Alice: Through the Looking Glass

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Spanked by Lady Jose

Continued from: Set, Session and Scene

[F/m] [sissy] [spanked for real] [chastity] [pro disciplinarian] 

Exciting development everyone!

For those who have been following along for awhile, several little teasers have been dropped along the way, about a sissy gurl from Belgium named, Alice. This is how Alice spent some of her day today, and this will be the first time she has seen these images of herself. 

I would also like you to meet Malcom: 

Alice and Malcom are the same person, and once upon a time he used to be "male". He had girlfriends, he had sex with a woman once and to this day, holds a PhD in something-or-other and maintains a high-profile career. On today's date, however, he was dressed like a little girl and sent to the corner with a red bum, having just been spanked by an amazing woman. 

How did this happen to poor Malcom? 

Tales of sissy Alice is a blog that Malcom started and currently maintains. If you'd like to know why and how his little penis ended up in a chastity cage for the past 200+ days, he explains it all on his blog.

Alice also maintains a very popular Reddit page that can be found here: Sissy in Denial

On her Reddit page, you will find her daily chastity verifications, her weekly maintenance spanking updates and the attire that she sleeps in, that her "Daddy" makes her wear:

From the image above, it looks like she's going to bed with ME by her side! How cute! Am I worried that Alice is only using me for masturbation fuel? Wanking her little pee pee to oblivion, to images of me? Nope!

This has never been a worry of mine. Alice is not physically capable of even getting an erection, due to her chastity system. She uses an app called Chaster and a 99% secure system of locking, verification codes and a combination lockbox that she cannot see the combination for. Once per week, the app allows her a five-minute window of access to her key. She uses this time to unlock for hygiene and shaving before the key goes back into the lockbox with a new combination. 

Five minutes per week across the span of 200 days, is 2 hours and 22 minutes of freedom in that span of time. When she reaches day 365 locked, that would equate to 4 hours and 20 minutes of penis freedom, out of an entire year. A little too long if you ask me, but I'm not her "owner".  

For an added layer of verification and security, she films this entire process and posts it online. 

If she goes over the five-minute mark in her weekly ritual, even by a second or two, the app will add an additional twelve days to her chastity sentence. 

And if THIS wasn't enough, she has an online "Daddy" who controls this Chaster app as the keyholder, guides and mentors her through weekly rituals, and directs what sort of sexual activity she gets to have with her "boyfriends". Her Daddy is also the one who administers her weekly maintenance spankings and monitors her cornertime. 

Twenty minutes before her spanking and twenty minutes after, once per week. If sissy Alice lived for another 50 years, to age 89, she will have spent 72 days of her life, standing in the corner with her bum bare. Eeeek!

In addition to serving her online Daddy, she is permitted to perform the duties of a Secretary for me. She is the editor-in-chief of my blog stories and is responsible for some cross-page marketing of my blog. If any of you happen to find spelling or grammatical errors along the way, please let me know, as Alice will be in deep shit! 

Here she is in WFH mode, creating a tribute montage of me.  

At some point, Malcom tumbled down the rabbit hole and became Alice. Quite literally, through the looking glass, this is what he sees: 

Alice has been obedient, safe and sane, and has been diligent in her service to me as my Secretary. I thought I'd give her a gift, maybe a life-changing experience she would not have otherwise thought of. A chance to finally get her out from behind the computer and experience something more real. 

She has a fucking machine, she self-spanks for her Daddy once per week, she dresses like a little girl and posts online...but it really can't quite compare to the real thing. 

Alice, this was my gift to you, a simple email: 

Dear Lady Jose, hello. 

I’m Andrea, from Canada. 

I have a distance dynamic with a sissy male from Belgium. We are interested in exploring me sending him to a proper female disciplinarian sort of arrangement, that we would like to become regular, maintenance if you will. 

Just not sure if you do sissy type dynamics and such? 

It would be a pleasure to hear from you at your convenience. 

Andrea 

In a few days, unbeknownst to Alice at this point, I received a reply: 

Dear Andrea,

Thank you for your email. It’s wonderful to hear about the dynamic you share together.

I do offer sessions with sissies, but please note that my sessions are conducted on a professional basis meaning they are paid. My rate is €250 per hour, with a deposit of €50 required, which can be paid via PayPal or Throne.

I’ve also attached my registration form for your reference. Should you agree with the pricing, I would need explicit consent from your sissy before proceeding with any spanking.

Looking forward to hearing from you!

