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

Emasculation

Continued from: He's so Screwed

When we left off, the girls had taken poor Jeremy's cock and mashed it into a chastity cage that was about the size of an Oreo cookie. And if that wasn't bad enough, they used a threaded dildo attachment to give their submissive some usefulness, all while fucking with his mind and his pre-conceived notions of masculinity. 

Jeremy got the divine honour of fucking Mistress Summer with this thing, rather than his actual penis. But Summer made it very clear that if he chose to fuck her, she would be returning the favour. 

Before this comeuppance was administered however, Cassandra wanted in on the action. The solution these two vixens chose was a dildo gag. A short intruding portion that looks and feels like a realistic penis, went into Jeremy's mouth to gag him, while a lifelike dildo triumphantly protruded from the other side.

This must be dreadfully humiliating for Jeremy. Paying to be in the presence of and serve two shockingly beautiful women, yet reduced to using stunt-cocks to fuck them.

Summer rode him slowly and deeply, making sure her asshole dabbed his nose while she bounced away. Cassie took a firm grip of his nipples like they were reins, and slammed her juicy pussy into his chastity dildo. 

His desperation by this point, must have been unbearable. I'm sure he was begging to be fucked, if it meant he was one step closer to release, to having his cock-cage removed. 

The girls ran a train on him and took turns destroying his asshole with their own stunt cocks!

If he spurted from his tiny device, like a sissygasm from anal only, his cage would not have been removed. After several rounds of ass-fucking from both of gorgeous Dommes, the chastity-gasm eluded poor Jeremy. 

Cassandra was of course pissed-off, she didn't want to remove his cock-cage. I'm surprised she didn't kick his balls again, out of frustration. Rather, they subjected Jeremy to one final torment and made him watch, as Summer and Cassie had sex on the couch. 

Jeremy eventually earned his release, after an hour or so of suffering at the hands of these two beauties. Maybe not the release he was hoping for, but after 10 weeks in chastity, he took what was offered. 

The girls made him stand in the corner and face the walls. They sat close-by to supervise and humiliate him. Jeremy was permitted to masturbate while facing the corner, orgasm into his own palm, then consume his entire load. 

He was then required to turn and thank the dominant duo for the load of cum he just consumed. About five minutes after this, limp and shriveled once again, they had him locked back into his day-to-day chastity cage. 

Was it worth it Jeremy? A 30-second wank into your palm in exchange for humiliation, pain, mental torture, degradation and having your arse raped by these two? I'm hearing that no safewords were used... 

I'm sure you wouldn't trade it for all the tea in China, Jeremy...

As usual, I'll be keeping your chastity key as you return to the vanilla world. When you're ready for more heavenly hash, feel free to book with me again. 

Mistress Andrea

xoxo

 

Continued in: 'Tis the Season

 

 
    

The Cute Couple

Continued from: When the Cat is Away...

I'm awe-struck once again. My face and neck are all hot and blotchy and I'm sitting here squishing my thighs together. Why, you ask? Because Goddess Vanessa is sitting directly across from me at my dining room table. 🔥

She came over for another brunch date, where we all gas-bag and whisper and giggle about our various exploits. This is the first time I have seen her since she had a handful of my hair, forcing my mouth onto her gorgeous pussy. 

Gawd, that was a hot playdate with her! Do you remember that one? I certainly won't forget. I want to crawl under this fuckin' table and go down on her right now. NO! I want her to snap her fingers and point to the floor and TELL me...to crawl on all-fours over to her and make her cum with my mouth.

I got up and went to the kitchen to snap me out of my daydreams, before I soaked through my friggen panties. Mimosas, and I whipped up a roasted beet, blood orange vinaigrette, early Fall salad. Root veggies to celebrate the Autumn Solstice, but still the bright flavour profile of warm September days. 

The girls both took a bite and moaned onto their forks. Success! Haha. 

There's no better compliment for a Chef or Cook, than to hear a woman moan in pleasure from the dish you've made her. The three of us are certainly no strangers to hearing each other moan. It immediately sexualized the conversation and Vanessa took center-stage, offering us another glimpse into her wildly unique relationship. 

You know how cute couples sometimes have cute little routines? Thursday is date-night. On Sunday's we go for a bike-ride or Friday is movie-night...

While sipping away at my mimosa, I heard ALL about Vanessa's cute routine that she enforces with her hubby, Derek. I listened on, once again in awe of this Goddess and totally aroused. It had been about a month since Vanessa told us that her hubby finally took a real cock and lost his sissy virginity. Apparently Anthony fucks him on a regular basis now. They are trying to get Derek to the point where he can cum from anal only and spurt a sissygasm from his cock-cage.

