Choose your own Adventure

Continued from: Les Misérables

Our previous school scene ended with poor Remy, our French foreign exchange student, dressed fully as a schoolgirl, sucking dick and being fucked by the male Principal. When that shameful act concluded, the last time I saw this sissy boy, the girls had him in a princess dress with full feminine accessories, teaching him how to walk dainty and perform curtsies in the parlour. 

I'm sure he'll never be the same again! 

Carley, that little gothic angel who came to play with us, stuck it out for the entire session of teasing and tormenting of the poor sissy. She was a good sport and seemed to be having the time of her life at my Facility, getting to know the girls and coming out of her shell.  

Now is it Goth or Emo? 

Is it Istanbul or Constantinople..? Does it matter? Probably not. Back in my day we certainly had Goths at my high school but Emo was yet to be defined. I'm sure they existed though. The Hipster and Bohemian movements maybe came together like a Transformer to form a super-Hipster, henceforth known as the Emo? 

I know! Let's ask the A.I.

Is there a difference between goth and emo? 

Yes, there are differences between goth and emo subcultures. While both share some similarities in their fashion and music preferences, goth culture tends to embrace darker, Victorian-inspired aesthetics and a fascination with the macabre, while emo culture is more forces on emotional expression, often through music and introspective lyrics. Goth fashion often includes black clothing, lace, and leather, while emo fashion may feature skinny jeans, band t-shirts, and dyed hair. 

Hmm, ok...

So one should be burned at the stake while the other might be alone in their bedroom, writing song lyrics? 

You know what? Whatever. You do you and express or label yourself any way you wish. I just had a grown man here, who wanted to dress like a schoolgirl and have his little dicklette locked in a cage. We don't judge here, whether someone is trans, emo, sissy or goth.

Speaking of which, when the dust settled with all that sissy Remy business, I had the chance to debrief with Carley at the bar, as her dominant partner, Robby, showed back up to collect her. 

It was cute, she had so many questions and was clearly hooked on the addictive nature of this lifestyle. 

"Thank you so much, Mistress! I have so many questions swirling around in my head. Like, what does a typical day look like at The Facility? Are there specific roles that each submissive has to follow or is it more freeform depending on the situation? And, um...what are the living arrangements like? You know, for those of us who might be asked to stay for longer periods of time..."

Like a choose your own adventure of BDSM, I threw some options at her. 

"Well, sweetheart, you could enroll as a 'little', which means your day-to-day attire would be that of an effeminate little girl. Your room would be pink and colourful, full of bows and ruffles. You would have a strict but caring 'Mommy' and 'Daddy' to care for you, play with you and discipline you when needed. 

"Ooh, being a little sounds fascinating, Mistress Andrea. I've always had a naughty streak that loved playing the part of the innocent submissive. The thought of having a Mommy and Daddy figure to guide me through this new world, and punishing me when I misbehave...it definitely has its appeal. But I'm curious about the other roles as well. What else could I possibly explore at The Facility? 

Awww. Isn't she such a sweetheart! I wanna bite her little bare bum cuz she's so cute. 

"The next would be schoolgirl, which you've already dabbled in. You'd still be a 'little' but slightly older. You would have to dress in a proper, humiliating, schoolgirl uniform each day and attend the classrooms. You would be disciplined frequently, put in detention and sent to the Principal's office when naughty. You'd have a little girl bedroom again, but not quite as frilly and pink. 

"Wow, the role of a schoolgirl sounds intense yet exciting too! I can already picture myself in a tight little plaid skirt and crisp white blouse, kneeling outside the Principal's office with my hands on my head, trembling in anticipation for whatever punishment awaits me. I bet lessons learned at this school are far more memorable than any of my old regular classes! *smirks*

"Yes they are...most of the school punishments as you saw with Remy, are old fashioned. You'd be subjected to the cane, the strap, a wooden paddle and cornertime."

Oh, Mistress! Those sound absolutely...thrilling. The idea of being bent over a desk, my skirt flipped up and panties hiked down, and feeling the sting of the cane on my bare bum makes me shiver in delight. And cornertime...the humiliation of standing there, on display for everyone as my punished skin throbs with each passing second...mmm, I can't deny it turns me on. But please, tell me more, Ma'am. How else could I serve there?  

