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

  

"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

 

 

Call me "Sir"

Continued from: Sissy husband Fluffs

Vanessa wasted no time in springing from the bed to access her nightside drawer, housing her strap-on. The sensation of her husband's tongue lapping Anthony's cum from off her bare asshole had her ravenous with sexual aggression. Earlier, she clearly stated she wanted to fuck, it was becoming abundantly clear to Derek that she wasn't done yet!

Anthony, sensing that his role in the evening was nearing its expiration, chuckled awkwardly, suggesting he should leave the two love-birds alone. 

"Anthony baby, I think there's a pair of my husband's old trackies in the top drawer. He doesn't need male clothes anymore, help yourself." 

Derek curls up in a little victim-pose on the bed, his mind races with conflicting thoughts and emotions as he contemplates his heterosexuality in light of the events that just occurred. Orally pleasing a man challenged his deeply ingrained sexual orientation and stirs a potent mix of confusion, humiliation, and curiosity within him.

Feelings of shame and vulnerability wash over Derek as he confronts his own internal conflicts. He questions his identity, grappling with the complex interplay between his innate desires and the expectations placed upon him within the context of his FLR with Vanessa.

"Go downstairs and watch Cocaine Bear, baby, I'll be down soon," Vanessa remarks, kissing Anthony on the cheek as her dildo pokes him in the leg. 

Vanessa's apex-predator instincts re-focus to the prey before her, still curled into a fetal position. 

"Take off your dress and panties sissy." 

As he reflects, Derek recognizes that his submission to Vanessa extends beyond traditional notions of sexual orientation. It transcends societal norms and delves into the intricate realms of power dynamics and surrender. He acknowledges that his obedience to Vanessa’s directives is an expression of his devotion and the trust he places in her as his dominant partner.

In the midst of his introspection, Derek acknowledges the potency of the humiliation he experiences. It is a profound element of their dynamic, testing the limits of his submission and pushing him to confront his deepest fears and vulnerabilities.

As Derek’s legs remain suspended in the air, exposing his vulnerability and submission, his gaze is drawn downwards, forced to confront the image of his delicate knee socks and dainty Mary Jane heels. The juxtaposition of his feminine attire with the act of being penetrated like a girl amplifies the psychological and emotional impact of their play.

With each thrust, Derek’s attention is split between the sensations within his body and the visual reminder of his femininity. The sight of his own legs adorned in knee socks and the dainty heels reinforces his role as a submissive, evoking a profound sense of surrender and further blurring the lines of his once heterosexuality.

Vanessa’s dominant presence looms above him, her gaze fixated on his vulnerable state. She revels in the visual tableau before her, the contrast between Derek’s sissy attire and his experience of being penetrated like a girl igniting a powerful mix of dominance and desire.

For Derek, this moment is both transformative and challenging. The combination of physical sensations, visual stimuli, and his submissive role deepens his surrender, confronting him with the complexity of his desires and the fluidity of his identity.

Vanessa doesn't let up, not with her girl-cock and not with her relentless tormenting of her sissy. 

"Do you wish this was a real cock young lady? Tell me you want a real cock, sissy. Do you wish I was Anthony right now?" Vanessa purred, not letting up. 

Vanessa’s questions hang amidst the moans in the room, eliciting a mix of vulnerability and desire within Derek. The implication of her words penetrates his thoughts, stirring a whirlwind of conflicting emotions.

In a voice laden with submission, Derek responds, his words carrying the weight of his humiliating admission. “Yes, Ma'am,” he whispers, his voice quivering with a mix of longing and surrender. “I wish it was a real cock that was fucking me.”

"Call me 'Sir'", Vanessa snaps, slapping his smooth ass and grabbing his hair. 

"Please Sir, please fuck my pussy. I want your real cock Sir!" Derek gasps out. 

The confession unveils a deeper layer of Derek’s emasculation, exposing his longing for a more authentic experience. It reflects the complexity of his submission and his willingness to embrace both the physical and psychological aspects of his role.

Vanessa’s gaze narrows, her expression a mix of understanding and dominance. She absorbs Derek’s response, acknowledging the depths of his vulnerability and the significance of his longing.

“Your desires are noted, sissy,” she affirms, her voice resonating with authority. “Rest assured, I will continue to guide you through an exploration of pleasure and surrender. The next time you need to be fucked or spanked, Anthony will be doing both!" 

"Yes Sir," Derek cried out between grunts and moans. 

When Vanessa felt her husband had suffered enough, she pulled her strap-on out of his spent asshole and returned his panties to him. 

"Put those back on honey, make sure your cage is showing," Vanessa commanded, before they both attend downstairs.  

Once downstairs, Cocaine Bear was put on pause, while Vanessa again led the conversation about their future dynamics. 

"Anthony huni, my husband and I had a little chat upstairs," she started to explain. 

"That didn't sound like much of chat," he replied with a smirk. Derek's face burned with embarrassment. 

"We decided that in future, if Derek is not meeting your "needs", you have my permission to spank him," Vanessa added, her voice now smoky and devious. 

Vanessa’s suggestion silences the room, introducing a new element of discipline and control to their dynamic. Derek’s heart skips a beat, knowing that the consequences of his actions could now involve not only the disciplinary strict measures from Vanessa but also the firm hand of Anthony.

Anthony takes a moment to consider Vanessa’s proposal, his gaze shifting between her and Derek. He understands the significance of this suggestion, the power it gives him to assert dominance and reinforce Derek’s submission. After a brief pause, he responds with a tone of authority, his voice carrying weight and intent.

“I accept your proposition, Vanessa,” Anthony states, his voice firm. “If your husband fails to meet my expectations or disrespects the boundaries of our dynamic, I will administer the discipline he requires.”

Derek’s heart sinks at Anthony’s words, fully comprehending the gravity of the situation. He knows that his behavior and obedience will now be scrutinized more closely, his actions directly impacting the consequences he may face under Anthony’s hand and probably his belt. 

Vanessa’s eyes gleam with a mix of excitement and anticipation, her dominance asserting itself in this new facet of their dynamic. She nods in agreement with Anthony’s response, acknowledging the power and responsibility he now holds in their relationship.

All had been settled, for the next chapter of sickening humiliation and vulnerability for poor sissy Derek. Throughout this entire ordeal, the keys to his chastity cage never made an appearance. 

They likely never will. 

Mistress Andrea and "Chatty" 

xoxo

Continued in: The Secretary

More of Vanessa, Anthony and Derek is also continued in: "Thank you for Fucking my Wife"