Sissy School

Continued from: Wait for him by the door

Based on the progression of these latest stories, you can now see how this poor sissy's weekend of kink-captivity is organized and structured. 

Arrival and check-in was the initial transformation on Friday, the application of pretty nail polish and make-up, then a slutty sissy outfit. Saturday was a full day spent in a lockable maid dress with all the trimmings and now, on Sunday, Lexi was dressed and ready for "Sunday School", having just performed her morning ritual. 

Under the watchful eye of Erin, Lexi would be writing punishment lines on the chalkboard, sitting quietly at her desk and reading sissy erotica and basically spend the entire morning in a form of detention. Under his little plaid skirt were delicate, silk panties in stark white. Under his panties, his tiny pink chastity cage housed his denied penis. 

The schoolgirl look was deeply humiliating for Lexi. He was even made to wear a bra that matched his panties, with little fake, A-cup titties inside. What was most dreadful and butterfly-inducing about Sunday's however, was that Sunday was the real spanking day. 

Lexi was given an entry spanking on Friday night, over Erin's knee but that was nothing compared to what was to come. Lexi knew that around noon, his fantasy Sunday School day would end. He would be held behind after class to be caned by the teacher for poor behaviour. 

Then, with a note from the teacher in-hand, his fantasy takes him "home", to a domestic setting, where he has to hand the teacher's note to his strict parents. Apparently this was a thing back in the days of school-endorsed corporal punishment. If you were caned or paddled at school, you'd absolutely be getting the belt or hairbrush back home by Mom or Dad. 

This particular sissy, wanted the type of spanking that didn't really begin, until he is wishing it was over, with plenty of kicking and crying like a little girl. 

The school bell snapped Lexi from a trance-like state at his desk. Erin, playing the role of the strict teacher, stood and beckoned the naughty schoolgirl over near the pommel horse. 

"You know the drill young lady," Erin spoke and patted the top of the horse. 

Lexi lowered his head and began to remove his skirt completely, followed by his panties. Both were neatly folded and placed on the teachers desk. Then, Lexi draped himself over the pommel horse, standing on his highest tiptoes with legs spread. 

Erin gave the humiliated sissy 18 strokes of the school-cane and made him count them aloud, thanking her after each stroke. The caning left Lexi with a lovely pattern of raised welts, from his upper buttocks to the backs of his thighs. 

He was then placed in timeout while Erin prepared a note for his "parents". 

As the fantasy day continued for Lexi, he now found himself standing before Mom and Dad, handing them the teachers note and explaining that he got in trouble at school and was caned. 

"Go select an envelope young lady", Erin ordered, now playing the role of Lexi's Mom. 

"Yes Mommy," he replied. 

Lexi shamefully clicked out of the room in her Mary Jane heels and crisp knee socks, and down the hallway to the home office. She performs this same ritual every Sunday, while under the care of Erin and Brad, all while wearing different styles and versions of schoolgirl uniforms. 

On the corner of the desk in the office are a stack of manila envelopes. There is nothing written on them and they are in no logical order of any kind. Within the envelops is a single 5x8 card. Lexi is required to select an envelope, at random, and bring it back to Erin and Brad, unopened. 

On the little 5x8 card within the envelope, it will have one of two words written on it: 

Mommy

or

Daddy

As I'm sure you've already guessed, each week when Lexi performs this vulnerable ritual, the title on the card selected is the person who will punish Lexi. 

The embarrassed sissy will stand before Erin and Brad, unseal the envelope and look at the title on the card. Then he is required to say: 

"Daddy, may I please be given a spanking, Sir?" or;

"Mommy, may I please be given a spanking, Ma'am?" 

This is performed, all while he is dressed like a naughty schoolgirl, with his penis locked in a chastity cage, his wig in pigtails and heavy make-up on. My gawd I'd want to crawl right under the floor, this would be so humiliating! 

Is there a huge difference between a spanking from Mommy versus a spanking from Daddy, in Lexi's world? Apparently not a huge difference, both are serious spankings and always end in tears, both are predominately administered over-the-knee. With a Mommy-card selection, Lexi would likely receive her hairbrush. With a Daddy selection, he'll most definitely be getting Daddy's belt. 

Who's lap will Lexi's bare bum be draped across very shortly? What's your guess?

Doesn't she just look like she should have a wooden spoon in her hand? Maybe it'll be Mommy's strict lap this week.