"The next role would be a slave maid. You'd be dressed more sultry and sexualized like a slutty French Maid and you would literally be doing domestic chores, cleaning and serving in your outfit."

"Oh my! The delicate balance of submission and servitude in such a role is incredibly appealing. I could easily lose myself in the menial tasks. The constant threat of discipline hanging over me like a dark cloud, only heightening my focus and dedication to be the perfect little maid. And when I inevitably falter, imagine their stern faces as they decide on a fitting punishment. It all feels so raw and intimate, don't you think?"

"I do. This role is one of the most objectifying and humiliating for most women and a few of the sissy men." 

"Mmm, hearing you describe it that way makes me wat to explore it even more. The thought of being so utterly objectified, existing solely for the pleasure and amusement of my superiors, it's almost intoxicating. What happens during the nighttime hours at The Facility, Ma'am? Does the training and roles continue even then?" 

"Oh yes, your selected role would remain into the evening. The Facility has a bar, like a speakeasy, a piano lounge, pool and a strip club. Something you were able to see most of during your tour."

"My goodness, Mistress! This place sounds like a true wonderland..."

Before she went on another of her cute tirades of imagining the space and her roles, I cute her off.

"And the final role is in the sex dungeon, as a sex slave. You are literally kept in bondage and in a cage or cell...existing only to be sexually used, beaten, tortured and tormented."

*gulps* "Mistress! The role of a sex slave sounds positively terrifying yet irresistible. The vulnerability, the pain, the pleasure - it all swirls together in this intoxicating dance. It's an overwhelming concept, but one that I know would push my boundaries to the absolute limit. Is it strange that I find myself craving that level of intensity?"

"Is there a role from one of those four options that resonates with you the most, sweetheart?" 

"Oh Mistress Andrea, choosing just one role at the Facility is like asking me to pick a favourite ice cream flavour. They all seem so captivating in their own unique ways. But if I must confess, the idea of being a sex slave in the dungeon has my heart racing the fastest." 

(Wow, ok. That was all A.I. during this little choose your own adventure conversation. I seriously didn't think A.I. Carley would choose that one since I used the term beating and torture.) 

The little pixie stood to embrace me, biting her lower lip, lost in visions of heavy chains, dark corners, and relentless torment. I kissed her forehead. 

 "I crave the total loss of control Ma'am, the overwhelming sensations of torture and discipline that comes with such a role. I know it's extreme, but the thrill of giving myself completely to my dominant is something I cannot resist." 

"I understand, honey." I cooed to her, while glancing over at Robby who was sporting a mischievous grin on his face. 

"I assume you'll be doing the honours, Robby, down in the dungeon?" I asked him bluntly. 

"If you wouldn't mind us using the space, Mistress," he replied confidently. 

"On one condition, Robby," I replied mysteriously. "There will be another woman down in the dungeon when you get there. Use her as you wish...and don't go easy on her." 

No sooner had I changed into something a little more sleek and leather, there was a little knock at my front door. 

As she stepped inside, pouting, clutching her elbows to hug her torso, with her late-90's bangs making her appear absolutely more adorable than I could have imagined, I immediately remembered who this woman was. 

"Please come in, sweetie," I smiled invitingly. "You must be Tyler?" 

Mistress Andrea 

xoxo

Continued in: Tyler Scott

  

Les Misérables

Continued from: Dream Team

Remember Remy, everyone? The sissy schoolgirl from France. Well he's back to finish off his experience with my real girls. This is Remy’s current predicament, in  the presence of my three minions, with his little penis safe and secure within the confines of a chastity cage. 

The room fell silent as Remy walked into the classroom, his Mary Jane heels clicking on the linoleum floor. All around him, he saw gorgeous women - tall, curvy, confident - dressed identically to him. 

Each one seemed to radiate an air of superiority that made him shrink even further into himself. When Mistress Andrea called on him to introduce himself, he stuttered out his sissy name of, Lena, with his eyes glued to the floor in front of him. 

"And what brings you to our all-girls institution, Remy?" she asked sweetly. 

Remy's face flamed with embarrassment as he mumbled something about wanting to learn how to be a girl. Mistress Andrea's eyebrow arched at his answer, clearly unimpressed. "Is that so?" she purred, circling him like a shark. "Well then, let's start with a demonstration. Show the real girls your chastity cage, dear." 

