Digital Dominatrix 2.0 chapter 6 (Patreon)

Digital Dominatrix 2.0 chapter 6


My sleep last night was uncomfortable, to say the least. I was constantly being woken up by my aching cock in its cage. What's worse, everytime I woke up was accompanied by the feeling of Miss Emma's warm, barely dressed body, sleeping soundly beside me. I could feel her warm, soft skin brushing against mine whenever I tried to roll over or adjust myself. Not to mention the silky smooth material of the nightdress I was still wearing.

I opened my eyes earlier than usual to hear the sound of Emma encouraging me awake.

“Rise and shine, sissy. Time to get ready for the day.” Emma said in a cheerful voice, dragging the covers off of me. The night dress had ridden up and bunched around my waist, exposing the matching shorts I was wearing with the cage clearly visible in the crotch. I sat upright in bed, rubbing my eyes and mumbling a response.

“Wha time ‘s it?”

“It’s time to get you dressed for work, sissy. I’m sure this is a little earlier than you’re used to but we have a little overtime to do today remember? No Jake.”

“Yeah, right. I’m coming.” I said, swinging my legs off the bed, Emma still had her own nightwear on, but had added a long silken gown to add a little more coverage. I briefly wondered if she was still wearing nothing underneath, as she had been last night. But that train of thought was not helping my arousal levels at all.

“There’s a good sissy, the shower is running for you, get yourself cleaned up and I’ll pick you out something to wear.” Emma said, still smiling.

“That’s okay, I still have my clothes from last night that I wore to the office, they should be fine.” I replied.

“Nonsense, Mike. You can’t turn up to work with me, in my car, wearing the same clothes as last night. What would people say?” Emma said with a wink. But I didn’t think that anyone would be able to guess exactly what had happened last night.

“Fine, I’ll go shower.” I said, knowing there was no point in arguing with her.

I took a shower in an en suite bathroom attached to the master bedroom, remembering to pat myself dry to preserve the tan, and of course the tan lines. After taking care of all my morning business in the bathroom, I headed back into the bedroom to find out what clothes Emma would be making me wear today.

I should’ve stayed in the bathroom.

“You cannot be serious!” I said, stunned by what I saw laid out on the bed for me.

The top was a white shirt, not entirely unlike what I had worn in the past, except for the sleeves which were short and puffy. The sleeves would only just cover my shoulders, leaving almost all my arms exposed with puffed up white shoulders. Plus the collar had a rounded cut as opposed to the more angular style of a normal mens shirt.

The shirt was feminine enough by itself, and that was without the black skirt!

It was clear that Emma wanted me to wear the skirt to work because she was already dressed and ready by the time I left the bathroom.

“Emma, I’m not wearing a skirt to work.” I said, a little more forcefully than usual, I was a little touchy already due to the lack of sleep and the pent up arousal.

“First of all it’s Miss Emma. And you will wear what I tell you to wear, or I’ll make sure you are punished! Punished by me and your Mistress. Is that clear, sissy?” Emma replied, her stern voice from last night returning.

I couldn’t really argue with her at this point, both her and the digital Mistress could upend my life easily at this point.

“Yes Miss Emma.” I mumbled in a defeated tone.

“And you can drop the attitude! Nobody likes a pouty sissy. So get dressed before I decide to lock you back into last night's heels.”

That was the end of that rebellion. Emma was ‘kind enough’ to loan me a clean pair of white satin panties and a matching bra to wear underneath the clothes. Thankfully, the bra was clearly bought with me in mind this time, the cups were flat against my chest. The bra cups did have quite a bit of padding in them though, so depending on how the shirt fit, it would appear I had small boobs hiding underneath the shirt.

I pulled on a pair of sheer, hold up stockings before putting on the skirt. The skirt itself was tight around my waist and hips, and ran all the way down to my calves, forcing my legs to stay close together. After zipping up the back of the skirt, I pulled on the shirt and fastened all the shiny silver buttons on the front.


There would be no arguments about my clothes being ‘a little androgynous’ today. I was dressed fully en femme … And I was supposed to go to work like this?

I made my way downstairs, taking small steps thanks to the skirt, to find Emma in the kitchen.

“Ah there she is. Those clothes look great on you! Come take a seat, I made you some breakfast.” Emma said as I entered.

I did as she said and took a seat for breakfast, which was a couple of pieces of avocado toast and some orange slices. I guess I knew how Emma kept herself in such good shape. I mumbled my thanks after eating the breakfast and waited for Emma to get herself ready for work.

“Here you go, sissy. These should do nicely for today.” Emma said, presenting me with a pair of shiny black enamel flat shoes. They were a slip on style that would leave all the tops of my feet bare except for the sheer stockings.

