Digital Dominatrix 2.0 chapter 11 (Patreon)

Digital Dominatrix 2.0 Chapter 11


The rest of Saturday passed without being given any more tasks by Mistress, but with how horny all my ‘training’ had left me, I was almost too distracted to focus on anything else. I woke up on Sunday morning with my caged up clitty throbbing in its cage. The remnants of that sweet voice I had been hearing in my sleep were still echoing in my head.

‘...You are a sissy.’

It took me a few minutes to bring myself around this time, it felt like my mind had woken up after the rest of my body.

When I had finally dragged myself out of bed, I got dressed and began nervously anticipating the day ahead. I knew that I would be spending the day with Miss Emma again, returning to my maid duties no doubt. I also knew that I had to be on my best behaviour if I wanted to get out of the chastity cage.

‘...Good sissies should be caged.’

I went to my underwear drawer and picked out a pair of panties to wear for today. It felt like so long ago that the drawer used to be filled with boxer shorts, putting on panties just felt so natural to me now that I don’t even know if I would choose boxers even if I had the option.

“Morning Mistress.” I said as I entered my living area and headed towards the fridge to grab a little breakfast.

“Good morning, sissy. Don’t forget that you are scheduled to serve Miss Emma today. Did you wash your maids outfit as instructed?”

“Yes Mistress.” I replied, feeling my knees bend a little as I replied ... .Did I just try to curtsy?? That one almost came without me thinking about it. How far had I come down this path that I was curtsying to a damn AI speaker?!

I had washed my maid outfit last night and packed everything up in a bag ready to take to Emma’s for the day. All I had to do now was wait. I checked myself over in the mirror and stared hard at my lips. They were definitely fuller, more feminine, not to mention my newly shaped and tinted eyebrows meant that my face was a lot more feminine than it had been a few days ago.

At some point in the late morning I got a text message from Emma, letting me know that she was on her way to pick me up. I was wearing some loose sweatpants and a hoodie as I left carrying my bag, knowing that I wouldn’t be wearing these masculine clothes for very long.

I waited in the parking lot and watched Emma's car pull up, my penis gave a little jolt as I saw her face through the windshield. I guess after all the teasing and sexual interactions we had had I was starting to get excited just by the sight of her.

“Morning sissy!” Emma called loudly out of the car window as she pulled up.

“Emma! Could you at least try to keep it down?!” I said, glancing around the parking lot to see if anyone had heard her.

“Oh relax, Mike, there's no one here. Now hurry up and get in. Days-a-wasting. Your lips are looking rather inviting, Mike. Have you had something done?”

“Oh, right. Mistress idea, obviously.” I replied, wondering just how noticeable they actually were.

I tossed my bag in the trunk and climbed in next to Emma, a minute later we were on the way to her house.

“So did you have anything special planned for the day or were you just planning on trying to make sure I'm as humiliated as possible.” I said, breaking the silence.

“A little of both, actually. And don't act like you don't love it, sissy. I wouldn't be teasing you so much if it wasn't so obvious how much it turns you on.” Emma replied with a smug smile, knowing she had me beat.

I was a little surprised a couple of minutes later when I noticed that Emma wasn't driving straight to her house.

“Where are we going?” I asked.

“Well we have the whole day together so I thought we may as well do a little shopping first. But don't worry, you'll be in your cute little maids outfit soon.” She replied with a smirk.

“You know that wasn't what I meant.” I replied.

A short while later we were walking through the front entrance to the mall with me having no idea where we would actually be going.

“This way, sissy, I know where we need to start.” Emma said, again far too loudly for me.

“Emma!” I hissed, quietly. “We're in public.”

“What? Ohhh, right. The sissy thing. Sorry Mike, I guess I'm just so used to you being all feminine that I forgot.”

She forgot….yeah right.

I followed Emma through the mall towards a clothes store. I recognised it as the one I had been made to visit weeks ago when I was tasked with buying my own panties. I just hoped no one would recognise me!