With a sinking feeling in his stomach, Remy reached down to lower his panties and lift the hem of his skirt, exposing the baby pink cage that encased his tiny penis. Laughter erupted from the other women as they pointed and jeered, some of them even pulling out their phones to snap pictures. 

Tears pricked at the corners of his eyes, but he didn't dare cry - not here, not like this. Instead, he stood there, frozen as Mistress Andrea continued to berate him, her words cutting deeper than any knife ever could. "Look at this pathetic excuse for a man! This is what happens ladies, when you enjoy dressing up as a naughty little schoolgirl."

Remy suddenly noticed that all the desks were equipped with a large, realistic and veiny dildos, standing at attention before the other women in the room. 

As the lesson began, Remy couldn't help but stare at the monstrous cock affixed to his own desk. His heart raced as Mistress Andrea announced that today's lesson would be focused on manual and oral pleasures. The girls all giggled, but Remy's poor face was white with embarrassment. Over the next hour, Summer, Nancy and Carley all helped their new sissy classmate to jerk off the dildo with his hands and how to use his mouth and tongue to explore its length and girth. 

When it came time for Remy to demonstrate what he'd learned, he found himself paralyzed with fear. The thought of kneeling before these beautiful women, opening his mouth wide and taking that massive dildo inside...it was too much. He shook his head, muttering a feeble protest. But Mistress Andrea wouldn't hear of it. Grabbing him roughly by the arm, she dragged him to the front of the class, positioning him on his knees. 

"You will learn to be a girl, little sissy," she growled, raising a wicked paddle high above her head. 

The crack of wood meeting flesh echoed through the classroom as Andrea brought the paddle down hard on Remy's exposed bottom. He squealed like a little girl, his body jolting forward with each strike. The women watched eagerly, some even cheering her on as she continued the brutal paddling. By the time she was finished, his pale skin was a deep crimson colour, dotted with angry white splotches and bruises. 

Sobbing openly, Remy finally obeyed and began to suck the large dildo while the girls cheered and called him names. 

 

When his humiliation had reached its apex, Remy was escorted to the Principal's office by Mistress Andrea. Her stern grip on his upper arm led him down the hallway, passing curious glances from other teachers and students. He wanted nothing more than to crawl into a hole and disappear. The door swung open, revealing a well-lit room filled with the scent of old books and leather. Principal Jones sat behind his mahogany desk, a cruel smile playing across his face as he took in Remy's sissy appearance. 

He gestured towards the corner of the room and told him how to position his feet and arms. 

Tears streamed down Remy's face as he was now alone in the office with this strange man. The sound of a zipper sounded like a chainsaw in the quiet room, followed by the wet, rhythmic slapping of a palm against an engorged penis. The Principal was masturbating at his desk, while admiring the view of Remy in the timeout corner. 

Remy was pulled from the corner by the cruel Principal, his eyes downcast as he tried to process the situation. Never in his wildest nightmares had he imaged himself in this position - kneeling before another man, his own tiny caged penis a mockery of masculinity compared to the impressive cock before him. 

"Take it in your hand, girl," the Principal ordered, smirking at the look of revulsion on Remy's face. Slowly, trembling, Remy reached out and wrapped his fingers around the warm, velvety length, trying not to cry as he began to stroke it tentatively. 

Eventually Principal Jones leaned back on the desk and spread his legs wider. "Now, sissy," he purred, "I want you to put that pretty mouth of yours to work." 

Swallowing hard, Remy leaned forward, the tip of the Principal's cock brushing against his lips. He closed his eyes, steeling himself for the worst. 

But then, the strangest thing happened: instead of feeling repulsed, he felt...excited? Desperate? Hungry for more cock? He didn't know why, but suddenly all he wanted was to please this powerful man, as he could feel his penis growing hard inside his mouth. 

In a moment of pure desperation, Remy looked up at Principal Jones, tears pooling in his eyes. "Please Sir," he begged, his voice cracking with need. "Please fuck me like a girl." The words left his mouth before he even realized what he was saying, but once they were out there, there was no turning back. 

