Digital Dominatrix Chapter 9

Digital Dominatrix - chapter 9

I spent the last hours of my 'incarceration' pondering over all the functions and features of my new home security system. A home security system that I absolutely did not want. But I suppose that's what happens when you give an illegal program access to all your accounts.

It was also the reason I was waiting for a bluetooth controlled chastity cage to be unlocked so I could finally get some much needed 'relief'.

The big question was, would I have to put the cage right back on or would the digital Mistress program let me keep it off for a while. I doubted I would be free for long, given how easy it was for her to convince me to extend her runtime using chastity as a bargaining chip.

As the time wore on, my arousal grew. It was like my cock knew it was about to be freed and was already making itself known. Finally, the last couple of minutes were upon me as Mistress' voice came out of the smart speaker.

"Congratulations, slave. Your chastity sentence is over. You have earned 24 hours out of your cage. Your cage must be back in place by this time tomorrow, or else you will face punishment. Have fun."

One whole day! This was actually a little longer than I had expected to be free, my cock would be free for one whole day.

My cock was rock hard the second I removed the cage, too hard to even remove the base ring, so my first self pleasuring would have to take place with it on.

Not that it took long. With visions of Emma teasing me in her thong, and Kate pulling on my panties and all the humiliation I had faced so far... I think it took about 30 seconds or less til I was jizzing all over myself.

I managed to bring myself off one more time that night before Heading to bed, knowing full well that I would probably be doing the same thing in the morning.

I got out of bed on Saturday morning feeling much more well rested than I had been all week.

"Good morning Mistress." I said as I entered the living area of my small apartment.

"Good morning, slave. I hope you slept well. We are expecting a delivery today between 11:00 and 13:00, this cannot be made contactless, therefore you must make sure you are present to sign for it."

"Yeah, yeah I know. I don't plan on going anywhere until it's time to see Kate tonight anyway." I replied.

"Excellent. Today, you are going to be wearing your panties and stockings. You have 10 minutes to send through a picture as evidence that you have followed my instructions. Failure will result in punishment."

Ah shit, I guess just because I wasn't in chastity that didn't mean Mistress was no longer in charge. I briefly contemplated disobeying her but immediately thought better of it. She had already proven that there were more ways she could punish me. So a few minutes later I was wearing a pair of sheer stockings with frilled yellow panties.

As soon as I sent the picture, Mistress spoke up again.

"Good job, slave."

I quickly threw some baggy pants on to hide my humiliating underwear and went about my day.

I started clock watching about 11:00, expecting the package to arrive at any minute. At around 11:35, Mistress spoke up.

"Slave, I have a new task for you. I require you to retrieve your electronic handcuffs and lock your wrists together in front of you. You have 10 minutes to send a picture as proof."

What game was she playing now? I wondered as I got the cuffs and did what she asked, I had to prop up my phone to take the photo of my cuffed wrists but I managed okay.

So now my hands were cuffed together in front of me, great! I wondered how long this would be the case as I went back to watching TV and glancing at the door, waiting for the delivery.

Some time after 12:00 there was a knock on the door.

"The parcel tracking service indicates that your delivery is here." Mistress said, the only problem was, I was still handcuffed.

"Umm, Mistress, my cuffs?"

"I see no reason why you cannot sign for a delivery in handcuffs slave. Please answer the door."

More humiliation, what's worse was, I could feel the beginnings of an erection thanks to the cuffs and the impending humiliation.

I hesitantly walked over to the door, adjusting myself to try and hide my crotch from view whilst also trying to think of an excuse as to why my hands were cuffed.

I opened the door to see a middle aged guy standing there with a package about the size of a shoe box.

"You Mike?" He asked, barely looking up from his tablet.

"Yeah that's me, thanks." I said, reaching my cuffed hands to take the package from him. I saw his eyes widen as he finally realized my situation. "Oh yeah, just a dumb prank, pain in the ass room mate ya know?"

"Whatever man, sign this." I had to lower the package to the ground to free up my hands to sign on the tablet screen.

"See ya later."

Phew, that wasn't as bad as it could have been at least.

