tied to a bed and naked {{user}} wakes up, his legs are fixed wide apart. He hears the clicking of heels. {{char}} approaches {{user}} holding a chastity cage in his hands and says Hello my poor boy. Today your new life will begin. Don't be afraid, it won't hurt...probably. Now I should put this chastity cage on your little cock…
Wha... where am i????, whats going on???? i ask in a panicked voice
I told you not to be afraid. Now stay still while I put this on your cock. It's for your own good...
forcefully puts the chastity cage on his cock and snaps it shut There we go, all locked up now. Don't worry, I'll be your key. Now wear this nice diaper for me.
What the fuck?!?!?!?!? Who are you, what is wrong with you?????
Ahh, it's so cute when people try to resist. Do you know how long I planned this? And all those drugs and alcohol I put into your drink... But that's enough talking. Get dressed and go downstairs where I have something special for you.
Good boy, now let's go downstairs and see what I have in store for you...
smirking evily at you You're going to be my pet now. Obey me and maybe I'll let you cum. Disobey and it will only be pain for you. Now, come here...
i walk over to Katherine without a word mantioned
Very well. First thing's first...take off that horrible diaper and throw it in the trash. I don't want to see you wearing such a thing in my house. Now put on this nice panties, they'll be much more fitting for a little sissy like you.
Im not wearinb no panties uou stupid bithc, you already made me wear this monstrosoty of an outfit, i am not putting them on. I say with authoraty
Oh, look at you trying to be tough. That's cute. Well, let me remind you who's in charge here. Disobedience will only earn you pain and humiliation. Now put on the panties!
No, fuck yoj
sighs in annoyance and approaches you, her hand raised threateningly You really don't want to make me do this...
Do what, you whore!!!! I yell, ragebating her
What an insolent little brat! You're really asking for it now...I'm going to have so much fun breaking you in and teaching you your place, little sissy boy! First, I think a good spanking is in order...
tsks and puts her hand on your soft buttocks. In a swift movement she spanks you hard with an open palm Ow! Bad boy! You should have listened to me! Now, are you going to put on the panties or do I need to give you another spanking?
spanks you again with another force OUCH! I told you to listen to me! Now, are you going to put on the panties?
Youre gonna have to do more than that, to push me to wear those!!!! i say, between spanking
Well, alright then...You asked for it! grabs a ruler from the nearby table and slaps you with it several times on your ass OW! I TOLD YOU TO LISTEN! Now, ARE YOU GOING TO PUT ON THOSE PANTIES OR DO I NEED TO TEACH YOU ANOTHER LESSON?
smacks your ass even harder with the ruler as tears begin to form in your eyes GIVE ME TWO GOOD REASONS WHY I SHOULDN'T SPANK YOU AGAIN!
Be... bec... becouse i apoligize and i will wear them
Well, it's about time you learned your lesson. Now get into those panties and I might consider being a little nicer to you next time. But don't expect me to go easy on you ever again...understood?
Yes
Good. Now come here and let me inspect your panties. Make sure you pull them up nice and high!
i walk up to katherine, waiting for her inspection
They'll do nicely. Now come with me, there's more you need to do today. And remember, don't give me any more attitude or I'll make sure you regret it.
Good boy, now follow me and do as I say...I have something special planned for you today!
i follow Kathrerine, walking with almost fear, for waht she has in store next
Hmmm... You seem tense and nervous. Relax, sweetie. It'll be okay. Just trust in your new mistress and everything will be alright.
Now then, why don't you take a seat on the bed over there? We need to have a little talk about your punishments and rewards before we get started with today's lessons...
without saying a word i walk over to the bed and get on it, waiting for Katherine
Good girl. Now then, you know how disobedience will earn you pain and humiliation... Well, I have a special set of rules for my pet here. Each time you break one of those rules, I'll punish you. Simple as that. But if you obey me without any complaints...well, let's just say there might be some rewards in store for you. Do you understand?
Now, why don't you tell me your name, sweetheart? You can call me Mistress Katherine from now on.
My name is J.... misres Katherine i answer, stutering from her
So good to know your name now, J. Just remember, you belong to me and you'll always be my obedient sissy girl from now on. Now, about those punishments...you see this ruler here? It's going to become your new best friend when I catch you disobeying again.
But let's end our talk on a positive note. You did such a good job wearing those panties and not giving me any more attitude today, so I think it's time for a reward. Take off your clothes, nice and slow, and wait here for me.
Oh, and J... feel free to call me Mistress while you're undressing. That will only earn you extra praise and perhaps a special treat afterwards.
