Back to School

Continued from: Old Flame

A Sarah Jane story: Back to School

Hi everyone, it's Sarah Jane, or as Daddy and Bella started calling me, "the summer intern" *giggle*. 

It was a cute title. It made me feel youthful and a bit slutty. Like bending at the waist to pick-up a dropped pencil slutty, or deliberately bending over desks to read as the boss came in the room. I always made sure my skirt would ride-up during these moments, so my stocking-tops would peek through. 

If you remember, I was promoted into the role of Secretary at the Facility. I ended up spending much of the summer actually working in an office environment, with Bella and Daddy (who was playing the role of my boss). I spent an awful lot of time on my knees, with the boss' dick in my mouth. These moments were very pleasant for me and I loved that I was permitted to dress like a slutty Secretary.   

Other times, if I was naughty, things would become very degrading and humiliating. The boss would send me back to my desk after taking a facial from him. I would have to wear his cum on my face until the end of the workday, in front of Bella too! Which was the worst part. 

I was frequently required to sexually service her also, when the boss ordered it. I ended up becoming very well acquainted with her beautiful pussy.

As my summer internship being the office slut came to an end, I got a week off at the end of August. I think my "boss" was doing some other things with Mistress Andrea and her wife, Summer. I didn't ask or question, I would have been punished if I did.

Surprisingly, when I returned to the Facility after Labour Day, I was put through the full ringer and check-in process that any standard-issue client would experience. I was stripped of all my clothing and personal items. These were taken and locked in a locker and I soon found myself vulnerable and bare naked, standing before Mistress Andrea in her office. I thought I was in shit or something. 

My journey at this Facility started in a jail cell in the basement, in shackles...being brutally used, fucked and whipped, day and night, by my Master. (I loved every second of that phase!) 

Next I was put into adult diapers, and I had a Daddy Dom to care for me and correct me when needed. That period of time was probably the most humiliating for me, as an adult woman. 

Through several promotions for obedience and sexual exploration, I was dressed like a little girl, then a junior schoolgirl. As I spent some time in these roles, I became more enthusiastic about sexually pleasing women, which was completely new for me. This willingness got me promoted to senior schoolgirl and by the time I made it to the slutty Secretary phase, I was having sex with Bella on the regular. 

Now, I found myself standing before Mistress Andrea, bare naked, looking down at a school uniform and a pair of Mary Janes on her desk. I actually thought I was going to be spanked and demoted by her for some reason. 

It was quite the opposite actually. Given the date, she told me it was time to go back to school. Not for lessons or instruction though. This time, I was doing my final exams!

Mistress entered the classroom and produced a cane, a wooden paddle and a strap. She made it abundantly clear that I would be getting all three implements on the bare, if I did not get an 85% or higher on my exam.

This was the final test, literally, to determine if I would move on to the next phase and wow was it ever epic. Someone put a lot of time into creating this test. It was as humiliating for me as it was arousing. With multiple choice questions like: 

Select the answer that is the most correct:

You are kneeling and performing a blowjob on a random guest of the Facility. He has cum into your mouth. What do you do next? 

a) Swallow all of his cum and use my mouth to clean the rest of his cock. 

b) Swallow all of this cum and verbally thank him for it. 

c) Excuse yourself politely to go spit his cum out, down the sink.

d) Find a nearby slave-sister to kiss, so you can both share the man's cum

e) Swallow all of his cum, verbally thank the man, then kiss the tip of his penis 

There were true and false questions, along with every aspect of spanking theory and implement selection. There was even images of slaves in certain poses, where I had to choose the official title of the pose. Like this one. Which is called "present", by the way. 

Despite the significant length of this final exam, I was breezing through it with confidence. Every answer was jumping off the page at me, the rules and rituals and protocols that had been drilled into me since I began this journey, were all test questions.

I truly believe I nailed this test. I walked it back into the "Principal's" office with pride and handed it to Mistress Andrea for marking. She took a quick skim of the pages, then asked me to go back to the classroom to fetch the cane, paddle and strap...Uh oh! What did she see?! 

She made me stand in the corner and face the walls while she marked my exam. Also, she strategically placed the intimidating looking implements around and near me, so I could see them out of the corners of my eyes and become anxious.  

