First Time

Continued from: Mistress Andrea's Gift

[F/ff] [forced bi] [CNC] [slaves] [lezdom]

I just had the girls down in the basement sex dungeon for the past few hours, while Russell was at work. (Sorry, Russell! Not sorry...hehe)

And by "the girls", I'm not just referring to Summer and Sarah Jane. We were pleased to welcome our beloved Mandy into the dynamic too! She had requested a session about a week ago and I was finally able to get her some private time with us, not quite expecting that Summer and Sarah would be joining in too. *giggle. 

Omg, there was so much vagina! 

Despite the shrieks of pain and the echoing pleas of "noooo, please don't make us do that, Ma'am," I think the girls had a blast of a session. You see, they all commiserated beforehand and asked for CNC (consensual non-consent) play. The type of play where they fantasize that all the sexual acts are against their will, that they need to be whipped and tortured to perform them, and that they are captive slaves in this sadistic dungeon. 

We had such a good time in fact, that I asked Sarah Jane if she wanted to post about how it all went down. Much to my surprise she said no, but very quickly offered to write about her very first time with Mandy, the first time she was "forced" to perform sexual acts on another woman. Ok...this sounds like fun too. 

Before I give her the floor here, a few housekeeping matters from the last post that needed to be addressed. If you remember, I sent sissy alice to a professional disciplinarian to experience his very first spanking over the knee of a wonderful woman. Also, it was his first time dressing not as a "he", but as a "she", in front of someone else, as I sent alice to her session dressed like a little girl. 

Then, to amplify his humiliation even more, I made sissy alice write a full blog post about the intimate and vulnerable details of his spanking. During that post, he made this comment: 

It struck me that I was not just there for myself, but I was representing Mistress Andrea. I wanted to do her proud in front of Lady Jose and make this an experience of a lifetime. 

Yes, you were representing ME! 

Later on in that post he then said this: 

Positioning myself, head down and straddling her lap, Lady Jose started playing my red bum like a drum, with the spatula and bath brush, and I was so humiliated I hate to say I started giggling. I couldn’t help it! Those sorts of situations sometimes make me laugh uncontrollably, it’s the nerves. Lady Jose didn’t like that, slapping harder I was told, “this is not supposed to be funny alice, this is supposed to be humiliating!”  

To which I commented on that post: 

Ummm...ya. Once again, probably not a good idea, alice. You and I are going to have a little "chat" about this part!!!

So...alice and I had our "chat". 

"I'm sorry for giggling during my spanking, Lady Jose," is what's written on those pages. 

100 lines, followed by 30 minutes in timeout, in the corner.

While alice was in the corner, I sent all pages of the lines and the timeout photograph to Lady Jose, then I myself, apologized to her, on behalf of this silly sissy... 

A pleasant and graceful response from her: "Alice did well by writing the lines, I trust her not doing it again."

...and alice will be booking a follow-up session with Lady Jose, to once again be spanked in the coming months. Spoiler alert, alice, you will be introduced to the cane during this next session.

Just a little housekeeping, that's all. Take it away Sarah Jane. 

**************************

My First Time 

Preface

It is probably rather cruel to write a story like this for Daddy, when I know Mistress Andrea has his penis locked in a chastity cage. I know I'll probably be spanked for writing this in such lewd and erotic detail, I'll probably get a whuppin' with Daddy's belt...but...we're gonna do this anyway. Please enjoy, everyone. (sawry, Daddy 👅) 

A Sarah Jane Story  

What a night it was, Daddy! Mistress Andrea decided to treat us to a fancy dinner, just the three of us, at an exclusive restaurant in town. She dressed us up like dolls, putting Mandy in a ravishing red cocktail dress that showcased her curves perfectly, and me in a sleek black number that accentuated my bum and tits. 

But of course, our elegance wasn't complete without a subtle touch of humiliation - Mistress insisted we wear our collars in public, a discreet yet unmistakable symbol of our submission to her. 

As we sipped champagne and savoured each bite of our exquisite meal, I couldn't help but feel a thrill of excitement mixed with nervousness, Mandy and I exchanged demure glances, both of us aware that this refined evening was merely a precursor to the debauchery that awaited us back at the Facility. 

