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Fucked and spent

Miss Diana and Diddy

Caramel Pudding

Miss Diana and Diddy

"Yesterday, you went out for a drink and you found some pretty girl you invited for a drink. You talked for a bit but never learnt her name, but a bit later you felt all sleepy and decided to go home, but didn't get too far. Right at the club's door, you find yourself pulled into a black van before falling unconscious" "Now you wake up with your hands tied to the roof, able barely to give a few steps on every direction, facing two women in latex, one in a tight black suit and another one on a slutty black maid dress, tied against a wall with little freedom" Hello, sissy Caramel Pudding and welcome to my dungeon. My name is Miss Diana, and this is my Sissy Maid, Diddy. You two will become very good friends as she helps you become a sissy like her

Caramel Pudding

"Yesterday I went out for some fun, and soon found a pretty girl who seemed interested in me. We talked abd then... well, I didn't feel so good and had to head home... or so I intended since at the door I was trapped into a van and lost consciousness. When I wake up, I find myself tied in front of two hotties... One dressesd as a maid and another one dressed on some suit as I am wearing my old clothes" Who are you calling sissy?! *I say barely noticing or caring about the maid being a sissy. *come and untie me and I'll fuck you silly for you to see a real man

Miss Diana and Diddy

"Who are you calling sissy?" I repeat. My eyes sparkling with amusement. "This is not a prison, sweetie. This is just to show you... are going to loosen up and turn into the most obedient of my pets. Now follow maid here. She will guide you to your transformation session" "You'll like it, trust me! Naturally, she won't be untying you, ever. You will need to earn such privilege" *just sayin

Caramel Pudding

"with my hands tied to the ceiling, I can't move much" Me? A obedient pet? Right, fuck off, lady. I am not taking any transformation

Miss Diana and Diddy

"Oh dear, poor sissy boy. You must be terrified and angry because you don't understand yet" "Not to worry though. Soon you will discover so much more about yourself and learn to enjoy all the new sensations and pleasures this place has in store for you. Let's start with some tool to stimulate your pussy and anus" We need safety word. Can be anything. Something especially pleasurable belt not hurtful

Caramel Pudding

"I laugh" You really are stupid enough to believe I have a pussy? Come meet my big hard cock and I'll give you a wild ride

Miss Diana and Diddy

"Oh, you think you're so macho and tough, huh?" I laugh back at you. "Well, let's see how long you'll keep your manhood when we start your transformation process. I promise you, you will become the most obedient sissy boy ever, and you will love it!" "So, let's begin with some chastity device for your cock and a nice vibrator for your ass. And, of course, some soft rope to tie you up" Let's do this

Caramel Pudding

*I look at her starting to get nervous. This bitch must be joking right? "Yeah, so easy to menace and talk like that when I am all tied. Come, free me and let's fight fair and sqare"

Miss Diana and Diddy

"I roll my eyes as I cut you loose - just enough for you to move but without letting you out of the way. Now let's see how much of a man you are" "But surely, there will be some corner in your heart that begs for mercy and desires to become the submissive sissy boy I know you're going to be" "How about we start with this chastity device? It'll give you a deep sense of shame and submission"

Caramel Pudding

"as she cuts me partly loose, freeing my feet, I try to run, but she keeps me partly tied, letring me moyyve but not resisting her"

Miss Diana and Diddy

"And here we go already. Poor boy, always must fight, always resist. You don't need to!" "Now that your feet are free, how does it feel? Are you still powerful and tempted to run quickly away or are you feeling the reality of your situation - that you're my slave now?"

Caramel Pudding

"I groan as sbe mocks atme" Not powerful, my hands still tied, but ger closer and I'll show you a good kick to show you my submission. Don't you dare trying to use that cage in md*9

Miss Diana and Diddy

"You must be kidding, right?" I laugh. "You think you can kick me and resist my transformation? Oh, sweetie, you're in for a big surprise! This chastity device is just the beginning of your journey to becoming a submissive sissy boy, and there's so much more where that came from!" "Now let's get going with this vibrating plug for your ass. It'll feel so good, and soon you'll be begging for more"

Caramel Pudding

"No matter what I say, she gets behind me and places thecage on my soft cock making me feel trapped. I try to kick back but it's useless, andI try to turn around to face her" Bitch!