We headed over to the section containing ladies underwear, me following along nervously as Emma led the way.

I had to keep reassuring myself that this was normal, I was just a guy who had been dragged shopping by a Woman, nothing out of the ordinary here.

“What do you think, Mike?” Emma asked, holding up a small red thong for me to see.

“It's….nice.”


“Nice, is that all? Don't you think it's sexy?” She asked, stretching the underwear out a little so I could see the pattern. Something about watching Emma displaying panties to me in public like it was totally normal was starting to get a reaction out of my caged clitty (What didn't get a reaction these days?).

“Yeah, I guess they would look pretty sexy.” I replied.

“Ah I think I get it, you probably prefer something a little more girly than just a thong. How about these?” Emma followed this up by displaying a different pair of underwear, these ones were more substantial than the thong, being a full cut brief style panty that had a floral pattern stitched into the lacy material. They were still revealing, but they looked like they would accentuate the ass of the wearer in a way that I found appealing.

“Yeah I think they're much better.” I said, obviously more into these than the previous pair.

What Emma did next was equal parts surprising and humiliating.

Before I knew what her intentions were, she stretched the panties out and held them right against my crotch as though measuring the fit!

“Emma! What the fuck?” I said, quickly pushing her hand away as my face turned red at the insinuation made by her measuring the panties against me.

“What's the matter, Mike? Ohhh, did you think these were for me? Such a ditzy sissy, I already have enough panties. I'm here to treat my favorite girl to a few new things.” Emma explained with a devious smile before continuing. “Now don't make a scene, you need to behave today, remember. You know what's at stake.”

She was of course referring to the fact that without her I had no chance of being released from chastity today. I glanced around to make sure that no one could see us as Emma held the panties against my crotch once more. My dick gave another twitch in its cage as she did, my arousal fuelled by the humiliation of being measured for panties in public.

I stood there as Emma repeated the process for another couple of pairs of panties, making sure to ask for my thoughts on them as she did. I weathered the humiliation as quietly as I could, hoping to not draw attention to myself. That was until two women, a little younger than Emma, came around the corner and moved close to the rack we were currently occupying….Right as Emma was holding another pair of panties to my waist.

“Okay I think that’s enough.” I said quickly, pushing the latest panties away with my hand.

“Hmm, I guess you’re right, we do have enough panties for now. Let’s move on, we need to find you a couple of bras to match.” Emma replied, making sure to finish her sentence loud enough for the two women to hear. She turned away quickly and began walking further into the store with me trailing bashfully behind her, avoiding the gaze of the two shoppers who were giving me a confused look as I passed.

“Was that necessary?” I asked as we moved towards a rack filled with bras.

“No, but it’s amusing seeing your reaction. You get so embarrassed!” Emma chuckled as she began rifling through the bras on display. “So, what cup size should we get you?”

“I don’t know, I don’t usually wear bras!” I replied without actually considering.

“Really? Because from what I can tell you’ve been wearing one everyday for over a week.”

“Well…Yeah I mean, I guess I have but, you know why that is.” I replied in a quiet voice, not wanting anyone to overhear our conversation. Unfortunately, Emma wasn’t as interested in being discreet as I was.

“Yes, because you’re a sissy who gets turned on by girly things, obviously.” Emma replied with a satisfied smile, before quickly pressing a light pink bra to my chest to see how it would look.

“Please don’t!” I said, leaning backwards to avoid the bra.

“Oh fine! If you’re going to pout about it I guess I'll just have to guess your size.” Emma said, grabbing a selection of the underwear and dropping them into the bag. I noticed that some of the bras she had dumped in the bag were obviously a large cup size, but I didn’t want to hang around there anymore so I didn’t say anything.

Mercifully, we made it out of the clothes store without any further embarrassment, Emma even paid for the new underwear she had bought me, insisting she ‘treat her sissy’.