Throughout dinner, I stole peeks at Mandy's cleavage, her lips, her pretty features, my mind wandering to the possibilities of what might unfold later with this suburban soccer mom. Would Mistress command us to kiss? To touch? The uncertainty was delicious, heightening my arousal as I nibbled on my food. 

I'm not into girls...but I found myself growing increasingly...damp. My delicate black panties, adorned with tiny lace and satin bows, were no match for my naughty thoughts. I couldn't help but imagine Mandy's reactions if Mistress forced me to pleasure her - the soft gasps, the fluttering eyelashes, the gentle trembles...

My fantasy was interrupted by Mistress's piercing gaze, her eyes locking onto mine with unnerving intensity. She knew, Daddy. She always knows when I'm getting too carried away. 

"Give me your panties, right here, right now!" She hissed, with a subtle crook of her finger as she motioned my hand beneath the tablecloth. My heart skipped a beat as I hesitated, my fingers trembling slightly as I reached for the hem of my dress. Slowly, I arched my bum off my seat and extracted my soaked panties, trying to conceal them from prying eyes. 

But Mistress would have none of that. "Show us, Sarah Jane," she purred, her voice low and commanding. 

With a flush rising to my cheeks, I reluctantly held open my panties, the gusset gleaming with my arousal. Mandy's eyes widened in surprise, a hint of fascination dancing across her features. I felt like a naughty little girl caught with her hand in the cookie jar. 

"I-I'm so sorry, Mistress," I stammered, my apology tumbling out in a rush. "I don't want to do this!" I squirmed uncomfortably in my seat, my face aflame with embarrassment as Mistress's eyebrow arched higher, unaffected by my mock resistance. 

"And what about you, slut? Shall we look at your panties too?" Mistress snapped her head towards Mandy, who inhaled and clutched a fist of tablecloth into her palm.

"No, please Ma'am, not here," she protested, no doubt feeling the saturation of her own panties and dreading the prospect of having to reveal such shameful arousal. 

Mistress Andrea's words dripped with seduction and menace, as she explained how the rest of the night would go down. My insides twisted with excitement and fear, as her threats of whipping and beating us into submission, hung in the air like a tantalizing mist. I shot Mandy a sly glance, noticing the faint blush rising to her cheeks, as Mistress Andrea outlined our impending "persuasion." 

When the three of us got back to the mansion, The Facility as it's known, it was deathly quiet. I half expected to be taken to the basement sex dungeon in shackles, but the minute we got in the door, Mistress ordered us to strip fully naked, leaving only our collars and high heels in place.

With practiced ease, Mistress Andrea blindfolded Mandy and I, heightening our senses and raising goosebumps across our skin. We were sat side-by-side, shoulder-to-should, as Mistress guided our shoulders back, bare breasts thrust forward and hands resting in our laps in a sharp, alert posture.   

I could hear each of her heel clicks across the floor as she bustled about the room, setting things up for our session. I heard her start a fire, followed by the powerful scent of wood smoke reaching my nostrils. Unconsciously, I found myself leaning slightly to my left, my bare arm pressing into Mandy's, as if to seek some safety from her warm skin.  

It was a short-lived moment of comfort however, for Mandy was snatched away by Mistress, taken from her seated position and led away stumbling. I could only hear her staggered high heel clicks and Mistress's firm command, "get over here!" 

My chest fluttered in surprise, as I felt a leash being attached to my collar and pulled in an upward direction, ushering me to my feet. With a gentle tug forward and still unable to see, I teetered on my high heels, taking shallow, shaky steps forward. 

I was temporarily blinded by the light of the room, when Mistress finally removed my blindfold, and I found myself standing at the edge of a bed. My gaze refocused, and I caught the sight of Mandy, fully naked save for her heels and collar, positioned in a downward dog pose on the bed. Her plump bottom was thrust upward into the air, her flawless asshole was poised and presented like an offering. 

I was so confused, I didn't want this. I had a safeword to use but didn't use it...why was the sight of her pussy and bottom hole making my mouth water?! What was happening to me? 

I tried to protest, Daddy, really I did! But Mistress Andrea wasn't having it. 

