Roommates

Continued from: Boardrooms & Bedrooms

If you remember, during the last post, my ears perked up like a deer, when young Skylar casually made a comment about spanking her roommate in university. That's right, this Skylar, the Librarian, with absolutely no experience in BDSM: 

My mind spun a visual of two giggling 19-year-olds with tequila on their breath, tickling and wrestling on their single beds after the bar. A couple smacks on the bum for one of them being too drunk, followed by a pass-out and the promise of a hangover the next morning. 

"No, it was for REAL." Skylar corrected, and began to tell me the whole story. 

By the end of her tale my mouth was dry, my jaw was on the floor, and the butterflies in my tummy were raging like a storm. 

Skylar has published papers, written a doctoral thesis and obviously reads like a fiend. She is very well-written and well-spoken. I thought I would ask her to write this one herself, she reluctantly agreed. Take it away, Sky. 

*************************

I remember the day we met like it was yesterday. I had just finished unpacking my bags in our shared dorm room, my muscles aching from the effort of lugging my belongings up three flights of stairs. As I stood there, surveying my already cluttered space, the door swung open and in walked this vision of exotic beauty. 

"Hi, I'm Eesha Patel," she said in a subdued tone. 

Eesha was petite, with long, raven-black hair. Her almond shaped eyes were green, framed by impossibly long lashes, and her lips were set in a shy smile. She was dressed simply, in jeans and a loose t-shirt.

I introduced myself, exchanging pleasantries and discussing our fields of study. Eesha was going to be a doctor. I could sense a tension in her, a coiled energy that seemed at odds with her gentle demeanour.

Over the next few months, as we settled into our routines, I noticed small things about Eesha. The way she would bite her lip when in deep thought, the nervous habit of twirling a lock of hair around her finger when stressed. She confided in me about her struggles with the demanding course load, her fear of falling behind. 

One day, in our second semester, Eesha burst into our room, her face flushed with anger and disappointment. She slammed her backpack onto her bed, sending papers flying everywhere. I looked up from my computer, startled by the sudden commotion. 

"What's wrong?" I asked, concern etched on my face. Eesha turned to me, her eyes brimming with unshed tears. 

"I failed," she whispered, her voice trembling. 

"Failed? But you're one of the top students at this entire university!" I protested, rising from my bed to comfort her. 

Eesha shook her head vehemently. "No, you don't understand. I got an 86 on my biochemistry exam."

I frowned, confused. "But that's a great mark. What's the problem?" 

Eesha sank onto her bed, her shoulders slumping. "In my family, anything less that a 90 is considered a failure. If my parents knew..." She trailed off, a shudder running through her body. 

"When I was younger, if I ever brought home a grade like this, my mother...my father would..." She hesitated, her cheeks flushing a deeper shade of red. "They would punish me," she admitted in a rush, her gaze fixed on the floor. 

I stared at her, shock and something else, something darker and more thrilling, coursing through me. "Like…Spank you? For getting a B+?" 

Eesha nodded miserably. 

"I know it sounds crazy, but it's how I was raised. The fear of disappointing them, of facing that punishment...it drove me to excel. And now, here I am, failing without that motivation. 

The next evening, as we prepared for bed, the atmosphere in our room was thick with tension. Eesha moved silently, her movements jerky and uncertain. She was dressed in a simple tee and sleep shorts, as I was. 

She climbed into bed and paused, her hand trembling as she reached for something on her nightstand. Slowly, she turned to face me, her eyes downcast, her cheeks burning with embarrassment. In her hand was the crumpled test paper, the damming 86 circled in angry red ink. Without a word she held it out to me, her arm shaking slightly. I took the paper, smoothing it out on my lap, my heart pounding in my chest. 

When I looked up, Eesha had sunk to her knees beside my bed, her head bowed low. "Please," she whispered, her voice barley audible, "I need you to punish me. Like my parents would. I deserve it for failing." 

I stared at her, my mouth suddenly dry, my palms sweating. The sight of her, so vulnerable, so desperate, ignited something within me. A darkness I had always known lurked beneath the surface, waiting for the right moment to emerge. I swallowed hard, my gaze flicking from the test paper to Eesha's trembling form. 

I sat up straighter on my bed, the test paper crumpled in my fist. 