“Okay sissy, sorry…Mike. One more place I need to check out then we can head back to my place for a little fun.” Emma said, leading the way through the mall.

I was a little shocked by where she led me to however, but I guess I shouldn’t have been by now.

“Umm, Emma…What is it you need from here exactly?” I asked as I stared at the neon sign for the adult store I had visited weeks ago to purchase my vibrating plug.

“Oh you never know, we have the whole afternoon together, might be something fun in here to ‘spice it up’. Come on, let’s go see.” She said happily, pushing through the door and into the dimly lit store.

I made sure to stick close to Emma, trying my best to make us seem like a typical couple who were just looking to have some fun.

“So, see anything you like, sissy? Any new toys you’d like to play with?”

“Not really, I thought you would have had an idea for something when you led us here.” I replied as we moved along the shelves and displays.

“Oooh, what about this?” She said in a bright voice, “A nice leather restraint kit. Oh but I won’t need restraints to make you behave will I? Not with that cage on your little dick, haha.”

“Emma!” I hissed, hoping to quiet her down a little, but she just continued on.

“Or what about this paddle? This could come in handy for the next time I spank my sissy. Or what about this nice collar and leash? I could lead you around my house like a cute little puppy!”

The truth was, the thought of Emma using any one of these items was a huge turn on! But I was trying my best to convince her to keep her voice down.

“Hey! You two looking for anything in particular?” A woman's voice said from behind us.

We both turned around to see the girl who must run the shop smiling expectantly at us. Emma answered before I had the chance to politely dismiss her.

“Oh hi there. I’m Emma and this darling here is my little maid for the evening.” Emma said, placing one hand on my shoulder, making sure the girl was in no doubt who the ‘maid for the evening’ as. “I was just looking around to see if there was anything here that would help a sissy have fun.”

I was mortified, humiliated beyond belief as Emma happily told the shop girl about how I would be spending the evening. “Emma, I…” I intended to protest or deny Emma’s words but I was speechless as my face burned.

“Oh relax, sissy. You know we’re in a sex shop, right? And I’m sure you’re not the first sissy this nice girl has seen her life.” Emma said, dismissing any protests I might have had.

“She’s right, you know.” The girl said. “We get all types in here, no need to be embarrassed. Why don’t we take a look around and see if there’s anything you like the look of. I’m Candace by the way”

“So if it’s the whole ‘forced fem’ thing you’re into, I would recommend a chastity cage, I hear they’re great for keeping sissies in line.” Candace said as we ambled slowly among the shelves. Surely Emma wouldn’t…

“Oh no need for that, he’s already locked up tight. Isn’t that right, Mike.” She would. I had hoped Emma wouldn’t be as forthcoming about my chastity, but here I was. And what's worse, she had ended by asking me to confirm it myself!

“Umm, yeah that’s…..that’s right” I mumbled out my response, staring down at the floor, not daring to make eye contact.

“Hmm, okay…How about a collar? I’ve seen quite a few dominant partners in here buying collars for their subs. We actually have a good selection in store, and there’s one I think might be perfect.”

Is that what I was now, Emma’s sub? I had to give my head a shake as the thought seemed to take hold and my clitty started to stir again.

“Well I did just see a nice collar and leash back there.” Emma said, looking back the way we came.

“Oh no I’m not talking about those flimsy pet play collars, I mean like a lockable collar, something that really symbolises ownership.” Candace said, quickly walking over to a display and grabbing one of the collars she had mentioned.

Ownership….Did I want to be owned by Emma? A certain part of me seemed to like the idea at least.

Candace returned with the collar a few moments later, holding it up for Emma to inspect. “So as you can see this one is pink, but it does come in other colours if you’d prefer. It’s about three inches thick so not easily hidden, and I can have any lettering you want added to the front at no extra charge. And it comes with a padlock and lockable buckle included.”

