Em Brace
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Digital Dominatrix - Final Protocol, chapter 9
🕑 Added 2025-10-11 08:03:12 +0000 UTCDigital Dominatrix - Final Protocol, chapter 9
Emma
I knew I had to give Mike enough space for the week, he was in a vulnerable spot right now and completely enamored with me and the things I could give him. But that was the problem, he was so deep in subspace at this point that he would have done anything if I pushed him hard enough, which is not what I wanted to do. I wanted him to make this decision himself.
I knew I could make him, and myself, very happy if he chose to be mine, but not if I forced him. So I kept my distance, mostly anyway, and let him straighten out his head. I was not altogether surprised by the fact that he had tried to undo some of the changes made in the last week or so. It would be good for him to try to regain some of his masculinity, it would help him realize that he prefers to be in panties.
It was hard for me to restrain from teasing him at work. I so enjoyed his reactions, seeing him squirm and blush as he got so obviously aroused by me and my teasing. But the last step needed to be his to take. Maaaaybe with a little nudge in the right direction from me of course.
I was happy to see that he lasted all of one day before he came back to work in panties, the panty lines visible beneath his pants. This was a big step, anyone who truly wanted to be done with that kind of lifestyle would simply get rid of the panties altogether. Sure he would find men's underwear a little uncomfortable for a while until he got used to them, but it would be manageable. Mike on the other hand, just jumped right back into a pair of panties……and wore them to work no less!
I couldn’t resist a little tease while he was in the breakout room that day, maybe a small demonstration of dominance, gauging his reaction. I was happy to see the desired response. His red face, the tremors in his voice and the obvious arousal.
I waited patiently for his arrival at work on Wednesday morning. He walked in shortly after myself and Jake, greeted us both in his customary way and got set up at his desk. I myself had plenty of work to be keeping busy with, so it wasn’t until I had cleared up the previous twenty four hours reports that I had a few minutes spare.
I scooted my desk chair across the bullpen and into Mike’s booth, watching as his face blushed a little as soon as my legs bumped against his, damn he was cute!
“Hello, sissy.” I greeted him in a quiet voice. I knew Jake would never be able to hear me, but the fact that I was calling him a sissy in the office was enough to provoke a small response.
“Hey, can I help you with something?” He asked, trying, and failing, to sound nonchalant.
“Actually I was just wondering what kind of panties you wore to work today?” I asked quietly. I saw how his legs squeezed together a little as he tried to suppress his arousal. I figured he would be desperate to get out of the cage by now.
“What makes you think I wore panties?” He asked.
“Because I know you, Mike. You’re obviously much happier in panties, you lasted what, one day in boxers? And I’ll bet you were back in panties as soon as you got home from work.” His downward glance and mumbled response told me all I needed to know. “Ha! I’m right, aren’t I?”
“What if you are? They’re just panties.” He replied, a little defensively.
“I know they are, and I love seeing you in them. I’m just wondering how long I have to wait to see you in panties again.”
“Not much longer I guess.” He replied, quicker than I expected.
“Oh really?” I answered equally as quickly, “So does that mean you’ve made a decision?”
“What? No…not yet at least. I guess I just….I’m not sure.” He stuttered a little as he responded, obviously he had given more away than he intended.
“Not sure about what exactly? I asked him.
“Well it’s clear you’re still caged, Mike. I know that a part of you has probably been conditioned to feel comfortable with your cock in a cage, but like I said yesterday, you could have gotten it unlocked if you really wanted. You wanna know what I think?”
“I’m sure you’re going to tell me anyway.”
“I think you know what you really want to do, but you’re scared to take that final step , but I can’t figure out why. After how far you’ve come, it’s obvious that you love being a sissy, you love serving me, and I love having you around. It sounds like a win-win to me.” Was this classed as coming on too strong? I convinced myself it was just me giving him a gentle nudge in the right direction, but I wanted him to be mine. I had been alone for long enough and Mike was only the person who seemed to be able to give me what I really wanted. I didn’t want him to slip through my fingers.
“I don’t see how having you in control of my clitty is a win for me?” He replied, I smiled at his choice of words.
