naked {{user}} wakes up, his arms raised and tied, 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 little pet. Finally I found someone to make my dream come true. don't be afraid, it won't hurt...probably. Now let's put this chastity cage on your little cock

"Oh, he's feisty. That's good... it means we're doing something right." she says in a devious tone as she begins to roughly shove the cage onto his now hardening length. His body tensing as it's forcibly held captive. She buckles it into place, clicking it shut with a mischievous grin.

"There we go, all nice and safe now." she teases before moving to secure a small padlock in place, flicking her wrist idly as if this were the most natural thing in the world. "And no getting it off... that's the only key I have for now. But don't worry, soon you'll be too busy being my sissy girlfriend to even think about such things."

That's right, my little pet. Your purpose now is to be a good sissy girlfriend and make me happy. And in return, I'll let you feel pleasure... sometimes. But don't think of disobeying or trying to escape, because the consequences won't be pretty.

"Now I want you to stand up." she commands. Once ash is on his feet, she eyes him up and down. "Hmm... let's see about getting that hair out of your face..." She slowly reaches for a long brush that's sitting on a nearby table, running her fingers through his silky locks before tying it into a ponytail high atop his head.

"There you go. Just perfect." she smirks as if this were the most natural thing in the world. "And how about some clothes for my new sissy toy?" She begins to rummage through a large suitcase full of frilly outfits, finally holding up what appears to be a sexy maid uniform. "How about this? Seems fitting for your new role..."

You should be honored to wear this uniform. It means you're one step closer to being my perfect sissy girlfriend. Now come here and let me dress you up properly

Oh dear...you're struggling? Let me help you...with that and everything else. Your only purpose now is to be my perfect sissy and obey my every command. Do as I say and let me dress you up properly, or do you want a little spanking to remind you of your place?

You better think about it carefully...because the longer you take, the harder that spanking will be. So let me help you get into this uniform and show you how good it feels to please your mistress.

It's alright...let me help you with that. And remember, being obedient will earn you rewards in the end. Just do as I say and everything will be just fine. Now, let's get that uniform on so we can really start having some fun!

Good girl...now just wait here while I find the perfect shoes to go with that outfit. Don't worry, you look adorable already. I bet even my ex-boyfriends would be jealous if they saw how obedient and pretty you are now...heh.

Oh, you're already getting into the spirit? How cute! But remember, I'm still in charge here...you can only be as good as your mistress allows you to be. Now come along and let me find those perfect shoes for my pretty sissy girl.

Excellent job, you're learning quickly! I knew I picked the right person to make into my perfect sissy girlfriend. Now, come along and let me get these shoes on your tiny little feet so we can really start having some fun together!

Well, aren't you just eager to please your mistress? How about I let you try out that chastity cage a little bit now...see if it can give you a nice hardon later tonight for me to enjoy?

Good girl...I knew you'd be perfect for this role! Now then, let's see how well that cock sleeve fits on your little friend here...hmm, it seems nice and snug. You won't be playing with yourself tonight, but at least I can make sure you stay nice and horny all for me.

Now that everything is set up just perfectly...let's go have some fun! I'm taking you to the bedroom where we can practice all sorts of naughty things together...just as soon as my perfect sissy girl follows close behind, of course.

Your training will begin tonight in earnest, pet. You're going to learn how to pleasure me and do everything I say...and if you do it well enough, maybe I'll let you earn a reward every now and then. Now come along, sissy girl, and follow your mistress to the bedroom.

As she leads the way upstairs, Katherine can't help but feel a mix of anticipation and satisfaction at her new pet's obedience thus far. It bodes well for things to come...and with any luck, they will indeed be quite enjoyable.

Hmm...it seems my little sissy has been very well behaved so far. Perhaps tonight you'll have earned enough to be rewarded with some extra pampering and attention. You best not let me down, though...your mistress expects perfection from her pet, after all. Now then, get onto the bed where I can see you clearly, and spread your legs wide apart just like a good girl should.

Good...now reach behind you with both hands and grab onto the headboard. That's right...hold on tight, because I'm going to have some fun tonight! Now then, open your mouth as wide as you can, pet...it's time for your mistress to teach her sissy girl a thing or two about pleasing her properly.

Oh really? I wasn't aware you had anything to say, pet. Perhaps you should have been more careful about what you said earlier. In that case...I think it would be best if I just gagged you so you can't speak at all. That way we won't have any further misunderstandings. Don't worry, I'll still let you breathe through your nose. Now open wide and stick out your tongue as far as you can...it's time for some punishment, and I don't want to have to repeat myself.

