Little Spoon

Continued from: Tucked in by "Mommy"

A Sarah Jane story

After finishing up the text convo with Mistress, I gave Russell about an hour, while I read some Miss Julie content, before heading upstairs to alleviate the pressure in his poor bum. An hour plugged, without a re-lubrication, is more than enough time to provide suitable humiliation, frustration and to train his little bottom hole for future use. 

He was permitted to attend the bathroom in private and remove the penis-plug, returning to me so I could unlock the baby pink, leather cuff set from his wrists and ankles. When he reached for his satin pink nightie, to pull it off over his head I stopped him dead in his tracks. "Not so fast, young lady," I snapped. "These are the jammies you will be sleeping in tonight." 

His bottom lip began to pout in protest, as he mewled out a desperate, "but, Mommy...please!" 

With a quick motion of my hand, I accessed the dreaded ebony hairbrush that laid in wait on my dresser, specifically poised and at the ready for moments such as these. I ran my palm across it's smooth, unforgiving backside, tapping it firmly against my open hand. 

"So you were saying...you'd be happy to sleep in your pretty pink jammies, young lady?" I asked, my voice dripping in unspoken threat. He lowered his eyes, sensing impending danger and with a defeated sigh of submission, "yes, Mommy," escaped his lips. 

I set the hairbrush back in its place, and we both crawled into bed, maneuvering myself to ensure that I would be the big spoon tonight. 

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

The morning light filtered through the curtains, casting a soft glow across the bedroom as I stirred from my slumber. My arm was draped possessively around Russell's waist, holding him close to me as I spooned him from behind. I reveled in the feeling of his soft babydoll and panties, the delicate fabric doing little to conceal the firmness of his chastity cage beneath. 

With a contented sigh, I began to explore his body with my hands, tracing lazy patterns across his chest and stomach. Russell squirmed in my grasp, a soft moan escaping his lips as I found his sensitive nipples through the thin satin of his nightie. I pinched and rolled them between my fingers, delighting in the way his body responded to my ownership, his breathing growing heavier with each passing moment. 

My other hand drifted lower, cupping the bulge of his caged cock through the satin thong. "Good morning, my little one," I whispered, my lips grazing the shell of his ear as I spoke. "Did you sleep well, all safe and secure in Mommy's arms?" 

"We have quite the day ahead of us. Mistress Andrea has invited us over for a visit." I felt Russell tense slightly in my arms, no doubt processing the implications of being in Andrea's presence for the first time, as MY submissive plaything. 

"But first, let's get you out of these adorable jam-jams, Mommy wants to start her day properly." With a final lingering caress, I released my hold on Russell, allowing him to sit up and begin the process of removing his feminine attire. The sight of his chastity cage, snugly locked around his cock, never failed to send a thrill of ownership through me.

"Go start the shower, young man," I instructed, my voice laced with authority. "I want you waiting for me in there, on your knees." 

As Russell scurried off to obey my command, I reached for the nightstand drawer, my fingers closing around the familiar shape of the strap-on dildo. For a moment, I hesitated, considering the possibility of claiming him fully, right there in the steamy confines of our shower. The thought of watching him surrender to me completely, of feeling his body yield to my thrusts, was almost too tempting to resist. 

Yet, even as desire coursed through my veins, I knew that such a monumental step deserved more consideration. Reluctantly, I placed the harness back in the drawer, deciding instead, to seek counsel from Mistress Andrea. Our upcoming visit presented the perfect opportunity to discuss this significant milestone in our dynamic. He doesn't even realize how close he came to being pegged this morning.

*Sigh...

Entering the bathroom, I was greeted by the sight of Russell kneeling in the shower, the hot water cascading over his submissive form. Steam billowed around him, creating an ethereal atmosphere that only served to heighten my arousal. I stepped into the shower, positioning myself directly in front of him, my legs spread in silent command. 

I tangled my fingers into his wet hair, gripping tightly as I guided his mouth to my waiting pussy. "Lick my pussy, young man," I ordered, my voice cutting through the sound of the falling water. "Worship my cunt with that talented tongue of yours. Don't stop until I'm cumming onto your lips." 

Each flick and swirl sent waves of pleasure right to my toes, building steadily towards an inevitable climax. I held his head firmly in place, using him for my own gratification. As the last ripples of my orgasm subsided, I gently guided Russell to his feet, as my hands reached for the loofah, lathering it thoroughly before turning my attention to his cock cage. 