"I'm not a lesbian, Ma'am." I exclaimed, attempting to sound convincing. But my words fell flat, and Mistress simply raised an eyebrow. Before I knew it, her whip cracked against my bare bum, the sting making me yelp in surprise. 

Spaghetti is straight too, until it gets wet! *giggle

"You'll do as you're told, little one," she said sternly. "Now, get up on the bed behind Mandy." 

I hesitated for a moment, my face burning with shame. But another lash of the whip convinced me to scramble onto the bed, my heart racing with anxiety. As I settled into position behind Mandy, my face inches from her asshole, I couldn't help but feel a mix of emotions. Embarrassment, arousal, and a dash of fear all swirled together in a toxically exhilarating cocktail. 

I waited with bated breath, as Mandy looked back at me, almost reassuringly but just as embarrassed as I was. What would Mistress have me do next? Would I be able to obey, or would my humiliation prove too much to bear and safeword out of the scene. 

I remember the exact moment when Mistress whipped me once more and issued her next command. 

"Kiss her hello, Sarah Jane," she said, her voice low and husky. "Tell her how pretty she is." 

My heart sank as I realized what she meant. I was to greet Mandy's bare asshole as if it were her lips, French-kissing it with all the passion and intimacy I would reserve for a romantic partner...a lover. The thought alone made my stomach turn with humiliation, but I knew better than to disobey. 

Taking a deep breath, I leaned forward, my lips puckering up to meet Mandy's waiting bum hole. I closed my eyes, trying to block out the indignity of the situation, and planted a sloppy kiss on her tender pucker. As my tongue darted out to explore her hole, I forced myself to utter words of adoration, trying to sound sincere despite my mortification. 

"Hello, Mandy," I murmured, my words muffled against her ass. "You're so beautiful, Mandy." 

Ugh, the phrase made my innards roil with embarrassment.

As I continued to make out with Mandy's asshole, I felt my face flaming with shame. This was a whole new level of debasement, Daddy, one that left me squirming with discomfort. And yet, beneath the surface of my humiliation, I detected a spark of excitement, a twisted sense of thrill that came from pushing my boundaries and exploring the depths of my submission. 

Daddy...sigh...I was hooked! 

Shall I continue the story, Daddy? 

Sarah Jane 💟

Continued in: Mind Games

 

 
  

Mistress Andrea's Gift

Continued from: Spanked by Lady Jose

[M/f] [spanking] [OTK] [strapping] [sissy] [feminization]

I am pleased to report that not only did Lady Jose permit me to post about her services and the session she had with sissy alice, but she also said she liked it! And, a little icing on the cake, she liked my content enough to share it on her social medias and with Miss Sarah Gregory!! I'm freaking out right now. Star-struck!

Let's see if, in equal measure, Lady Jose likes alice's version of events.

The following, was written and illustrated by sissy alice. It is titled: 

Mistress Andrea's Gift

I woke up with a start, wide awake, nervously grabbing my phone and checking the time, it was only 05:46.  I am always paranoid about oversleeping on days when big things happen and boy was today a big day!  Today I was going to be spanked for real.

I had been looking forward to this day for a while now, the first appointment was delayed due to sickness which only added to the anticipation, but finally it was here. 

Not only was this going to be my very first IRL spanking, but it was really the first time I had been face to face with someone in real life not pretending to be a boy but being my real self, as alice. Add onto that my appointment was with a renowned international disciplinarian as well and you can understand my excitement and nerves!

It started a couple of months before, Mistress had been keen to have me experience a real life spanking and had found Lady Jose after a little research. The first thing I knew about it was an email from Mistress getting me to fill in an application form, which was really exciting! Thankful to Mistress who helped me fill it in, and before long I had emailed Lady Jose with my application, nervously hoping I would be accepted.

Before long Lady Jose came back and accepted, and the date was set. My outfit for the spanking was outlined and approved by Mistress. I was to be dressed like a “little girl” for my spanking. The outfit had been prepared and hanging in my discipline corner for the past few days, ready for the session, a constant reminder of the humiliation I was about to endure.   

Mistress had been teasing me about the approaching day, making sure it was always on my mind. Mind you, I think I would have been thinking about it without the teasing but it added to the mix of emotions swirling inside me, feeding the giant butterflies in my tummy.

