Digital Dominatrix 2.0 chapter 4 (Patreon)

Digital Dominatrix 2.0 chapter 4

This had to be a dream...I was in my maids outfit once again, and once again, I was bent over the knee of Emma, receiving a spanking. How or why I got here, I don't know. That's why I figured it had to be a dream.

Every time Emma spanked me, she would say something, something so quiet I could only just hear it. It sounded like she said....

'You are a sissy, and good sissies should be caged.'

But it couldn't have been Emma talking. The quiet voice sounded nothing like her.

'You don't have a big manly cock, you have a little sissy clitty.' There it was again, the dream Emma's weird sounding voice kept repeating humiliating mantras over and over. At some point, I opened my eyes, escaping the dream for a few moments, only to realize that it was nowhere near time for me to get up. The weird thing was, even though I was no longer dreaming, I could still hear the dream Emma's distant voice, as though it had somehow made it out of the dream and was still echoing around my bedroom....and why was the little light ring on the AI smart speaker illuminated?

I didn't have the time or energy to ponder these questions however, as I was quickly falling back into a deep sleep.

'You want to be a good sissy.'


I woke up on Sunday having had a better night's sleep than I had the last couple of nights, which I was grateful for. I only had vague recollections of the dream I had last night, I do remember it had been hot though! My cock was once again begging for attention as I sat up to get out of bed. I had been extra horny lately, and knew that I would need to find a way to hide it if I was going to make it through another week at work. Besides, sissies should be caged anyway.

Where the hell did that last thought come from? I asked myself as the idea seemed to come totally unbidden.

After I had dragged myself out of bed, I looked down at my body, only to realize that the panties I had woken up in were not mine...I had slept in Kate's underwear, and what's more, she had given them to me herself.

The realization brought on a new wave of arousal and I had to stop myself from reaching down to play with myself...there would be time for that later.

"Good morning Mistress." I said as I entered the living area, hiding Kate's panties from view under some baggy gray pants.

"Good morning, sissy. I hope you slept well. You have an appointment scheduled today for 11:30am. I will send the location to your phone's GPS app nearer the time." Mistress' voice came cold and unemotional as ever from the speaker.

Well, at least I had an hour or so before I needed to go out, that was something. I whiled away the morning not doing much, just enjoying the fact that I could actually chill out for a while and enjoy a little gaming time.

At some point nearer the time of my appointment, Mistress' voice came from the living room speaker.

"Sissy, it is almost time for your appointment. The location has been pinned into your GPS app. You must make sure you are wearing thong underwear and a bra before you leave. Please make sure to present confirmation of your underwear before you leave."

This had me a little nervous, why the hell did I need a thong and bra for this appointment? But I knew I couldn't get away with not doing as I was asked, not while the cameras were all active.

So, after throwing on a blue thong and a white bra (that I found in Emma's bag), I was ready to go. I kept on the baggy gray pants and a hoodie, hoping the loose nature of the clothing would hide the embarrassing underwear.

Checking my phone as I walked towards my destination, I saw that I was heading towards a row of shops that I had passed a few times before, looking for a place called 'golden touch', but I had never heard the name before so I wasn't sure they sold.


I didn't have to wonder for long however, as soon as I approached the storefront, I could tell that it was a tanning salon. I couldn't help but feel a little relieved, a tanning salon was far less embarrassing than turning up for an appointment at a beauty salon as I was forced to do last week. Men used these places all the time anyway.

I headed through the door to the front desk and gave the lady my name. She confirmed my appointment on her PC before pointing through a door.


The lady on the front desk had told me I had a spray tan booked for today in one of their automated spray tanning machines. Thankfully, I had plenty of privacy to get changed before entering the tanning-bed, which was reassuring. The problem started before I had even entered the large silver closet-like structure.

'Sissy, I can see you have arrived at your appointment. Before beginning your appointment, you must make sure NOT to remove your thong or bra.'

I was a little surprised as I read the message from Mistress, I quickly realized that this appointment might turn out to be more humiliating than I thought.

I did as I was asked and removed everything except the underwear, I grabbed up a pair of small goggles to protect my eyes and a weird sort of plastic baggy for my hair before stepping into the walk-in spray tanner....at least it was automated.

I walked into the semi-spacious interior of the silver chamber and a small, electronic sounding voice came from a small speaker as I entered.