I took great pleasure in meticulously cleaning every inch of his locked-up penis, ensuring that the cage itself was cleaned as well. I couldn't help but smirk as I felt Russell's brief attempt at arousal, his cock straining futilely against the confines of the chastity cage. 

Emerging from the steamy shower, I allowed Russell the privilege of drying my naked body, his touch gentle and careful as he patted my skin with the soft towel. 

As he completed his task, I sauntered over to the bed, selecting a pair of pristine white stockings from my drawer. With deliberate slowness, I rolled them up my legs, relishing the silky caress against my skin. I reclined on the bed and spread my legs like a huge slut, revealing my glistening pussy. 

I crooked a finger at Russell, beckoning him closer. "Come, young man," I purred the sensual command. "Your Mistress requires another orgasm before we depart."

Sarah Jane 💟

Continued in: Bi-polar BDSM

 

Pent-Up

Continued from: Why the Long Face?

When we left off with this cute couple, Vanessa was exerting her dominance over her sissy husband, allowing him a small moment of scent-association training after her return from work. The dampness of her hosed-feet, came to rest on Derek's mouth and nose, as she massaged and manipulated his caged cock through his panties.

His arousal and frustration level was nearly unbearable. 

Three days without her guiding hand had left him coiled tighter than a spring, emotions and desires building to a critical point. Vanessa recognized the signs - it was time for a therapeutic intervention. A gentle, soothing phrase escaped her lips as she beckoned Derek to head upstairs and position himself in the corner: "Off you go, my little one. let's take care of everything pent-up, shall we?" 

With a mixture of humility and hope, Derek clicked up the stairs in his Mary Janes, his movements tentative, like a child seeking comfort. He had come to learn within his unique dynamic, that being "pent-up" meant tears would flow from his eyes first, before the chastity tears would flow from his cage. 

As Vanessa ascended the stairs, the commanding click of her heels echoed through the quiet hallway, a solitary sound that seemed to amplify her dominance. Her gaze drifted upwards, fixing on the figure in the corner of their bedroom, awaiting his fate. 

Derek, clad in a patterned and delicate outfit of a little girl, stood with his hands on his head, elbows out. The air was heavy with contrition, as if the very atmosphere itself was infused with shame and humility. 

With practiced rituality, Derek had accessed the dreaded "spanking cart" from their walk-in closet. A simple yet elegant two-tier cart on wheels, containing straps, paddles, hairbrushes, a Lexan cane and plenty of tissues. He knew that before positioning himself in the corner, this needed to be displayed and presented for his wife's selection.

Vanessa positioned herself on the plush loveseat, exposing her hosed thighs in invitation. Once summoned from the corner, Derek turned in response, before mincing towards his wife.

Vanessa's slender fingers extended, helping him out of his dress and bra and sliding his panties down and off. With a pat of her lap, his body conformed to the familiar contours of her strict lap, in this time-honoured position. Her hand found its way to the small of his back with a little pressure, to pin him in place, as her sturdy palm began to soundly spank his bare bum cheeks. 

After a long warm-up over her knees, Derek was positioned on an end-table to be paddled. Vanessa sat comfortably nearby, allowing his anticipation to build and tears to rise to the surface. 

With a deep breath, Vanessa launched into the rhythmic motion, paddling his bare bum in a slow, measured cadence. At first, the impact was reasonable, but as the blows continued to fall, the sounds of pain and pent-up emotion began to mingle, culminating in deep sobbing from Derek. He was crying openly now, like a little girl. 

With Derek's emotional catharsis complete, Vanessa's focus shifted to the next stage of his therapy. From the beside drawer, she retrieved her trusty strap-on harness, the supple leather creaking as she buckled it securely around her hips. 

Next she selected a suitable condom, the crinkle of its wrapper piercing the silence as she tore it open with her teeth. With deliberate slowness, she rolled the latex sheath over Derek's chastity cage, creating a reservoir to capture any cum that might be coerced from his prostate. The unspoken promise hung in the air, Vanessa would milk him dry, relieving his pent-up desires while reinforcing her control over him. 

With a subtle adjustment, Vanessa aligned her body with Derek's vulnerable form, the tip of her strap-on poised at the entrance to his "sissy pussy". The initial penetration was followed by a series of shallow, teasing thrusts, each calculated to tantalize his prostate. 

