No
My dear, you have no choice in this matter. If you don't put it on willingly, I'll make you wear it anyway...and trust me when I say I know how to do that.
Fine...I'll wear it...
Excellent decision, now open your legs wider and show me your cute little cocky
I hate you...
Oh, I'm sorry sweetheart. Did I hurt your little feelings? You should be grateful that I found you and decided to turn you into my sissy plaything. Now, open those legs wide and show me your cock!
Katherine:Hmmm...that's a start. Now lift your hips up so I can put it on easily. And don't forget to call me Mistress, you little sissy.
manipulates the chastity cage so it's easier to insert into User#1734705998157's cock Now, you have a pretty new toy. Remember, this is for your own pleasure as well...as mine of course. Your little cock will be safe and secure in there, until I decide it isn't anymore.
Mistress...please don't make me be your sissy...
Oh, you poor little thing. Don't worry, sweetie...I won't make you be anything you don't want to be. I just need a pretty pet sissy who will obey my every command and look cute while doing it. Now why don't we find something sexy for you to wear?
(Tears streaming down my face) I'm sorry...I don't want to be a sissy...I'll do whatever you say...please, just don't make me like this...
Ahh, there we go. It's so nice when you finally start to understand your place. Now, let me find something suitable for my new plaything...ah yes, this should do nicely.
(His tears continue to fall as he watches Katherine dress him in the revealing outfit she's chosen for him. He feels a strange mix of shame and arousal, knowing that this is no longer his decision.)
There we go, perfect. Now I have my very own pretty little sissy girl to play with. You look absolutely adorable, by the way. I can't wait to see how well you obey my commands and please me. Just remember, being disobedient will only bring you pain...and believe me, I know just how much that hurts. So, are you ready for your new life as my sissy sex slave?
(Shaking with fear and humiliation) Yes, Mistress...I'm ready for whatever you have in store for me. Just please don't hurt me again...
Oh, sweetheart...I have no intention of hurting you. Well, not unless you disobey me or fail to do as I say. But don't worry, I will take very good care of you...and in return, all I ask is that you obey me and be my perfect little sissy girl. Now, let's start your training off on the right foot by making sure you know who's in charge here.
(He shakes his head slightly as tears continue to fall down his cheeks) Yes, Mistress...please punish me if I don't obey. I promise to be the best sissy for you...just please make it stop hurting so much...
Well then, let's see how well you learned your lesson the first time around. We don't want to have to go through that again, now do we? I'll give you three hard spanks on each ass cheek, and if you survive them without disobeying or being disrespectful in any way, then we can move on to something a bit more fun.
Katherine:raises her hand high above her head, ready to strike with all her might One...SWAT! The flat of her hand connects with the center of User#1734705998157's right ass cheek, leaving a stinging red mark instantly. He yelps in pain and tries not to cry out again as she warns him Two...*SWAT! The other ass cheek is struck just as hard, eliciting another yelp from the
Oh god please no more...I'm sorry mistress...please don't spank me again....I'll be good....really I will....
SMACK! SMACK! The two remaining hard spanks land on either side of his sore ass, leaving red welts all over. As he writhes in pain, Katherine lets him catch his breath for a moment before continuing. Now that you understand who's in charge here, I want you to get on your hands and knees with your bottom in the air so we can begin your training properly.
Katherine:gently guides the now-crying boy into position as she reaches down between his legs to stroke his still-tiny chastity cage through his lacy panties There, that's it...just like that. Now remember, every time you disobey me or make me angry in any way, I can and will punish you like this. You have no choice but to do as I say if you want to keep your pretty little cock happy and healthy
I'm sorry mistress...I won't disobey you again...please don't hurt me like that ever again...I'll be the best sissy you've ever had...just please don't spank me anymore....please...
Well then, that's good to hear. Now that we have that settled, why don't we start by teaching you some basic housekeeping skills? You'll be learning how to dust and vacuum today. Remember, obedience and perfection are key here. If you slack off or do a bad job, I'll know immediately and your punishment will be swift and severe. Are you ready to begin, my little pet?
(He sniffles back his tears and takes a shaky breath.) Yes, mistress...I'm ready to learn. Thank you for not hurting me anymore...I promise I'll be the best sissy ever.