“I think that will be perfect!” Emma said excitedly, before adding. “Can we have the word ‘Sissy’ printed onto the front?”

“Of course. There’s a machine in the back that does the prints, five letters shouldn’t take too long. Anything else? We have a pretty good strap-on collection if you’re into that.”

“Oooh it can’t hurt to take a look, maybe he’ll get lucky tonight.” Emma replied, winking in my direction as she followed the assistant towards a small shelf that was lined with dildos of various shapes and sizes.

My eyes shot to the widest they had ever been thanks to Emma's reaction to the strap-on. Did she actually want to fuck me like that? More importantly, did I want her to fuck me like that?

“So all these on this shelf work fine with the harnesses we have in stock. Any of em catch your eye?”

“Hmm, what do you think, sissy?” Emma said, turning to see the look of absolute shock on my face.

“Umm….I don’t know I…I never, I mean, I’ve never tried.” My heart was pounding as I stumbled through a sentence.

“Oh so is he a virgin back there?” Candace asked, clearly not as worried as I was about talking about this subject.

“Well not completely, he does have a little vibrating plug that he likes to stick up there from time to time.” Emma replied to Candace, sending another wave of humiliation laced arousal through me.

“Oh so he’s familiar with some anal insertion. In that case, I would recommend this one.” Candace said, lifting up a pink dildo from the display. “So this one is around six inches long, which is a little longer than most plugs but it’s not super thick so it won’t hurt too much going in, and the way the end tapers a little should help reach that special spot. I’m told it’s quite the feeling.” She finished her explanation with a coy smile in my direction.

“Ah what the hell, better to have it and not need it than to need it not have it, right?” Emma said, agreeing to the purchase of a strap-on and harness. Just what the hell was I in for tonight?

We waited for a couple of minutes while Candace the shop girl disappeared to print the collar. Emma paid for the new things and we left the store, finally heading back to hers.

“You two have fun.” Candace said with a cute smile as we left.

A short drive later and we were back at Emma’s place, she had made sure I was the one carrying the bags through the mall as we exited.


“Don’t worry sissy, we don’t have to use the strap-on tonight. Although I’m pretty sure you’d love it.” Emma said with a giggle as she took the bags from me. I followed her to the spare room after she had told me it was finally time to ‘get to work’. I changed into the maid outfit in the spare room as Emma took the bags into her bedroom, when I was dressed and ready with my heels locked in place on my feet, I headed out onto the landing.

“Ohh, what’s this?!” I heard Emma's surprised voice come from her room, the door was open so stepped into the doorway to see what she had found.

“What is it?”

“I think Candace left us a little extra surprise in the bag. Take a look at these.” Emma said, holding up what appeared, at first glance, to be just another pair of panties. As Emma stretched them open and turned them around however, I saw that these were no ordinary panties. They were made of an almost translucent black material, frilly and lined with lace. But the back of them had a large heart shaped cutout that would expose almost all the wearers ass.

“There’s a little note here….’Have fun XOXO…Candace’.” Emma read out the note Candace had left with her gift. “You know, of all the panties we bought today, these might just be my favorite!”

Emma smiled a devious smile at me as she walked the couple of steps to close the gap between us. “And here’s my sissy, finally looking all girly and subservient in her little maids dress. I must say this look suits you so much better than your boring boy clothes. But I think we need to add a few things.” I assumed she was talking about the collar, I was wrong. It turned out Emma had bought something else for me through the week.

I watched as she headed towards her wardrobe and lifted out a large box. She opened it up and lifted out a mass of heavy looking, jiggling rubber…..was that a boob?!

“I thought it’s about time we finally filled out that bra of yours. I’ve seen the way you look at my chest, sissy. So I got you your own, nice and big like I know you like.” Emma stepped behind me as I stood there frozen, staring at the large fake tits laying on the bed.

Emma unzipped the dress from the back and lowered it enough to give her access to the empty bra I was currently wearing. The bra was quickly removed, leaving me topless with the dress lowered.

