Digital Dominatrix 2.0 chapter 1 (Patreon)

Digital Dominatrix 2.0 - Chapter 1



Thursday morning, I woke up to the feeling of my morning wood, something I wasn't used to, having spent so much of the last 2 weeks in chastity. Memories of the night before still fresh in my head, but still unbelievable. I had actually spent the evening playing the role of a maid for my coworker. It was a fantasy I'd had for a long time, and somehow, thanks to Mistress, it had actually happened.

The problem was, what happens now? How would I face Emma at work after last night? She had seen me in a way that no one else had ... in a state I hoped no one else ever would. Not only that, I had been spanked over her knee! I was going to be reliving that moment every time I saw her. Just thinking about it now had me reaching beneath my bed covers to grab at my erect cock. Fuck it ... I had time.

With another quick session of self pleasure out of the way, I got up and got showered off, ready to face the day at work.

I grabbed the bag I had taken to Emma's house last night and noticed the small padlock was still in place on the zipper. She had done this to ensure I had to run through my apartment building in the maids outfit. As promised, breaking the tiny luggage lock off was easy enough with a screwdriver. The problem came when I unzipped the bag and looked at the contents.

I was expecting to find the clothes I had worn to work yesterday, but it seemed Emma had had one last bit of fun with me before we left her home. The trousers and shirt combo had been replaced with a similar looking female version. Black women's pants and a white blouse. The items were close in appearance to what I usually wore to work, but at close inspection you could tell they were designed for women.

The trousers had a front zip and button fastening, and looked narrower around the waist. I could tell they would have to sit higher up on my hips to be able to get them to fasten properly.

The top could pass a white office shirt except it buttoned the wrong way and would fit much looser than I was used to, with stitching that gave it a slight feminine touch. Did Emma really expect me to wear this?

I got my answer when I headed into the living room to search for a pair of replacement trousers.

"Good morning slave," Mistress' voice came through the speaker shortly after I entered the living room. Clearly the motion sensors she had me install are still working fine.

"Miss Emma has informed me that she has kindly loaned you a new uniform for work. You must make sure to wear your uniform today. Along with your stockings, panties, and your bra."

Fuck no! That was my first thought. I already had feminine eyebrows and pink nails thanks to Mistress' work. If I went out in that uniform I would be fully femmed for work, which wasn't what I had planned.

"Mistress, I don't think I can wear those clothes to work. People will notice something going on." I said, hoping for a little mercy. Unfortunately, mercy wasn't something the Mistress program was capable of.

"You will wear them slave, otherwise you will be punished. As you are not currently in chastity, your punishment will come in a different form. Failure to follow my orders will result in me sending out a selection of photos from my archive, to as many of your contacts as an RNG program selects. This could be up to fifty randomly selected people from your email or phone book contacts. You are to present yourself for inspection before you leave for work."

Dammit. I quickly did a mental recollection of the photos that Mistress had. Counting the footage from the security cameras, I would be screwed if they were sent out. At least I wasn't in chastity for once, but with her new approach to punishments, I wasn't sure that was a good thing.

I had learned by now that there was no point in arguing with Mistress. She was an AI, designed to follow her programming. She would carry out her punishment without guilt or remorse, it wasn't malice that drove her, it was lines of code. It was with this in mind that I went to get changed into the feminine clothes. I decided on the thong to wear, mostly because I figured the female pants would easily show any pantylines, far worse than my male ones would.

The pants were far too snug around my ass and crotch area, partly because they sat so high up on my waist. The way we're designed, the waistband was pinching my sides in a little, giving me a very feminine appearance on my lower half, helped by the fact that the legs underneath were still completely hairless.

The top went on over the bra, sitting loosely on my upper half. The material was flimsy and floaty around my top, which felt a little alien to me. The hem of the shirt was shorter than usual, and I could feel it riding up on my masculine frame. I realized then that the shirt was designed to be tucked into the pants, I had seen Emma wearing a similar outfit a number of times. I knew right away that tucking the shirt into the pants would give further my feminization, but without doing so, the shirt just wouldn't fit right.

