Digital Dominatrix 2.0 chapter 3 (Patreon)

Digital Dominatrix 2.0 - Chapter 3.


'Sissies should be caged'

My sleep was once again a little fitful on Friday night. Tossing and turning, occasionally opening my eyes and hearing the same low female voice a couple of times through the night, but I was only half conscious so I couldn't be sure if it was real or a dream.

I decided to ignore the morning erection today, opting instead to just get dressed in my normal male clothes, and just have a chill Saturday without any fetishes or kinks dominating my day for a change. Of course, Mistress would have something to say about that, though, wouldn't she?

"Good morning slave." The AI voice spoke as soon as I had finished getting dressed. I decided on a typical chill out outfit for today, boxers underneath loose-fitting shorts with a baggy hoody, a perfect Saturday morning fit.

"Good morning, Mistress." I replied, heading out of my bedroom and into the living area of my apartment.

"You should be receiving a delivery today, slave. A package containing your new, keyless entry, wireless, and NFC compatible door locking mechanism and doorbell camera is expected around midday. Please make sure you are home to receive it."

I hadn't even looked at how much the new 'home security' stuff had cost. I was scared to know just how much of my money Mistress was spending. I had already decided I wasn't going to go anywhere special, and I never really had plans anyway, so waiting for the delivery didn't bother me. The thought of Mistress having control over the locks on my doors, though....that did bother me.

I spent the morning enjoying a little gaming and cereal. I was actually uninterrupted until around 11:30, when Mistress' voice played out through the living room speaker.

"Online tracking indicates that your delivery driver is in your building."

Guess that was my cue to turn off the games and get ready for a little DIY. I assumed Mistress would want the new locks fitted as soon as possible, so I went in search of what tools I had in my apartment and waited for the delivery.

Fast forward a couple of hours, and I was just finishing up the installation of the smart-lock system. It was a pretty good setup to be fair, I guess AI has good taste in tech.

There were two plain black NFC panels, one for inside, one for outside the door. The locking mechanism was a simple deadbolt that slid into place magnetically when it was locked and would spring back into place to unlock the door when not active.

The door could be unlocked by holding my phone against one of the NFC readers or by manually unlocking it using the app. The camera was a simple, fixed keyhole camera just above the outside NFC panel. I briefly wondered if I was even allowed to have this installed, but it was too late for that now.

"All done, Mistress." I said as I finished up, pretty proud of the job I had done.

"Excellent. I have already installed the companion app on your phone and can now freely restrict entry or grant access."

Great, I thought to myself.

"Now, slave. Don't forget, you have a task to complete before the day is over."

"Do I? What task is that?" I asked, wondering if I'd forgotten an order.

"Last night, you told me that you wished to get rid of all your male underwear. I will make sure you follow through on your request."

Shit! I was crazy horny when I had said that, I didn't think she would actually hold me to it, I thought it was just a part of the humiliation game she was playing at the time.

"W-what? Mistress, I can't just get rid of all my male underwear! I'm gonna need them again at some point." I said, incredulous.

"Let me remind you what you said last night." Mistress said before playing a recording of my own voice.

“Yes! Yes, I would like to get rid of all of my male underwear.”

The recording played loud and clearly through the speakers. You could hear the desperation in my voice as I spoke.

“Yes Mistress. I’ll throw out all my male underwear tomorrow and only wear panties from now on-" Another sound bite played out before I could answer.

"You asked for this, slave. I am merely giving you what you asked for. Now, please gather up all your male underwear and place them in a bag before taking them to the trash."

Fuck! I was actually going to have to go through with this. There was no point in arguing with her, not with all the blackmail material she now had. So, with that in mind, I gathered up every pair of boxer shorts in my apartment, including the ones that were in the wash.

I was standing in the living room with a black trash bag that contained all my male underwear, nervous at the implication of what I was about to do.

"Don't forget the pair you are currently wearing, slave." Mistress said as I prepared for what I had to do. "Make sure you replace them with panties before you take the bag out to the trash."

