Digital Dominatrix 2.0 chapter 7 (Patreon)

Digital Dominatrix 2.0 Chapter 7


I slept a lot better last night than I had done in the last couple of days. Mostly due to me being able to take the cage off for a while before going to sleep. Of course, Mistress had made sure I was forced to watch an entire 35-minute video filled with sissy imagery and sounds. And there was the fact that in order to obtain permission to take the cage off I had agreed to wear a skirt to work the following day. But still … I was too horny to pass up the opportunity.

I woke up on Wednesday morning feeling pretty good, at least I did until I remembered about the skirt. I already knew there was no way Mistress would let me leave without making sure I was wearing the skirt first, and thanks to the electronic locks on my apartment door, I couldn’t really defy her.

I showered off and checked myself out in the mirror. My face flushed a little as I looked at the tan lines in the shape of a bra and thong, still clearly visible thanks to the fake tan I was still covered in. I also noticed a little stubble forming on my legs and chest. Would I need to remove the hair again, or would I be allowed to let it grow back out?

As I entered my bedroom, Mistress AI voice came from the smart speaker next to my bed.

“Good morning sissy. Don’t forget you must be wearing the skirt before leaving for work today. You must also make sure you have on some stockings and panties, along with your bra.”

“Yeah yeah I know.” I replied. It wasn’t like I needed reminding of the humiliating terms of the agreement. I had already spent a day at work in the skirt, but that was with Emma driving me there and back, so I was far less exposed than I would be today, travelling alone from my own apartment.

I grabbed some stockings and the same bra I had worn yesterday, I made sure to pick out a clean pair of panties. I decided on one of the thongs I first bought almost two weeks ago, remembering what Emma had said about the obvious pantylines yesterday.

I didn’t bother with the shoes this time, though, instead of deciding on a pair of my own pumps. These would be the only male items of clothing I was wearing after I had put on a cream coloured shirt with visibly feminine edging.

Just as I was ready to leave for work, Mistress spoke again.

“Make sure you come straight home from work today, Sissy. You have a large delivery that I have scheduled to arrive shortly after your shift finishes.”

Oh shit, I had forgotten about her making another purchase on my behalf. Don’t give an AI Dominatrix full access to your bank accounts, people.

“Okay Mistress, I’ll be home on time.” Not as if I was going to be dawdling about dressed like this anyway.

After taking a deep breath to prepare myself, I headed out to work, skirts and all.


I usually walked to work, only living a couple of blocks away, but today I decided to catch a bus, figuring I could tuck myself away in a corner seat, which would mean less people would notice the skirt.

I walked to the nearest bus stop, the tightness of the skirt forcing me to walk slower than I usually did. I was feeling incredibly paranoid that everyone would be staring at me. I did notice myself getting a few sideways glances as I waited at the bus stop. Even with the feminine outfit, it was still a little too obvious that I was a guy in womens clothing.

The bus arrived and I stepped inside, thankfully I was alone at this stop, and there weren’t many people on the bus. The driver barely looked at me as I paid for my ticket and headed to sit down, so far so good. I spotted an empty seat close to the back of the bus and sat down next to the window. Breathing a sigh of relief, I was much better hidden now that I was sitting in the cramped seat of the bus.

I stared out of the window as the bus made its way towards its next stop. After a few minutes, the bus pulled up at its next stop. I watched nervously, as a lot of people got on at this stop, occupying most of the seats.

Thankfully, there was enough room so that no one had to take the seat right next to me.

Unfortunately, my luck wouldn’t last. As the bus pulled up to its next stop, I saw from the window that there was a huge queue of people waiting to get on. I watched with bated breath as all the seats gradually filled up around me, until the space next to me was the only seat left.

My heart rate started picking up as I watched a girl who looked to be in her early twenties walk slowly towards me. I knew that if she could see the skirt from her position she would have probably chosen the standing room. Instead she walked straight to the only empty seat on the bus and sat down right next to me.

“Hi.” She said politely as she sat down in the seat next to me. I just smiled in reply, hoping to keep as low a profile as I could and not engage her in any sort of polite small talk.