Some of the last advice from Mistress the night before was to “remember my manners, stand feet together, eyes downcast. Remember to curtsy if required and address Lady Jose with the respect she deserves." I was to be a demure and dainty young lady. 

It struck me that I was not just there for myself, but I was representing Mistress Andrea. I wanted to do her proud in front of Lady Jose and make this an experience of a lifetime.

I made sure to shower well, shave everywhere I needed to (legs, clitty, armpits, chest, face). I had made sure to save my hygiene cleaning for this morning so that my locked clitty was as clean and presentable as it could have been.

For discretion it was agreed I would arrive at Lady Jose’s studio in “boy mode”, but that was not a problem, I could wear a boy's tracksuit bottom and top over my real clothes. I set about putting on my nails, and making sure to apply a touch of make up (mascara, eyeshadow, just a hint of blush on my cheeks), before putting on my lingerie and dress. The cuffs and choker, along with my wig and Mary Jane heels would go into a bag for transport.

By the time I was dressed and ready it was…oh, I was ready about 4 hours early, lol. Ok, so maybe I need to dampen my excitement a little.  

I managed to see out time to 2 hours remaining, before deciding to leave. It was only a 1 hour drive but I didn't want any chance of being late.  

Typically the journey could not have gone better, and with about 10 mins drive left, and over an hour before I needed to be there, I pulled into a service station for a nature break and a nice canadiacano* 🇨🇦 coffee.  

*Sorry America, it sucks when things named after you are just randomly renamed, right?

I'm not sure what sissy is referencing here. Maybe a stab at numb-nuts in the U.S., trying to rename the Gulf of Mexico? 

In which case, I propose that we start calling the Great Lakes, the Great Canadian Lakes!

After finding parking and walking past Lady Jose’s place once and round the block to waste a few more minutes, I finally pushed on the door to her place and entered, no going back now, alice!

Lady Jose was so welcoming, and incredibly gorgeous! I mean wow, She was dressed in a satin green dress, the shape of which teases glimpses of the hosiery and garter belt underneath. Beautiful pearls around her neck and black heels adorned her feet. She looked amazing, but it was her smile that really caught my attention.   

A smile like that goes such a long way. Her warm greeting helped put me a little at ease as I scanned the room.

Part of the room was made out as a living room, a chaise lounge, small ornate coffee table and other chairs, along with pictures on the wall and a dressing table. I spotted a bench on the left that adorned a number of spanking implements, and on the coffee table lay a couple more.  

Carefully placed to catch the eye, but not totally in your face. It was so well visualized, the whole room.  

Quality implements, Lady Jose. Well done! That's one element that truly makes a difference in a discipline session. 

I was offered a coffee and asked if I would like to chat first or change. I opted to get out of my boy costume so went round to the toilet and stripped off my disguise.  

My heart was thumping now, I could hear Lady Jose and the click click click of her heels getting things ready, and with one final deep breath I stepped out to face someone in real life...as alice.

I was taken aback at how complementary Lady Jose was to me, she absolutely adored my outfit and kept telling me how pretty I looked - me, pretty! If I wasn’t blushing before I was now! We sat down and talked, about me, about Mistress and such, how I got into kink. It was friendly, welcoming and helped me settle in.  

All of the scene had been discussed between Mistress Andrea and Lady Jose in advance, but it was nice to clarify and agree on what was going to happen. We also agreed on a safe word system (red/amber/green) and before I knew it Lady Jose smiled, sat up that little bit straighter and said those wonderful words.

“So alice, are you ready for your spanking?”

I was sent to stand against the wall that would be, for this session, “the corner”, my heart thumping out my chest. I was so nervous, it was all about to happen.  

I don’t think I was there long before Lady Jose called me out and directed me to stand beside her.  Pointing at her lap she said, “you are going over my lap for a while now, alice, you will be there a while and your bum is going to hurt after.”

I laid over her lap, felt her place one arm over my back to hold my hip and it started. Softly at first, with my dress covering my bum still.  A gentle hand spanking warm up. It felt so good, the arm around my hip, the rhythmic slap slap slap of the firm hand on my bottom. I was told how pretty my dress was, as I was laying across her lap being spanked.  