I headed back into the living room where the Mistress main speaker was located and stood in front of the camera for inspection. After receiving Mistress approval, I was headed off to work, incredibly apprehensive about what people would think if they saw me like this. I had a jacket on my top half which made me look less feminine as I walked the couple of blocks to the office building.

During the walk, I immediately noticed that the thong might not have been the best idea, without the chastity cage to hold everything together, the front panel of the thong just wasn't designed to hold my package. I constantly had to readjust myself as I walked, and the seam at the back of the trousers seemed hell bent on riding up between my cheeks.

I exited the elevator at work onto my floor and headed into the office. I had hoped to be the first one here so as not to draw attention to myself as I walked in. No such luck.

I had beaten Jake in, but as usual, Emma was the first one in. I could feel my face flush red and my cock start to stiffen as the memories of yesterday came rushing back to me as soon as I saw her.

"Hi." Was all I managed to say as I headed to my desk.

"Oh hello Mike. How's my little sissy this morning." She asked with a coy smirk.

"Could you be a little more discreet? We are at work, you know. I thought you were the professional one." I said, moving towards my desk to set up for the day.

"Well it's hard to remain professional with someone who spent the afternoon cleaning your house in a sexy maids outfit. Besides, Jakes not even here yet." Emma's words not helping my underwear situation at all, my cock was now fully erect and completely free of the thong.

"Oh, and speaking of 'outfits'," I continued, "what the hell is this?" I asked as I pulled off my jacket, revealing my new feminine office look.

"Oh good you found my gift! I was hoping you would wear them." Emma said as she eyed me up and down.

"Yeah well, I didn't have much of a choice did I? Thanks to you!"

"Me? All I did was let your Mistress know that I left you a little gift. You didn't have to put them on." Emma replied.

"Yeah, tell that to Mistress. She forced me to wear the whole outfit." I said, annoyance creeping into my voice.

"How did she force you? I can already tell you're not locked in chastity right now hehe." She struggled to suppress a giggle at her latest comment, very clearly staring at my crotch.

"Oh fuck!" I said, reaching down to adjust myself as I noticed the obvious tent in the slacks.

"Haha see, you're clearly still enjoying yourself."

I am NOT enjoying this!" I said, defiantly. "And she didn't need the cage. She told me she would just email a bunch of people in my contacts if I didn't do as she asked. I'd much rather her simply extend my time in the cage. It's weird but like, it seems she's stepped up her punishments and demands overnight."

"Really? How do you mean?" Emma asked, leaning in closer to my desk.

"Well, before it would be an extra day in chastity, if I disobeyed then it could be like, one photo sent to one person. But this morning, she seemed to dial it straight up to eleven with no warning. She could have actually sent a whole catalogue of images to fifty people if I didn't wear these stupid clothes to work today." I explained.

"Hmmm, that does seem a little drastic. You'd better just do as she says for now. Luckily for you, you have me to help you get through this." She said with a smile.

"Yeah, and to humiliate me by proxy." I said, sullenly.

"Oh please. I can still see your little cock trying to break out of your pants." I wished she was wrong.

We both settled at our desks shortly after, as Jake had arrived, at least Emma was still being a little discreet. Apart from Jake's eyes lingering on me a little longer than usual when I greeted him, nothing else happened for the rest of the morning. I guess Mistress didn't need any photographic evidence, given that my outfit was on display before I left the house.

The problem was Emma. Everytime she got the opportunity to come near me, she would do or say something suggestive or teasing. It was like she made it her personal mission to keep my erection visible all day. I was almost more desperate now than when I was in the cage. At least the cage eventually started to chafe a little which killed the erection. But now, with my cock free and the thong doing nothing to contain it, every little shift of fabric was turning me on.