“Do I, er, have to wear these?” I asked, the shiny shoes would be the cherry on the cake of my humiliatingly feminine outfit.

“No, Mike. You don’t have to wear them. If you don’t want these then I can go and grab the heels from last night.” Emma replied with a smug grin, knowing she had me beat.

“No! That’s fine I’ll-I’ll wear these.” I said, taking the shoes from her and slipping them quickly onto my feet before she could change her mind.

“Good answer, the flats are much more practical for a day at the office.” Emma said with an amused smile.

A short while later, we were in her car and on the way to the office, both of us wearing shirts and skirts. I tried to bargain my way out of it one last time before we left the house, but was shut down by Emma threatening to make me take the train to the office dressed as I was.

We drove to work in silence, with Emma ‘accidentally’ stroking my thigh whenever she reached for the gear-stick.

Thankfully, the parking lot was empty when we got there, thanks to us being there so early. I walked as quickly as the skirt would allow from the car to the elevator, wanting to get to the relative safety of my workstation before anyone saw me in this outfit. Unfortunately Emma was in no such rush.

“What’s the hurry, sissy? We’re the first ones here. Or are you just so eager to get to work?” She asked me with a small chuckle as she sauntered slowly towards where I was waiting in the elevator.

We arrived on our floor shortly after, with me immediately sitting down at my station, thinking that if I hid my skirt underneath my desk then I wouldn’t feel so self conscious.

“Tony told me he has already forwarded all the files Jake was supposed to collate, I’ll send you half of them and we can get to work.”

I opened my work email and found the additional data I would be digging through for the day. I'm pretty sure Emma wanted to tease me more but we actually did have a lot of work to get through.

I forced myself to focus on work to keep my mind off my aching clitty. It seemed to work for a while and I was able to get through a chunk of work, that was until Emma interrupted me.

“Oh sissy.” She called out from her desk. “Why don’t you be a dear and go make us both a coffee?” It was definitely more of an order than a request.

“Yeah, good idea. I could do with one myself.” I replied, pushing myself out and standing up from my chair.

“There’s a good girl.” She added with a sly smile, her use of the feminine was very deliberate, and drew a twinge of arousal from my crotch.

I headed into the break area where the coffee machine was and started to make us both a drink. I was immediately reminded of my outfit when I stood back up from my desk, the skirt hugged tightly to my legs, forcing me to take smaller, steadier steps. The enamel shoes had solid bottoms and clicked loudly as I walked on the hard floor of the break area.

I dropped my own drink off at my desk and walked over to drop Emma's off.

“Why thank you, sissy. I'm starting to think I should've made you wear your maid's outfit to work instead.” Emma chuckled as my face flushed red….she wouldn't actually do that, would she?

I mumbled a nothing response and turned to head back to my own workspace, feeling Emma run a hand along my ass as I did.

“That skirt fits you so well, Mike. But the pantylines are very defined, I probably should have given you a thong to wear instead.” Emma said, causing my paranoia to skyrocket.

It took some effort to pull my focus back to my work after Emma’s teasing. My cock was desperate to get out of its cage by this point. This desperation wasn’t helped by Emma calling over to me at some point in the afternoon.

“Mike, could you come over here a sec please? I need your help with something.”

“Yeah sure, what’s up?” I said, heading over to her desk.

“My feet are a little sore, I think I wore the wrong shoes today. Do you think you could give them a rub for me?” Emma asked, dramatically batting her eyelashes at me.

“A-are you serious? You want me to rub your feet … at work?” I asked, incredulously.

“Of course I am, there’s no one else here, no one will see you. And besides, even if they did, you’re just helping out a coworker. Please Mike.” She asked again, clearly she wasn’t kidding.

“Yeah I guess I could, why not. Do you wanna turn your chair around here or …?” I asked, expecting her to swing out of the booth so that I could get at her feet.

“Oh no, I’m much too busy to actually stop working. You’ll have to get down here.” She replied with a devious smirk, pointing to the space underneath her desk.

“What?! You want me to get under your desk?” I asked, shocked at the obviously compromising position this would put me in if anyone actually saw.

But there was no one here to see, and I couldn’t really lie about not enjoying it at this point.

“Fine, whatever. Don’t say I don’t do anything for you!” I said as I stepped around her feet and slowly lowered myself to the floor, an act which was made difficult by the tight skirt I was wearing.