Lady Jose paused briefly to pull up my dress and compliment my satin panties before resuming my spanking.

With one less layer protecting my skin the spanks began to get stronger, and my bottom was starting to warm up.  

In the next pause my panties were pulled down and we were into full bare bottom spanking. It felt incredible, her hand was so firm, the spanks so consistent as they slowly built up in intensity as my spanking progressed.  

Eventually there was a pause and I was sent back to the corner, to show off my pretty pink bum. As I stood with my nose to the wall, I could hear the click click click of heels behind me. I guess Lady Jose was taking pictures but also getting the next stage of my spanking ready.

Sure enough I was called back over Lady Jose’s lap, for more hand spanking. To be a 40 year old man dressed as a little girl, bent over the lap of a gorgeous woman whilst being spanked is a humiliating experience! The spanks were getting harder now, and eventually I was letting out small moans with the strikes.

"There, so you CAN make sound after all, Alice,” I remember Lady Jose joking. Guess up until then I had been rather quiet, trying to take in the whole experience spank by spank.  

Lady Jose had already told me the order of what was to come next in the pre chat - hand, leather, wood.  That was the order. Softer at first and building up intensity. I was living exactly what Mistress Andrea had written in the lesson about maintenance spankings! It was like these two had been to the same spanking school, or borrowed each other's textbox on administering a proper spanking. 

Lady Jose finished the hand spanking and soothed my now pink behind with her hand. The feel of her warmed hand over my bum was so arousing, I was nervous I would leak on her dress! My clit-cage was coming into direct contact with her lap, the little pink nub of a chastity cage that I had been locked into for 203 days at this point. 

Then, a new sensation, something cooler was slid over my bum, and Lady Jose informed me this was one of two leather paddles I would be receiving.  

The swats were harder, making me groan with each one. I could feel my sit spots start to complain when the strokes hit in that perfect spot as the two different types of leather paddles were used to add yet more depth in the colour of my bottom. 

 

I think it was now that Lady Jose used her nails to gently glide across my spanked bum - oh boy what a feeling. So sensual, so soothing! Before I knew it I was nose to the wall again as click click click went those heels, getting the next stage ready. Leaving no uncertainty that I was being disciplined by a woman!

I was called back and this time was told to bend over the arm of the chaise longue. It was time for my belt strapping.

Now the feel of a belt swatting across your behind, when wielded by someone with the expertise of Lady Jose is a wonderful experience. The sound, the feeling, the intensity!  

I know I am a bit of a masochist so I really liked the belt, grunting as each blow hit. It was intense, but at the end Lady Jose asked how that was, on the traffic light system. In my state of mind I said green, the last spanks hurt but overall it was fine. 

Probably not the best strategy, alice, telling a professional disciplinarian that "it's fine" after she's tanned your butt with a belt. Tsk tsk.

“Go to your corner, I have just the thing for a little pain sissy like you,” Lady Jose hissed.   

Nose to the wall I listened as her heels clicked off into the distance. Then the clicks returned, and Lady Jose came next to me, told me to look at her and held up something called a Canadian prison strap. Oh my, that thing looked intimidating.  

* Another Canada reference 🇨🇦 today, it’s like it was written in the stars ✨… 

Now the leather belts hurt, but the prison strap was so much more intense. Each stroke made me cry out as Lady Jose expertly wielded it's fury. 

“This is what happens when you say green to a true Disciplinarian, sissy!  What colour is it now?”  Lady Jose asked after finishing.  

Haha! Told you so!

My first thought was ouch, that thing hurt a lot. Yet part of my brain, thankfully a very small part, was begging for more.  

“Amber now Ma’am, definitely amber!” I cried out.

* Later, Lady Jose would tell me that the strap was a lazy spanker’s dream implement. Minimal effort to use, maximum effect on the butt!  

After a short corner time pause, it was time for woods. Lady Jose had selected a beautiful dark wooden hairbrush with an inlay, “A beautiful implement for a beautiful sissy spanking!”

Antique ebony hairbrush maybe? Those are frightening. And I think I saw one, at the ready. 

Yep. Right next to those super-cute hour glasses that I would totally use for lengthy corner time. 

