Digital Dominatrix 2.0 chapter 9 (Patreon)

Digital Dominatrix 2.0 chapter 9


Friday morning, I woke up with the cage feeling extra tight around my crotch. This was becoming a familiar feeling. I mean, everybody knows about morning wood, but this seemed different somehow. I was always extra horny after waking … Did this have something to do with the weird voices I could hear in my sleep?

I got dressed in the feminine pants and a clean blouse, over the top of the usual bra and panties combination that I had become accustomed to….I still had the tan lines to prove it!

Just the sight of all the pretty, lacy and ultra feminine panties in my underwear drawer caused a brief spike of arousal to shoot through me. I had always had a bit of a fetish for panties anyway, but this felt different. Like just the sight of a pair of panties nowadays was enough to turn me on. Not that you would know it with the cage keeping my cock under control.

Femmed up and ready to go, I headed out to work with thoughts of what the day might bring, keeping me occupied on the way there. I already knew what I would be doing this evening of course, Mistress and Kate had made sure of that.

“Morning Emma.” I said as brightly as I could as I entered the office. My cock gave a small twitch in the cage at the sight of her. I was a little concerned at this, I figured that Emma had been responsible for so much of my teasing and torment lately that just the sight of her was enough to cause a small spark of arousal. Of course, last night’s teasing session didn’t help.

“Good morning, sissy. I take it you had a fun evening, haha.”

“You know exactly how ‘fun’ my evening was!” I replied grumpily, referring of course to the fact that Emma had had a hand in the teasing punishment I received last night.

“Well then, perhaps you should behave yourself a little better. Although I did enjoy watching you squirming on the bed like that, I only wish I was there to see it in person. Ah well, maybe we’ll have to have another sissy sleepover sometime.” Emma said, with a hint of expectancy in her voice.

“Yeah I guess we will.” I replied, without really thinking about it. Truthfully, another night serving Emma sounded like fun, even if it might end up with me being locked and frustrated the whole time.

“What was that, Mike? You guess ‘we will’ what?”

“A sis-er, a sleepover I mean. That’s what you said right?”

“I did, and it sounds to me like you like the idea.” Emma’s face had lit up by this point, it was obvious she had led the conversation here on purpose, probably to gauge my reaction in case she was pushing too far, and I had just given myself away.

“Well, I mean if you wanted to…” I said, trying to sound less eager than I actually was, but it was too late for that, and we both knew it.

“Oh I definitely want to, and it’s obvious you want to. So why don’t you come over again this weekend? How about Sunday night? That way I can bring you straight to work on Monday morning.”

“Umm, yeah I guess that would be okay.” I said, feeling my clitty twitch once again in its cage.

“Great! I can’t wait!” Emma said, quickly lifting up her phone and typing away.

“What are you doing, sending me a calendar invite?” I asked, sarcastically.

“Actually I was just sending a message to your Mistress about this weekend.”

“Wait, what?! What message?” I asked quickly.

“Just a sec … oh good, she replied. Mistress and I have decided to make sure you stay locked until Sunday, so if you’re extra well behaved I might just be able to give you a little treat at the end of the night.”

“What! So now I have to wait until Sunday?” I replied, incredulously. I was already desperate for a little relief after the last couple of days locked up. I figured Emma had a plan for Sunday night and knew that I would be extra compliant if I was as desperate for release as could be.

“Yes … But only if you’re a good girl for me, remember. Otherwise I could just send you home all horny and frustrated.”

Dammit! Once again Emma had played me, and that meant that even though I would be spending the evening with Kate today, I would be doing it in the cage with no chance of release.

I spent the rest of the day trying to focus solely on my work, trying my best to keep myself distracted from the near constant ache from below. As I typed away I couldn’t help but notice how my nails could use a touch up, the polish was cracked in places and the natural nail color showed where they had grown out a little.

‘My nails could use a touch up.’ Did I really just think that? Was I so far gone that the thought of getting rid of the feminine nails didn’t occur to me before the thought of touching them up.

As I diligently worked away, I heard Emma slide towards me on her chair.

