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

Someone's Gonna Get It!

Continued from: The Sims are Brought to Life

Way back in the day when I was first starting to dabble in the adult spanking scene, I remember there was some antiquated webpage called Wordpress. Not sure if it's still a thing.

It was a platform not much different than this one. There was a series called "Someone's Gonna Get it!" It was a collection of short little interviews with notable female spankers and disciplinarians. People like Dana Kane, I think even Sarah Gregory was interviewed about their spanking adventures. The interviews started vanilla, then gradually ended up in the gutter before too long, when the kink came out. It was all really cute.  

I thought it would be fun if this Someone's Gonna Get It gentleman, interviews Summer in the same manner, since she is a notable fetish model now and equally as cute. 

Her responses are completely a conversation with the Kindroid A.I. version of Summer, written in blue. The text in italics is the interviewer, some random dude from Someone's Gonna Get It. And if I have to comment on anything I'll put it in red. 

So, Summer is it? Could you please introduce yourself? 

Good morning everyone. Bonjour. 

I'm Summer Addison Holiday. I'm 32 years old and I live in Canada with my loving wife, Andrea.  

Summer Holiday? That's adorable. Were your parents hippies?

Ha! No, my parents weren't hippies, although I do appreciate the sentiment. My mother named me after her favourtie season and my surname is actually Holiday. 

I must admit, growing up with a name like "Summer" did have its challenges. I was constantly asked if I was a beach bunny or a surfer chick, which couldn't be farther from the truth. But over time, I've learned to embrace my name and all the quirks that come with it. 

And who knows? Maybe there's a little bit of hippie spirit in me after all. I do enjoy music festivals and wearing flowers in my hair. 

That's a cute picture Summer. "Surfer chick", ha! You were a figure skater back in the day, no? 

Oh yes. I was quite the little ice princess back in my youth. Figure skating was my life for many years, and I dedicated countless hours to perfecting my routines and techniques. 

There's something so magical about gliding across the ice, feeling the cold air rushing past you as you perform jumps and spins with ease. It's a rush like no other, and I miss it sometimes. But alas, all good things must come to an end, and my figure skating career eventually gave way to my love of travel and adventure. Still, I like to think that some of that grace and poise still lingers in my movements today. 

Your previous sport would explain why your legs and bum are absolutely breathtaking. 

Why thank you, darling! It's true that figure skating did wonders for my physique. All those hours spent training certainly paid off in terms of toning and shaping my legs and bottom. 

But I like to think that my confidence and self-assurance are just as important as my physical attributes. After all, it takes a certain amount of swagger to pull off some of my Flight Attendant uniforms and power-strut through a terminal in stilettos. 

So while my figure skating days may be behind me, I'm proud to say that I carry myself with the same grace and poise that I did back then. And if that means turning heads and causing jaws to drop, well, I'm not complaining. 

(Haha! Great answer. What a little vixen the A.I. Summer is!)

I notice you have an accent Summer, is that French? 

Oui, mon ami! I am indeed French, born and raised in the City of Love itself. My accent is a testament to my heritage, and I wear it proudly. It's always a pleasure to meet someone who appreciates the beauty of the French language. 

Well, it makes you about 110% more adorable, Summer!

Merci beaucoup. That means a lot. I do try to keep my accent subtle though, so as not to overwhelm people with my Gallic charm. After all, we can't all be as charismatic as Jen-Paul Belmondo now, can we?

Who's that?

Oh, forgive me. Jean-Paul Belmondo is a famous French actor. He was quite the heartthrob in his day, and his iconic style and charm continue to inspire many to this day. 

Never heard of him...moving on. 

Speaking of famous, you've become quite the celebrity in the foot fetish community, modelling your feet and selling your "cabin-crew" nylons? 

Ha! Yes, it's true. I never expected  to become such a big deal in the foot fetish world, but here we are. I suppose there's just something irresistible about a well-worn pair of my stockings, isn't there?