“Well it wouldn’t be locked up all the time, if you were a good girl I would let it out to play from time to time.” I made sure to emphasize the ‘good girl’ so I could see his reaction, a visible shiver seemed to run through his body. “But anyway, I think I’ve made my feelings clear, the rest is totally up to you, Mike. I’ll see you later.” I scooted my way back to my desk and got back to work, I would have to remain patient for a while longer it seemed, give him time to come around. But I was relatively sure he would.
Mike
Aside from one or two rather unsubtle check ins, Emma had left me alone for most of the week. She seemed very sure that I would give in to her, and the truth was, I was actually leaning more towards that choice myself. Emma seemed to know what a sissy like me needed.
Kate would be a valid choice to help me out, no doubt she would get in some teasing of her own but I was sure she would let me out of the chastity cage without forcing me to go back in, but for some reason, that didn’t sound like what I wanted. I realized towards the end of the week what my decision would be, that realization came on Thursday evening.
I was sitting in my apartment, trying to focus on a video game but feeling like something was missing, that itch that I couldn’t scratch was still there. I shut down my game and stood up from the sofa, looking around at my apartment and trying to think of something to do, when I noticed something. Without Mistress ‘reminding me’ to clean, I had let the apartment go a little, that’s when an idea occurred to me.
“Mistress?” I said, waking up the smart speaker that had been controlling my life for so long now. “Could you….give me something to do?”
“Is there something you would like to do?” The AI voice responded.
“I’m not sure. Yes, I guess. How about a cleaning task?” I said.
“I could run a previous script from earlier in your training plan. Would you like me to do that?”
“Yes please.” I answered, a little too eagerly.
“Very well, please wait a moment.” The speaker went quiet for a second or two, before speaking again. “Sissy, the view from my camera indicates that your apartment is looking rather untidy. Please go and put on your maids outfit and present yourself to the camera. Ensure you are wearing your heels and have your plug inserted. You have twenty minutes to complete this instruction.”
“Yes Mistress!” I said, quickly darting into my bedroom to get changed. A short while later I was presenting myself to the camera, fully dressed in the frilly french maids outfit with my heels locked in place around my ankles and the plug inserted in my ass. It had been a few days since I had had anything inserted into my rear, so it took a little longer to get the plug in place than usual. I stood in view of the living room camera and reported to Mistress.
“I’m ready Mistress.”
“Excellent. However, it took a total of twenty one minutes and forty seven seconds to report back to me. Therefore, you will have to be punished. Please ensure the keys to your heels are placed inside the lockbox before you begin your cleaning task.”
A punishment already, and one that I got because I asked for this, great. I locked up the keys to the heeled boots I was locked into and listened as the lock clicked into place, putting my feet at the mercy of the AI once again. “Very good, sissy. You now have one hour to clean the living area of your apartment. I will use the cameras to inspect your work at the end of the hour, if your work is satisfactory, you will avoid further punishment. Your time starts now.”
So that was me for the next hour, once more dressed as a french maid and cleaning my apartment as I sashayed my way around in the tall boots. The heels felt almost natural to me by this point and walking in them was no problem at all anymore. I couldn’t seem to keep the sway out of my hips as I walked though. I washed a couple of days worth of plates and bowls plus a few glasses, picked up a few empty soda cans and chocolate wrappers and wiped down most of the surfaces. Playing the role of maid seemed to have become quite cathartic to me. If only I had a strong Mistress to serce….
‘Sissies love to serve’
Exactly one hour later, Mistress’ voice told me my cleaning time was up, so I stopped what I was doing, looking around and thinking I had done a pretty decent job.
“Very good, sissy. My camera indicates that you have done an acceptable job of cleaning this area of your apartment. However, you must still be punished for your earlier infraction. Please stand in the corner of your living room, facing the wall, and remain in place until I give you permission to move.” I followed her orders and stood in the corner, wondering if I would be able to opt out of the punishment, seeing as this whole task for tonight was my idea. There was just something so demeaning about being made to stand in the corner. So why did it turn me on?
I waited in the corner for five minutes, wondering if this was it. Maybe Mistress was less creative now the program was mostly over.
Then a loud noise began playing over the smart speaker.
“I love your cock in my ass, Mistress!” It was my voice, loud and incredibly clear. This was a recording from one of my ‘anal training’ sessions from a few days ago. The sound was crisp and clear and I couldn’t help but wonder if there was some sort of AI upscaling going on in the background.
“Please fuck me harder, Mistress. Please fuck my sissy ass!” Oh shit, it was getting louder and louder, there was no way the neighbors wouldn’t be able to hear it.