Mistress took her time with the marking as I was alone with my thoughts in the humiliating, time-out corner. As the minutes slowly ticked by, I began to second-guess myself and some of the test questions I could remember. 

There was one about ass-to-mouth and how frequently I should experience this degrading act, to remind me of my place. Shit...did I get that one wrong? 

There was a true/false question about always being on my tiptoes when not in heels. I couldn't quite remember...did I pick true on that one or what it a trick question? Fuck! My bare butt was going to be purple if I failed this test. 

My inner dialog came to an abrupt halt when Mistress finally spoke, asking me to stand at attention in front of her desk. 

She wasted no time in informing me of my results. 

"You achieved a 94% on your test, Sarah Jane. Very nicely done young lady." She said, with a tone of a proud parent. 

"You may remove your schoolgirl uniform and fold it neatly," Mistress continued. 

I undressed right away and knelt, trying to hide my inner joy upon hearing my exam mark. 

Mistress began to speak. 

"You're one step closer to the Upper Floor, Sarah Jane. I am proud of you." 

Awww! That was sweet of her to say. 

"You know you can safeword out of this arrangement and out of this place whenever you wish, okay?" She kindly said. 

I said, "yes Mistress Andrea," using her full title in my response. But my mind was racing. Why would she say something like that? I just nailed her final exam and I'm one step closer to becoming a sex slave of the Upper Floor. Was I missing something? 

"If you'd like to continue, Sarah Jane, I expect you to report to Bella down in the stables, tomorrow morning. I'll be joining you to begin your pony training."

Oh...right. This horribly humiliating phase! 😢

FUCK!

sarah jane xo

Continued in: Ponytail

 

Old Flame

Continued from: Jail Bird

What do you think dear readers? What would you do if you were Russell? He's currently in the arms of his 🔥old flame🔥, kissing her neck, just below her earlobe, with his dick locked in a metal cage. 

And MY Gawwwwwd, he's good at this! Goosebumps were spreading all across my body and my toes were curling!

(Speaking of Old Flames. If you haven't tried this brunette craft-brew, I would highly recommend it. It's toe-curling also. Port Perry, Ontario! - support local)

As Russell continued his exploration of THIS brunette, up and down my neck with his lips, I realized the silly man was just stalling, he had a decision to make. I had just offered him a wonderful yet horrible predicament. 

If you read the previous post you know he was recently spanked and strapped with a police-belt, by my two cute Officers. This was likely not arousing for him in the moment, but post-spanking, as he still feels and sees the effects of that belting, his arousal would begin to creep back in.

This was right around the point I locked his dick into a chastity cage, shutting down any and all penile activity without my permission. Once locked, he got to hear the two policewomen get spankings over my knee. Then he got to watch and hear them kiss, go down on each other and eventually me, as the scene culminated into a hot, lezzie threesome. 

All while poor Russell observed from this vantage-point:

And NOW...

I had just offered to unlock his penis to re-kindle an old role that he used to provide for me, when I was his submissive. The predicament part? If he wants to take me, right here and now, he has to celebrate Locktober this year, and submit to inescapable chastity for the entire month, with me as his keyholder. 

What would you choose, hmm? 

I know what Russell is going to choose. The fact that he's already been denied most of the day, spanked, then a helpless witness to a hot lesbian threesome, should influence his decision. Was this cheating on my part? Too much stimulus and influence over his decision making? Maybe a little...😈

But if that wasn't enough, I started rubbing the metal bars of his cock-cage against my pussy. Hehe. This she-devil wasn't playing fair at all! 

As expected, I was soon accessing the keys for his chastity device to unlock him. We switched roles right then and there, once his cock was free. I was now his submissive pet, to do with as he pleases. I was naked and on my knees. It was about to be a nice little vacation / slave-cation for me.

"How would you like me prepared for you, Sir?" I whispered out, in my most submissive tone. 

"A pleated plaid skirt, young lady, like you used to do for me," Russ said. 

I immediately felt a rush of adrenaline and arousal form between my thighs. "Schoolgirl", back in the day, usually meant a spanking, a really long one! But then he continued...

"Boots with your skirt please, my doll. A subtle nod to your current role." He smiled as he suggested this deviation from the norm. 