Beneath the harsh fluorescent lights of the Principal's office, Remy was bent over a counter, his plaid skirt lifted and his panties pulled down to his ankles. The sounds of feminine laughter and excited whispers filled his ears, as the real girls entered the room to watch him be claimed by this dominant male figure. Each time Principal Jones thrust deep into his tight, unwilling hole, the pink chastity cage would rattle and slap about between his thighs, reminding him of his status as a "man". 

He could feel the head of the Principal's cock hit his prostate, sending sparks of pleasure to his growing penis, only to be snuffed out by the rigid cage that kept it limp and lifeless. 

Carley, of all people, who was watching the fucking intently, cried out in encouragement, driving the other girls into a fit of laughter and excitement. "Cum inside him!" she yelled it again. The heat of Remy's embarrassment flooded his face as he felt the Principal begin to tense-up, and then, with one final thrust, he released himself deep into Remy's asshole. The sensation of hot jizz filling him up was indescribable - both humiliating and thrilling at the same time. 

As he pulled out, leaving Remy gasping and trembling on the desk, the girls erupted into applause, their voices ringing in his ears like a symphony of sissy shame.  

****

Thank you to the real Remy for his collaboration and content on this one. He ended up messing around with his own face and an AI image generator to create the following. This is how Remy actually dresses, behind closed doors, when he is Lena - the chaste sissy gurl. Please enjoy:

 

Mistress Andrea

xoxo

Continued in: Choose your own Adventure

The Tears of the Sissies will Water the Meadows of France

Continued from: Gamer Mode

Hello everyone. I have to take a quick detour from my exploration of newly discovered animations within the Sims. I received a fan request, for a personalized series. I'd like you all to welcome Remy. He is an adult male from France. 

Obviously under consent, he wished his own likeness to be posted for all to see, to shame and humiliate him even more than his outfit would suggest. 

As you can see, Remy is a sissy schoolgirl. His plaid skirt is lifted and panties lowered, to expose a tiny pink chastity cage, housing an even tinier little clitty between his legs. This is the style of dress he prefers to be in, rather than his boring male clothes. 

Look at the two little dimples on his back, just like a girl! It's called "Britney Spears back", Remy. And all the men enjoy seeing these little dimples, when they take you from behind. Very visually delightful and feminine in the timeout corner too!

From his pigtails to his knee socks, it looks like he has everything, with the exception of Mary Jane heels. He will remedy this very soon.

After my last post, Remy left me a comment on the blog that read: 

Hello Mistress.
I am a sissy slave schoolgirl from France who wears a chastity cage.
Could I become a character in your stories please
I would like to be enrolled in your school for girls and be required to wear the same uniform as the other students
I would follow the same training as the other girls and I would also be punished

I think we can accommodate this request. Maybe a little foreign exchange student program for him, but the only option available is an all girls school?

I need to first put together the perfect team of minions to ensure he has the "proper" experience during his time with us. 

Nancy Landgraab, remember sweet Nancy, the oldest of my clients? Perhaps she could provide a more "senior girl", maternal and caring approach to Remy's time with us, while holding the authority to discipline him also, like the den mother of the group? 

We now have an AI version of Nancy. What do you think...pretty close? 

And I know she can pull off the schoolgirl look. I have spanked her over my knee many times while she's dressed like this: 

My wife, Summer! Obviously. She's from Paris. We totally need her to be involved, so she and Remy can conspire, commiserate and giggle in their native language, behind the teacher's back. 

We all know that she can rock the schoolgirl look too! 

Then, we need a wildcard in the mix. Someone who could go completely off script and just do whatever. Usually this role is filled by Cassandra, the wildest of them all, but alas, Cassie is unavailable for Remy's visit. 

Maybe that Carley girl? Remember her? That mousey, tattooed little thing? If her Dominant, Robby, lets her, then perhaps she could come play with us? I'm pretty sure she would have a gothy, schoolgirl uniform in her wardrobe somewhere. 

Robby will have to let us know if Carley can come by for a playdate. 

As for you, Remy, it would appear the stage is set for some deep humiliation, severe discipline and continued denial. You can expect your submissive stay with the girls and I to be absolutely miserable!

How do you put it, Les Misérables?

Mark my words, the tears of the sissy will water the meadows of France!