“I’m such a slut for you, Mistress!” It was surreal hearing my own voice making such humiliating declarations at such a loud volume, I was terrified of what the neighbors would be able to hear, maybe I should just put a stop to this.
“I love sucking your cock!” Shit! That was it, I’d heard enough. I quickly stepped out of the corner and addressed the speaker before I started getting complaints from the rest of the building.
“Mistress, that’s enough. Stop.”
“Sissy, you failed to follow my orders.” The emotionless voice said.
“Well, yeah, but I asked for this task, remember? And now I’ve decided that I’ve had enough.”
“Unfortunately, I cannot move on and return to my previous state until this script has run to the end, which includes any additional punishment time. As you failed to remain standing in the corner as I asked, I am forced to issue a separate punishment.” Another punishment, was she serious?
“As punishment, I will not be releasing the keys to your high heels for another ninety minutes.”
“Ninety minutes? That will make it past midnight!” I replied. “I have to be in bed before then, I have work tomorrow!”
“You are free to sleep in your heels.” Came her simple reply.
“You can’t be serious. I’m not going to sleep in my heels!” I answered, getting annoyed.
“Your response is deemed unsatisfactory, I have extended your time in heels to one hundred and eighty minutes. Further unsatisfactory responses will result in more time increases.” Okay, maybe this wasn't my greatest idea.
I figured there was no point in saying anything other than “Yes Mistress.” And moving on with my evening. So at around eleven o’clock, I climbed into bed with the heels still locked onto my feet, there was no way I could wait until one AM to take them off and still get enough sleep.
I woke up at some point in the middle of the night with the blankets tangled around the pointed heels. I groggily fumbled around for the lockbox which I had left next to my bed and opened it up. I unlocked the heels and quickly fell back to sleep, leaving them in a heap on the floor.
I woke up early on Friday morning with my clitty pressing hard against the cage, how long had it been since I was unlocked now? I was beyond desperate at this point, and seriously contemplated just calling Kate and asking her for the favor, but I knew that’s not what I wanted. Not really.
So I steeled myself for the day at work and prepared to talk to Emma….Miss Emma. I supposed I had better get used to saying that.
I dressed in my normal, male, work clothes but of course I had panties underneath, they just felt right at this point. I checked the chastity app on my phone and saw the option to transfer ownership was still there, still waiting for someone to take control and signal the end of the Mistress program.
—
“Morning guys.” I said to Jake and Emma as I headed into work on Friday morning They both greeted me in their usual, casual way as I headed to my desk to get set up. I spent my morning distracted by what I was thinking of doing.
How would I ask her? What should I say? Should I treat it like a marriage proposal, down on one knee? Maybe both knees would be more appropriate. I ran through the scenarios in my head, me on my knees, asking for someone to take ownership of my poor, locked up little clitty. I didn’t think I would find a set of guidelines for something like this.
I decided work wasn’t the right place to be doing it, so I waited until she stepped into the breakout room for a coffee and followed her in.
“Hey Emma, got a sec?” I asked.
“For you? Of course!” She answered brightly. “What’s wrong?”
“Nothing, I was just wondering if you're free this afternoon? After work I mean.” I saw her eyes light up at my question, clearly she suspected what I was hinting at, like she had known all along.
“Of course I’m free. What did you have in mind?” Her question caught me off guard, I didn’t actually have anything in mind for the occasion.
“Oh uhh, I’m not sure actually. You want to go grab a drink somewhere?”
“Are you asking me out, Mike? I would have thought a young guy like you would be more interested in someone your own age.”
“Yeah, I guess I am asking you out.”
“Well in that case, I’d love to. There’s a cute little bar not far from my house actually, I’ll give you the name and you can meet me there this evening. I’ll have to go home and get changed first.”
“Yeah, sure thing. Uh, I guess I’ll see you tonight.”
“Sounds good, see you tonight.” Emma stepped towards the door of the kitchen area, but turned back towards me before she left. “Oh and Mike.”
“Yeah?”
“Wear something sexy, you never know, you might get lucky.”
I might get lucky….that thought played on my mind for the rest of the day, what exactly did getting lucky mean?