“Thanks, sissy. You’re a lifesaver.” Emma said as I awkwardly crawled backwards into the space beneath her workstation. I noticed that Emma had already kicked off her shoes, leaving her feet covered by just stockings. It wasn’t long before one of her almost bare feet was placed in my lap, right on my crotch area (I assumed this was deliberate), making sure my arousal was kept as high as possible.

I could hear Emma clicking away on her keyboard and mouse above my head as I worked on her feet. Occasionally she would let out an appreciative sound or two. At some point, Emma shuffled backwards in her chair a little. I saw one of her hands come into view and adjust her skirt, shuffling her hips around a little as she did. This motion had caused her skirt to ride much further up her legs, giving me a great view right up to her crotch from my subservient position.

The first thing I noticed, I guess Emma had decided not to wear underwear today! I couldn’t believe I was staring at her naked crotch, I was so stunned I had forgotten about the foot in my lap.

“Ahem. You’ve stopped massaging, sissy. Is something the matter?” Emma said, leaning her head backwards so she could stare down at me under her desk.

“What? Oh … Yeah, no I’m good, sorry.” I said, going back to work on her feet.

Why the hell was she naked under her skirt? It had to be deliberate, right? She did it just to tease me, that has to be it. Did she want me to look?

Does she only want me to look? Or does she want me to do something else? Was this some kind of test?

Needless to say, my cage was incredibly tight. I tried to focus on my task with Emma's feet, but the submissive position I was in kept turning me on more and more, making it impossible to focus completely. Plus, Emma kept shuffling around in her seat, occasionally squeezing her thighs together or shuffling her hips. Each time she did this, it would pull my eyes back to that spot between her legs. A spot that felt as though it was pulling my head closer.

I was snapped out of my horny stupor by a terrifying sound. The sound being the ‘ding’ of the elevator stopping on our floor. We had a visitor.

“Shit! Emma-” I started to speak but before I could finish, Emma had taken her own action.

She quickly pulled her foot away from my lap and planted both feet either side of me, before quickly wheeling her office chair further forwards, trapping me beneath her desk. I was forced to hunch over and slide all the way into the cavity, with her knees either side of my head, and my chin level with her seat cushion. I now had little choice but to stare straight at the current object of my desire.

“Tony! Hi. Thanks for coming down.” Emma said, greeting the visitor, who I now knew to be Tony from somewhere on the upper floors.

I held my breath as I heard his footsteps approaching Emma’s desk. I was well hidden by a solid back of the desk behind me, and a low partition wall that was at the side of Emma’s desk, but I knew if he got too close he would be able to see me.

“So, where's Mike? You're not trying to do everything alone are you?” Tony said.

“Oh no, Mike just stepped out to get some air. He started early with me, we've both had our hands full all morning.” Emma told Tony, subtly squeezing her legs tighter around me, making sure I was well hidden. My head was practically inside Emma's skirt now, and my face was about ten inches away from her naked sex.

God I wanted to lean forward and taste her, I could smell her arousal, causing memories of last night to come flooding back. I was so desperate to lick her that I somehow found myself slowly moving my head closer to her pussy. I was close enough that I could almost taste her.

“Anyway, I brought down those hard copies you asked for. We really appreciate you and Mike picking up the slack on this. Anything else you need, just let us know.” Tony said to Emma as I pushed my head closer to her. Just one taste…

“Thanks Tony, I appreciate it.” Emma said, as I heard Tony walking away.

It occurred to me then what Tony had said, Emma had asked him to bring something down here. She did this on purpose!

“That was a close one.” Emma said, leaning back to look down at my head sandwiched between her thighs.

“You told him to come down here! Are you trying to get us both fired?” I said, trying to push my way out from under her desk. I only managed to move her chair a couple of inches though, before Emma planted her feet firmly, stopping me from escaping her desk.

“Going somewhere, sissy?” She said, grinning down at me. “Because a few moments ago it seemed like you were searching for something. Why stop now that the coast is clear?”

“I don't know what you're talking about.” I lied.

“Oh really? Because it seemed to me like you were trying to sneak a taste of me. Or maybe it was the thought of Tony catching you down there. Should I call him back down? What do you think he would say if he saw my little sissy underneath my desk lapping at my kitty like a desperate puppy?”

“No! Don't call him back. Just let me get back to work.” I said, again trying to push her chair backwards. And again getting nowhere, I couldn't get any leverage from my cramped position.

“Don't worry about work for now, right now you should be worried about finishing what you started.” Emma said, shuffling forward in her chair to make it easier for me to access the spot between her legs.

There was no denying how much I wanted to do this, trapped under here or not, so without any further resistance, I gave in to my desire to taste her and dove in.