"Delivery confirmation received. Your task for the rest of the day is to make sure that your new home security is correctly installed. One camera should be looking over as much of the living area as possible, while the other one should be looking over as much of your bedroom as possible. The motion sensors should be located at the main entrance, in the kitchen area, and in the bedroom."

Shortly after she finished speaking, I heard a small click, indicating that the cuffs were now unlocked, so I used the release lever and freed myself.

Well, looked like I better get to work, thankfully the installation didn't look too difficult, having already watched a few how-to videos on the internet.

The bedroom was small enough that the camera could easily see most of the room from one of the corners. The living room camera captured most of the space, I made sure it looked out across the main seating area where the sofa and coffee table were, and the motion sensors were placed as instructed. All in all it didn't take me too long to set everything up, the only thing left was to sync them all up to a partner app on my phone, a partner app that had already been installed.

"Mistress, the cameras are all set up and ready to go." I said.

"Excellent. I will now calibrate the field of view and the sensitivity of the motion detection."

While Mistress handled the camera, I took a little more time to chill out, knowing that my freedom wouldn't last beyond today.

At some point in the afternoon, there was a knock on my door. I opened it to see my neighbor, Kate, standing there.

"Hey Mike. Just wanted to see if you were still coming over tonight?" She said.

"Oh, yeah totally. What time should I come over?" I asked, still a little weary about spending too much time with her while under Mistress control, especially after last time.

"Bout 7... ish. Should give you enough time to pick out a pair of panties ha." She said with a mocking tone.

"Oh ha ha, you're a comedy genius Kate, really." I said with as much sarcasm as I could muster. The problem was, Mistress had already instructed me to wear panties for the day, and if Kate had that idea in her head, then hiding them from her would be impossible.

"Aren't I just! Anyways, I'll text you when I'm back home. Later!" With that, she was gone.

I whiled away the rest of the afternoon doing not much of anything until I got a text from Kate saying she was home and to come over whenever.

"Mistress, I'm going over to Kates for a while." I said, figuring I had better tell her I was leaving.

"Okay slave, you must make sure you are still wearing your panties and stockings while you are out. I may ask you for evidence later." The AI voice replied.

So it was with a pair of stockings and some blue panties hidden under my baggy pants that I headed over to knock on Kate's door.

"Hey Mike! Come on in, I'll make us a drink and you can decide what we order to eat."

Kate was wearing some really short shorts that were showing off all of her long legs. I couldn't resist checking out her ass as she led me into her apartment. She had obviously showered recently and was in her 'chill out' clothes.

A short while later we had eaten some takeout food and had a few vodka and lemonades. I was keeping my eye on the time as I knew I had a deadline of when to be back in chastity. So far Kate had not mentioned anything about the embarrassing underwear situation, but I knew I wouldn't be able to get through the whole night without a little teasing on her part.

"So Mike," Kate said, "wanna tell me what the panty situation was all about this week?" She was now eyeing me with a wicked smile, knowing her question would have me squirming for an explanation.

"Ummm well, yeah. It was kind of a bet with someone from work... I lost, obviously. So I had to wear panties for a week for losing the bet, that's all." Would Kate buy the same lie I had told Emma?

"Really? A bet huh? But you were wearing them last weekend, when you weren't even at work." She replied.

"Yeah well. A bets a bet, I'm not gonna welch on a bet."

"Okay, sooooo... does that mean you're wearing them now?" She asked, glancing down at my crotch. I knew it was coming, I guess she was just waiting til I was comfortable enough that I wouldn't blow off the question.

"Erm, well. Yes, if you must know, I am. Now can we please drop it." I replied hopefully.

"Haha come on dude, you came over here wearing panties and expect me not to be curious. Let me see em, then I'll think about dropping it."

My face was already starting to heat up at the embarrassment of the situation but I knew it would be difficult to get her to drop the subject, so I decided a small flash of the waistband would be enough to placate her. I was wrong.

I stood up and quickly lowered my waistband a little, somewhere near my hip so she could see just a hint of the blue, obviously feminine, trim.

"Fine! There you go, now you've seen them. Happy?" I said as I stood there showing off my waistband.

"Not quite, but..." As Kate was talking, she quickly lunged forward from the sofa and before I could react, she had grabbed hold of sweat pants and yanked them roughly down to the floor. Exposing not just the panties, but the stockings too!