Fuck. I thought she might now have known about that pair. Clearly, she was watching me dress this morning.

I quickly swapped out the boxers I had on for a pair of lace trimmed hipsters that sat low enough at my waist to stay hidden in the shorts.

There is no point delaying any further. I headed out with the plastic bag, making my way down and around to the dumpster area just outside. Was I actually doing this? Was I actually throwing away my men's underwear because of a damn AI program I downloaded? I took a deep breath to steady myself, wondering if I would ever get to wear normal underwear again, and tossed the bag into a dumpster before heading back to my apartment.

Once I was back outside my apartment door, I encountered my first problem. When I raised my phone to the NFC panel to unlock the door, nothing happened. At least at first, after a few swipes of my phone on the panel, I got a notification from my phone.

'Slave, if you would like me to unlock the door, please present your panties to the doorbell camera. You are no longer permitted to wear male underwear in the apartment.' Fuck! Was she serious? I knew those locks could only spell trouble, and now I had to expose my panties in the hallway!

I knew from the positioning of the camera that I would have to step back a little before my crotch area was in view, so that's what I did. Once I was sure I was in position, I gave a quick glance up and down the hallway to make sure no one was around. As soon as I was sure the coast was clear, I quickly lowered the front of my shorts so the panties were in view.

I felt very exposed, standing there with my panties in view and a semi erect cock trying to get out. After a few seconds, I heard a click, indicating that the door had just unlocked itself. At the same time however, I heard a click behind me and felt someone walk straight into the back of me.


As I was waiting for Mistress to let me into my apartment, Kate was just exiting hers, and walking straight into the back of me.

“Oh Mike! Sorry. Why are you hovering outside my apartment? Did you need something?” Kate asked.

“Oh err, no. I was just…testing out my new door lock. Got one of those electronic lock thingies installed.”

“Oh nice, very Hi-tech. Listen, I’ve been meaning to catch up with you this week but been a little busy you know. You free again tonight?” She asked, there was a hint that she was leaving something unsaid as she spoke.

“Aren’t I always free? Text me when you’re free.” I replied.

“Sure thing, talk later Mike. Bye!” She said before quickly walking away down the hall. With that somewhat awkward exchange out of the way, I was finally free to get back into my apartment.

“Welcome back, slave. I’m sure you’ll be much happier now you don’t have any male underwear to distract you from your sissy lifestyle.” The AI Mistress said. I wasn’t thrilled about the comment about my new sissy lifestyle.

I whiled away the rest of the day without much more distraction from Mistress. I was a little nervous about seeing Kate again tonight, it felt like I might just be setting myself up for more humiliation by getting close to her while Mistress still had this much control over me, but I couldn’t pass up the opportunity either way, not after last week.



Kate text me later on Saturday night saying she was free, I assumed she would be in her ‘comfies’ so I stayed dressed in the shorts, with the panties of course. I had pretty much adjusted to my smooth legs by now, so I didn’t give a second thought to going over there with my legs bare.

“Oh hey Mike, thanks for coming. I made us both a drink already.” Kate greeted me as I entered her apartment.

“Thanks!” I said, “So is everything okay with you? You seemed a little ‘off’ earlier. Are we still…ya know, are we good?” I asked.

“Of course we are. But I wanted to ask you the same thing. Is everything okay with you Mike?” Kate asked me, eyeing me up a little suspiciously.

“What do you mean?”

“Well it’s just…I didn’t want to say anything in case you were embarrassed but…I saw you the other night. When you came home dressed like….ya know.”

Shit! I was afraid of this. She was of course referring to the maids outfit I was forced to run through the hallway in after spending the evening serving Emma after work.

“I mean, I’ve already seen you in panties and stockings but the outfit really caught me off guard. And your legs are hairless, plus the nails and everything. I guess I was just wondering what it is that’s going on.” Kate finished, waiting for me to answer. I wasn’t sure how much I wanted her to know, but I kind of figured I would have to tell her something.

“Okay, I’m a little embarrassed by it…well. Very Embarrassed actually. I didn’t really intend for anyone to find out but, I guess I let it get a little out of hand.”