“Hey sissy. Need a quick favor.” She said as she rode her chair into my booth.

“What’s that?” I asked, obvious trepidation in my voice.

“I have a new shade of lipstick but I’m not sure I like it, I need to see what it looks like on someone else, and you’re the only one here so….pucker up.” She said, holding a tube of dark red lipstick into front of my face.

“No way! Try it on yourself first, you never hear of a mirror?” I said, leaning my head back slightly to avoid the lipstick.

“Yeah but I need to see it on someone else’s lips before I make my mind up. And don’t worry, it’s not like there’s anyone else here. If you don’t like it you can go wash it off right away. Come on, Mike … Be a good sissy.”

‘I am a good sissy.’

The thought popped in my head as soon as Emma said the words, I actually had to stop myself from saying them out loud. I wondered where the hell that had come from, but in my moment of hesitation brought on by the term ‘good sissy’, Emma had begun to paint my lips in the dark red colour.


“...Thaaat’s a good girl. Just hold there while I paint your pretty lips a nice color.” Emma said, leaning ever closer to me as she spoke.

I wanted to resist, to protest in some way, but Emma’s proximity and her words had my cock pulsing and my heart pounding as I had the lipstick applied to me in an almost tender act. Emma’s face was inches away from mine and she had one hand rested on my thigh for support as she leaned towards my lips which were parted in surprise. The worst part of course was how much this whole situation was turning me on. Emma backed her head away from mine slightly to observe her work.

“Now, purse your lips a little and make like you’re blowing a kiss. “ She said, staring at my lips.

I did as she asked, if a little hesitantly, much to her delight.

“Ohhh you know what, that looks perfect on you! So good I think you ought to have it.” She said, popping the cap back into place and pressing the lipstick into my hand.

“umm, thanks but I er, I don’t think I need any-Mmmf.” My sentence was cut short as Emma had leaned in and quickly planted a tender kiss right on my newly painted lips.

My breath caught in my throat and all my thoughts were immediately scrambled by the kiss. Emma held her lips against mine for about 4 long seconds before pulling away, leaving me desperately horny.

“Mmm, sorry about that, Mike. I just couldn’t resist, your lips look so nice and kissable like that. You wear that to my place on Sunday and I don’t think I’ll be able to keep my hands off you.” Emma said, finishing her sentence with a wink as she slowly backed away from my desk, her hand that was resting on my thigh sliding down my leg as she did.

“Th-thank you.” I squeaked out a rather embarrassing response, not quite sure what I was even thanking her for. Was it for the lipstick, or for the kiss? Who knows. All I knew was that I was too horny to focus on anything for the rest of the day, and wound up completely forgetting to wipe off the lipstick right away. After finishing up a quick bathroom break, I stopped in front of the sink and looked at myself in the mirror. The dark red colour was obvious on my lips, and somehow made the whole lower section of my face appear more feminine, probably helped along by the lack of any facial hair. I considered just wiping it off there and then, but then the memory of Emma's kiss came back to make me reconsider.

Clearly she liked it on me, and for some reason I felt a small part of me that actually wanted her attention. Whether it was affectionate or teasing, I liked that she noticed me. With this in mind, I left the lipstick in place as I left the bathroom and headed back to my desk.

“Well it looks like you didn’t immediately remove your lipstick, Mike. I knew you’d like it!” Emma said as she walked past my desk on her way to the bathroom.

I didn’t have time to argue with her about liking the lipstick, but what would I say anyway? I couldn’t tell her that I only left it in place because I craved her attention.

The rest of the shift passed uneventfully enough, Emma would keep turning in her chair to stare in my direction, presumably to see if my lips were still painted or not. At one point she even blew me a rather suggestive kiss, which caused my clitty to tingle and my cheeks to flush.

I packed up my desk at the end of the work day and prepared to head home for the weekend.

“Well, I guess I’ll see you on Sunday?” I said, uncertainly as I headed towards the door to the elevator.

“I can’t wait. I’ll pick you up around midday, how’s that sound?”

“Great, see you then. Bye.”