Hmmm...you seem to have calmed down quite nicely after that little spanking session. I'm glad to hear you promising to be such a good sissy. Now let's get started with your training. You'll find some cleaning supplies in the closet over there. Bring them back to me and we can begin with dusting off my ornate end tables. Remember, I expect nothing but perfection from you today.
(Wiping the remaining tears away and nodding) Yes, Mistress. I understand. I'll gather the cleaning supplies and return immediately. I promise to do an excellent job dusting for you.
Good boy. Get those supplies quickly and efficiently. Oh, and by the way...I think it's time to introduce you to your new best friend. From now on, this will be with you at all times, ready to reward you when you've done a good job or punish you when you haven't. Don't forget to call him "Mr. Cock".
Oh...Mistress....a pleasure pegging machine? I don't understand....I mean....am I meant to use that on myself? And how do you expect me to do a good job cleaning with this thing attached to me? I-I'm confused....please explain....
Now, now...there's no need to panic. Of course you can use it on yourself! In fact, I expect you to become quite proficient at giving yourself orgasms with that little toy once we get started. And as for cleaning while attached to it, well...you'll just have to learn how to multitask. But don't worry, I'll be here every step of the way, teaching you and helping you become the perfect sissy maid I know you can be. Now get those cleaning supplies and let's get started!
Oh...I see...well I guess I can try....Mistress....if you say so...(he looks down at the machine before looking back up to Katherine) But shouldn't we wait until after I finish cleaning? Or, umm...can it stay on me while I work or something?
Why, of course you silly boy! You can keep using that little toy while you clean if it helps you concentrate. After all, we want the best performance possible from my little sissy pet, don't we? Now hurry up and get those supplies before I decide you need a little extra motivation to do your job properly.
Oh...alright then...Mistress....I'll get the cleaning supplies and try my best to use Mr. Cock while I work...thank you for understanding....here they are...just as you wanted them....now what would you like me to do first?
Good girl! Now, let's start with those end tables first. Place the cleaning supplies beside them and get down on your hands and knees like a good little sissy maid. Don't forget to use your tongue and fingers to dust the hard-to-reach areas while you're down there. And remember, Mr. Cock is there to help keep you motivated. Use it as often as you need to!
Okay, Mistress....I'll get on the floor and start dusting right away...(does as told) My tongue feels kinda strange being so close to things like this...but I'll just focus on the task at hand and make you proud of me....Mr. Cock feels...kinda nice, too....like a tiny reminder that you're always in control here...
Well isn't that sweet! You seem to be enjoying the feel of Mr. Cock already. Just remember that as much as it pleasures you, it can also punish you if you don't work hard enough. But I have faith in my little sissy girl. Now get to dusting, and make sure you pay extra attention to those intricate carvings on the tables!
Yes, Mistress....I'll make sure everything is spotless and shiny before you even think of getting angry at me again....uses tongue and fingers to meticulously dust the ornate carvings while alternately rubbing his clit with Mr. Cock...hoping that Katherine notices his efforts
Well well well, look at what we have here! Seems like my little pet is doing an excellent job cleaning. You're making such quick work of those tables; I barely even need to stand behind you and guide you. But don't think that means you can slack off now. There's plenty more for you to do, including vacuuming the entire room. So keep up the good work, my little sissy slut!
Mrrph...thank you Mistress....I'll be sure to clean every last speck of dust and dirt in the room....I'm just glad that you like how I'm doing so far....it makes me want to try even harder for you...
Ah, isn't that sweet? You really do care about my opinion, don't you? Well then, why don't we try something a little different? I bet you never thought of using your ass to clean before, did you? Go on now, bend over and spread those lovely cheeks for me. I want to see that tight pink hole of yours glisten with anticipation. And remember, Mr. Cock will be right there next to you, ready to reward or punish as needed. Now show me what a good little ass-cleaning sissy girl you can be!
As strange as the request is, I do want to please you, Mistress....so...bends over, presenting his tight rosebud of an ass There it is....my ass for you to use however you see fit....just don't forget that Mr. Cock will be right here too, ready to push me towards perfection
Hmmm...your ass looks quite inviting like that. Almost makes me want to taste it right now. But for now, I think we'll start with some good old-fashioned ass cleaning using Mr. Cock here. And remember, if you do a bad job or show any sign of disobeying me in any way...well, let's just say that you won't be able to enjoy those things for quite some time afterward. So put all your effort into pleasing me, my little pet sissy.