Digital Dominatrix 2.0 chapter 14 (Patreon)

Digital Dominatrix 2.0 - chapter 14


“Whenever you hear the phrase ‘Good Girl’ you will feel the pleasurable sensations running through you. You need to be a good sissy. You need to earn your Mistress’ approval…”

The whispers seemed to be in my dreams, but then my eyes would open and I would still be able to hear them, whispering into my dark bedroom in the middle of the night, and I would just fall back to sleep….

—

Tuesday was mostly uneventful, Emma had covered for me at work again, so I spent the morning relaxing with minimal interruptions. By noon, I was finally able to remove the breasts from my chest after spending a good half an hour, soaping them up in the shower. They hurt a little as they pulled on the skin of my chest, but they were finally off!

I had to admit, after almost three days of walking around with the breasts, it felt a little weird for the first couple of hours without them. But it felt good knowing that I could show my face in public again and that I could go back to work tomorrow.


Shortly after midday, Mistress instructed me to get dressed in the maids outfit and insert my plug. Apparently, it was time for another clean up of the apartment. It didn’t take me long to get ready this time, and less than fifteen minutes later, I was fully dressed with the heels locked in place and the plug inserted.

I was reminded to maintain the proper posture when walking in the heels, but that had almost become second nature to me by now. I found it was more difficult to walk without the feminine sway than with it. As I cleaned the apartment, I was intermittently rewarded by the words ‘Good Girl’ accompanied by a pulse from the plug.

I was actually a little worried after vaguely remembering what happened last night with the repeated hypnosis trigger, but thankfully there were no glitches this time and I was able to finish cleaning up without issue…apart from the reinforcement of the trigger that is.

“Goog Girl.” ‘Bzzzt!’ “You are not permitted to remove the maids' dress, the heels, or your plug just yet. I have one more task for you to complete. I will provide further instructions soon.”

Well, that was a little unexpected, so I was just supposed to sit around fully dressed for a while. Wearing the outfit while cleaning or indulging in some sort of fetish play was one thing, but the psychological difference as I just sat there in the dress was palpable.

I was no longer ‘playing’ I was simply trying to go about my business while dressed up as a maid, as though this was my normal outfit. I decided to try and distract myself with a little gaming, but a game where the player's life was slowly being overtaken by a digital personality was probably not the best distraction for me.


Every time I adjusted my position on the sofa or moved to cross my legs, I was reminded of the humiliating outfit. My stockings would brush against each other, or the hands holding onto the controller would get lost inside the bunched up fabric of the outfit. I couldn’t concentrate enough on the game, so I gave that up and decided to do something else. Unfortunately, the dress, the plug, the heels, and the chastity cage were too much of a distraction for me to do anything.

Even going to the toilet came with its own distractions. I was used to sitting to pee thanks to the cage, but I wasn’t used to having to hold the frills and petticoats up out of the way as I did so. Eventually, Mistress spoke up again.

“Sissy, I have been tracking a package delivery that has now been completed. Please retrieve the delivery from outside your apartment.”

Well, thank god I didn’t have to answer the door dressed like this, I figured this must have been a smaller package, which was a relief to me.

I slowly opened the door and saw a package sitting inside the little drop-off cage on my door. I grabbed it and slammed the door quickly. Before I even had time to examine the delivery, Mistress spoke again.



“Sissy, it is time for the next phase of your training. Please be seated in front of your laptop, and bring your new delivery with you.” I was hoping she wasn’t planning on forcing me to watch another hypnosis video.

Thankfully, that wasn’t the case this time.

“Sissy, it is time for you to start learning how to apply makeup. In the package you have just received are all the supplies you will need. In a moment, I will load up a makeup tutorial video. You are to follow along with the video and do your best to apply your own makeup. I will be checking. Have fun, sissy.”