Now, in the latest development, Summer and I had the pleasure of listening to Vanessa's tales about her new routine. 

Like many suburban husbands, he gets home from work, pulls into the garage and shuts the overhead door. All seemingly vanilla yes? 

As you know from the previous stories about Vanessa, she keeps Derek's penis locked in a chastity cage. He wears the cage 24/7, under his work attire and while at home. What I didn't know until now, is that she also makes him wear panties and hosiery under his boy clothes. 

Apparently he is permitted full-size pantyhose or stay-up stockings. Nudes, navy and black are his approved colours. His panties are usually much more effeminate and frilly with softer shades of pinks, reds and pastels. She'd like to go with a bra too, but it would be too visible under his men's shirts, in the presence of his co-workers. 

This is where the ritual begins for poor Derek. Goddess Vanessa's does not permit Derek to be in male clothing in the home anymore! Like ever. Hehe...what a cute couple! He is literally not permitted to enter the home in the state of dress you see above. 

As he gets out of his car his eyes dart to the high heels that await him, and the perfectly placed giftbox containing a bra. With a face flushed by shame and humiliation, he begrudgingly undresses down to his panties and hosiery. He accesses and attaches the bra that Vanessa prepared for him, then the heels. 

Derek steps backward into a metal cage, hobbling on his heels and reaches his hand toward the clasp, to click a padlock shut. 

The "man of the house," who's penis is in a chastity device, is standing in a locked cage, in panties, a bra, stockings and heels, waiting for his wife to come retrieve him and permit him access to his own home.

Vanessa is a fuckin' Rockstar!

Derek was mindful to neatly fold his silly boy clothes into the basket provided and place his male footwear beside. When Vanessa eventually comes out to get him, she'll unlock his cage and invite him into the home. 

Access to the garage is locked by Vanessa, along with access to his male clothing that remain cast-away and discarded on the floor. 

He moves as quickly as he can in the heels, as Vanessa hastily follows behind, smacking at his ass if he is not moving fast enough. His high heels carry him all the way upstairs to his sissy bedroom. Derek no longer shares his marital bed or matrimonial room with his wife. He is down the hall in a spare room that is adorned with soft pink hues, make-up, perfume and feminine wigs.

He is met with the sight of an elaborate sissy outfit that has been laid-out for him by Vanessa, with all the accents and accessories. And apparently, with few exceptions, this exact ritual happens EVERY day!

Sometimes Derek finds a maid outfit waiting for him, other times it's a schoolgirl uniform but those two options are typically reserved for the weekends. During the week, his clothing at home is that of an exaggerated, elaborate little girl. Hemlines are short and voluminous, bows are satin and sleeves are full and puffy. 

Derek sits at his vanity mirror and does his own make-up now. He'll do his nails too, if they need it and he selects and styles a wig if one has bee laid out for him. Then he will dress in the outfit provided and click downstairs to find his wife. Here he will make the big reveal and perform a curtsy to her. 

"So...are you two even intimate anymore?" Summer asked innocently. "Like do you have sex together, without Anthony?" 

"Oh, of course." Vanessa replied. "Sex for Derek is just a little different now." 

I giggled out loud. 

"Oh yes, yes. I've had them do this before. So emasculating, I love it." I said, as I referenced some previous encounters with chastity boys. 

Apparently Vanessa loves it too. 

Who wouldn't!? You can fuck as long or a short as you want with exactly the size dick you want and fuck it as hard or a gentle as you'd like, without some silly boy finishing into you in 37 seconds.

If I was male, Goddess Vanessa would have me cumming into her in 19 seconds flat! She's actually doing Derek a favour, it's the humane thing to do. She's just too damn hot and sexy. 

"Do you do the mouth one too?" I asked Vanessa. 

She answered excitedly. "Oh yes, totally. I love it when his nose dabs my asshole." 

I began to explain to Summer that "the mouth one" meant a dildo that is wo...

"Oui Mistress, I know. You made me wear one and do that on YOU once." Summer interrupted me. 

I blushed. Remembering back to a time in the old house, when I had Summer in the dungeon space and in a dildo gag. I steering the conversation back to Vanessa.

"And he's pussy-free still...asshole and feet only?" I asked of Vanessa.

"Yup." She replied confidently. "He can taste my pussy, but only this way..."

Vanessa pulled out her phone and showed us a picture of Derek she took recently.  

What a Goddess!

Well if all this doesn't get you in the mood for Locktober, I don't know what will. 

Speaking of which. I need to book an appointment with Russell. We had a deal and it's almost time for him to pay the piper! 

Mistress Andrea 

xoxo

 

Continued in: She-Devil