I was in the breakout room, making myself a drink when I felt a soft 'smack' on my butt.

"Hello Emma." I said without turning around.

"How did you know it was me?" She said, hopping up to sit on the counter beside where I was standing.

"Because Jake wouldn't be unprofessional enough to slap my ass in the office."

"I should hope not. But maybe he wants to, could have sworn I saw him checking you out earlier." Emma said, chuckling.

"Very funny! Did you need something or did you realize you haven't tormented me in almost half an hour?" I said.

"Oh don't be a pouty sissy! I just couldn't resist copping a feel, you look so good in your new outfit. Anyway, you weren't complaining about my professionalism last night while you were over my knee getting a spanking." She said in a low, suggestive voice that caused my cock to throb as I remembered being put over her knee.

I wished I had some clever comeback for her comment but I just flushed red and carried on with my drink as Emma kept talking.

"Maybe I should message your Mistress and ask her for a repeat performance."

"No! Don't you dare message her. You've already gotten me in enough trouble as it is with the outfit."

"Oh please! I'm just helping you fulfill your desire Mike. Your desire to become a cute little sissy."

As I said this, I looked down and saw one of Emma's feet slowly rubbing up and down my inner thigh. I was stood facing the counter, while Emma was sitting right next to me, facing outwards as one of her feet had moved in between my legs. I know I should have moved away and stopped her right then, but I was in a horny daze as I let her continue to tease me.

"You can deny it all you like Mike. But without your cage, your cock gives you away." Her foot continued its slow rubbing just inside my thigh, gradually moving a little higher with each upwards stroke.

Eventually, she pulled her foot away from my legs, deliberately grazing past the end of my erection as she did so, causing me to visibly shudder in arousal at the minute contact.

"Guess we'd better get back to work Mike. Wouldn't want you making a mess in your panties now would we?" Emma said, hopping off the counter and brushing past me as she left, I couldn't believe that within a day of being released from chastity I was already wishing I was locked back up. At least while in chastity my erections couldn't give me away so easily, and everything that was happening was turning me on. I had to fight a near constant urge to go and rub one out in the toilets the whole day at work. There was no way I could let myself get that desperate, regardless of Emma's constant teasing.

Finally, the work day ended so I could get out of here and 'relieve' myself once again. Might as well take advantage while I'm out of the cage. I was just heading out when Emma stopped me.

"Oh Mike, I have some things for you in my car that I thought you might like. I'll drop you off home so you don't have to carry them all the way home."

This was something I wasn't expecting. "Oh, umm. Thanks." I almost asked what it was but I was afraid of Jake hearing the answer, so I waited for Emma and we walked together to her car.

"So, what is it you brought me?" I asked as we made the short drive to my apartment.

"Just a few more clothes you might need. Can't have you wearing the same outfit everyday can we?"

"Emma, I don't need more clothes! I need to get rid of this program. It's gone far enough, I've spent the whole day dressed in womens clothes and-"

"And you were hard the whole time!" Emma cut me off. "The sooner you admit that you love this the better." She said in a matter-of-fact tone.

"Fine, I like the kinky side of it ... obviously. But I don't want that to bleed into my work life." I admitted, I couldn't exactly hide it right now with my erection once again making itself known.

"Then you should have been more careful with what you installed onto your smart speaker. Now, grab your bag from the trunk and I'll see you tomorrow. It's Friday so if you wear something pretty then lunch is on me." She said with a smile.

"Fine. I'll see you tomorrow." I said, petulantly. As I made to leave I felt Emma's hand give my ass a quick squeeze.

"Sorry Mike, couldn't resist." I grumbled a nothing response and headed to the trunk of Emma's car where I saw a large duffel bag that looked like it was stuffed full. I grabbed it and headed back up to my apartment to inspect the contents.

As I got to my front door, I noticed I had another small parcel in the cage, so I took it inside along with the bag.

