Dream Team

Continued from: The Tears of the Sissies will Water the Meadows of France

The day had arrived for Remy, the sissy boy from France, to join the girls and I for his fantasy session. I would be playing the role of the strict Schoolmarm. 

(Not sure what I'm doing with my hands in this one)

I arranged for one of my older, male, slightly creepy clients to play the role of the leering Principal in this all-girls school. Then, as I stated in the previous post, I put together my dream team of fellow students. Beautiful women who would like nothing more than to tease, humiliate and belittle poor Remy, as the new foreign exchange student. 

Check out my dream team: 

We have Summer.

The bubbly best friend who's skirt is not regulation length, just to drive the boys mental. 

Nancy. 

The more mature, senior schoolgirl who is the leader of this group and close assistant to the teacher. "Assistant" could be synonymous with tattle-tale. 

Finally, the new girl, Carley. 

The goth-girl, maybe the wild-child, believed to be unpredictable. This will be her first playdate at my Facility so I'm not sure what this little pixie is gonna do. She does look great in her uniform though. I can't wait to see what this little sniper is capable of.  

There was absolutely no fuckin' around when this French wiener arrived. I booked him in personally, dressed in my role and wielding a cane. He was booked in through the cellblock area so he could truly appreciate his impending peril. Every stich of his clothing was removed, right down to the little pink, clit cage that he wore to his session. 

This was my view as I towered over him. He was completely hairless below the eyebrows, he lacked muscle tone for a man, and his pathetic little thingy looked like so: 

Ick! We need to get that little clit hidden beneath some panties, forthwith! I seized control of the keys to his little clit cage and locked them away with his boring, boy clothes. 

When Remy originally booked this multi-day session, he wanted to be dressed like the other girls. But just to make things worse for him, I didn't do a full transformation with makeup or a wig. I wanted him to still look male, just to humiliate him further, in the presence of my beautiful girls. 

Appearing outwardly male for day one was my rule, but dressed like a schoolgirl. He will have to show me that he truly wants to be a girl. He will need to behave like one, sit like one and learn how to please men like one, before I'll continue his transformation beyond his mere attire alone. 

Which outfit should we go with? I had three options that fit him. 

Option A:

(Not a huge fan of the shorts, but you can see his locked up little clit-bulge in the front)

Option B:

(It's important that he be in high heels, as he clicks around the classroom)

Option C:

(Look how ridiculous he is, dressed like that!)

Once I get him dressed, he will feel sick to his stomach with humiliation. Then I'll finally present him before the girls and tell him to introduce himself as Lena, his sissy name. 

Poor Lena is going to be in for a long few days! She's already crying and I haven't even caned her yet. 

Stay tuned. 

Mistress Andrea 

xoxo

Continued in: Les Misérables

 

A Mouth Punishment?

Continued from: My Pet

A Sarah Jane story

Hi, everyone, it's Sarah. 

Daddy is away on a work conference thingy and I got myself into trouble in his absence. That didn't take long. Sheesh! He's only be gone for two days.

He's left me like this before, for similar reasons and usually he locks me up in a very secure chastity belt. There would be an emergency key left behind for me but it would be in a lockbox that only he has the code to. I haven't had to use this option before, but the process would involve me having to message or call Daddy, explain the emergency in which I need to be unlocked, then he would give me the code.  

But...like I said. I have never had to use this lifeline. I just suffer through the throbbing sensation of being locked up and denied. I have to piss through the metal screening, poop through the anal opening provided and take extra care in cleaning and hygiene. If I leave the house, I have to adjust my wardrobe accordingly, so the belt is hidden. 

It's humiliating, frustratingly arousing and embarrassing to be locked up. The perfect cocktail of emotions for a naughty slut like me. 

However! Daddy didn't lock me up in his absence this time. Nor did he get me his favourite babysitter (Mistress Andrea). He said he wanted to distance-play with me while he was away. 

Awww! My heart! 💕 My Daddy!

So play we did!

