A sissy visits the Headmistress

Relentlessly the strict Miss Stern administered a thorough fingerfucking of my tight and sensitive sissy pussy. She withdrew her finger completely, and then let it slowly pass through my elastic sphincter again. My anal muscles contracted helplessly around the intruder. I felt a depraved passion stirring in my bowels, begging for the touch of my devious Mistress, longing for her finger to again bury itself inside my pussy, wanting the thrill of having it filled by her. So of course, she denied me that satisfaction. She wanted me to beg for it. To plead for her touch. And this depraved act: To ask for her finger inside me, made my young blood boil with an electric vibration.

"Please.. pleeeaaase.... Mistress... please.. put your finger in my pussy... inside me.. ohhh yesss... please Ma'am... Ohh... yesss.... you're so good to me... "

Smack. Smack.

"Yes, please, spank my naughty butt, Madam. Oh yes... and you finger... it's so good , ohhh please don't stop...."

But she did stop, this devil of a disciplinarian, and left me hanging on the brink, screaming for release, frantically wriggling my sore arse in order for her to caress it, punish it, touch it, anything... just for the feel of her hands on my tortured flesh.

She moved to the other side of the desk and sniffed thoroughly at the forefinger that had so recently been buried inside my sissy pussy.

"Smell yourself, you slutty little sissy," she said. And thrust her finger beneath my nose.

I inhaled, perversely excited by the act of smelling my own sissy pussy on her finger.

"Ahh, yes, you love that, you awful little minx! I'll see to it that your pussy gets the right attention. But first you must be punished further. Though, maybe..? Yes, I think so! Lick it!"

Taken by surprise I almost gagged as Miss Stern suddenly thrust her smelly finger into my unexpecting mouth!

"Suck it, you filthy little slave slut! Suck your Mistress' finger, which has just been buried deep inside your tight pussy! Suck it!"

So, suck it I did. I had no choice, and the truth is, I reveled in the smell and taste of my sissy pussy, served on the long finger of my dominant and very strict Headmistress! An intoxicating bitterness, a saltiness and an intoxicating musk. So, I diligently cleaned Miss Stern's forefinger of all traces of its visit to my insides, and afterwards thanked her for the privilege. She liked that and surprised me by kissing me deeply and stroking my hair.

"You're a sweet darling sissy, Rose. Sometimes. But you need very thorough discipline and punishment to keep you in line. Now I will let you get to know the hairbrush!"

Oh, it was nice, pleasurable even, to have her comb my hair with the heavy wooden brush she found.

"So, my little slut, this hairbrush I'm using to comb you with now, is also my favorite implement for corporeal punishment of young sissy ladies like you! It's heavy, made from good hardwood and has a smooth round handle, ideal for slipping into constricted orifices. The bristles are natural, stiff and yet elastic, perfect for providing variation to the more heavy slaps of the flat side of the brush. Kiss it!"

In fearful anticipation of the strict spanking about to be delivered by my Mistress, using the threatening hairbrush, I complied and bestowed the cool lacquered wood with fervent kisses, thus perhaps securing some leniency.

"Very well, Rose," the formidable Mistress then said, and laid the brush to the side.

"I will now allow you a very special privilege, as you have been well-behaved up to now. You will now be allowed to sniff your Mistress' panties! Only sniff them, mind you! I'll accord you no other caress but the rubbing of your pouty little nose against the silk of my underwear! Do you understand?"

I was ecstatic! A deep fluttering started inside me and made me treble with desirous agitation. I could not admit it, but my body knew beyond any doubt that I was totally lost in my perverted awe of Miss Stern. Her seditious manner had so stimulated my senses that no logic was left. Only an awakening desire to submit and please.

"Yes, Madam... I.. I understand... Please, Ma'am, may I be allowed to... to.. to sniff your panties, Miss Stern?"

"Would you like that, my sweet submissive, Sapphic sissy loveslut? Would you like to smell my panties which have become somewhat moist with my excretions? Spanking your voluptuous arse has made my womanly juices flow.... Would you like to stick your nose into that pungent juice and sniff to your hearts content? Oh, yes, I know sissies like you, Rose! You want this more than anything else the in world right now! Well, you shall have your wish!"

She faced me, and then slowly raised her magnificent black skirt. She was wearing black silken stockings and cream-colored silk underwear, with just a border of elegant lace. I drew my breath in, and had to sniff, to try and catch a whiff of her female scent. A distinct wet spot was visible where the panties were stretched tight over her generous pudendum. My Mistress was definitely aroused, and the gash between her thighs had seeped a copious amount of womanly secretions into the silken fabric.