"Eesh, I...I wouldn't know what to do," I admitted, my voice wavering. "I've never done anything like this befo…" But even as the words left my mouth, Eesha stood and remained silent, hooking her thumbs into the waistband of her pajama shorts. With agonizing slowness, she slid them down to her ankles, then completely off her socked feet. 

Then, in one fluid motion, she gripped the hem of her t-shirt and pulled it up, exposing the smooth expanse of her tummy and lower back. Before I could utter another word, she had draped herself across my lap, her body warm and pliant against mine. 

My hand hovered above the rounded globes of her bare bum, trembling slightly, as I fought the urge to caress her. Eesha's Sobs filled the room and I knew I couldn't deny her this, we had become such great friends over the past months. 

"Please Skylar," she wept, her voice raw with desperation. "Punish me, hard! I need it...I deserve it."

Goddess Sky

nee:

Dr. Skylar St. Germaine 

Continued in: Doctor Patel

 

Teacher's Pet

Continued from: School Ties

A Sarah Jane story

As Mandy and I stepped into the classroom, the sight that greeted us was one of pure vulnerability. There, seated near the teacher's desk, was my beloved Russell, naked from the waist down and tightly bound to the chair. His chastity cage glinted in the fluorescent light, a stark reminder of his utter helplessness in the face of our feminine allure. 

Beside me, I heard Mandy's sharp intake of breath, followed by a delighted giggle. "Oh, Sarah," she breathed, her eyes wide with wonder, "is that really his...you know?" I chuckled, amused by her naivety and innocence. 

"Indeed it is, my lovely," I confirmed, my voice dripping with a cocky ownership. "That little metal prison is all a girl needs to get whatever she wants. Isn't that right, young man?" 

Russell's face contorted with a mixture of shame and longing, his eyes frantically darting between Mandy and I, and the outfits we were in. "Y-yes, Ma'am," he managed to squeak out, his voice thick with humiliation. Mandy and I started kissing, but curiosity got the better of her and she broke away from my lips. 

Mandy took a tentative step forward and knelt down before him, in a perfect, submissive blowjob pose (what a little temptress she is!). "Can I...can I touch it, Sarah?" she asked, her hand already reaching out towards the gleaming steel. 

I smiled indulgently, nodding my permission. "By all mean, sweetie," I encouraged her. Mandy's little hands brushed against the cool metal bars, eliciting a gasp from deep within Russell's throat. She traced the contours of the device, marveling at its simple design and the way it seemed to pulse beneath her touch. 

"It's so...small," she teased, her lips curling into a vengeful smile. 

I reached down and grabbed the cage firmly, giving it a gentle tug that made Russell gasp out loud. "You see, my sweetie, this isn't just about physical restraint. It's about psychological domination, breaking him down with denial until he is nothing more than a dribbling slave. 

"I think I'm starting to see the appeal, Sarah. I'm so wet right now," she giggled, her hand joining mine to stroke the metal cage.

"Really?" I challenged her, "lemme see," and I pushed her playfully over one of the school desks. With a flourish, I hooked my thumbs under the waistband of Mandy's delicate panties, slowly sliding them down her smooth thighs. 

I could see the soaked gusset of them, a testament to her growing arousal. Russell watched, transfixed, as I brought the soiled panties to his face, allowing him a brief moment to inhale the intoxicating scent of Mandy's desire before stuffing the silky material into his eager mouth. 

With the makeshift gag in place, I was sure he would remain relatively silent throughout our little show. I turned my attention back to Mandy, my eyes drinking in the sight of her glistening, bare pussy, now fully exposed to my hungry gaze. 

"Spread your legs for me, sweetie." I commanded softly in a sultry purr. Mandy complied without hesitation, parting her thighs to reveal the swollen, pink flesh of her beautiful pussy. 

After spending some time with my ass in Russell's face and my tongue lashing at Mandy's clit, I gestured for her to lie down on the floor. I positioned myself above her, my knees on either side of her head, my own soaked pussy hovering tantalizingly close to her eager mouth. 

We brought each other to a simultaneous orgasm that echoed through the room, losing ourselves in the symphony of our shared pleasure. I helped Mandy up, guiding her to the nearby desk. With a firm hand on the small of her back, I bent her over the polished wood, lifting her skirt to expose her recently whipped bum. 