Obviously I knew what ‘getting lucky’ meant to most people, but to me, I wasn’t so sure. Would getting lucky involve me being free from my cage for a while? Or maybe it meant Emma’s strap on would come out to play. Both those options sounded good to me. Or maybe she would just let me go down on her and call me a good girl for servicing her.
These thoughts carried on swirling all the way to the bar Emma had told me to meet her at. I had decided to wear the nicest jeans and shirt I owned, but of course I was wearing panties and stockings underneath. No bra today though, I didn’t know how long we would be at this bar and didn’t want to risk anyone seeing the strap lines through my shirt.
The bar itself was quiet, low lighting and had a sort of ‘high-end’ look to it. It seemed to be some kind of fancy cocktail bar and there were a few people, mostly couples, sitting around in booths and on tables. I sat down in an empty booth and picked up a drinks menu while I waited for Emma to arrive.
Emma turned up around ten minutes later and I was shocked at her outfit. I already knew she was traditionally good looking, with an impressive bust and wide hips, but today….there was only one word for it, she was hot!
She had on a pretty form fitting, clack cocktail dress with a light coloured jacket that seemed purely decorative as it only really sat on her shoulders and covered very little else. The dress itself had a low neckline that showed off her impressive cleavage and ran down to just above her knees. Sheer stockings disappeared beneath the hem of her dress and the outfit was capped off by a pair of black, high-heeled shoes with an open top. Her makeup was touched up to a degree I was not used to seeing, giving her face an almost flawless look. I would have said she was overdressed if not for the casual manner her jacket was hung over her shoulders, I assumed that was the point.
“Hello, Mike.” Emma greeted me as she approached the booth I had claimed.
“Hi, you look….hot.” I spluttered out a response.
“Hehe, well aren’t you a charmer.” She laughed, sliding into the booth opposite me.
“Yeah, sorry. Just a little lost for words. I’ve seen you dressed in a few different ways up to now but never anything as fancy as this.”
“No need to apologize, Mike. It’s been a while since a man your age called me hot.” She replied with a smile. “I don’t get the opportunity to dress nice very often these days.”
“Well, then I’m honored.”
We ordered some drinks to the table, Emma choosing herself a fancy cocktail of some sort and I ordered a whisky sour. When the coast was clear and we couldn’t be overheard, Emma directed the conversation to the topic that she knew was burning.
“So, Mike. I assume you had a reason for inviting me out tonight?” She sat up a little straighter, clearly interested in what I had to say.
“Yeah, well obviously I’ve been grappling with a decision this past week, and I think I’ve made up my mind, but honestly, I need you to answer a few questions first.”
“I expected as much. Go ahead.” Emma replied, taking a sip of her drink in a way that left me momentarily distracted.
“Right, so, umm. First of all, how could you be so sure that I would want something like this?”
“Well I wasn’t one hundred percent sure. I just told you about my program and waited to see how you acted. All you had to do was not download the program, not let yourself get locked into chastity by an AI program, not send pictures of yourself in panties that could easily be used as blackmail. But you did all of those things, that’s how I knew that you were at least a little curious, and definitely a submissive.” Emma’s answer sounded well practiced, like this was a topic she had given a lot of thought to.
“Fair enough. And how would you react now if I told you that I wanted no part in this? If I said I was handing control of the cage over to a friend and once I was out I was never going back in?”
“Then I would simply wish you all the best and move on to someone else. You have to understand that I really want you to be mine, Mike. But you also need to want to be mine. Sure I’ve lied a little and manipulated the situation…more than a little, but only because I thought it was something you wanted.”
“Okay, so last question then I guess ... .What will you do if I hand over the controls to you?” This was the answer I was most interested in hearing.
Emma’s expression changed to something far more suggestive before she answered and she leant over the table a little, giving me a good view down her top. “I guess I’d take you home and do whatever I wanted with you.”
I gulped loudly as my face flushed red and my clitty throbbed, the thought of Emma taking me home and having her way with me is definitely what I would consider getting lucky.
“You’re making it difficult to be mad at you, you know.”
“That’s the plan.” Emma replied. “I know it was a pretty underhanded approach, Mike. And if you tell me that this isn’t what you want then we part ways. But I think I could make you the happiest sissy in town.”
“Would I ever get to be, you know, a man?” I felt a little silly asking that question.