"Hello and welcome. Please place your feet on the marked areas on the floor." I looked down and saw two footprint outlines printed in a bright neon paint. I placed my feet in line with them, sighing at the fact that I was once again being ordered around by a machine.

"Please keep your arms away from your sides, and your feet apart. The cycle will start in a moment, please remain still."

I did as I was told to by the electronic voice and waited for the spray tan to begin.

I heard a little whirring from the machine and something that sounded like pressure building up. I made sure to keep my body still as I heard a ‘pssshhh’ sound from in front of me. I felt the cool spray covering me from head to toe. Shortly after my front side was coated, I heard a similar sound coming from behind.

‘Psshhhhh’

Before long, the spray tan was finished and I heard a whirring sound from all around me as a gentle breeze circulated in the chamber all around me.

‘Bing!’ I heard a sound that I assumed signalled the end of the tanning cycle.

I stepped out of the booth and could see how the color of my skin had gotten significantly darker, almost too dark. I currently had an unnaturally brown color to my skin. I also seemed to have ruined the white bra I was wearing…whoops!

I quickly threw my clothes back on over the underwear and headed out the way I came. As I made to leave, the lady on the desk held out a small bag before saying, “Don’t forget your aftercare package dear. Instructions on what to do next are on the leaflet in the bag.”

“Oh, yeah..thanks.” I said, quickly grabbing the bag and leaving.

I felt a little weird on the walk home, having never had a spray tan before, I pulled out the leaflet from the bag I had been given and began to read it on the way home.


Apparently I had to take a warm shower and pat myself dry, rather than rub too hard with a towel. Once that was done, I had to use the moisturizer in the bag, this would help the tan last longer. I wasn’t sure if I actually wanted it to last longer, but figured I didn’t want to upset Mistress, so I resigned myself to doing as I was supposed to.

A few hours later, after being reminded of what to do by Mistress, I was just finishing patting myself dry, I was a little concerned as I watched the murky brown shower water disappear down the drain, thinking I had overdone it, but as I looked at my body in the bathroom mirror, I saw that the tan had settled into more natural bronze looking color. I had to admit, the finished product looked pretty good, except for one thing of course….Tan lines!

I had very obvious tan lines thanks to Mistress insisting that I wear the thong and bra while being tanned. I had pale white lines that ran over my shoulders that would leave no mistake as to what I was wearing while tanning, not to mention the perfect outline of the bra cups. But the worst part was definitely the whale-tail outline of the thong. Upon seeing the thongs tan line, I immediately wished I had at least pushed the waistband a little lower. The outline of the thong would sit above the waistband of most things I wore on my legs, meaning I would have to be sure not to expose my lower back to anyone.

After I was finished moisturizing, I stood in sight of the living room camera, completely naked, so that Mistress could assess the results of my appointment.

“Excellent, sissy. Your tan came out very nicely, according to most records, a spray tan can last up to a week. Please make sure not to deliberately do anything to ruin your tan.” The AI voice told me.

Great, now even if I was naked I would have a humiliating mark of my progressing sissyhood on my skin.


I managed to enjoy a little ‘me time’ for a good chunk of the rest of the day, but I was of course interrupted by Mistress, who had a ‘task’ for me. I had to wonder if she was just doing this because she was bored…could an AI get bored?

“Now sissy, I think it is time we had some fun. I want you to go into your bedroom and cuff yourself to the bed as you have done before. Make sure you are wearing panties, and have inserted your plug before you do.”

‘Sigh’ “Here we go again.” I mumbled quietly to myself as I got up and headed to the bedroom. A few minutes later, I was securely fastened to my bed once more, my newly bronzed body on display, as Mistress had not told me to wear a bra, the tan lines were clearly visible on my chest. The bluetooth controlled butt-plug was safely nestled up my ass once again and I was anticipating more teasing.

“Very good sissy. Let us start with a game you are familiar with. Repeat the following phrases. The first phrase is ‘I am a sissy’. Repeat.”

“I am a sissy.” I said, realizing it would be pointless to fight against the game again. As soon as I finished saying the humiliating words, the plug kicked into life. I was already hard from the day's events so it didn’t take much vibing of my ass to get me into the mood.

“Your next phrase is ‘I love having my sissy ass filled’. Repeat.” Fuck, was she planning on keeping these recordings for later too?