Or, over one of Daddy's knees? So he can pin Lexi's flailing feet down with his other leg? 

Lexi stood before Erin and Brad and tore open the envelope...

Mistress Andrea

xoxo

Continued in: And the winner is...

 

Wait for him by the door

Continued from: Sissy's morning ritual

Brad actually works on Saturdays. So after fucking his hot wife, having his dick cleaned off by his wife's sissy slave, he hit the showers, changed and left for work. 

Meanwhile, Lexi was being dressed into his frilly maid attire with stockings and heels, and layers upon layers of ruffles and bows. 

Saturday is the first full day of his sissy captivity and all he has to look forward to are lists upon lists of chores. 

All domestic duties that Erin would be doing while her hubby is at work, are done by Lexi. Chores like handwashing Erin's panties, the soiled ones that sissy so diligently held against the wall with his nose, is an example of one of these chores. 

And Lexi does all of this, with an anal plug up his ass. 

Toward the end of the day, as Erin is finished up with her tanning, her shopping and a professional massage, she returns home to find Lexi still working away in the kitchen, scrubbing the sink.  

"Go wait for him by the door Sweetie," Erin would say to Lexi, usually about 15 minutes before Brad would arrive home. 

When he comes through the door, he is pleasantly greeted by the sight of a submissive and kneeling sissy maid.

"May I please suck your cock Sir?" Lexi has been trained to say, upon Brad's arrival. Sometimes he says no, but it's usually a yes, and he gets a full blowjob to completion, as soon as he gets in the door. 

What a lifestyle!

Brad will grunt and shiver through an orgasm, as bursts of cum ricochet off Lexi's uvula and get swallowed down into his tummy. An appetizer before dinner I guess. 

Brad and Erin retire to the parlour and are served drinks by their sissy maid, while he also prepares a romantic dinner setting for the pair of them.  

Saturday evenings, Lexi gets a little more involved in the sexual activity of this couple, as Brad fucks Erin's pussy, directly over his face. The sissy remains in his chastity cage and still in maid lingerie with heels. It must be dreadfully humiliating, to have Brad's balls bouncing off his nose and tea-bagging his face, as he fucks Erin.

This is one of the few times that Erin allows her sissy to lick her pussy. She just loves the sensation so much, having her clit licked while her pussy is getting railed. The odd time, Brad will dip his cock into Lexi's mouth, to give him more of a taste of Erin. 

Once Brad cums into Erin's pussy, Lexi's mouth is in the perfect position to accept the cascading goo, as it bubbles and oozes from her, directly down Lexi's open hatch. Lexi verbally thanks Brad for his cum, then it's early bedtime. 

Again, just like Friday night, Lexi is dressed in something skimpy, frilly and pink, and is put to bed by Erin and locked into the princess bedroom. 

By 8AM the next morning, he'll be back in the parlour, holding the giant, black cock in his mouth while he waits for Erin to get up. The morning ritual has begun yet again and Lexi will soon be back in their room, holding Erin's panty gusset to the wall and listening to this hot couple have morning sex. 

Sunday morning to be exact. One final day of sissy captivity, before Lexi has to bust out the nail polish remover and return to vanilla life, vanilla, notwithstanding his chastity cage and panty girdles.

Sunday's come with a routine and ritual also, you may even call it...Sunday school.  

Mistress Andrea

xoxo

Continued in: Sissy School

Thanking after Spanking

Continued from: Sunday Maintenance Ritual

In the domestic discipline relationship that Summer and I enjoy, not only is it important for us to adhere to certain rituals and structure, but it is equally important for both she and I, that I be thanked after Summer is given a spanking. 

It doesn't matter if the spanking is her weekly maintenance, or if she has been punished for a real reason. Summer is always required to thank me after her cornertime. 

In a male-led, female-sub relationship, this may appear as the wife or girlfriend, getting down on her knees while her husband stands, and takes his cock into her mouth. The mere positioning alone, is strikingly symbolic of the D/s roles at play. 

Yes, Summer does take my strap-on like this, after she has been spanked, but not right off the bat. First she worships her "Queen”. 

Essentially what worship means for us, is that Summer gives me a massage, all the way from my toes, to just beneath my earlobes, only using her lips and tongue. She is not permitted to have my pussy, until she has earned it, by pleasing the rest of me. Generally, she begins with my feet. 