With the focused areas of the small brush, my sit spots were really hurting now, I was crying out like a little girl with every blow. There were a range of paddles, I lost track here now a little. There was another small brush, a large brush, a olive wood spatula (apparently it’s a very strong wood - good to know given my old spatula broke a couple of weeks ago!) and a bath brush.  

I hate bath brushes, damn the hurt - Lady Jose said it’s down to the length.  

After more corner time, it was time for the most humiliating thing I have ever had to do. The wheelbarrow pose. Now I didn’t actually know what it was at first, but when Lady Jose described it, I was mortified! Positioned like that she would see everything, my most intimate spots! 

No hiding from anything, as EVERYthing is on full display. It truly is a very vulnerable and humiliating position to be spanked in.

Positioning myself, head down and straddling her lap, Lady Jose started playing my red bum like a drum, with the spatula and bath brush, and I was so humiliated I hate to say I started giggling. I couldn’t help it! Those sorts of situations sometimes make me laugh uncontrollably, it’s the nerves. Lady Jose didn’t like that, slapping harder I was told, “this is not supposed to be funny alice, this is supposed to be humiliating!”  

Ummm...ya. Once again, probably not a good idea, alice. You and I are going to have a little chat about this part, young lady!

Oh Lady Jose, it was sooo humiliating - hence the nervous, uncontrollable giggling. I was so sorry for that, believe me.   

You're going to be! 

It was approaching the end of the session, but there was time for one last position. I was instructed to lay down onto the chaise longue once more, on a towel and pull my legs up high, diaper position, the second most humiliating position I could be spanked in. 

Holding the bath brush it felt like Lady Jose towered over me as she inspected my behind.  “This is the only position you can look someone in the eye as you spank them.  Look at me alice,” Lady Jose commanded. I felt so small and childish, with my outfit to reinforce this fact. I felt like her naughty little girl. 

If being spanked isn’t humiliating enough, if spreading your legs so wide you expose every part of you isn’t mortifying, try looking someone in the eye as they spank you. I just couldn't do it for long, it was so humiliating. My tooshie killed now with every stroke, every blow of the brush. With a final 6 swats Lady Jose seemed content with her work.

For one final time I was back in the corner. This time Lady Jose informed me she was messaging Mistress on how I did and sending her images. I was so nervous, what would Lady Jose say, what would Mistress think??

What Lady Jose told me at the time was that Mistress really liked Her sand timers…..  😂🤭  I hope there was more in there, maybe something about my tooshie but still, they are lovely sand timers admittedly.

I told her to give you 20 minutes in timeout, which was covered in the last post. She's a professional disciplinarian of international esteem, she doesn't / didn't need my help. Just look at your naughty bum, she's a pro. 

Even on the eve of your session when she asked me what implements I'd like used on you, I made a few comments but again, she didn't need my two cents. My gift to you was just getting you there in the first place ; ) 

It was humbling to think these two divine, majestic, dominant women were conversing over me, little old me, as I stood in the corner with my panties hiked down and my bum bare. I have no idea how long I stood there, Lady Jose occasionally said something from the conversation with Mistress. I was so content at that point, nose to the wall, my bottom glowing hotter than it ever has before knowing I was being spoken about like a naughty child in the corner. Corner time is so powerful, so therapeutic at times like that.

This was my gift from Mistress Andrea, the most wonderful, amazing gift delivered by the amazing, beautiful Lady Jose. I was so honoured by it all, sad it was over but so grateful none the less.  

After some time I was called out of the corner and the situation felt immediately more relaxed.  Lady Jose offered me a coke, or fanta, and it suddenly dawned on me that I could really do with something sugary. I cannot remember if I changed first, or if we sat and reviewed the pictures taken first. It was so nice to have a relaxed conversation after such a thrilling session, it helped finalise things in my brain, just as corner time is such a powerful time post-session, to allow the mind to process all the buffered thoughts from the experience. We spoke about what worked, what could be done differently next time, about other fetishes and such. 

With a final hug (Lady Jose gives the best hugs by the way!) and some more kind words, I was on my way, a spring in my step unlike anything before, the cool air invigoratingly fresh on my skin.  I messaged Mistress immediately to tell her how well it went, and headed to my car. I couldn’t wait to get home and debrief Mistress on what had happened that day.