“I love having my sissy ass filled.” I said, a little nervous that she would have that recording in her memory banks.

“More enthusiasm sissy. Failure will result in punishment.”

“I love having my sissy ass filled.” I said, louder this time and with what I thought was more enthusiasm. Thankfully, the pug kicked in again, indicating that I had done a good enough job.

“I can’t wait for my Mistress to fuck me in my sissy ass. Repeat.” Shit! Did I really want her to have that one in her arsenal?

“I…can’t wait for, um, Mistress to fuck my sissy ass.” I said, way too hesitantly.

“Not good enough sissy. I warned you that failure will result in punishment. If you do not complete this phrase to my satisfaction, then I will open up a livestream from your bedroom camera on a social media account of my choosing.”

“What?! Mistress, you can’t fucking stream this!” I cried, shocked at her latest threat. Once again, I was reminded that even though I was enjoying the humiliating treatment, I was in way over my head.

“Actually I can, sissy. And I will if you do not complete this task. Now, repeat the following phrase, ‘I can’t wait for my Mistress to fuck me in my sissy ass’. Repeat.”

“I can’t wait for my Mistress to fuck me in my sissy ass!” I cried out, hoping that I had managed to make my voice sound desperate, as if that was something I really wanted..but was it?

The plug kicked into life once more, making sure to keep my cock fully hard.

I knew I couldn’t risk this being live streamed, so I made sure I would not mess up again. I simply allowed myself to get lost in the feelings of restraint and submission and just enjoy the humiliating treatment.

“Please fuck my ass Mistress”

“I love showing off my panties to everyone!”

“This sissy needs a nice big cock to suck.” That last phrase almost caused me to fail again, but I managed to save it. On and on the game went as I was forced to loudly declare my humiliated status to the smart speaker.

“I can’t wait to have huge titties to shake around.”

“I love playing with my sissy clitty.”

Eventually, Mistress informed me that the game had finished for now.

“Well done slave, you managed to avoid your session being live streamed. But you attempted to disobey me, therefore I will have to administer a small punishment. A punishment which is now on the way.”

“Wait what? What do you mean on the way?” I asked, unsure of what kind of punishment would be on the way while I was still cuffed to the headboard of my bed. I got my answer shortly after, when I heard a knock on my door.

“That knock is your neighbour, Kate. Your new doorbell camera detected her returning home a short while ago. I sent her a message requesting her help with something.”

“Seriously, she only just found out about this…kink, like, yesterday. She can't see me like this the day after!”

‘Knock knock knock!’

“Prepare yourself, sissy. I am unlocking the door now.”

I panicked as I heard the ‘click’ that signalled that the magnetic lock was disengaging, Kate could now just walk right in.

And walk in she did, I heard the door opening, followed by Kate's voice calling out from the living area, not expecting any company, I had left my bedroom door wide open. A few steps further and Kate would be able to see clearly into my bedroom.

“Mike, I got your text, is everything okay?” I considered yelling for to leave, telling her not to come any closer. But before I could do that, Mistress decided to take the initiative. I was shocked once more as I heard my own voice once again playing through the smart speaker, this time playing something I'd forgotten I had even said.

“I want to lick Kate's pussy.” There was no mistaking my voice as it played loudly through the speaker next to my bed.

“Oh you do, do you?” I heard Kates reply, immediately followed by her appearance in my bedroom doorway. I was too overwhelmed with embarrassment to even think of trying to explain my current predicament.

“....uuhh, hey Kate.” Was all I managed to say.

“Hey pantyboy, you look like you're having fun.” She replied, still eyeing me up from the doorway. Maybe it was the fact that I had been teased by the plug for the last who knows how long, but Kate looked stunning framed in the bedroom doorway like that. All she had on her legs was a tiny pair of booty shorts along with a baggy t-shirt on top.

“Yeah…uhhhh, sorry. Got a little carried away here I guess.” I said, not knowing what kind of excuse would be able to explain this situation.

“I can see that,” Kate said, walking further into the room, “Oh my god Mike did you….you have tan lines!”

I was wondering when she would notice, I guess the dim, false light of the bedroom hid the effects of the tan.

“Yeah I kinda got a spray tan.” I said, stating the obvious.

