The Deep End

Continued from: Trophy Wife

Preface

I recently joined Reddit, as it seems to be a welcoming platform where there are not only BDSM and spanking groups, but also Sims and NSFW Sims groups. I have more blog fans coming forward than ever before. Tons and tons of sissies in chastity, omg. The sissies are well represented on Reddit, good for them, and be sure to stay locked while you read my blog, gurls! 

I wanted to take this opportunity to explain to some of my new readers, how this blog came to be in the first place. 

I was inspired by a fellow blogger, Miss Julie. It's really that simple. If you're new to blogs and are recently here as a result of Reddit, I highly recommend you go check her out: 

Strict Miss Julie Spanks / Miss Julie Spanked  

The content is predominately spanking, domestic discipline, vulnerability and humiliation of adult males and females. Diaper play, pee, pegging, chastity and so much more. Oh, and many of these stories are REAL, as she chronicles in explicit detail, the spanking escapades of her and her hubby's "unique" relationship. Some of mine are based on real people and real events from my life, but hers...well, go see for yourself. 

She's been at it for over a decade now, with north of 16 million page views. She has published a series of e-books, these were great to read with such spanko embarrassment and shame it'll make your skin crawl and dick hard. For all the ladies, wayyyy better masturbation fuel than fifty shades, trust me! 

Collections of Spanking Stories

Miss Julie and I are in no way affiliated, apart from the fact we're both Canadian. We just seem to be the last of a potentially fleeting group of bloggers, still trying to provide an escape and a thrill to our loyal readers. I've always been a fan of hers and I urge you to go have a look, let me know what you think.  

I should have noticed this sooner, but Miss Julie always seems to mix in a pool scene. Whether it's an overly flirty wife, needing to be spanked in the pool house, or it's some middle-aged uncle, creeping his tight little niece in her bikini. Either scenario usually ends with a very red bum and even redder face. I thought to myself, I've never done a pool scene; despite the fact the Sims platform allows for a pool. 

It's been a hot summer so far, maybe it's time to install a pool!?  ; ) 

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

The Deep End 

**Caution: this story involves taboo, family dynamics**

It was a languid afternoon in late September, the sky was a brilliant shade of blue, with only wispy strands of cloud scattered across its expanse. In the midst of this serene backdrop, Marcus and Connor, two-rambunctious teens, found themselves arguing with their parents that they no longer needed a babysitter. 

Their parents, embarking on a well-deserved evening out, had arranged for the boy's cousin, Cassandra, to babysit. The boy's moods were tempered by the looming prospect of being cooped-up indoors with an icky girl, while they'd rather play guns or trucks, or do boy things outside.

As they idled away the minutes, their restlessness was palpable until suddenly, the doorbell rang, signaling the arrival of their unwanted caregiver. Her ensemble was boring and drab to the boys, with a palate of tones reflecting her Catholic-school uniformity, finished off with nerdy glasses that screamed book-worm.  

As the evening unfolded, Marcus and Connor became engrossed in the virtual battlefields of their video games. Meanwhile, Cassandra settled onto the floor with textbooks and notebooks arrayed around her. Her pleated schoolgirl skirt, seemingly innocent, rode up incrementally as she kicked-up her legs at the back and got down to studying. The merest hint of snowy-white panties poked from beneath her pleats, the fabric was so fine they appeared almost sheer, inviting the boys' imaginations to fill in the blanks.

An unspoken understanding hung in the air, as the boys exchanged glances. A silent conspiracy of adolescent longing, each secretly nurturing a forbidden fascination with their 18-year-old cousin.

This was the last time the boys saw Cassandra. As the years passed, they knew she went away to some swanky dance academy, at a school for the performing arts, but she seemed to fall off the map after that. 

Until however, the summer of 2024, when temperatures rose above forty degrees Celsius in southern Canada.

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

"Connor, Marcus," their mother sang out to them. "Your Auntie Bella has a pool...she asked if you'd like to spend the week at her place. I think your cousin is home too..." 