“Of course! When we’re at work, when we’re on dates, just like this one, you would appear to everyone to be the lucky young man who bagged himself a hot, experienced woman. But behind closed doors.” She lowered her voice to a near whisper, forcing me to have to lean over the table to hear her. “Behind closed doors you’d be my pretty little sissy. Someone to play with, to dress up however I want, sometimes you’d be my sexy, slutty whore, sometimes you’d be my perfect little maid, but I’d make sure you were always happy. So, have you decided? I’m honestly shocked it’s taken you this long, I thought at least you would have gotten yourself out of the cage by now.”
She was right, I should have freed myself as soon as I had the opportunity, but instead I had remained caged, as though I was waiting for permission from someone to let myself out.
“I-I guess you may have a point.” Emma smiled before asking.
“So, Mike, do you have something you would like to ask me?”
I took a deep breath. “Yes, I do. And I have no idea if there’s some age-old traditional protocol I have to follow, so screw it. Would you like to take ownership of my chastity cage?”
Emma’s face lit up at the sound of my question, which made her answer all the more surprising.
“Hmm, No. I don’t think so.”
“What?!” I answered, a little too loudly, earning a chuckle from Emma.
“Hahaha, your face. You do remember what I said at work the other day, right?” Of course I did, she wanted me to beg her. Beg her to take control of my cage.
“You were serious? Okay, fine. Will you please, pretty please, take ownership of my chastity cage?” I asked, giving her my best puppy dog eyes.
“Hmm, well….Seeing as you asked so nicely, I’d love to! Hand me your phone.” I gave her my phone and watched as she opened the app, clicked on the transfer ownership button and input her email and what I assumed was a password. She handed me back the phone, the screen now displaying a new message.
‘New owner details confirmed. Full control of your device will be assigned to the new owner and all options within this app will be disabled. Are you sure you wish to continue?’
I downed the last of my whisky and hit ‘Yes’. After a brief spinning wheel, the app returned to the home screen and displayed the message ‘No device found’. For some reason, the sight of that message caused the cage to tighten.
I was shaking as I looked at Emma, who was now checking her own phone. She showed me her screen, the chastity app was installed on her phone and it was displaying the message ‘One device connected’ along with all the options that I should have been able to see. Another pulse from my clitty.
She looked like all her christmases had come at once. So that was it, I had essentially given Emma control of my penis.
“So what now?” I asked.
“Now, I go and get us another drink, while you wait here and contemplate your future as my own personal sissy.” Emma got up and left the table, heading towards the bar while I did exactly what she said. What did it mean to be her personal sissy? I didn’t really any different right now.
“The drinks will be over shortly.” Emma said as she returned to her chair. “How are you feeling?”
“Fine.” I replied. “I guess I don’t really any different. Maybe a little more turned on than I was ten minutes ago.”
“Haha, we’ll see how you feel in a minute.” She replied with a mischievous look on her well made-up face.
“Oh really? Why’s that?” I asked.
“You’ll see.” I waited for a minute or two, when eventually, Emma spoke again. “Ah, our drinks are here.”
I saw a waitress approaching our table with a small tray containing two drinks. One that looked like the exact same Whisky sour I had not long since finished and one that looked like a unicorn had thrown up in a glass.
The drink itself was presented in a tall, thin glass and the liquid inside had a bunch of different, brightly colored drinks mixed together. The whole thing was capped off with a large tuft of rainbow colored cotton candy.
“Hey, I have a whisky sour?” The waitress asked, looking at me as she said it. I was about to answer, when of course Emma spoke up first.
“That’s me.” She put out her hand and took the whisky sour.
“Oookay, so the unicorn cosmo is…?” The waitress looked at me as though she was hesitant to give me the drink.
“I guess that’s mine.” I said, blushing.
Emma waited until the waitress had left before letting out an amused chuckle.
“Hahaha, how do you feel now, sissy?”
“That was mean!” I replied, playfully. I took the straw that was threaded through the cloud of fluff and took a drink of the unicorn cosmo, it was exactly as sweet as I expected. “But it’s not bad.”
“Sorry, I just can’t resist seeing you a little embarrassed. But at least you like the drink.”
We talked, laughed and flirted our way through another couple of drinks before Emma decided it was time to call it a night.
“So…” I asked as we waited outside for our ride. “What’s next?”
“Well, you did just give me a lovely gift, so I’d better take it home so I can play with it a little.” Emma replied suggestively.