Each toe is individually kissed, then sucked on. First one foot and then the other, before she moves on to my soles and arches. 

She will kiss and lick all the way up my calves and thighs until she reaches my bum, which she skips for the time being, moving to my other leg to kiss all the way down it, back to my ankle. It is quite the little tease to feel her warm breath, graze past my asshole and pay it absolutely no attention. But she'll be back!

The same cute little French kisses are now planted all over my bare bum and into my bum crack which she also licks the full length of. The tease this time, is her hot breath now on my pussy, which she won't go near yet. Eventually her sharp little tongue finds its way into my asshole and I completely melt into the bed. 

I raise and spread for her, so she can passionately kiss my anus directly, moaning out loud as she does.

She traces up my tummy and along the sides of my ribs, which gives me wild goosebumps. Such amazing chills that my nipples harden instantly, just as her mouth arrives up there. Summer spends a few moments on both breasts and both nipples, kissing and suckling away. 

When she finally reaches my mouth for a kiss, this is the moment she purrs to me and formally thanks me for her spanking. We usually hug at this point and tell each other, "I love you." Then she makes the slow and deliberate journey back down my chest and stomach, having now earned my throbbing puss puss. 

When Summer's tongue finally gets to her ultimate prize, pussy worship begins. She has earned it, after doing such an amazing job with feet, legs and ass worship. 

I cum repeatedly, directly onto her pouty lips, in a number of wonderful positions, eventually ending with a face ride...my all-time favourite. 

When I flip around and face her feet, she continues to diligently lick as my fingertips use her nipples as speed and depth dials. This pinching and twisting, also causes her to moan directly onto my wet pussy. The vibrations feel amazing. 

This whole worship and thanking process takes well over an hour, sometimes considerably longer than that. When Summer knows this stage has concluded, without being prompted she goes to our wardrobe and gets a strap-on harness, which she helps me into and attaches. This is the symbolically submissive moment, when she kneels and takes my cock into her mouth. 

Just enough to lubricate the dildo nicely, before I take in a handful of her hair and fuck her on the bed.

If she can cum from penetration only, which is rare for her, she may, but she is not permitted to manually masturbate her clit while she's being fucked. 

Is it more of a discipline fucking by that logic? I guess so, it's rough. The strap-on we use for "thanking after spanking" is considerably larger than a standard one or the ones we use on the sissies. 

When I pull out of her for the final time, she thanks me once again. 

"Thank you Ma'am." Sometimes, "thank you Mommy," I usually hear, depending on her mood.

Then, just like someone flipping a switch, we are back into vanilla mode. Outfits and toys and implements all get cleaned up. We end up downstairs in jammies, giggling and watching a show, eating popcorn. 

Vanilla, despite how Summer likes to dress around the house, which is usually "little", especially after she's been spanked and fucked. She even kept her hair bow in for tonight! What a cutie. I love her so much. 

Mistress Andrea

xoxo

Continued in: Sissy slave to a Couple

 

All Three Holes

Continued from: Objectification

A post from Sarah

When Russell returned to me I was whipped. 

I wasn't counting, but I am quite certain I received every one of the 100 lashes he indicated that I would be getting, before he left me to anticipate. He must have been using a less severe, more delicate flogger, as it felt like I was being whipped hard, with force, but there was no searing sting or incredible pain. 

My bare bum took the majority of the lashes, with some attention paid to my upper back and my thighs, above my knees. The sensation was incredible, my skin was electric and felt like a really good sun burn. I was so fuckin' horny for him, to be used by him for his pleasure. Most of his cum had since dried onto my face and wetness was glistening down my stomach from the drool escaping the base of the ball gag. 

When my bondage was finally released and whipping had concluded, I collapsed down onto my hands and knees, disgracefully cowering on the floor, begging Master for mercy. I offered up my holes, all three of my slutty fuck-holes, as an alternative to being beaten any further. 

Sure, I was acting a little bit, playing into my own fantasy of having my will broken, enough to submit to dirty, degrading and forceful sex. 

My ponytail was used as a leash, to guide and drag me over to the coffee table. He kept a firm grip on it throughout, as Master plunged his raging cock into my pussy. 

It was such an amazing fucking! It's making my toes curl even now, as I sit here in my vanilla, WFH office and write about this. 