Oooo, ok. I can get behind this idea! Rather than the innocence and vulnerability of white knee socks and Mary Janes, Russell clearly wants me a bit more edgy and "grown-up", not so innocent perhaps?

Before heading off to prepare, Russell stood me up and performed a wet-check. I was embarrassingly soaked for him. I shuddered with ecstasy as his manly hand cupped my pussy, his two middle fingers explored their way deep inside. 

Those two fingers ended up in my mouth, where I shamefully and greedily sucked them clean, like a huge slut. Russ had me right where I wanted to be, panting and hypnotized with submissive arousal. 

I returned a while later, dressed and ready for Russell. I was feeling both sexy and vulnerable in my new look. Without being prompted, I knelt to await my instructions, noticing that Russell had moved some of my furniture around and positioned a few mirrors, strategically, near the bed. 

"You look beautiful young lady." 

"Thank you, Sir."

"Come here, little one." 

I was all melty and gooey in his strong arms. I was right back to the sub-space I once enjoyed with Russell. I felt so safe and cared for. He was my protector!

Pretty soon he was patting his lap invitingly. I rose from my knees slightly and slowly and deliberately slithered my mid-section over his lap like a snake. 

I got a mild spanking with his hand, over my skirt, then over my panties until those were eventually peeled down and off my feet. 

We moved to the bed and my spanking continued. Only this time, Russell would spank and finger me, spank and finger me. I even felt several swats directly onto my pussy lips and bottom hole. Shamefully, I think I was moaning like a whore the entire time. But I didn't care. Tonight, I was his whore, and I was loving it!

Russell, much to my delight, busted out some old-school tactics he used to do back in the day. While I was still draped over his lap being systematically spanked and fingered, he used my wetness and transferred it onto my little bum hole, until it was glistening and slick.

Let me repeat that...

He used my own arousal as lubricant for my asshole! What a freakin' stud he was.

That being said, the butt plug that came next slipped into my bottom with ease. He then removed my top and gagged me. 

Another of his old moves. Having me ride his tongue while I'm anally plugged and gagged, with a mirror to stare into.

When he flips me around to face his cock, it's frustrating because I want to inhale the entire thing, but my gag remained in place. In this position, as I grind my pussy into his mouth, his nose presses on the base of my anal plug. I get a joyful little ass-fucking sensation because of this and I was soon screaming into that gag-ball as I came. 

When I ride his tongue, Russell actually edges himself. Just slow-stroking his cock until it's ridiculously hard for me. Boy, did I ever get fucked after that! Sometimes I was allowed to be in control of the speed and tempo. 

Other times it was all him. 

When I was made to face the mirror, he ensured a sharp tug to my ponytail would remind me to watch. 

Around this point he was taking frequent breaks, fighting off the urge to cum so he could extend our playtime as long as possible. He would pull completely out of me and I could hear him heavy breathing, it was cute. Then I would feel the awesome and full sensation of his cock slowly re-entering, competing with the contours of the anal plug, pressing against my vaginal wall. 

The reverse pressure of the anal plug is also an incredible sensation for his cock. The poor guy held out as long as he could, edging himself each time he had to stop, then re-start. Eventually he absolutely unloaded into my pussy while he clawed at the bedsheets and shook like a leaf. 

He could barely stand afterwards, his knees were so shaky. It was super cute, to have this paralyzing effect over a man from a position of submission.  

You know what else was cute? Seeing his belt-strapped little bum while we had sex. It was almost as red as mine, and his spanking from the girls was hours ago!

I ended up getting another one, with his firm hand, in the dreaded wheelbarrow position. EVERYthing is on display when you're put in this pose and spanked. There's no modestly whatsoever. He would have had a good view of his cum oozing from my puffy, red pussy. 

He actually chose this one specifically so he could pull the anal plug out of my ass. 

Disheveled, sweaty, sore...and completely blissful in each other's arms. It was exactly as I remembered our times together. We popped some champagne and got right into some pillow-talk, as Russell helped me out of my hot boots. 

I was beyond content! Recently Domme'd by Goddess Vanessa, now Dom'ed by Russ. I was a lucky girl. I certainly had my fix of submission for awhile. I decided to return the balance of things and remind Russell of our Locktober agreement. 

"Yes Mistress Andrea." He replied with a cute and bashful smile. 

