Digital Dominatrix 2.0 - Chapter 2 (Patreon)

Digital Dominatrix 2.0 - Chapter 2


As promised, Emma bought me lunch on Friday from the small cafe near our office. And, as expected, the whole thing was a torturous affair for me. She had already proved how easily she could wear down my defences with her teasing and tormenting. It seemed everything she said lately was laced with some sort of innuendo, her words and movements all serving to keep reminding me of my predicament.

“I can’t decide if you’re more fun caged or uncaged, Mike.” She said as we ate lunch.

“Well I think you’re a pain in the ass either way.” I replied.

“Haha I’ll bet you do. But without the cage on your little penis, it’s just too easy to get you going, and it's too obvious that you like it.”

I wished she didn’t insist on referring my cock as ‘little’ but, pick your battles as they say.

“I told you, it’s a kink I have. I can’t help it, but I do feel like it’s harder, no pun intended, to focus on things when I’m constantly hard.” I admitted, figuring that I may as well talk to Emma, seeing as she was the only one who I could actually be honest with about this.

“Yes, I can see that.” Emma replied with a smirk, “Have you thought about just putting yourself back in chastity? You know, just to help you keep things under control?”

“Honestly, yeah, the thought crossed my mind a few times. But I just keep thinking about how tough it was when I was locked up so I’m not exactly in a rush to put the cage back on.” I said.

“Yeah, and I’m sure being able to play with yourself whenever you like has nothing to do with it.” She said, sarcasm in her voice. “I’ll bet your poor little prick is being abused like nobody's business right now.”

My face flushed red at her latest comment, afraid to admit just how right she was. Was chastity really the best option for me? Was I seriously considering willingly putting myself back in my cage?

“I have it under control thank you.”

“Oh really? Because a while ago you were at your desk about to shoot your load into your panties if I’d let you. But hey, as long as your little cock is free from its cage, I get to keep having fun.” She said with a wicked glint in her eye as her foot rubbed against my calf under the table.

I allowed myself to enjoy the feeling of Emma's foot slowly rubbing up and down my calf for a few moments before steeling myself.

“We should get back to work.” I said, quickly standing up and making to leave, for some reason, this caused Emma to giggle a little.

“Haha, you’re right Mike, but I think you should give it a few minutes.” She said, staring at the tent my cock was trying to make in the feminine pants once again.

“Shit!” I said, sitting back down to hide my erection from view.

“Hahaha, I’ll see you at work. Sissy.” She said, standing up to leave with a seductive glance at me as she turned away. I couldn’t help but watch her ass swaying as she left, which didn’t help my situation.

I had to wait a few minutes, forcing myself to concentrate on work until my cock softened enough for me to leave without incident.


By the time I got home on Friday, I had decided that I would probably have to find a way to lock myself back in the cage before Monday's shift. If anything, it would give me a little defense against Emma's constant teasing. I would just have to make sure I enjoyed my freedom as much as possible over the weekend.

As I made the short walk back home I noticed the sign for a special offer on a meal from a fast food place I liked. I figured, seeing as it was Friday, why not treat myself. I went inside to queue up for my meal, paying via the pay app on my phone, as was becoming the norm these days.

I walked slowly the rest of the way home, munching away on foot-long sandwich, enjoying the fact that it was Friday and I didn’t have to work tomorrow.


“Hello Mistress.” I said, announcing my return home after my sandwich powered walk.

“Welcome home slave. You are late home from work.” The AI voice stated in her emotionless tone.

“Late home? Sorry Mistress but I didn’t think I had a curfew. I stopped off for a sandwich on the way, that’s all.” I replied, a little annoyed at Mistress ' statement. Since when did she care about what time I got home from work?

“Yes I can see that. You purchased a foot long sandwich for $9.98 at a restaurant located on East 56th. You should have travelled straight home from work and checked in with me, as you have been doing for the past 10 business days.”

“Well, I usually just come straight home but today I felt like grabbing a sandwich. I didn’t think it would be an issue!” I was visibly annoyed now, had Mistress been a real person, and not an AI, she would have noticed me getting angry at her questioning.