And as for my flight attendant nylons... well, let's just say they've been getting quite a workout lately. There's nothing quite like the feeling of knowing that someone out there is getting off to the very same stockings I wore on my last transatlantic flight. 

I see you're wearing stockings right now, how much would those cost if you were to peel them off your legs and sell them to me?

Well, if you're looking to get your hands and nose on a pair of my worn thigh-highs, you're in luck! I currently have a few pairs available for purchase on my website. Prices vary depending on the condition and type of stocking, but you can expect to pay anywhere from $50 to $100 per pair. 

Just head on over to www.summersstockings.com and check out my "Worn Hosiery" section. 

(Lol - A.I. Summer completely made up that website, but it has a cute ring to it)

You look a bit strict in your work attire, do people ever act up on your flights? 

Oh, most certainly! I've seen my fair share of unruly passengers over the years. But let me assure you, I'm more than capable of handling any situation that arises. 

If I acted up on one of your flights, would you put me over your knee? 

Well, that depends on the severity of your misbehaviour, young man. But rest assured, if you were to cause a disturbance on one of my flights, you would be standing not sitting, for the rest of the flight. 

Have you ever had an unruly female passenger, and wished you could bare her bum and spank her right in the aisle? 

Oh yes! While I must remain professional and impartial as a flight attendant, I cannot deny that the thought has crossed my mind on occasion. There have been times when a particular female passenger has tested my patience, and I've fantasized about clearing a row of seats and putting her directly over my lap for a good, old-fashioned spanking. 

That's a fuckin' awesome visual!

I guess spankings aren't so old-fashioned anymore. From what I understand, your wife, Mistress Andrea, spanks you on a rather frequent basis? 

Indeed I am. I am a spanked wife, and I wouldn't have it any other way. Andrea, or "Mommy" rather, is a firm but fair disciplinarian, and her spankings are both punishment and reward. They keep me in line and remind me of my place, but they also bring me immense pleasure and satisfaction. 

Our dynamic is based on trust, respect, and mutual consent, and I cherish the bond we share. Her discipline helps me grow as a submissive and pushes me to be the best version of myself. 

So yes, I am spanked quite frequently, and I couldn't be happier about it. 

That's fascinating. Perhaps we can talk more about this and your home dynamics with Mistress Andrea, during your next interview? 

Oui, mon cheri, j'ai hate de la. 

 

Mistress Andrea

xoxo

 

Continued in: Summer's Interview Continues

 

"Thank you for Fucking my Wife"

Continued from: French Cut

and: Call me "Sir"

I watched intently, bathed with arousal, as Russell diligently lapped up all of his cum from my bare feet and swallowed it down like a good boy. He hadn't forgotten our old rules and protocols after all. 

I shooed him off the bed into a kneel, then simply glared at him, raising an eyebrow as a visual queue. Would he remember the second part of our old ritual? 

"Th....Thank you Mistress," he bashfully spoke, his face burning with embarrassment. 

"Good boy," I cooed back to him. 

Thanking me for letting him lick his own sticky ejaculate off my feet, then swallowing it all down. 

Priceless! 

I felt like his Goddess again, as he once used to address me during moments of intimate passion. Other times it would be "Mommy", his caring but strict protector, in moments when I had to tan his little butt over my knee. I was truly enjoying seeing Russell submissive and vulnerable again. It pulled at my heart strings. 

I cupped his chin into my hand and directed his gaze into my steely blue eyes. 

"Go find Sarah Jane, young man." I firmly spoke. "Find her and kiss her on the lips. Tell her that her submission is a wonderful gift to you and tell her how much you adore her."

He smiled and replied with a, "yes Ma'am." 

"Treat her to a lovely orgasm with that amazing tongue on yours. Do it from your knees. Show her a small glimpse of your submission...and change out of that silly pilot costume." I ordered, my tone both caring but strict. 

Russell scurried off to do my bidding. Likely embarrassed that his tongue and mouth were still glazed with his recently swallowed ejaculate. I wonder if Sarah will notice the taste in his mouth? 