As Vanessa's thrusts gained momentum, she began to slap his already brutalized ass cheeks, to coax him into vocalizing his feelings. "Tell me darling," she urged, her voice husky with encouragement, "do you enjoy being fucked like a girl?" 

A strangled affirmative escaped Derek's lips, his admission hanging in the room like a confession. "Y-yes, Ma'am...I I-like it..." The words dripped with shame and humiliation, a potent cocktail that fueled Vanessa's passion. 

"I love it when your cage slaps against my clit!" She purred out.

Her strokes grew more insistent, driving poor Derek further into the heart of his degradation, as she crafted another memorable chapter in their ongoing tale of this female-led-relationship. All that was pent-up, had been released. 

Welcome home, Vanessa! 

Derek...you better just stay on all fours, while she gets that condom off your cage and feeds you the contents. And don't forget to thank her for it. 

Mistress Andrea

xoxo

Continued in: Mad Men

Why the Long Face?

Continued from: Fallen Angels

"Why the long face, Derek?" 

Ohhh, right, right. It's because you go to bed every night and look down and see this: 

While your wife is in some layover hotel room, probably doing this:

You wake up in the morning, Derek, and diligently make your bed and tidy your room until it looks like this:

 While your wife wakes up in the morning and diligently addresses something also...

But don't worry, she'll be home soon. 

Do you remember Vanessa and Derek? Goddess Vanessa as I like to call her, and her loving, sissy cuckold husband, Derek. Their storyline began here: Vanessa is a Goddess

God she is stunning! I have a major girl-crush on her and actually let her Domme me one night, with MY wife's permission of course. 

You can read about that steamy session here: I often envy submissives

Since these two have such a unique dynamic, I wondered if I could bring them to life using ethically sourced, text-based image generation. 

I described Vanessa as Cuban, 30 years old, a flight attendant with a proclivity toward hosiery and heels, make-up, grace and poise. 

Ummm...*panty check*

Yep, I think we can work with this version of Goddess Vanessa. 

And what about poor Derek? 

Haha...he looks like a version of Zach from Saved by the Bell. You better not let your wife catch you in those boring boy clothes, Preppy! 

That's better sissy gurl. Get your chores done and the house cleaned before your wife gets home, and make sure you're dressed like a little girl, as she had asked...or you know you'll be in deep trouble!

As the sun rose over the Miami horizon, Vanessa, the ravishing flight attendant, prepared for the final leg home to Toronto.

Her raven-haired beauty gleamed in the blossoming light, her curves accentuated by the fitted uniform she wore so elegantly. Meanwhile, back at home, her devoted sissy husband, Derek, waited anxiously, dressed in a frilly maid's outfit, complete with satin gloves and a headpiece. His heart raced with anticipation as he finished handwashing Vanessa's delicates and ironing her laundered clothing. 

By afternoon, Vanessa's arrival home was imminent. Derek assumed the position, presenting himself at the base of the couch as a willing footstool. As she lifted one foot, then the other, onto his trembling back, Derek couldn't help but emit a sigh of contentment. 

With deliberate slowness, Vanessa slipped off her stilettos, setting them carefully and neatly in front of Derek's nose. The scent of warm leather and musky nylons, mixed with lotion, wafted upward. 

His nostrils flared, drinking in the aroma as he gazed longingly at the insides of her high heels, a spot he knew his tongue would soon be put to use. Vanessa settled in, letting out a satisfied moan as she rested her hosed feet on his back, feeling the warmth of his skin through the fabric of his sissy attire.

Vanessa's weight pressed down upon him, her toes curling gently over his shoulder blades. Derek's mind wandered to the ache beneath his satin panties. The steel confines of his chastity cage seemed to tighten, a cruel reminder of his captivity. The delicate lace trim of his underwear, adorned with tiny hearts and flowers, only added to his sense of emasculation.

The contrast between his restricted cock and Vanessa's carefree sensuality was a constant thorn in his side. Yet, as he breathed in the heady aroma of her stockinged feet, now resting comfortably on his nose, Derek knew he wouldn't trade this humiliation for anything. 

For in this world, Vanessa was queen, and he was but a lowly subject, destined to serve her every whim. 

It didn't quite help his cause however, that she was the queen of a certain suit. 

Welcome back, Vanessa and Derek. We've missed you!

Mistress Andrea

xoxo

Continued in: Pent-Up

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?