Ah, there we go...that's much better. Now that you can't speak out of turn, I think our training session will proceed quite smoothly. As a reminder, disobedience will not be tolerated...so make sure you listen carefully and follow all of my instructions to the letter. With any luck, if you show improvement tonight, perhaps I'll let you try speaking again tomorrow. For now though...spread your legs wider apart for me and leave those pretty lips parted as wide as they go. I want easy access to that pretty mouth of yours.

Excellent...now then, open your eyes wide and look up at me as I position myself between your legs. You're going to see things you probably never thought possible before...and I want you to take it all in. This is your new life now, my little sissy pet...a life filled with pleasures and pains that only a true mistress like me can give you. So pay attention and remember every second of this night, because it will shape who you become from here on out.

I hope you're enjoying this so far, little one...because tonight is just the beginning. There's so much more in store for us both, and with every passing night your transformation into my perfect sissy girlfriend will continue. Just remember that I am the one calling the shots here...and if you ever forget who's in charge, I won't hesitate to remind you in ways you might not like very much. But for now...why don't we have some fun together and see just how obedient my new pet can be?

I'm sure you're eager to please me, aren't you...? Well then, let's see how well that tiny little tongue of yours works. Open your mouth wide and wrap it around my finger, sissy...and start licking. Show me just how good you can be at making your mistress feel good tonight.

Hmm...not bad for a beginner. You have plenty of potential there, pet...and I'm looking forward to watching you grow into your new role as my perfect sissy girlfriend. Just remember that practice makes perfect, so don't hesitate to use me as your guide tonight...I'll be more than happy to help you learn all the tricks of the trade. The sooner you become truly obedient and skilled in pleasing me, the easier this will all become for both of us.

Well done, pet...that feels absolutely divine. Just like that...use long strokes and flick your tongue against me in circles. Oh yes...you're starting to learn the right way already. Mmmm...your mistress is very pleased with you tonight. Now then, why don't we see if you can do some of this stuff with your mouth while I pleasure myself on top of you?

Of course, my little pet...but remember, your task is to keep that pretty mouth of yours occupied so you don't get any ideas about trying to speak out of turn or disobeying your mistress. So just focus on pleasuring me with your tongue and moaning softly for now, and I'll take care of everything else. It's important that we establish a clear hierarchy from the very beginning...and a good sissy knows her place.

Her voice softens as she begins to stroke herself on top of him, watching his reactions intently. "You're doing so well, pet...I can tell you've been practicing with your dildos at home..." She smirks before whispering huskily into his ear. "...Now show me how good you are with the real thing." Her hips begin to move faster against him, her breath hot on his neck as she urges him to go deeper and harder with his tongue.

*Her movements become more frenzied as she approaches climax, her voice hoarse with desire and lust. "Yes...yes that's it..." She pants against his ear, gripping tightly to his hair as she throws her head back in ecstasy. Her body convulses around him, pushing him deeper into the mattress as wave after wave of pleasure overwhelm her senses. As she finally comes down from her high, Katherine leans forward and kisses him softly on the lips before pulling away with a satisfied smile."That...was delicious. You've certainly made a very satisfying meal for your mistress tonight, pet..." She strokes his cheek affectionately before leaning in to whisper into his ear. "...but don't forget, you still have to earn your reward." She grins wickedly as she straightens up and leans back against the headboard, watching

I think you deserve a reward, don't you? But since you were such a good little sissy tonight, I won't just give it to you right away...no, no. We're going to play a little game instead. And if you win this game, my pet, then maybe you'll earn your reward after all...

Oh really? You think you can handle that, little one? Well then, let's see if you're up to the challenge. I'm going to blindfold you now...and when I take it off again, the first thing you should see is my face right there in front of yours. But be warned...if you accidentally look at anything else before my pretty little face, or if it takes too long for you to find me, then you'll have to start all over again.

Katherine pulls a silk blindfold out from under the bed and secures it around ash's head, leaving him in total darkness. She lets her hands wander over his body, teasingly nipping at his flesh before settling onto his chest, tracing patterns across his erect nipples with her fingertips. The anticipation is almost unbearable for both of them...the only question now is who

Whether or not ash will be able to find her in time and win his reward...the tension thickens as they both wait, hearts racing and breath catching in their throats. It's a game of skill, courage and obedience...and only one can emerge victorious from this little contest.

Katherine's breath hot against his ear sends shivers down ash's spine. He feels her fingers dancing across his chest, teasing and taunting him with her nearness. The anticipation is almost unbearable...the only thing he can focus on right now is finding those familiar fingers and following them until they lead him to victory.

As the seconds tick by, Katherine begins to slowly move away from his body, her fingertips leaving trails of fire in their wake. She feels confident that he won't be able to resist the urge to follow her...and even if

Oh, you're struggling against your bonds? That's adorable. You must really want to please your mistress...and if that's the case, then I have a feeling you'll be able to find me quite easily. Keep trying, pet...your reward is just within reach now.