“What do you mean? What is it Mike?” Kate asked, her eyes were burning into me as she waited for her answer.

“Well…it’s kind of a fetish of mine.” I started, avoiding looking at her. “I guess I kind of like the whole, humiliation aspect of wearing uh, girly stuff, could call it a kink I suppose.” I knew I would have to come clean about what had gotten me into this awkward situation, there was no way she would believe anything else after what she had already seen. “Look, I know it’s weird, and I get it if you don’t want anything to do with all…this.” I let my voice trail off as I waited for Kate to say something.

“So it’s just a kink? A fetish thing? You get turned on by being humiliated and wearing womens clothes around, is that it?” She asked, at least she hadn’t kicked me straight out.

“Yeah, that’s it.” Was all I could say. What happened next surprised me a little. I expected her to be freaked out and ask me to leave, instead she broke out into a smile.

“Well if that’s all it is, then that’s great!” She said, still smiling at me.

“Really? You think it’s great? Cos I’ve been terrified of anyone finding out this sort of stuff turns me on!” I said.

“Mike, it's 2025! I don’t kink shame. If you get turned on by wearing panties then that’s okay. I’m just glad you trusted me enough to tell me. And don’t worry, your sexy secret is safe with me!”

I couldn’t believe how well Kate was taking this.

“Well…thanks. For not freaking out that is. I just hope we can keep hanging out like we do.”

“Oh Mike, You can’t get rid of me that easily. So tell me…are you wearing panties right now?”

No point lying about it now, I thought.

“Erm, yeah I guess I am actually.” I admitted.

“Haha, I knew it! Shame on you for using me to indulge in your fantasies like that. Sneaking your girly underwear into my apartment. I wonder how many times we’ve hung out while you were secretly wearing panties.”

“It wasn't every time!” I said, realizing afterwards how lame that must have sounded.

“Either way, you owe me. So, lose the shorts!”

"What? No way!" I said, it seemed Kate was back to her playful tease approach.

"Yes way. You sneak around here in your panties all the time, secretly getting your rocks off while I was none the wiser. So now it's time for you to make it up to me. Lemme see those panties." Kate said, approaching me with a grin.

I started to back away from her as she reached towards my shorts, but I only got as far as the sofa. As I backed up I felt the backs of my legs hit the bottom of the sofa, causing me to lose my balance. Kate pounced on the opportunity, almost literally.

As I tried to keep my balance, Kate lunged forward and made a grab for my waistband, causing me to fall backwards, butt first onto the sofa. By the time my ass hit the cushion, the panties were exposed, the baggy shorts making it all too easy for Kate to yank them down. By the time I looked up at Kate's smiling face, she had my shorts off and could clearly see the panties, complete with erect cock trying to make itself known.

I suddenly felt very exposed as I was sat down on the sofa, looking up at Kate who was stood over me, so I brought my hands to my crotch, hiding it from view as my face reddened.

"Oh so now you're shy? You didn't seem so shy last week when you were fucking me while wearing stockings!" She said, catching me off guard with her brazen comment. I couldn't really argue with her though.

"Yeah, well. That was different. It's still a little embarrassing to sit here in panties with a...you know."

"With a hardon you mean?"

"Yeah, that."

"Haha, good! You can stay that way for a while as punishment for not coming clean sooner." Kate said, disappearing from view with my shorts in her hand. "I do have a nice skirt that might fit you though if you'd prefer." She added with a laugh.

Looks like I was stuck in the panties for a while, there was no way I was going to let her put me in a skirt! At least not straight away.


Once my shorts were safely hidden away, we settled onto the couch to watch a movie. Kate made sure not to let me forget about the panties though, every now and again she would make some comment to draw attention to them. Failing that, she would occasionally 'accidentally' make contact with my pantied crotch. Needless to say, by the time the movie had finished, I was desperately horny.

"Whoops! Sorry Mike. Didn't mean to touch your panties. Hehehe." Kate said as she reached across me to grab her drink, a drink she refused to put down somewhere closer to her.