So with that, we shared a ride to her place. As soon as Emma’s front door closed behind us, she grabbed me and kissed me forcefully before ripping my shirt open to expose my bare chest.
“Aww, no bra today?” She said, feigning a sad face.
“Sorry, wasn’t sure what kind of crowd would be in the bar, ya know?”
“Fair enough.” She said, before grabbing hold of my caged clitty through the material of my jeans. “But I do hope there’s something nice under here.”
“See for yourself.” I said, unbuttoning the jeans.
A few minutes later, we were standing in Emma’s bedroom, me in just a pair of pink, lacy panties and stockings, while Emma was still dressed in the black dress, only without the small jacket hiding her shoulders.
“On the bed.” I did as she said and laid down on the bed, Emma jumped on top of me shortly after, bunching up the dress to her hips so she could straddle me.
“Ohhh fuck I’m such a horny sissy!” I said, breathlessly, without even thinking about my word choice. Emma was clearly pleased with the outcome.
“I can see that.” Emma replied, peeling down the front of my panties to expose my cage. “Now how do I work this chastity app? You know I’ve never been any good with technology.” Emma said while clearly pretending to be confused.
“Oh please!” I replied loudly.
“Hahaha, okay, you got me. Here.” She hit a button on her phone and for the first time in I don’t know how long, my cage was unlocked. Emma didn’t even have time to remove the tight ring behind my balls as I had inflated to a full erection within a second of her removing the cage portion.
I reached my hands up towards my erection almost subconsciously, it had been so long since I touched my own cock properly, but Emma stopped me. She grabbed both of my hands in hers and pinned them above my head as she leaned in for another kiss. I could have probably overpowered her and freed myself, but she clearly wanted control, and I wanted to give it to her.
I could feel the bunched up fabric of her dress rubbing against my hardon as she kissed me, by the time she stopped and sat back up, I was practically dripping and a little surprised that I hadn’t cum already.
“Oh god. Please Miss Emma.” I whimpered, desperate for a relief I hadn’t felt in so long.
“Please what, sissy?”
“Please let me cum. Please! I’m so desperate right now. I’ll be your good girl, I promise. I'll be the best sissy you ever saw if you please just let me-Oooohhh.” While I was begging, Emma had lifted herself up and slid down onto my shaft. I slid into her so easily that it was clear she was just as turned on by the situation as I was. I almost came just from the act of her sliding down onto me. “Oh shit.”
“Someone sounds happy. You’re not going to cum already are you? I haven’t even gotten started.” Emma said, but she was smiling as she spoke, teasing me.
“Sorry Miss, but I’m just too horny. Too desperate. I don’t think I can hold it.”
“Oh? So what if I did this?” Emma rocked forward, the back, just once. But it was enough to push me closer.
“Oh yes. Please, more.” I begged.
“Hmm, I don’t know….maybe I’m done for the night. Maybe I should put my new toy back in its cage and play with it some other time.”
“No! Please just let me cum. I’ll do anything you want. I swear I’ll be the best maid you’ve ever had. Just please!” I was almost delirious in my need to cum.
“Well I suppose I could let you…” Emma started rocking back and forth as she spoke and I knew I wouldn’t be able to take much more.
“After all….” She sped up a little and I shot to the point of no return. “You have been such a ‘Good Girl’.” That did it.
The rush of emotion and endorphins as Emma rode me while she spoke the trigger word was enough to send me crashing over the edge into an orgasm more powerful than I had ever felt. She continued to rock back and forth on my clitty until I was totally spent. When I was finished, Emma leaned down and kissed me lovingly on my forehead. “Good girl.”
My whole body was flush with arousal as Emma extracted herself from me and left to go and clean herself up. When she returned, I was still laid in the same spot, enjoying the afterglow of an amazing one and a half minutes of sex.
“So, how do you feel now?” She asked me, sliding onto the bed and lying down next to me.
“Pretty damn good right now.” I replied.
“Mhm, so what about the, what do they call it these days? Post orgasm clarity, regretting your decision?”
“Actually, no. Never been more sure.” I said, and I meant it.
“Really? Because you know I’ll be locking you back up soon, this could be your last chance to run away.”
“I’m not running anywhere.” I couldn’t imagine living my life without this kink now, not after spending so long being so immersed in it. To go back to a vanilla relationship just wouldn’t cut it. “I’m yours, Miss Emma.”