As I licked away at the mature pussy in front of me, I couldn’t help but think how my last few most recent sexual encounters had involved me pleasuring a girl with my mouth, while being left desperately horny myself. It seemed I was on track to becoming a tool others could use for their own pleasure. The worst part though, was just how much these thoughts turned me on. Is that really what I wanted? Would I become accustomed to being caged and denied while others used me to get off? Was this what I was hoping for when I downloaded that damn program?

All these questions and more flooded my horny mind as I lapped away, hearing Emma moaning above me and the occasional twitch of her hips.

“Ohhh, Mike. Such a good girl! Did you ever think ‘ahh’ that you would be here, under my desk at work? Mmm between my legs, wearing skirts and panties to get me off while you remain locked away with no relief. Is this all you ever fantasized about, sissy?” I couldn’t exactly answer Emma from my position, so I just kept on licking her towards orgasm.

“Ahhh, yes! That’s it, lick me you desperate sissy slut!” Emma was clearly getting lost in the moment as she verbally tormented me before cumming hard onto my waiting mouth.

I kept on licking and sucking her as she came all over the lower half of my face, savouring every last taste of her juices until she wheeled her chair backwards, removing herself from my eager lips and finally giving me enough room to get back to my feet.


“That was wonderful, sissy. Just what a girl needs to blow off steam in the middle of a busy shift. It’s just a shame you’re all locked away with no relief of your own. But then again, I’m starting to think you prefer it that way.” Emma said, straightening out her skirt as I climbed out from under her desk.

“I do not prefer it like that! I’m not sure if I’ve ever been more desperate to cum than I am right now.” I wasn’t lying as I spoke, my poor clitty was pushing hard against the side of its cage, desperate to be touched.

“Well that may be true, Mike. But I think deep down you know…” Emma leaned back in her chair, staring me straight in the eyes as she spoke. “...Sissies should be caged.”

My clitty belongs in a cage.

The thought seemed to appear from the back of my mind as Emma spoke. I was starting to think that all the overexposure to the sissy lifestyle was beginning to show some side effects.

I walked away from the encounter with Emma speechless. Emma grinning to herself in a satisfied manner, knowing that her words had had some sort of effect on me. My clit was- No, my cock was throbbing in its cage. I was back to being desperate for relief, knowing that I would be begging the digital Mistress to unlock the cage as soon as I got home from work.

I headed into the bathroom to wash my face, I couldn’t think straight with the taste and smell of Emma's juices still all over me. I waited in the bathroom, splashing cold water on my face until my arousal died down enough for me to get back to work.

I diligently worked away for the rest of the day, the extra workload doing a good job of keeping me and, more importantly, Emma occupied until finishing time.

I was glad to be shutting my computer down for the day, the extra workload combined with my extreme levels of arousal after being trapped under Emma’s desk had left me a wreck. I only hoped Mistress would be kind to me when I got home, after all, it was my decision to lock the cage back on, so surely it would be my decision to take it off.

“Well Mike, it’s been fun. Can’t wait for our next sleepover.” Emma said as she prepared to leave herself.

Shit, my clothes!

“Umm, Emma, can you give me a ride home? I really don’t wanna have to get a bus or walk like this.” I said, gesturing down to my outfit.

“Oh I don’t know, Mike. Your apartment is a little out of the way for me, and I’ve had such a long day at work.”

“Please Miss Emma,” I asked, thinking the use of ‘Miss’ might convince her to take pity on me, “I really don’t want to go out in public in a skirt. It’s just too much. Could you please just give me a ride home?”

“Okay fine. I’ll give you a ride, but just this once. And you owe me one.” Emma replied.

“Yes. Anything you want, just name it and I’ll make it up to you I swear.” I said, very grateful for the lift.

“Anything huh? I’ll remember you said that, sissy. Come on then.” She said, turning quickly and heading for the elevator.


“You can keep the outfit, by the way.” Emma said as we pulled into the parking lot of my building. “Just be careful of the pantylines next time you wear the skirt to work.”

“Gee, thanks. But I’m not so sure wearing skirts to work is going to be a regular thing.” I replied, a little sarcastically.

“Oh we’ll see. By the way don’t forget your bag, I left it in the trunk for you with your new heels so you can practice walking in them at home.” Emma said.

“Oh right, can’t forget about them.”

“Well, bye for now, sissy. I would ask if you had fun last night and today but we both know the answer to that question don’t we?” She said with a flirtatious smile.

“Yeah I uh, guess I can’t really deny it to you now can I?” I replied.

“Definitely not. Now go on, grab the bag and get home. I’m sure your Mistress will be missing you by now.” Emma said reaching across to open my door for me, which only served to make me feel even more like a submissive girl for her. She gave me a teasingly slow kiss on the laps as she leaned back, causing my breath to catch in my throat and cock to pulse in the cage.