“Bye bye, sissy. I hope it won’t be too ‘hard’ for you having to stay locked until Sunday, hehehe.” Emma decided to get one last little jibe in at my expense before I left the building. As if I needed to be reminded of the fact that I would be trapped in the cage all weekend.

I spent the walk home trying to distract myself from thoughts of Emma, and focus on Kate, who was the most pressing issue for the night. Kate had already made it clear that she didn’t mind my ‘kinks’, but she had never seen me in a full maids outfit, and she didn’t know about the cage. How would she react to that? I wondered to myself as I made my way up to my apartment.

A quick glance up and down the hall to make sure the coast was clear, and a quick flash of my bra and panties later, I was back home in my apartment.

“Hello Mistress.” I said as usual.

“Welcome home, sissy. Do not forget you are scheduled to provide maid service tonight for your neighbor. I will let you have a couple of hours to yourself before I give you instructions to prepare for your evening.” Lucky me.

I made sure to grab something to eat and lounge around in my male clothes for a while (except for the panties of course, they stayed on.). As I was in the bathroom I noticed that I had forgotten to take off the lipstick from earlier! Which meant that I had walked home with it still in place, had people noticed? I quickly wiped my lips clean, slightly annoyed at Emma for playing me so easily.

I was just enjoying a little TV for a while to keep my thoughts from straying to anything sexual, when Mistress spoke up.

“Sissy, the doorbell camera indicates that Kate has just returned home. Therefore, you are to begin getting dressed for the evening. Make sure you have on your full maid ensemble, complete with bra, panties and stockings.”

Well, showtime! I thought as I headed into the bedroom to get ready. I was getting used to donning the maid attire by now, so it didn’t take me long to get dressed in the black dress with the frilly white apron. Once the stockings were rolled up my legs into place I wondered what to do next. I didn’t have to wait for long however, as Mistress spoke up again.

“Very good, sissy. Now put on your heels, and lock them in place, before securing the keys inside your lockbox. You will be allowed to remove the heels upon returning to your apartment.”

Shit! I guess I was going all in for tonight. I figured complaining about this addition to my uniform would be pointless, so I simply went ahead and did as I was told. Kate was in for a hell of an evening!

After getting the heels on and locked into place, I sat on the edge of my bed and waited, wondering what I was supposed to do now. Did I just run across the hall in the outfit and knock on Kate’s door? I didn’t like the sound of that, I needed to make sure she was expecting so as to reduce the risk of anyone seeing me dressed like this.

As it turned out, Mistress had this covered too.

“Sissy, Kate has sent a text message indicating that she is now ready for you. Please head over to her apartment as soon as possible.”

Here we go….,


I took a deep breath before leaving my apartment, sticking my head out the door to make sure there was no one else in the hall. I quickly walked the couple of steps to Kate’s door and knocked quickly, silently praying that she would answer as fast as possible.

My heart was pounding as I stood outside Kate’s door in my sissy outfit, waiting for her to answer.

‘Knock! ‘knock! ‘knock!’ I knocked once more, trying to will her to hurry up as I shuffled from foot to foot.

Thankfully, the door opened after a few seconds more, and I was now waiting with bated breath as Kate took in the sight of my sissified self.

“Well, Get a load of you! Hahaha.” Kate said, allowing herself a short laugh at my expense. “I'm sorry for laughing, it's just, well….this is a surprise.”

“Yeah I guess it would be, can I come in please? I feel a little exposed out here.”

“Yeah I guess you'd better get in here and get to work.” Kate said, standing aside to let me in.

“Wow, heels too huh…wait are those locked?” She asked, staring at my feet.

“Yeah well, I guess it adds to the thrill.” Was all I could think to say.

“Wow, very sexy!” She said, before adding, “Sooo this is a little new to me. Wanna tell me what the deal is or….?”

“Yeah I'm not really sure myself, I don't really do this regularly.” I said, not a total lie really.

“But this is a turn on for you right? Like you get off on being all girly?”

“Well yeah I guess, it's more than that though I think, I guess I like the feeling of being a little embarrassed, like a humiliation kink…It's weird I know.” I explained, understanding that this had to seem more weird for Kate than it was for me by this point.