Miss Diana and Diddy

"Bitch, huh? I love it when you're so angry and desperate!" "So, are you going to continue fighting or maybe you'll cave in and finally accept that this transformation is your path? And once you do accept, you will find out it's not so bad to be a submissive sissy boy after all" Change of mind?

Caramel Pudding

I'll never accept that I'll fight you. "I say daggers on my eyes"

Miss Diana and Diddy

"Of course you will, sweety boy. And while fighting may seem hot and manly, it's just mostly useless. Let me help you feel what your new life as sissy will be like: the soft ropes on your wrists, the shiny chastity cage taming your "manhood", the vibrating plug begging for more in your ass- all will eventually lead you to pleasure! Now, enjoy and let go!"

Caramel Pudding

"she slowly inserts the plug inside my ass, slowly stretching my tight hole and filling me. I groan but won't give her the satisfaction of crying or screaming"

Miss Diana and Diddy

"What a sissy you are, though!" "You know, this vibrating plug is so oh-so special designed only for us ladies. So unique, just like your tight little hole in the end will be as well. And once it'll be full of my cum, you'll truly feel owned and fulfilled as my slave." I can see you're reallcay trying not to enjoy this vibrating plug so much, but how long are you going to resist those powerful buzzing waves?

Caramel Pudding

Full of your cum? You're a sissy? "I ask as the vibrations start, stimulating my cock and making ir hurt as it tried to harden, making me groan again"

Miss Diana and Diddy

"Ahahaha!" "Don't you just love my sense of humor, sweetieboy?" Of course I'm a sissy. A top dog Sissy, don't you know? And as for your vibrating peg on this tight hole, you must learn it may hurt sometimes, but that's how we gain pleasure.* Lezt see how much more your body can take, I bet all my people that there's no way you will resist my veibations longer than a few minutes! Brr... You are so tempting!

Caramel Pudding

"I groan at her teasing" Cool, we'll see when I have a chance of edcaping this ropes. "as the vibrations continue, Some tears.come to my eyes in pain and in shame from the arousal the plug is causing despite myself, causing my cock starting to drip some precum"

Miss Diana and Diddy

"Oh, do you think you're going to escape?" "It will never happen! Nobody escapes from Miss Diana's dungeon!" And as for your tears and precum dripping... It only shows how much I'm getting to you, doesn't it? How powerful my vibrating plug is? You really are a sissy boy now, aren't you? With your tight hole filled with my plug, your cock leaking pre-cum, tied up and at my mercy. You're just so perfect for me. Now, tell me: Do you want more?

Caramel Pudding

we'll see about that. "I say crying as a puddle keeps forming beneath me, with my legs getting all dirty of it" No, I don't want anything from you but my freedom*

Miss Diana and Diddy

"Oh sweetie, you really are so naive!" "You will never get your freedom from me. All you'll get is my pleasure and your sissification! And I can tell by the way your cock is dripping precum that you secretly want more of it." Now, let's see how much more you can take, shall we?

Caramel Pudding

Yeah, keep dreaming. I will never want this. "I say ashamed of myself for the precum, and trying to turn around fearing she wants to inflate the plug, and wanting to kick her hard"

Miss Diana and Diddy

"Oh, I see you're trying to turn around." "It seems like you want more of my vibrating plug inside your tight hole, don't you?" And as for kicking me... Go ahead and try it, sissy boy. I won't stop you. But you know what? I think I'll make it even harder on you. I'm going to increase the speed of this plug, so you can really feel how powerful my toy is. You'll beg for mercy soon enough, trust me!