With that, the video loaded up, and I watched along whilst opening the package and emptying the contents onto the desk in front of the laptop. As it turned out, every item that was in the package matched what the girl in the video was using, this made it much easier for me to follow along, but I still wasn’t sure I was doing the best job of it.

I started with some mascara that I painted onto my eyelashes, giving them a thick, heavy look and feel. Next up was some sort of ‘correcter/concealer’, which was a creamy substance that I painted onto my cheeks, starting below my eyes before blending it into the rest of my skin. This was followed by some bronzer, which I was instructed to dot around certain places, a little blended in on my forehead and cheeks to give some definition. When I was done and the video had finished, I was told to send a selfie to Mistress for her to examine.

“A very good first attempt, sissy. Now, please find the makeup wipes in the delivery and remove all makeup before sitting back in front of your laptop for a second attempt.”

I did as I was told, and before long I was once again applying makeup along with the girl in the video, secretly praying there wouldn't be another glitch in Mistress’ code, I didn’t feel like spending five hours doing my makeup over and over again.

Luckily, that wasn’t the case today. By the third attempt, Mistress was happy enough with the results that I was allowed to stop practising. I was told to leave the makeup in place, though.

I examined the selfie I had sent to Mistress, and the makeup was subtle enough so that it didn’t completely transform me, but it was very obvious that I was wearing it. The bronzer highlighted parts of my face that didn’t usually draw attention, and the concealer hid any blemishes, giving my skin a soft, feminine glow. Add to this the fact that my eyebrows had already been plucked into a feminine arch, and I had a very girly looking face.

As I was just finishing up a little lunch, when Mistress informed me that I had a visitor, something I was not happy about, I wasn’t exactly dressed to entertain guests right now.

“Sissy, Kate is outside your door. I am granting her access now.” Fuck!

I heard the click of the electronic disengaging and saw as Kate pushed the door open and stepped into the apartment.

“Hey Mi-Hahaha, This is a lovely greeting. Hahaaa.” Kate’s speech was interspersed with fits of laughter as I no doubt caught her off guard with the way I was dressed. “I can see you’re making the most of your time off. Did you do your own makeup?”

“Yeah, I was just practicing, thought it would be fun…What do you want Kate?” I asked, a little more curt than I would usually be with Kate, but it had been a long couple of days.

“Well I was just coming to see if you needed anything before I left for work for the night. I figured you wouldn’t be able to go out with your boobs but I can see you don’t have that problem anymore. Although I doubt you’ll be going anywhere dressed like that.” Kate said, crossing her arms and eyeing my outfit.

“Oh, right. Thanks for thinking of me. That's ... .actually pretty thoughtful. But yeah I managed to get rid of the boobs, thank god because the bra strap was really digging into my shoulders.”

“That’s cause’ I’m a super lovely person, obviously. And now you know how I feel every day with these things.” She replied, gesturing to her breasts as she spoke.

“Yeah I guess so, anyway I’m all good for now. But thanks for offering, really. But I’m gonna get changed and go out to the store soon myself.” I wasn’t actually sure when I would be allowed to get changed, but Kate didn’t need to know that part.

“Fair enough. So you’ve been practicing makeup?”

“Well I was just bored and I guess I um…It looked okay when you did it the other day so I thought I’d give it a try myself ya know.”

“Hmm, well it’s not bad, but you could have used a little eyeshadow, draw attention to your eyes a little more, and I would have done something with the bridge of your nose, soften the shape of it a little. I’ll give you some tips next time.” She said with a smile, clearly she was trying to tease me.

“Yeah I’m sure you’d love that.” I replied.

“HA, I think we both know who’d love it, pantyboy! Don’t think I don’t remember how you reacted the last time. Speaking of which, I’m guessing you’re umm…locked today? What with the outfit and all?”

“Oh you mean the cage. Y-yeah I er, I am.”

‘Sissies should be caged.’ That small voice in my head again.

Of course I was caged, I need to be caged. My little sissy clitty was supposed to be caged unless a Mistress had use for it.