“Not as weird as you might think. And like I said, I'm not one to kink shame. I just needed to make sure we're on the same page, now that we're clear that you like being embarrassed, I think you'd better get to work….My little panty maid.” Kate said, her expression turning into something far more devious.

“Yes Ma'am.” I said, leaning into the role a little, I guess I may as well enjoy myself while I was here.

“Ooh, Ma’am! I like that. Keep it up girly.” Kate replied with a smile. “Well I guess you better get to work then, maid. I made sure not to do any tidying up for the last couple of the days in preparation for today.

Kate was clearly not lying, there were empty soda cans and snack packets scattered around near the couch as well as some laundry that had just been casually tossed aside. Not to mention the pile of dirty dishes that had just been left near the sink. It looked like I had some genuine maid work to do.

I decided to get to work and start by taking a trash bag and gathering up all the rubbish that was dotted around, Kate watching me intently the whole time.

“I could get used to this treatment, you know.” She said as I moved around her living area. “Are you enjoying yourself being my maid?”

“Well I guess I would be … If you weren’t such a slob!” I replied.

“Hey! Why would I waste my time tidying up when I have a maid coming over?”

“Yeah, yeah. Don’t get used to it!”

“Aww don’t be like that. I bet you’re loving this, you big perv!” Kate said, reaching a hand up the back of my skirt and squeezing my ass as I passed by her, this caused me to jump me forward a little to avoid her hand. “Aww, what’s wrong pantyboy? Got something hidden up your skirt? Or maybe you don’t want me feeling how hard you are under there, is that it?” If only she knew.

I figured Kate would have to find out about the cage at some point this evening, I just didn’t know how she would take it, she had been pretty cool about all this so far.

“Yeah, something like that.” I replied as I bent over to pick up an empty chip packet from the ground. I felt a quick smack on my ass as the dress rode up enough to flash the white ruffled panties.

“Ya know, your legs look great in that outfit, you make a pretty girl, Mike.” Kate said in a teasing voice.

“Thanks.” Was all I said in response.

“No really, I’m a little jealous of those legs of yours. But there’s something missing…” Kate mused as she eyed me intently, making me a little nervous. Kate may not have known as much about this side of me as Emma, but if there’s one thing she was good at, it was teasing me. Kate seemed to get an idea as she snapped her fingers and declared, “I got it! Follow me, maid.” before turning and heading towards her bedroom.

I wondered what idea she had just had as I followed her to her bedroom. She led me over to her makeup table that was in the corner of her room and patted the chair that was in front of it.

“Come take a seat.” She said, leaving me in no doubt as to what she had planned. I did as Kate told me and lowered myself into the chair, eyeballing the various items of makeup scattered around. I didn’t have a chance to study them however, as Kate quickly sat herself down right on top of me, she was straddling my lap so we were face to face, blocking my view of the mirror and table behind me. Kate's position and closeness was doing a hell of a job on my poor locked up cock.

“I think a little makeup is needed to complete your look.” She said, turning around grabbing something from her makeup desk. I could feel Kate’s ass pressed right up against the chastity cage as she went to work on my face with a brush and some type of powder stuff.

I sat quietly as my cock pulsed away in the cage while Kate worked on my face. I took note of what she was doing, trying to identify the various items she was currently slathering my face with. Foundation, blush, mascara, eyeshadow and a super thin marker pen type thing she used on my eyebrows. I simply sat there and admired Kate as she worked.

She seemed to be almost finished as she declared she had ‘one more thing’ to do. The ‘one more thing’ turned out to be a shiny tube of pink lipgloss that she applied lovingly to my lips.

“Not bad if I do say so myself.” Kate said, leaning back slightly to admire her work. “This is a plumper, it will help your lips plump up a little, making them extra kissable!” Kate punctuated her point by leaning in and kissing me hard on my freshly painted lips. “Whoops! Better touch that up.” She said as I noticed some of the sticky feeling lip gloss had been transferred to Kate’s own lips.