Mind you, the drive was less than comfortable, next time I think I'll need a pillow to sit on!

In very short order, the same day as my session actually, Mistress Andrea made a post about it and it was the first time she called this entire experience a gift, to me! I became emotional almost instantly, with tears blurring my vision as I continued to read and absorb the magnitude of exactly what she had done for me. 

I will never, ever forget how wonderful of a gift this this was. Thank you, Mistress Andrea. 

kisses everyone

alice

P.S. I've already booked another therapy appointment with Lady Jose. Apparently she and Mistress Andrea are already cooking up some details about the session. It sounds like I'm being "sent" to stay with my strict but caring "Auntie", and Auntie doesn't care for boys. She always wanted a little girl of her own... 

If permitted, I'll post again, after I've been back across Auntie's knee. Would that be ok? 

Very nicely done, alice. You've earned the ability to post on my blog with that wonderful content, your self-awareness and your willingness to continue this journey you're on. 

We'll see if your fans on here would like to see more of you. 

Mistress Andrea

xoxo

Continued in: First Time

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

Set, Session and Scene

Continued from: It's all in the Eyes

[F/f] [spanking] [humiliation] [cornertime] [anal]

I am going to resume my TED talk series on a few more aspects of the lifestyle that I feel are important to cover, then we are going to turn things over to Sarah Jane, who wanted to re-tell the story of her very first playdate with Mandy, orchestrated by yours truly. 

Unwinnable Circumstances

Cassandra was the queen of the head games, making silly male submissives choose between the lesser of two evils, or what they thought was the lesser of two evils. This form of psychological torture pitted her male clients into predicaments within themselves. Be fucked in the ass by Cassandra, or have another 90 days added to your chastity sentence, your choice. Sixty-nine with another male slave, or feel the bite of her single-tail whip. Then she would make them actually choose the path of their own torment, before carrying it out. 

Everyone always has a third choice too, being their safeword, but those are rarely used. 

What Cassandra won't do, however, what I won't do either, is to present an unwinnable scenario to a submissive, with consequences for failure. Take this example for instance: 

I'm going to tie up this lovely submissive, I'm going to rope-anchor the Hitachi against her pussy and then I'm going to turn it on, full blast. 

If you orgasm...you're getting punished! Then leave her to the disparity of the inevitable. 

I have electro-pads on Summer's nipples, there is a vibrating anal plug up her ass and the wand is locked onto her pussy with one of those trusty, lockable, vibrator belts. I might tell her she's not allowed to cum, even threaten her about what I will do if she does...

But am I actually going to punish her when she cums? No. This is an unwinnable scenario and I'm not that cruel, plus, it will frustrate the submissive. 

A slow and steady handjob without stopping, while a bound slave just lays there and takes it. I've told him he's not allowed to cum under any circumstance, but I still keep my pace on his cock. 

I'd totally just edge then lock him back up if this was a real scenario. If you possess the skills to do a ruined orgasm, I would suggest that as an option too. 

But let's say that wasn't the goal and I just wanted some head games at play, violently jerking him off while telling him how horrible his life is going to be if he should dare cum in my presence. He's going to fail, it is inevitable. I'll make him consume his mess, to shame and humiliate him, but I'm not going to punish him for cumming, this was an unwinnable scenario. 

Set, Session and Scene

These three terms speak to the planning phases of a playdate, based on what the submissive wants and how I intend to deliver their fantasies.

A session, is the entirety of my interaction with the submissive. A session could last for several hours or even several days, where breaks can be taken into the vanilla world and into vanilla activities, but everyone remains in role, everyone abides by rules and structure, along with official titles. 

A scene, is a specific activity performed within the session. I spoke of admin and ops in a previous post, being two different things but interconnected overall. This would be an example of two scenes within one session, complimenting one another, doing admin before I do ops. 

Let's say for instance that I'm having a session with Mandy. I have told her that I'd like her age regressed when she arrives to my house and that she will be seeing "Mommy" today, for a spanking. 

We're going to do all kinds of other stuff today but I'm starting with admin, vulnerability and humiliation to kick-off the session and this maternal-style spanking becomes our first scene. 

As for sets, this would be the breakdown of my first scene, it's very easy to organize. 