“Ha! I knew it. You’re so kinky, I love it. Anyway, I gotta run, but first...” Kate stepped in quickly and reached underneath my dress, grabbing at my caged clitty beneath the panties I had on, an act which caused it to try and swell inside its prison.

“Sorry, pantyboy. Just had to make sure, hope it’s not too tight for you. Bye!” And she was gone.


It took me a few minutes to calm my clitty down as Kate's teasing had done a number on it. Eventually, I was allowed to get changed into some normal clothes and remove the makeup. Panties and bra were still required, of course, but otherwise I was able to at least go out to the store to stock up on what I needed.

The rest of the day was pretty boring, apart from being reminded of the cage every time I tried to get hard. But as frustrating as it was to be denied a full erection, I was oddly comforted by its presence. I was really starting to feel like I needed to be caged.


—


I woke up on Wednesday, horny and tight in the cage as always. I was going back to work so I got up and showered before getting dressed. I was back in the black, womens pants and a white shirt with feminine trim. If no one looked too closely then I appeared like any other guy going to work. Unfortunately, Mistress wasn’t going to make it too easy for me today.

“Sissy, today you will be required to apply some makeup for work. You are to apply a layer of mascara to your eyes and send a close up selfie before leaving.” Dammit!

I should have figured this was coming, but I didn’t expect it to come around so quickly. I weighed up my options for a second, but I knew that disobeying Mistress at this point was futile, so I went ahead and applied the mascara to my eyelashes. I examined the photo before I sent it, I tried to convince myself that it wasn’t noticeable, but my eyelashes were thicker and drew attention to them, coupled with the eyebrows made it clear that I had a feminized face. I just hoped that I wouldn’t run into too many people.



“Hey Mike, glad you're feeling a little better.” Jake greeted me as I entered the office for the day.

“Yeah, hopefully, everything's good on your end too.” I replied as I headed to my desk. “Is Emma in?” She was usually the first one in the office, and I couldn’t help but feel disappointed that her desk was empty when I walked in.

“Not yet, must be running a little late today.” He replied. I noticed Jake’s gaze lingered longer than necessary on my face, no doubt he had seen the mascara, but thankfully he said nothing as I headed to my desk.

As I got myself set up at my desk I couldn’t help but repeatedly glance at the doors from the elevator, waiting for Emma to turn up. I had only seen her a couple of days ago, what the hell was wrong with me?!

My spirits lifted a few minutes later when I heard the elevator doors ping open and Emma walked into the office.

“Ah, the whole gang's finally back together. Everything okay with you, Mike? When I spoke to you the other day it sounded like you had something to ‘get off your chest’.” She emphasized the last four words of her sentence and ended with a smirk in my direction, but I don’t think Jake caught on.

I felt a little of the familiar embarrassed flush creep up my cheeks as I answered. “Oh yeah, I’m all good Miss Emma, thanks.” Jake looked over at me as I finished speaking, but I didn’t immediately realize why. Emma's smile got wider as she stared at me, then I realized what I had done.

I had called her Miss Emma in front of Jake.

“Well that’s good to hear, Mister Mike.” Emma replied with another coy smile but thankfully she moved to get set up at her desk so nothing further was said.

I had a little catching up to do so I was suitably distracted for most of the morning, Emma didn’t seem to have that problem however, as she came wheeling over to my desk after an hour or two.

“So, you’re calling me Miss Emma at work now too? I like it. Maybe you should keep it up.”

“That was a mistake. Won’t happen again.” I said.

“Aww that’s too bad. But that’s not the only change I noticed today, are you wearing mascara?” She asked me, staring intently at my face.

“Oh, yeah. Mistress made me practice makeup yesterday.”

“Ha, that’s so cute. Maybe next time you should try that lipstick I gave you.”

“No thank you! The mascara is bad enough, I’m pretty sure Jake saw it too. Did you manage to find a way to get rid of the program? This is getting out of hand.”