Yesterday I had to log in and work from home, including some zoom calls with my colleagues. Daddy told me to dress in my schoolgirl attire. My age-regressed lower half hidden from my colleagues, my upper half professional. I even wore a school-tie which looked professional to my team and not weird. But my face burned red with humiliation, as I knew the tie was just an accessory to a very short plaid skirt, ruffled ankle socks and Mary Janes that I was hiding below. 

Daddy let me wear full pantyhose too, because it's been freakin' cold lately. So I just slipped my ruffle socks over my hosed feet. The whole ensemble had me feeling very adorable, yet I knew the reason Daddy dressed me this way, is that I was due for a maintenance spanking, between zoom calls. 

*Gulp*

Daddy had me lay these out in preparation. I knew I would be receiving all three. 

Imagine readers, how this feels for an adult woman. Sitting behind a computer working and engaging in meetings while dressed like a schoolgirl, knowing that at some point during the day, you're going to be spanked. I was nervous with butterflies, I was humiliated and my crotch was wet. So shameful! 

When the time came I put myself in timeout, nose to the corner and hands on my head. I set up my phone and took a timer-photo to send to Daddy. 

"I'm ready for my spanking Daddy."  I sent, along with this photo: 

Daddy simply responded with a: 

"35 lashes with the belt please, over your pantyhose and panties, then 25 on each cheek with the hairbrush, then 25 on each cheek with the bathbrush." 

Yes...I spank myself when Daddy orders it. It can never compare to the real thing, being over his knee. But it helps to scratch my itch. 

My knickers and hose provided decent layers of protection from the belt, but the dense wood of the brushes burnt right though my protective layers. 

Next came the same allotment of strokes, only this time, hose down and over my panties.

Now I was starting to sting and redden-up. I already knew what was coming next, Daddy sent the message anyway...

"35 with the belt, and 25 per cheek with each brush, on the BARE!" My last layer of protection was stripped away. I did an ok job on myself. Again, it can never compare to the real thing, yet my cunt couldn't tell the difference. She was soaked! *blush*

I sent Daddy this one, seeking his approval that I had done a good enough job on myself. I was praised and rewarded with the opportunity to masturbate for him. I am never, ever allowed to have a vanilla orgasm. That being said, his next instructions were to neatly lay out my ring-gag, lubricant for my asshole and a butt plug of my choosing. 

I obeyed right away and sent Daddy this. I was eager to have a cummy for him! 

Unfortunately I had some work matters to attend to first, so my masturbation was delayed a bit. When I wiggled free of a zoom call meeting, I rushed into Daddy's room and plugged my asshole as he requested. 

I set up my phone to film. I didn't have to include my face in the video, Daddy only wanted to hear me cum, so the filming was more to capture the audio. In no time flat I was screaming out, "I'm cumming Dadddddddyyyyyyy!"

It was a wonderfully powerful orgasm. My hungry little asshole clenched that plug so tightly when I began to spasm. I was loud too! Like porn-star loud! 

I love being Daddy's little porn-star. 💗🌟

Proudly, I sent my video to Daddy right away. He was driving. Then he tells me he's going to listen to it through his car audio. 

Gawd, I was so embarrassed! 

A few moments later though, my stomach sunk! This was our text exchange leading up to and after he listened to my clip.  

FUCK! Fuck fuck...

Look at my image above, masturbating on the bed. Do you see a gag in my mouth as I was instructed to do?! I laid one out and even photographed it for Christ sakes.  

Fuck! I completely forget and now I'm in deep shit. I have no excuse and I must accept my punishment, likely when Daddy gets home. 

You remember the rules in our house? Punishments fit the offence. If I am caught with a run in my hosiery, the soles of my feet get whipped. Caught masturbating without permission, my bare cunt gets whipped...you get the idea. 

What's a mouth punishment?? 

Likely a mouth soaping. Which really fuckin' sucks! Especially in Daddy's house and let me tell you why. Check this out: 

This is SOAP!! This is a fucking bar of soap, in our bathroom. It remains proudly displayed on the sink, as a reminder to me. This is the sink where I brush my teeth each morning and night, where I am forced to look at this stupid soap-dick that has been in my mouth many times before. 