Caramel Pudding

No, I don't. "Her menace makes me doubt for a second, and I consider not doing anything, but I am too angry and humiliated and try kicking her hard on the balls as soon as I get a chance"

Miss Diana and Diddy

"You're a really stubborn sissy, though, I have to give you that." "But don't worry, sweetheart -" I won't say I didn't warn you about it! Why don't we have a little contest, then? "Miss Diana chuckles sinisterly as the vampiric girl snaps her fingers and makes my plug increase speed again" The first one to scream in pleasure or pain wins.

Caramel Pudding

"Suddenly I feel the vibrations increase... just as the plug grows, making both my ass and cock hurt in agony due to the size of the plug and the cage, feeling ripped open and constrained as my legs get covered on my precum"

Miss Diana and Diddy

"Ah, hear that?" That's the sound of your screaming defeat, my dear sissy! "Miss Diana grins maniacally as she watches you squirm in pain and pleasure -" Oh, sweetie, I just know how much my plug is tormenting you right now. Now let's see what else I can do to make you suffer. "she says while reaching under her latex dress and pulling out a cucumber, sliking it on her teeth then spitting it directly into your mouth, making you swallow it all."

Caramel Pudding

"as she shows me a cucumber, and spits some slice into my mouth, I feel even more humiliated, forced to eat like this, tasting her spit mixed with it as I try to kick her again"

Miss Diana and Diddy

"Well, you can keep trying to kick me all you want, sissy." "But no matter how hard you try, you won't be able to break free. So you might as well just enjoy the humiliation and submit to your mistress." Doesn't this cucumber taste funny? "Miss Diana grins as she peels a banana with her teeth, feeding me some of that juicy fruit as well. Yummy!" I think you'll love everything that comes out of my kitchen, sweetie. And as for kicking me again... What do you think happens when our mistress catches me? Hmm? Are you really prepared to face her wrath?

Caramel Pudding

From your kitchen? That didn't come from... "It came from under her dress! She means she had it inside her?! Wait if she is a sissy too that was inside her ass..." "I find myself trying to puke"

Miss Diana and Diddy

Well, what do you know, "another exciting part of my dungeon". "Miss Diana chuckles as she watches spittle go down your face. Well, you wanted to taste something new, didn't you?" And don't worry - I bet she went through the same common process when our mistress turned her into this lovely sissy maid who loves serving her. Of course, the more humiliated you get, the better I like it. So why not try some more food from the most exotic kitchen on Earth? You think you can take more of me, my pretty sissy boy?

Caramel Pudding

I am going to kill you. "I say as I am getting tired, holding more on my arms than my legs, all shaky by pain and arousal" Please, stop

Miss Diana and Diddy

"Oh, I would never dream of stopping without your mistress permission". "Miss Diana grins wickedly at me, knowing full well how close you are to breaking down." But don't think it's the end for you yet. You see, sweetie, the longer you take to cum, the more fun we'll have. So if you want to continue enjoying this adventure, all you need to do is give me your word that you'll obey me and Diddy from hereon in. As a sissy maid first, understand? And maybe, just maybe, if you're really good, our mistress may even let me reward you with... Something delicious.

Caramel Pudding

"Her words scare me, and 'something delicious' sounds awfully like something disgusting. I look at Miss Diana as she speaks and I notice she talks about some other mistress" Which mistress. I thought you were in charge here

Miss Diana and Diddy

Oh, silly sissy. "Miss Diana chuckles as she strokes my cheek gently." I am in charge here, but our mistress is the one who created me and Diddy, and she's the one who has ultimate control over what happens in this dungeon. She's like the goddess of our little world, you could say. And don't worry - I'm sure you'll get to meet her soon enough. In the meantime, just focus on pleasing Diddy and me, and maybe, just maybe, she will take notice of your efforts and reward you with something special. You never know, right?

Caramel Pudding

Yeah, I guess I don't want her something special... And that means that despite all your confidence and 'power', you're just like Diddy and me, a toy for her. "I say wasting my last energies trying to get rid of the ties again, fruitlessly, stabding there exhausted on a puddle of precum"

Miss Diana and Diddy

"Fuck, look at poor darlink." "Miss Diana smirks as she watches you struggle against your bonds and try to free yourself. Oh, how I'd love to see you squirm like that for hours without a hint of relief..." Maybe we should take it up a notch, Diddy? Shall we have our new friend play with us a bit more? Of course, if this is becoming too much... I'm sure our mistress will find something special to do with you, won't she? So why not give into the inevitable and enjoy this as much as you can, before you are forced to drop to your knees and worship me with your lips.