As the Thompson brothers sheepishly stepped out of the sweltering summer air and into the shaded grandeur of Aunt Bella's estate, their gazes collided with a vision that left their jaws agape. Before them, stood their cousin Cassandra - a ravishing metamorphosis of the emo youngster they remembered. Her transformation was nothing short of breathtaking, as if she'd been reborn from the embers of adolescent awkwardness into the sultry goddess before them. 

The smallest of jean shorts cupped her rounded bottom, while a white bikini tops strained to contain her perfect breasts. A dazzling array of tattoos danced across her skin, swirling in intricate patters that shimmered in the dappled sunlight, filtering through the trees. Piercings glinted along her ears, nose and belly button, imbuing her with an edgy, rebellious allure that had Connor and Marcus salivating. 

The air was heavy with tension as they struggled to reconcile this audacious beauty with the gangly, introverted girl of their memories. Cassandra surveyed them coldly, her expression unreadable beneath the blackness of her sunglasses. The scrawny teen boys tried to puff up and look muscular, but Cassie had already rolled her eyes at Marcus' feeble attempt to grow a beard, and pursed her lips at Connor's unmanly blondeness.   

As the brothers rough-housed in the turquoise waters, their laughter echoing off the estate's manicured lawns, Bella and Cassandra reclined on sun-kissed loungers, observing the commotion. To nineteen-year-old Marcus and eighteen year-old Connor, Auntie Bella and their cousin Cassandra represented dual incarnations of feminine allure, each exerting a distinct yet equally potent pull on their adolescent libidos.  

While Cassandra's pierced, tattooed beauty embodied the reckless abandon of youth, Aunt Bella's sultry, mature glamour seemed to hint at secrets and experiences gleaned from a world beyond their wildest imaginings. 

Suddenly, Cassandra carelessly tossed aside her miniature jean shorts. The brothers' gazes converged upon the tantalizing spectacle unfolding before them. 

Her toned body, honed from years of professional dance, was now splayed across the lounger, the tender flesh of her bum bisected by a thread of white bikini fabric. The delicate thong, stretched taut within the crevice of her ass, became an object of fixation for Marcus and Connor, which did not go unnoticed by Aunt Bella. 

As they lingered in the cool waters, Marcus and Connor discreetly waited for their inflamed desires to subside, willing their stubborn erections to recede beneath the surface. Finally, with their bodies returned to a state of semi-calm, they scrambled out of the pool, exchanging awkward glances as they both declared they needed to pee, while making their way toward the pool house. 

They slipped into the relative seclusion of the pool house to discover a treasure trove of forbidden delights. This must be where Cassandra changed! A set of women's clothing lay strewn about, amidst the scattered garments, one item captured their undivided attention. 

Without a word, Marcus and Connor simultaneously converged upon the enticing prize, their fingers closing around the delicate and sexy panties, recently shed by their cousin. Giggles bubbled forth as they handled the intimate relic, their imaginations conjuring visions of Cassandra's dripping arousal, sheathed within those very silken folds.

As they stood transfixed, their fingers fondling the silky panties, the sound of Aunt Bella's voice shattered the spell, her words laced with a maternal reprimand. "What do you two think you're doing? Don't you know better than to rifle through someone's private things?" Her tone conveyed a stern authority, yet beneath its surface lurked a hint of subtle amusement. 

Marcus and Connor froze, their faces flushing with guilt as their minds raced with the implications of being caught. As Bella's words still hung in the air, Cassandra sauntered into the pool house and was struck with the realization of what just happened. 

"You perverts!" She hissed, her black-eyes glaring, searing through the brothers. "Sniffing my panties like a couple of animals! What kind of sickos are you?" 

"No, we didn't do that, we just picked th-them..." Connor tried to plead their innocence but to no avail. 

Bella's countenance darkened, her features compressing into a mask of displeasure. "You've crossed a line, boys," she declared, her voice laced with a quiet fury. "Despite your adult ages, I'm afraid a lesson in privacy and respect is due. You're both going to receive a well-deserved spanking, on the bare!"