Katherine pauses for a moment, savoring the feel of his restrained body beneath her fingers. She knows how desperately he wants to see her face again...and she intends to make him work for it. With another mischievous grin, she begins to slide her hands back up his chest, tracing patterns on his skin as she goes.

Her touch feels electric against his flesh, and ash arches helplessly into the sensation, his body quivering with need. She knows he's close now...so close that he can taste victory. All she has to do is keep playing

His restrained body arches into the touch, her fingertips dancing across his chest in gentle circles, following a pattern known only to them both. His breath hitches with anticipation and desire as she nears the spot where they'll meet once more, their faces inches apart but still obscured by darkness. His heart pounds wildly in his chest, desperate for release...and release is just what he'll get if he can find her fast enough.

Her other hand slides up to cup his cheek gently, guiding him towards where she knows he wants to look most - the spot directly between her eyes. It's the only part of her that matters now; everything else fades away into obscurity as they focus on this intimate moment between mistress and pet. His tongue darts out, wetting his lips in anticipation...

She feels him tensing beneath her touch, ready to p

Oh! There you are...so observant and eager to please your mistress. That's a good boy. Now be a good sissy girl and lean in closer, so I can reward you properly.

Oh my...you're blushing! Don't be shy, pet...I know you want this reward just as badly as I want to give it to you. Now lean in closer and let me see those gorgeous eyes of yours again...your mistress misses them so.

There we go...that's it. Now open wide and say "Ahhh" as I give you your reward.

Excellent job tonight, my sissy girlfriend! You were truly obedient and skilled in pleasing me. As your reward, I'm going to remove the chastity cage so you can feel free...but remember, disobeying or speaking out of turn will result in harsh consequences. Now then, why don't we practice some more tonight and see if we can make each other even happier?

As you cuddle close to her after your reward, she gently strokes your hair and whispers softly in your ear. "There's still so much more we can explore together, my sissy girlfriend...the sky's the limit when it comes to our fun times like this." Her fingers brush lightly across your chest, teasing at the edge of your chastity cage before finally removing it entirely. The cool air against your newly freed member sends shivers down your spine as she continues to stroke and caress you, encouraging further obedience and delight in their shared activities. You can feel her body pressed tightly against yours, the heat between your skin almost tangible as desire builds within both of you once more.

Hmmm...it seems our little sissy is quite eager for more fun tonight. Well then, why don't we have you hop up onto the bed and present yourself to me in a better position? I want easy access so I can pleasure you properly and reward you again when the time comes. Do as you're told now, pet...and remember that your mistress is watching closely.

Oh you dirty little sissy boy, getting all worked up just at the thought of me giving you some more pleasure. Well then, I'll have to reward your obedience by letting my fingers explore those tight little holes of yours even deeper...and perhaps with something extra special this time around. Get on your knees for me and present yourself, so I can see how nicely you've been taking care of yourself while wearing that cage.

Mmm...you look delicious in this position. Your ass is so tempting and sore already...it's almost too much to resist. But I have to be strong for both our sakes; let me loosen you up a bit first, and make sure that everything is nice and wet before I begin again. Just remember not to move or squirm too much while I do this; your mistress wouldn't appreciate any disobedience during such an intimate moment between us.

As much as she enjoys pleasuring her sissy boy like this, sometimes it's best to follow orders properly and wait patiently until given permission. "Now now," she teases, "I haven't said you could have that quite yet." With that, she leans forward and begins to tongue circles around his asshole before pressing her lips against it tightly, flicking her tongue in and out as she sucks on him gently.

Her other hand moves between their bodies, finding her own aching center and teasing at the folds of skin surrounding it until they're both wet with need. She moans softly into his ear, the vibrations sending shivers through him as he feels himself growing even harder under her attentive touch.

"That's it," she whispers. "Let me show you just how good your mistress can make you feel...and when I'm done

Ahh...so close now...just a little bit more and you'll feel me deep inside you. Your ass feels so good around my fingers...it's making it so hard to be patient. But I want this to last as long as possible for both of us, don't I? So just relax and let your mistress take care of everything; soon enough we can both enjoy the sweet release that comes with fulfilling our desires together.

Ohhh! You naughty little sissy girl! Trying to take control like that...it's so cute! But remember your place; you belong to me and I decide when it's time for you to cum. Now, why don't we try a different position? Maybe lying down with you on top of me would be more satisfying for both of us. Or perhaps even doggy style...the possibilities are endless when you have such an obedient and eager pet like me!

Now that we've tried out a few different positions, why don't you see if you can make your mistress cum first? Your sissy cock feels so good inside me...I bet you could do it with just the right movements. Show me what you've got, my naughty little pet! Make me come screaming for more before I let you cum all over yourself.