As the bus rumbled along its path, I took some solace in the fact that my stop was next up. The only problem with that was that I would have to stand and walk past the now full seats to get off. Clearly I did not think this plan through.

As I travelled to my stop, I could see that the girl sitting next to me kept taking glances at my legs and … fuck! My damn nails were still a bright pink colour. With everything else that had happened I had almost completely forgotten about them. I balled my hands into fists to hide the nails from the girl's gaze, but that just made things worse because as soon as I did, I heard her stifle a small chuckle. I chanced a look at her face and could see she was staring at me intently with an amused look on her face.

“Love your nails.” She said as we accidentally made eye contact with each other.

“Oh er, yeah. Thanks.” I replied, turning away to stare back out the window.

“They go great with that skirt.” She added, the hint of a laugh trying to creep into her voice.

Great, now random strangers on the bus were making fun of me.

“Thanks! My stops coming up, gotta go.” I said, quickly standing up and squeezing my skirted ass past the girl to escape into the aisle.

I wanted to make as quick an exit as I could so I made sure I was right at the front of the bus before it pulled up near my work.

As soon as I exited the bus I walked as quickly as the skirt allowed towards the safety of my office building.


“Good morning sissy-boy.” Emma said brightly as I entered the bullpen-like area where we worked. “I see you’re wearing your skirt again.”

“Like I had a choice!” I snapped, a little out of breath from the rapid walk into work.

“Oh but you did have a choice, sissy. All you had to do was not take off your cage and jerk your little cock last night and you could have worn your normal work pants. But you just couldn’t help yourself could you?” Emma replied, knowing she had me beat. She was right, after all, I had accepted the deal because I was so desperately horny last night.

“Whatever. We both have a lot of work to do, so get a good look will you? Here I am, in a skirt, as promised. Happy?” I said, a little petulantly.

“Thrilled actually. It’s so satisfying for me to see a sissy finally start to accept who they are.” Is that really all I was to her now? Just a sissy?

As I walked past Emma towards my own desk, I noticed for the first time that her wardrobe was a little different today. She looked mostly professional, but there was something a little different. The black skirt she was wearing was a lot shorter than usual, stopping high up on her thighs and doing a good job of accentuating her wide hips and voluptuous ass. Her white shirt was not buttoned all the way up, exposing more cleavage than she usually did at the office.

“Are you checking me out again, sissy?” Emma said playfully, catching me staring.

“Oh! I guess I was, you look a little … different today. You look good.” Was all I could think to say.

“Well thank you, Mike. I guess I am dressed a little less … conservative today. But don’t let me distract you from your work now.”

I sat down and got to work as Emma did the same, all of her movements seemed deliberately slower and more seductive. I watched her bend over at the waist to adjust her chair before she sat down, the short skirt of hers riding dangerously high on the backs of her thighs.

Her teasing attitude didn’t let up at all for the rest of the day. Thankfully, we were both kept pretty busy by the workload we had, so she didn’t have a chance to ask too much of me, no under the desk foot rubbing or pussy licking today. I didn’t know if I was sad about that or not.

She of course made sure to comment on my lack of pantylines today, questioning me about my choice of underwear, even going as far as to call me a slut for wearing a thong. Needless to say, I was once again very tight in my cage by the time the work day ended. I wasn’t going to give in and ask to be released again so soon after being allowed out though, especially after the deal I had to make last night.

I decided against the bus for the way home, deciding instead to just walk the couple of blocks back home. I kept my head down low the whole way, practically staring at my feet as I walked. As I glanced around occasionally, I spotted one or two people staring my way as I walked, obviously confused as to why this dude was walking around in a skirt, but none of them said anything.

I hopped in the elevator as soon as I got to my building and rode it to my floor, anxious to get to the safety of my own apartment. Unfortunately, I wasn't that lucky. As I exited the elevator on my floor I saw a delivery guy outside my apartment with a cart and a huge brown box.

Dammit.

“Uh hey um, dude? Are you a Mike by any chance?” The delivery guy said as I walked up to my door.

“Yeah that's me.” I said, taking out some ID to prove who I was.