As the boys exchanged panicked glances, Cassandra's hand snapped out, clutching Connor's earlobe, while Bella seized Marcus' with an unyielding grip. Together, they frog-marched the struggling brother's towards the main house, Bella's heels clicking out a staccato rhythm on the stone pathway. 

The afternoon air was heavy with tension as they vanished into the privacy of the home, leaving behind a trail of humiliation and fear in their wake... 

*Gulp* 

Uh-oh boys, you're in for it now. Although, I'm sure some of my readers would volunteer to take your place...about to be spanked by a mother/daughter duo!

It must be so horrible! *wink*

Mistress Andrea

xoxo

Continued in: Splashing the Water

 

 

Wait for him by the door

Continued from: Sissy's morning ritual

Brad actually works on Saturdays. So after fucking his hot wife, having his dick cleaned off by his wife's sissy slave, he hit the showers, changed and left for work. 

Meanwhile, Lexi was being dressed into his frilly maid attire with stockings and heels, and layers upon layers of ruffles and bows. 

Saturday is the first full day of his sissy captivity and all he has to look forward to are lists upon lists of chores. 

All domestic duties that Erin would be doing while her hubby is at work, are done by Lexi. Chores like handwashing Erin's panties, the soiled ones that sissy so diligently held against the wall with his nose, is an example of one of these chores. 

And Lexi does all of this, with an anal plug up his ass. 

Toward the end of the day, as Erin is finished up with her tanning, her shopping and a professional massage, she returns home to find Lexi still working away in the kitchen, scrubbing the sink.  

"Go wait for him by the door Sweetie," Erin would say to Lexi, usually about 15 minutes before Brad would arrive home. 

When he comes through the door, he is pleasantly greeted by the sight of a submissive and kneeling sissy maid.

"May I please suck your cock Sir?" Lexi has been trained to say, upon Brad's arrival. Sometimes he says no, but it's usually a yes, and he gets a full blowjob to completion, as soon as he gets in the door. 

What a lifestyle!

Brad will grunt and shiver through an orgasm, as bursts of cum ricochet off Lexi's uvula and get swallowed down into his tummy. An appetizer before dinner I guess. 

Brad and Erin retire to the parlour and are served drinks by their sissy maid, while he also prepares a romantic dinner setting for the pair of them.  

Saturday evenings, Lexi gets a little more involved in the sexual activity of this couple, as Brad fucks Erin's pussy, directly over his face. The sissy remains in his chastity cage and still in maid lingerie with heels. It must be dreadfully humiliating, to have Brad's balls bouncing off his nose and tea-bagging his face, as he fucks Erin.

This is one of the few times that Erin allows her sissy to lick her pussy. She just loves the sensation so much, having her clit licked while her pussy is getting railed. The odd time, Brad will dip his cock into Lexi's mouth, to give him more of a taste of Erin. 

Once Brad cums into Erin's pussy, Lexi's mouth is in the perfect position to accept the cascading goo, as it bubbles and oozes from her, directly down Lexi's open hatch. Lexi verbally thanks Brad for his cum, then it's early bedtime. 

Again, just like Friday night, Lexi is dressed in something skimpy, frilly and pink, and is put to bed by Erin and locked into the princess bedroom. 

By 8AM the next morning, he'll be back in the parlour, holding the giant, black cock in his mouth while he waits for Erin to get up. The morning ritual has begun yet again and Lexi will soon be back in their room, holding Erin's panty gusset to the wall and listening to this hot couple have morning sex. 

Sunday morning to be exact. One final day of sissy captivity, before Lexi has to bust out the nail polish remover and return to vanilla life, vanilla, notwithstanding his chastity cage and panty girdles.

Sunday's come with a routine and ritual also, you may even call it...Sunday school.  

Mistress Andrea

xoxo

Continued in: Sissy School

Sissy's morning Ritual

Continued from: Sissy slave to a couple

On Saturday mornings, Lexi's cell door electronically unlocks at 7AM, the exact time his alarm clock sounds. I can picture him waking up in a daze, cloaked by Disney princess sheets and looking down at his sheer lingerie. He would feel his morning erection competing with the rigid bars of his chastity cage and would be feeling the thin band of his thong panties, riding into his ass crack. 

