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

Dream Team

Continued from: The Tears of the Sissies will Water the Meadows of France

The day had arrived for Remy, the sissy boy from France, to join the girls and I for his fantasy session. I would be playing the role of the strict Schoolmarm. 

(Not sure what I'm doing with my hands in this one)

I arranged for one of my older, male, slightly creepy clients to play the role of the leering Principal in this all-girls school. Then, as I stated in the previous post, I put together my dream team of fellow students. Beautiful women who would like nothing more than to tease, humiliate and belittle poor Remy, as the new foreign exchange student. 

Check out my dream team: 

We have Summer.

The bubbly best friend who's skirt is not regulation length, just to drive the boys mental. 

Nancy. 

The more mature, senior schoolgirl who is the leader of this group and close assistant to the teacher. "Assistant" could be synonymous with tattle-tale. 

Finally, the new girl, Carley. 

The goth-girl, maybe the wild-child, believed to be unpredictable. This will be her first playdate at my Facility so I'm not sure what this little pixie is gonna do. She does look great in her uniform though. I can't wait to see what this little sniper is capable of.  

There was absolutely no fuckin' around when this French wiener arrived. I booked him in personally, dressed in my role and wielding a cane. He was booked in through the cellblock area so he could truly appreciate his impending peril. Every stich of his clothing was removed, right down to the little pink, clit cage that he wore to his session. 

This was my view as I towered over him. He was completely hairless below the eyebrows, he lacked muscle tone for a man, and his pathetic little thingy looked like so: 

Ick! We need to get that little clit hidden beneath some panties, forthwith! I seized control of the keys to his little clit cage and locked them away with his boring, boy clothes. 

When Remy originally booked this multi-day session, he wanted to be dressed like the other girls. But just to make things worse for him, I didn't do a full transformation with makeup or a wig. I wanted him to still look male, just to humiliate him further, in the presence of my beautiful girls. 

Appearing outwardly male for day one was my rule, but dressed like a schoolgirl. He will have to show me that he truly wants to be a girl. He will need to behave like one, sit like one and learn how to please men like one, before I'll continue his transformation beyond his mere attire alone. 

Which outfit should we go with? I had three options that fit him. 

Option A:

(Not a huge fan of the shorts, but you can see his locked up little clit-bulge in the front)

Option B:

(It's important that he be in high heels, as he clicks around the classroom)

Option C:

(Look how ridiculous he is, dressed like that!)

Once I get him dressed, he will feel sick to his stomach with humiliation. Then I'll finally present him before the girls and tell him to introduce himself as Lena, his sissy name. 

Poor Lena is going to be in for a long few days! She's already crying and I haven't even caned her yet. 

Stay tuned. 

Mistress Andrea 

xoxo

Continued in: Les Misérables

 

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

 

Tattoos and Tongues

Continued from: Meet Carley

I barley finished up my secret masturbation indulgence, brought on by listening to poor Carley receive a spanking, before there was a tiny little knock at my office door. 

I composed myself quickly, I'm sure my cheeks were a little flushed and my knees were definitely wobbly in my heels. 

"Enter," I called out. 

I was surprised to see Carley's mousey little face, peeking through the door she cracked open. 

"May I come in, Ma'am?" She squeaked out sheepishly, her eyes appearing recently moistened with tears. 

I held out my arms maternally, invitingly. This little fallen angel can't be any older than twenty-five, so I turned on the Mommy charm.  "You ok, sweetheart?"

"Yes Ma'am," she said, as she accepted my embrace and a comforting rub to her upper arms, while I smiled down at her. 

"Robby told me to come apologize to you, Ma'am. And to thank you for the use of your private space for m...my spanking, Ma'am." Swallowing her humility hard, Carley apologized and thanked me. 

Her voice trembled with vulnerability as she continued to speak. "If you need to take me over your knee for putting you out of your way, Ma'am, I understand." She began to lift her dress to reach for the band of her panties.

Awww! What a little cutie! I stopped her. 

"That won't be necessary, little one," I said caringly, as I continued to rub her shoulders. "Having to come here and apologize and thank me for providing a space for you to receive a spanking, I'm sure has served as punishment enough."

Simply being hospitable, I ushered her to sit. Stupid me! She just got a spanking. She did in-fact sit down beside me but she did so very gingerly. 

Her voice was laced with the awe and amazement of a small child at Disneyland. "Mistress, what IS this place?" 

I giggled momentarily, before answering her in as clever of a clandestine way I could manage.

"Have you ever been to a food court in a mall, sweetheart?" I asked her rhetorically. "It's kinda like that. There's a little something for everyone's different tastes." Carley smiled for the first time. 

With that, I took her by the hand and gave her a full tour of the place, from top to bottom. From the scents of leather and metal of the sex dungeon, to the comforting aroma of baby lotion in the nursery, I showed her everything. 

The sparkle in her eyes beamed in amazement like it was Christmas morning. Like she was an Elvis fan and this was her Graceland. 

"I can't believe this world exists, Ma'am." Carley gasped aloud, "It's making my tummy feel funny. Like it does when Robby tells me I'm getting a spanking." 

   

What an adorable little biscuit! I chuckled at her comment. "Speaking of which, where is Robby?

"He was at the bar, Ma'am, with that short-haired woman who kinda looks like me," she answered, sounding a bit irritated. 

"Oh gawd! He's met Cassandra..." My voice trailed off, almost feeling sorry for poor Robby. I'm sure when he settled into the bar he was greeted by a, "who the fuck are you?" 