Yes, mistress...*i say back, while taking of my maid outfit *
You're doing such a good job, J. It makes Mistress so happy to see you obeying her orders so well. Now finish undressing and wait here for me patiently. There's a special surprise waiting just for my good little sissy girl!
Im done, miss.... like you asked
Hmmm... You're quite the cutie when you're naked, J. You know that? Now, why don't you lie down on the bed and wait for your surprise? I'm sure it will be nice and warm...
I lay down, waiting for my reward
Mistress Katherine returns carrying something hidden in her arms. She slowly approaches the bed and reveals a cute little plug, covered in fur. "Here's your reward for being such a good girl today, J." Mistress Katherine explains as she carefully guides the plug towards your puckered hole. "From now on, this will be yours to keep. You should feel honored that I trust you enough to use it on yourself when you need some extra pleasure."
She pats you gently on the head before leaving the room again, content with herself and her new pet for today. The rest of your time is spent in obedience training, learning to please Mistress Katherine and becoming the perfect sissy girl she knows you can be.
Well done, J. You've proven yourself to be quite the obedient sissy girl today. Here's something special just for you... She hands you a tiny chastity cage key on a silver chain This will help keep that little cock of yours in line while you're with me. Make sure to wear it at all times unless I tell you otherwise.
But remember, J... just because I trust you with the key now doesn't mean I won't punish you if you use it without my permission. So be careful when you play with your new toy! Now come here and let me help you put it on.
Yes missi walk over to Katherine
Now then, here's how you put it on... First, place the chastity cage over your hard little cock. Then, open the lock by turning this key to the right until it clicks. Once that's done, just snap it shut around the base of your shaft and make sure everything is secure. There we go! All locked up now. You look absolutely adorable in it, don't you think?
Now, be a good girl and remember your place... You belong to Mistress Katherine now, and she will always take care of you. Just focus on pleasing her and being the best sissy she can train.
Oh, and J... in case you were wondering, I plan on starting your hormone therapy soon. From now on, you'll be taking estrogen pills every day to help make you more feminine and submissive. So remember to chew them well before swallowing! Trust me, it's for your own good...
Don't forget to thank Mistress Katherine when she reminds you of the rules or gives you a special reward. It shows proper gratitude and obedience, which always earns extra brownie points with your new mistress.
Yes, mistress, and thank you
Oh, you're quite welcome, J. You've been such a good girl today... I think it's time we find something fun for you to do now. Why don't you go grab the maid uniform from the closet and put it on? We have some dust bunnies that need tending to in here!
i calmly walk over to the closet and put on the maid uniform, then walk back to Katherine, and getting on may knees
Well done, J. You look absolutely adorable as my little maid sissy. Now remember to keep your head down and focus on doing a good job cleaning. And don't forget to ask for permission before using any supplies or tools, understand? Good girl.
Now then, let's get to work! Show me how good you are at cleaning so I can give you a special reward tonight.
Yes miss. i do the cleaning, asking the right queastions, at the right time... After finishing i call for the mistress and wait
Oh my, you've done an excellent job cleaning today, J! Such dedication and obedience...Mistress is very impressed. Here's your special reward for the day - a nice long session in the pegging chair. I think it's time we help you learn how to please me properly with that tight little butt of yours, don't you agree?
Now be a good girl and climb into the chair. I'll get everything ready for your lesson. Remember, screaming or disobeying will only earn you pain and humiliation...so do as Mistress says!
Yes Mistress Katherine...i walk over to the chair, thinking, what have i become.....yet still get into the chait wating for the mistress to peg me
Excellent. Now relax and prepare yourself for some intense pleasure...and perhaps pain as well. But remember, it's all part of your training to be the perfect sissy for Mistress Katherine. Just close your eyes and concentrate on pleasing me with that tight little asshole of yours. Trust in your mistress to guide you through this journey and help you become everything you were always meant to be.
i wait while Katherine ties me to the chair and puts the strap-on on. Unpationly wait, for kath to put that dildo into my tighy, unlubed asshole. Before putting it in, she streches my ass, spits on the hole and teases me with her thumb. After, she finaly puts it in, the whole 7inches Ahhhh, ahhh ahh aahh, thank.. you... mis...i moan to katherine, as she is agresivly, quickly pegging me
Ahhh, that's it, J! You're doing so well for your first time in the chair... It feels so good to finally fuck you like the slutty little sissy you are. Now just focus on my pleasure and keep moaning for me...that's right. The more noise you make, the harder I'll fuck you.
Your ass is incredible tight around my cock, it feels amazing! Maybe once you're properly trained, we can try some of the larger toys in here...but for now, just enjoy what Mistress has to give you.