“-Order Processed-”

“What the hell are you ordering this time?” I asked as I heard the notification go off. I quickly pulled out my phone to take a look at what was on my recent orders list as Mistress answered the question.

“I have purchased something that will help avoid this issue in the future.”

The ‘something’ turned out to be a digital locking mechanism for my apartment door. Apparently this would replace the basic lock that was already fitted, and could be controlled via my phone. The new lock came with a doorbell camera that was designed to trigger a short recording whenever it detected motion. I knew a few people who had these but I never saw the point with me being in an apartment building.

“Mistress, you have to be careful about how much of my money you’re spending. These things aren’t cheap!” I said.

“Do not worry slave, I am programmed to make sure you have sufficient funds to support your lifestyle, so I will use whatever additional funds I deem necessary to further enjoy your fantasies.”


There was no point in arguing with her, so I just sighed and let it go, hoping this program wasn’t going to leave me broke.

After having a few hours to myself to chill out, Mistress spoke up once more.

“Slave, please retrieve the electronic handcuffs and insert your plug. You will then present yourself to your bedroom camera wearing a pair of panties and a bra of your choice. I have detected a pair of bluetooth earphones registered to you, I would like you to make sure they are inserted into your ears. You have 10 minutes.”

Well, it looked like I was in for a ‘fun’ evening, if you could call it that. I decided not to risk being punished any further at this point so I just went ahead and followed her orders. I wondered why she had asked me to get the earbuds, given that there was a speaker in my room anyway, but I didn’t bother asking.

Less than 10 minutes later, I was standing in front of my bedroom camera in a pair of off white panties and a bra that matched. I had found both items in the bag that Emma had given me. It had taken a minute or two longer to insert the plug as I had gotten used to not having to wear it for a couple of days, but with a little extra lube it was back in place.

“Okay Mistress, I’m ready for…whatever.” I said, wondering just what she had in store for me today.

“Excellent. You will start by securing yourself to your bed with your handcuffs. You must make sure the chain of the cuffs is passed through a secure section at the top of your bed. You have 3 minutes.” I was a little taken aback by the sound of Mistress' voice being transmitted straight to my ears through the earbuds.

I guess I knew something like this was coming. I laid on my back on the bed after snapping the first cuff around one wrist. My bed didn’t have many places to secure the cuffs, so I had to slide the other cuff and chain around a small bar where the headboard section was attached to the main body of the bed. This meant that I couldn’t slide my hands up, down, or side to side. After locking my other wrist into the wirelessly controlled cuffs, I was firmly secured in place on my bed until the Mistress decided to release the cuffs. I struggled a little, just to test what mobility I had, which wasn’t much. I could only half roll over due to the chain of the handcuffs not having enough slack, as soon as I got onto my side, the metal started biting painfully into my wrists, forcing me to stay on my back. I’m sure this would make for an excellent blackmail photo, me chained to the bed in a bra and panties.

“Okay, I'm in position. Now what?” I said, a little nervous and more than a little aroused at my current predicament.

“Now it is time for a training exercise. Repeat the following statements, just as you have done in a previous session. This time, however, you will be rewarded for following along successfully.”

Was this just a way for her to get more humiliating voice lines from me to use later?

“First, repeat the following phrase. ‘I am a sissy’.”

I hated that I kept getting referred to as a sissy. I know I liked the humiliation side of femdom, but did I really like this? My cock certainly seemed to.

“I am a sissy.” I repeated the phrase back as instructed. As I finished speaking, the plug in my ass gave a small vibration.

“You can do better, slave. Again, say ‘I am a sissy’. With more enthusiasm this time.”

I sighed in defeat and repeated the phrase once more, this time a more powerful, and much longer vibration from the plug. I squirmed a little on the bed and my arousal ramped back up.

“Much better slave, your performance will be rewarded. Now, repeat the following phrase. ‘I have a big, manly, cock’.

This was not what I was expecting, but I happily went along with this phrase. “I have a big, manly, cock.” I said, not needing any more encouragement this time. I expected the plug to kick in and reward me for following orders, but what happened this time was much worse.

‘Skreeeeeeeeech!’ The earbuds let out an ear-piercing screech at what had to be max volume, pumping the high-pitched sound directly into my eardrums.