“Great, then these are for you. Sign here.” He said with a confused expression, clearly looking at the skirt. I was mortified!

I signed on a tablet the guy held without making eye contact. He leant the large package up against the door with a smaller one on top of it, wheeled his cart away and headed for the elevator. As I watched him wait for the elevator doors to open up, my phone vibrated with a message from Mistress. A reminder that she needed to check my underwear just so she would let me in. I couldn't exactly do that with the delivery guy still on the floor so I made a show of checking out the large package, was this some kind of furniture?

The box was almost as tall as I was, and what was in the smaller one on top? And why the hell was the elevator taking so long?

Finally, after what felt like forever, I heard the ‘ding’ of the elevator and watched as the delivery man stepped inside.

As soon as the door was closed I pulled open my top and lowered the skirt, displaying my feminine underthings to the camera so Mistress would let me inside. Once the door was opened, I half carried, half dragged the large parcel inside my apartment and closed the door.

“Welcome home sissy. I see your latest delivery has arrived. You should have received two parcels, one large, requiring a signature, and one small. Please unbox and prepare the contents of the larger parcel as soon as possible. I will give you two hours to complete this task.”

Great, barely through the and already being ordered around. At least I had two hours to prepare the larger parcel, so I spent the first half hour or so changing into a pair of baggy sweatpants and a loose T-Shirt, taking off the bra in the process. After grabbing a drink and using the bathroom, I got to work on the bigger package.

I laid the large delivery down in the living area and sliced open the cardboard, once that was out of the way I took a look at the contents. I have to say, I was a little surprised at what I saw inside.

It was a treadmill. A pretty high end one too by the looks of it, of course it came with a link to download a partner app for my phone. According to the instructions, the partner app could be used to track my progress, as well as for me to download some preset training routines. But I had a feeling Mistress would have her own ideas for the app.

The treadmill itself was in two parts, the part that I was supposed to walk on was the heaviest, with a tough black belt that had a white line printed down the center. The other half was the stand up section that would attach to the main belt and be positioned in front of me, with two curved handles that I could hold on to.

It was surprisingly easy to get the thing assembled, I decided the best place for it would be my bedroom, it would look a little out of place in the middle of the living room or kitchen.

All I had to do when everything was connected was plug in the device and wait for a small LCD screen to boot up. Once the company logo had disappeared from the screen, I was shown a prompt to download the app onto my smartphone. Before I could even unlock my phone, Mistress spoke up.

“Well done, sissy. I can see your new treadmill is all set up and ready to go. I have already installed the partner app onto your phone and pairing will be completed soon. In the meantime, you should have come home from Miss Emmas with a gift. A pair of high heeled shoes fitted with locking straps. While I prepare the treadmill for use, you are to make sure the shoes are locked safely to your feet.”

I guess now I knew what the treadmill was for. It looked like I was going to be getting some more practice in the heels. I grabbed the shoes and squeezed my feet into them. I was a little more confident than the first time I had worn them, but was by no means comfortable in them yet. That was about to change.

Emma had been ‘kind enough’ to leave the small padlocks in the box with the shoes, so by the time I had both shoes locked in place, I was left standing there holding two small silver keys in my hand.

“Good job sissy. Now that you are wearing the shoes, you may open the smaller package.”

Oh right, almost forgot about that one. I tore open the smaller of the parcels to reveal some kind of electronic key safe. It was a small, square thing made of a pretty tough, thick metal. And of course, it was bluetooth enabled. It could be unlocked with my smartphone, or set to a timer. I pulled a small plastic tab out of the battery panel and a thin display screen popped up. I didn’t even bother to read the instructions, I was pretty sure I knew what was coming by this point.

“Excellent sissy. Please place the keys for your shoes into the lock-box you have just opened.”

I did as I was asked by the AI, knowing she had enough dirt on me not to argue back.

As soon as the keys were inside the lock-box, the small display changed to simply say ‘locked by user’. Looks like I was once again trapped in the heels. I guessed it was time for me to test out my new treadmill. I was a little worried to look up how much this thing cost. I had seen the commercials and I’m pretty sure they were close to a thousand bucks!