"So, my sweet sissy! Do you like you Mistress' panties? Hmmm?"

"Yes, Ma'am... very much.. You're very beautiful, Mistress Stern!"

"Ahh, girl! Flattery will get you nowhere -- but so sweet of you, anyway!"

My headmistress now, ever so slowly, climbed up on the massive desk, and ended up on her knees with the black skirt just brushing my face. In my bound condition, I could not move my head much, but she ordered me to tilt it upwards as much as possible. Miss Stern now slowly moved forward, capturing my upturned face beneath her skirt and then bent forward, supporting herself with her hands on the desk. Then, inch by controlled inch, she lowered her hips down towards my eager visage.

Trapped in the darkness under Miss Sterns black skirt, I could hear the gentle rustle of silk rubbing silk and then her fragrant scent enveloped me, and I was lost to the outside world. Musky, salty notes mixed with a cinnamon spiciness and the pungency of ripening fruit. She was also wearing a flowery perfume, which mingled with the odor of her sexual emanations, concocting a cocktail of such power, I lost sense of anything else.

Gone were the aches in my bound body, the dull pain in my spanked derriere, the pressure on my chest squeezed onto the top of the oaken desk. What was left was only a sissy schoolgirl under the spell of her dominant Headmistress and eager to please and perform her allotted task: To smell the panties of a mature woman, panties inundated with the intoxicating essence of female arousal.

Then, oh joy, my nose contacted the silk fabric of Miss Sterns underwear. The moist crotch of the tightfitting panties glued to her slit, which was drenched in viscous, fragrant juice. My Mistress maneuvered above me, so the tip of my nose was buried within her paradisiacal grotto, and then she rubbed herself with small movements of her lower body, on my upturned face.

I inhaled deeply and rode on a burst of olfactory bliss as my nose rubbed into the increasingly more drenched slit, gliding in the viscous excretions of Mistress Stern. In addition to this, the feeling of the warm silk, oiled in her smooth fluids, against my nose was exquisite beyond my wildest imaginations.

Never had I know such gratification! I was totally, utterly captivated, and could not resist sticking out my tongue for an illicit taste of the sweetness I was submerged in. She knew, of course, the glorious woman above me, that this would happen. She had planned it this way, as she had planned for my total subjugation and seduction. She immediately stopped her rubbing action and delivered two vicious spanks to by buttocks.

"No tasting, you disobedient sissy slut! You may not lick your Mistress unless specifically ordered! This will make your upcoming spanking all the more severe."

Smack. Smack. Hard spanks rained down over my defenseless behind and I yelped with pain.

"Instead you must sniff at my arsehole, you dirty hussy!"

Above me, she moved. The skirt rustled, light momentarily was let into my silken prison, then darkness again descended. Repositioned, Miss Stern proceeded to lower her pantie-clad behind down over my prostate face. I was apprehensive at the prospect of being smothered beneath her fleshy -- but firm -- globes, but again the diabolic intent of Miss Stern asserted itself. With infinitesimal small movements of her derriere she managed to get the tip of my nose right on top of the entrance to her anal passage. She kept still then, and only clenched the muscles of her butt, rhythmically caressing my captured organ of smell between her velvety buttocks.

Helpless, my senses were assaulted by this treatment. From her nether hole emanated a bitter, earthy scent. Not unpleasant and mingled with the lingering scent of her femaleness, it created a sucking longing inside me, and I actually started to deeply draw in the odor of my Mistress' ass through widely dilated nostrils, reveling in the complete debasement of the situation.

"Yes, yes, you little arse-sniffer... I knew you'd like this... having your pouty little nose up my ass! Now, press it against my asshole.. that's it... rub it there... good sissy... But don't you dare lick!"

I did not lick. I didn't have to. Miss Sterns silken panties were so inundated with her essence that my pouted lips, so close in contact with the drenched fabric, were constantly wetted! There I was, an eighteen-year-old sissy schoolgirl bound and spanked by a much older dominant woman, and now my face was beneath her black skirt and she was riding my poor face, using my nose to titillate her anal rosebud and making me sniff her most intimate places.