Best regards,

Jose

At this point...actually I didn't know this until today...Lady Jose is an A-lister in the spanking community. There are many female disciplinarians out there, but I had no idea she collaborated with the likes of Sarah Gregory!! (huge girl crush on her)

The entire "Tara Gregory" series in my blog is based upon the legendary Sarah Gregory. That series began here: 

Tara Gregory: Beginnings

Alice, you don't realize how friggen lucky you are! Lady Jose had Sarah Gregory, and now YOU, over her knee! That's insane and I had no idea until I visited Lady Jose's site: 

Book with Lady Jose

Finding a "proper" female disciplinarian can often be difficult. Sometimes the ops starts creeping into the admin, and suddenly there are leather bus-driver hats involved and assless chaps, talks of pegging and worship. This is not what someone seeking a real, old-fashioned spanking wants. That's not what I wanted for Alice. 

We were fortunate to not only find Lady Jose, not only realize that she is in close proximity to Alice, but also, that she replied so openly and welcoming to my initial contact. The next step was to have Alice introduce herself. 

Dear Lady Jose,

It is a pleasure to make your acquaintance.  My name is alice, a 40 year old sissy male living in Antwerp.

I have been instructed by Mistress Andrea to contact you directly regarding the possibility of organising a domestic discipline session should you accept my application.

I have prepared the application form as required and have attached it to this email.  I wish to thank you for the time in reading this application and look forward to hearing back.

Yours sincerely 

alice

The suspense built over the coming weeks, until Alice finally had a date booked and I received this: 

Dear Mistress Andrea,

Tomorrow is the day your sissy and I are going to meet and I am looking forward to it. 

Do you have any preferences for implements I can use on your sissy?

Best Jose

And this was today, what a delightful treat from the remarkable Lady Jose!

Dear Mistress Andrea,

Your sissy is in my corner right now. Alice took the spanking so good and Alice looks so pretty!

I'll share one picture with you but there are more to come

Best Jose

My reply: 

A good 20 minutes should do! Hehe.

Very nicely done, even. I like the white ashy splotches. Was she polite and respectful, Lady Jose? 

Alice was in the timeout corner while this email exchange occurred. I even commented on her hour glasses and how cute those were. I asked her later on if she uses those for cornertime which she does. 

One large, one small...is one of them an hour and one of them a half-hour? What a cool idea! She replied to my twenty minute comment with this: 

Okay 20 minutes!

She is so polite and pretty.

Very respectful.

I’m proud!

Awwww! How sweet. This makes me proud too, as the initiator of all of this and the fact that Alice was a direct representation of me. Additionally proud, now realizing that I was speaking to a spanking A-lister! Omg, Sarah Gregory, I can't even! 

Anyway... 

What a great experience for Alice and I truly hope she sees this as a gift from me. I've asked her to write about this experience for me and I'll post it here for everyone to read.  

And this will NOT be the last time she sees Lady Jose, I assure you! 

Please enjoy watching her in action, a lovely free spanking clip of Lady Jose in some serious F/m: 

Hard Hand and Brush Spanking

Mistress Andrea

xo

Continued in: Mistress Andrea's Gift

The Tears of the Sissies will Water the Meadows of France

Continued from: Tattoos & Tongues

[FFFF/m] [sissification] [forced feminization] [chastity] [forced bi] [humiliation] [spanking] [school]

Hello everyone. I have to take a quick detour from my exploration of newly discovered animations within the Sims. I received a fan request, for a personalized series. I'd like you all to welcome Remy. He is an adult male from France. 

Obviously under consent, he wished his own likeness to be posted for all to see, to shame and humiliate him even more than his outfit would suggest. 

As you can see, Remy is a sissy schoolgirl. His plaid skirt is lifted and panties lowered, to expose a tiny pink chastity cage, housing an even tinier little clitty between his legs. This is the style of dress he prefers to be in, rather than his boring male clothes. 

Look at the two little dimples on his back, just like a girl! It's called "Britney Spears back", Remy. And all the men enjoy seeing these little dimples, when they take you from behind. Very visually delightful and feminine in the timeout corner too!

From his pigtails to his knee socks, it looks like he has everything, with the exception of Mary Jane heels. He will remedy this very soon.

After my last post, Remy left me a comment on the blog that read: 

Hello Mistress.
I am a sissy slave schoolgirl from France who wears a chastity cage.
Could I become a character in your stories please
I would like to be enrolled in your school for girls and be required to wear the same uniform as the other students
I would follow the same training as the other girls and I would also be punished

I think we can accommodate this request. Maybe a little foreign exchange student program for him, but the only option available is an all girls school?