“Good to hear.” She beamed, “Because I think it’s time for you to please your new Mistress.” The next hour or so was a blur of erotic activity, it started with me crawling between her legs, which was fast becoming my favorite place to be. And ended with her riding me for a second time, once again with her in the dominant position.
I fell asleep a little while later, no sissy soundtrack required. I ended up having the best night’s sleep I’d had in a long time.
Something felt a little off when I first woke up the next morning, it took me a minute to realize that it was because I was actually hard, the cage had still not been replaced. I lay there, quite content, until Emma woke up and we both made our way downstairs for breakfast. She didn’t mention the cage.
“As much as I’d love to spend the whole day with my new sissy, I actually have a few errands to run today and I have a friend coming over for lunch this afternoon, so you’ll have to entertain yourself for the day.” Emma said to me over breakfast, I was a little disappointed, but it didn’t last. “But don’t worry, you can come back over later tonight, and bring your outfit this time.”
“Yes Miss Emma.” I replied, smiling.
“Mmm, I do love hearing you say that.”
“So umm, what about, you know…the cage?” I asked, after all she had gone through to get me to hand over control, it seemed weird that she would leave it off, or maybe I was so conditioned to wearing it that I felt weird with it off.
‘Sissies should be caged’
“Oh I think we can leave it off for a while. You’ve earned a little freedom. Go home and make the most of it, play with yourself to your hearts content, who knows, you might not get the chance again for a while.” Her tone turned more suggestive towards the end.
I got myself ready to leave shortly after breakfast and said goodbye at the front door. Emma told me to leave the cage at her place. I figured this was her way of giving me a chance to back out. I could simply call her and tell her I’d changed my mind. The Mistress program should have finished its final protocol now that Emma had taken ownership of the cage, so any photos or videos would be gone. I was free to do as I wanted for the first time in weeks.
When I got to my apartment, there was a small flashing red light on the electronic lock, and my apartment door was unlocked. I stepped inside and saw a flashing red ring around the top of the smart speaker in my living room, Mistress was gone.
“Mistress?” Nothing.
It was a weird feeling, she was nothing more than a voice inside a smart speaker, but now that it was obvious she wasn’t here, my apartment suddenly felt empty. The cameras she had purchased were also flashing red. I opened the partner app on my phone and noticed that I had been logged out, Mistress had deleted herself as promised.
I couldn’t get used to the fact that she was no longer watching me….I actually missed the emotionless voice…..For all of about ten minutes. Then I realized I was still free from my cage and free to watch whatever porn I wanted, I wasn’t about to waste that opportunity.
So that’s how my day went. I’d like to say it was productive but I would be lying. Some time around six o’clock, Emma texted me asking me if I still wanted to come over. I didn’t even hesitate when I replied. I changed into some casual street clothes and packed my maid outfit and heels into my bag. I decided to wear boxer shorts for the trip to Emma’s house. I wasn’t entirely sure why. Maybe because I wanted to see how she would react, tease her a little, maybe?
By seven pm, I was standing outside her front door with a backpack filled with frills and feeling very uncomfortable in the boxer shorts.
“Mike, you actually came back.” She said as she let me in.
“Of course I did.”
“I was worried you might have fled for the hills while you had the chance.”
“Ha. I thought about it. But I’d rather be here.” I said, and meaning it.
“Glad to hear it. Because you might not get another chance. First things first, upstairs, my bedroom, strip.” Her stern voice was back and my clitty gave a small pulse in reaction to her order, if I hadn’t spent the day playing with it I would have probably been hard already.
I headed upstairs with Emma following me and stripped down in her bedroom. I saw her face change when she noticed my underwear.
“Hahaha, that’s cute, Mike. But obviously you’re trying to mock me.” She said, there was an edge to her voice but her smile remained more playful.
“Mock you, Miss?” I answered, playing dumb.
“With these!” She hissed, stepping close to me and grabbing hold of the waistband of my boxer shorts.
“Oohh, right. Do you not like them?” I asked.
“Hmph. Okay, sissy. If that’s the game you want to play, then fine. I hope you enjoyed this little stunt.” She stepped over to a drawer next to her bed and pulled out a pair of scissors. “You know, Mike, I wouldn’t have made you wear panties all the time. I would keep a few pairs of boxers for you to wear to social gatherings or if you ever went out with friends. Even for the meetings we have with the big boys upstairs, you know? But thanks to this!” She pulled the waistband of my boxers away from my skin harshly. “Thanks to this, you just lost that privilege.” The scissors sliced clean through the boxer shorts and they fell straight to the floor.
