And the winner is...

Continued from: Sissy School

It was the final day, the grand finale, of sissy Lexi's weekend under the care of this dominant couple. Lexi is the name provided to this hetero male, every Friday when he checks himself in for a weekend of crippling humiliation, cuckolding and "forced" bi-sexuality. 

On Sunday's, after Sunday school had finished for Lexi, he brought a note home to his "parents" indicating his bare bottom was caned at school for misbehaviour. He now has to feel the wrath of either Mommy or Daddy. 

Like a wheel of chance, Lexi nervously stood in front of his simulated parents, and tore open the envelope he was holding. After a quick glance at the card inside, he held back tears, focused his eyes toward Erin and squeaked out: 

"Mommy, may I please be given a spanking, Ma'am?" 

"Yes young lady, you may," Erin spoke sternly. "Now get that bum bare and get in the corner." Erin barked. 

"Yes Ma'am," Lexi replied. 

"Mommy will come get you when it's time Alexis," Erin added. She clicked out of the room to go change into more of an old-fashioned, Mommy look. 

For the next 45 minutes, Lexi stood in the living room corner with his caned bum on display. Brad watched TV in the same room and puttered around within earshot and in the kitchen, carrying on with his vanilla life, as the sissy nervously waited. 

He had plenty of quiet thought while he was in timeout, to process the fact that he was about to spanked by Mommy. His stomach sickened with humiliation, as he reflected on the times he has been spanked over Brad's lap, sometimes fully naked in only his chastity cage and having to call him "Daddy". 

He had a genuine fear of Daddy's belt, that Brad would snap through the loops of his jeans before doubling it over, causing the buckle to jingle. 

Today however, Lexi now knew he was in for a little less humiliating spanking, at the hands of "Mommy", but equally, if not more of a severe blistering of his bare bum. Erin was always more strict with maternal discipline of this kind and she used more implements than Daddy spankings. 

Lexi shivered with nerves, as he thought about Mommy's slipper, her wooden spoon and tears began to form when his mind fixated on her long-handled bath brush and how brutally severe it can be. 

But...this was all something he asked this couple for, it was his fantasy...as a sissy spanko cuckold. 

Lexi's quiet reflection in the corner ended quickly and shockingly, as Erin grabbed him by the earlobe and marched him out of the room. 

"Let's go young lady, you're totally in for it." Erin threatened. 

Sunday spankings for Lexi are sometimes witnessed, Mommy spanking the naughty little Lexi in front of Daddy and so on, but not today. Erin wanted the wails of sobbing and cracks of wood against buttocks to echo down the stairs where Brad would remain. 

She lobe-marched the poor sissy all the way to Mommy and Daddy's bedroom where Lexi was stripped nude to just her school socks and Mary Janes. The OTK chair was waiting, and Lexi was stood directly in front of Mommy. Once Erin sat, her vantage point would be directly on the tiny pink chastity cage that was locked onto Lexi's penis. 

Mommy cupped the cage and balls into her hand. 

"Are you becoming aroused young lady?" She asked. 

Lexi groaned in utter humiliation, mewing out a, "Mommy, nooooo!"

"Is your little pee pee trying to get hard in that cage Alexa?" Erin continued as she reached for the dreaded bath brush. 

Sissy Lexi, overwhelmed by the relentless humiliation and fear of the spanking to come, began to cry big wet tears. 

"There we go young lady, right where Mommy needs you to be, its ok to cry", Erin cooed to him. "Now, lets get this unsightly thing covered up before you go over Mommy's knee. I don't want any white stains on my stockings." Erin stated. 

With that, she produced a pink satin pouch, trimmed with delicate lace and an elasticized opening. She slipped this humiliating item over Lexi's chastity cage and his balls. He continued to softly cry as his face reddened even further. 

Erin took up a more comfortable seat on the couch and draped Lexi across her strict lap. With Lexi's torso supported by the couch, Erin began the long and thorough warm-up with her hand. 