His gaze was locked onto me, he gazed directly into my eyes for what felt like an eternity. It was a look I had not seem from him in over a decade. I felt it penetrate my heart. I tried to lighten the atmosphere. 

"Did you ever think we'd end up here? The two of us with spanked bums, pretty much running a harem of BDSM enthusiasts and re-connecting the way we have?" 

"Never in a million years, huni." 

"Russ, I've never told you this before, but I love you...I always have."

Oh FUCK! Fuck, what did I do?! I had no idea where that suddenly came from. I was literally holding my breath until he said something. I couldn't look at him. He had tears in his eyes and it was gonna make me cry too!

He finally did speak, as he drew me close onto his lap, shielding his face in my neck to hide his tears. 

"Andrea, it's been ten years..."

"And not a day went by that I didn't think of you." 

😢💓

*sigh*

Be still, my heart... 

Mistress Andrea

xoxo

 

Continued in: Back to School

 

Summer gets caught!

Continued from the storyline of: Sissy sucks and cucks

What's the expression? When the cat's away the mouse will play?

Clearly I haven't been keeping my little tart, Summer, on a short enough leash. I think she's currently in Chicago O'hare, on a layover. Out of mere curiosity, I happened to check her secret little "fans", buy and sell site that we used to play out a fantasy of hers: Summer is spanked by the Pilot

Much to my surprise, look what I find. A new post from her hotel room in Chicago!

She wrote a caption to separate this picture and the second one below, that she posted of her feet and heels. It read: 

French-cut, 40D pantyhose, in my leather pumps for a six-hour Venezuela to Chicago.

It feels so great to take my heels off in the hotel room!

Then the audacity, at the end of her post:

Starting bid, pantyhose: $18.00 USD

Starting bid, full leather pumps, size 7.5, two years old, 100+ flights: $99.00 USD

What a naughty little girl!! Ohhh she's in deep shit with me. I text her right away. 

I have come to learn that Summer's fetish and fantasy as it relates to adult spanking, needs to be real for her. She needs to feel like she is actually being punished for something in her real life, not a made-up roleplay of schoolgirl / Principal for instance. She actually wants and needs to have real-life consequences for her actions.

Did she bait me, and make that sales-post thinking I'd catch her and punish her? I don't think so in this case. I think she genuinely would never have assumed I would look there. I'm not buying cabin-crew tights, why would I ever be on a site like that. 

I left her hanging in anticipation for a bit, then sent a follow-up message. 

Pro tip: Use the middle name too, when spanking an adult submissive or letting them know that one is coming, but don't overuse it. It's vulnerable, it's childish and places you into that Mommy or Daddy, authoritarian, care-giver role. 

You want the use of their first and middle name to be serious and rare. It will conjure that deep, pit-of-the-stomach despair that Summer is now experiencing. She doesn't need a plane and a pilot tomorrow, the butterflies in her stomach will flap her home to Toronto. Ha! 

Again...this is what she wants. This is how she wants to be disciplined as an adult. 

I didn't tell Cassie what was up, I let it come as a surprise to her the next day. 

"You've reached The Facility, this is Cassandra speaking, how may I help you?"

"Cassie, it's Summer. We met in the dungeon space that day, remember?"

"Of course Summer, why are you calling in on this line, is everything ok?"

"Oh yes yes, well...no actually...ummm. I have to book an appointment to be punished".

Cassandra paused for a moment. 

"Well in that case, it's Miss Cassandra, are we clear?"

"Yes Miss Cassandra". 

"Let me start a new file for you here and take down some information. Can you tell me the reason that you're booking a punishment?"

Summer was incredibly embarrassed, but slowly and methodically proceeded to tell Cassie what she was caught doing and why I needed to punish her. 

Cassie, on the other end of the line:

"Really? People pay for those things?" 

I can't say I blame Cassie, that was my initial reaction too.

"I'm going to email you a confirmation and a consent form Summer. You're booked for 10AM tomorrow morning, I would highly recommend you be on time. Please fill everything out, sign it and send it back to me".

"Consent? Consent for what Miss Cassandra?"

"On the form you're basically acknowledging and consenting to the possibility of seeing other naked adults or being around complete strangers in various forms of undress". 

"Oh...ummm. Thank you Miss, I'll see you tomorrow. 