I need to first put together the perfect team of minions to ensure he has the "proper" experience during his time with us. 

Nancy Landgraab, remember sweet Nancy, the oldest of my clients? Perhaps she could provide a more "senior girl", maternal and caring approach to Remy's time with us, while holding the authority to discipline him also, like the den mother of the group? 

We now have an AI version of Nancy. What do you think...pretty close? 

And I know she can pull off the schoolgirl look. I have spanked her over my knee many times while she's dressed like this: 

My wife, Summer! Obviously. She's from Paris. We totally need her to be involved, so she and Remy can conspire, commiserate and giggle in their native language, behind the teacher's back. 

We all know that she can rock the schoolgirl look too! 

Then, we need a wildcard in the mix. Someone who could go completely off script and just do whatever. Usually this role is filled by Cassandra, the wildest of them all, but alas, Cassie is unavailable for Remy's visit. 

Maybe that Carley girl? Remember her? That mousey, tattooed little thing? If her Dominant, Robby, lets her, then perhaps she could come play with us? I'm pretty sure she would have a gothy, schoolgirl uniform in her wardrobe somewhere. 

Robby will have to let us know if Carley can come by for a playdate. 

As for you, Remy, it would appear the stage is set for some deep humiliation, severe discipline and continued denial. You can expect your submissive stay with the girls and I to be absolutely miserable!

How do you put it, Les Misérables?

Mark my words, the tears of the sissy will water the meadows of France!

Mistress Andrea

xoxo  

Continued in: Dream Team

 

Husband gets Blacked

Continued from: "Thank you for fucking my wife"

Derek's stomach twisted with repulsion and humiliation, as his tongue diligently explored the vascular surface of Anthony's cock. Vanessa stood close-by, ensuring her sissy husband cleaned all remnants of her tangy pussy from Anthony's cock and balls. Derek's embarrassment had reached a pinnacle of emasculation, or so he thought. With no safe-words spoken from her delicate sissy husband, Vanessa took this as a queue to continue her relentless torment. 

"Stand and curtsy to Anthony please honey, thank him for letting you clean me off his beautiful cock," Vanessa cooed to Derek. "And address him as Daddy!"

Derek stood in his elaborate sissy attire, the layers of ruffles and bows a visual representation of his vulnerability and submission. The room seemed to hold its breath as he performed his embarrassingly dainty curtsy and whispered, "thank you Da...Daddy. Thank you for letting me clean your cock." 

The corners of Vanessa's villainous lips curled into a devious smile, watching her husband struggle through such intense humiliation. Yet, she knew little glossy strands of pre-cum would be oozing from his chastity cage and wetting the front of his delicate satin panties. 

Vanessa then turned and spoke to Anthony. "I'm going to change into a little something for you my lover. Can you take my husband upstairs and spank him for me? On the bare please. I want him nice and red before you fuck him." 

Derek's mouth went dry and his hands began to tremble. The gauntlet had just been laid out by Vanessa, as to what the rest of the evening would entail. His heart pounded in his chest as he carefully negotiated the stairs in his darling Mary Janes. 

Anthony waited for a safe-word to escape Derek's painted lips and left enough time for him to protest or tap out of the scene. Upon hearing neither, Anthony continued where Vanessa left off. 

"Dress off and panties off young lady. Park your nose in the corner. Daddy will be up shortly." 

Anthony's deep voice reverberated through Derek, causing his bottom lip to quiver as he tried desperately to fight off tears. 

Derek took a deep breath and exhaled with a sigh of humility and sexual frustration, as he caught his own reflection in the vanity mirror. His gaze caught site of his flaccid penis, trapped behind the metal bars of chastity. This caused Derek's mind to turn quickly back to the giant penis he recently had in his own mouth and the way it tasted of his wife's arousal. Derek's mouth began to water slightly, as he reflected on Anthony's glistening cock.  

After spending a little too long at the mirror, mesmerized by his own transformed reflection, Derek suddenly heard heavy footsteps ascending the stairs. He quickly rushed to the corner, as Daddy had instructed. He certainly didn't want to face the consequences of being out of position when Daddy entered the room. 

The floors creaked behind Derek, letting him know that Daddy was now in the room and witness to his dreadfully vulnerable state.

 

"Well young lady," Anthony spoke sternly. "You heard your wife, get across my lap." 

Derek shamefully shuffled toward the couch, no longer having the protection of panties to conceal his "clit cage". The culmination of all the night's embarrassments, frustrations and humiliations had finally brought Derek to his breaking point. He froze in his tracks and began trembling and bawling his eyes out, desperately pleading with Anthony.

