Doctor Patel

Continued from: Roommates

Written by Skylar St. Germaine

"Please, Skylar, punish me." 

Her words sent a shiver down my spine, igniting a fire within me that I had never felt before. My hand, poised above her bare bum, clenched into a fist before relaxing again. 

With a swift, decisive motion, I brought my palm down hard against Eesha's upturned ass. The sound of flesh meeting flesh echoed through the room, mingling with Eesha's sharp cry of pain. A red handprint bloomed instantly on her bronze complexion, and I watched, transfixed, as she squirmed against me. 

Again and again, I spanked her, each smack harder than the last, my hand stinging with the force of the impacts. 

With each punishing blow, Eesha's cries morphed into desperate apologies and promises. "I'm sorry," she sobbed, her voice breaking. "I'll do better, I promise. Please, Skylar, I'll be a good girl!" 

Her words fueled my fervor, spurring me to spank harder, faster, until her ass was a canvass of crimson and purple. 

"I won't disappoint you again," she vowed, her tears flowing freely now. "I'll study harder, I swear!" 

When I felt Eesha go limp across my lap, I slowed my assault, my hand gentling to soothing strokes across her bare bum. "Shhh," I whispered. "You've been punished enough for now." 

Eesha collapsed against my legs, her body heaving with exhausted sobs. Slowly, she slipped her arms around my waist in a tight embrace. "Thank you for punishing me, Skylar." I ran my fingers through her disheveled hair and told her everything would be okay. 

Eesha clung to me for a moment longer, before reluctantly releasing her hold. With a soft sniffle, she rose unsteadily to her feet, wincing as she gingerly rubbed her sore bottom. I watched as she shuffled towards her bed, her steps hindered by the panties still pooled around her ankles. She crawled atop the covers, curling into a small ball around a pillow and quietly sobbed herself to sleep. 

For Eesha, this was no game, no sexual fantasy. It was a deep-seated need, a compulsion born of years of strict upbringing and the weight of expectations. And I, her friend and confidante, understood the gravity of my new role. 

In the months that followed, an unspoken ritual emerged between us. Every few weeks, I would return to our dorm room to find Eesha standing in the corner, her shoulders shaking with silent sobs, her bottoms and panties pulled down. 

Wordlessly, I knew this was my queue to help her with whatever she was struggling with. I would guide her by the bicep to her bed, to my bed, or to a nearby chair, and position her directly over my lap. 

As our ritual evolved, so too did my autonomy to punish her more creatively and effectively. On some occasions I would reach for my belt, other times it was Eesha's own hairbrush, the unforgiving wooden surface leaving ashy-white splotches on her bare bum. 

I began to incorporate enforced corner time into our sessions, before and after her spankings. I even insisted that she start stripping fully nude for me, before being sent to the corner or going over my knee. 

"Socks too, Eesha. I want you fully nude," I would command and she covered her face with her hands and cried into her palms. 

These moments of vulnerability, of enforced introspection, seemed to bring Eesha a sense of peace. They allowed her to confront the demons that drove her need for strict punishment, to accept the consequences of her actions. 

Years have passed since I last saw Eesha. Our paths diverged after graduation, she pursuing her dreams in medicine, while I took an internship with NASA. But now...now I'm here, at Mistress Andrea's Facility, providing the exact same service to men and women, that Eesha once needed. 

I often find myself wondering what Eesha would think if she saw me now. Would she recognize the echoes of our shared past, in the way I wield a paddle now? Or would she see me as some sort of deviant, a perversion of the friend she once knew? 

I like to believe that Eesha would approve. After all, it was our time together that first awakened this side of me, that showed me the transformative power of adult spankings and discipline. 

I stared at my phone, my thumb hovering over the screen. It had been years since Eesha and I had spoken, yet the memories of her vulnerability lingered within me. I wondered if she still felt the same need for structure, for discipline, that had once landed her over my knee with her bum bare. Or did she still crave the cathartic release that only a thorough spanking could provide? 

I was between discipline sessions at the Facility, and before I could second-guess myself, I typed out a simple message to Eesha: a single heart emoji, followed by the words 'miss me?' 

I hit send, my pulse quickening as I waited for a response from Eesha, who was listed in my phone as Doctor Patel. Finally. three dots appeared, signaling that Eesha was typing. My breath caught in my throat as I watched the screen, anticipation coiling in my gut. 

And then her reply: 

"More than you know."

My heart leapt at the sight of those four words, a surge of warmth flooding through me. Whatever doubts I may have had about reaching out, vanished in an instant. Eesha still needed me, still craved the unique brand of discipline that only I could provide for her. 