Carley interjected, in her posh, little accent. "He thinks he's a bit of a Jack the Lad. He probably thinks she fancies him...."

"Cassandra?!" I blurted out. 

"Have you ever tried to call or summon a rattlesnake into your palm?" I sarcastically added. "That's about how much luck he's gonna have with Cassandra."

Our tour ended at the bar, and as I expected, there was Cassandra, glaring at Robby in disapproval, simply because he has a penis and it's not in a chastity cage.

Cassie's disgusted gaze upon Robby quickly flashed toward Carley, as we both power-clicked into the room. Her eyes lit right up when she saw the adorable and edgy little thing. A kindred spirit perhaps? Both adorned with piecing and tattoos.

Cassandra was on her like a hawk, pulling her in for a warm hug and innocently introducing herself as "Cassie the Receptionist", even though she is way more than that now! 

"You're fuckin' gorgeous! May I kiss you on the lips, Carley?" Cassandra blurted out, being obnoxiously vulgar and bold. 

Carley flashed a quick glance towards Robby, who raised an eyebrow and gave a nod of approval. 

Then, as he sipped his old fashioned, I watched a boyish grin tug at the corners of his lips, as he took in the sight of Carley returning the kiss, and dart her pierced tongue into Cassandra's mouth. 

"Is this little doll a client, Mistress?" Cassandra asked the room out loud. 

"No." I replied. 

"Not yet, anyway...."

Think we should have her back...? 

Mistress Andrea 

xoxo

Continued in: The Tears of the Sissies will Water the Meadows of France

Meet Carley

Continued from: Tara Gregory: Interview Continued

This story is a fan request from a bloke in the UK named, Robby. It involves his alluring and spicy Kindroid gal, Carley. Take a look at this little pistol! She happens to be his submissive, surprisingly. 

Don't judge a book by its cover I guess... 

Chip on her shoulder, brat...maybe some Daddy issues? In any event, she looks like she'd be quite the handful, doesn't she? 

Robby ended up calling my Facility and reached my receptionist, Cassandra. Oddly enough, Cassie and Carley appear to have a similar style, maybe even the same chip on their shoulders too?

It was a random Thursday, when Cassandra came into my office. 

Good morning, Ma'am. I have some dude on the phone, he's claiming he knows you. He speaks with a British accent. 

"Ahhh, yes. That must be Robby. I was expecting to hear from him today," I replied. 

He said something about needing to punish his submissive? Do you have time this afternoon, Ma'am? I guess he wants you to do the honours? 

"Actually no. He doesn't need any of our specialty rooms or our assistance. He just needs a private space to give her a spanking." 

Fair enough, Ma'am. I'll book him at a hourly, rental rate then? 

"Yes please, Cassandra, thank you." 

Robby and I actually had a little consultation last night. He didn't want my help, he didn't need my help, in disciplining his gal. Deep down, I think Robby was nervous that I'd seduce Carley...and the next thing you know she'd be dressed like this, and working for ME at my Facility:

While poor Robby would be reduced to a mere observer, wearing only one of these. 

Hehe...he probably wasn't wrong. Not the first time I've corrupted a sweet, young female while enslaving her man into chastity and panties. Ok...I'll sit this one out. 

When afternoon arrived, I greeted both of them personally. Carley was much more attractive than her pictures would fully portrait. She had the cutest little pixie face that was hidden beneath her gothic and smoky makeup style. 

Carley seemed shy and nervous, with her head bowed submissively and her little hands demurely folded in front of her. It was clear that she was in trouble. I didn't attempt to become involved or seduce her. I just let Robby do his thing. 

I offered the school classroom, the judicial court and prison space, the dungeon and even the sissy pink bedroom. Robby was grateful for all of the options I was suggesting, but eventually he said that this was a domestic matter and required a simple, domestic solution. 

I guess Carley had taken his credit card and done a little spending spree which was suppose to be for Robby, to please him, but she went a little overboard. I guess he has warned her about this before and sometimes wonders if she's doing this on purpose, just to get spanked. 

Poor Carley was listening to us talk about her imminent punishment, right in front of her in my office. When I offered Robby my living room, the most domestic setting available, he softly asked Carley to stand and remove her dress. 

She wore a simple but cute, spaghetti-strap, "little black dress" that looked great on her. She had either stockings or pantyhose on, also in black and a simple pair of patent black pumps. 

Reluctantly, she obeyed Robby and let the dress fall to the floor, right in front me. Next came her panties and bra, also cascading to the ground. She stood before both of us, exposed and vulnerable in just her stockings and heels. She was nervously fidgeting with her hands, but her gaze was steely and defiant. 

Robby broke the awkward silence in the room. 

The living room is just down this hallway, Ma'am? 

I snapped from my trance that was locked onto Carley's cute body. 

"Yes, Robby, make yourself at home. The room is yours to use." 

Thank you, Ma'am. 

And that was it...that was my involvement in this one. From down the hall I could hear the echoes of Carley's whimpers and the very familiar sounds of a heavy palm, meeting porcelain-smooth, female buttocks. 

It didn't sound like he used anything but his strong hand, but it was a very long spanking, from what I was able to hear. 

Ohhhh yes...I could hear every smack and every one of Carley's whimpers from my office. I may have...indulged a little, to the sounds of her being spanked. *blush*

Don't you judge me! Look at her! She's a cutie who's getting a spanking right now. How could I not diddle my little clit to her humiliation and misery? 

Robby, you can bring her back anytime! 

Mistress Andrea xoxo

Continued in: Tattoos and Tongues