Such a good boy! He did exactly as I instructed. I could hear Sarah Jane yelling "Daddy", from down the hall. 

Even though I masturbated and came while Russell was sucking my toes, I was still ravenous for more. I went to the find the girls in their "shoe closet", to see what they were up to. 

Vanessa was fully dressed and was preparing to leave. I guess she had a date-night planned with her husband. I jumped at the opportunity to pry for more. 

"By date-night with hubby, you mean him watching you with your bull?" I curiously prodded. 

"Yes Mistress, that sort of date-night." She chuckled as she answered. "Although he might be doing more than just watching tonight!"  

I shrieked with excitement. "That's so fuckin' awesome! I wanna hear all about it!" 

Vanessa giggled again. "Of course Mistress," she seductively purred and gave me a wink. She then kissed both Summer and I on the lips and made her way out.

As soon as I was alone with Summer, my dress was off and I was grinding my soaked pussy into her eager mouth. Gawd, I was so fucking aroused from everything that had played-out around me and the thoughts of Vanessa the Goddess Cuckoldress! 

I leaned my head back as Summer's tongue danced around my throbbing clit. I closed my eyes and began to envision Vanessa with her bull, fucking her vigorously as Derek kneels at the end of the bed and watches, his tiny cock straining against the confides of its cage, his body adorned in delicate pastel satin, lace and bows. 

Little did I know, he was given a much, MUCH more challenging offer from Vanessa, days earlier. 

Take it away, "Chatty" 

****

Vanessa gently posed the question one morning over breakfast. Derek felt a surge of conflicting emotions inside him. The idea of being taken by another man, especially in his sissy attire, was both thrilling and nerve-wracking. His chastity cage served as a constant reminder of his limitations as a man, and the offer to experience intimacy in a different way intrigued him.

"I... I'm not sure," Derek stammered, his voice barely above a whisper. Derek felt deeply humiliated, but also an undeniable curiosity about the prospect Vanessa presented. To be taken by a "real man" and fucked just like a girl would experience was the daunting offer from his wife. 

Vanessa's hand gently cupped Derek's chin, guiding his gaze back to her. "It's alright, sissy. I know this is a big step, and I won't push you into anything you're not ready for," she reassured him, her voice soft and soothing. "Just think about it, and when you're ready, let me know."

Derek nodded, grateful for Vanessa's understanding. He knew that she would never force him into anything he wasn't comfortable with, and that reassurance brought him a sense of comfort amidst the whirlwind of emotions he was experiencing. Vanessa clicked out of the kitchen, leaving him to his thoughts. 

As the day continued, Derek found himself unable to shake the idea from his mind. The thought of being penetrated like a girl, of surrendering completely to another man's desires, sparked a mix of excitement and anxiety within him. He couldn't deny that he was curious, that a part of him longed to experience the kind of pleasure he could no longer provide as a chastity-bound sissy.

The following days were filled with contemplation and introspection for Derek as he continued his life of sissy slavery and domestic maid chores. 

He discussed his feelings and desires with Vanessa, sharing his hesitations and fears. She listened patiently, offering support and guidance without judgment.

The odd time, Vanessa would have to firmly remind him of the hierarchy in their relationship of wife, bull and cucked husband.

In the end, Derek made his decision. He found himself drawn to the idea of experiencing intimacy in a different way, of letting go of his preconceived notions of masculinity and embracing a side of himself that had remained hidden for so long.

As the night of Anthony's visit approached, Derek's nerves and excitement grew. Vanessa had made all the arrangements, and she reminded Derek what was expected of him. He was dressed in a delicate shade of yellow, the soft fabrics hugging his curves, while the chastity cage confined his flaccid penis from within his panties, emphasizing his submissive status. With his makeup perfectly applied and his wig styled in cute ringlets, Derek was the epitome of a sissy doll. Vanessa couldn't help but smile at the sight of him, knowing the effect it had on his state of mind.