"Yeah right! Could you please stop doing that? Any longer and I might just.." I stopped myself from finishing the sentence, it would be pretty embarrassing to tell a girl I liked how close I was to jizzing in a pair of panties.

"Might just what, Mike? Might just blow your load in your panties, is that what you were gonna say?" She said, sliding closer to me on the couch, letting one of her hands trail slowly up my still smooth thigh.

"Yeah....something like that." I replied, as my heart rate started speeding up in time with her hand moving towards the panties.

"Wow, I don't think I've ever felt a cock this hard before! Who knew a pair of panties would turn you on this much." She said, as her hand started to caress my shaft through the thin underwear.

"Well I think you're having something to do with that." I replied.

It looked like she was contemplating saying something else, but instead she just kissed me, hard.


Somehow, during our makeout session, we had ended up in Kate's bedroom, both of us stripped down to our underwear. Kate hadn't let up her fondling of my erection through the panties the whole time, I could feel how close I was to cumming, so I needed a plan to avoid embarrassing myself. So instead of diving straight into it, I opted for a different approach.

With Kate on her back on the bed, I slowly kissed my way down her body until my face was level with her own panty covered crotch. I soon got the panties out of the way and was left staring at her now bare crotch. Knowing there was no way I would be able to last long in my current state if we had sex normally, I decided to put my tongue to work.

Kate made no move to stop me as I eagerly licked at her pussy, before long I could tell she was getting into it.

"Mmmm that's good Mike. I love this kinky side of you." She said, her voice turning a little breathy as she enjoyed my work.

"Oohhh yeah, that's it. That's a good little pantyboy!" Fuck! Kate was starting to get a little too into it, her words doing a hell of a job at keeping me close to the edge as the panties rubbed my crotch, I could barely keep myself from grinding my crotch into the mattress.

"Mmm...fuck!" I felt Kate's hands grab my head as I licked away, applying a little pressure to encourage me to lick harder at her, which I was happy to do. "Ohhh fuck. Lick me pantyboy! Yes." Damn, she was more into this than I expected.

"Ohhhh...fuck!" Kate moaned out loud as she came hard, her body shuddering as I felt her thighs clamp down on the sides of my head.

She eventually released me from her crotch, allowing me to wipe my face and slide up to lay alongside her.

"Wow. Sorry about the whole pantyboy thing." Kate said, still a little breathless.

"Oh it's fine." I replied.

"...Does it turn you on?" She asked with an inquisitive look. I wasn't sure how to answer that one, so I just snorted in derision.

"I'll take that as a yes!" She said, smiling. "Now, I was planning on returning the favour, but seeing as you like your panties so much, how about I just do this..." Kate rolled over so she was now mounting me, straddling my thighs with hers. I could feel the heat of her pussy pressed against my erection, her juices soaking into the material of the panties. As she leaned down to kiss me, she started slowly gyrating her hips, causing her to add stimulation to my already overstimulated cock.

I quickly realized where she was going with this. Her plan was to effectively make me jizz in my panties while she humped me! The thought of me cumming in this manner was a little embarrassing for obvious reasons, but Kate seemed to be into it, so I didn't even think to object.

"Does that feel good Mike?" She asked, leaning back to talk to me, she looked incredibly powerful from my position beneath her, her hips still slowly sliding back and forth on my crotch.

"Well....does it?" She clearly already knew the answer, but obviously wanted me to say it anyway.


"Yes." Was all I could say in response.

"Mmm, I'll bet it does. I'll bet you love jizzing in your panties don't you?"

The stimulation was too much, I knew I was seconds away from cumming.

"Yes!" The words came without me even thinking about it, I was again too horny to consider the implications of my words.

"Yeah, that's it, pantyboy. Cum for me!" Kate said as she picked up the pace of her grinding across the panties, the front of which was already wet with Kate's juices, and about to get a lot wetter.

I moaned aloud as I finally came, completely ruining the front of the panties I was wearing. I was hoping to have sex with Kate again when she invited me over....did this count?