And I was more than ready to deliver!

Goddess Sky

Continued in: Adorable A.I.

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

What Katie Did

Continued from: Roses are Red, Summer is too

I am in no way, shape or form affiliated to the vintage lingerie brand titled, "What Katie Did". It just so happens to be the name of this post, based on a client of mine named Kate. 

The lingerie however, is one of my favourtite brands. It's 1930's 40's and 50's pinup style, dresses too. The stockings, the seamed ones, the fully fashioned ones, are simply divine. Anytime a client of mine needs to be spanked by "Mommy", the collection from What Katie Did are my go-to styles.

Kate, on the other hand, is a new-ish client of mine. I find her to be quite a fascinating individual, based on the type of service she wants from me. I thought she was worthy of a post, my darling Katie, as I refer to her when she's with me. 

Picture like a Diane Lane...Aged beautifully, elegant, sharp and seriously feminine! Her experience shines brightly, in the odd strand of platinum-silver, that now runs through her hair. She doesn't dye it. She wants her level of maturity on display. This is essentially how I would describe Kate. 

I'm not 100% sure what she does for a living but my instincts tell me that she is some manner of corporate powerhouse. A CEO, a CAO, maybe the Director of a finance or legal department. She absolutely oozes corporate power, but comes to me to be spanked. 

I get it...I understand why she wants and needs this type of escape, given her vanilla role. I'm not sure if it was topping from the bottom originally but she basically told me exactly how she wanted her appointments to go. I obliged her, she tips well!

She only ever books with me over her lunch-hour on a weekday. Like visiting a therapist or dentist, like booking a massage. It's in her calendar, it's once a month and she is always on time. 

Kate graciously brings me an overpriced coffee, which she sets on my desk like an apple for the teacher. She mutes her phone and sets it on my desk also, along with her purse.

She of course greets me with a smile and a "Hello, Ma'am", but beyond that she doesn't say anything else. Kate just walks to the corner and parks herself in timeout. Sometimes I lower her dress-pants to her ankles, sometimes I just let her be. 

30 full minutes. This is what Kate asked of me, to strictly enforce 30 full minutes in timeout. I hear her breathing change around the ten minute mark. Deep inhales and deep exhales, as she stands motionless in her stilettos. 

Her panties always stay on for her spanking. If she's not in a tiny little thong which she usually wears, I will wedgie her panties up her bum crack so my target area is predominately bare. Her pussy and bottom hole have always been covered, upon her request. 

She wears a wedding band...maybe that's why? Maybe her hubby allows these sessions for her provided her modestly is maintained? I think she wears the pants at home though. Her hubby is probably a sissy maid to her. She reeks of female dominance...just not in these particular moments, and that's exactly why she needs these particular moments.  

The level of spanking on a severity scale of 1-10, Kate wants an 11. Bathbrush, the strap, hardwood paddles, canes, hairbrushes. She wants me to take her to "yellow" every time, but will never say "red". She believes it shouldn't be her decision when her spanking ends. 

Remember faint-of-heart people, this is what she has asked for:

Once per month, on her lunch break, without fail, she leaves my office with a bum that looks like the above and sometimes a tear-stained face. 

She is quite the trooper. Sometimes she doesn't even cry, she just silently takes it. 

When I declare "that's enough till next month", she drops to the floor and kisses my footwear while thanking me. Sometimes she's bawling...sometimes she's fully composed. Kate wanted this as part of her ritual for some reason, to lower herself to the floor and kiss my high heels. 

Then, just like her arrival, she walks herself to the corner and parks her nose against the walls. I start the timer again...for another 30 minutes if you can believe it! Her request. 

30 minutes in the corner, 30 minutes of spanking typically and 30 minutes in the corner, once a month! This is how she spends her lunch break. A truly intriguing woman! 

When the timer finishes she dresses. She holds me tightly and says, "thank you", and off she goes. It's somewhat mysterious. Like I want to know what happens after she leaves me or see her back at work, squirming in her seat. Her spankings are so severe that she'd be feeling the effects for a week, and seeing the marking and bruising for two weeks. 

Does her hubby see her bum and become horrified? Aroused? Does Kate get sexually aroused from this? Probably...but likely not in the moment. So mysterious! 

After our embrace she un-mutes her phone, grabs her purse and coffee...and boom, back to corporate power-fem. 

I end with a "see you next month, Katie". But not spoken as a statement. I frame it as a question, always open to her consent to continue or not. 