Brad and Erin are undisturbed by their sissy and get to sleep in on Saturday mornings, while Lexi heads for the shower. He is then responsible for doing his own make-up and wig and is required to re-dress in the same lingerie he slept in. 

Any deviation of this morning ritual, would result in severe punishment and likely a month or two added to his next chastity unlock date. 

To compliment Lexi's sissy attire, some strappy heels are provided in his room. Strappy so his toenail polish can pop, a perfect match to his pink outfit. 

Next comes the first of many, major humiliations of the day for poor Lexi. Just outside of his sissy bedroom, in the gentlemen's palour and adjacent to Erin and Brad's bedroom, this awaits: 

The picture doesn't do it a ton of justice as there's nothing to compare the size to, but it's a giant, realistic, black cock. 

Lexi knows what is required of him but is always apprehensive at first. 

Fearful of additional punishment, Lexi continues with his morning ritual. He gets down on his knees and takes the vascular, giant black cock into his mouth and just holds the pose. It's now around 8AM and by the rules that Erin has establish for her sissy, this is the way she wants to find him, when she wakes up. Feminized, denied, humiliated and holding a great big cock between his painted lips.

"Good girl!" Erin will coo to him, when she finds Lexi exactly how she wanted him positioned. 

Yes, in case you are wondering, Erin wears bedroom heels in the mornings, because she's a hottie. 

Erin then releases Lexi and they both click into the bedroom and over to the unwashed laundry hamper. Lexi has to kneel and find the panties that Erin wore yesterday, under her business attire, as Brad watches on. 

Cornertime is far more embarrassing and shameful when you have to hold an object against the wall with your nose. I've seen this done with a coin or with a piece of paper, the shamed individual is under strict orders that they will be harshly punished if the item drops. Additionally, with their nose pressed to the wall, it causes the bum to jut-out nicely and is a good way to present a spanked bottom. 

Erin uses a similar tactic, only her method is a little more devious. She makes poor Lexi open the inner gusset of her panties, the one's she was in all day yesterday, and hold the delicate material against the wall with his nose. 

How dreadfully humiliating for him, and the worst part is yet to come. 

Haunted and enchanted by the lingering scent of his Mistress, Lexi now has to listen to her have sex with her husband Brad. Lexi is under very harsh threats to not let the panties fall to the floor and sometimes his wrists are even cuffed behind his back. 

Painfully, Lexi now hears the unmistakable sounds of a cock being sucked, a pussy being licked and that first audible gasp from Erin, as she takes Brad's entire length into her pussy. 

Poor sissy can do nothing but listen and focus on that panty gusset with all the wonderful scents it captured a day earlier. 

The over stimulus that Lexi was now experiencing, combined with his crushing humiliation and having to listen to Erin and Brad both orgasm, had his little cock straining in its cage. 

Then came the gut-sinking order from Erin, one that Lexi knows well, from having performed this Saturday morning ritual many times before...

"Alexis huni, clean him up," escaped Erin's lips. 

Lexi slowly reached for the panties he was holding against the wall with his nose, still not letting them drop. He folded them carefully and neatly, trying to prolong the inevitable for as long as possible. Eventually, he hung his head in shame and wobbled in his heels toward Brad. 

"May I please clean you off Sir?" Lexi managed to squeak out, before dropping to his knees. 

"Of course," Brad cheerfully replied. 

Erin watched on as her husband guided Lexi's head onto his cock. Lexi cleaned down the shaft of the erect penis with his mouth, sucked a few times and polished each of Brad's balls with his tongue. 

"Thank you Sir." Lexi peeped out, after removing Brad's dick from his mouth. 

Brad began to head for the shower and in leaving, heard Lexi ask Erin, "may I please clean you up Ma'am?"

Once Brad's cum was suckled from Erin's hot pussy and swallowed by Lexi, this officially represented the end of sissy's morning ritual. 

Gawd damn this sounds so humiliating for him!

Could it get any worse? Silly question likely...of course it will. 

Mistress Andrea

xoxo

Continued in: Wait for him by the door