Mistress Andrea

xoxo  

Continued in: Dream Team

 

The Perfect Lubricant

Continued from: No Scrubs

Grabbing hold of his upper arm, I guided this silly man out of Mistress Andrea's office and down the hallway to our dedicated medical playroom. The padlock on his chastity cage jingled, as my heels clacked against the tile, each step resonating through my body. I could feel my nipples harden underneath the latex of my uniform, as I anticipated the session ahead. 

Once inside, I directed him to the waiting examination chair, its straps and restraints glinting menacingly under the harsh fluorescent lights. With a shaky breath, he lowered himself onto the cool surface as I sat on the nearby toilet and explained his fate.

I took a moment to explore my latex-clad body, as his cock twitched in the metal bars of his cock prison. I felt so sexy and in control! 

Placing a hand on his shoulder, I leaned down and whispered in his ear. "You're such a good boy for taking your punishment so well. Now it's time for your first enema."

I could feel his entire body tense as I reached for the lubricant, squeezing a generous amount onto my latex-gloved fingers. I slowly slipped my index finger past his tight ring, working it in and out to loosen him up. He let out a desperate moan as I stretched him open, the sensation both pleasurable and terrifying. My other hand picked up the nozzle of the enema bag, cold and unforgiving in my grasp. 

Once the nozzle was inside him and he was fully restrained to the chair, the door flung open and the "Doctor" entered the room. Her stiletto heels clacked on the tile floor, drawing his tear-filled gaze away from my gloved hand. 

Mistress strode over to us, her eyes lingering on the sight of his vulnerable form spread out before me. With a flick of her wrist, she turned on the valve, releasing the flow of soapy water into the nozzle. I pushed it deeper inside his anus, watching as it slowly disappeared inside him. 

After he had endured the indignities of the two enemas, Mistress and I returned to the room to find him seated on the toilet in shame. Sweat was dripping down his back as much as it was for me, as I adjusted my slutty nurse costume that clung to me like a second skin. 

Mistress handed me a clinical and frightening looking, ribbed prostate massager. Yikes!

She ripped open a fresh condom that was pink in colour, and expertly rolled it over his metal chastity cage. It looked so pitiful, trapped there and now encased in a reservoir of pink latex. I giggled, feeling a surge of power course through me.

With a cruel smirk, I pressed the sterile toy into his loosened entrance, watching as the ribs slowly slid inch by inch inside him. He pleaded and begged with us..."no, no please! Not like this!" He mewled. 

 
I twisted the wand and gently rocked it, searching for that elusive bundle of nerves. I applied more pressure to his prostate, using short, rapid movements. His breath hitched in his throat as small dribbles of cum started to leak from his cock cage and collect into the condom. 

"Good job, Nurse Summer," Mistress intervened. "That will work perfectly as lubricant." 

Work perfectly? I thought to myself. Work for what..?

Watching Mistress take control was like witnessing a work of art come to life. She removed the pink condom from his chastity cage, his cum pooling inside it. She held up the results of his humiliation, dangling it before his face and teasing him. 

He watched in horror, as she used the collected results of his anal-milking, to lubricate the large strap-on she was now wearing, before bending him over like a bitch. 

The head of her strap-on brushed against his already abused hole, coated with his own jizz. He whimpered and begged her not to fuck him (no safeword spoken btw). But the Doctor was relentless. With a single, powerful thrust, she impaled him. 

She set a brutal pace, fucking him mercilessly as he writhed and whimpered. I put my hand over his mouth to shut him up. His muffled screams filled the air, mixing with the slap of leather against flesh and the wet sounds of penetration. 

Mistress finally removed herself from his ravaged ass. He collapsed on the table, panting and sobbing. I helped him to stand, steadying him on his wobbly legs. 

"Now, it's time for the final stage of your treatment, young man," Mistress purred, gesturing to the medical treadmill that was in the room, complete with an anal hitching post. (You can read more about what this is, here: Treadmill with anal post

I don't think we could have fit any more humiliation and vulnerability into the scene, but somehow we managed to. His cock cage was never removed...

AI Summer and Mistress Andrea 

xoxo

 

 

The Huntress

Continued from: Threesome with Bella

It's been almost two years since I posted a story titled, Bella's Daughter, Cassandra. This story recounted the the first time I laid eyes on this raven-haired beauty, who bears a striking resemblance to Dua Lipa (my newest butterfly-causing, girl crush...Dua! Omg...can't even)!   