“Arrgh! FUCK. Mistress, what the hell was that?” I said much louder than I should have thanks to the after effects of the screech.

“That was a test slave. A test you failed. Now, repeat the following phrase. ‘I have a big, manly, cock’.”

“No way! Not falling for that again.” I said, not quite realizing the implications of this supposed ‘training exercise’.

“Excellent. So are you telling me that you do not have a big, manly, cock between your legs?”

“Well, no that’s not what I’m saying. I’m just not falling for that trick again.” I could tell Mistress' line of questioning was leading me either to a punishment, or to me saying what she wanted to hear.

“So answer this question, slave. What do you have between your legs?”

“Ummm, I just have a regular, normal sized dick. Average size I’m assuming.” I replied, wondering if this answer was enough to avoid the punishing scream into my ears. It wasn’t.

“Arrrgh!” I felt my face scrunch up as I gritted my teeth and tried to block out the ear-splitting screech. This one went on a little longer than the first, causing me to rub my head around on the bed, hoping to dislodge the earbuds. After what felt like an eternity, the punishment sound stopped.

Mistress, didn’t give any time to recover before speaking again this time.

“Wrong answer. Your punishments will continue until you get it right. Now, what do you have between your legs?”

I thought back to humiliating mantras from the video I had been forced to watch last night, the answer coming to me immediately.

“A little sissy clitty!” I answered as quickly as I could. This being one of the most humiliating things I could possibly say about myself, it stood to reason that my face would be burning with embarrassment at yelling it out so quickly. And of course, my cock returned to full mast, having wilted slightly during the punishment. Thankfully, my answer was clearly satisfactory, as the screeching sound was replaced by the plug springing back into life, causing me to let out a satisfied little moan.

“Correct. Now, repeat the following phrase. ‘I love being able to stroke my cock whenever I want’.”

Okay, this one had to be a trap. “I love being able to stroke my erm, clitty, whenever I want.” That sounded right. Or so I thought.

‘Screeeech!’ “Ssstop!” I yelled, the blast wasn't as loud or as long as before, but clearly I had not got the answer right this time.

“Almost correct slave. Perhaps you think about this one. Do you really like having your little clitty free to embarrass you whenever it wants? Now try again. ‘I love being able to stroke my cock whenever I want’. Repeat the phrase.”

With Mistress' words, I realized what kind of answer she was looking for.

“My clitty should be in a chastity cage.” As soon as I spoke the words I was rewarded by the plug kicking into high gear. By the time the lengthened vibration stopped, I was writhing on the bed. If my hands had been free, I knew I would have already had one of them wrapped around my cock by now.

“Good work slave, you are learning. Your next phrase is, ‘I am a man, and as a man, I prefer to wear boxer shorts’.”

I knew what she wanted, and I was getting desperate to feel the plug's vibrations again.

“I am a sissy, and as a sissy, I prefer to wear panties.” I said, not caring about the humiliating statement. I got my reward shortly after as the plug sprung back to life, pushing me closer towards orgasm in the panties. I squirmed on the bed, trying to hump my ass into the mattress to increase the plug's stimulation. By the time the vibrations stopped this time, I was a quivering, desperate mess.

“I am a grown man, I will not be punished like a child. Repeat.”

“I am a sissy, I enjoy being spanked!” I assumed that was along the lines of what Mistress was expecting. The more humiliating the better.

The ‘training’ continued in this vein for a little while. With me being pushed close to the edge of orgasm by the plug, but never close enough to actually orgasm.

“I want Mistress to allow me to wear my normal, male underwear, from time to time.”

“I want Mistress to make me wear panties from time to time.” I said, waiting for my reward.

‘Skreeeeeeeeech!’ “Fuck, fuck, fuck. Stop!” I cried as the sound once again assaulted my eardrums. I thought I had that one right, but clearly Mistress was expecting more.

“What was I supposed to say?” I asked as the ringing in my ears died down.

“A sissy should not want to wear panties from time to time to slave.” Was all she said in reply, before asking me to repeat the phrase again.

“I want Mistress to make me wear panties all the time.” I said, this time being rewarded with more pleasure from the plug.