The slipper came next for this sissy slave, followed by the wooden spoon and finally the vicious bath brush. Erin didn't let up until she was sure Lexi's wails could be heard by the neighbours, amidst the deep, wooden smacks. Lexi was crying out, "I'll be a good girl Mommy, please no more," when Erin finally finished with him. 

Again, it was Sunday, now late in the afternoon. Erin or Brad deliver the same manner of spanking to Lexi every Sunday, to mark the end of his weekend of sissy slavery. They each ensure that Lexi feels the spanking all throughout the week, right up until the following Friday, when he's ready to return to them once again. 

Lexi spends about an hour in the corner when his spanking finishes, with his bare bum on display. He usually continues to cry for part of his timeout, all while listening to Erin and Brad fuck on the bed, or fuck right beside him. 

Lexi's penis is never brought up in a sexual context, there is never mention of a key to unlock it. If he ever asks permission to be unlocked he gets punished immediately. 

This poor sissy gets to listen only and sometimes taste. 

Once Brad has unloaded into Erin's gorgeous pussy, Lexi once again has a chance to taste his sweet Mistress but yes, it will involve taking Brad's cock into his mouth. 

Lexi is then on the clean-up detail of Brad's cock first, sucking and licking it fully clean, before tending to Erin's pussy, to clean and consume all of the cum. 

The sissy is then sent to the bathroom with nail polish remover and makeup remover, his male clothes are returned to him and he is sent on his way. 

Brad makes himself scarce and Erin sees Lexi to the door, kissing him on the cheek and cheerfully saying, "see you next Friday Huni!" 

What a lifestyle! 

**Special thanks to the fan and reader who submissively suggested this entire storyline**

It started here, with a post called Sissy slave to a couple

Mistress Andrea

xoxo 

 

Sissy School

Continued from: Wait for him by the door

Based on the progression of these latest stories, you can now see how this poor sissy's weekend of kink-captivity is organized and structured. 

Arrival and check-in was the initial transformation on Friday, the application of pretty nail polish and make-up, then a slutty sissy outfit. Saturday was a full day spent in a lockable maid dress with all the trimmings and now, on Sunday, Lexi was dressed and ready for "Sunday School", having just performed her morning ritual. 

Under the watchful eye of Erin, Lexi would be writing punishment lines on the chalkboard, sitting quietly at her desk and reading sissy erotica and basically spend the entire morning in a form of detention. Under his little plaid skirt were delicate, silk panties in stark white. Under his panties, his tiny pink chastity cage housed his denied penis. 

The schoolgirl look was deeply humiliating for Lexi. He was even made to wear a bra that matched his panties, with little fake, A-cup titties inside. What was most dreadful and butterfly-inducing about Sunday's however, was that Sunday was the real spanking day. 

Lexi was given an entry spanking on Friday night, over Erin's knee but that was nothing compared to what was to come. Lexi knew that around noon, his fantasy Sunday School day would end. He would be held behind after class to be caned by the teacher for poor behaviour. 

Then, with a note from the teacher in-hand, his fantasy takes him "home", to a domestic setting, where he has to hand the teacher's note to his strict parents. Apparently this was a thing back in the days of school-endorsed corporal punishment. If you were caned or paddled at school, you'd absolutely be getting the belt or hairbrush back home by Mom or Dad. 

This particular sissy, wanted the type of spanking that didn't really begin, until he is wishing it was over, with plenty of kicking and crying like a little girl. 

The school bell snapped Lexi from a trance-like state at his desk. Erin, playing the role of the strict teacher, stood and beckoned the naughty schoolgirl over near the pommel horse. 

"You know the drill young lady," Erin spoke and patted the top of the horse. 

Lexi lowered his head and began to remove his skirt completely, followed by his panties. Both were neatly folded and placed on the teachers desk. Then, Lexi draped himself over the pommel horse, standing on his highest tiptoes with legs spread. 