Bratty, back-sass, too much swearing...and coming soon...forgetting to gag my mouth when Daddy asks. 

He's already declared that I'm going to be punished when he gets home. I am only surmising that it'll be the soap dick, since the violation relates to my mouth. I just hope it isn't. 

The last time I got a mouth soaping I was marched to the bathroom fully naked, wearing only heels that I was wobbling in. I had to bend fully at the waist and use my own saliva to get a lather on the soap dick. Daddy paddled my bare bum to encourage me to give it head and to deepthroat the phallically veiny soap. It was a dreadful and effective punishment. 

After I saw the message from Daddy on this occasion, that I was going to be punished, my tummy was sick with butterflies. I assumed it would be the heavy wooden paddle and the soap dick for sure!

I wasn't wrong, but much to my surprise I had a choice. A predicament. Daddy loves giving me predicaments. So I am forced to choose my own punishment and choose between the lesser of two evils. Then stew over my choice until Daddy gets home. 

As expected, he offered me "mouth soaping". As I explained above, this means paddled on the bare bum until I break and begin to suck the soap dildo frantically, to bring an end to the paddling. 

But then...Butt then, pun intended...a second option from Daddy. 

Would I prefer to perform ass-to-mouth with another girl, using a dildo...

Like...she fucks me with a strap-on then I kneel and suck her? Or she uses a dildo into her asshole then fucks my mouth with it?? Or even worse!! Daddy fucks her in the ass then mashes his cock into my mouth??!!

I don't know what to choose...but I have to choose! Please help...

Sarah Jane

xoxo

Continued in: ATM

 

 

 

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

  

Jail Bird

Continued from: Busted!

Once the officers escorted Russell into my kitchen, still in handcuffs and pant-less, I surveyed the state of his bare ass. They told me all about the traffic stop, the reckless speeding and how Russell elected "administrative discipline" as an alternative to jail. 

They also told me that immediately before his spanking and humiliation, he was...ummm...recklessly aroused. 

"Oh he WAS, was he?" I angrily glared in Russell's direction. 

"He's going to be put in jail, Officers, I assure you! And I'm sorry he drove dangerously." I said to the two policewomen. 

"Jail, Ma'am?" Officer Summers asked curiously. 

"Yes Officer, my jail has metal bars too...and I assure you it is quite inescapable." 

I held out my hand to reveal the gleaming stainless bars of a chastity cage. 

"Can you restrain him for me please, Officers? This should help with that nasty erection issue you told me about.”

The girls held both of his arms securely, as I pulled Russell's balls through the base-ring and slid the tubular metal over his flaccid cock.  

"Look!" Officer Cassidy said cheerfully, "it’s a jail bird!” 

"Corner! Young man!" I barked at him.

"Oh...?!" Officer Summers replied, sounding curiously shocked. 

I started the coffee maker and invited the two of them to remove their hats and sit. 

"Yes, Officer Summers, we practice certain forms of discipline in this home, that appear to be in alignment with the roadside justice you two administered." I explained to them. 

"Cornertime and spankings are lengthy and frequent under this roof, Officers." I continued. 

"About the roadside justice, Ma'am. We thoug..." Cassidy tried to justify their actions but I interrupted her before she had a chance to continue. 

"Is spanking and belt-whipping speeders a common practice in policing, Officers? I’m sure it would likely help, all of society, but it sounds super off-the-books.”

"Ummm, no Ma'am...but he agreed and we were just having fun." Summers sheepishly said. 

"Fun? I think it's called abuse of process actually, discreditable conduct and breach of trust." I hissed at the two brazen officers. 

They were both looking fairly scolded and ashamed at this point, with Russell listening to all of this play out, from his own position of shame and humiliation in the corner. I decided to go for it. 

"You! Blondie...sit right there." I pointed to the loveseat and directed Summer to sit. 

"Officer Cassidy, get across my lap young lady." I ordered, as I dragged her by the wrist toward the couch and tipped her over my knee. 