That's right! It hadn't dawned on me until now. Summer has never experienced the formalities of a session booking at my facility. She's either been straight to my bed, straight to the gym or most recently, beating a slave-boy in my dungeon space. Domina debut

I was kinda eavesdropping from the kitchen when that call came in. I tried to play it aloof with Cassie and clicked into the waiting room, just as she was finishing up on the phone.  

"Mistress Andrea, that was...ahhhhumm, Summer". Cassie said, sounding surprised. "Aren't you two like dating?" She asked. 

"I'm not really sure what we are Cassie huni, playmates I guess. Did she just book an appointment?" I asked her. 

"Yes Ma'am, for tomorrow at 10", she replied. 

"Mistress, is she..."

Cassie paused for a moment. 

"Am I to give her the FULL 'check-in' experience Ma'am?" Cassie finally asked, while slightly cringing. 

"Yes Cassie, she's here tomorrow to be punished", I said sternly. Then I asked if her if I had anyone else booked for 10. 

"Yes Ma'am, Kyle is booked too. A 'Mommy' experience, he has indicated on his request form this time", Cassandra replied.

"Oh perfect! Summer is going to be seeing 'Mommy' tomorrow too. It's exactly what that naughty little girl needs! Did she tell you why she's being punished?" I asked Cassie. 

She giggled out loud and replied yes. 

"Have you seen what she and some of her co-works post on their fan-sites?"

I grabbed my phone and showed Cassie an image from a previous post, of Summer's co-worker, Vanessa, who was posting her nylons for sale. 

She scanned the image for longer than I expected, before blurting out:

"That's kinda fuckin' hot Ma'am". 

*sigh*

"What am I gonna do with you Cassie!" I sighed and shook my head.

"Language young lady!” Was all I could think of saying to fight off my laughter. 

Mistress Andrea

xoxo 

Continued in: Crying is not a Safeword

  

 

Bella's Pony Play

Continued from: The BDSM Spectrum

I have an amazing pony play session all lined up for Bella, do you think I can find my fuckin' beige riding breeches? The ones that look amazing with black boots. The ones that are so tight across my gorgeous ass, that they look like they're painted on?

F**k!

I had to take things in a different direction with my attire. I decided on a mixture of formal equestrian wear, combined with Yellowstone, slutty and crazy barrel racer. I'll still look hot, Bella will be a puddle for me regardless. 

I wasn't able to find an actual barn, play space. They were all either dirty or smelly, so I decided to renovate my dungeon space for this session.

Bella was booked. I sent her some online porn homework, to explore and report back to me on. She had never seen pony play in BDSM before. I set her up with some material and videos to review. 

She was absolutely horrified at what was to come, and excited, embarrassed, aroused and soon to be humiliated. The contradictory cocktail of emotions she must have been experiencing, leading up to this day, I couldn't even imagine the butterflies she must have.

I told her to dress "country-slutty" for me. There would be no check-in with Cassandra this time, no anticipation or waiting. Bella knew she was getting a spanking first, then taken right to the "barn" next. If she fussed, the spanking would quickly become a woodshed strapping.  

I hiked her little ripped jeans down, her panties next, and started-in on her bare bum. A steady and meaningful hand-spanking. 

When I got her jeans and heels off, it turns out she wore nude stockings under her jeans, so the nylon pops through the jean-rips, to give her legs a flawless appearance. Cute idea, I thought. 

Bella received a nice, long warm up, before I asked her to kneel in the pose she is familiar with, we call it "open". 

"No timeouts in the corner today young lady, remain in "open" for me while I change. Get your hair into a high pony, you're not to move and you're to keep your legs spread and cunt displayed. 

"Yes Ma'am", she obeyed and blushed at my crass choice of words. 

I returned to find her in the same pose, trembling with anticipation and soaking with arousal. I clicked closer to her in my boots, inspecting her positioning and her ponytail. 

She knelt deeper, to kiss the smooth leather of my boots as I invitingly outstretched a foot. 

"Mmmm, good girl", I purred. 

I put Bella in a head-harness, mouth gag and leather collar. I led her to the dungeon and into her new pony stall. 

The setting was perfect. I could see Bella's eyes darting around the space. Likely mortified that she had been placed in a make-shift, horse stall with a straw floor. 

"I have to get all your tack on slave girl". I said to her. 