“Obviously, but you wore a bra while you did it! Hahahaha that is too fucking funny.” Kate failed to contain her laughter as she looked at the obvious tan lines on my chest, and she hadn’t even seen the others yet.

“It’s not funny!” I said as Kate continued to laugh. “I just always thought tan lines were sexy, so I just…I just wanted to see what they’d look like…..Stop laughing!”

“Hahaha, okay. I’m sorry, pantyboy. I just can’t believe you wore a bra to a spray-tan. You’re a lot kinkier than I imagined, Mike. I’m surprised.”

“Well we all have our little kinks.” I replied.

“Yeah, and you clearly enjoy yours.” Kate said, reaching out a hand to slowly stroke the prominent erection that had not stopped trying to break out of the tight panties I had on.

“So, did you text me cause you needed help getting free or…were you hoping for something else?” She asked, still slowly stroking the front of the panties.

“Umm, I don’t need help getting free, the cuffs are erm, on a timer thing. They’re electronic.”

“Well don’t you just love your gadgets. So if you’re stuck there, then I guess I can just have whatever fun I want with you, right?” She said, a different kind of look in her eye this time.

“Yeah…I guess so.” I said, wondering what sort of fun she was planning.

“Great. Because I’m pretty sure I heard you say something about licking…something, as I walked in here.” Kate had stood up from the bed, and began removing the tiny shorts she was wearing. “And seeing as you’re stuck there. I guess I’m gonna have to do this.”

After she had spoken, Kate climbed up onto the bed, one leg on either side of me as she continued crawling further and further up my body. She stopped when her knees were on opposite sides of my head and I was left staring at her bare sex just inches away from my lips. In my already insanely horny state, I was desperate to taste her again.

I got my wish a moment or two later as Kate lowered herself onto my eager lips, it took no prompting on her part for my tongue to start going to work on her.

Before long, Kate started gently rocking back and forth on my face, coating the lower half of my face with her juices. I could hear her quietly moaning as she enjoyed her position atop me, I would have been moaning myself if my mouth wasn’t so busy. Needless to say, I was loving this!

After a few minutes of my tongue work, Kates grinding on my face became a little faster and harder. I could feel more of her weight pressing my head into the mattress as she rode my head.

“Ohh yes. Fuck. That’s it Mike.” Not long after, she began to aggressively rub her pussy across my lips, pushing herself closer to orgasm.

“Oh fuck, fuck. Yes!” I was now barely licking at her at this point, instead just holding my tongue upright as Kate took over and used my face for her pleasure. “Ohhhhh….”


Kate worked herself to orgasm and finally slowed down her riding, allowing me to slowly lick her as she came down from the high.

“Mmmm that was great Mike. I’m glad you texted me.” She said, as she climbed off the bed and bent over to pick up her shorts. “But I guess I’d better leave you to the rest of your….’fun’.”

“Wait you mean…you’re gonna leave me like, Like this?” I asked, gesturing with my head towards my desperate cock.

“Fraid so, Mike. The cuffs are on a timer right? Wouldn’t wanna spoil your fun. Later dude.” She said, turning to leave and giving me a great view of her ass in the shorts as she walked away. Fuck! I didn’t think I had ever been as desperate for someone to touch me before.

“Mistress! Please,” I started begging as soon as I heard the door close, indicating that Kate had indeed left me like this. “Please let my hands loose. I need to cum so bad!”

“Would you like to masturbate sissy?” Mistress said in response.

“Yes. Yes I would. Please!”

“Very well, I will release the cuffs shortly. When you are free, you will move to your laptop and I will load up a suitable video for you to masturbate to. Make sure you follow the instructions on the video closely.”

I should have seen something like this coming after the last time I had told Mistress I wanted to masturbate, but I didn’t care about that right now. I just needed to get off.

A minute or two later, I was back in front of my laptop screen, watching a sort of guided masturbation/JOI video featuring a strict looking woman in a tight skirt. As I watched the video the woman on screen would tell me how fast to stroke, telling me to speed up until I was close to the edge before slowing down to keep myself there. The whole time I watched the video, another sound was playing from the smart speaker behind me near the bed. I could just hear the repeated sissy mantras playing on a loop behind me as I pleasured myself.


Finally, the video reached its end and I was given permission to cum. Just as I was about to blow my load into the panties, I heard the smart speaker behind grow louder so I could make out the words ‘sissies cum in panties’.