Her position forced her little poly-cotton, police pants to pull tightly across her juicy butt. It looked like a beautiful target, despite that fact that her belt-worn kit was digging into my thigh. Officer Summers watched from the other sofa, as I spanked her cute partner over my knee. 

"Officer Summers, you're next. Get over here." I snipped to my cosplaying wife. 

Summer's arse looked equally as gorgeous in the police pants. Way too much protection from a spanking but what a visually appealing target! Yum!

I let Russell listen from his corner, as the dull smacks and little whimpers continued. Eventually I had him turn and face us. 

"These two apparently like having a little 'fun', young man. Would you show them to our bedroom and help them out of their uniforms for me?" I purred to all three of them. The girls smiled, while Russell had a look of desperate arousal on his face. 

When I joined the three of them in the bedroom, I was met with this scene: 

"I see you put your handcuffs to good use, Officers?" 

My two little cops giggled and slid closer to one another on the couch. 

"How long have you two been with the Force?" I asked them. 

"Only three years, Ma'am." Officer Summers responded. Officer Cassidy nodded in concurrence. 

"Still rookies then? Rookies who would be fired if anyone found out about your roadside justice I would imagine?" I asked.

They didn't respond. This was all for Russell's torment anyway, as he listened helplessly from the bed, his cock twitching within the metal bars of his cell. 

"It must get lonely out there at night, just the two of you, for 12-hours in a cruiser.? Do you two ever...you know?" I probed into their partnership at work and whether or not they've ever explored.

Cassandra picked-up on what I was doing right away and answered in character. 

"Ohhh, no. No Ma'am. We both have boyfriends." Officer Cassidy replied. 

"I see." I responded, raising an eyebrow in the process. 

"Well, if you don't want me going to the media about your discreditable conduct, kiss her. Kiss your partner on the lips for me." I threatened. 

I heard Russell groan in desperation from the bed. The girls smiled and scooched closer to one another. They knew what I was up to now, torturing Russell with a little forced-lezzie masquerade. 

"See girls. It's not so bad is it?" I purred to them. 

I had Officer Cassidy stand and remove her panties, which I turned inside out to expose the damp, inner gusset. It seems she gave herself a good saturating during her light spanking. 

I walked over to Russell and mashed the panties into his mouth to gag him, gusset first, before returning to the girls. 

"Alright Blondie, you get back there and you lick her butt!" 

When Russell heard me give this order, he groaned into the delicate lace of Cassie's panties. His groans were now competing with Officer Cassidy's groans, as her diligent partner was really going to town with her tongue.

After watching the two PW's (police-women) explore each other's bums, I decided to join the action. Russell was able to watch and listen to both of them take turns going down on me. 

"Fuck my wife will you? How's that locked up cock of yours, silly man?" I thought to myself, as I trembled and came onto Summer's pouty lips. 

This was the REAL punishment for Russell, for banging my wife. This was my sweet, vindictive revenge!

After several rounds of crippling orgasms for all of us, the girls logged-off with dispatch for the night and skipped off to shower together. 

I crawled onto the bed like a Lynx, twirling Russell's sensitive nipples and rubbing my soaked pussy against his cock-cage. 

"Remember when you used to fuck me like this?" I said, while launching his legs onto my shoulders. "Remember how you use to tie me to the bed the same way? You were a great teacher, Russ, but look at you now!?”

"Do you remember how you used to gag me and put plugs in my ass, then let me ride your tongue?" I continued to tease. Russell just smiled and whimpered, his cock was trying to burst from the metal cage. 

"I'll unlock you right now and you can take me. You can take me like you used to, Sir. Gagged, bound, whipped and fucked. I'm all yours, Master..." I purred to him. 

I leaned in and put my hand over his mouth so he couldn't respond right away. 

"Provided," I hissed into his ear, "you celebrate Locktober this year."

Hehe! Aren't I a little she-devil or what? 

Poor Russ! 

What an awful, wonderful decision to have to make!

Mistress Andrea

xoxo

Continued in: Old Flame