I placed the lock-box on my bed and stepped carefully onto the treadmill.

“Excellent, sissy. We are now going to teach you how to walk in high heels. I will start off slowly, and monitor your progress using both the app, and the camera in your room. Let’s begin.”

With that said, the treadmill kicked into life, at least it started at a slow pace. I grabbed on to the two protruding handles in front of me, steadying myself as I began to take careful steps along the moving belt.

I carried on at this relaxed pace for a few minutes, starting to feel like I was getting comfortable. That was until Mistress spoke up again.

“You are doing well, sissy. But from now on, you are not permitted to use the supports. Please let go of the handles immediately.”

Okay, now this was turning into a real test. I did as I was told and released the handles … I was now walking unassisted.

Miss Emma's words rang in my head as I walked carefully on the machine. Heel toe, heel toe.

I was a little unsteady at first, but quickly adjusted my gait until I got back into a comfortable swing. I carried on for a while longer, starting to feel pretty good. That was until the treadmill increased its speed.

“Woah, shit.” I stumbled a little at the sudden speed change and instinctively reached out to grab the handles to steady myself.

“Release the handles, sissy.” Mistress spoke up almost as soon as my hands touched the handles.

I let go and carried on walking at the new increased pace. I figured about half an hour had passed and I was doing okay. I was half expecting the speed to increase, but once again, Mistress surprised me.

“You are doing well sissy. But now I need you to watch the video playing on your laptop, and try to mimic the girl on the screen.”

Sure enough, I turned my head to the side where my laptop had been woken up and was now playing a video of a woman walking along. It appeared to be some kind of close up chase cam, the camera was positioned close behind a woman who was simply walking down the street, her legs and ass encased by a tight fitting pair of yoga pants. She had an incredibly seductive wiggle in her hips as she walked. The wide hips on the screen were swinging side to side as she walked. The whole video was only about 30 seconds long, but was playing on a continuous loop.

“Make sure to swing your hips as you walk sissy. Focus on allowing your hips to drop down a little after each step. This will give you a nice, sexy strut.”

A nice sexy strut, just what I needed to further my humiliation.

I kept my head turned a little so I could see the video playing on the screen and tried to focus on imitating her as best I could. This went on for a while, Mistress would occasionally chime in her own brand of ‘helpful hints’. After about fifteen minutes of ‘strutting’ on the treadmill, my feet were starting to ache again. Thankfully, I felt the treadmill begin to slow down to a stop, giving me the opportunity to step down and give my feet a little relief from the constant walking.

“Well done, sissy. You have completed the first part of your heel training. You should rest your feet for a few minutes before the second part begins.”

Second part?! Did she mean I wasn’t even finished yet?” After all that I guessed I wasn’t done with the treadmill yet.

I sat down on my bed for a few minutes, leaning down to rub my calves, relieving a little pressure.

After a few minutes, I stood back up and headed back towards the treadmill, only to be interrupted by Mistress.

“It is time to continue your training, sissy. Please listen carefully to my instructions.” Well this wasn’t what I expected, would it not just be a matter of getting back on the treadmill?

“In order to release the keys to your heels from the lock-box, you will be required to take your phone and walk a distance of one point five miles away from your apartment. You may travel in any direction as long as you reach the required distance. I will be using the GPS on your phone to track your progress and I will notify you when you have travelled a sufficient distance. There is no time limit on this task, but the lock-box will not release the keys until it is completed. Do you understand?”

Shit, so now I was going to have to go out and walk around in public in a pair of high heels!

“Mistress, can’t I just finish my training on the treadmill?” I asked, hopefully.

“I am afraid not, sissy. The keys will not be released until you have travelled the required distance.”

Dammit. I guess I was going for a walk. I checked myself over before I left, trying to find some way to hide the heels from view, but no matter what I tried, it was all too obvious that I was wearing high heels. I made sure the baggy pants were low enough that they covered the little padlocks near my ankles, at least that was a small victory.


After psyching myself up, I stepped out of my apartment and headed out. The sound of my heels echoing across the wood floor was ringing extra loud in my ears, like a signal for anyone within earshot to look in my direction.