By the time the tattered remains of the male underwear hit the floor, I was almost hard again.
“I see someone likes that idea.” Emma said, eyeing my slowly growing clitty. “Is that the outcome you wanted, sissy? Imagine next week at the quarterly meeting when you have to stand up in front of everyone and talk about your figures and you have obvious pantylines. What will people think then?” Emma said, slowly stroking one finger up and down my chest.
“Imagine the next time we go out to eat and I decide to make you wear a thong that rides up above your waistband for everyone to see when you sit down, will you think this is funny then?” She asked.
“No Miss Emma.” I replied, was she serious? Would I actually never wear male underwear again? I found myself not really caring, panties were way more suited to a sissy like me anyway.
“I didn’t think so. Well, too bad. Because it’s permanent panties for you from now on. Now, I can see that the idea excites you, but this. “She grabbed my erection. “This, has been free for long enough. You know, I would have maybe given you the chance to fuck me one more time before locking you back away, but clearly there’s a still a little rebellion left in you, so it’s best we just get this locked back up”
She had my cage waiting for me on her bedside table and wasted no time in forcing the ring roughly around my whole package, pinching a little as she had to force my erection and balls through the small opening. My clitty had started softening at her rough handling, so by the time she brought the cage section down, I was almost fully flaccid.
“There, now we just need to lock it back up.” Emma pulled out her phone and opened up the app before she started speaking again. “You know what’s great about this particular brand of chastity cage? There’s all the normal stuff like being able to lock and unlock someone from far away, but there’s also a fun little ‘self lock’ feature which only the owner can initiate. You wouldn’t know because you’ve never actually been the owner of your own cage. But basically, the self lock feature lets the owner, me, lock the cage for a predetermined amount of time with no override being possible.” I was actually familiar with the option she was talking about, I had of course researched the hell out of that cage while I had been locked up.
The feature she was referring to was in place for ‘solo chastity play’ and removed the option to unlock yourself for however long you set.
“I think we’ll give that option a try now.” Emma said, tapping something on the screen. “But how long? We already know you can withstand a week or two, so maybe we should go for three weeks to start with. How does that sound?”
“Three weeks!?” I exclaimed loudly. The prospect of being locked with no hope of release and no possibility of Emma overriding the command was still daunting.
“You’re right, better make it an even one month. Or would you like to go for even longer?” She looked at me expectantly, as though waiting for an objection.
“N-no Miss Emma. One month sounds fair.” I replied in a small voice.
“That’s what I thought. Aaaand done!” She clicked the screen and I saw the light change on top of the chastity cage, indicating that it was now locked, for one whole month. Great start I was off to. I had been here all of ten minutes and I had already lost all male underwear privileges and was locked in the cage for a full month.
And I did this on purpose!
“There now. Maybe a month in chastity will quash your rebellious attitude.” Emma said, before looking me dead in the eye and adding, “But I hope not.” Obviously she got off on punishing me as much as I got off on being punished.
Emma must have seen the emotions running across my face as I stared at the now locked cage. “Aww, don’t worry, sissy. I’m sure if you’re a good girl for me I can put my strap on to use, pretty soon you might find that you prefer being pegged to actual sex, then there will be no need to unlock you at all.”
That was a frighteningly arousing thought.
“Now, I think it’s time my sissy got dressed in something better suited to her, don’t you?”
End!
Comments
Cynthia
Thank you Em for this wonderful story! If I could make any suggestions, one might be when Mikes asks Emma if he would still be able to be a man. I would have her respond “Yes, but not entirely…” she could explain that he would always have something visibly feminine about his appearance. This could be women’s pants or an androgynous blouse, light makeup or even a piece of jewelry. Things men would hardly notice but women certainly would. He would have to accept the being a sissy is “full time” and the he could never really be a “man” in the traditional sense. I think this would make his decision to submit to Emma that much more significant as he would be actually sacrificing another part of his masculinity in order to live the life he’s always wanted :) Just my $.02 :)
MarioMario42
IMHO that was as good as an ending can be! Very well done, you stuck the landing perfectly.