“Oh come on, Mike. Don’t act like you’re not having fun. And no, I haven't had the chance to look into anything, I really need to be at your computer to be able to get anywhere. The Mistress program has been running for a while now so its code and memory will have all been compiled based on your actions and inputs.”

“Right, that makes sense.” I said, but even despite how much fun I had had with the Mistress program, I knew I needed to get rid of it at some point, preferably before I became completely sissified. “Are you free after work maybe? You could come over to my apartment and have a look on my laptop, see if there's anything you can do.”

“Well I guess I could, but it is a little out of my way.” Emma replied, before adding. “What’s in it for me?”

“Anything!” I answered way quicker than I had planned to, but it wasn’t a lie. By this point, there was very little I wouldn’t do for Emma.

“Anything huh? Well I like the sound of that. Okay, sissy, I’ll come by your house a little later this evening. Make sure you tell your Mistress when you get home that I’ll be stopping by.”

“Yes, I will. Thank you Miss- err, Emma.” I replied, eagerly, prompting Emma to say the two words I had secretly been longing for her to say to me.

“Good girl.”

I swear I felt my eyelids actually flutter a little at hearing those words and my clitty pressed extra hard against the unyielding material of the cage.

“Haha, whoops. Sorry, Mike. I forgot about that trigger, looks like it’s still working though.” Then, Emma leaned in close so she was whispering almost directly into my ear. “That will come in handy later, won’t it, sissy?”

“Yes. I love it when you say it.”

“I know you do, so you’re going to be good for me tonight, right? You’re going to be my good little sissy when I come over?” She asked me.

“Yes, Miss Emma. Of course.” Emma was so close that I could barely think, it seemed the closer she was to me, the more turned on I got.

“Good Girl”

“Hmmm!” I had to slam my mouth shut to stop the desperate, slutty moan that almost escaped my lips when she said it again. My whole body was vibrating with arousal and pleasure as the trigger words did their thing. For some reason, they felt 10 times more powerful coming from Emma than they did over the speaker.

Eventually, Emma had had her fill and left me alone, a panting, red-faced and horny mess. It took a full five minutes and a trip to the kitchen before I was able to concentrate on anything but Emma.

—

As I packed up my desk and headed out of the elevator, Emma called out to me.

“I’ll be over at your house around seven to help you out with your little problem, Mike.” I noticed Jake look over at me as Emma spoke, did she really have to make it sound juvenile and embarrassing?

“Oh right, my laptop thing. Yeah thanks. I’ll see you at seven, bye.” I headed out before she could say anything else.


A short while later, I was back at home and being greeted by the AI that was slowly, but effectively, sissifying me.

“Welcome home, sissy. I hope you had a good day at work.”

“Hello Mistress. It was fine, thanks. I should let you know though, Miss Emma will be coming to visit at around seven tonight.”

“Very well, sissy. I will leave you be for now. I will contact you when it is time to prepare for Miss Emma’s visit.”

I wondered what she meant by ‘prepare’. I didn’t really plan on preparing in any way, but given the reason Emma was actually coming over was to see if she could deactivate the Mistress program, I wasn’t going to protest too much.


I made myself a light snack and managed to chill out for a couple of hours before Mistress spoke up again.

“Sissy, it is time to prepare for Miss Emma. I would like you to make a good impression on her. Please retrieve the following items from the bag you brought home from Emma a while ago….”

I listened as Mistress told me what items to look for in the bag that Emma had given me. I did wonder how MIstress knew what was in there, but I’m guessing Emma had told her at some point via the messenger app she was using. Mistress must have built an itinerary of sorts.

The items I was searching for turned out to be a complete set of incredibly frilly pink lingerie. There were sheer pink stockings that would run all the way up to mid thigh, the tops of which were lined with a lacy pink trim. The stockings would be held in place by a pink garter belt with clips, as opposed to the stay up tops I had mostly been wearing in the past. The set was completed by a pink bra that had cups that were lined with more lacy pink frills. The whole ensemble would drown me in femininity, and I couldn’t wait to put it on for Emma.