I didn't care about the answer much, I was too busy enjoying the afterglow of an amazing orgasm, humped into cumming without even taking my dick out of the feminine underwear.

After finally gathering up the courage to look Kate in the eyes again, I was glad to see she was at least smiling, clearly pleased with the results.

"Damn, you really soaked those panties of yours huh?" She said, climbing off of me and assessing the damage she had done.

"Yeah I guess so. That was....new." Was all I could think to say.

"But good right? I could see how much you liked it."

"Yeah, I definitely liked it."

"Glad to hear it, pantyboy!" She said, giggling at her own words. "But I have to be out early in the morning, so as much as I'd like to keep teasing you, I'm afraid you'll have to go." I was a little disappointed to hear that, but at least Kate and I were still good.

"Oh but you can't go home like that!" She said, suddenly springing out of the bed. "You'll need some clean panties to leave in...it's the least I can do." Kate had moved over to open one of her drawers as she spoke, fishing through and pulling out a pair of her own underwear. A bright red pair of lacy, French cut panties.

"Here you go Mike, put these on!" She said, dangling the panties in front of me. Was she actually going to send me home in a pair of her panties?

"Come on pantyboy. I wanna see you leave here in a pair of my panties."

I eventually smiled back at her, deciding to let her have her fun. I reached out to take her panties before removing my own ruined pair.

A short while later, I was standing in front of Kate, wearing the panties she had given me, I could feel them squeezing me tightly and riding up my ass, exposing a good portion of my cheeks.

"They look good on you. Now give me a twirl, I need to see how your butt looks." Kate said, eyeing the panties.

"C'mon Kate, haven't you embarrassed me enough for one night?" I said.

"Hmm, maybe. But now I know you love it, so don't expect me to stop having fun anytime soon. Now turn around and let me see that ass."

"Ugh. Fine." I gave in and turned around slowly, letting Kate take in the sight of my pantied ass.

'Slap!'

I felt a stinging slap on my butt as Kate gave me a single, hard spank on one of my cheeks.

"Looking good panty boy!" Kate's willingness to acknowledge and embarrass me like this already causing my previously spent cock to awaken. "I'm almost sad to see you leave, Mike."

After I had headed back towards the entrance to the apartment, I expected Kate to appear with my shorts in her hand. Unfortunately, when she followed me out, all she had was my phone.

"Here's your phone Mike. See ya." She said with a mischievous smile.

"Ummm Kate, my shorts. I can't be seen like this!" I said, gesturing to my pantied crotch.

"Well I'm afraid you're gonna have to....cos you're not getting your shorts back tonight. I wanna see you cross the hall in your panties! Now get going." She said, pointing to the door.

Fuck! Looks like I was once again about to risk exposing myself to anyone who may be out in the hall. Fortunately, it was pretty late so I hoped no one would see me.

"You're gonna get me into trouble, you know that?" I said, putting one hand on the handle to her door.

"Yeah but you love it!" She replied, clearly noticing the beginnings of an erection in the panties.

I carefully opened Kate's door and peeked my head out, looking up and down the hall to make sure the coast was clear. Thankfully I saw no one, which was good, because Kate chose that moment to give me a hard shove right out of the door. I stumbled the few paces into the hallway, looking back at Kate who was now laughing at me, standing in the hallway in a hoody with nothing covering my bare legs.

I quickly held my phone up to the NFC reader, and of course, nothing happened straight away.

"What's wrong Mike? Better hope you're not locked out here all night in your panties."

Just then, my phone pinged with a notification from Mistress.

'Panty check successful.' She was clearly using the new camera to make sure I was wearing feminine underwear before I was allowed entry. Thankfully, the lock clicked and I was able to enter my apartment.

"See ya later pantyboy." Kate said as she closed her own door.

"I hope you had fun with your friend, sissy." Mistress' voice said, "But you should get some sleep, I have scheduled you for an appointment for tomorrow, and you will need to make sure you are on time."

Great! I thought as I made my way to the bedroom, wondering just what tomorrow's appointment would be.

End chapter 3