As Kate rocked a little in my lap, I realized there was no way she couldn’t feel the cage beneath her butt.

“Mmm, what’s this I can feel?” She said, slightly gyrating her hips as though trying to get a feel for my crotch with her ass cheeks. “Are you getting hard from me doing your makeup, pantyboy?”

I was too horny to stop and think about my next words. “Oooh fuck, I wish!”

“Wait … what do you mean, you wish?” Kate asked, her expression switching to one of confusion. “Are you saying you’re not turned on by this?”

“Oh no, that’s definitely not it.” I said quickly, “It’s just that, I kind of can’t get hard right now.” I finished in a small voice.

“Well something feels hard to me.” Kate said, sliding backwards off my lap and reaching for the hem of the maid dress.

I decided to remain quiet as Kate rummaged through frills and the petticoat to find my panties, I figured I may as well see what she made of the chastity cage.

“W-what the hell is this? Is your dick locked away?” Kate said as her hand got a firm grasp on my cage.

“Yeah … It is.” I replied in a small voice.

“Why the hell would you do that? I thought tonight was about, you know.”

“It is! I mean, this is part of it. I guess I decided to go all in with the kink stuff, see if it scared you off.”

“So you like having your dick locked away?” Kate asked, still standing in front of me, still blocking my view of the mirror.

“I wouldn’t say I like it. I guess it’s more of a way to … prolong the fun. Keep myself denied for a while you know.”

“Ooooh so you're one of those guys who likes being teased for a while. So I’m guessing that cage is making you extra horny?”


“You have no idea. Right now I’m starting to think putting it on was a terrible idea. But it’s digital, and I can’t take it off until at least Sunday.” That was all pretty much true, I guessed.

“Aww that’s a shame, I was hoping to have a little fun tonight.” Kate said, “And all this is getting me a little turned on.”

“Good! I wanted you to have fun, and errm, I can … You know. I can take care of you.” I said.

“Ohhh don’t worry, you will. I’ll make sure of it! But not right away, it might mess up your makeup.” Kate said with a smile, before stepping aside so I could finally see what she had done.

I stared, shocked, at my reflection. The feminine look was damn near complete. My lips were shiny and pink and I could feel a small tingling as the plumping solution did its job. My cheeks were rosy and the foundation had smoothed out my whole complexion, making my face appear softer and smoother. My eyes were smoky and alluring with thicker lashes, topped by more defined, sharper eyebrows.

“Whaddya think?” Kate asked after a pause.

“Not bad.” I said, the truth was I was shocked, my masculinity was slowly being replaced.

“Damn right not bad! Now get up girly, you still have work to do. You can start by gathering up all these clothes for the laundry. Chop chop, maid.” Kate said, gesturing to the random items of unwashed clothes she had left scattered all over her bedroom. “Oh, and don’t steal any of my panties, hahaha.”

Kate headed back out into the living room as I got to work collecting all of her previously worn clothes. Of course I would never consider stealing her panties, but something about being allowed to just pick them up and feel them, knowing they had been worn by her, was turning me on a little more as I worked … Then again, everything turned me on these days.

I finished gathering up the clothes and left them all in a hamper in the corner of her room before heading out to where Kate was lounging on the couch.

“Oh good, now you’re here you can get me a drink before you get started on the dishes.” Kate said with an overly sweet smile as I entered the room.

“I think you’re enjoying this a little too much.” I replied, heading to the fridge to find something to drink.

“Don’t act like you’re not loving it too. I’ll bet you would be hard as rock under that frilly dress of yours if it wasn’t for … you know.” She had me there. I handed her a drink and headed back to the kitchen area to get started on dishes. I could feel Kate’s eyes on me as I moved around her apartment.

“You’re pretty confident in those heels. I take it you’ve had practice?”

“Yeah I guess you could say that.”

“So, why lock them on?” She asked as I worked away at the sink.

“I guess for the same reason as the cage. The keys are in a time locked box over at my place. I suppose whenever I indulge myself in these fantasies it’s always too easy to get too turned and if I had the keys too readily accessible I would just unlock myself before I knew it. This way I can’t unlock myself right away so I get the full experience.”