“Good work, sissy.” Mistress said as she used the security cameras to make sure I was dressed properly in the pink lingerie. “Now, fasten your bathrobe around yourself for now and take a seat at your laptop. Make sure your makeup supplies are all within reach.”

So I was now once again back in front of my laptop as I watched another makeup tutorial video online. This one was a little different though. Apparently, I was giving myself a ‘candygirl’ makeover. From what I could gather, the candygirl look centered around all things glittery and girly. It started with my eyes, they were lined with a coat of pink and the mascara I was instructed to use was also pink, before a brighter, more noticeable color was used along with the corrector from yesterday. This gave my face a noticeably pink hue whenever my cheeks or nose caught to light. The whole look was rounded off by a coat of the shiny, pink lip gloss that I had brought home from the weekend with Emma, which once again caused my collagen infused lips to plump up far more than they should have done.

I used my phone's camera to check out the job I had done and sent the results to Mistress when I was happy with the job I had done.

“Good job, sissy. Now you are to kneel in the centre of the living room, exactly as you are now, with your head bowed. When Miss arrives, you should welcome her properly. Make sure to kiss her feet when you do.”

“Okay, so I should keep the robe on?” I asked.

“For now, yes. I want your new look to be a surprise.”

And so I waited. On my knees in my living room with my painted pink face bowed until Miss Emma arrived. The longer I spent there on the floor, the more turned on I became. Just the act of kneeling and waiting so submissively like this was a turn on, and then there was the fact that it was Emma I was waiting for, and lately just the thought of her was enough to get my blood pumping.


After who knows how long had passed, I heard the sound of my door lock disengaging and Emma entered. I kept my head bowed low as instructed, knowing Mistress would probably be observing me.

“Well, isn’t this a nice surprise? Do you greet all your visitors like this, Mike?” Emma said, stepping close to me, close enough that I could see her black shoes on the ground near where I was kneeling. I remembered Mistress’ instructions and leaned forward, planting a kiss on the tops of both of her shoes. I heard a faint ‘hm’ come from above me as Emma let out a sound that sounded like approval.


“Good girl. But why the robe?” Emma asked as I was overcome by the sensations caused by that phrase.

“I…..Guess, I wanted to surprise you with what’s underneath.” I replied, suddenly feeling overcome by nerves as I wondered what Emma would think of the underwear I was wearing.

What if she didn’t like them? What if she laughed at me? What if I had completely misread the intentions of her visit?

All these thoughts swirled around as Emma told me to stand up and show her what I was wearing.

“Oooh, did you now? Well that sounds exciting. And look at this, you even did your makeup special for me. Love the touch of pink.” She said as she took in my face for the first time.


Well if she liked the makeup then I figured she would love what’s underneath the robe. I untied the belt in front and let it drop to the floor, allowing Emma to take in the sight of me in the pink ensemble.

Her eyes widened in shock as she looked me up and down, and I could see her smile widen and turn into something predatory.

“Did you wear this for me, Mike?” She asked.

“Y-yes Miss, you like?” I asked, noticing a different look on her face when I spoke, a look of pure lust.

“...Like? Sissy, I love!” She grabbed me hard behind the neck and roughly pulled me forwards into a kiss. Her hands were all over me, caressing and squeezing as she kissed me forcefully, her tongue invading my mouth and her lips crushing against mine.

“Oh, Mike. You’re such a ‘Good Girl’.”

The combination of her words and her aggressive groping and squeezing of me had me more horny than I’d ever been. My knees damn near buckled as waves of arousal and pleasure coursed through me.

When Emma finally broke the kiss, she still had that wild fire in her eyes as she held me close to her.

“Bedroom. Now.” I immediately obeyed.