"See you next month, Katie?"

"Yes Ma'am, I'll be here, thank you Ma'am". 

And I kiss her forehead...

I'm not sure what Katie did, to feel she deserves such treatment each month. 

Maybe it's just the greatest possible escape a corporate adult could ever hope for. 

I admire her nevertheless!

Mistress Andrea

xoxo

 

Home Sweet Home

Continued from: The Huntress

So we land in YYZ, Summer and I, having enjoyed a lovely week in Paris together. We grabbed a limo for the trip home, slightly exhausted from the flight. I was eager to wash the travel off me. Summer was too. It was nice to be home again...

Until...I walk into my living room to this scene! 

Both of us giggled out loud. Cassie fuckin' kills me sometimes!

You can see for yourself, but Summer and I walk in on her gaming, on the couch, looking like she's been smoking weed all day. Her bratty, Nike High Dunks are resting on the back of some ridiculous male submissive who she has dressed in lingerie and heels. 

Within her strict gaze, a second pathetic specimen of a male, kneeling and gussied-up, head-to-toe as a French Maid.

Apart from Cassandra's munchies on the end-table, the place was actually spotless, the fridge was full, and the sinks and toilets sparkled. Ha! She and her sissy maids can house-sit for me anytime!   

In the vanilla world, this would of course be a shocking scene to walk in on. Here at my Facility, it was simply a Tuesday. The poor sissies had such pouts on. Just sickened with humiliation, especially after Summer and I showed up.

Remember the infamous Mistress Elaine? The British woman who would totally own these poor submissive men by dressing them in layer upon layer of satin and petticoats, heels and hosiery. 

This poor chap she always addressed as "Vicky". He always had the same pouty look on his face once she had him fully made-up. It was a look of such defeat, just nauseated with humiliation. 

There's the look. Isn't Vicky a precious little gurl? Silky-smooth and hairless.

Mistress Elaine was notorious for using the full stainless chastity belts on Vicky and some other sissies who made appearances. One of them even had an electric-shockable anal attachment that locked onto the main chastity belt. That was a wild video...watching her torture this poor dude's rectum, while he begged and squirmed around on the bed in vintage lingerie and a dress. Totally something Cassandra would do... 

Apart from torturing her sissies, Mistress Elaine would often get them fully dressed-up and their little dicklettes locked away, before making them perform curtsies, to humiliate them. She would make them mince around the house and serve as Victorian-era maids.

Her scenes always involved Vicky in shit for something or Vicky had not performed a clean enough curtsy. Mistress Elaine would then spank, cane and paddle his bare bum, then peg the sissy with a strap-on. What a Goddess huh? She wielded a wonderous cocktail of physical and psychological dominance. 

I read somewhere that she was actually the seamstress or dress-maker, who custom-designed these satin and ruffled outfits. Who wakes up one day, with a skill-set like she has for these lovely artistic creations, and decides to start making them in men's sizes, to eventually keep a stable of sissy maids? Haha...amazing.

Good for her! 

Come to think of it, I should have a dress-maker on staff at The Facility. Some of these silly males would go beet-red if they had to come to me to be custom-fitted for a sissy dress. Something like this perhaps, for the most masculine of my submissive men?

A skilled seamstress could also add the lockable features for me, to any sissy outfit. These little additions are an absolute must for any sissy of mine!

Yes...on their bras too: 

It's one thing to forcibly feminize a male submissive as a form of control, punishment and humiliation, but you can take it to the next level psychologically, if their delicate attire cannot be removed without bolt-cutters or the keys! Lol...

 

Anyway, back to Cassandra... 

She had a padlock on the neckline of the maid dress one of her men was currently wearing. She also had their high heels padlocked to their feet. Good girl, Cassie! I taught you well. 

I noticed the dude in the pink lingerie had an inflatable plug up his ass. Typically something you would use to stretch and prepare the area for a good fucking. 

I gestured toward the sissy with the plug and asked Cassie, "are you preparing her pussy for something?"

Cassandra replied and pointed to the man in the maid's dress, then to the sissy on his hands and knees.

"Yes Mistress Andrea, this one (maid) is going to fuck this one (lingerie), but they didn't want to participate in anything homosexual, they're both straight." 

Ok...well how is one going to fuck the other then? I thought to myself...

Ahhh...leave it to Cassandra and her creativity, to push the limits of these two without breaking the limits. 

Is it still gay if it's not your own cock? 

Summer and I may have to stay and watch this go down...

Stay tuned. 

Mistress Andrea

xoxo

 

Continued in: Is it Gay?