"Please Daddy, don't spank me!!!"

"I'll put out for you Sir, I will! You don't need to spank me!"

Derek's degrading pleas for mercy continued, as Anthony's muscular hand grabbed onto his wrist and man-handled him across his lap. 

Derek's shameful blubbering continued, as the first of the heavy smacks began. 

"Please Daddy, noooo....don't do this!" He cried out. 

Amidst the commotion of pleas and heavy slaps, Vanessa clicked into the room, just as her husband was mewing out a very degrading, "I'll put out for you Daddddddddy!"

"Is that so sissy?" Chimed Vanessa. 

"Show me..." She hissed. 

The defeated and reddened Derek, delicately took Daddy by the hand and led him over to the bed. Vanessa joined the two so she could continue to reassure and coach her husband.  

"Derek," Vanessa's voice was both commanding and nurturing, "I want you to begin by undressing Daddy, slowly and deliberately. Pay attention to his reactions and his desires."

Derek's heart raced as he absorbed Vanessa's instructions, his emotions a mix of anticipation and vulnerability. 

"Once you have undressed Daddy," Vanessa continued, her voice steady, "focus on his pleasure. Attend to his needs, ensuring that he is comfortable and satisfied. It's your task to get Daddy nice and hard for you sweetie. Once he is, you can offer him your bum." 

With a mix of humiliation and embarrassment, Derek followed Vanessa's instructions, slowly turning around to face Anthony on his hands and knees. He felt a shiver of vulnerability as he presented his asshole to Anthony, fully embracing his role as a submissive sissy eager to please.

Vanessa watched with delight as Derek assumed the position, his frilly socks and shiny Mary Janes emphasizing his femininity. "Good girl," she praised, her voice dripping with approval. "Now, wiggle your bum and ask Daddy to fuck you like the sweet little sissy you are."

Anthony, now fully aware of Derek's willingness to submit, stepped closer to him. His hands gently caressed Derek's smooth hips, tracing the contours of his delicate frame. The touch sent shivers down Derek's spine, and he couldn't help but let out a soft whimper of anticipation.

Vanessa remained by Derek's side, offering soothing words of encouragement. "Relax, my sweet sissy," she whispered, her fingers gently running through his hair. "Take Daddy's dick into your bum, just like a girl.”

Anthony couldn't help but chuckle at the sight of Derek's locked-up genitals, dangling helplessly beneath him as he obediently wiggled his spanked ass. The contrast between his own fully aroused manhood and Derek's chastity cage was stark and visually striking. It only further emphasized Derek's submissive position and his complete surrender to their desires.

Vanessa, who was watching the scene from the bed, leaned in and whispered in Anthony's ear, "Look how desperate he is for release. That locked-up penis is dripping for you my lover."

Anthony grinned, fully aware of the power dynamics at play. He stroked Derek's exposed bottom, teasing him before gently sliding a finger along the outline of the chastity cage. Derek let out a soft moan, torn between the desire for release and the thrill of being under their control.

"You must be craving release, my little sissy," Anthony said with a playful glint in his eyes. "But you know you won't get it until we say so."

Derek could only nod, the intensity of the situation overwhelming him. He was aching for release, yet the chastity cage reminded him of his role as a sissy, denied of conventional pleasure but rewarded with penetration, just like a girl. 

Vanessa interjected, her voice filled with authority, "You're not here for your pleasure, sissy. You're here to please Anthony and me. So, show us what a good fuck-doll you can be."

Derek's heart raced as he felt Anthony's cock pressing against him, seeking entrance. He braced himself for what was to come, ready to submit fully to their desires and become a vessel of pleasure for both of them.

("Seeking entrance". Well done Chatty!)

Vanessa, being the Goddess that she is, masturbated on the bed while listening to the symphony of grunts and pleas coming from her husband. 

"Please Daddy just slow down. Oh god Daddy it's so big." Derek was bawling out into the room. 

After several toe-curling orgasms for Goddess Vanessa, she stood back to witness the dramatic climax of Anthony shooting his hot cum into her husband's ass. It was a beautiful sight to watch. Derek was truly a Queen of Spades now. 

Two things became clear after this wild night. 

I doubt Derek will ever again have conventional sex like a "real man"... 

...and Goddess Vanessa was my new fuckin' hero!

Oh boy I have a girl-crush. Just look at her! 

Mistress Andrea and "Chatty"

xoxo

Continued in: The Cum Brat