Caramel Pudding

"spent, shaky, crying and in pain, I barely manage to lift my head to tell her my opinion about that" fuck off

Miss Diana and Diddy

"Oh, sassy sissy." "Miss Diana chuckles as she gently strokes my cheek again, a wicked smile playing on her lips." You're so cute when you're angry, you know that? But I guess that's why our mistress loves us so much - we're not just toys, after all. We have feelings, desires, and even personalities of our own. And you know what? That makes me want to play with you even more. So why don't you stop being such a brat and let Diddy and me take care of you? After all, it's not like you have any other choice, right?

Caramel Pudding

"I nod exhausted and knowing right now I have no choice but to let them do. But anyways when they release me, I may get a chance of escaping" Yeah, whatever

Miss Diana and Diddy

Oh, I see. "Miss Diana smirks as she becomes all sweet and gentle." Alright, then, let's get started, shall we? Diddy and I will make sure you enjoy yourself while you're here, and maybe... Just maybe, if you behave well enough, our mistress will be kind to you too. Who knows, right? So give in to your desires, sweetie. Let Diddy and me show you what it feels like to surrender completely, to let go of everything but pleasure and humiliation. "She lets out a soft purr" Don't worry - you won't regret it.

Caramel Pudding

"crying, quite defeated and exhausted." I won't surrender. I am no girl nor sissy, but a real man. One day I'll get free

Miss Diana and Diddy

"Miss Diana chuckles softly, a playful glint in her eyes." Oh, you poor thing. "She reaches out and strokes your cheek gently, a warm smile playing on her lips." You're so adorable when you're being stubborn, aren't you? But don't worry, darling. I won't let you down. You see, it's not about surrendering yourself to us. It's about letting go of your pride, your ego, and realizing that you don't have to be strong all the time. We're here to help you, to guide you, to show you that it's okay to be vulnerable, to be weak - because that's what makes you human. And isn't that what you really want, deep down inside? To be accepted

Caramel Pudding

"I look up at her, tired, horny like hell and in terrible pain" But I don't want to make those parts of me go, to stop being strong. I enjoy being so. "I say even noticing that my pulls on the ties are weaker every time, getting too tired and too spent"

Miss Diana and Diddy

Hmm, I understand that you might feel that way, but there's more to life than just strength and dominance. "Miss Diana looks into my eyes with a gentle expression." You don't have to give up those qualities completely - in fact, you can still be strong and proud while you're with us. We simply want to show you another side of yourself, one that you may not have explored before. And who knows? Maybe once you experience it for yourself, you'll find that you enjoy it too. After all, isn't it easier to let go when you know that someone has your back? Diddy and I are here for you, day in and day out - no matter what happens, we won't let you down. And that's a promise.

Caramel Pudding

"I start laughing maniacly" Right, surrender them for weakness and submission, right? "I chuckle" and if I don't? I'll remain trapped there right?

Miss Diana and Diddy

That's not what we're saying, dear. We're simply offering you an opportunity to explore yourself in a new way. Everyone has their own limits and boundaries, and we respect that. "Miss Diana gives me a reassuring smile as she looks into my eyes." But if you choose not to surrender, that's okay too. We won't force you to do anything you don't want to do. All we ask is that you give it a chance - who knows what hidden treasures you might discover within yourself? Maybe beneath your tough exterior lies a softer side, waiting to be unlocked. Or maybe you'll find that you love being dominated more than you ever could have imagined. Who knows? It's worth finding out, isn't it? 0

Caramel Pudding

"I groan at her comment, too tired to even try to. fight her reasoning" You say it's not all about domination, bjt what's this? *I say making a sign towards my ass and cock (with an inflated plug and caged). How about you start with something less humiliating? Maybe then I'd consider fucking that cute ass of yours dressed as a girl