We seemed to be very in-sync with each other, feeding off each other, in how this was all developing. While he was fucking me from behind he slipped a thumb into my asshole. Of course my naughty little pucker involuntarily gripped his thumb, which was horribly humiliating. I could feel my own asshole squeezing him, like I had no control over it. 

I cried out, "no Sir! Please no! Not my bum!!" I wailed loud enough that if Mistress Andrea was downstairs, she would have definitely heard me. 

I wanted nothing more that to be fucked in the ass by him, but I continued my ruse of non-consent. I'm a huge anal slut and wanted to cum while his dick was in my third and final hole. I just wanted Master to take, not ask. 

And take he did!

Master "forced" me to ride him reverse cowgirl, and do all the work. He just laid there motionless, as I was forced to bounce, with my tits shamefully flopping, and fuck my own asshole. It was so dirty and degrading I orgasmed instantly, with a little flicker of my clit. I kept on destroying my ass with his cock, then came again. 

My legs where shaking so badly I couldn't maintain the crouched position anymore. I sat right down on Master so the full length of his dick was deep inside, as he shot hot semen into my bowels. 

I'm sure I'm leaving out some other details of our time together, in the Parlour space. Times I was smacked and called names. Tormented about having dried cum on my face or a fresh, squishy load in my rectum. All of it added to the overall experience. I loved every fuckin' second of being flogged, broken and man-handled the way I was. 

I enjoyed that Russ didn't start the scene with a bunch of rules and protocols, or feel the need to go-over safewording. All of these things were assumed, before we ever began. The only thing he felt he needed to say, was that line from my last post: 

"This is what you want?"

Fuck YES it was! 

I was provided a robe. I guess to regain or protect what dignity I had left, after all three of my fuck-holes were just destroyed. Master wanted me in the heels I arrived in also, cute look I suppose. 

We retired to the kitchen and very sweetly, like I was the victim of a housefire or something, wrapped in one of those grey, humanitarian blankets, he asked me if I wanted a tea. Melted my heart a little, not gonna lie. 

I had not received a tour of this whole facility yet, I don't think anything would have surprised me though, based on the images I've seen on the client website. Over my right shoulder I noticed a large window covered with a thin veil of sheer, opening into what appeared to be a locker-room. My eyes caught movement and it appeared to be a middle-aged man, changing into an outfit like a little girl would wear. 

Russ went in for a closer look as Mistress elegantly clicked into the kitchen in a pin-up styled dress. 

"Did you two kids have a good time?" She cheerful asked out loud, like Russ and I were two teenagers returning from the movies. 

I blushed and lowered my eyes, squeaking out a little, "yes Ma'am, thank you Ma'am."

Russell just head-motioned to the window, looking at Mistress with a WTF face. 

"Oh that. I have an appointment in ten minutes. He wants to be taken over "Mommy's" knee and spanked until he's crying like a little girl. I figured I'd make him dress like one too," Mistress declared to both of us as she shrugged her arms and giggled. 

What a wild, magical place this was. I never wanted to leave!

slave sarah 

xoxo

Continued in: A quiet night in

  

 

Objectification

Continued from: Sarah's First Post

A post from Sarah

Almost 24-hours had passed, since I found myself bare naked in the palour of Mistress Andrea's Facility. I was being told to kneel, being told to keep my eyes down and how to position my arms. 

These were not requests, these were orders. I absolutely loved the simplicity of being told what to do. To not think, just obey.  

My clit jumped with each click of her high heels off the hardwood. Like a metronome of steady and commanding footsteps, when she approached and left me.

Since the first time I met her and she conducted her little "experiment", I cannot deny the fact that she tore a hole in the fabric of my identity. Despite her sexuality and her obvious gorgeousness, I'm just not attracted to women in that way. That is, until she started ordering me around, humiliating and degrading me...threatening to punish me. It has awoken something inside of me that I didn't know existed. 

My throbbing cunt is betraying me even now, as I sit here to type on Mistress' blog.

Carved from a corner of my bedroom, is my little WFH office. Between zoom calls, I've been trying to recount the events of yesterday afternoon, the first moment I had the privilege of calling Russell, 'Sir'.

It began with a different set of footsteps behind me. I knew it wasn't Mistress in her heels. I could also hear the distinct jingle of ice cubes in glass. 

Oh gawd! Oh I was so embarrassed and my god was he ever fucking hot! He sat and didn't acknowledge me, but glared toward my knelt state.