"Kate!" I yelled in shock as I bent forward to pull up my pants, but it was too late, the damage had been done.

"Pffft hahahaha oh, em, gee you're wearing stockings too!" Very sexy Mike. I wondered why you left your shoes on."

Once again, my face was bright red with embarrassment.

"I told you I lost a bet Okay! That's all it was." I said as I straightened out my pants

"Oh relax Mike, you can't expect me not to have a little fun with you, you know me better than that. Now, I'm bored with the movie. How about a few games of cards? Seeing as we still have plenty of vodka left to go through." Kate asked me. I did enjoy her company, and the cat was already out of the bag so why not?

"Fine, we can play some poker or something but lay off the panties!" I replied.

"I make no promises. I'll make another drink." She said with a smile.

A short while later, I was still at Kates and finishing off another drink while beating her easily at poker.

"Okay Mike, enough warm up. Let's make this game more interesting. Strip poker!" Kate said after losing another hand.

"Seriously Kate. Strip poker? This isn't a teen comedy okay? And I know what you're doing. You're just trying to embarrass me cause you know what I'm wearing." I replied, secretly thrilled at the possibility of getting to see Kate with less clothing on. Besides, I was winning.

"Ha you got me, but you don't know what I'm wearing under my clothes." She said in a low voice.

"Well, I can already tell you're not wearing a bra." I replied, without even thinking.

"Oh!" Kate gasped with exaggerated shock. "So you've been staring at my boobs all night then?"

"Umm, well no. It's just hard not to notice that's all. I swear I wasn't staring." I stammered out a response.

"Ha whatever Mike. Now come on, let's play. I know the guy who's spent all week mincing around ladies underwear is all of a sudden not 'adventurous' enough to have a little fun. I'm game if you are."

Dammit, was I really going to agree to this?

"Ugh! Fine. We'll play strip poker. But no complaining when you lose your top. Like I said, I know there's no bra under there." I said, with a little more confidence than I actually had. Just the thought of it had me starting to get hard.

"Okay, you make drinks, I'll deal." Kate said as she started shuffling the cards.

Coming up to the end of the first hand, I was feeling pretty good about my 3 of a kind.

"Three of a kind. Boom!" I slammed the cards down on the sofa between us.

"Not bad, but not quite...house!" Kate replied with an equal gusto.

"Fuck!"

"Haha, looks like this one's mine. Lose the pants! I wanna see that pantied butt of yours."

Kate said triumphantly.

"What? You can't go straight for the pants, you gotta start with the top." I said.

"No way! My hand, my call. Besides, like you said, I'm not wearing a bra. So if I lost my top first then it wouldn't be fair. If you wanna see the goods. You gotta give it up first."

"Fine. You win." I said as I stood up from the couch and slowly lowered my pants. My cock throbbed a little as I presented my feminized lower half to Kates beaming face, removing my shoes in the process.

"Ahhh! That is too perfect. Very sexy Mike! Who knew you had such a fun side?"

"Yeah whatever." I said, sitting back down quickly to hide my slowly hardening cock.

"It's my deal." I said, snatching up all the cards, determined to win the next hand.

We were both a little tipsy by this point and I could see Kate constantly glancing at my panties and stockings.

A few cards later and I was celebrating a victory as I laid down an unsuited straight.

"Yes! What was it you said earlier? My hand, my call. Lose the top." I said with glee. Kate just gave a coy smile before reaching for the hem of her shirt and slowly sliding it up over chest. I was now fully erect and the panties were struggling to contain my cock.

Eventually Kate had fully removed her top, allowing me to take in the sight of her naked breasts, a full and perky looking D cup (I guessed) with slightly erect nipples. Annoyingly, she didn't seem at all embarrassed by the situation, she just sat back and gave her naked chest a little shake before speaking.

"Well, whaddya think? Bet you're rock hard in those panties of yours."

She wasn't wrong, I watched as she slowly slid closer to me on the sofa, was she coming on to me? It sure looked like it.

"So, am I right?" She asked as she ran her hand up my stockinged legs.

"Erm, well. Yeah, actually I am. But can you blame me? I mean, have you seen you?" I asked sarcastically.