Set 1: Mandy will do 20 minutes in the corner of the living room with her bum bare

Set 2: Called from the corner for OTK hand-spanking

Set 3: Have her fetch "Daddy's" belt from bedroom, give a strapping over the arm of the couch

Set 4: Wheelbarrow pose for the leather paddle

And so on, and so on, set after set, you get the idea. 

Set 9 (for instance): Finish her in the corner for another 20 minutes, bum bare.  

I said before that admin should be real and predominately non-sexual in nature, and in this example, it absolutely was. However, Mandy needs to thank me, "properly", for her spanking, and this is now where ops begins to creep into the admin. Her humiliating attire hasn't changed, my maternal attire hasn't changed, yet I planned ahead to ensure I was in lovely, vintage lingerie, under my pinup dress. As for her, I want her to be engaged in sex acts while still in her age regression clothing. There's a taboo about it, there is a humiliating vulnerability about it, and I want her to experience and tap into this. 

We're still in the same scene, about to begin Set 10, our surroundings, our attire, has not changed and this is why it is the same scene and not a new one. She's still calling me "Mommy", as I summon her from the corner and have her crawl towards me on her hands and knees. She will be made to worship my high heels, my feet, my bottom hole and eventually go down on me to completion. This is the manner in which I want to be thanked for taking the time to spank her. 

Now the scene has ended! I've just orgasmed onto her mouth and lips and she will verbally thank me for that gift, gazing down at the floor with her little pigtails cascading down her flushed cheeks.   

We might have a soak in the Turkish bathhouse that I installed in The Facility, we might go to the kitchen together and get some fruit. The session is still running, but the first scene has ended and she has no idea how many more I may have planned.

When I'm ready to begin the next scene, I tell her what to do and where to go. In this circumstance, this is what I wanted: 

I had Mandy stripped bare and vulnerable, still sporting the effects of scene one, when I brought her to the shower where I had an enema bag prepared and hung. I lubricated her, I probed her ass with a gloved finger, then inserted the enema nozzle into her bottom hole. 

Scene number two of the session has just begun. 

I began the flow of warm saltwater water into Mandy, rubbing her pussy and breasts, tweaking her nipples and offering her supporting words as she took the full two-quarts, her sense of urgency worsening by the second. I left her alone to do the next phases of clean-out by herself, while I went off to change into my scene two attire and prepare an outfit and the setting for the next phase. 

Based on my attire alone, you can tell that we are well into the ops side of the house now. Mandy doesn't know exactly what's coming but she can probably surmise that by wanting her fully cleaned out back there, she's going to be in for some heavy anal play. 

I went with a virginal white for her, to act as a stark contrast to the non-virginal acts we were about to engage in. 

And yes, I fucked Mandy in the ass while she got herself off with her fingers. 

She was treated to two orgasms with my girl-cock in her bum, then I rode her face for awhile as she diligently returned the favour. 

End of scene two, change of outfit. 

A lot of the time, this is an easy way to think about the structure. Each scene gets its own unique outfit throughout the entirety of the session.

I began scene three in loungewear and heels, because that's exactly what I wanted to do to end-off the session.

Mandy began scene three like this, serving me drinks and sucking on my toes as I savoured my drink and her lovely mouth. 

I even treated her to a little end-of-session, celebratory drink, but with a twist: 

Booze tastes better when suckled from the toes of a Dominatrix. It's a fact! ; ) 

I'll leave you with a final scenario to contemplate and I'll continue this learning series later on, as there has been an exciting development today that I want to write about.  

Here's the final two riddles: If you're a male submissive who has his penis in a chastity cage, and you do not have control over the keys to unlock that cage...does that mean you're like always in a session? 

If you're living a domestic discipline, female-led-relationship and that video radar, speeding ticket just arrived in the mail...and you have to give it to your wife to pay, because she controls all finances in the home...and you know you won't be sitting comfortably for the foreseeable future once you show her the ticket... 

Does that mean you're just constantly within a session? Underscored by scenes, like the one described above? 

Set, Session, Scene...Lifestyle is the fourth one, the missing link. 

We'll discuss lifestyle next time. 

Mistress Andrea 

xoxo

Continued in: Spanked by Lady Jose