And I wanted it. More than anything I'd ever wanted, I wanted this to continue forever. I wanted her firm hand kneading my glowing buttocks, I wanted her to violate my buttocks with her wooden hairbrush, I wanted to please her, adore her, gratify her.

Moaning incoherently, I eagerly rubbed my nose over her anal entrance and distinctly felt the wrinkled hole elastically give slightly and accommodate the very tip of my nose. Then Miss Stern clenched her rosette and slowly climbed down form her position on top of the oaken desk.

"Now, you disobedient little sissy slut, it's time for your hairbrush spanking! Ask your Mistress nicely for your well-deserved punishment."

"Please, Mistress, please spank my arse with your hairbrush... I've been so naughty, Mistress.. I... I need to be punished.. pleeeese spank me, Ma'am..."

She stood behind me and I no time to prepare. A quick, hard slap hit my left buttock with a resounding smack, then the right. A dull, warm glowing pain throbbed in the spanked areas and I clenched my cheeks involuntarily. My severe Headmistress then promptly delivered a series of stinging blows to my exposed buttocks. She grasped the tight cotton panties and pulled them upwards strongly, thus causing me to almost stand on the tip of my shoes and pressing my abused arse slightly up and out, presenting it more invitingly for the heavy slaps of the relentless brush.

I felt tears well up into my eyes with the severity of the punishment I was subjected to, and my bottom flesh soon felt as if it was on fire. Still the harsh Headmistress did not stop. She moved her attention downwards, though, treating my upper thighs to a rapid pummeling with the heavy brush. Slap after stinging slap hit my vulnerable skin and I was powerless. I could do nothing to stop Miss Sterns discipline. A numbness blissfully set in after a while, as the heat spread with the reddening of my rear and thighs, and the pain I felt initially lessened somewhat. The imposing headmistress, however, did not soften her spanks, and I was almost delirious when she stopped, hanging powerless in my strict bondage, silently sobbing.

"So, little one, did you enjoy your spanking? It will make you feel better, you know. Much better than you've ever felt in your life. Just let go, sweetie. Let me take care of you and your needs. I'll dry your tears now, dear, and then I'll treat your lovely derriere to some nice cold cream and a little brushing. Just relax now."

Through eyes hazed with tears, I glimpsed Miss Stern, as she languidly posed before me and ever so slowly removed her wet silken panties, the ones I had so recently licked. She proceeded to wipe my face with the fragrant silk, not really drying me, but distributing her thick juice on my face. She left the panties on me, with the moist gusset placed over my mouth and my eyes free to watch her.

Miss Stern now bent down, kissed me through her own juice-imbued panties and stroked my messy hair beneath the silk. I was hurting from her relentless treatment of my behind but also trembling with the sheer erotic sensation of being forced in this manner to inhale her female excitement with my every breath. The panties were very wet with her fluids and clung to my skin.

My Mistress turned her attention to my glowing backside. She cut my panties at the sides with a pair of scissors and in my view brought them to her nose and inhaled deeply.

"Mmm, the sexual essence of a subservient sissy! Such a fresh, sweet aroma! Don't you think so, slut?"

And she stuffed my cut panties inside her own, mingling my scent with her own. Playfully she rubbed the resulting bundle of panties decorating my face, thus forcing me to draw my breath through not only hers, but also my own, soggy underwear. I closed my eyes and relished the potent mixture, wanting my sissy excretions to mingle with my Mistress's much more mature female exudations.

I suddenly felt a coolness on my warm skin, and Miss Stern gently rubbed a generous amount of cold cream into my sore buttocks, thus soothing the pain. She carefully applied the cream all over my recently spanked derriere, and also smeared the crease between my orbs. Her forefinger played a tickling dance on my small rosette, and then it was, again, buried inside me, lubricating my sissy pussy.

She let me rest then, for a little while, and then she again took the fearsome hairbrush to my bottom. Not to spank me with, this time, but to let the bristly side of the brush tease and massage my buttocks. At first Miss Stern used the brush to gently caress my inflamed behind with small circular motions. The stiff bristles abraded my sensitized skin, as my Headmistress well knew. Blood suffused to my sore bottom and heated it, after the cooling action of the cold cream. She started tapping my vulnerable, quivering orbs with the bristly hairbrush causing a prickling, but not unpleasant, frisson.

Mistress Stern carefully covered all of my rear with this brushing and tapping action, and by the end of it I was gasping through the soggy panties covering my mouth and wriggling my arse in response to the devious treatment. My very erect clit was fairly oozing its cream of sexual ecstasy, my breath was raggedly irregular, and fluttering butterflies trembled within my breast.