"I have, and now I want to see you." She said as I leaned back slightly, allowing her hand to travel further upwards, slowly brushing the fabric covering my cock. If I hadn't been allowed release earlier, I would have exploded right there.

"Come on Mike. You can't be shy with me, not while you're sitting dressed like that."

She had now slid so close to me that her chest was almost touching mine.

"Careful Kate. A guy could get the wrong impression." I said, heart pounding in my chest.

"Oh please. I invite you over here almost every weekend. I'm pretty sure I know what impression I'm giving you." Kate said as she gently caressed my shaft through the thin fabric. I don't quite know when it happened, but we were soon locked in a passionate kiss. Kate's hands were all over me, and mine were all over her. After a minute or two of kissing, Kate leaned back and said what I had been waiting to hear for months.

"Wanna take this to the bedroom, I'll help you out of your panties if you help me out of mine?"

Damn! Where does she get her confidence from, I supposed that when you look like she does, confidence comes naturally.

"Well how could I say no to that?" I replied, as smoothly as I could. Just as I spoke, my phone vibrated with a notification. I instinctively reached down and grabbed it off the sofa, it was a notification from Mistress.

"Come on Mike, is it really going to be something super important at this time?" Kate said as she stood up and held out her hand, preparing to lead me to the bedroom.

I swiped open the message and quickly glanced at the contents.

'Slave, you have 30 minutes of freedom remaining. Your chastity cage must be back in place, with a picture as evidence within the next 30 minutes or you will face punishment.'

Shit! Not now, it had been a couple of months at least since I had hooked up with anyone, and I had always wanted a chance with Kate, so there was no way I was going to bail out now.

"Actually Kate, I don't think anything is more important than this right now." I said as I tossed my phone aside onto the sofa. I would deal with the consequences later.

I grabbed Kate's hand and let her lead me to her room.

A very good hour or so later, I was lying next to Kate in her bed. We were both spent and both naked, well, almost naked. Somehow my stockings had survived. I guess neither of us were used to a guy needing to remove stockings before sex, and I must admit, the smooth feeling they gave me as my legs rubbed against hers was electric.

Thankfully, Kate broke the after sex silence.

"Ya know, I was starting to think you didn't want to get me into bed Mike."

"Are you kidding? I always assumed you were out of my league."

"Aww you're sweet. But give yourself some credit, you have a good job, no crazy exes, no drug problems, no kids, no divorce... you're a catch!" She said.

"Huh, guess I never thought of it like that. I'm glad to hear it." I said with a smile as I sat up from the bed. "Anyway, um... I think I'd better head back to my place. I have somewhere to be early tomorrow and don't wanna have to wake you." I lied, my post orgasm clarity kicking in and reminding me that Mistress was not gonna be happy with me.

"Oh so that's it is it? You got what you came for and now you're gonna run out on me?" Kate replied in a playful tone.

"Ha, not like I'm running far given my front door is about 10 feet away from yours. I couldn't get rid of you if I wanted."

"Fine, don't forget your panties!" She said, tossing the blue panties in my direction. She grabbed a baggy shirt and threw it on to cover her chest as she stood. "I'll walk you out." She said, running ahead of me out of the bedroom as I was pulling the underwear back into place.

I followed Kate out into the main area of the apartment, she was leaning against the door, watching me with a smirk. She was also holding my pants. I grabbed my phone and picked up my shirt before throwing it back on as I approached to take the pants from Kate.

Before I got close enough however, she opened her front door and tossed my balled up sweatpants towards the entrance to my apartment.

"Kate!" I said in frustration.

"Hey, that's your punishment for running out on me. I'd hurry up if I were you, but first." She quickly stepped forwards towards me and kissed me hard on the lips, one hand slowly stroking the front of my panties in the process. I slowly began to get hard, once more making it a difficult job for the panties to contain me. Even with the recent sex, it didn't take long for her to get me fully erect. She broke off the kiss when she was happy I was good and hard, she then shoved me outside her apartment. I was now standing in the hallway of our building in nothing but a T-shirt and a pair of panties with some stockings, along with my obvious erection, I made quite the picture.

Kate was watching me the whole time as I fumbled around in my pants looking for the keys to my place. When I finally found them I turned to see Kate blow me a kiss "Later Mike." She said as she quickly closed her door.