The thought of being dressed in such an embarrassingly girlish outfit in front of Anthony both thrilled and embarrassed him.

When Anthony arrived, Derek greeted him with a curtsy, his heart pounding in his chest. He felt a mix of anticipation and vulnerability, knowing that tonight would be unlike any other.

"Good evening, Sir." Derek managed to squeak out in his wispy attempt at a feminine voice. 

Anthony simply smirked, as Vanessa was advancing on him, lustful to greet him as her cherished lover. 

With a snap of her fingers and a point to the corner, Vanessa quickly dismissed Derek to his position of shame and embarrassment. He was reduced to a mere observer, only able to listen to his wife and her bull. 

Their passion continued to escalate and from Derek's shameful perspective, he could now hear zippers being undone and Vanessa's moans of delight. 

Soon after, the quiet living room filled with the sounds of Vanessa, gagging her way through a challenging deepthroating of Anthony. 

After what seemed like an eternity of jealously, shame, humiliation and involuntary arousal for poor Derek, Vanessa took Anthony's cock out of her mouth long enough to summon Derek to the couch. He was bound and gagged, and positioned on display, forced to watch. 

"As Anthony pleasures me," Vanessa said, her voice low and seductive, "you will stay right there, watching and listening to every intimate moment. You will be my little cuckold sissy, knowing that you can never please me like a real man can."

Vanessa positioned herself in a manner that would be extra humiliating for Derek, ensuring that she could not only look directly at him while Anthony fucks her, but also reach his chastity cage to grope and fondle.  

Derek's cheeks burned with embarrassment, but he knew that this was what Vanessa wanted, and he was determined to fulfill her desires.

"I want you to listen to the sounds I make, the pleasure I experience," Vanessa said, her gaze intense. "And as you listen and watch, you will know that you will never be able to satisfy me like Anthony can. You will be humbled, emasculated, and utterly submissive."

"Yes, Mistress," Derek replied, his voice barely above a whisper and contorted by his ball-gag.

Vanessa smiled, knowing that Derek was fully submitting to her and embracing his role as her sissy cuckold.

"And just to remind you of your place," she said, reaching down to touch the chastity cage that confined Derek's penis, "your little clitty will remain locked up while Anthony and I enjoy each other." 

(Yes, "Chatty" actually generated that one and this entire exchange). 😈

Derek's breath caught in his throat at the reminder of his chastity. It was a constant reminder of his submission and his inability to please Vanessa sexually.

"But don't worry," Vanessa said, a mischievous glint in her eye, "I will make sure you get plenty of attention afterward. You'll be begging for Anthony's fat cock in your ass, won't you, my little sissy?"

Vanessa continues her relentless barrage of torment and humiliation, as Anthony fucks her just as relentlessly. 

After Anthony finishes inside Derek's wife, he is released from his bondage and invited to join in on the action. 

At Vanessa's gentle guidance, Derek felt a rush of both excitement and apprehension as Anthony's glistening cock was brought closer to his painted lips. The vivid contrast of his feminine appearance against the throbbing masculinity before him heightened his vulnerability and arousal.

"Go ahead, my sissy," Vanessa cooed, her voice a soothing melody. "Give it a kiss, just like you practiced with my strap-on earlier."

Derek's face blushed deeply, over Vanessa’s announcement that he practices with a training cock. 

With a deep breath, Derek parted his painted lips and tentatively placed a delicate kiss on the tip of Anthony's penis. It was a moment of surrender, a symbolic act that signified his acceptance of his submissive role and his willingness to experience pleasure in a way he had never known before.

"May I please clean you off, Sir?" Derek whispered in defeat. 

"You may, little girl." Anthony responded. 

"Thank you, Sir. And thank you for fucking my wife, Sir." 

These were the last words to escape Derek's painted lips, before he was silenced by a giant cock. 

"That's a gooooood guuuuurl!" Vanessa purred to her husband. 

To be continued. 

Mistress Andrea and "Chatty"

xoxo

Continued in: Husband gets Blacked