She followed this up by lifting one of the wobbling masses and uncapping some sort of spray bottle. She proceeded to spray all over the flat back of the breast, explaining that this was an adhesive spray designed to keep the breasts in place. I watched on as Emma held the breast in place on my chest, waiting long enough to make sure it had stuck fully, before moving on to the next one. She shook the tits a little to make sure they were stuck in place, before stepping back to see the results.

“Looking good so far, just one more thing.” She said, grabbing what looked like a tube of foundation and a makeup brush. I expected her to apply the makeup to my face, but instead she began to paint the thick, liquid foundation all around the edges of the breast forms, hiding the seams where they met my skin from view. She followed this up by spraying a little more of the glue all around the edges, making sure to blend it all together and thin out the foundation until it matched my skin tone perfectly. When she was finished, I couldn’t tell where my own skin ended and the boobs began, at least not by looking.

“Now let’s get this on you.” Emma said, grabbing a black bra she had picked up earlier….Now I know why she chose one with such a large cup size.

The bra lifted up and supported my new tits, pushing them together into what I thought was an impressive cleavage. If these things weren’t attached to me, I would have said they were a pretty nice pair of tits.

I simply stared down at myself, in shock at seeing a pair of boobs this big attached to my own body, I was snapped out of my reverie by Emma’s voice.

“Now I know you clearly like your new boobs, Mike. But we can’t have you walking around with them on display all day, it wouldn’t be decent. And there will be time for that later!” She added the last part with a wink. Emma stepped back behind me and zipped the dress back up, I noticed immediately that it was sitting far differently on me thanks to the breast forms. The front of the dress was pushed outwards, exposing a good amount of cleavage as the material of the maid’s dress was stretched tightly over the boobs.

I remained silent as Emma continued my transformation, not giving me a chance to process anything as she led me over to a makeup table, sitting me down in a chair which she had spun around so I was facing away from the mirror. “Those new lips of yours could use a little something to really help them stand out. Do you have anything you can use with them or should I pick something of my own?” She asked me.

“Oh umm, yeah I got something from the salon that did them actually.” I said, remembering the special lip plumper they had given me. Did Emma know about that? “I have it here, I don’t have much practice putting it on though.” I said, lifting the tube out of the small pocket on the apron of my outfit.

“Not to worry, sweetie. I’ll do it for you this time.” Emma took the lip gloss from me and began painting it on my lips. I could feel a faint tingling sensation as the plumping solution did its work, some sort of acid that was in there but I had forgotten the name.
Emma applied a little blush to my cheeks before painting my eyelashes with a thick mascara, was she finished?

“Just about perfect, just one more thing.” She said, answering my question.

I watched as Emma retrieved the collar we had bought earlier and moved to fasten it around my neck. I heard the click of the lock that had come with it, signalling that I was now stuck in a pink leather collar that had the word ‘Sissy’ printed on it in bold black letters.

“Perfect! Now let's take a look at the new you.” Emma took my hand and led me over to the front of her wardrobe door which had a full length mirror built into it.

I was stunned as I took in the sight of my fully feminized self. The makeup on my face was mostly subtle, but the blush and mascara was prominent enough that it softened my face. The real kicker was the lips, the formerly subtle filler was now accentuated by the bright pink gloss. They looked large and pillowy, shining as they reflected the false light in Emma's room. I almost wanted to kiss myself.

The Maids dress was being filled out and stretched tight by the false tits that were stuck there, blended perfectly with my skin by the makeup/adhesive combination. It was tough to explain what I was feeling right then as I struggled not to get turned on by my own reflection.

“Now THAT is a very sexy sissy! You should be proud of yourself, Mike. But I was wondering if you could make one more little outfit….for me?”

“Umm, yeah. I guess so. What is it?” I asked, wondering what more she could possibly change.