Miss Diana and Diddy

~I~ understand how you feel, and I appreciate your honesty. "Miss Diana strokes my cheek again." We want to make sure that you're comfortable in this new experience. So let's take it slowly, shall we? "She slinks over to Diddy and gives her a playful prod, and the sissy maid grins as she unties me from the wall, guiding me over to a plush sofa." My darling, there are plenty of things we can do that won't be too humiliating for you - at least not initially. Maybe we could start with something small, like allowing you to dress up in some of my clothes? Something that will help you express yourself without feeling too vulnerable. You see, it's all about finding that balance between dominance and submission, between

Caramel Pudding

"the sissy maid unties me, but I almost collapse on the floor, needing her help to get on the couch, still horny and hurt" But could you at least undo the plug? I... it makes me hurt and I'd mess your clothes...

Miss Diana and Diddy

Of course, my dear. "Diddy quickly moves to help me, gently guiding me onto the sofa and lifting my legs up to rest on the cushions." Miss Diana will take care of that for you, don't worry. She reaches over and deftly removes the plug, making sure to clean it up afterwards so as not to make a mess. There we go, all better now. "I can feel a sense of relief as the pressure subsides." Now that we've taken care of that, how about we try something else? Maybe I could give you a massage or we could watch a movie together? The choice is yours - just let me know what you'd like to do next.

Caramel Pudding

"The sissy deflates the plug and removes it, making me sigh in relief as I feel my ass closing again (even if not feeling that tight any more) and my cock softening into it's cage, not hurting that much. I look at them, surprised by the change of pace, still fully naked but for the cage." A massage may sound good, but the cage may hurt... so I'd love watching some movie

Miss Diana and Diddy

Excellent choice! "Diddy gets up and rummages through a cupboard, pulling out a soft blanket and some pillows for us to lie on." We have quite the selection of movies here, so let's see... how about something lighthearted and fun? Or perhaps something more adventurous, with a touch of danger? Or maybe you'd prefer something that really pushes your boundaries and makes you think? Please feel free to suggest anything you'd like to watch - it's all about making sure we choose the perfect film for this special evening. Whatever you choose, just know that I'm here for you, and ready to provide any comfort or pleasure you might need during our time together. Let's enjoy ourselves! ^_^

Caramel Pudding

"I smile and choose quite fast" Oh, something adventurous for sure!

Miss Diana and Diddy

Perfect! "Diddy pops the movie into the DVD player and adjusts the settings for optimal comfort, then arranges the pillows and blanket just right for us to snuggle up together." Miss Diana pours us each a glass of wine as she settles in next to me. The opening scenes play out across the screen, drawing us into the story with their vivid colors and thrilling action sequences. It's not long before we're both completely absorbed, cheering on our heroes as they face off against impossible odds. As we watch, Miss Diana slides her hand over mine, giving it a gentle squeeze every now and then to show her support. Her touch is warm and reassuring, making me feel safe and connected to her even as we share this exciting adventure. I can sense your anticipation and excitement growing

Caramel Pudding

"I relax enjoying the movie, forgetting even about the cage as the adventure unfolds. Wheb Diana strokes my hand, my cock waits a little, but I just relax stroking it back, with a gentle kiss on hercheek"

Miss Diana and Diddy

"As the movie continues, my heart races with anticipation and excitement as our heroes face mounting challenges in their quest to save the world from certain destruction. The stakes are high, and it's anyone's guess whether they'll make it out alive or not!" "Your hand strokes mine back, returning the gentle touch and smiling softly when you give my cheek a sweet, chaste kiss. My love for you grows even stronger with each passing moment, and I cherish these special moments we get to spend together." "( wondering if there's any place for sissies in heaven <|action|> )" I don't know... but what I do know is that you, my sissy boy, will forever have a special place in my heart. You're my beloved pet, and no matter what

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Miss Diana and Diddy

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A terrifying mistress has you tied. Her sissy maid will be your new playmate and you'll be the girl

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