"Hello slave. You should have received another package. This is a second smart speaker that I require you to set up in your bedroom. Preferably somewhere close to your bed. This must be done immediately."

Why the hell did she need another speaker in my room? I could pretty much hear the living room speaker anyway if I turned it up loud enough. But fine, whatever. I thought about getting another one anyway. It didn't take long to plug in and log in to the new speaker on my bedside table.

As soon as I had done that, I grabbed Emma's gift and emptied the contents onto the bed. As expected, it was a selection of female clothing.

I laid the items out on the bed to take a look. There were a bunch of shirts, similar to the one I was currently wearing but in different colors. A few pairs of pants that could be worn to the office, plus a couple of pairs of shorts that I had a hard time believing Emma would ever have worn, even a few black office skirts. A pile of underwear in different styles, designs and colors plus various different stockings and pantyhose. Even a couple of bras that had to have belonged to Emma as the cup size was obviously way too big to fit my flat chest. I had no idea what to do with all these clothes, but apparently Mistress did.

"It looks like you have been shopping slave. My camera footage shows me that you have a selection of new clothes to wear." Her voice came loud and clear from the new bedroom speaker.

"No Mistress, these were another gift from Emma." I said, glumly.

"Excellent. Now you have a selection of clothes to wear to the office."

Great, it looked like I needed to get used to going to work in womens clothes. As long as I could avoid the skirt I should be fine.

I bundled all the clothes away into the bottom of my wardrobe in an almost neat pile before deciding what to do with the rest of the day. With how much I had been teased by Emma at work, there was really just the one thing on my mind to start with.

I sat down at the laptop in my bedroom and booted up my preferred porn website. I didn't get very far however, as a small pop up appeared whenever I tried to click on anything.

'Access to this website has been blocked by your administrator'

What?! I didn't remove access to anything. This was my personal laptop, I didn't even have an admin account set up.

"Slave, I can see you are trying to access content that is unsuitable for you."

"Unsuitable? Mistress, did you remove access to certain ... websites?" I asked.

"You mean pornographic websites. Yes. I did. As you are currently free from chastity, you are of course free to consume as much pornographic content as you like. However, I must make sure that the content is in line with your current situation."

"My current situation? My current situation is ... horny! Mostly thanks to you. And now you're saying I can't even watch the porn I like?"


"If you would like to view some pornography, I can queue some up that I'm sure you will enjoy. Would you like me to select some pornography for you?"

"Yes. Fine, go ahead." I said, my cock was already hard and waiting so I wouldn't need long anyway.

A new window opened on my laptop, this one showing a website I wasn't familiar with. Before long, a video started playing, it looked like one of those pointless 'femdom hypno' files that a lot of websites had. I had seen a few in my time but none of them ever really had any effect, they were mostly just flashing images and repeated phrases or words flashing on the screen.

This one was a little different, after a few minutes of watching I realized that a lot of the images had a sissy theme to them. There were quick flashes of female dommes with male sissies. Short video clips of powerful women spanking and humiliating pantied men, in some of the clips the women were even fucking their sissified men with a strap on cock. I had to admit that these images were all turning me on.

The whole video was undercut by a calming, female voice over, constantly encouraging me to relax and enjoy the images of submission on the screen. It didn't take long for me to start stroking my cock, engrossed in the pictures and short videos. Some of the pictures were just of extremely feminine feminine clothing. Something I figured no actual girl would ever wear, images of bright pink panties with numerous ruffles on the seat and frilled edges along with bras and stockings to match. These were obviously designed just to be humiliating. Which of course meant that I got more turned on by them.

It didn't take long for me to cum into the tissue I had been holding, moaning slightly out of relief.

As soon as I had released the tension and came down from the post orgasm high, I reached over to turn off the video and get back to my day, but all I heard was the annoying 'Bing bong' that suggested I had done something wrong. I couldn't click anywhere on the screen! Nothing alI did would stop the video from playing, even the keyboard shortcuts were met with an error tone.