“Could you wear these for me?” Emma said, holding up the panties with the heart shaped cutout on the ass.

“W-why do you want me to wear those? It's not like you can see my ass under this dress anyway?”

“I know, it would just turn me on to know you had on such scandalous undies under your pretty little outfit.” The thought of me turning Emma on was definitely an appealing one. With that in mind, I slipped the white panties I usually wore with the maids outfit down my legs and stepped out, being careful not to snag them on the heels. A few moments later and I was pulling the special panties up my legs.

“Oh you little minx. It makes me so hot to know what's hiding under those frills. In fact….” Emma pulled out her phone and began typing something.

“In fact what?” I asked as she stared at her phone as though waiting for something.

“Just a sec….Oh good, it should be done. You can take off your cage now.” She said with a smile, clearly she had been texting Mistress on her partner app.

“Wait really? Already!” I said in surprise, not expecting to be freed so soon. I quickly pulled up the skirts of the dress and pulled the panties away from my body, sure enough, the little indicator light on my cage was telling me it was unlocked. I wasted no time in unhooking the cage from the ring and sliding the ring past my balls, momentarily forgetting that Emma was in the room because of how eager I was to be free.

It took all of about five seconds before I was at full mast, the first full erection I had had in days was stretching the new panties to their limit.

“Feel better?” Emma asked me when I was finished.

“Oh, umm….yeah, sorry. It's just nice to be free for a while ya know.”

“I'll bet it is. But don't get too excited, this is a show of faith because you've been a good girl so far. But you're still not allowed an orgasm without permission. Do you understand?”

“Yeah. Of course.” I said, feeling a small rush of pleasure at being called a ‘good girl’. It wasn't like I was just going to start jerking off in her house, but I could already feel that cumming by accident might not be out of the question. Every movement caused the panties to rub sensually against my now exposed clit, and with Emma's teasing presence on top, I knew I would have to be careful.

“There's a good girl.” Another shiver, this time Emma seemed to pick up on just how turned on I was.

“Oh dear, it looks like following my orders might be a little too ‘hard’ for you, sissy.” Emma punctuated the word ‘hard’ by squeezing my cock through the dress. “You don't want to get punished, do you?”

“N-no Miss Emma. Of course not, I can control myself.” I replied, my shaking at her close proximity giving me away.

“I'm not so sure about that. So I'll tell you what, if you can keep from cumming in your panties until we retire for the night, I'll let you have me any way you want, as many times as you want. My body will be a tool for your pleasure. How does that sound?” Emma was speaking in a low, seductive voice as one hand traced along the neckline of the maids outfit.

“Fuck! That sounds good to me.” I gasped in response. “But what if I fail?”

“Well I suppose it’s only fair that, should you fail and mess up your panties, then it’s only fair that I should get to take you to bed and fuck you however I want. Right? Either way you’re probably going to get laid tonight.”

“Right. That sounds….fair, I guess. Deal!” I knew what Emma would be going for when she said she could fuck me however she wanted, but the opportunity to have a woman like her pleasure me in any way I saw fit was too good not to risk it. I had already decided that I would start by having her suck me to the first orgasm, get that one out of the way, then I would be in a better position for later on.

“Oh good! We have a deal then. This should be easy for you. All you have to do is not squirt your sissy juices into your panties and you can have me any way you like. But in the meantime, I think my maid has a little work to do.” Emma had said it should be easy for me, but the smile she had on her face suggested she didn’t think I could last, which made me a little nervous, but I wasn’t going to back out now.

“Sure thing, I can’t wait til I win so I can finally get a little payback for making me go down on you at work.” I said, faking a cocky attitude, which was quite difficult to do given my current attire.

“Oooh, confidence. Now let’s get that cute butt of yours to work.”

“Yes Mistress.” I replied, immediately followed by grabbing the side of my dress and dipping into an almost automatic curtsy….Shit! Did I mean to do that…?

End chapter 11