I retrieved a strap-on from the teacher's desk and fastened it around my hips, relishing the feeling of power that coursed through me as I prepared to claim Mandy as my own. With a single fluid motion, I plunged deep into her welcoming cunt, her moans of desire mingling with Russell's muffled cries of frustration. 

I grabbed her ponytail as a handle and set a punishing pace, my hips slapping against her sore ass with each powerful thrust. 

As I continued to fuck her relentlessly, I reached beside me to yank the panties from Russell's mouth. His jaw fell open, his chest heaving with ragged breaths as he watched me bring the glistening dildo to his lips. 

"Suck it," I ordered, my voice firm with authority. 

The debauched scene played out something like this...

...with multiple trips back and fourth between Mandy's pussy and Russell's mouth, until she shuddered her way into another orgasm. 

With her pussy still contracting and pulsating, I slowly re-entered her and gently treated her to a few more thrusts, while looking back at Russell deviously. 

"Don't worry my pet," I purred to him, my voice laced with dark promise. "Your turn will come soon enough. But for now, be content with the knowledge that you have pleased your Mistress and her friend, and that is reward enough."

Just then, Mandy embraced me in a warm hug, asking bashfully, "Mistress, can we do this again?" 

'Mistress' she chose to call me...huh.

It looks like this Mistress has a new pet!

Sarah Jane 💟

Continued in: Caesar Sunday

School Ties

Continued from: Girl-Talk Continued

A Sarah Jane story: 

I helped Mandy down onto her tummy on the plush sofa, and began to plant gentle little kisses onto her whip marks, that were slowly fading beneath my lips. 

She thanked me for the aftercare and kissed me on the mouth, just as the back patio door swung open, revealing the sheepish figure of Russell trailing behind the stunning Summer, still clad in her provocative lingerie. 

The poor boy looked absolutely miserable, his chastity cage undoubtedly causing some discomfort after being teased and tantalized by Summer's irresistible presence during their time outside. Little did he know, however, that his true torment was only just beginning. 

I looked toward Russell and gave him a reassuring yet cruel smile, as I whispered quite a lengthy scheme into Mandy's ear. I heard her gasp, then giggle, followed by her response to a question I whispered to her. 

"No, Sarah," she excitedly replied, "I don't have anywhere else I need to be right now." 

I turned to Summer who could tell that some manner of debauchery was brewing. "Summer...huni," I cooed to her while still glaring at Russell. "Would you take my boy to the classroom please, and make sure he's nice and secure in that teacher's chair." 

Summer flashed me a wicked grin, clearly enjoying her role in our twisted game and my newfound dominant role. I'm quite certain she was picturing Mandy and I like this, in the classroom:

Stripped and shamed, placed on display before the rest of the students, and about to have our pristine bottoms paddled by Russell. This was the narrative Summer would have been more accustomed to. 

But my, my how the tables have turned...

"Oui," she replied, her hand firmly gripping Russell's upper arm as she led him away. "I'll make sure he's properly prepared, Madame." She left me with a wink as clicked down the hall with Russell in-tow.

As they disappeared into the classroom space, I turned to Mandy, my eyes gleaming with mischievous intent. "Come along, pretty girl," I purred, linking my arm with hers. "Let's get dressed up like slutty schoolgirls and give the 'teacher' a show." Mandy giggled nervously and together, we made our way upstairs to one of the dressing rooms. 

As we stripped down and began to don our chosen attire, I couldn't help but admire Mandy's cute little form. 

The short plaid skirt accentuated her curves perfectly, while the crisp white blouse struggled to contain her beautiful tits. 

I struck a pose once my outfit was on, which caused Mandy to tell me that she was soaking through her panties. But the real test will be Russell's reaction. I want to see the desperation in his eyes as he watches us, knowing his penis is locked and under my control. 

With a final adjustment to our outfits, we held hands and embraced once more, stealing a quick kiss before the true fireworks were set to pop off. 

Our heels clicked rhythmically against the polished hardwood as we approached the classroom. Pausing outside the door, I turned to Mandy, my expression suddenly serious as I dropped a quick prep-talk.

"Remember, huni," I said softly, "this is about more than just our physical pleasure. It's about asserting our dominance, about showing Russell that he is utterly powerless in the presence of us two women. So let's give him a performance he'll never forget! 

Sarah Jane 💟

Continued in: Teacher's Pet

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