wish you were here right now, your head between my legs, lapping away at my kitty. Would you like that, sissy?”

“Yes! Yes Miss Emma I would love that. I would love to your lick pussy again, please.” I responded, truthfully. If Emma were here right now while I was this horny I would dive between her legs so fast I would give myself whiplash.

“Mmmm I know you would, sissy. It’s a shame I’m not there with you right now. But I’ll bet you can picture it can’t you? Picture yourself burying your face in my pussy.” My head filled with visions of servicing Emma with my mouth, I would have done anything at this point to taste her once again. I would also do anything to cum.

“Tell me again what you are, Mike! Tell me how much you love it.” She said, her voice sounding breathy and seductive.

“I’m a sissy! I’m a sissy and I love it!” I said, not lying at all by this point.

“What do you love, Mike? Tell me now. Confess to me how much you enjoy being a feminine plaything for others to tease and enjoy!” The plug's vibrations increased a little as Emma finished speaking, pushing a little closer to the orgasm I so desperately needed.

“I love it all … Fuck! I love wearing panties and bras and all things girly and sexy. I love being a sissy. I love when you tease me Miss Emma. I love serving you and being your sexy maid. I love being caged and desperate. Please Miss Emma, please tell Mistress to turn up the plug!” I begged and confessed, saying things I thought Emma would like to hear, I was too far gone to care at this point.

“I could tell her to turn up the plug, but this is supposed to be a punishment, remember?” Emma said.

“Please Miss Emma. I’m really sorry. I’ll do anything to make it up to you. Please!” I begged.

“Anything to make it up to me, Is that right, sissy?”

“Yes, yes. Anything, I’ll be a good sissy girl for you. Please”

“Well, I’ll remember you said that, but I don’t think you should be allowed to cum tonight. Not after you yelled at me in the office. Mistress, stop the plug.”

“Nooo!” I cried out as the plug’s vibrations ceased almost immediately, leaving me desperate, just a few seconds away from tipping over the edge into an orgasm I so desperately needed.

“Now, sissy. I have to go ‘take care of something’, and I’ll be watching this recording while I do. Bye bye sissy…Oh, and Mistress. Give our sissy something ‘fun’ to listen to for a while will you?” With that, Emma’s face disappeared from the laptop and the room went quiet. But the silence didn’t last long. Mistress did what Emma said and gave me something to listen to.

“Relax, sissy. Relax and enjoy this recording as you explore your sissy desires….” Another hypnotic recording began playing as I remained firmly locked to my bed with no choice but to listen as the soft, soothing voice seemed to seep directly into my brain.

“....You are a sissy, you can’t fight it anymore. You can’t hide from what you are. You love panties, you long to feel pretty and be used by your superiors. You exist to serve and pleasure others as you remain chastised like a good sissy. You are a good sissy aren’t you?”

“..Yes. I’m a good sissy.” I found myself following along with the voice on the recording without being prompted.

“....Good girl. You are a sissy…” Something about being called a good girl and a sissy, was having an effect on my already desperate clitty. All the voices I had heard in my sleep, all the recordings, all the teasing. It was clearly having a profound effect on my psyche, I could feel my mind slipping away into a haze of pink and frills. I really am a sissy….

I found myself listening along to the recording and speaking when prompted, I wasn’t sure how much time had passed or how long I lay there. I didn’t even realize when the cuffs opened, the rest of the evening passed in a blur. I moved around my apartment in horny stupor, unable to focus on anything but my own humiliation and debasement. Every now and again Mistress' voice would speak out to ask me questions.

“What are you?” Would play out of the smart speaker. “I’m a sissy.” I would answer, almost automatically, I was saying it and hearing it so much by this point that I was really starting to believe it. I was still wearing the heels, Mistress had not released the keys from the lockbox yet and I was starting to feel a lot more confident moving around in them.

“You love your panties, don’t you?”

“Yes Mistress. I love my panties.”

“Do you have a cock, sissy?”

“No Mistress. I’m a sissy, so I have a little sissy clitty.”

The rest of the evening passed in this way, I ate some dinner, only stopping to answer more questions from Mistress. I turned on a movie, hoping it would distract me from the need in my crotch. Every now and then Mistress would interrupt the movie with another question that I needed to answer, until finally, it was time for bed.

Mistress released the keys to my heels before I got into bed. I gave my calf muscles a small rub as I removed the heels that I had been wearing for the last couple of hours.

I drifted off to sleep as I thought about what tomorrow might bring. I knew I would be playing the part of a maid again, this time for Kate, but what would it be like at work? These thoughts ran through my mind as a low voice started coming from somewhere in the room.

….”You are a sissy.”



End chapter 8.