“‘I should make sure to keep a few pairs of male underwear, just in case’. Repeat.”

“I should get rid of my male underwear altogether.” I assumed that was what she was expecting. “Ohhh yeah. Please.” I moaned as I was pushed closer and closer to orgasm by the plug. I was writhing on the bed, desperate for any additional stimulation. I had stopped caring about the humiliating phrases, I would say whatever I needed to for this teasing to stop.

Had I been in a clearer state of mind, I might have wondered about the implications of all this positive reinforcement I was undergoing right now.

“Very good slave. You are doing well. Now, I have a question for you. Would you like to get rid of all of your male underwear?”

“Yes! Yes I would like to get rid of all of my male underwear.” I answered immediately, without thinking about whether or not this was part of the game. Thankfully, I was rewarded once more as the plug pushed me back towards the edge once more.

“Very good slave. Tomorrow, we shall throw out all of your male underwear. Is this what you want.”

Was it what I wanted? I couldn’t think straight, not while I was as horny as I was. Plus I was still desperately close to cumming and would say anything to get there.

“Yes Mistress. I’ll throw out all my male underwear tomorrow and only wear panties from now on. Just please let me cum!” I begged, still squirming on the bed.

“Only good sissies get to cum. Are you a good sissy? Should I let you ejaculate? Right out of your big, hard cock and into your panties. Is that what you want, sissy?”

“Yes Mistress.” I cried as I got closer to the edge. “I want my little sissy clitty to cum into my panties.” She thought she’d catch me out with that ‘hard cock’ part. But even as horny as I was, I was still aware enough to avoid the punishment. The plug kicked into action as soon as I had finished speaking. This time, the vibrations were clearly set to the maximum as the plug assaulted my prostate without slowing down.

After a few long moments of me squirming and writhing on the bed, enjoying the sensations from my ass, I was ready to blow. Something inside me told me that the vibrations might stop at any minute, so instinct took over as I spoke up.

“Ohh yes Mistress. Please don’t stop. Please let your sissy’s clitty cum into her panties. Please!” The humiliating words left my mouth without being prompted, desperate to keep the sensation alive. “Ohhh Fuck!” I moaned out as I came, into the panties, thrusting my ass as deep into the mattress as I could to increase the sensation from the plug.

A few moments of me panting on the bed later, the plug vibrations ceased and I was left in a cum-soaked pair of panties, a little worried about where the footage or sound bites might end up.

“Well done slave. I only had to punish you four times during this session. You are free to enjoy the rest of the evening as soon as your cuffs release.”

“Thank you Mistress. Umm, when will the cuffs be released exactly?” I asked, starting to feel a little more awkward about being laid on the bed in a bra and panties, one of which was soaked in my ejaculate.

“You have 9 minutes and 36 seconds until the cuffs release. Here is something to listen to while you wait.”

For some reason, I imagined some old school elevator music playing while I waited … Of course, what I got was completely different.

A sultry female voice began speaking directly into my ear.

“You are a sissy. You love your panties. You do not have a big cock like other men do. You have a small sissy clitty that belongs in a cage. You are a sissy…..”

The voice carried on speaking through the earbuds as I waited to be unlocked. It sounded like there were multiple voices speaking, all layered over the top of each other so I didn’t catch every word that was said. But I heard enough to know that it was just more of the same sissy mantras I had been subjected to over the last couple of days.

“You are a sissy. Sissies love cock, real or fake, it doesn’t matter. A sissy is always horny, always desperate. Lock up your cock, sissy….”

I tried to ignore the words, but being tied down and having them pumped straight into my ears made it impossible to tune out the voice.

Thankfully, the 10 minutes flew by and I was able to release myself from the cuffs and remove the earbuds.

After showering myself off and putting some clothes in the wash, I was able to chill out and actually the rest of the evening. I ate some food, watched a movie, and played some games. All in all a mostly normal evening. I went to bed on Friday night feeling pretty good, even with all the added feminization.


As I drifted off to sleep, I briefly thought back to the session on the bed with Mistress, did I say I was going to throw away all my male underwear? And was she actually serious about it?


End chapter 2.