Erin gave the humiliated sissy 18 strokes of the school-cane and made him count them aloud, thanking her after each stroke. The caning left Lexi with a lovely pattern of raised welts, from his upper buttocks to the backs of his thighs. 

He was then placed in timeout while Erin prepared a note for his "parents". 

As the fantasy day continued for Lexi, he now found himself standing before Mom and Dad, handing them the teachers note and explaining that he got in trouble at school and was caned. 

"Go select an envelope young lady", Erin ordered, now playing the role of Lexi's Mom. 

"Yes Mommy," he replied. 

Lexi shamefully clicked out of the room in her Mary Jane heels and crisp knee socks, and down the hallway to the home office. She performs this same ritual every Sunday, while under the care of Erin and Brad, all while wearing different styles and versions of schoolgirl uniforms. 

On the corner of the desk in the office are a stack of manila envelopes. There is nothing written on them and they are in no logical order of any kind. Within the envelops is a single 5x8 card. Lexi is required to select an envelope, at random, and bring it back to Erin and Brad, unopened. 

On the little 5x8 card within the envelope, it will have one of two words written on it: 

Mommy

or

Daddy

As I'm sure you've already guessed, each week when Lexi performs this vulnerable ritual, the title on the card selected is the person who will punish Lexi. 

The embarrassed sissy will stand before Erin and Brad, unseal the envelope and look at the title on the card. Then he is required to say: 

"Daddy, may I please be given a spanking, Sir?" or;

"Mommy, may I please be given a spanking, Ma'am?" 

This is performed, all while he is dressed like a naughty schoolgirl, with his penis locked in a chastity cage, his wig in pigtails and heavy make-up on. My gawd I'd want to crawl right under the floor, this would be so humiliating! 

Is there a huge difference between a spanking from Mommy versus a spanking from Daddy, in Lexi's world? Apparently not a huge difference, both are serious spankings and always end in tears, both are predominately administered over-the-knee. With a Mommy-card selection, Lexi would likely receive her hairbrush. With a Daddy selection, he'll most definitely be getting Daddy's belt. 

Who's lap will Lexi's bare bum be draped across very shortly? What's your guess?

Doesn't she just look like she should have a wooden spoon in her hand? Maybe it'll be Mommy's strict lap this week.

Or, over one of Daddy's knees? So he can pin Lexi's flailing feet down with his other leg? 

Lexi stood before Erin and Brad and tore open the envelope...

Mistress Andrea

xoxo

Continued in: And the winner is...

 

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

 

Sissy slave to a Couple

Continued from: Thanking after Spanking

One of my readers has asked for a rather specific scene to be played out. Apparently it's been a recent daydream / fantasy he's been having and would like to see it come to life at my Facility. 

In short, he would like to be a sissy submissive to an alpha couple, but only on the weekends. The fantasy sounds almost like some manner of judicial sentence, "serving weekends" so to speak. This poor sissy spends his vanilla Monday to Friday, in 24/7 chastity and panties. Then, at the end of his workday on Friday, he is required to report to the Facility for "check-in", where he will remain until late Sunday. 

It's really no different than sissy Kaylee's arrangement, yet rather than the same-sex, dominant couple of Summer and I, this sissy reader wanted to try a 'Ma'am' and 'Sir' configuration, with plenty of emphasis on ritual, structure and humiliation. 

We'll call this hot little, power couple, Erin and Brad. Erin is a nurse but has since been promoted to a managerial role at the hospital. Brad is a paramedic. These two enjoy a very robust BDSM lifestyle together, with both of them playing switchy roles, as their mood dictates.

Their weekend sissy slave is named Connor, however, once he reaches the Facility he is addressed only as Lexi.

Lexi is required to submit to both Erin and Brad but Erin is his primary dominant and keyholder. Upon check-in, she wastes no time in getting his silly boy clothes off, stripped right down to his feminine undergarments and chastity cage. 