I gathered up the bag from the trunk and headed up to my apartment, praying I would not be seen by anyone. My head was spinning as I walked down the hallway, so confused by arousal that I totally forgot about the electronic locks on the door again, at least I did until Mistress sent me a message.

“Welcome home, sissy. Please provide evidence of the correct underwear to gain access to your apartment.”

Of course, I briefly considered just reaching down and pulling the tight skirt up my legs to expose the panties, but there was something so hyper feminine about lifting up my skirt that I decided to just undo the zip and shimmy the skirt down below the panties.

After undoing enough buttons on the shirt to expose my bra, I stepped backwards and waited for the click to signal the door being unlocked.

“Welcome home, sissy. Miss Emma has kept me updated on your progress overnight, and has advised me that you need more training on how to properly walk in heels. I have placed an order for some items that will help with this.” The AI voice told me as I deposited the bag from Emma's and the box containing the lockable heels.

“Ugh, great. Can't Wait for that.” I muttered to myself, hoping I was quiet enough that Mistress would not hear me

“Mistress,” I geared up to ask the question that had been burning since I woke up this morning. “Do you think you could unlock my chastity cage? I erm, I need to masturbate.” I asked, remembering how I was supposed to ask last time.

“Unfortunately, as you have not received any instructions from me in the last 24 hours, I am unable to confirm whether or not you have earned any time out of your cage. Therefore, I will have to check in with Miss Emma for confirmation….message sent. Awaiting response.”

Ah fuck. Before I even had a chance to protest, the message had already been sent and Emma would soon be given the power to decide whether or not I could get myself off today.

I busied myself for a few minutes, tidying up a little around my apartment while waiting to hear from Emma. What would she think? About 10 minutes after dropping me off I was asking her if I was allowed to be unlocked so I could jerk off. I snapped to attention at the sound of my phone ringing, one look at the screen told me it was Emma calling.

“He-hello.” I answered, nervously.

“Hello sissy. I just received an interesting message from your Mistress. I haven't even gotten out of my car after dropping you at home and you're already trying to escape from your cage, hahaha.”

“Yeah I'm, I'm sorry. I'm just incredibly horny after the last couple of days with you.” I said.

“Oh you poor thing. And now you need my approval just to be able to play with yourself. I have to say having this kind of power over you is quite the turn on for me. So tell me, Mike, what will you do for me in return?”

Dammit. Like I haven't done enough for her already?

“Right now, I guess I'd do whatever you want.” I replied, honestly.

“Mmmm, that's what I like to hear. I'll tell you what, Jake is out of the office for the rest of the week. Wear the skirt to work again tomorrow and I'll let you out of your cage.”

“Emma, isn't there something else I can do? I don't want to have to travel to work by myself in a skirt.”

“Ah but it will be good for you, it's about time you started fully embracing your sissyhood. Those are the terms Mike. How badly do you need to cum right now? How badly do you want to get out of that cage and diddle your little sissy clitty?”

“Emma, please I-”

“I'll bet your aching so bad aren't you. Will you think of me when you do it? Will imagine yourself between my legs once again. Licking my sweet pussy.”

Emma knew exactly what she was doing. Driving me arousal back to its peak with her talk.

“Maybe you'll imagine yourself back in your maids outfit. Frilly white panties and stockings, kneeling at my feet, begging for a taste of me. You can have your release, sissy. All you have to do is say yes. Skirt on, cage off. It's an easy decision really.”

I couldn't help it, Emma was driving me mad with lust as she spoke there was no way I was going to say no by this point.

“...Yes. I'll do it just, please let me cum.” I begged, one hand already rubbing against the cage, almost of its own volition.

“Good answer, sissy boy. I'll send a message to your Mistress with our deal. Have fun.” ‘Click’

Emma ended the call before I had a chance to rethink the deal.

A few minutes later, Mistress’ voice came through the smart speaker.

“Congratulations sissy. Miss Emma has given you permission to be unlocked for the evening. I trust you are aware of her condition?”

“Yes Mistress.”

“Excellent. Assume your position in front of your laptop and I will find you some suitable material to masturbate to.”

Of course she would still want to choose what I jerked off to. But I didn't care at this point. I'd watch all the sissy POV or sissy hypnosis videos she wanted as long as I could get the cage off.

Is this what I had been reduced to in just a matter of weeks? Trading my dignity and masculinity just for an opportunity to rub one out. I guess I already knew the answer to that.

Surely it couldn't get worse than this … right?

End chapter 6