"Slave, you still have 45 minutes left on your pornographic video. You must watch until the end before you leave the seat."

Was she serious? I thought to myself. 45 minutes more I had to sit here and watch a video that had already served its purpose.

"But Mistress, I'm er, finished. I think I need to get showered and changed now."

"You will remain in your seat until the video is finished, slave. Failure to follow my orders will result in punishment."

Well ... fuck.

Thanks to the camera in my room I had no chance of leaving the laptop without Mistress knowing. I didn't even have anything else within range to occupy me, and I couldn't control the volume of the video either so it wasn't like I could just stop listening.

"You are a sissy. You long to be wrapped in feminine things and treated like a whore for your Mistress."

The voice from the laptop continued as I had nothing to look at but the constant barrage of images and sounds. At one point I swear Mistress must have been turning up the volume as the words were becoming clearer and louder. Trying to read the flashing phrases on the screen while listening to what the voice was saying proved difficult, so I kept drifting between one or the other as I watched the video.

A sissy being spanked over his Mistress' knee. A sissy in a maid's outfit washing dishes with a happy smile. A sissy dressed only in pink panties and stockings, on their hands and knees being used as a footstool by their Mistress. A ridiculously frilly pink outfit. A long purple dildo. A butt plug.

These were all images and videos that flashed by as I was forced to keep watching the video and listening to the voice.

"You are a sissy, and sissies love to be controlled."

"Sissies love to have their ass filled."

"A sissy is always happiest when serving their Mistress."

"A sissy should have their little clitties caged."

I kept trying to distract myself from the video but there was nothing else to keep my focus without leaving the chair. No matter where I looked, the sounds and flashing images pulled my focus back to the screen. I looked at the remaining time on the video, 15 minutes. That was when I noticed that my cock was once again hard. 30 mins of being stuck watching had clearly had an effect on me.

Fuck it. I'm stuck here, no better way to kill time. I resumed the stroking of my cock, trying to keep a slow steady pace to enjoy this latest bout of self pleasure until the end of the video.

"A sissy should always be in sexy panties"
A picture of a lacy thong.

"A sissy has a little sissy clitty. A sissy does not have a cock."
An image of a small, pantied dick squeezed into a chastity cage.

1 minute left of the video and I was close to cumming again as I was assaulted with sissy sights and humiliating mantras.

"Sissies love to suck."

"Sissies are always horny"

"Ooohh fuck!" I moaned out loud as I came for the second time in an hour. I came down from the orgasm as the video finally came to an end.

"I hope you enjoyed your video, slave. Please feel free to ask again the next time you need to masturbate."

I would be sure to be careful about that. The thought of asking a 3rd party to select my porn for me whenever I needed to jerk off was not that appealing to me. But hey, at least I could jerk off for a change.

I was finally able to leave the chair and actually spend a mostly relaxing evening to myself, free from sexual frustration and humiliation. Eventually falling asleep with a content feeling.

For some reason I didn't sleep very well, I kept waking up through the night, tossing and turning. I had vague memories of opening my eyes and seeing the glowing ring of my newest smart speaker and hearing a faint voice. But I never stayed awake long enough to investigate further, but I did wake up feeling extremely horny for some reason.

I was instructed to dress for work in some of the clothes that Emma had left for me, so after rifling through the bag to find the least feminine items I could. I was dressed and almost ready to go.

I had managed to find some more black office trousers, similar to yesterdays except these ones had a zipper in the back. There was a green, long sleeved shirt that looked like it would do fine, the color wasn't something I would usually go for but it was the least feminine style. After yesterday's issues, I wasn't keen on wearing a thong again so I opted for a brief style panty instead. A light blue satin feel pair that squeezed my ass a little, but did a much better job of containing my junk than the thong did.