Then, to my consternation, the insidious hairbrush found its ways between my widely spread legs and began a slow, almost imperceptible, brushing of my tied up sissy plums.

"So, you lecherous, disobedient girl! Do you want to have your naughty little sissy clitty spanked, Hnnn? Would you like to feel my hairbrush on you sweet little cockette, eh, Rose?"

"Yes... yes, Ohh.. yes, please, Ma'am! Please... I'm such a disobedient sissy.. I .. I need my clit.. my clitty spanked, Ma'am. Please spank my naughty, little sissy clitty, Ma'am, please...., please punish me..."

I was delirious with Mistress Stern's heady and seductive mix of pain and pleasure delivered with a thorough knowledge of the physical and psychological triggers of a sissy, such as I.

With small, circular motions of the hairbrush, Miss Stern rubbed my sensitive sissy plums and clit.

Slap!

I almost choked on the panties with the shock. The flat, wooden side of the brush hit the area between my plumsack and my pussy with a resounding smack and caused a dull ache to throb in my moist, juiceslick sex.

"Ask for it, you bad, bad sissy girl! And thank your Mistress!"

"Pleease..., Madam... Thank... you... please... may I have... another?"

I knew the drill by now, and it gave me a deep, satisfying thrill to be thus induced to beg my Headmistress for such intimate punishment.

Again, the hairbrush met my exposed sex with relentless force, but the resulting aching pain only made me subconsciously push my bottom back, towards Miss Stern, silently inviting her to proceed with her harsh correction.

"Thank.. you, Ma'am, I gasped. May... may I please have another?"

My privates burned with heat resulting from the slaps, and although a pain lingered, a throbbing excitement was the result. My clitoris stiffened and fluids continuously dripped from my clit-slit. I did want another slap of the brush! I longed for the heady mingling of pain and delirious pleasure that was the result of hard wood meeting my vulnerable flesh. And when the brush again smacked without mercy on my reddening genitalia,

I did not really feel any pain. Only a warming, glowing sensation, which Miss Stern further enhanced after the smack by using the bristly side of the brush to caress my skin and even let the bristles gently caress the tip of my erect clit and my pussy sphincter.

I left the hard desk, on which I was so securely bound, and left for another world, where the only thing that mattered was the will of Mistress and the elation of submission. A world, where I, a naughty sissy schoolgirl, begged for my young pussy to be spanked by my authoritarian Headmistress.

"Thank you, Ma'am. Please, Ma'am, may I have another!"

Smack!

And on it went, for an eternity. Until my clit was red and raw and throbbed painfully for release and I sobbed with sweet frustration and the dark longing grew between by loins. She stood close behind me, then, and her skirt was cool on my buttocks. Her hands played with my bosom as she leant forward and nibbled me earlobes and whispered:

"So, did my naughty sissy like her clit- and pussy-spanking? Is that sweet sissy-clit all red and bothered now, eh? And your nose buried in those panties of ours -- sniffing your own scent mixed with mine. Good isn't it, Rose? Oh, yes, I know all about it. How you like to beg nicely for your punishment. How you crave release. But only I can give you release, you bad girl. Only I can fulfil those dreams you have. You are mine now, Rose. My little plaything and lesbian sissy girl-toy. And you'll do anything for me. No matter how degrading and debased. Anything. Won't you? Just to feel my hairbrush again softly caressing the wet, wet tip of your erect little clittie."

"Yees... yes... Ma'am ... I'm your... sissy lesbian, Ma'am... and I'll do.. anything....!"

"Yes, you will do anything. Soon. But first I will do something...."

She knelt behind me, and I felt her breath on my behind. My dominant Mistress then carefully exposed the crease between by buttocks and with an intruding finger started caressing the very entrance to my sissy pussy. Then something hard and unrelenting slid through my lubricated anal opening and filled me out.

"Ah, yes.. a hairbrush is so versatile on a girl! The handle so very suited to explore the dark secrets of your tight sissy pussy! Yes, good girl, take it all in. That's it. Feel how it tapers off a little just before the actual head of the brush? Good. Clench tightly, my sweet, because I'll punish you most severely if you drop it! I'll free your bonds now, and I want you to stand before me and remove your shoes, socks and remaining clothes -- without losing the hairbrush inserted inside you. Is that perfectly clear, young lady?"