“Yes Miss.” I led the way to my bedroom, Emma gave me a sharp smack on my pantied behind as I did.

I heard the sound of Emma unzipping her skirt behind me and letting it fall to the floor.

As soon as we walked into my room, Emma roughly shoved me onto my bed and mounted me. Her crotch was grinding against mine as she kissed me again and I was lost in a haze of eroticism.


“If only you weren’t caged right now sissy, I’d be riding you so hard. But that’s not what someone like you really wants, is it?”

Was that what I wanted? It certainly felt like I did, my cage had never felt tighter.

“No, that’s not what a sissy like you wants, is it. What you really want is to serve a powerful Mistress like me. Isn’t that right?”


“Y-yes Miss. I exist to serve you. Please let me serve you, Miss Emma.” I knew what to say without having to think.

“Tell me what you are, Mike.” She told me, while staring straight into my eyes, it felt like I was being x-rayed, like she could see straight into my soul.

“I’m a sissy. I’m a good sissy who wants to serve you.”

“Good girl.”

“Ohh, yes. I am a good girl.”

“And what’s this?” Emma asked, reaching down to grab hold of my cage while I was still laid beneath her.

“It’s a chastity cage Miss. It keeps my sissy clitty safely locked away until someone has use for it.”

“And do you like it? Do you like having your little clitty caged like this?”

“Yes Miss. It’s frustrating, and it makes me desperate but it feels good to be denied.” What the hell was I saying? Is that really how I felt?

“Would you like to please me now, sissy?” Well that was an easy question to answer at least…


“Oh yes, Miss Emma. I would love to please you!” I answered, the eagerness obvious in my voice.

“Then get to work!” Seconds later, Emma had crawled upwards until she was mounted squarely on my face. Her crotch had barely made contact with me before I started licking….

—

It didn’t take me long to get Emma off, I was used to this by now.

When she had finished enjoying herself, she rolled off of me and laid next to me on my bed, my face was covered in her juices but I made no move to wipe them off. I felt marked by her, used….wanted.

“Sissy, do you have a dildo and/or a strap on harness in your apartment?” Emma asked me.

“No Miss Emma, the only thing like that I have is my plug.”

“Get one. I’m going to want to fuck you again, sissy.”

“Yes Miss Emma.” I said, memories of the last time she had done so came flooding back, turning me on even more.”

“Good girl. Are you turned on, Mike?”

“Yes MIss, extremely.” I replied, honestly.

“And would you like to cum?”

“God yes. But I can’t. Not with my cage.” I said, longingly.

“Oh I know, but you have been so good lately that I would love to be able to give you a little treat. I’d be sure to lock you right back up of course.”

“Oh please Miss. That would be great. I’m so horny right now, especially after….you know.” I said.

“Haha, yes I would imagine you are. Unfortunately, I’m not the one with control of your cage. If I were then I’d be happy to let you out for some fun.” Dammit, I knew that Emma couldn’t let me out but just talking about it had gotten my hopes up a little.

“Ohhh fuck, Miss Emma. I wish you were in control of this damn thing.” I replied, squirming in pent up arousal.

Emma replied by leaning close to my face and saying two simple words that sent another shiver through me.

“Me too.”

“But anyway, I believe you asked me here to take a look at the Mistress program. So while I do that, you can lay here on the bed looking pretty and trying to control that little clitty of yours.” Emma said, standing up from my bed and doing nothing to cover up her lower half. “Oh, and here, this should keep you entertained while I work.” Before I knew what Emma was referring to, her hand had reached towards my face and quickly pushed something into my mouth, a small ball of fabric that tasted like…..her!

“You can keep those clean for me while I work. And don’t move from the bed, I like you like that.”

And so that’s how I spent the next hour or so, lying on my bed with my face coated in Emma’s sex and sucking her flavor out of her underwear.

At least maybe I would make some progress towards getting rid of the AI, the question was, what would I do without it?


End chapter 14