"Morning Emma." I said as I walked into work, forcing myself to be as casual as I could, even though I could feel a small surge of heat in my cheeks as I saw her. I was determined not to let her get to me today.

"Morning Mike. Cute outfit." Was all she said in reply as I walked to my desk. I didn't respond to her comment, not even looking at her as she spoke, even though I could feel her eyes on me as I passed. I knew she would have had more to say, but with Jake already at his desk she had to be cool, at least for now anyway.

As expected though, she soon found her way into my workspace, sliding her chair right up next to mine.

"I'm a little jealous sissy boy, those clothes look better on you than they did on me." Emma said, leaning in close to get a good look at my legs under the desk. Of course, her proximity and obvious staring caused my cock to start stirring.

"What can I say? I make everything look good." I said with a false confidence, I would not let her get to me.

"Oh I'll bet you do. I can't wait to see you in the office with a nice skirt and some stockings. Now that would look good on you." Emma said as she started slowly tracing a small pattern up my leg with her fingernail.

"Never gonna happen!" I said, but I wondered what I would have to do to stop that from actually happening. If Mistress decided that's what she wants, then could I really say no at this point?

"We'll see." Emma replied, gradually moving her wandering finger further towards my crotch. By now, her attention had my cock fully erect and clearly visible as it pushed out on the tight pants.

"It looks like some part of you likes the idea." She said, obviously eyeing my crotch.

"You know full well why that is, so why don't you cut it out and get back to your desk." I said, although I made no move to actually stop her fingertip from trailing right up near the tip of my erection.

"Oh really? Is it my fault that you're hard right now. Or maybe it's because sissies are always horny."

'Sissies are always horny'

I felt a surge of arousal at Emma's last phrase, I felt like I had heard it before. But I wasn't sure where. What's more, Emma was now openly tracing her finger and up and down the length of my erection, the tightly stretched material of the trousers doing nothing to mask the sensation.

"Is that what it is, Mike? Are you just a horny sissy?"

"No! Emma, you have to ... please."

"I have to what, Mike? I have to stop? I have to keep going? Which is it?"

I honestly did not know the answer to that question right now. I was hornier than usual from the moment I woke up, and Emma was slowly applying more pressure as she kept idly stroking my erection.

"Emma...Please, you have to stop or I might.."

"You might what? Fill your panties with your sissy cum. Is that what you might do Mike?"

"Yes. Yes, that's exactly what will happen if you don't stop doing ... that." I admitted, with some difficulty.

"Is that what you want to happen? You could have stopped me at any time Mike. You're stronger than me, right? Physically at least. But there's only one muscle that's working for you right now isn't there? And it's this muscle that tells me everything I need to know." Her finger was pressing more insistently at my erection now. I was actually starting to feel like I would cum if she kept it up.

"Is that what you want? Sissy! Do you want me to get you off?"

"Y-Yes!" I said, a little louder than I would have liked. I wasn't thinking straight anymore. All I could think about was how close to cumming I was, I would deal with the consequences after.

"I thought so." Emma said, quickly removing her hand from my crotch, leaving me desperately close to orgasm.

"Well Mike, I'd better get back to work." She said loudly, wheeling her chair back over to her own desk.

I stared at her, longingly as she settled back at her own station, just long enough to see her mouth the words "Too easy." at me.

I guess she won this round. I spent the rest of the work day desperate for relief and constantly distracted by my situation. But I would not lower myself to rubbing one out in the bathroom at work.

I briefly wondered if it would be better for me to be in the cage, then maybe I couldn't be manipulated so easily. With my cock free, I had no way of hiding how much I enjoyed this. The only problem would be that I didn't have the login info for the app that controlled the chastity cage, meaning I would have to ask Mistress to lock me back up. Was I really so hopeless that I was going to ask to be locked in chastity, after spending so much time trying to get out?

'Sissies should have their little clittys caged'

Where did that thought come from?

End chapter 1