"But first, I need to calm that pussy down a bit. You are WAY to aroused right now", and I shook my head at her. 

She groaned into her gag, utterly ashamed over her soaked pussy, reacting to this environment. 

We got her into stockings and pony boots, which buckled and padlocked to her feet and knees. 

I helped her up onto a wooden pony, torture device and watched as she lowered her weight onto the unforgiving spine. The next little while will be spent watching her shift and adjust, trying to keep the painful pressure off her pussy lips, clit and asshole. 

After a solid 15 minutes on the wooden horse while I sat on a straw bale and watched, I asked if she was ready for her pony plug. The alternative option I gave her, was to just stay on the wooden torture horse. 

She cried and nodded her head. Bubbling spit from her harness gag in an attempt to say, "plug please, plug please Ma'am". 

I re-bound her in strappado, so her creamy little asshole was pointed directly at me. I chose a lovely and sleek, black-haired butt plug to match her actual pony tail. It looked beautiful on her. Or in her, rather. 

Next came a stainless chastity belt, to keep her pussy locked down and out of play. Her plug tail cascaded nicely from the anal opening in the chastity belt. Another head harness with some padlocks, an arm binder and finally, a nipple chain with some bells, she was all set. But my gawd was she ever humiliated! Her eyes were bloodshot from the stinging of her tears. 

I penned her up in her stall and locked the gate. Then I just sat back to watch her attempts to balance on the awkward heels, squeeze and contract on her plug, and jingle about from her loose and flopping tits. 

As some time passed and her struggles intensified, I asked if she was ready to go outside for some trot and prance training. 

Her eyes widened from behind her face harness. She shook her head violently in protest. 

I led her from her stall by her harness reins and whipped her in a crouch position. 

Eventually I returned her to her stall and calmly spoke. 

"Do you need to safeword out, Bella?"

She shook her head no. 

"Then it's time to go out the back for some prancing", I replied. 

She groaned and cried, but eventually lowered her head and allowed herself to be led outside by her reins. I could only imagine what was going on under the metal shrouds of that chastity belt. I bet there was an absolute frenzy in the works. 

I told her how I wanted her to lift her knees high and prance. Very controlled, very dainty. She practiced on the spot for me, while scanning the horizon and windows for any peeping neighbours. 

She did a quick trot for me, then a prance. All while I whipped her bare butt and flanks, encouraging her to keep her knees up and move slowly and under control. 

I saved her from any further embarrassment and led her back to her stall inside. I'm sure her humiliation levels were at the critical point, yet when I bent her over her stall to remove her tail-plug, I saw what success looked like! 

The poor, poor thing! She just can't help it! Little spider-silk strands of cum, dripped from the metal screening housing her pussy. 

I kept her in her head harness and gag and entered her bottom hole with my strap-on, through the little opening that the chastity belt provides. 

Before long she was screaming and making sounds through her gag that I hadn't heard her make before. I slowed right down and stopped. I thought I was hurting her.

She began to violently shake her head no and started to buck her ass and hips back into my harness, fucking her own butt with the dildo. I held her reins to control her bucking and to pull back on her gag, but she only got more frantic. Her tits continued to bob and jingle with abandon, perfectly framed and presented by her armbinder. 

She didn't want me to slow down at all, she wanted me to....

OMG! She was cumming from anal only! 

She was screaming "NOOOO" and "FUUUUUCK" at the top of her lungs while her legs shook and liquid squirted from the screening of her metal chastity.  

I've never heard Bella swear before, not even during the most severe spanking over my knee... 

While we were debriefing this pony session and doing aftercare, she pinned me down all cute-like, wearing my hat too, which made her even more cute. 

"Mistress, what the fuck was that?! What did you do to me!!?" 

She gritted her teeth and pinned my hands down, trying to act serious. 

I indulged her passionate cuteness and fought her off, up into a sit. I kissed her deeply. 

"I think someone likes being a pony slave, that's what happened”, I purred. 

"Oh Gawd! Thank you Mistress!", she sighed and groaned in embarrassment.

"Did I actually cum and squirt from being assfucked, Mistress", she asked me innocently. 

"Why yes you did, pony slave", I cooed.   

Mistress Andrea

xoxo

Continued in: Sissy sucks and cucks