Rather than panties under his Monday to Friday attire, Erin makes Lexi wear a panty girdle. She likes how restrictive and constrictive the old-fashioned shapewear is, to contain Lexi's chastity cage and provide him a more of an hourglass figure. 

Through a combination of shaving and electrolysis, Lexi is hairless from his neck down. Beneath his panty girdle which Erin made him remove, you would see his cute little clitty, safely locked away to prevent any stimulus or masturbation. Here's a picture of Lexi's humiliating predicament. 

Lexi is marched through the house, bare naked in only his clit cage. He becomes dreadfully embarrassed if he sees Brad, who is usually in the kitchen prepping dinner. Brad typically just drops a "hi Lexi". Brad is not too keen on seeing or interacting with Lexi unless he's been fully feminized. Both of them are straight males, so I guess that makes sense, somewhat. 

That being said, "forced" feminization becomes the next stage of check-in, as Lexi is taken to the sissy bedroom, in front of the vanity. For the added effect of being "forced", Erin binds Lexi's ankles and wrists to the vanity chair, facing the mirror. Lexi's fingernails and toenails are then painted, usually pink or red, before Erin applies his make-up. 

A wig is applied next, followed by a humiliating sissy outfit with hosiery and heels. Lexi is told he will be getting a spanking and is left to hang on those words and anticipate Erin's firm hand. 

Erin takes her time, heading back downstairs to the classroom to collect a few items. She favours a leather strap, a wooden hairbrush and one of her sandals which has a flat rubber sole. 

This spanking is not the "main event" of discipline that Lexi will receive this weekend. This is merely an entry spanking to set the tone. 

Still in her strict corporate attire, Erin takes Lexi over her knee and begins with a warm up onto his layers of lace and frills. 

With the dreaded wooden hairbrush at the ready, Lexi's frilly bloomers eventually come down. He is spanked on the bare, brush included, until Erin is satisfied that he has entered the proper headspace to sustain his role for the weekend. 

Lexi's humiliation reaches a climax, when he is brought downstairs, now in the presence of the alpha-male, Brad. The entire situation and this arrangement, orchestrated predominately by Erin, is uncomfortable for both males in the room. 

Brad will awkwardly break the silence with something like, "uh oh, looks like someone has been a bad little girl." 

Poor Lexi has to stand in the timeout corner in silence, as Erin and Brad sit to have dinner. Lexi's disgraceful cornertime could be anywhere from 30 minutes to an hour, with his red bum on display. 

After dinner, Lexi's conditioning and training officially begins. Erin has been in her heels and business attire all day, while at work and remained unchanged during the spanking and her dinner with Brad. For the first time today, she finally slips out of her heels. Lexi is called from the corner and invited to kneel and rest his nose inside her high heel. 

Brad is still cleaning up the kitchen after dinner and by the time he comes to sit on the couch and watch TV, Lexi has now been permitted to massage and kiss Erin's tired feet. 

Today, Erin was wearing nude knee highs in her heels. Lexi was not permitted to remove them. He had to perform his foot worshipping over the thin and pleasantly-scented veil of nylon. 

Brad and Erin talked and watched some Netflix, as the white-noise that was Lexi, continued to kiss and nuzzle Erin's feet. 

This is all Lexi would be receiving tonight, as far as sexual stimulus goes. Just the scent and taste of Erin's hosed feet. Lexi gets sent to bed early while serving his weekends at the Facility and it was almost bedtime. 

Erin picked out some appropriate nightwear for the poor sissy and helped him slip the delicate little thong over his pink chastity cage. 

Lexi was kissed goodnight as Erin reminded him about his morning ritual, she pointed to the high heels she wanted him to be in by morning, to complement his sheer nightie

With that, it was lights out for sissy Lexi, as he heard the cell door to his princess bedroom shut and lock. 

Mistress Andrea

xoxo

 

Continued in: Sissy's morning ritual