Thankfully I made it out of the building without running into anyone. Another small victory.

I decided to pick a direction and just start walking. I opened up the GPS app on my phone to keep track of my progress. 1.5 miles wasn’t super far walk normally, but I was definitely not as fast in the heels, but I did feel a lot more confident after all the treadmill work. I shut out all the noise of traffic and ignored all the people I passed on the street and just focused on my walk. I noticed after about five minutes of walking that I still had a touch of that feminine sway in my hips. I actually had to concentrate a little to make sure I was walking normally.

The heels kept clicking their way down the sidewalk as I kept my eye on my phone's map. I was almost at the required distance after a while and feeling very comfortable in the heels. Although my feet were still aching quite a lot.

One minute and a few more funny sideways glances later, I received a notification from Mistress.

‘Well done, sissy. You have travelled the required amount, the lock-box has now been opened and you are free to remove the heels upon your return home.’

Great, mission accomplished, I thought as I turned around and headed back home. The walk back felt a lot shorter than the walk out, probably because the nerves had worn off. It’s funny really how little people pay attention to strangers. I mean, imagine if you saw a guy walking down your street in a pair of heels, how would you react? You probably wouldn’t say anything to him really. Maybe you’d point him out quietly to a friend or mutter something under your breath, but really, you would probably have forgotten him the second he left your line of sight.

It was these musings that led me home in confidence, before I knew it, I was back outside my door, waiting for the message from Mistress.

‘Welcome home, sissy. Please provide proof that you are wearing the correct underwear to gain access to your apartment.’

Shit! I had taken off the bra earlier and never put it back on. I quickly typed up a reply.

‘I am sorry Mistress, I do not have a bra on right now. I forgot it earlier. Please let me in.’

Her reply came quickly.

‘You know your new rules, sissy. You are to make sure you are wearing your bra and panties everytime you leave the apartment. You have failed to follow my rules, and must be punished.’

Dammit, what was she going to do now?

‘I have compiled a small selection of images taken from your home security cameras. As this is your first infraction of this nature I will allow you to select one contact for them to be sent to.’

This again. ‘Okay, I choose Emma.’ I replied.

‘I am afraid you selected Miss Ema last time, sissy. You have to select someone different this time.’ Fuck.

‘Okay then, I guess it will have to be Kate.’ I was still trying to ease Kate into this kinky shit, so having her see a selection of photos of me that were no doubt extremely humiliating, was not something I was thrilled about. Hopefully she took it well.

‘Good choice, sissy. The file has been sent to Kate, you may now enter your apartment.’

Finally, I could get back inside and take off the heels. A short while later, I was sitting on the edge of my bed, rubbing my sore feet after removing the heels. While I was tending to my aching feet, I felt my phone vibrate from somewhere next to me … It was a message from Kate.

‘Ooooh this was a surprise. Looking good panty boy. I especially like the maid outfit. Maybe I could book your services Friday? My apartment could use a good clean, and who knows, I might even make it worth your while ;) xx’.

Well, at least she didn’t call me a pervert or a weirdo. I wondered if she was serious about ‘booking my services’. Just as I was considering what my reply could be, an outgoing message popped up in the chat window … Mistress had replied for me before I had the chance to even start typing. I was mortified at the response that Kate would now be reading.

‘I would love to be your sexy, sissy maid for the night. I’ll see you on Friday xx.’

Dammit, the AI had even mimicked the ‘x’ at the end of the message, this really was a smart program.

‘Sissy maid…haha that is so cute. I can’t wait. See you Friday xx.’

Well, I guess that was my Friday night planned for me.


As I got into bed, I couldn’t help but wonder about what I was becoming. By the time Friday night came, I would have served as a maid for two different women and three separate occasions. A fantasy I had never thought would possibly come true, but here I was. Just how far was I going to let this program go?

I drifted off to sleep with my locked up clitty throbbing in its cage as I thought all about my journey so far. Once again, I could have sworn I heard a small voice start speaking as I drifted somewhere between awake and asleep.

“You are a sissy…..”