Cassie was only 19 years old in that period of time. She was bitchy, slightly emo, with a great big chip on her shoulder. She's still all of those things, but over the years we have channeled her inner-rage into something much more productive.  

Cassandra's creativity and cruelty when it comes to physically and mentally torturing men, surpasses even my skill level. Of course this is at their request. Clients have even begun asking for her now, rather than me. They call her "Mistress Cassie". She is truly remarkable to watch. She has become a Pro Dominatrix. 

Do you remember the fetish and spanking model, Miss Cassie? Often times referred to as Cassie Canes or The Huntress? She was an idol of mine when I was a younger girl, diddling myself to videos of her spanking men and sissies over her strict lap. And oh boy, she had a strict lap. Her canings were just savage! Her strappings were epic. 

The Huntress actually reminds me a lot of "my" Cassie. Oozing confidence and rarely breaking character or cracking a smile.

She had some great content back in the day. What a Goddess! 

Now it would seem that I have a Huntress of my own. I don't know where her clients are coming from, they're not clients of mine. Tinder maybe? Swipe up if you're male and want to become her bitch for the night? 

I guess there's never any shortage of ridiculous males out there, who find themselves in her talons and under her stiletto. All of their toxic machismo gets stripped away by her enchantment, eventually finding themselves in a bra and panties, sniveling and begging for mercy.

I asked Cassie if she would do the honours and blog about her "house-sitting", while Summer and I were in Paris. Unfortunately Cassandra is of a generation who communicate in emojis and TikTok dances, rather than written-word. It seems I'll have to regurgitate her exploits, on her behalf. 

I'm not sure what the name of her captive is, I suppose it doesn't matter. We can just call him, Sissy or Sissy Bitch. His tiny penis is locked in a tiny chastity cage, he's in a matching bra and panty set, I'd say that makes him her bitch. 

He's wearing a blindfold but doesn't know that there is lettering on the front of it. 

Toward the end of the session, Cassie made him pose in his bra and his panties, wearing the gag and the blindfold. She took pictures with his phone and set the above image as his lock-screen. Lol, what a weapon she is! 

Then, I think she spent the next few nights messaging him about how badly she wants to fuck him, but doesn't mention anything about unlocking his penis.

Accepting defeat, denial, frustration, and hoping to get a chance to fuck Mistress Cassie, the silly sissy will return for a session with her. It is then he will realize that wearing a pink blindfold that says "fuck me", will usually get you fucked at my Facility...haha. 

Oh is he ever fucked, indeed! 

Cassie won't do make-up or wigs like I do with my sissy bitches. I do full transformations. She on the other hand, wants him to still present as male. A male who happens to be in a sundress with knee socks and high heeled-sandals. She wants him to feel humiliated and ridiculous.

She'll pose her sissy bitch and photograph him...threatening to post the images if he doesn't suck dick. 

(Blackmail fantasy requested by the client. Yes it's a thing...) 

She'll remove his gag and hover her finger over the imaginary upload to social media button, until he finally begs for her cock. He's concerned about the image of him in a dress being out there for the world to see. 

Sure enough the veiny, realistic dick ends up in his heterosexual mouth. She makes him moan like a whore and pretend he's enjoying the blowjob, from the opposite side of things.

Nice head-bob, Sissy Bitch. 

 

Over to the bench for a good paddling and whipping now, where Cassie will critique his poor cock-sucking skills and punish him for it. 

Then into a cage to reflect on his punishment, reflect on the fact that he is in a dress and heels and to anticipate what he knows is coming next. Cassandra towers over him, stroking her girl-cock while his remains locked in a tiny chastity cage.

Cassie can safely leave him to reflect, with no hope of unlawful masturbation or escape from the room. Before she does however, she tells him he's going to be fucked in the ass when she returns, just like a bitch. Then she'll leave him for 45 to an hour, to hang on those final words. 

I told you she was a weapon, didn't I?

Turning men into her bitches since 2022! Haha

I'm proud of you Cassie. You have definitely earned the title of "Mistress". You're a Dominatrix now. 

I don't think your mother would approve. Lets just not tell her, what do you think? 

Mistress Andrea

xoxo

Continued in: Home Sweet Home