I was under instructions to keep my eyes lowered, which I did, but once Russell sat, I could see most of him. I didn't think it was possible to feel more naked, than fully naked, but I did. Being naked in a room with someone who is fully clothed is deathly vulnerable. My pussy betrayed me yet again, and started to slick my inner thighs. 

He smiled at me once, maybe to reassure me, before picking up his drink and taking a sip. He cleared his throat and spoke for the first time. 

"This is what you want?" He said, all raspy and sexy-like. His words were chosen carefully. It was almost a question, but had the tone of a statement. It was a masterful choice of words. It limited my control and decision making, although I did answer him. 

"Yes please, Sir," I squeaked out, without hesitating. 

I trembled when he came to help me up, using a firm grip on my wrist. I was taken to the corner of the room, to the padded apparatus affixed to the wall. He cinched-down the binds on my wrists until I was forced onto my toes, then he cuffed my ankles in place. 

Kneeling in a room, anticipating what's to come, provides a great deal of time to scan and interpret visual stimulus. It was not lost on me that Mistress positioned my body facing the coffee table. It was not lost on me that the blinds to this room were left open and a-top the coffee table, were two clothespins and a flogger. 

And now, I was at my most vulnerable of the session, bound, exposed and naked, in the presence of this intimidatingly, gorgeous man. 

He knelt down as he approached me, running a finger along the tops of my feet and toes, finally onto my toenails. 

"Keep these painted for me, baby pink," was all he said. 

I replied with a, "yes Sir." I was dreadfully embarrassed that my toenails were not done for him.

He ran a muscular hand up my leg and thigh and onto my pussy which he grabbed in a fist motion. I gasped out loud as he did. 

"Keep this shaved bald for me, slut." He hissed. "Your asshole too, hairless."

I groaned out loud in pure, desperate arousal. It was involuntary. I was such a whore to have groaned like that. But fuck me! He was inspecting me! Claiming me! Like my Master had just purchased me at some seedy auction. 

He continued his horrible and beautiful objectification, cupping my tits in his palms for a light bounce. Then his fingertips reached for both of my nipples. It was more of a swirl than a pinch. 

"These need to be a little more responsive." He said out loud. 

Not knowing what to do, or if this was a moment I should speak, I blurted out a, "I'm sorry Sir, I'll do better for you." 

He returned to the couch to sit, sipping from his drink once more. 

He cradled the cold, wet glass in his hands long enough to achieve his objective. He walked back to me and held my nipples with his freezing cold fingertips. They hardened instantly, and goosebumps fluttered across my body. 

"That's better." He commented, in a cavalier tone, before retrieving both clothespins and affixing them to my erect nipples. There was the sharp pain I was wanting, or at least my cunt was wanting. Now we were getting somewhere. 

Master picked up the flogger next, and proceeded to whip my stomach, ribs and tits with the vicious strands of leather. He whipped my tits and nipples until the clothespins came flying off from the impact, causing me to shriek in pain.

"You may scream. There is no shame in it." He calmly counselled, as I struggled to catch my breath through my whimpers. 

Master undid my bondage next, catching me as I was about to collapse down onto the floor. I guess being on my toes for so long had my legs shaky and spent. But on my knees in a puddle of my own degradation, was exactly where he wanted me.  

He controlled my wrists, and he was no longer in his pants, as he dragged me to the middle of the room. 

Nothing was said. He just mashed his erect penis against my lips, until I opened and took him into my mouth. Master has a lovely sized cock. I wasn't sucking it...he was fucking my face and throat with it. 

 

There was lots of beautiful gagging and gucking sounds, which only degraded me further. 

I tried to use my hands at one point, on his cock. I was quickly and sharply slapped in the face. Not at all violently, it was corrective. I need correction in this role, I have dreamed of being corrected in this way. 

He simply said, "No!" After the slap. Like he was scolding a dog. I carried on with only my mouth, like the filthy slut that I am, until Master came down my throat and onto my face. 

After this, I was told I was getting another whipping. 100 lashes to be exact, on my bare bum, back and thighs. Master was very specific this time, with what he intended to do. Likely because I was once again bound into a stress pose, to be left and to anticipate this flogging. Only this time, I was wearing his cum on my face, proudly!

slut sarah

xoxo

Continued in: All Three Holes