“Well, no complaints here. I may have to let you clean up around here every weekend. Who knows, maybe next time without the cage.” Kate added with a wink as I finished washing everything that was near the sink.

“Well, that’s the dishes done. Anything else?” I said as I dried my hands.

“Good job, maid. The place looks a lot better, but now I think I need a little attention over here. I’ve had a long day at work and my poor feet could use a little TLC. But I don’t have to tell you, I’m guessing you already know exactly what it’s like to be walking around in heels all day.”

I ignored Kate's latest remark and approached her on the couch, she swung her bare feet around to the side so she could lay them in my lap, giving me easy access.


“Mmmm, that’s nice. A clean up and a foot rub, I know people who would pay good money for your service. Maybe I could rent you out to my friends.” Kate said as I gently massaged her feet.

“No way!” I replied quickly, there was already two too many people who knew what was going on.

“Hahaha relax, Mike. I’m kidding, your sexy little secret is safe with me. Besides, I like having your services to myself.” Kate let me keep massaging her feet for a while, enjoying my attention as I could feel my own feet aching in the heels. My poor locked up cock was aching to be free from the cage the whole time.

“Mmm. All this special attention has gotten me a little worked up, I think it might be time for you to, how did you put it? ‘Take care of me’.” Kate said with a lusty look on her face.

“Yes Ma’am!” I replied, enthusiastically. Even though I knew it would be torture for my poor clitty, I was eager for a chance to pleasure Kate again.

“Then get to work, panty boy!” She said, spreading her legs open so one foot was on the floor with the other over the back of her couch. All she had on was an oversized hoodie that came down to just below her butt, which was covered only by a pair of very short shorts.

It didn’t take me long to get the shorts out of the way, giving me full access to her nether region. I adjusted my position on the couch and brought my head down to get started. I could immediately tell how turned on she was by how wet she was. The taste of her was heaven to my lust addled tongue and I could feel the lip gloss I was wearing being smeared all over her pussy as I went to town pleasuring her.

I happily lapped away at Kate’s pussy until I felt her body tense and she let out a long moan as she came hard against my made-up face.

I stayed quiet for a few moments as Kate got her breathing under control, eventually looked up at me and let out a small laugh.


“Hahaha, that was great, panty boy, but you may have to touch up your makeup, I think all your lip gloss has rubbed off somehow.”

“Yeah I wonder how that happened.” I replied in a sarcastic tone.

Kate and I spent the rest of the evening watching a movie together on the couch, she didn’t let up her teasing and insisted I keep the outfit on, like I had a choice, but aside from that, it was a mostly normal hang out for us both. Normal except for the fact that I had no way of getting any relief of my own. I knew then and there that I would definitely have to be on my best behaviour for Miss Emma on Sunday.


—


Meanwhile, a couple of miles away, Emma was sitting at her computer typing away at something. She was giddy with excitement for the coming weekend, it had been so long she had had a sissy to toy with, and her latest project was coming along nicely. She knew she couldn’t rush things or push him too far, she would have to remain patient, but she needed to make sure Sunday was as fun as possible … for both of them.

With that in mind, she booted up the Digital Dominatrix program’s root menu and input her moderator password, giving her full access to the program that was currently running on Mike’s digital assistant.

The algorithm that controlled and made decisions for the AI was one of her most prized creations, it made sure that the Mistress program could queue up multiple activities and requests, and allocate suitable punishments for each one in less than a second. Emma looked through the currently planned activities on Mike’s program, specifically the one’s scheduled for tomorrow.

“Not bad Mistress, but I think I’m going to have to make a few small changes to Mike's schedule in advance of our Sunday together.” She said to herself as she got to work rearranging the commands Mistress had queued up for tomorrow. She didn’t like interfering with the program while it was already running, who knows what bugs might turn up, but she figured she could get away with it, just this once. After all, she needed to make sure her sissy was fully prepared for Sunday. One thing was for sure though…

Her sissy was in for a fun weekend.


End Chapter 9.