“Sissies cum in panties!” I don’t know why I repeated the phrase, I hadn’t even been told to. I guess after the ‘games’ Mistress liked to play, I had come to associate pleasure with saying those humiliating phrases. I came hard into the panties, soaking them through and messing up yet another pair. I was going to need to do some washing very soon or I would run out of underwear…god knows I didn’t have any boxers left to wear!

I was finally spent after my orgasm and decided it was time to go to bed. I set my alarm a little earlier than usual for work tomorrow, so that I would have time to wash myself properly without ruining the tan.

A while later, I was drifting off to sleep once again, this time naked. Just as my eyes were closing and my mind drifted off to sleep, somewhere between conscious and unconscious, I thought I saw the light ring of the smart speaker start to glow and a low voice start playing in the background.

‘You love being a sissy…..’



I woke up to my alarm on Monday, feeling my morning wood as prominent as ever. This only served as a reminder that I would need to do something to control my erections at work, or risk repeatedly putting myself in awkward situations.

After I had gently patted my freshly washed, and still smooth body dry, I headed into the bedroom to ask for Mistress help. Not quite believing what I was willingly about to do.

“Mistress, I was wondering if I could ask a favor?” I said, still naked from my morning shower, with one hand holding my bluetooth chastity cage, I knew there was now way to get it to lock properly without access to the app.

“What do you need, sissy?” Came the AI reply.

“I was wondering if I could wear my chastity cage….just to help…control myself at work? I keep getting distracted and, well, you know.” I said, a little embarrassed to be asking for this.

“You are not currently being punished with a chastity sentence sissy. Are you asking to enter into a voluntary chastity contract?” She asked.

“Umm, yeah. I guess so.” I said, a little worried at what I was agreeing to.

“Very well sissy. I have just downloaded a .pdf file to your phone outlining the terms and conditions of a voluntary chastity contract. Please read them carefully before giving consent.”

I picked up my phone and opened up the most recent download, and what I saw was pretty much what I expected. Pages and pages of long winded legalese in a tiny font size.

I scrolled to the bottom of the file, barely reading any of the words. As soon as I reached the bottom of the page, Mistress spoke up again.

“Now that I can see that you have read the terms and conditions. You must give your consent to enter into a voluntary chastity contract by clearly asking me for what it is you want.”

“Okay…erm, could you please lock me into chastity Mistress?” I asked.

“And why would you like to be locked in chastity, sissy?” I wasn’t expecting to be met with this question, but I realized I knew the answer anyway.

“Because I’m a sissy, and sissies should be kept in chastity.” I said, without even needing to think about the answer.

“Good answer, sissy. I am pleased that you are beginning to accept your new sissy lifestyle. Please reattach your cage and I will activate the lock.”

I did as Mistress said, squeezing the ring behind my clit-er, cock and balls and squeezing my semi erection into the cage portion. It was a little difficult to get the two pieces together due to my own arousal, but I eventually managed it.


When the cage was now back in place around my cock, I saw the tiny little LED indicating that it was once again, locked in place.

“Excellent, sissy. Your sissy clit is now back where it belongs. Thank you for voluntarily entering into chastity and finally accepting your place as a sissy.”

Is that what I had just done? Had I accepted my place as a sissy? All I really wanted was to keep my erections under control so I wasn’t constantly distracted at work.

“As you have reached the next step in your sissy training, a bra is no longer optional. You must make sure to be wearing a bra and panties each time you leave your apartment. I will check to make sure you are wearing appropriate sissy underwear before I will grant you access to your apartment from now on. Now, you had better get dressed before you are late for work.”

Fuck! In the space of one weekend, I was now stuck wearing bra and panties every day! As much fun as I had had up to now, I really needed to find a way out of this Mistress program. There was a part of me that knew that everything could go back to normal once the program was deleted and Mistress memory was wiped of all the humiliating photos, but that part of me was starting to get a lot quieter.

As I got dressed for work, I realized just how dangerous an AI Mistress was. After all, a human dominatrix would have some mercy, or at least a safe word. A human Mistress might even feel guilty if they pushed a submissive too far…but an AI Mistress, an AI had no mercy, or guilt. She was doing exactly as she was programmed to do. And whoever programmed this particular Mistress, didn’t plan on showing me any mercy!

End chapter 4.